# Patent

## Title
Condensed cyclic compound and organic light-emitting device including the same

## Abstract

A condensed cyclic compound represented by one of Formulae 1A to 1C, wherein Formulae 1A to 1C are disclosed in the detailed description.

## Background
CROSS-REFERENCE TO RELATED APPLICATION
This application claims priority to Korean Patent Application No. 10-2014-0058395, filed on May 15, 2014, in the Korean Intellectual Property Office, and all the benefits accruing therefrom under 35 U.S.C. §119, the content of which is incorporated herein in its entirety by reference.
BACKGROUND
1. Field
One or more embodiments relate to condensed cyclic compounds and organic light-emitting devices including the same.
2. Description of the Related Art
Organic light-emitting devices (OLEDs) are self-emission devices that have wide viewing angles, high contrast ratios, and short response times. In addition, the OLEDs exhibit excellent brightness, driving voltage, and response speed characteristics, and produce full-color images.
A typical organic light-emitting device includes an anode, a cathode, and an organic layer that is disposed between the anode and the cathode and includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, are recombined in the emission layer to produce excitons. These excitons change from an excited state to a ground state, thereby generating light.
Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.
SUMMARY
Provided are novel condensed cyclic compounds and organic light-emitting devices including the same.
Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.
According to an aspect, a condensed cyclic compound is represented by one of Formulae 1A to 1C:







wherein in the formulae,
Ring A is a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a group represented by Formula 2A, or a group represented by Formula 2B;
Ring B1 is a C5-C20 carbocyclic group or a C2-C20 heterocyclic group that does not include a nitrogen atom as a ring-forming atom;
Ring B2, Ring B3, Ring C1, and Ring C2 are each independently a C5-C20 carbocyclic group, or a C2-C20 heterocyclic group, provided that at least one selected from Ring B2 and Ring B3 is a C2-C20 heterocyclic group including a nitrogen atom as a ring-forming atom, and at least one selected from Ring C1 and Ring C2 is a C2-C20 heterocyclic group including a nitrogen atom as a ring-forming atom;
Pc1 and Pc2 in Formula 1A and 1B are each independently a group represented by Formulae 2A or a group represented by Formula 2B;
Cz1, Cz2, and Cz3 in Formula 1C are each independently a group represented by Formula 2C, a group represented by Formula 2D, a group represented by Formula 2E, or a group represented by Formula 2F;
c1, c2, c11, c12, c13, p1, p2, p11, p12, and p13 are each independently an integer selected from 0 to 3;
when c1 and c2 in Formula 1A and 1B both are 0, Ring A is a group represented by Formula 2A or a group represented by Formula 2B;
when Ring A in Formula 1A and 1B is neither a group represented by Formula 2A nor a group represented by Formula 2B;

c1+c2≠0;

at least one selected from Ring A in Formula 1A, all R1 in Formula 1A, and all R2 in Formula 1A is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each including at least one Moiety 1 as a ring-forming moiety;
the sum of c11, c12, and c13 in Formula 1C is not 0;
when each of Cz1, Cz2, and Cz3 in Formula 1C is independently a group represented by Formula 2C or a group represented by Formula 2D, at least one selected from all R11 in Formula 1C, all R12 in Formula 1C, and all R13 in Formula 1C is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each including at least one Moiety 1 as a ring-forming moiety;
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently selected from a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed hetero-polycyclic group;
a1 to a3, a11 to a13, a21 to a24, and a31 to a33 are each independently an integer selected from 0 to 6;
R1, R2, R11 to R13, R21 to R23, and R31 to R33 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7);
b1, b2, b11 to b13, b21 to b23, and b31 to b33 are each independently an integer selected from 0 to 4;
at least one of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed hetero-polycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37);
wherein Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 may be each independently selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.

**═N—***  Moiety 1

in Moiety 1, ** and *** each indicates a binding site to a ring-forming atom included in a ring including Moiety 1.
According to another aspect, an organic light-emitting device includes:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer includes an emission layer, and further includes at least one condensed cyclic compound represented by Formula 1.



BRIEF DESCRIPTION OF THE DRAWINGS
These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with FIG. 1 which is a schematic view of an organic light-emitting device according to an embodiment.



DETAILED DESCRIPTION
Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. The term “or” means “and/or.” Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.
It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.
It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.
The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.
It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.
Spatially relative terms, such as “beneath,” “below,” “lower,” “above,” “upper” and the like, may be used herein for ease of description to describe one element or feature's relationship to another element(s) or feature(s) as illustrated in the figures. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation in addition to the orientation depicted in the figures. For example, if the device in the figures is turned over, elements described as “below” or “beneath” other elements or features would then be oriented “above” the other elements or features. Thus, the exemplary term “below” can encompass both an orientation of above and below. The device may be otherwise oriented (rotated 90 degrees or at other orientations) and the spatially relative descriptors used herein interpreted accordingly.
“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.
A condensed cyclic compound according to an embodiment is represented by one of Formulae 1A to 1C:







The relationships between the groups represented by Formulae 2A to 2F and the condensed cyclic compound represented by one of Formulae 1A to 1C will be described below in detail.
Ring A in Formula 1A may be a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a group represented by Formula 2A, or a group represented by Formula 2B.
According to an embodiment, Ring A in Formula 1A may be selected from
a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyrimidinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group, a benzothienopyridinyl group, a group represented by Formula 2A, and a group represented by Formula 2B; and
a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyrimidinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group, and a benzothienopyridinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a phenyl group substituted with a C1-C20 alkyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35),
wherein Q33 to Q35 may be each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.
In some embodiments, Ring A in Formula 1A may be represented by one of Formulae 4-1 to 4-51, Formulae 6-1 to 6-5 below, a group represented Formula 2A, and a group represented by Formula 2B, but a formula representing Ring A is not limited thereto:
















In Formulae 4-1 to 4-51 and 6-1 to 6-5,
Y31 is O, S, C(Z33)(Z34), N(Z35), or Si(Z36)(Z37);
Z31 to Z37 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group substituted with a C1-C20 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35); wherein
Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;
e1 is an integer of 1 to 5;
e2 is an integer of 1 to 7;
e3 is an integer of 1 to 3;
e4 is an integer of 1 to 4;
e5 is an integer of 1 or 2;
e6 is an integer of 1 to 6; and
* indicates a binding site to a neighboring atom.
Ring B1 in Formula 1A is a C5-C20 carbocyclic group or a C2-C20 heterocyclic group that does not includes a nitrogen atom as a ring-forming atom.
For example, Ring B1 in Formula 1A may be a benzene, a naphthalene, an anthracene, a phenanthrene, a benzofuran, or a benzothiophene.
According to an embodiment, Ring B1 in Formula 1A may be a benzene, a naphthalene, an anthracene, a phenanthrene, or a benzofuran.
Ring B2, Ring B3, Ring C1, and Ring C2 in Formulae 1B and 1C are each independently a C5-C20 carbocyclic group or a C2-C20 heterocyclic group, provided that at least one selected from Ring B2 and Ring B3 is a C2-C20 heterocyclic group including a nitrogen atom as a ring-forming atom, and at least one selected from Ring C1 and Ring C2 is a C2-C20 heterocyclic group including a nitrogen atom as a ring-forming atom.
In some embodiments, Ring B2, Ring B3, Ring C1, and Ring C2 may be each independently a benzene, a naphthalene, an anthracene, a phenanthrene, a benzofuran, a benzothiophene, a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine;
at least one selected from Ring B2 and Ring B3 is a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, a benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine, and
at least one selected from Ring C1 and Ring C2 is a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, a benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine.
In some embodiments, Ring B2, Ring B3, Ring C1, and Ring C2 may be each independently a benzene, a naphthalene, a pyridine, a pyrimidine, or a pyrazine;
at least one of Ring B2 and Ring B3 may be a pyridine, a pyrimidine, or a pyrazine; and
at least one of Ring C1 and Ring C2 may be a pyridine, a pyrimidine, or a pyrazine.
Pc1 and Pc2 in Formula 1A and 1B are each independently a group represented by Formulae 2A or a group represented by Formula 2B.
Each of Cz1, Cz2, and Cz3 in Formula 1C is independently a group represented by Formula 2C, a group represented by Formula 2D, a group represented by Formula 2E, or a group represented by Formula 2F.
c1, c2, c11, c12, c13, p1, p2, p11, p12, and p13 in Formulae 1A to 1C are each independently an integer selected from 0 to 3.
When each of c1 and c2 in Formulae 1A and 1B is 0, Ring A is a group represented by Formula 2A or a group represented by Formula 2B, and when Ring A in Formulae 1A and 1B is neither a group represented by Formula 2A nor a group represented by Formula 2B, c1+c2≠0.
That is, Formulae 1A and 1B necessarily include one selected from the group represented by Formula 2A and the group represented by Formula 2B.
At least one selected from Ring A in Formula 1A, all R1 in Formula 1A, and all R2 in Formula 1A is an electron transport moiety.
The electron transport moiety may be a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each including Moiety 1 below as a ring-forming moiety. Herein, a carbazole-based group that does not include Moiety 1 is not an electron transport moiety, due to the absence of Moiety 1.

**═N—***  Moiety 1

in Moiety 1, ** and *** each indicates a binding site to a ring-forming atom in a ring including Moiety 1.
Examples of the electron transport moiety are groups represented by Formulae 4-1 to 4-51, but are not limited thereto.
The sum of c11, c12, and c13 in Formula 1C is not 0.
That is, Formula 1C necessarily includes at least one of groups represented by Formulae 2C to 2F.
When Cz1, Cz2, and Cz3 in Formula 1C is a group represented by Formula 2C or a group represented by Formula 2D, at least one selected from R11 in Formula 1C, R12 in Formula 1C, and R13 in Formula 1C is an electron transport moiety. Herein, the electron transport moiety has been described above and will not be repeated.
According to an embodiment, in Formulae 1A and 1B,
c1=0, c2=0, and Ring A is a group represented by Formula 2A or a group represented by Formula 2B;
c1=1 and c2=0; or
c1=1 and c2=1.
In some embodiments, in Formula 1C,
c11=1, c12=0, and c13=0;
c11=0, c12=0, and c13=1;
c11=1, c12=1, and c13=0; or
c11=1, c12=0, and c13=1.
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 in Formulae 1A to 1C and 2A to 2F may be each independently selected from a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed hetero-polycyclic group.
For example, L1 to L3, L11 to L13, L21 to L24 and L31 to L33 in Formulae 1A to 1C and 2A to 2F may be each independently selected from
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and
a phenylene group, a pentalenylene group, an indenylene group, naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group an imidazopyrimidinylene group, and an imidazopyridinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C2-C20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, and —Si(Q33)(Q34)(Q35);
wherein Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group.
According to an embodiment, L1 to L3, L11 to L13, L21 to L24 and L31 to L33 in Formulae 1A to 1C and 2A to 2F may be each independently one selected from Formulae 2-1 to 2-37:













wherein in Formulae 2-1 to 2-37,
Y1 may be O, S, S(═O), S(═O)2, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7);
Z1 to Z7 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q45), wherein
Q33 to Q45 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group;
d1 is an integer of 1 to 4;
d2 is an integer of 1 to 3;
d3 is an integer of 1 to 6;
d4 is an integer of 1 to 8;
d5 is an integer of 1 or 2;
d6 is an integer of 1 to 5; and
* indicates a binding site to a neighboring atom.
In some embodiments, L1 to L3, L11 to L13, L21 to L24 and L31 to L33 in Formulae 1A to 1C and 2A to 2F may be each independently selected from
a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group; and
a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a phenanthrenyl group, and a biphenyl group, but they are not limited thereto.
In some embodiments, L1 to L3, L11 to L13, L21 to L24 and L31 to L33 in Formulae 1A to 1C and 2A to 2F may be each independently one of Formulae 3-1 to 3-33, but are not limited thereto:













wherein * and *′ in Formulae 3-1 to 3-33 each independently indicates a binding site to a neighboring atom.
a1 in Formulae 1A to 1C indicates the number of L1, and may be 0, 1, 2, 3, 4 or 6, for example, 0, 1 or 2, or for example, 0 or 1. When a1 is 0, L1 is a single bond. When a1 is 2 or more, groups L1 may be identical or different. a2 to a3, a11 to a13, a21 to a24 and a31 to a33 may be understood by referring to the description presented in connection with a1 and structures of Formulae 1A to 1C and 2A to 2F.
According to an embodiment, a1 to a3, a11 to a13, a21 to a24 and a31 to a33 in Formula 1 may be each independently 0, 1, or 2, for example, 0 or 1, but they are not limited thereto.
R1, R2, R11 to R13, R21 to R23, and R31 to R33 in Formulae 1A to 1C and 2A to 2F may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, a group represented by Formula 2A, a group represented by Formula 2B, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7).
For example, R1, R2, R11 to R13, R21 to R23, and R31 to R33 may be each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a phenyl group substituted with a C1-C20 alkyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35); and
—Si(Q3)(Q4)(Q5);
wherein Q3 to Q5 and Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.
In some embodiments, R1, R2, R11 to R13, R21 to R23, and R31 to R33 may be each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
one selected from Formulae 4-1 to 4-51, 5-1 to 5-6, and 6-1 to 6-5; and
—Si(Q3)(Q4)(Q5),
wherein Q3 to Q5 may be each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but they are not limited thereto.






















wherein in Formulae 4-1 to 4-51, 5-1 to 5-6, and 6-1 to 6-5,
Y31 is O, S, C(Z33)(Z34), N(Z35), or Si(Z36)(Z37);
Z31 to Z37 may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group substituted with a C1-C20 alkyl group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35); wherein
Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;
e1 is an integer of 1 to 5;
e2 is an integer of 1 to 7;
e3 is an integer of 1 to 3;
e4 is an integer of 1 to 4;
e5 is an integer of 1 or 2;
e6 is an integer of 1 to 6; and
* indicates a binding site to a neighboring atom.
b1, b2, b11 to b13, b21 to b23, and b31 to b33 in the formulae above may be each independently an integer selected from 0 to 4. For example, b1, b2, b11 to b13, b21 to b23 and b31 to b33 may be each independently 0 or 1, but they are not limited thereto.
Formula 2A may be represented by one of Formulae 2A(1) to 2A(5) below, Formula 2B may be represented by one of Formulae 2B(1) and 2B(2) below, Formula 2D may be represented by one of Formulae 2D(1) to 2D(5) below, and Formula 2F may be represented by one of Formulae 2F(1) and 2F(2) below:










L21 to L24, a21 to a24, R21 to R23, b21 to b23, L31 to L33, a31 to a33, R31 to R33, b31 to b33, c21 to c23, c31, and c32 in Formulae 2A (1) to 2A (5), 2B(1), 2B(2), 2E(1) to 2E(5), 2F(1), and 2F(2) are as described above.
For example, a24 in Formulae 2A(1) to 2A(5), 2B(1), and 2B(2) is 0, 1, or 2, and L24 is selected from Formulae 2-1 to 2-37, and c11, c12, and c13 may each be a hydrogen, but they are not limited thereto.
The condensed cyclic compound represented by Formula 1 may be represented by one of Formulae 1A(1) to 1A(8) below:







In Formulae 1A(1) and 1A(8),
Ring A is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each including Moiety 1 as a ring-forming moiety, (for example, a group represented by one of Formulae 4-1 to 4-55),
Pc2, Pc2, L3, a3, R1, R2, p1, and p2 are as described above, and
R3 to R4 are as described above.
In some embodiments, the condensed cyclic compound represented by Formula 1 may be represented by one of Formulae 1B(1) to 1B(10) below:







Ring A, Pc1, Pct, L3, a3, R1, R2, p1, and p2 in Formulae 1B(1) to 1B(10) are as described above.
In some embodiments, the condensed cyclic compound may be represented by Formulae 1C(1) or 1C(2) below:




Cz1, Cz2, Cz3, R11, R12, R13, p11, p12, and p13 in Formulae 1C(1) and 1C(2) are as described above.
In some embodiments, the condensed cyclic compound may be represented by Formulae 1C(3) below:




wherein in Formula 1C(3),
Cz3, L11, and a11 are as described above;
R11 may be a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each including Moiety 1 as a ring-forming moiety, (for example, a group represented by one of Formulae 4-1 to 4-55); and b11 is 1 or 2.
In some embodiments, the condensed cyclic compound may be represented by Formulae 1C(4) or 1C(5) below:




wherein in Formulae 1C (4) and 1C (5), Cz1 and Cz3 are each a group represented by Formula 2E or a group represented by Formula 2F.
The condensed cyclic compound may be one of Compounds 1 to 76 below, but is not limited thereto:


















































































Formulae 1A and 1B necessarily include at least one group represented by one of Formulae 2A and 2B, and Formula 1C has a core that is substantially similar to Formulae 2A and 2B. Accordingly, excellent thermal stability may be obtained.
In some embodiments, Formula 1A necessarily includes the electron transport moiety (for example, see Formulae 4-1 to 4-55) used herein, at least one selected from Ring B1 and Ring B2 in Formula 1B necessarily includes at least one nitrogen as a ring-forming atom, and Formula 1C necessarily includes either the electron transport moiety used herein in its molecular structure or a group represented by at least one of Formulae 2E and 2F. Accordingly, the condensed cyclic compound represented by one of Formulae 1A to 1C may have excellent bipolar characteristics and high T1 energy levels, and due to these characteristics, the condensed cyclic compound is appropriate for use as a material for forming an electric device, for example, an organic light-emitting device. For example, the condensed cyclic compound represented by one of Formulae 1A to 1C may be appropriate for use as a host for an organic light-emitting device.
For example, the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), T1 energy level, and S1 energy level of Compounds 2 to 19 and 21 to 76 and Compounds A and B were simulated by using Gaussian, and simulation evaluation results are shown in Table 1 below:












TABLE 1







HOMO (eV)
LUMO (eV)
T1 (eV)
S1 (eV)




















Compound A
−5.113
−1.25
2.933
3.224


Compound B
−5.118
−1.589
2.856
3.039


Compound 2
−5.344
−1.916
2.912
3.02


Compound 3
−5.133
−1.991
2.627
2.731


Compound 4
−5.196
−1.798
2.781
2.947


Compound 5
−5.083
−1.792
2.862
2.928


Compound 6
−5.32
−1.891
2.74
2.924


Compound 7
−5.167
−1.973
2.424
2.767


Compound 8
−5.167
−2.019
2.399
2.728


Compound 9
−5.282
−1.664
2.924
3.04


Compound 11
−5.337
−1.933
2.886
3.01


Compound 12
−5.273
−1.953
2.773
2.919


Compound 13
−5.308
−1.84
2.733
2.999


Compound 14
−5.259
−1.992
2.47
2.835


Compound 15
−5.100
−1.793
2.878
3.040


Compound 16
−5.279
−1.691
2.901
3.085


Compound 17
−5.487
−1.957
2.865
3.126


Compound 18
−5.291
−2.015
2.455
2.845


Compound 19
−5.284
−1.925
2.508
2.924


Compound 76
−5.343
−1.927
2.802
3.023


Compound 21
−5.430
−1.997
2.836
3.012


Compound 22
−5.246
−2.021
2.688
2.804


Compound 23
−5.139
−2.004
2.643
2.743


Compound 24
−5.269
−2.015
2.727
2.843


Compound 25
−5.252
−2.018
2.7
2.816


Compound 26
−5.045
−1.996
2.554
2.649


Compound 27
−5.255
−1.934
2.811
2.846


Compound 28
−5.266
−2.011
2.737
2.87


Compound 29
−5.267
−1.985
2.713
2.837


Compound 30
−5.419
−1.992
2.697
2.965


Compound 31
−5.243
−1.972
2.697
2.821


Compound 32
−5.06
−2.01
2.564
2.656


Compound 33
−5.155
−2.007
2.657
2.764


Compound 34
−5.224
−2.004
2.523
2.843


Compound 35
−5.213
−2.012
2.538
2.804


Compound 36
−5.256
−1.997
2.693
2.819


Compound 37
−5.292
−2.004
2.704
2.837


Compound 38
−5.282
−2.001
2.559
2.833


Compound 39
−5.082
−1.974
2.586
2.696


Compound 40
−5.201
−1.986
2.64
2.769


Compound 41
−5.111
−1.939
2.576
2.703


Compound 42
−5.17
−2.035
2.403
2.726


Compound 43
−5.227
−1.279
2.917
3.191


Compound 44
−5.384
−1.78
2.849
3.121


Compound 45
−5.214
−1.222
2.92
3.129


Compound 46
−5.295
−1.327
2.918
3.108


Compound 47
−5.269
−1.302
2.915
3.158


Compound 48
−5.236
−1.387
2.894
3.057


Compound 49
−5.589
−1.653
2.986
3.32


Compound 50
−5.361
−1.704
2.892
3.24


Compound 51
−5.603
−1.914
2.907
3.102


Compound 52
−5.252
−1.675
2.927
3.062


Compound 53
−5.509
−1.857
2.499
3.107


Compound 54
−5.895
−1.767
2.992
3.297


Compound 55
−5.87
−1.693
2.959
3.345


Compound 56
−5.709
−1.642
2.532
3.188


Compound 57
−5.819
−1.894
2.667
3.124


Compound 58
−5.436
−2.124
2.924
3.016


Compound 59
−5.666
−1.853
2.865
3.096


Compound 60
−5.501
−1.492
2.713
3.119


Compound 61
−5.089
−1.762
2.745
3.022


Compound 62
−5.331
−2.008
2.827
2.925


Compound 63
−5.097
−1.815
2.053
2.901


Compound 64
−5.314
−2.015
2.587
2.804


Compound 65
−5.177
−1.964
2.571
2.816


Compound 66
−5.248
−1.655
2.662
3.094


Compound 67
−5.369
−1.413
2.879
3.118


Compound 68
−5.153
−1.984
2.785
2.839


Compound 69
−5.094
−1.804
2.734
2.94


Compound 70
−5.426
−2.123
2.73
2.977


Compound 71
−5.334
−1.938
2.868
2.964


Compound 72
−5.254
−1.915
2.441
2.887


Compound 73
−5.321
−1.918
2.894
3.017


Compound 74
−5.276
−1.926
2.305
2.971


Compound 75
−5.016
−1.580
2.186
2.964













From Table 1, it is confirmed that Compounds 2 to 19 and 21 to 76 have lower LUMO levels (that is, larger LUMO absolute values) than Compounds A and B. Accordingly, it is confirmed that the condensed cyclic compound represented by one of Formulae 1A to 1C is appropriate for use as a material for an organic layer, for example, an auxiliary layer or an emission layer, of an organic light-emitting device.
A method of synthesizing the condensed cyclic compound represented by one of Formulae 1A to 1C may be apparent to one of ordinary skill in the art by referring to Synthesis Examples used herein.
Accordingly, since the condensed cyclic compound represented by one of Formulae 1A to 1C is appropriate for use in an organic layer of an organic light-emitting device, for example, for use as a host in an emission layer of the organic layer, another aspect provides an organic light-emitting device including:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer includes an emission layer and at least one condensed cyclic compound represented by one of Formulae 1A to 1C.
Due to the inclusion of the organic layer including the condensed cyclic compound represented by one of Formulae 1A to 1C, the organic light-emitting device may have low driving voltage, high efficiency, high brightness, and long lifespan.
The condensed cyclic compound represented by one of Formulae 1A to 1C may be used between a pair of electrodes of an organic light-emitting device. For example, the condensed cyclic compound may be included in at least one selected from an emission layer, a hole transport region (including, for example, at least one of a hole injection layer, a hole transport layer, a buffer layer, and an electron blocking layer) that is disposed between the first electrode and the emission layer, and an electron transport region (including, for example, at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer) that is disposed between the emission layer and the second electrode. For example, the condensed cyclic compound represented by one of Formulae 1A to 1C may be included in the emission layer. In this regard, the emission layer may further include a dopant, and the condensed cyclic compound included in the emission layer may act as a host. The emission layer may be a green emission layer emitting green light or a blue emission layer emitting blue light, and the dopant may be a phosphorescent dopant.
The expression “(an organic layer) includes at least one condensed cyclic compound” as used herein may include a case in which “(an organic layer) includes identical condensed cyclic compounds represented by Formulae 1A to 1C and a case in which (an organic layer) includes two or more different condensed cyclic compounds represented by Formulae 1A to 1C.
For example, the organic layer may include, as the condensed cyclic compound, only Compound 1. In this regard, Compound 1 may be situated in an emission layer of the organic light-emitting device. In another embodiment, the organic layer may include, as the condensed cyclic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be situated in either an identical layer (for example, Compound 1 and Compound 2 all may be situated in an emission layer), or different layers.
The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode, or the first electrode may be a cathode, which is an electron injection electrode, or the second electrode may be an anode, which is a hole injection electrode.
For example, the first electrode is an anode, and the second electrode is a cathode, and the organic layer includes;
i) a hole transport region disposed between the first electrode and the emission layer, including at least one of a hole injection layer, a hole transport layer, and an electron blocking layer, and
ii) an electron transport region disposed between the emission layer and the second electrode, including at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.
The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of an organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.
FIG. 1 is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with FIG. 1. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.
In FIG. 1, a substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or transparent plastic substrate, each with excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water-proofness.
The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode on the substrate. The first electrode 11 may be an anode. The material for the first electrode 11 may be selected from materials with a high work function to allow holes be easily provided. The first electrode 11 may be a reflective electrode or a transmissive electrode. The material for the first electrode 11 may be an indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), or zinc oxide (ZnO). In some embodiments, the material for the first electrode 11 may be metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).
The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.
An organic layer 15 is disposed on the first electrode 11.
The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.
The hole transport region may be disposed between the first electrode 11 and the emission layer.
The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.
The hole transport region may include only either a hole injection layer or a hole transport layer. According to another embodiment, the hole transport region may have a structure of hole injection layer/hole transport layer or hole injection layer/hole transport layer/electron blocking layer, which are sequentially stacked in this stated order in the direction from the first electrode 11.
When the hole transport region includes a hole injection layer (HIL), the hole injection layer may be formed on the first electrode 11 by using any one of various methods, for example, vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.
When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a material that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100 to about 500° C., a vacuum pressure of about 10−8 to about 10−3 torr, and a deposition rate of about 0.01 to about 100 Å/sec. However, the deposition conditions are not limited thereto.
When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.
Conditions for a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.
The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated NPB, TAPC, HMTPD, 4,4′,4′′-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:













Ar101 and Ar102 in Formula 201 may be each independently selected from
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group; and
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one of a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group.
xa and xb in Formula 201 may be each independently an integer of 0 to 5, or 0, 1 or 2. For example, xa may be 1 and xb may be 0, but xa and xb are not limited thereto.
R101 to R108, R111 to R119, and R121 to R124 in Formulae 201 and 202 may be each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, and so on), and a C1-C10 alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and so on);
a C1-C10 alkyl group and a C1-C10 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and
a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10 alkyl group, or a C1-C10 alkoxy group, but they are not limited thereto.
R109 in Formula 201 may be selected from
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; or
a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group.
According to an embodiment, the compound represented by Formula 201 may be represented by Formula 201A below, but is not limited thereto:




R101, R111, R112, and R109 in Formula 201A may be understood by referring to the description provided herein.
For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include compounds HT1 to HT20 illustrated below, but are not limited thereto.






















A thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes both a hole injection layer and a hole transport layer, a thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.
The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.
The charge-generation material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but is not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenium oxide; and a cyano group-containing compound, such as Compound HT-D1 below, but are not limited thereto.




The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.
Then, an emission layer (EML) may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied to form the hole injection layer although the deposition or coating conditions may vary according to the material that is used to form the emission layer.
When the organic light-emitting device is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. According to another embodiment, due to a stacking structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.
The emission layer may include at least one condensed cyclic compound represented by one of Formulae 1A to 1C. The emission layer may include a dopant. The dopant may be at least one selected from a phosphorescent dopant and a fluorescent dopant.
The emission layer includes a host and a dopant, and the host may include at least one condensed cyclic compound represented by one of Formulae 1A to 1C.
According to an embodiment, the emission layer includes a first host and a second host.
The condensed cyclic compound represented by one of Formulae 1A to 1C may be included in the emission layer.
The first host may include the condensed cyclic compound represented by one of Formulae 1A to 1C, and the second host may include at least one selected from a first compound represented by Formula 41 and a second compound represented by Formula 61:




wherein in the formulae above,
X41 is N-[(L42)a42-(R42)b42], S, O, S(═O), S(═O)2, C(═O), C(R43)(R44), Si(R43)(R44), P(R43), P(═O)(R43), or C═N(R43);
Ring A61 in Formula 61 is represented by Formula 61A;
Ring A62 in Formula 61 is represented by Formula 61B;
X61 is N-[(L62)a62-(R62)b62], S, O, S(═O), S(═O)2, C(═O), C(R63)(R64), Si(R63)(R64), P(R63), P(═O)(R63), or C═N(R63);
X71 is C(R71) or N;
X72 is C(R72) or N;
X73 is C(R73) or N;
X74 is C(R74) or N;
X75 is C(R75) or N;
X76 is C(R76) or N;
X77 is C(R77) or N;
X78 is C(R78) or N;
Ar41, L41, L42, L61, and L62 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed hetero-polycyclic group;
n1 and n2 are each independently an integer selected from 0 to 3;
a41, a42, a61, and a62 are each independently an integer selected from 0 to 3;
R41 to R44, R51 to R54, R61 to R64, and R71 to R79 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7);
b41, b42, b51 to b54, b61, b62, and b79 are each independently an integer selected from 1 to 3;
at least one of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37);
wherein Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 may be each independently selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.
According to an embodiment, R41 to R44, R51 to R54, R61 to R64, and R71 to R79 may be each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl, an acridinyl, a phenanthrolinyl, a phenazinyl, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, or an imidazopyrimidinyl group, each substituted with at least one selected from a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl, an acridinyl, a phenanthrolinyl, a phenazinyl, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group; and
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, —Si(Q33)(Q34)(Q35), a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and a biphenyl group; and
—Si(Q3)(Q4)(Q5),
wherein Q3 to Q5 and Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group, but are not limited thereto.
For example, the first compound may be represented by one of Formulae 41-1 to 41-12 below, and the second compound may be represented by one of Formulae 61-1 to 61-6:













X41, X61, L41, L42, a41, a42, L61, L62, a61, a62, R41 to R44, b41, b42, R61 to R64, b61, b62, R71 to, R76 and b79 in Formulae 41-1 to 41-12 and 61-1 to 61-6 are as described above.
For example, when the second host includes the first compound represented by Formula 41, at least one selected from R41, R42, and R52 of the first compound, and when the second host includes the second compound represented by Formula 61, at least one selected from R61 and R62 of the second compound may be each independently selected from
a thiophenyl group, a furanyl group, a carbazolyl group, an acridinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group; and
a thiophenyl group, a furanyl group, a carbazolyl group, acridinyl, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group. and an ovalenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid or a salt thereof, sulfonic acid or a salt thereof, phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a phenyl group substituted with C1-C20 alkyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35),
wherein Q33 to Q35 may be each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.
In some embodiments, when the second host includes the first compound represented by Formula 41, at least one selected from R41, R42, and R52 of the first compound, and when the second host includes the second compound represented by Formula 61, at least one selected from R61 and R62 of the second compound may be represented by one of Formulae 5-1 to 5-6 and 6-1 to 6-5.
According to an embodiment, the first compound represented by Formula 41 may include one of Compounds A1 to A83 below, and the second compound represented by Formula 61 may include one of Compounds B1 to B20, but they are not limited thereto:
























































































When the first host and the second host all are included in an emission layer, holes and electrons provided to the emission layer may be effectively controlled. Accordingly, an organic light-emitting device with high luminescent efficiency and long lifespan may be obtained.
A weight ratio of the first host to the second host in the emission layer may be each independently in a range of 1:99 to 99:1, for example, 10:90 to 90:10. When the weight ratio of the first host and the second host is within these ranges, holes and electrons provided to the emission layer may be effectively controlled.
A dopant in the emission layer may be a fluorescent dopant that emits light according to a fluorescent emission mechanism or a phosphorescent dopant that emits light according to a phosphorescent emission mechanism.
According to an embodiment, the dopant in the emission layer may be a phosphorescent dopant, and the phosphorescent dopant may include an organometallic compound represented by Formula 81 below:




wherein in Formula 81,
M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm);
Y1 to Y4 are each independently carbon (C) or nitrogen (N);
Y1 and Y2 are linked via a single bond or a double bond, and Y3 and Y4 are linked via a single bond or a double bond;
CY1 and CY2 are each independently selected from a benzene, a naphthalene, a fluorene, a spiro-fluorene, an indene, a pyrrole, a thiophene, a furan, an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isooxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, a quinoline, an isoquinoline, a benzoquinoline, a quinoxaline, a quinazoline, a carbazole, a benzoimidazole, a benzofuran, a benzothiophene, an isobenzothiophene, a benzooxazole, an isobenzooxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a dibenzofuran, and a dibenzothiophene, and CY1 and CY2 are optionally linked to each other through a single bond or an organic linking group;
R81 to R82 may be each independently a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, —SF5, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), or —B(Q6)(Q7);
a81 and a82 are each independently an integer of 1 to 5;
n81 is an integer of 0 to 4;
n82 is 1, 2, or 3; and
L81 is a monovalent organic ligand, a divalent organic ligand, or a trivalent organic ligand.
R81 and R82 may be understood by referring to the description provided herein in connection with R41.
The phosphorescent dopant may include at least one of Compounds PD1 to PD78 below, but is not limited thereto:














































According to another embodiment, the phosphorescent dopant may include PtOEP illustrated below:




The fluorescent dopant may include at least one selected from DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and C545T.




When the emission layer includes a host and a dopant, an amount of the dopant may be in a range of about 0.01 to about 20 parts by weight based on 100 parts by weight of the host, but is not limited thereto.
A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.
Then, an electron transport region may be disposed on the emission layer.
The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.
For example, the electron transport region may have a structure of hole blocking layer/electron transport layer/electron injection layer or a structure of electron transport layer/electron injection layer, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layer structure including two or more different materials.
Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.
When the electron transport layer includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP and Bphen, but may also include other materials.




A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have excellent hole blocking characteristics without a substantial increase in driving voltage.
The electron transport layer may further include, in addition to the organometallic compound represented by Formula 1, at least one selected from BCP, Bphen, Alq3, Balq, TAZ, and NTAZ.




According to another embodiment, the electron transport layer may include at least one of ET1 and ET2, but are not limited thereto:




A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.
Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.
The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2.




The electron transport region may include an electron injection layer (EIL) that allows electrons to be easily provided from a second electrode 19.
The electron injection layer may include at least one selected from, LiF, NaCl, CsF, Li2O, BaO, and LiQ.
A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.
The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the second electrode 19. To manufacture a top emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinbefore, the organic light-emitting device has been described with reference to FIG. 1, but is not limited thereto.
A C1-C60 alkyl group used herein refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Detailed examples thereof are a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. A C1-C60 alkylene group used herein refers to a divalent group having the same structure as the C1-C60 alkyl group.
A C1-C60 alkoxy group used herein refers to a monovalent group represented by —OA101 (wherein A101 is the C1-C60 alkyl group). Detailed examples thereof are a methoxy group, an ethoxy group, and an isopropyloxy group.
A C2-C60 alkenyl group used herein refers to a hydrocarbon group formed by substituting at least one carbon double bond in the middle or at the terminal of the C2-C60 alkyl group. Detailed examples thereof are an ethenyl group, a propenyl group, and a butenyl group. A C2-C60 alkenylene group used herein refers to a divalent group having the same structure as the C2-C60 alkenyl group.
A C2-C60 alkynyl group used herein refers to a hydrocarbon group formed by substituting at least one carbon triple bond in the middle or at the terminal of the C2-C60 alkyl group. Detailed examples thereof are an ethynyl group, and a propynyl group. A C2-C60 alkynylene group used herein refers to a divalent group having the same structure as the C2-C60 alkynyl group.
A C3-C10 cycloalkyl group used herein refers to a monovalent hydrocarbon monocyclic group having 3 to 10 carbon atoms. Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C3-C10 cycloalkylene group used herein refers to a divalent group having the same structure as the C3-C10 cycloalkyl group.
A C2-C10 heterocycloalkyl group used herein refers to a monovalent monocyclic group having at least one hetero atom selected from N, O, P, and S as a ring-forming atom and 2 to 10 carbon atoms. Detailed examples thereof are a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. A C2-C10 heterocycloalkylene group used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkyl group.
A C3-C10 cycloalkenyl group used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one double bond in the ring thereof and does not have aromaticity. Detailed examples thereof are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. A C3-C10 cycloalkenylene group used herein refers to a divalent group having the same structure as the C3-C10 cycloalkenyl group.
A C2-C10 heterocycloalkenyl group used herein refers to a monovalent monocyclic group that has at least one hetero atom selected from N, O, P, and S as a ring-forming atom, 2 to 10 carbon atoms, and at least one double bond in its ring. Detailed examples of the C2-C10 heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. A C2-C10 heterocycloalkenylene group used herein refers to a divalent group having the same structure as the C2-C10 heterocycloalkenyl group.
A C6-C60 aryl group used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C6-C60 arylene group used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Detailed examples of the C6-C60 aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60 aryl group and the C6-C60 arylene group each include two or more rings, the rings may be fused to each other.
A C2-C60 heteroaryl group used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and 2 to 60 carbon atoms. A C2-C60 heteroarylene group used herein refers to a divalent group having a carbocyclic aromatic system that has at least one hetero atom selected from N, O, P, and S as a ring-forming atom, and 2 to 60 carbon atoms. Examples of the C2-C60 heteroaryl group are a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C2-C60 heteroaryl group and the C2-C60 heteroarylene group each include two or more rings, the rings may be fused to each other.
A C6-C60 aryloxy group used herein indicates —OA102 (wherein A102 is the C6-C60 aryl group), and a C6-C60 arylthio group indicates —SA103 (wherein A103 is the C6-C60 aryl group).
A monovalent non-aromatic condensed polycyclic group used herein refers to a monovalent group that has two or more rings condensed to each other, only carbon atoms (for example, the number of carbon atoms may be in a range of 8 to 60) as ring forming atoms, wherein the molecular structure as a whole is non-aromatic in the entire molecular structure. An example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. A divalent non-aromatic condensed polycyclic group used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.
A monovalent non-aromatic condensed hetero-polycyclic group used herein refers to a monovalent group that has two or more rings condensed to each other, has a heteroatom selected from N, O P, and S, other than carbon atoms (for example, the number of carbon atoms may be in a range of 2 to 60), as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic in the entire molecular structure. An example of the monovalent non-aromatic condensed hetero-polycyclic group is a carbazolyl group. A divalent non-aromatic condensed hetero-polycyclic group used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed hetero-polycyclic group.
In the present specification, at least one of substituents of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C2-C60 alkynylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37), wherein
Q1 to Q7, Q11 to Q17, and Q31 to Q37 used herein may be each independently selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group.
In the present specification, at least one of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C2-C60 alkynylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, substituted monovalent non-aromatic condensed polycyclic group, and substituted monovalent non-aromatic condensed hetero-polycyclic group may be selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q16), and —B(Q16)(Q17);
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one selected from a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic hetero-condensed polycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37),
wherein Q1 to Q7, Q11 to Q17, and Q31 to Q37 may be each independently a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthrenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a furanyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isooxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, and an imidazopyridinyl group, each substituted with at least one selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, or a quinazolinyl group, but they are not limited thereto.
The term “biphenyl group” as used therein refers to “a phenyl group substituted with a phenyl group.”
Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that a molar equivalent of A was identical to a molar equivalent of B.
EXAMPLES
Synthesis Example 1: Synthesis of Compound 3







Synthesis of Intermediate 3-5
Intermediate 3-6 (10 g, 59.8 mmol) and Intermediate A (8.44 g, 59.8 mmol) were dissolved in 200 mL of DMSO, and then, Cs2CO3 (23.4 g, 71.8 mmol) was added to the resultant and stirred for 15 hours. 500 mL of water was added to the reaction product, and the resultant was filtered and a solid was collected. The solid was dissolved in 300 mL of methylene chloride, and 300 mL of water was added thereto, and then the resultant was extracted. An organic layer obtained therefrom was dried by using MgSO4, and the residual obtained by evaporating the solvent was separation-purified by silica gel column chromatography to obtain Intermediate 3-5 (12.93 g, yield of 75%). The obtained compound was identified by LC-MS.
C18H12N2O2: M+ 288.09
Synthesis of Intermediate 3-4
Intermediate 3-5 (10 g, 34.7 mmol) and SnCl2.2H2O (25.16 g, 111 mmol) was added to EtOH and then, the mixture was heated to 70° C. for 8 hours or more. When the reaction stopped, the reaction product was cooled to room temperature, and then, concentrated, and an organic layer obtained by adding 300 mL of methylene chloride and 300 mL of NaHCO3 (aq) thereto was dried by using MgSO4, and the residual obtained by evaporating the solvent was separation-purified by silica gel column chromatography to obtain Intermediate 3-4 (6.27 g, yield of 70%). The obtained compound was identified by LC-MS.
C18H14N2: M+ 258.12
Synthesis of Intermediate 3-3
Intermediate 3-4 (6 g, 23.23 mmol), 60 mL of acetic acid, 5 mL of conc. H2SO4 in a reaction container were deposited to an ice bath to decrease the temperature to 10° C. Then, NaNO2 (1.6 g, 1 eq) was dissolved in 150 mL of water, and the resultant was added dropwise thereto for 20 minutes, and stirred for 10 minutes, and then, the temperature of the mixture was raised to 130° C., and then stirred for 20 minutes. When the reaction stopped, the temperature was decreased to room temperature, and then, 300 mL of water was added thereto, and filtered to isolate a precipitated solid. The residual was separation-purified by silica gel column chromatography to obtain Intermediate 3-3 (4.03 g, 72%). The obtained compound was identified by LC-MS.
C18H11N: M+ 241.09
Synthesis of Intermediate 3-2
Intermediate 3-3 (3 g, 12.43 mmol) and NBS (2.21 g, 12.43 mmol) were dissolved in 100 mL of methylene chloride, and then, the mixture was stirred at room temperature for 15 hours. When the reaction stopped, the reaction product was cooled to room temperature, and 200 mL of methylene chloride was added thereto, and then 200 mL of water was added dropwise thereto, and an obtained organic layer was dried by using MgSO4, and the residual obtained by evaporating the solvent was separation-purified by silica gel column chromatography to obtain Intermediate 3-2 (2.03 g, 51%). The obtained compound was identified by LC-MS.
C18H10BrN: M+ 319.00
Synthesis of Intermediate 3-1
Intermediate 3-2 (1.5 g, 4.68 mmol), Intermediate B (1.19 g, 5.62 mmol), Pd(PPh3)4 (0.27 g, 0.234 mmol), and K2CO3 (3.24 g, 23.4 mmol) were mixed with 100 mL of THF and 30 mL of distilled water. The mixture was heated to a temperature of 120° C. and stirred for 24 hours while refluxing, and then, cooled to room temperature, and extracted using 200 mL of water and 200 mL of methylene chloride. An organic layer obtained therefrom was dried by using MgSO4, and the residual obtained by evaporating the solvent was separation-purified by silica gel column chromatography to obtain Intermediate 3-1 (1.5 g, 79%). The obtained compound was identified by LC-MS.
C30H18N2: M+ 406.15
Synthesis of Compound 3
Intermediate 3-1 (1 g, 2.46 mmol) was dissolved in 30 mL of DMF, and then, sodium hydride was added thereto, and the result was stirred for 1 hour. Intermediate C (0.8 g, 2.95 mmol) dissolved in 10 mL of DMF was added thereto, and then, stirred for 12 hours at room temperature. Resulting precipitate was washed with methylene chloride, and then added to dichlorobenzene, and the result was heated, and then, while cooling to room temperature, recrystallized and separated to obtain Compound 3 (1.14 g, 65%). The obtained compound was identified by LC-MS and NMR.
C51H31N5: M+ 713.26
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.36-8.19 (m, 11H), 7.89 (s, 1H), 7.68-7.50 (m, 16H), 7.20 (m, 3H)
Synthesis Example 2: Synthesis of Compound 2




Compound 2 (68%) was synthesized in the same manner as in Synthesis Example 1, except that in synthesizing Compound 3, Intermediate D was used instead of Intermediate C. The obtained compound was identified by LC-MS and NMR.
C45H27N5: M+ 637.75
1H NMR (CDCl3, 300 MHz) δ (ppm) 7.36-8.30 (m, 5H), 8.19-8.13 (m, 4H), 7.89 (s, 1H), 7.65-7.50 (m, 14H), 7.20 (m, 3H)
Synthesis Example 3: Synthesis of Compound 4




Compound 4 (70%) was synthesized in the same manner as in Synthesis Example 1, except that in synthesizing Compound 3, Intermediate E was used instead of Intermediate C. The obtained compound was identified by LC-MS and NMR.
C46H28N4: M+ 636.23
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.9 (s, 1H), 8.30-8.13 (m, 5H), 7.94-7.89 (m, 5H), 7.65-7.50 (m, 14H), 7.20 (m, 3H)
Synthesis Example 4: Synthesis of Compound 7




Compound 7 (62%) was synthesized in the same manner as in Synthesis Example 1, except that in synthesizing Compound 3, Intermediate F was used instead of Intermediate C. The obtained compound was identified by LC-MS and NMR.
C44H26N4: M+ 610.22
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.30-8.13 (m, 6H), 7.89-7.80 (m, 5H), 7.65-7.50 (m, 12H), 7.20 (m, 3H)
Synthesis Example 5: Synthesis of Compound 8




Compound 8 (62%) was synthesized in the same manner as in Synthesis Example 1, except that in synthesizing Compound 3, Intermediate G was used instead of Intermediate C. The obtained compound was identified by LC-MS and NMR.
C50H30N4: M+ 686.25
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.30-8.13 (m, 8H), 7.89-7.75 (m, 7H), 7.65-7.41 (m, 12H), 7.20 (m, 3H)
Synthesis Example 6: Synthesis of Compound 76




Synthesis of Intermediate 76-1
Intermediate 76-1 was prepared in the same manner as used in synthesizing Intermediate 3-1 of Synthesis Example 1, except that Intermediate 76-2 and Intermediate 76-3 were respectively used instead of Intermediate 3-2 and Intermediate B.
Synthesis of Compound 76
Compound 76 (yield of 74%) was prepared in the same manner as used in synthesizing Intermediate 3 of Synthesis Example 1, except that in synthesizing Compound 3, Intermediate 76-1 and Intermediate D were respectively used instead of Intermediate 3-1 and Intermediate C. The obtained compound was identified by LC-MS and NMR.
C45H27N5: M+ 686.25
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.62 (d, 1H), 8.36 (m, 4H), 8.22-8.19 (m, 4H), 7.74 (s, 1H), 7.65-7.50 (m, 14H), 7.20 (m, 3H)
Synthesis Example 7: Synthesis of Compound 60




Synthesis of Intermediate 60-2
Intermediate 60-2 was synthesized in the same manner as in synthesizing Intermediate 3-2 of Synthesis Example 1, except that Intermediate 60-3 was used instead of Intermediate 3-3.
Synthesis of Intermediate 60-1
Intermediate 60-1 was prepared in the same manner as used in synthesizing Intermediate 3-1 of Synthesis Example 1, except that Intermediate 60-2 and Intermediate H were respectively used instead of Intermediate 3-2 and Intermediate B.
Synthesis of Compound 60
Compound 60 (yield of 51%) was prepared in the same manner as used in synthesizing Intermediate 3 of Synthesis Example 1, except that Intermediate 60-1 and Intermediate I were respectively used instead of Intermediate 3-1 and Intermediate C.
C38H22N4: M+ 534.18
1H NMR (CDCl3, 300 MHz) δ (ppm) 8.87 (d, 1H), 8.51-8.01 (m, 8H), 7.89 (s, 1H), 7.70-7.43 (m, 8H), 7.20-7.15 (m, 4H)
Evaluation Example 1: Evaluation on HOMO, LUMO, and Triplets (T1) Energy Levels
HOMO, LUMO and T1 energy levels of Compounds 2, 3, and 7 were evaluated according to the method indicated in Table 2, and results thereof are shown in Table 3.








TABLE 2







HOMO energy level
A potential (V)-current (A) graph of each compound was obtained by using cyclic


evaluation method
voltammetry (CV) (electrolyte: 0.1M Bu4NClO4/solvent: CH2Cl2/electrode: 3 electrode



system (working electrode: GC, reference electrode: Ag/AgCl, auxiliary electrode: Pt)), and



then, from reduction onset of the graph, a HOMO energy level of the compound was



calculated.


LUMO energy level
Each compound was diluted at a concentration of 1 × 10−5 M in CHCl3, and an UV absorption


evaluation method
spectrum thereof was measured at room temperature by using a Shimadzu UV-350



spectrometer, and a LUMO energy level thereof was calculated by using an optical band



gap (Eg) from an edge of the absorption spectrum.


T1 energy level
A mixture (each compound was dissolved in an amount of 1 mg in 3 cc of toluene) of


evaluation method
toluene and each compound was loaded into a quartz cell, and then, the resultant quartz



cell was loaded into liquid nitrogen (77 K) and a photoluminescence spectrum thereof was



measured by using a device for measuring photoluminescence, and the obtained spectrum



was compared with a photoluminescence spectrum measured at room temperature, and



peaks observed only at low temperature were analyzed to calculate T1 energy levels.



















TABLE 3






HOMO (eV)
LUMO (eV)



Compound No.
(calc.)
(calc.)
T1 energy level (eV)


















2
−5.515
−2.376
2.63


3
−5.303
−2.298
2.66


7
−5.587
−2.385
2.47









From Table 3, it is confirmed that the compounds above have electric characteristics that are suitable for use as a material for forming an organic light-emitting device.
Evaluation Example 2: Thermal Characteristics Evaluation
Thermal analysis (N2 atmosphere, temperature range: from room temperature to 800° C. (10° C./min)-TGA, from room temperature to 400° C.-DSC, Pan Type: Pt Pan in disposable Al Pan (TGA), and disposable Al pan (DSC)) was performed on Compounds 7 and 8 and Compounds C and D by using thermo gravimetric analysis (TGA) and differential scanning calorimetry (DSC), and results thereof are shown in Table 4. As shown in Table 4, it was confirmed that the synthesized compounds had excellent thermal stability.










TABLE 4





Compound No.
Tg (° C.)
Td (1%, ° C.)
Td (5%, ° C.)


















Compound 7
149.45
447.8
486.4


Compound 8
167.33
482.5
521.5


Compound C
128.8
427.3
473.9


Compound D
144.2
462.5
502.1
















Example 1
A glass substrate with ITO/Ag/ITO (70/1,000/70 Å) anode thereon was cut to a size of 50 mm×50 mm×0.5 mm, and then, ultrasonically cleaned with isopropyl alcohol, acetone, and pure water for 5 minutes each, and then exposed to ultraviolet (UV) light for 30 minutes and then ozone. Then, the glass substrate was loaded into a vacuum deposition apparatus.
2-TNATA was deposited on the anode on the glass substrate to form a hole injection layer having a thickness of 600 Å, and then NPB was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,000 Å to form a hole transport region.
Subsequently, Compound 3 (host) and Ir(ppy)3 (dopant, referred to as Compound PD1 in this application) were co-deposited on the hole transport layer were co-deposited at a weight ratio of 91:9 to form an emission layer having a thickness of 250 Å.
BCP was deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å, and Alq3 was deposited on the hole blocking layer to form an electron transport layer having a thickness of 350 Å, and LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å to form an electron transport region.
Mg and Ag were deposited on the electron injection layer at a weight ratio of 90:10 to form a cathode having a thickness of 120 Å, thereby completing the manufacture of an organic light-emitting device.
Example 2
An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming an emission layer, as a host, Compound 2 was used instead of Compound 3.
Example 3
An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming an emission layer, as a host, Compound 4 was used instead of Compound 3.
Example 4
An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming an emission layer, as a host, Compound 76 was used instead of Compound 3.
Example 5
An organic light-emitting device was manufactured in the same manner as in Example 1, except that a thickness of the hole transport layer was 1,350 Å, and in forming an emission layer, Compound 7 was used as the host, PtOEP was used as the dopant, and a thickness of the emission layer was 400 Å.
Example 6
An organic light-emitting device was manufactured in the same manner as in Example 4, except that in forming an emission layer, as a host, Compound 8 was used instead of Compound 7.
Comparative Example 1
An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming an emission layer, as a host, Compound A was used instead of Compound 3.




Comparative Example 2
An organic light-emitting device was manufactured in the same manner as in Example 1, except that in forming an emission layer, as a host, Compound B was used instead of Compound 3.




Comparative Example 3
An organic light-emitting device was manufactured in the same manner as in Example 5, except that in forming an emission layer, as a host, Compound A was used instead of Compound 7.
Comparative Example 3
An organic light-emitting device was manufactured in the same manner as in Example 5, except that in forming an emission layer, as a host, Compound B was used instead of Compound 7.
Evaluation Example 4: Evaluation on Characteristics of an Organic Light-Emitting Device
Driving voltage, current density, brightness, luminescence color, efficiency, and LT97 (@10 milliamperes per square centimeter, mA/cm2) of the organic light-emitting devices of Examples 1 to 6 and Comparative Examples 1 to 4 were evaluated by using PR650 Spectroscan Source Measurement Unit. (a product of PhotoResearch Company). Results thereof are shown in Table 6 below.














TABLE 6










Driving
Current






EML
Voltage
Density
Brightness
Efficiency
Emission
















Host
Dopant
(V)
(mA/cm2)
(cd/m2)
(cd/A)
color
LT97 (hr)



















Example 1
Compound 3
Ir(ppy)3
5.4
10
6,829
68.3
Green
75


Example 2
Compound 2
Ir(ppy)3
5.3
10
6,724
67.2
Green
79


Example 3
Compound 4
Ir(ppy)3
5.9
10
6,709
67.1
Green
76


Example 4
Compound 76
Ir(ppy)3
5.6
10
6,171
61.7
Green
70


Example 5
Compound 7
PtOEP
5.8
10
3,422
34.2
Red
110


Example 6
Compound 8
PtOEP
6.0
10
3,117
31.2
Red
114


Comparative
Compound A
Ir(ppy)3
8.2
10
4,564
45.6
Green
32


Example 1


Comparative
Compound B
Ir(ppy)3
7.3
10
4,276
42.8
Green
35


Example 2


Comparative
Compound A
PtOEP
7.9
10
1,810
18.1
Red
52


Example 3


Comparative
Compound B
PtOEP
7.7
10
1,921
19.2
Red
50


Example 4









From Table 6, it was confirmed that the organic light-emitting devices of Examples 1 to 4 had lower driving voltage, higher efficiency, and longer lifespan of the organic light-emitting devices of Comparative Examples 1 and 2, and the organic light-emitting devices of Examples 5 and 6 had lower driving voltage, higher efficiency, and longer lifespan than the organic light-emitting devices of Comparative Examples 3 and 4.
The condensed cyclic compounds according to embodiments have excellent electric characteristics and thermal stability. Accordingly, organic light-emitting devices including the condensed cyclic compounds may have a low driving voltage, high efficiency, high brightness, and a long lifespan.
It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments.

## Claims

1. A condensed cyclic compound represented by one of Formulae 1A to 1C:






wherein in the Formulae 1A to 1C and 2A to 2F,
Ring A is selected from a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, a group represented by Formula 2A, and a group represented by Formula 2B;
Ring B1 is a C5-C20 carbocyclic group or a C2-C20 heterocyclic group that does not comprise a nitrogen atom as a ring-forming atom;
Ring B2, Ring B3, Ring C1, and Ring C2 are each independently a C5-C20 carbocyclic group, or a C2-C20 heterocyclic group, provided that at least one selected from Ring B2 and Ring B3 is a C2-C20 heterocyclic group comprising a nitrogen atom as a ring-forming atom, and at least one selected from Ring C1 and Ring C2 is a C2-C20 heterocyclic group comprising a nitrogen atom as a ring-forming atom;
Pc1 and Pc2 in Formula 1A and 1B are each independently a group represented by Formulae 2A or a group represented by Formula 2B;
Cz1, Cz2, and Cz3 in Formula 1C are each independently selected from a group represented by Formula 2C, a group represented by Formula 2D, a group represented by Formula 2E, and a group represented by Formula 2F;
c1, c2, c11, c12, c13, p1, p2, p11, p12, and p13 are each independently an integer selected from 0 to 3;
when c1 and c2 in Formula 1A and 1B both are 0, Ring A is a group represented by Formula 2A or a group represented by Formula 2B;
when Ring A in Formula 1A and 1B is neither a group represented by Formula 2A nor a group represented by Formula 2B, c1+c2≠0;
at least one selected from Ring A in Formula 1A, all R1 in Formula 1A, and all R2 in Formula 1A is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each comprising at least one Moiety 1 as a ring-forming moiety;
the sum of c11, c12, and c13 in Formula 1C is not 0;
when each of Cz1, Cz2, and Cz3 in Formula 1C is independently a group represented by Formula 2C or a group represented by Formula 2D, p11+p12+p13≠0 and at least one selected from all R11 in Formula 1C, all R12 in Formula 1C, and all R13 in Formula 1C is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each comprising at least one Moiety 1 as a ring-forming moiety;
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently selected from a substituted or unsubstituted C1-C60 alkylene group, a substituted or unsubstituted C2-C60 alkenylene group, a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed hetero-polycyclic group;
a1 to a3, a11 to a13, a21 to a24, and a31 to a33 are each independently an integer selected from 0 to 6;
R1, R2, R11 to R13, R21 to R23, and R31 to R33 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7);
b1, b2, b11 to b13, b21 to b23, and b31 to b33 are each independently an integer selected from 1 to 4;
at least one of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed hetero-polycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37);
wherein Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are each independently selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group:


**═N—***  Moiety 1


wherein in Moiety 1, ** and *** each indicates a binding site to a ring-forming atom included in a ring comprising Moiety 1.

2. The condensed cyclic compound of claim 1, wherein
Ring A in Formula 1A is selected from
a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyrimidinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group, a benzothienopyridinyl group, a group represented by Formula 2A, and a group represented by Formula 2B; and
a phenyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, phenanthridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzofuropyrazinyl group, a benzofuropyrimidinyl group, a benzofuropyridinyl group, a benzothienopyrazinyl group, a benzothienopyrimidinyl group, and a benzothienopyridinyl group, each substituted with one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a phenyl group substituted with a C1-C20 alkyl group, a naphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35),
wherein Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.

3. The condensed cyclic compound of claim 1, wherein
Ring A in Formula 1A is represented by one selected from Formulae 4-1 to 4-51, Formulae 6-1 to 6-5, a group represented Formula 2A, and a group represented by Formula 2B:
















wherein in Formulae 4-1 to 4-51 and 6-1 to 6-5:
Y31 is O, S, C(Z33)(Z34), N(Z35), or Si(Z36)(Z37);
Z31 to Z37 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group substituted with a C1-C20 alkyl group, a phenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35), wherein
Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;
e1 is an integer of 1 to 5;
e2 is an integer of 1 to 7;
e3 is an integer of 1 to 3;
e4 is an integer of 1 to 4;
e5 is an integer of 1 or 2;
e6 is an integer of 1 to 6; and
* indicates a binding site to a neighboring atom.

4. The condensed cyclic compound of claim 1, wherein
Ring B1 is a benzene, a naphthalene, an anthracene, a phenanthrene, a benzofuran, or a benzothiophene.

5. The condensed cyclic compound of claim 1, wherein
Ring B2, Ring B3, Ring C1, and Ring C2 are each independently a benzene, a naphthalene, an anthracene, a phenanthrene, a benzofuran, a benzothiophene, a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine;
at least one selected from Ring B2 and Ring B3 is a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, a benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine; and
at least one selected from Ring C1 and Ring C2 is a pyridine, a pyrimidine, a pyrazine, a benzofuropyrazine, a benzofuropyrimidine, a benzofuropyridine, a benzothienopyrazine, a benzothienopyrimidine, or a benzothienopyridine.

6. The condensed cyclic compound of claim 1, wherein
c1=0, c2=0, and Ring A is a group represented by Formula 2A or a group represented by Formula 2B;
c1=1 and c2=0;
c1=1, and c2=1;
c11=1, c12=0, and c13=0;
c11=0, c12=0, and c13=1;
c11=1, c12=1, and c13=0; or
c11=1, c12=0, and c13=1.

7. The condensed cyclic compound of claim 1, wherein
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently selected from
a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, an imidazopyrimidinylene group, and an imidazopyridinylene group; and
a phenylene group, a pentalenylene group, an indenylene group, naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pyrrolylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzooxazolylene group, a benzoimidazolylene group, a furanylene group, a benzofuranylene group, a thiophenylene group, a benzothiophenylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group an imidazopyrimidinylene group, or an imidazopyridinylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a C6-C20 aryl group, a C2-C20 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, and —Si(Q33)(Q34)(Q35),
wherein Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group.

8. The condensed cyclic compound of claim 1, wherein
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently represented by one of Formulae 2-1 to 2-37:













wherein in Formulae 2-1 to 2-37,
Y1 may be O, S, S(═O), S(═O)2, C(Z3)(Z4), N(Z5), or Si(Z6)(Z7);
Z1 to Z7 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35), wherein
Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, and a quinazolinyl group;
d1 is an integer of 1 to 4;
d2 is an integer of 1 to 3;
d3 is an integer of 1 to 6;
d4 is an integer of 1 to 8;
d5 is an integer of 1 or 2;
d6 is an integer of 1 to 5; and
* indicates a binding site to a neighboring atom.

9. The condensed cyclic compound of claim 1, wherein
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently selected from
a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group; and
a phenylene group, naphthylene group, a phenanthrenylene group, an anthracenylene group, a triphenylenylene group, and a carbazolylene group each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a phenanthrenyl group, and a biphenyl group.

10. The condensed cyclic compound of claim 1, wherein
L1 to L3, L11 to L13, L21 to L24, and L31 to L33 are each independently represented by one of Formulae 3-1 to 3-33:
















wherein * and *′ in Formulae 3-1 to 3-33 each independently indicates a binding site to a neighboring atom.

11. The condensed cyclic compound of claim 1, wherein
a1 to a3, a11 to a13, a21 to a24, and a31 to a33 are each independently 0, 1, or 2.

12. The condensed cyclic compound of claim 1, wherein
R1, R2, R11 to R13, R21 to R23, and R31 to R33 are each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzooxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group;
a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, phenanthridinyl, acridinyl, phenanthrolinyl, phenazinyl, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a phenyl group substituted with a C1-C20 alkyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isooxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzooxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35); and
—Si(Q3)(Q4)(Q5),
wherein Q3 to Q5 and Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group.

13. The condensed cyclic compound of claim 1, wherein
R1, R2, R11 to R13, R21 to R23, and R31 to R33 are each independently selected from
a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, and a C1-C20 alkoxy group;
a C1-C20 alkyl group and a C1-C20 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, and a phosphoric acid or a salt thereof;
one of Formulae 4-1 to 4-51, 5-1 to 5-6, and 6-1 to 6-5; and
—Si(Q3)(Q4)(Q5),
wherein Q3 to Q5 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group:



















wherein in Formulae 4-1 to 4-51, 5-1 to 5-6, and 6-1 to 6-5,
Y31 is O, S, C(Z33)(Z34), N(Z35), or Si(Z36)(Z37);
Z31 to Z37 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group substituted with a C1-C20 alkyl group, a phenyl group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a quinoxalinyl group, a biphenyl group, and —Si(Q33)(Q34)(Q35), wherein
Q33 to Q35 are each independently selected from a hydrogen, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, and a quinoxalinyl group;
e1 is an integer of 1 to 5;
e2 is an integer of 1 to 7;
e3 is an integer of 1 to 3;
e4 is an integer of 1 to 4;
e5 is an integer of 1 or 2;
e6 is an integer of 1 to 6; and
* indicates a binding site to a neighboring atom.

14. The condensed cyclic compound of claim 1, wherein
Formula 2A is represented by one of Formulae 2A(1) to 2A(5), Formula 2B is represented by one of Formulae 2B(1) and 2B(2), Formula 2D is represented by one of Formulae 2D(1) to 2D(5), and Formula 2F is represented by one of Formulae 2F(1) and 2F(2):







wherein L21 to L24, a21 to a24, R21 to R23, b21 to b23, L31 to L33, a31 to a33, R31 to R33, b31 to b33, c21 to c23, c31, and c32 in Formulae 2A (1) to 2A (5), 2B(1), 2B(2), 2E(1) to 2E(5), 2F(1), and 2F(2) are the same as recited in claim 1.

15. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound is represented by one of Formulae 1A(1) to 1A(8):







wherein, in Formulae 1A(1) and 1A(8),
Ring A is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each comprising Moiety 1 as a ring-forming moiety;
Pc1, Pc2, L3, a3, R1, R2, p1, and p2 are the same as recited in claim 1; and
R3 and R4 are the same as recited in claim 1.

16. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound is represented by one selected from Formulae 1B(1) to 1B(10):







wherein Ring A, Pc1, Pc2, L3, a3, R1, R2, p1, and p2 in Formulae 1B(1) to 1B(10) are the same as recited in claim 1.

17. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound is represented by Formulae 1C(1) or 1C(2):




wherein Cz1, Cz2, Cz3, R11, R12, R13, p11, p12, and p13 in Formulae 1C(1) and 1C(2) are the same as recited in claim 1.

18. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound is represented by Formula 1C(3):




wherein in Formula 1C(3),
Cz3, L11, and all are the same as recited in claim 1;
R11 is a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C2-C60 heteroaryl group, or a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, each comprising Moiety 1 as a ring-forming moiety; and
b11 is 1 or 2.

19. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound represented by Formulae 1C(4) or 1C(5):




wherein in Formulae 1C (4) and 1C (5), Cz1 and Cz3 are each a group represented by Formula 2E or a group represented by Formula 2F.

20. The condensed cyclic compound of claim 1, wherein
the condensed cyclic compound is one of Compounds 1 to 76:

21. An organic light-emitting device comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
wherein the organic layer comprises an emission layer and at least one condensed cyclic compound represented by Formula 1 of claim 1.

22. The organic light-emitting device of claim 21, wherein
the emission layer comprises the condensed cyclic compound represented by Formula 1 of claim 1.

23. The organic light-emitting device of claim 21, wherein
the emission layer comprises a first host and a second host,
the condensed cyclic compound represented by one of Formulae 1A to 1C exists in the emission layer,
the first host comprises the condensed cyclic compound represented by one of Formulae 1A to 1C, and
the second host comprises at least one selected from a first compound represented by Formula 41 and a second compound represented by Formula 61:




wherein in the formulae 41, 61, 61A, and 61B,
X41 is N-[(L42)a42-(R42)b42], S, O, S(═O), S(═O)2, C(═O), C(R43)(R44), Si(R43)(R44), P(R43), P(═O)(R43), or C═N(R43);
Ring A61 in Formula 61 is represented by Formula 61A;
Ring A62 in Formula 61 is represented by Formula 61B;
X61 is N-[(L62)a62-(R62)b62], S, O, S(═O), S(═O)2, C(═O), C(R63)(R64), Si(R63)(R64), P(R63), P(═O)(R63), or C═N(R63);
X71 is C(R71) or N;
X72 is C(R72) or N;
X73 is C(R73) or N;
X74 is C(R74) or N;
X75 is C(R75) or N;
X76 is C(R76) or N;
X77 is C(R77) or N;
X78 is C(R78) or N;
Ar41, L41, L42, L61, and L62 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C2-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C2-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted and unsubstituted divalent non-aromatic condensed hetero-polycyclic group;
n1 and n2 are each independently an integer selected from 0 to 3;
a41, a42, a61, and a62 are each independently an integer selected from 0 to 3;
R41 to R43, R51 to R54, R61 to R64, and R71 to R79 are each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a substituted or unsubstituted C1-C60 alkyl group, a substituted or unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a substituted or unsubstituted C1-C60 alkoxy group, a substituted or unsubstituted C3-C10 cycloalkyl group, a substituted or unsubstituted C2-C10 heterocycloalkyl group, a substituted or unsubstituted C3-C10 cycloalkenyl group, a substituted or unsubstituted C2-C10 heterocycloalkenyl group, a substituted or unsubstituted C6-C60 aryl group, a substituted or unsubstituted C6-C60 aryloxy group, a substituted or unsubstituted C6-C60 arylthio group, a substituted or unsubstituted C2-C60 heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed hetero-polycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7);
b41, b42, b51 to b54, b61, b62, and b79 are each independently an integer selected from 1 to 3;
at least one of substituents of the substituted C1-C60 alkylene group, substituted C2-C60 alkenylene group, substituted C3-C10 cycloalkylene group, substituted C2-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C2-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, substituted divalent non-aromatic condensed polycyclic group, substituted divalent non-aromatic condensed hetero-polycyclic group, substituted C1-C60 alkyl group, substituted C2-C60 alkenyl group, substituted C2-C60 alkynyl group, substituted C1-C60 alkoxy group, substituted C3-C10 cycloalkyl group, substituted C2-C10 heterocycloalkyl group, substituted C3-C10 cycloalkenyl group, substituted C2-C10 heterocycloalkenyl group, substituted C6-C60 aryl group, substituted C6-C60 aryloxy group, substituted C6-C60 arylthio group, substituted C2-C60 heteroaryl group, a substituted monovalent non-aromatic condensed polycyclic group, and a substituted monovalent non-aromatic condensed hetero-polycyclic group is selected from
a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed hetero-polycyclic group, —N(Q11)(Q12), —Si(Q13)(Q14)(Q15), and —B(Q16)(Q17);
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed hetero-polycyclic group;
a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid or a salt thereof, a sulfonic acid or a salt thereof, a phosphoric acid or a salt thereof, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q21)(Q22), —Si(Q23)(Q24)(Q25), and —B(Q26)(Q27); and
—N(Q31)(Q32), —Si(Q33)(Q34)(Q35), and —B(Q36)(Q37);
wherein Q1 to Q7, Q11 to Q17, Q21 to Q27, and Q31 to Q37 are each independently selected from a hydrogen, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C2-C60 alkynyl group, a C1-C60 alkoxy group, a C3-C10 cycloalkyl group, a C2-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C2-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C2-C60 heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.

24. The organic light-emitting device of claim 21, wherein
the emission layer further comprises a phosphorescent dopant.

25. The organic light-emitting device of claim 21, wherein
the electron transport region comprises at least one of the condensed cyclic compounds represented by Formula 1.