# Patent

## Title
Pyrene-based compound and organic light-emitting device including the same

## Abstract

A pyrene-based compound is represented by Formula 1:




    
    
        where R11 to R14, L11, m11, n11, k11, a12, a13, and a14 are as defined in the specification.

## Background
CROSS-REFERENCE TO RELATED APPLICATION
Korean Patent Application No. 10-2013-0117585, filed on Oct. 1, 2013, in the Korean Intellectual Property Office, and entitled: “Pyrene-Based Compound And Organic Light-Emitting Device Including The Same,” is incorporated by reference herein in its entirety.
BACKGROUND
1. Field
One or more embodiments relate to a pyrene-based compound and an organic light-emitting device including the same.
2. Description of the Related Art
Organic light-emitting devices (OLEDs) are self-emitting devices that have advantages, such as wide viewing angles, excellent contrast, quick response, high brightness, and excellent driving voltage characteristics, and that can provide multicolored images.
An OLED may have a structure including a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially formed on the first electrode. Holes injected from the first electrode are transported to the emission layer through the hole transport region, and electrons injected from the second electrode are transported to the emission layer through the electron transport region. Carriers, such as the holes and electrons, recombine in the emission layer to generate excitons. When the excitons drop from an excited state to a ground state, light is emitted.
SUMMARY
Embodiments are directed to a pyrene-based compound represented by Formula 1:




wherein, in Formula 1,
L11 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, and a substituted or unsubstituted non-aromatic condensed polycycle;
at least one substituent of the substituted C3-C10 cycloalkylene group, substituted C1-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C1-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, and substituted non-aromatic condensed polycyclic group is selected from:
a deuterium atom, a halogen atom, 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 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
n11 is an integer of 0 to 3;
R11 is represented by one of Formulae 2-1 and 2-2;
k11 is an integer of 1 to 4;
R12 to R14 are each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, 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 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group(aryloxy), a C6-C60 arylthio group(arylthio), a C1-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C60 alkoxy group, a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
a12 is an integer of 1 to 5;
a13 and a14 are each independently an integer of 1 to 3;




wherein, in Formulae 2-1 and 2-2,
R21 to R27 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, 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 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group and a non-aromatic condensed polycyclic group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group and a non-aromatic condensed polycyclic group;
a22 to a27 are each independently an integer of 0 to 3;
b11 to b16 are each independently an integer of 0 to 2;
the sum of b11, b12, and b13 is 1 or greater, and the sum of b14, b15, and b16 is 1 or greater; and
* is a binding site with L11 or a pyrene ring in Formula 1.
Embodiments are also directed to an organic light-emitting device (OLED) that includes a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer, the organic layer including the pyrene-based compound.



BRIEF DESCRIPTION OF THE DRAWINGS
Features will become apparent to those of skill in the art by describing in detail exemplary embodiments with reference to the attached drawings in which:
FIG. 1 illustrates a schematic diagram depicting an organic light-emitting device (OLED) according to an embodiment.



DETAILED DESCRIPTION
Example embodiments will now be described more fully hereinafter with reference to the accompanying drawings; however, they may be embodied in different forms and should not be construed as limited to the embodiments set forth herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey exemplary implementations to those skilled in the art.
In the drawing figures, the dimensions of layers and regions may be exaggerated for clarity of illustration. It will also be understood that when a layer or element is referred to as being “on” another layer or substrate, it can be directly on the other layer or substrate, or intervening layers may also be present. Further, it will be understood that when a layer is referred to as being “under” another layer, it can be directly under, and one or more intervening layers may also be present. In addition, it will also be understood that when a layer is referred to as being “between” two layers, it can be the only layer between the two layers, or one or more intervening layers may also be present.
A pyrene-based compound is represented by Formula 1:




In Formula 1, L11 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, and a substituted or unsubstituted non-aromatic condensed polycyclic group;
at least one substituent of the substituted C3-C10 cycloalkylene group, substituted C1-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C1-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, and substituted non-aromatic condensed polycyclic group may be selected from
a deuterium atom, a halogen atom, 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, and a C1-C60 alkoxy group;
a C1-C60 alkyl group, a C2-7C60 alkenyl group, a C2-C60 alkynyl group, and a C1-C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.
According to an embodiment, in Formula 1, L11 may be selected from, for example,
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 benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene 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 pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thienylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene 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 benzoimidazolylene group, a benzofuranylene group, a benzothienylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolyene group, a dibenzocarbazolyene group, and a dibenzosilolylene group; and
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 benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene 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 pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a pyrrolylene group, a thienylene group, a furanylene group, a silolylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene 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 benzoimidazolylene group, a benzofuranylene group, a benzothienylene group, a benzosilolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolyene group, a dibenzocarbazolyene group, and a dibenzosilolylene group, each substituted with at least one of a deuterium atom, a halogen atom, 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 cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentyl group, a cyclohexenyl 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 thienyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl 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 benzothienyl group, a benzosilolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazole group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothienyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, and a dibenzosilolyl group.
According to another embodiment, in Formula 1, L11 may be represented by one of Formulae 3-1 to 3-32 below, as examples:













In Formulae 3-1 to 3-32,
Y1 is selected from C(Q31)(Q32), N(Q33), an oxygen atom, a sulfur atom, and Si(Q34)(Q35);
Q31 to Q35 are each independently selected from a hydrogen atom, a deuterium atom, a C1-C20 alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
Z1 and Z2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl 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
* and *′ represent a binding site with the pyrene ring, R11 or another L11.
According to another embodiment, in Formula 1, L11 may be represented by one of Formula 4-1 to 4-23 below, as examples:










where * and *′ represent a binding site with the pyrene ring, R11 or another L11.
In Formula 1, n11 denotes the number of L11, and n11 is an integer of 0, 1, 2, or 3. For example, in Formula 1, n11 may be an integer of 0 or 1. In Formula 1, when n11 is 0, -(L11)n11- denotes a single bond. When n11 is 2 or greater, a plurality of L11 s may be identical to or different from each other.
In Formula 1, R11 may be represented by one of Formulae 2-1 and 2-2:




In Formulae 2-1 and 2-2,
R21 to R27 are each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a22 to a27 are each independently an integer of 0 to 3;
b11 to b16 are each independently an integer of 0 to 2;
the sum of b11, b12, and b13 is 1 or greater, and the sum of b14, b15, and b16 is 1 or greater; and
* is a binding site with L11 or a pyrene ring in Formula 1.
In some embodiments, in Formula 1, R11 may be represented by one of Formulae 2-1a and 2-2a:




In Formulae 2-1a and 2-2a,
R21 to R27 are each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group and a C1-C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a22 to a27 are each independently an integer of 0 to 3;
b13 to b14 are each independently an integer of 1 or 2; and
* is a binding site with L11 or a pyrene ring in Formula 1.
In some embodiments, in Formula 1, R11 may be represented by Formula 2-1b:




In Formula 2-1 b,
R21 may be selected from:
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
* is a binding site with L11 or a pyrene ring in Formula 1.
For example, in Formulae 2-1, 2-2, 2-1a, and 2-2a, R21 may be selected from:
a hydrogen atom, a deuterium atom, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group;
a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group;
a phenyl, a naphthyl group, a pyridinyl group, a fluorenyl group, a benzofluorenyl group, and a carbazolyl group; and
a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group.
For example, in Formulae 2-1, 2-2, 2-1a, and 2-2a, R21 may be selected from:
a phenyl, a naphthyl group, a pyridinyl group, a fluorenyl group, a benzofluorenyl group, and a carbazolyl group; and
a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group.
For example, in Formulae 2-1, 2-2, 2-1a, and 2-2a, R22 to R27 may be each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group;
a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group;
a phenyl, a naphthyl group, a pyridinyl group, a fluorenyl group, a benzofluorenyl group, and a carbazolyl group; and
a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a fluorenyl group, and a carbazolyl group.
In Formula 1, m11 denotes the number of R11, and m11 may be an integer of 1 to 3. For example, m11 may be an integer of 1, but is not limited thereto. When m11 is an integer of 2 or greater, a plurality of R11 s are identical to or different from each other.
In Formula 1, k11 may be an integer of 1 to 4. For example, k11 may be an integer of 1, but is not limited thereto.
In Formula 1, R12 to R14 may be each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.
In some embodiments, in Formula 1, R12 to R14 may be each independently selected from, for example:
a hydrogen atom, a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.
In some embodiments, in Formula 1, R12 to R14 may be each independently selected from, for example:
a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group;
a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.
Also, in some embodiments, in Formula 1, R12 may be selected from, for example, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, and groups represented by Formulae 5-1 to 5-34:
















Also, in some embodiments, in Formula 1, R13 and R14 may be selected from, for example, a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group.
In Formula 1, a12 denotes the number of R12, a12 may be an integer of 0 to 3. When a12 is an integer of 2 or greater, a plurality of R12s may be identical to or different from each other.
In Formula 1, a13 denotes the number of R13, a13 may be an integer of 0 to 3. When a13 is an integer of 2 or greater, a plurality of R13s may be identical to or different from each other.
In Formula 1, a14 denotes the number of R14, a14 may be an integer of 0 to 3. When a14 is an integer of 2 or greater, a plurality of R14s may be identical to or different from each other.
For example, a pyrene-based compound represented by Formula 1 may be represented by one of Formulae 1-1 and 1-2:




In Formulae 1-1 and 1-2, descriptions of L11, n11, R12, and R21 are as stated above in the present specification.
In some embodiments, in Formula 1, the pyrene-based compound represented by Formula 1 may be represented by one of Formulae 1-1 and 1-2, and L11 in Formulae 1-1 and 1-2 may be represented by one of Formulae 4-1 to 4-23.
In some embodiments, in Formula 1, the pyrene-based compound represented by Formula 1 may be represented by one of Formulae 1-1 and 1-2, and n11 in Formulae 1-1 and 1-2 may be an integer of 0 or 1.
In some embodiments, in Formula 1, the pyrene-based compound represented by Formula 1 may be represented by one of Formulae 1-1 and 1-2, and R12 in Formulae 1-1 and 1-2 may be selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, and compounds of Formulae 5-1 to 5-34.
In some embodiments, the pyrene-based compound represented by Formula 1 may be represented by one of Formulae 1-1 and 1-2, and R21 in Formulae 1-1 and 1-2 may be selected from:
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.
The pyrene-based compound represented by Formula 1 may be one of Compounds 1 to 133 below, as examples:



































































































































































The pyrene compound may be a compound represented by Formula 1′:




As represented by Formula 1′, the pyrene-based compound represented by Formula 1 may include a benzocarbazole group and thus may have more electrons and a greater molecular weight (e.g., have more electrons and a greater molecular weight than a compound including only a carbazole group). Therefore, the pyrene-based compound represented by Formula 1 may have a high polarity having both hole and electron transporting abilities and thus may decrease a driving voltage and increase an efficiency of an OLED. Also, the pyrene-based compound represented by Formula 1 may have a high thermal stability, and thus, a glass transition temperature (Tg) of the compound may be high, and a lifespan of the OLED including the compound may be increased.
The pyrene-based compound represented by Formula 1 may include —CN and a benzocarbazole group together. Thus, a Tg of the compound may be high. When the pyrene-based compound represented by Formula 1 is applied to the OLED, a thin film stability of the OLED may increase and a lifespan of the OLED may be increased.
The OLED including the pyrene-based compound represented by Formula 1 may have a low driving voltage, a high efficiency, and a long lifespan.
The pyrene-based compound represented by Formula 1 may be synthesized by using a suitable organic synthesis method. The synthesis method for synthesizing the pyrene-based compound may be understood by one of ordinary skill in the art by referring to examples described below.
The pyrene-based compound represented by Formula 1 may be included between a pair of electrodes of an OLED. In some embodiments, the pyrene-based compound may be included in the electron transport region, for example, the ETL. Thus, an OLED may include a first electrode, a second electrode facing the first electrode, and an organic layer that is disposed between the first electrode and the second electrode and includes an emission layer (EML), wherein the organic layer includes at least one of pyrene-based compound represented by Formula 1.
As used herein, the expression “(the organic layer) may include at least one pyrene-based compound of Formula 1” may be understood as “(the organic layer) may include one pyrene-based compound represented by Formula 1 or at least two different compounds selected from pyrene-based compounds represented by Formula 1”.
In some embodiments, the organic layer may only include Compound 1 as the pyrene-based compound. Here, Compound 1 may be included in the electron transport region of the OLED. In other implementations, the organic layer may include Compound 1 and Compound 2 as the pyrene-based compound. Compound 1 and Compound 2 may be included in the same layer (e.g., both Compound 1 and Compound 2 in an electron transport region) or respectively included in two different layers (e.g., Compound 1 in an EML and Compound 2 in an electron transport region).
The organic layer may further include a hole transport region disposed between the first electrode and the EML. The hole transport region may include at least one of a hole injection layer (HIL), a hole transport layer (HTL), a buffer layer, and an electron blocking layer (EBL).
The organic layer may further include an electron transport region disposed between the EML and the second electrode. The electron transport region may include at least one of a hole blocking layer (HBL), an electron transport layer (ETL), and an electron injection layer (EIL).
The electron transport region may include the pyrene-based compound represented by Formula 1. For example, the electron transport region may include the ETL, and the ELT may include the pyrene-based compound represented by Formula 1.
As used herein, the expression “organic layer” refers to a single layer and/or multiple layers disposed between a first electrode and a second electrode of an OLED. The “organic layer” may include other materials besides an organic material.
FIG. 1 illustrates a schematic cross-sectional view of an OLED 10 according to an embodiment. The OLED 10 may include a first electrode 110, an organic layer 150, and a second electrode 190.
Hereinafter, a structure and a manufacturing method of an OLED according to an embodiment will be described in more detail with reference to FIG. 1.
A substrate may be additionally disposed on a lower part of the first electrode 110 or on an upper part of the second electrode 190 of FIG. 1. The substrate may be a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness.
The first electrode 110 may be formed by applying a first electrode material on the substrate by deposition or sputtering. When the first electrode 110 is an anode, the first electrode material may be selected from materials having a high work function to facilitate hole injection. The first electrode 110 may be a reflective electrode or a transparent electrode. Examples of the first electrode material may include indium-tin oxide (ITO), Indium-zinc-oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). When magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) is used as the first electrode material, the first electrode 110 may be formed as a reflective electrode.
The first electrode 110 may be formed as a single layer or have a multi-layered structure having at least two layers. For example, the first electrode 110 may have a three-layered structure, e.g., ITO/Ag/ITO.
The organic layer 150 may be formed on the first electrode 110. The organic layer 150 may include an EML.
The organic layer 150 may further include a hole transport region disposed between the first electrode and the EML. The organic layer 150 may further include an electron transport region disposed between the EML and the second electrode.
The hole transport region may include at least one of a HIL, a HTL, a buffer layer, and an EBL, and the electron transport region may include at least one of a HBL, an ETL, and an EIL.
The hole transport region may have a structure of a single layer formed of one material, a single layer formed of multiple different materials, or multiple layers formed of multiple different materials.
For example, the hole transport region may have a structure of a single layer formed of multiple different materials or a structure of HIL/HTL, HIL/HTL/buffer layer, HIL/buffer layer, HTL/buffer layer, or HIL/HTL/EBL sequentially stacked on the first electrode 110.
When the hole transport region includes the HIL, the HIL may be formed on the first electrode 110 by using various methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, inkjet printing, laser printing, or laser induced thermal imaging (LITI).
When the HIL is formed by vacuum deposition, the deposition conditions may be selected from ranges of, for example, a deposition temperature of about 100 to about 500° C., a degree of vacuum of about 10−8 to about 10−3 torr, and a deposition speed of about 0.01 to about 100 Å/sec in consideration of a desired compound for an HIL and a desired structure of the HIL.
When the HIL is formed by spin coating, the deposition conditions may be selected from ranges of, for example, a coating speed of about 2,000 rpm to about 5,000 rpm and a heat treatment temperature of about 80° C. to about 200° C. in consideration of a desired compound for an HIL and a desired structure of the HIL.
When the hole transport region includes the HTL, the HTL may be formed on the first electrode 110 or the HIL by using various methods such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, or LITI. When the HTL is formed by vacuum deposition and spin coating, the deposition conditions and the coating conditions of the HTL may be referred to the de deposition conditions and the coating conditions of the HIL.
The hole transport region may include at least one of m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, α-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, a compound represented by Formula 202:










In Formulae 201 and 202,
L201 to L205 are each independently selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C3-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C3-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C2-C60 heteroarylene group, and a substituted or unsubstituted divalent non-aromatic condensed polycyclic group;
at least one substituent of the substituted C3-C10 cycloalkylene group, substituted C3-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C3-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C2-C60 heteroarylene group, and substituted divalent non-aromatic condensed polycyclic group is selected from:
a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, a non-aromatic condensed polycyclic group, —N(Q201)(Q202), —Si(Q203)(Q204)(Q205), and —B(Q206)(Q207);
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, —N(Q211)(Q212), —Si(Q213)(Q214)(Q215), and —B(Q216)(Q217); and
—N(Q221)(Q222), —Si(Q223)(Q224)(Q225), and —B(Q226)(Q227);
xa1 to xa4 each denotes an integer of 0, 1, 2, or 3;
xa5 denotes an integer of 1, 2, 3, 4, or 5;
R201 to R205 are each independently selected from:
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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, —N(Q231)Q232), —Si(Q233)(Q234)(Q235), and —B(Q236)(Q237);
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, —N(Q241)(Q242), —Si(Q243)(Q244)(Q245), and —B(Q246)(Q247);
Q201 to Q207, Q211 to Q217, Q221 to Q227, Q231 to Q237, and Q241 to Q247 are each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.
For examples of L201 to L205 in Formulae 201 and 202 the description of L11 in the specification may be referred to, and for examples of R201 to R205 the description of R11 in the specification may be referred to.
For example, in Formulae 201 and 202, L201 to L205 may be each independently selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenene group, a dibenzofluorenene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
xa1 to xa4 each denotes an integer of 0, 1, or 2;
xa5 denotes an integer of 1, 2, or 3;
R201 to R205 are each independently selected from:
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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 azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.
The compound represented by Formula 201 may be represented by Formula 201A:




The compound represented by Formula 201 may be represented by Formula 201A-1:




The compound represented by Formula 202 may be represented by Formula 202A:




In Formulae 201A, 201A-1, and 202A, descriptions of L201 to L203, xa1 to xa3, xa5, and R202 to R204 may be referred to the descriptions stated in the specification, descriptions of R211 may be referred to the description of R203 stated in the specification, and R213 to R216 may be selected from a hydrogen atom, a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.
For example, in 201A, 201A-1, and 202A,
L201 to L203 may be each independently selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a quinolinylene group, an isoquinolinylene group, a quinoxalinylene group, a quinazolinylene group, a carbazolylene group, and a triazinylene group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
xa1 to xa3 each independently denotes an integer of 0 or 1;
R203, R211, and R212 are each independently selected from
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
R213 and R214 may be each independently selected from:
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 of a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
R215 and R216 are each independently selected from:
a hydrogen atom, a deuterium atom, a halogen atom, 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 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 of a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
xa5 denotes an integer of 1 or 2.
In Formulae 201A and 201A-1, R213 and R214 may link to each other and form a saturated or unsaturated ring.
The compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT16 below, as examples:






















A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes both the HIL and the HTL, a thickness of the HIL 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 HTL 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 thicknesses of the hole transport region, the HIL, and the HTL are within these ranges, satisfactory hole transporting properties may be obtained without substantial increase in driving voltage.
The hole transport region may further include a charge-generating material in addition to the materials above to improve conductivity. The charge-generating material may be homogenously or non-homogenously dispersed in the hole transport region.
The charge-generating 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 compounds, as examples. Examples of the p-dopant may include quinone derivative, such as a tetracyanoquinonedimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinondimethane (F4-TCNQ); metal oxides, such as a tungsten oxide and a molybdenum oxide; and Compound HT-D1 below, as examples:




The hole transport region may further include at least one of a buffer layer or an EBL in addition to the HIL and the HTL. The buffer layer may increase light-emitting efficiency by compensating an optical resonance distance according the wavelength of light emitted from the EML. The buffer layer may include a material that may be included in the hole transport region. The EBL may block injection of electrons from the electron transport region.
The EML may be formed on the first electrode 110 or the hole transport region by using various methods such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, or LITI. When the EML is formed by vacuum deposition and spin coating, the deposition conditions and the coating conditions for forming the HIL, as described above, may be referred to in determining suitable deposition conditions and coating conditions of the EML.
When the OLED 10 is a full-color OLED, the EML may be patterned as a red EML, a green EML, and a blue EML depending on a red pixel, a green pixel, and a blue pixel. In other implementations, the EML may have a multiple-layered structure, in which a red EML, a green EML, and a blue EML are stacked or a single-layered structure including all of a red light-emitting material, a green light-emitting material, and a blue light-emitting material mixed therein so as to emit white light. In other implementations, the EML may be a white light EML, and the OLED 10 may further include a color converting layer that converts the white light into light of desired color or a color filter.
The EML may include a host or a dopant.
The host may include at least one of TPBi, TBADN, ADN, a CBP, a CDBP, and TCP below:







The host may include a compound represented by Formula 301.

Ar301-[(L301)xb1-R301]xb2  <Formula 301>

In Formula 301,
Ar301 may be selected from:
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group;
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, pyrene, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, and —Si(Q301)(Q302)(Q303) (here, Q301 to Q303 are each independently selected from a hydrogen atom, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group);
the description of L301 may be the same with the description of L201 in the specification;
R301 may be selected from:
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 of a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a Spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
xb1 is an integer of 0, 1, 2 or 3; and
xb2 is an integer of 1, 2, 3 or 4.
For example, in Formula 301,
L301 may be selected from:
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group; and
a phenylene group, a naphthylene group, a fluorenylene group, a spiro-fluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, and a chrysenylene group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;
R301 may be selected from:
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 of a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group;
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, and a chrysenyl group.
The compound represented by Formula 301 may include at least one of Compounds H1 to H42 below, but is not limited thereto:




























Also, the host may include at least one of Compounds H43 to H49 below, as examples:







The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant.
The phosphorescent dopant may include an organic metal complex represented by Formula 401:




In Formula 401,
M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm);
X401 to X404 may be each independently nitrogen or carbon;
rings A401 and A402 are each independently selected from a substituted or unsubstituted benzene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenene group, a substituted or unsubstituted spiro-fluorenene group, a substituted or unsubstituted indene group, a substituted or unsubstituted pyrrole group, a substituted or unsubstituted thiophene group, a substituted or unsubstituted furan group, a substituted or unsubstituted imidazole group, a substituted or unsubstituted pyrazole group, a substituted or unsubstituted thiazole group, a substituted or unsubstituted isothiazole group, a substituted or unsubstituted oxazole group, a substituted or unsubstituted isooxazole group, a substituted or unsubstituted pyridine group, a substituted or unsubstituted pyrazine group, a substituted or unsubstituted pyrimidine group, a substituted or unsubstituted pyridazine group, a substituted or unsubstituted quinoline group, a substituted or unsubstituted isoquinoline group, a substituted or unsubstituted benzoquinoline group, a substituted or unsubstituted quinoxaline group, a substituted or unsubstituted quinazoline group, a substituted or unsubstituted carbazole group, a substituted or unsubstituted benzoimidazole group, a substituted or unsubstituted benzofuran group, a substituted or unsubstituted benzothiophene group, a substituted or unsubstituted isobenzothiophene group, a substituted or unsubstituted benzoxazole group, a substituted or unsubstituted isobenzoxazole group, a substituted or unsubstituted triazole group, a substituted or unsubstituted oxadiazole group, a substituted or unsubstituted triazine group, a substituted or unsubstituted dibenzofuran group, and a substituted or unsubstituted dibenzothiophene group;
at least one substituent of the substituted benzene group, substituted naphthalene group, substituted fluorenene group, substituted spiro-fluorenene group, substituted indene group, substituted pyrrole group, substituted thiophene group, substituted furan group, substituted imidazole group, substituted pyrazole group, substituted thiazole group, substituted isothiazole group, substituted oxazole group, substituted isooxazole group, substituted pyridine group, substituted pyrazine group, substituted pyrimidine group, substituted pyridazine group, substituted quinoline group, substituted isoquinoline group, substituted benzoquinoline group, substituted quinoxaline group, substituted quinazoline group, substituted a carbazole group, substituted benzoimidazole group, substituted benzofuran group, substituted benzothiophene group, substituted isobenzothiophene group, substituted benzoxazole group, substituted isobenzoxazole group, substituted triazole group, substituted oxadiazole group, substituted triazine group, substituted dibenzofuran group, and substituted dibenzothiophene group is selected from
a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group(aryloxy), a C6-C60 arylthio group(arylthio), a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group(non-aromatic condensed polycyclic group), —N(Q401)(Q402), —Si(Q403)(Q404)(Q405), and —B(Q406)(Q407);
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, —N(Q411)(Q412), —Si(Q413)(Q414)(Q415), and —B(Q416)(Q417); and
—N(Q421)(Q422), —Si(Q423)(Q424)(Q425), and —B(Q426)(Q427);
L401 may be an organic ligand;
xc1 may be an integer of 1, 2, or 3; and
xc2 may be an integer of 0, 1, 2, or 3;
L401 is a monovalent, divalent, or trivalent organic ligand. For example, L401 may be selected from a halogen ligand (e.g., Cl or F), a diketone ligand (e.g., acetylacetonate, 1,3-diphenyl-1,3-propanedionate, 2,2,6,6-tetramethyl-3,5-heptanedionate, or hexafluoroacetonate), a carboxylic acid ligand (e.g., picolinate, dimethyl-3-pyrazolecarboxylate, or benzoate), a carbon monoxide ligand, an isonitrile ligand, a cyano ligand, and a phosphorus ligand (e.g., phosphine or phosphaite), but is not limited thereto.
In Formula 401, when A401 has at least two substituents, the at least two substituents of A401 may link to each other and form a saturated or unsaturated ring.
In Formula 401, when A402 has at least two substituents, the at least two substituents of A402 may link to each other and form a saturated or unsaturated ring.
In Formula 401, when xc1 is 2 or greater, a plurality of ligands,




are identical to or different from each other. In Formula 401, when xc1 is 2 or greater, A401 and A402 may be linked to each other by directly linking to another neighboring ligand of A401 and A402 or with a connection group (e.g., a C1-C5 alkylene group or —N(R′)— (here, R′ is C1-C10 alkyl group or a C6-C20 aryl group) therebetween.

The phosphorescent dopant may include at least one of Compounds PD1 to PD74 below, as examples:

















































Also, the phosphorescent dopant may include PtOEP below:




The fluorescent dopant may include at least one of DPAVBi, BDAVBi, TBPe, DCM, DCJTB, Coumarin 6, and a C545T below:




Also, the fluorescent dopant may include a compound represented by Formula 501:




In Formula 501,
Ar501 may be selected from:
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group; and
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, pyrene, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, and —Si(Q501)(Q502)(Q503) (here Q501 to Q503 are each independently selected from a hydrogen atom, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group);
descriptions of L501 to L503 are the same with the description of L201 of the specification;
R501 and R502 may be each independently selected from:
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, and a dibenzofuranyl group, and a dibenzothiophenyl, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;
xd1 to xd3 are each independently an integer of 0, 1, 2, or 3; and
xb4 is an integer of 1, 2, 3, or 4.
The fluorescent host may include at least one of Compounds FD1 to FD8 below:










An amount of a dopant in the EML may be generally in a range of about 0.01 part to about 15 parts by weight based on about 100 parts by weight of a host, but is not limited thereto.
A thickness of the EML may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When a thickness of the EML is within this range, excellent light-emitting properties may be obtained without substantial increase in driving voltage.
Next, an electron transport region may be formed on the EML.
The electron transport region may include at least one of a HBL, an ETL, and an EIL, as examples.
For example, the electron transport region may have a structure of ETL/EIL or EBL/ETL/EIL sequentially stacked on the EML.
In some embodiments, the organic layer 150 of the OLED 10 may include the electron transport region disposed between the EML and the second electrode 190, and the pyrene-based compound represented by Formula 1 may be included in the electron transport region.
The electron transport region may include the HBL. The HBL may be formed to prevent triplet excitons or holes from being diffused to the ETL.
When the electron transport region includes the HBL, the HBL may be formed on the EML by using various methods such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, or LITI. When the HBL is formed by as vacuum deposition and spin coating, the deposition conditions and the coating conditions described with respect to the HIL may be referred to for suitable deposition conditions and coating conditions of the HBL.
The HBL may include, for example, at least one of BCP and Bphen below.




A thickness of the HBL may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When a thickness of the HBL is within this range, excellent hole blocking properties may be obtained without substantial increase in driving voltage.
The electron transport region may include the ETL. The ETL may be formed on the EML or the HBL by using various methods such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, or LITI. When ETL is formed by vacuum deposition and spin coating, the deposition conditions and the coating conditions described with respect to the HIL may be referred to for suitable deposition conditions and coating conditions of the ETL.
In some embodiments, the organic layer 150 of the OLED 10 may include the electron transport region disposed between the EML and the second electrode 190. The electron transport region may include the ETL, and the pyrene-based compound represented by Formula 1 may be included in the ETL.
The ETL may further include at least one of BCP and Bphen above and Alq3, Balq, TAZ, and NTAZ below in addition to the pyrene-based compound represented by Formula 1:




Also, the ETL may include at least one compound represented by Formula 601 in addition to the pyrene-based compound represented by Formula 1:

Ar601-[(L601)xe1-E601]xe2  <Formula 601>

In Formula 601,
Ar601 may be selected from
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, pyrene, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group; and
a naphthalene group, a heptalene group, a fluorenene group, a spiro-fluorenene group, a benzofluorenene group, a dibenzofluorenene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, pyrene, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, and an indenoanthracene group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, non-aromatic condensed polycyclic group, and —Si(Q301)(Q302)(Q303) (here, Q301 to Q303 are each independently selected from a hydrogen atom, a C1-C60 alkyl group, a C2-C60 alkenyl group, a C6-C60 aryl group, and a C2-C60 heteroaryl group);
a description of L601 may be the same as the description of L201 above;
E601 may be selected from:
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 isoxazolyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl, a benzocarbazolyl group, and a dibenzocarbazolyl group; and
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 isoxazolyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl, a benzocarbazolyl group, and a dibenzocarbazolyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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 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 isoxazolyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl, a benzocarbazolyl group, and a dibenzocarbazolyl group;
xe1 is an integer of 0, 1, 2, or 3; and
xe2 is an integer of 1, 2, 3, or 4.
The ETL may include at least one compound represented by Formula 602 in addition to the pyrene-based compound represented by Formula 1:




In Formula 602,
X611 may be N or C-(L611)xe611-R611, X612 may be N or C-(L612)xe612-R612, X613 may be N or C-(L613)xe613-R613, and at least one of X611 to X613 may be N;
a description of each of L611 to L616 may be the same as the description of L201 above;
R611 to R616 may each independently be selected from:
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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 azulenyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
xe611 to xe616 may be each independently an integer of 0, 1, 2, or 3.
The compound represented by Formula 601 and the compound represented by Formula 602 may include at least one of Compounds ET1 to ET15:
















A thickness of the ETL may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When a thickness of the ETL is within this range, excellent electron transporting properties may be obtained without substantial increase in driving voltage.
The ETL may further include a metal-containing material in addition to the materials above.
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 the EIL that facilitates injection of electrons from the second electrode 190.
The EIL may be formed on the ETL by using various methods such as vacuum deposition, spin coating, casting, LB deposition, inkjet printing, laser printing, or LITI. When EIL is formed by vacuum deposition and spin coating, the deposition conditions and the coating conditions described with respect to the HIL may be referred to for suitable deposition conditions and coating conditions of the EIL.
The EIL may include at least one selected from LiF, NaCl, a CsF, Li2O, BaO, and LiQ.
A thickness of the EIL may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When a thickness of the EIL is within this range, excellent electron injecting properties may be obtained without a substantial increase in driving voltage.
The second electrode 190 may be disposed on the organic layer 150. The second electrode 190 may be a cathode, which is an electron injection electrode. In this regard, a metal for forming the second electrode 190 may include a metal, an alloy, an electric conducting compound, and a mixture thereof having low work function. In particular, the second electrode 190 may be formed as a thin film by using lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag). Also, ITO or IZO may be used as metal for forming the second electrode 190. The second electrode 190 may be a reflective electrode or a transparent electrode.
Thus far, the OLED 10 has been described by referring to FIG. 1, but in other implementations, other structures of the OLED are possible.
As used herein, examples of the C1-C60 alkyl group may include a monovalent linear or branched aliphatic hydrocarbon group, such as a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a pentyl group, an iso-amyl group, a hexyl group, or the like. Examples of the substituted C1-C60 alkylene group include a divalent group that has the same structure as the C1-C60 alkyl group.
As used herein, a C1-C60 alkoxy group may denote a monovalent group having a formula of —OA101 (here, A101 is the C1-C60 alkyl group). Examples of the C1-C60 alkoxy group include a methoxy group, an ethoxy group, and an isopropyloxy group.
As used herein, the C2-C60 alkenyl group may have a structure including at least one carbon double bond in the middle or at an end of the C2-C60 alkyl group Examples of the C2-C60 alkenyl group include an ethenyl group, a propenyl group, and a butenyl group. As used herein, the C2-C60 alkenylene group may denote a divalent group that has the same structure as the C2-C60 alkenyl group.
As used herein, the C2-C60 alkynyl group may have a structure including at least one carbon triple bond in the middle or at an end of the C2-C60 alkyl group. Examples of the C2-C60 alkynyl group include an ethynyl group and a propynyl group. As used herein, the C2-C60 alkynylene group may denote a divalent group that has the same structure as the C2-C60 alkynyl group.
As used herein, the C3-C10 cycloalkyl group may denote a C3-C10 monovalent hydrocarbon monocyclic group. Examples of the C3-C10 cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. As used herein, the C3-C10 cycloalkylene group may denote a divalent group that has the same structure as the C3-C10 cycloalkyl group.
As used herein, the C3-C10 heterocycloalkyl group may denote a C3-C10 monovalent monocyclic group including at least one hetero atom of N, O, P, and S as a ring-forming atom. Examples of the C3-C10 heterocycloalkyl group include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. As used herein, the C3-C10 heterocycloalkylene group denotes a divalent group that has the same structure with the C3-C10 heterocycloalkyl group.
As used herein, the C3-C10 cycloalkenyl group may denote a C3-C10 monocyclic group having at least one double bond in the ring while not losing its aromaticity. Examples of the C3-C10 cycloalkenyl group include a cyclopentyl group, a cyclohexenyl group, and a cycloheptenyl group. As used herein, the C3-C10 cycloalkenylene group may denote a divalent group that has the same structure as the C3-C10 cycloalkenyl group.
As used herein, the C3-C10 heterocycloalkenyl group may denote a C3-C10 monovalent monocyclic group including at least one hetero atom of N, O, P, and S as a ring-forming atom and at least one double bond in the ring Examples of the C3-C10 heterocycloalkenyl group include a 2,3-hydrofuranyl group and a 2,3-hydrothiophenyl group. As used herein, the C3-C10 heterocycloalkenylene group may denote a divalent group that has the same structure as the C3-C10 heterocycloalkenyl group.
As used herein, the C6-C60 aryl group may denote a monovalent group having a C6-C60 carbocyclic aromatic system, and the C6-C60 arylene group may denote a divalent group that has a C6-C60 carbocyclic aromatic system. Examples of the C6-C60 aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. As used herein, when the C6-C60 aryl group and the C6-C60 arylene group include at least two rings, the rings may be fused to each other.
As used herein, the C2-C60 heteroaryl group may denote a monovalent group including at least one hetero atom selected from N, O, P, and S as a ring-forming atom and having a C2-C60 carbocyclic aromatic system. The C2-C60 heteroarylene group may denote a divalent group including at least one hetero atom selected from N, O, P, and S as a ring-forming atom and having a C2-C60 carbocyclic aromatic system. Examples of the C2-C60 heteroaryl group include 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 a C2-C60 heteroarylene group include at least two rings, the rings may be fused to each other.
As used herein, the C6-C60 aryloxy group may denote —OA102 (here, A102 is the C6-C60 aryl group), and the C6-C60 arylthio group denotes —SA103 (here, A103 is the C6-C60 aryl group).
As used herein, the non-aromatic condensed polycyclic group may denote a monovalent group having at least two rings that are condensed to each other and non-aromaticity as a whole molecule. The non-aromatic condensed polycyclic group may include i) C only or ii) one hetero atom selected from N, O, P, and S as a ring-forming member. Examples of the non-aromatic condensed polycyclic group include a fluorenyl group and a carbazolyl group. As used herein, the divalent non-aromatic condensed polycyclic group may denote a divalent group that has the same structure as the non-aromatic condensed polycyclic group.
As used herein, the expression “Ph” denotes a phenyl group, the expression “Me” denotes a methyl group, the expression “Et” denotes an ethyl group, and the expression “ter-Bu” or “But” denotes a tert-butyl group.
Hereinafter, an OLED according to an embodiment will now be described in more detail with reference to the following examples. In the examples, the expression “B was used instead of A” indicates that an amount per mol of A and an amount per mol B are the same.
The following Examples and Comparative Examples are provided in order to highlight characteristics of one or more embodiments, but it will be understood that the Examples and Comparative Examples are not to be construed as limiting the scope of the embodiments, nor are the Comparative Examples to be construed as being outside the scope of the embodiments. Further, it will be understood that the embodiments are not limited to the particular details described in the Examples and Comparative Examples.
EXAMPLE
Synthesis Example 1
Synthesis of Compound 1




Synthesis of Intermediate I-1
9.55 g (50.0 mmol) of 6H-benzo[def]carbazole was completely dissolved in 250 mL of carbon tetrachloride (CCl4), and 17.8 g (100.0 mmol) of N-bromosuccinimide was added thereto, and stirred at a temperature of 80° C. for 30 minutes. The resultant was cooled to room temperature and stirred for 30 minutes to precipitate a crystal. The crystal was collected by using a filter at a low pressure and washed with methanol to obtain 8.55 g of Intermediate I-1 (yield: 49%). The produced compound was confirmed by using LC-MS.
C14H7Br2N: M+ 346.9
Synthesis of Intermediate I-2
8.55 g (24.5 mmol) of Intermediate I-1, 6.0 g (29.4 mmol) of iodobenzene, 0.44 g (2.45 mmol) of 1,10-phenanthroline, 0.93 g (4.90 mmol) of CuI, and 10.2 g (73.5 mmol) of K2CO3 were dissolved in 100 mL of N,N-dimethylformamide (DMF) and stirred at a temperature of 80° C. for 24 hours. The reaction solution was cooled to room temperature and extracted with 100 mL of water. The collected supernatant was dried by using magnesium sulfate, and the solvent thereof was evaporated. The obtained residue was purified by using a silica gel column chromatography to obtain 8.23 g of Intermediate I-2 (yield: 79%). The produced compound was confirmed by using LC-MS.
C20H11Br2N: M+ 422.9
Synthesis of Intermediate I-3
8.23 g of Intermediate I-2 (19.3 mmol) and 2.57 g of CuCN (28.7 mmol) were dissolved in 70 mL of DMF and stirred at a temperature of 150° C. for 24 hours. The reaction solution was cooled to room temperature and 60 mL of ammonium hydroxide and 60 mL of water were added thereto, and the resultant was extracted with 50 mL of methylene chloride for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent thereof was evaporated, and the residue obtained therefrom was purified by using a silica gel column chromatography to obtain 3.3 g of Intermediate I-3 (yield: 46%). The produced compound was confirmed by using LC-MS.
C21H11BrN2: M+ 370.0
Synthesis of Intermediate I-4
3.3 g of Intermediate I-3 (8.89 mmol) was dissolved in 60 mL of THF, and 3.9 mL of n-BuLi (9.78 mmol in 2.5 M hexane) was slowly and dropwisely added thereto at a temperature of −78° C. After stirring at the same temperature, 2.3 mL (11.6 mmol) of 2-isoproxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was dropwisely added thereto, and stirred at room temperature for 24 hours. When the reaction was completed, 40 mL of water was added, and the resultant was extracted with 40 mL of ethylether for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent was evaporated therefrom. The residue obtained therefrom was purified by using a silica gel column chromatography to obtain 2.83 g of Intermediate I-4 (yield: 76%). The produced compound was confirmed by using LC-MS.
C27H23BN2O2: M+ 418.2
Synthesis of Compound 1
2.83 g (6.76 mmol) of Intermediate I-4, 1.90 g (6.76 mmol) of 1-bromopyrene, 0.39 g (0.34 mmol) of Pd(PPh3)4, and 2.80 g (20.3 mmol) of K2CO3 were dissolved in 60 mL of a mixture solution of THF/H2O (at a volume ratio of 2/1) and stirred at a temperature of 80° C. for 12 hours. The reaction solution was cooled to room temperature, and the resultant was extracted with 40 mL of water and 40 mL of ethylacetate for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent was evaporated therefrom. The obtained residue was purified by using a silica gel column chromatography to obtain 2.70 g of Compound 1 (yield: 81%). The produced compound was confirmed by using MS/FAB and 1H NMR (CDCl3, 400 MHz).
C37H20N2 cal. 492.16, found 492.21.
δ=8.21-8.19 (m, 1H), 8.13-8.12 (m, 1H), 8.11-8.10 (m, 1H), 8.09-8.08 (m, 2H), 8.06-8.05 (m, 2H), 8.02-7.99 (m, 2H), 7.87-7.85 (m, 1H), 7.71-7.69 (m, 1H), 7.66-7.64 (m, 1H), 7.55-7.49 (m, 4H), 7.47 (d, 1H), 7.42 (d, 1H), 7.40-7.36 (m, 2H)
Synthesis Example 2
Synthesis of Compound 3




Synthesis of Intermediate I-5
5.40 g (15 mmol) of 1,6-dibromopyrene, 1.90 g (10 mmol) of 2-pyridineboronic acid, 0.58 g (0.5 mmol) of tetrakis(triphenylphsohpine)palladium (Pd(PPh3)4), and 4.15 g (30 mmol) of K2CO3 were dissolved in 60 mL of a mixture solution of THF/H2O (at a volume ration of 2/1) and stirred at a temperature of 70° C. for 5 hours. The reaction solution was cooled to room temperature, and 50 mL of water was added thereto and the resultant was extracted with 50 mL of ethylether for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent was evaporated therefrom. The obtained residue was purified by using a silica gel column chromatography to obtain 2.26 g of Intermediate I-5 (yield: 63%). The produced compound was confirmed by using LC-MS.
C21H12BrN: M+ 357.0
Synthesis of Compound 3
2.26 g (6.3 mmol) of Intermediate I-5, 2.64 g (6.3 mmol) of Intermediate I-4, 0.36 g (0.31 mmol) of Pd(PPh3)4, and 2.61 g (18.9 mmol) of K2CO3 were dissolved in 60 mL of a mixture solution of THF/H2O (at a volume ratio of 2/1) and stirred at a temperature of 80° C. for 12 hours. The reaction solution was cooled to room temperature, and the resultant was extracted with 40 mL of water and 40 mL of ethylacetate for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent was evaporated therefrom. The obtained residue was purified by using a silica gel column chromatography to obtain 2.80 g of Compound 3 (yield: 78%). The produced compound was confirmed by using MS/FAB and 1H NMR.
C42H23N3 cal. 569.19, found 569.23.
δ=8.40-8.38 (m, 1H), 8.35 (d, 1H), 8.24 (d, 1H), 8.09-8.06 (m, 2H), 8.04-8.02 (m, 2H), 7.99-7.93 (m, 2H), 7.86-7.82 (tt, 1H), 7.76-7.73 (m, 1H), 7.71-7.66 (m, 3H), 7.55-7.48 (m, 4H), 7.46-7.41 (m, 2H), 7.40-7.35 (m, 2H), 7.25-7.22 (m, 1H)
Synthesis Example 3
Synthesis of Compound 13




Synthesis of Intermediate I-6
10.0 g (55.4 mmol) of 9,10-dihydrophenanthrene, 21.8 g (121.0 mmol) of N-bromosuccinimide, and 0.5 g (2.7 mmol) of p-TsOH were dissolved in 30 mL of acetonitrile and stirred at a temperature of 50° C. for 12 hours. The resultant was cooled to room temperature and stirred for 30 minutes to precipitate a crystal. The crystal was collected by using a filter at a low pressure and washed with methanol to obtain 8.4 g of Intermediate I-6 (yield: 45%), and a color of the crystal was gray. The produced compound was confirmed by using LC-MS.
C14H10Br2: M+ 335.9
Synthesis of Intermediate I-7
5.0 g (15.0 mmol) of Intermediate I-6 was completely dissolved in 50 mL of dichloromethane, 1.7 g (30.0 mmol) of nitric acid was added thereto at room temperature, and 1.5 g (15.0 mmol) of sulfuric acid was slowly and dropwisely added thereto and stirred at a temperature of 30° C. for 6 hours. After the reaction was completed, the resultant was cooled to room temperature, and 50 mL of methanol was added thereto and stirred for 2 hours to precipitate a crystal. The crystal collected by using a filter at a low pressure was washed with methanol, and thus 5.2 g of Intermediate I-7 (yield: 90%) was obtained. The produced compound was confirmed by using LC-MS.
C14H9Br2NO2: M+ 380.9
Synthesis of Intermediate I-8
5.2 g (13.6 mmol) of Intermediate I-7 was dissolved in 30 mL of o-dichlorobenzene, and the solution was heated for complete dissolution. Then, 5.35 g (20.4 mmol) of triphenyl phosphine was added thereto and stirred at a temperature of 180° C. for 3 hours. The reaction solution was cooled to room temperature, and the solvent was evaporated. The residue obtained therefrom was purified by using a silica gel column chromatography to obtain 3.5 g of Intermediate I-8 (yield: 73%). The produced compound was confirmed by using LC-MS.
C14H11Br2N: M+ 350.9
Synthesis of Intermediate I-9
3.5 g (10.0 mmol) of Intermediate I-8 was dissolved in 100 mL of toluene in oxygen atmosphere, and 0.6 g (0.3 mmol) of 2,3-dichloro-5,6-a dicyano group-1,4-benzoquinone and 0.2 g (0.3 mmol) of NaNO2 were added thereto, and stirred at a temperature of 110° C. for 6 hours. After the reaction was completed, the reaction solution was cooled to room temperature, and the solvent was evaporated. The residue obtained therefrom was purified by using a silica gel column chromatography to obtain 3.1 g of Intermediate I-9 (yield: 90%). The produced compound was confirmed by using LC-MS.
C14H7Br2N: M+ 346.9
Synthesis of Intermediate I-10
8.54 g of Intermediate I-10 (yield: 82%) was obtained in the same manner used in Synthesis of Intermediate I-2, except that Intermediate I-9 was used instead of Intermediate I-1 in the synthesis of Intermediate I-2. The produced compound was confirmed by using LC-MS.
C20H11Br2N: M+ 422.9
Synthesis of Intermediate I-11
3.21 g of Intermediate I-11 (yield: 43%) was obtained in the same manner used in Synthesis of Intermediate I-3, except that Intermediate I-10 was used instead of Intermediate I-2 in the synthesis of Intermediate I-3. The produced compound was confirmed by using LC-MS.
C21H11BrN2: M+ 370.0
Synthesis of Intermediate I-12
2.97 g of Intermediate I-12 (yield: 82%) was obtained in the same manner used in Synthesis of Intermediate I-4, except that Intermediate I-11 was used instead of Intermediate I-3 in the synthesis of Intermediate I-4. The produced compound was confirmed by using LC-MS.
C27H23BN2O2: M+ 418.2
Synthesis of Compound 13
3.43 g of Compound 13 (yield: 85%) was obtained in the same manner used in Synthesis of Compound 1, except that Intermediate I-12 was used instead of Intermediate I-4, and Intermediate I-13 was used instead of 1-bromopyrene in the synthesis of Compound 1. The produced compound was confirmed by using MS/FAB and 1H NMR.
C43H24N2 cal. 568.19, found 568.22.
δ=8.30-8.28 (m, 1H), 8.21-8.20 (m, 1H), 8.16-8.13 (m, 2H), 8.09-8.07 (m, 1H), 8.05-8.04 (m, 1H), 8.03-8.02 (m, 2H), 7.99-7.98 (m, 2H), 7.91-7.89 (m, 1H), 7.82-7.80 (m, 1H), 7.65-7.64 (m, 1H), 7.62-7.60 (m, 2H), 7.59-7.58 (m, 1H), 7.52-7.51 (m, 1H), 7.50-7.49 (m, 1H), 7.48-7.47 (m, 2H), 7.42-7.36 (m, 4H)
Synthesis Example 4
Synthesis of Compound 38




Synthesis of Intermediate I-14
2.0 g (10 mmol) of 4-bromophenylboronic acid, 3.57 g (10 mmol) of Intermediate I-13, 0.58 g (0.5 mmol) of Pd(PPh3)4, and 4.15 g (30 mmol) of K2CO3 were dissolved in 60 mL of a mixture solution of THF/H2O (at a volume ratio of 2/1) and stirred at a temperature of 70° C. for 5 hours. The reaction solution was cooled to room temperature, 50 mL of water was added thereto, and the resultant was extracted with 50 mL of ethylether for 3 times. The collected supernatant was dried by using magnesium sulfate, and the solvent was evaporated therefrom. The obtained residue was purified by using a silica gel column chromatography to obtain 2.64 g of Intermediate I-14 (yield: 61%). The produced compound was confirmed by using LC-MS.
C28H17Br: M+ 432.1
Synthesis of Compound 38
3.42 g of Compound 38 (yield: 87%) was obtained in the same manner used in Synthesis of Compound 1, except that Intermediate I-12 was used instead of Intermediate I-4, and Intermediate I-14 instead of 1-bromopyrene in the synthesis of Compound 1. The produced compound was confirmed by using MS/FAB and 1H NMR.
C49H28N2 cal. 644.23, found 644.19.
δ=8.12-8.10 (m, 1H), 8.09-8.08 (m, 1H), 8.07-8.06 (m, 1H), 8.05-8.04 (m, 1H), 8.03-8.02 (m, 2H), 8.01-8.00 (m, 1H), 7.99-7.97 (m, 2H), 7.92-7.91 (m, 1H), 7.90-7.89 (m, 1H), 7.88-7.86 (m, 1H), 7.83-7.82 (m, 1H), 7.80-7.79 (m, 1H), 7.65-7.63 (m, 2H), 7.62-7.59 (m, 4H), 7.52-7.49 (m, 3H), 7.48-7.47 (m, 1H), 7.41-7.35 (m, 4H)
Synthesis Example 5
Synthesis of Compound 72




Synthesis of Intermediate I-15
2.39 g of Intermediate I-15 (yield: 67%) was obtained in the same manner used in Synthesis of Intermediate I-5, except that 2,7-dibromopyrene was used instead of 1,6-dibromopyrene, and phenylboronic acid instead of 2-pyridineboronic acid in the synthesis of Intermediate I-5. The produced compound was confirmed by using LC-MS.
C22H13Br: M+ 356.0
Synthesis of Compound 72
3.08 g of Compound 72 (yield: 81%) was obtained in the same manner used in Synthesis of Compound 1, except that Intermediate I-15 was used instead of 1-bromopyrene, in the synthesis of Compound 1. The produced compound was confirmed by using MS/FAB and 1H NMR.
C43H24N2 cal. 568.19, found 568.22.
δ=8.29-8.28 (m, 2H), 8.27-8.26 (m, 2H), 8.16 (d, 1H), 8.07 (d, 1H), 7.98-7.96 (m, 4H), 7.78-7.73 (m, 3H), 7.59-7.57 (m, 1H), 7.56-7.53 (m, 1H), 7.52-7.49 (m, 3H), 7.47-7.42 (m, 4H), 7.40-7.36 (m, 2H)
Synthesis Example 6
Synthesis of Compound 130




Synthesis of Intermediate I-16
2.65 g of Intermediate I-16 (yield: 65%) was obtained in the same manner used in Synthesis of Intermediate I-15, except that 1-naphthylboronic acid was used instead of phenylboronic acid, in the synthesis of Intermediate I-15. The produced compound was confirmed by using LC-MS.
C26H15Br: M+ 406.0
Synthesis of Intermediate I-17
3.20 g of Intermediate I-17 (yield: 60%) was obtained in the same manner used in Synthesis of Intermediate I-14, except that 4-bromonaphthylboronic acid was used instead of 4-bromophenylboronic acid and Intermediate I-14 instead of Intermediate I-13, in the synthesis of Intermediate I-14. The produced compound was confirmed by using LC-MS.
C36H21Br: M+ 532.1
Synthesis of Compound 130
3.84 g of Compound 130 (yield: 86%) was obtained in the same manner used in Synthesis of Compound 1, except that Intermediate I-12 was used instead of Intermediate I-4 and Intermediate I-17 instead of 1-bromopyrene, in the synthesis of Compound 1. The produced compound was confirmed by using MS/FAB and 1H NMR.
C57H32N2 cal. 744.26, found 744.28.
δ=8.31-8.26 (m, 5H), 8.18-8.17 (m, 1H), 8.09-8.08 (m, 1H), 8.03-8.02 (m, 5H), 7.92-7.88 (m, 1H), 7.86-7.83 (m, 3H), 7.77-7.74 (m, 2H), 7.65-7.58 (m, 3H), 7.51-7.47 (m, 3H), 7.44-7.42 (m, 2H), 7.40-7.35 (m, 2H), 7.25-7.21 (m, 1H), 7.18-7.15 (m, 1H), 7.06-7.02 (m, 2H)
A synthesis method same with the synthesis pathways above and an appropriate intermediate material were used to synthesize additional compounds, and their 1H NMR and MS/FAB results are shown in Table 1.
Compounds other than those shown in Table 1 may be easily recognized to one of ordinary skill in the art in view of the synthesis method by referring to the synthesis pathways and the raw material.









TABLE 1









MS/FAB










Compound
1H NMR (CDCl3, 400 MHz)
found
calc.













1
δ = 8.21-8.19 (m, 1H), 8.13-8.12 (m, 1H), 8.11-8.10 (m, 1H), 8.09-8.08
492.21
492.16



(m, 2H), 8.06-8.05 (m, 2H), 8.02-7.99 (m, 2H), 7.87-7.85 (m, 1H), 7.71-



7.69 (m, 1H), 7.66-7.64 (m, 1H), 7.55-7.49 (m, 4H), 7.47 (d, 1H), 7.42 (d,



1H), 7.40-7.36 (m, 2H)


3
δ = 8.40-8.38 (m, 1H), 8.35 (d, 1H), 8.24 (d, 1H), 8.09-8.06 (m, 2H), 8.04-
569.23
569.19



8.02 (m, 2H), 7.99-7.93 (m, 2H), 7.86-7.82 (tt, 1H), 7.76-7.73 (m, 1H),



7.71-7.66 (m, 3H), 7.55-7.48 (m, 4H), 7.46-7.41 (m, 2H), 7.40-7.35 (m,



2H), 7.25-7.22 (m, 1H)


6
δ = 8.41 (d, 1H), 8.27 (d, 1H), 8.19-8.16 (m, 2H), 8.12-8.10 (m, 1H), 8.08-
645.18
645.22



8.05 (m, 2H), 8.02-8.01 (m, 1H), 7.99-7.96 (m, 1H), 7.92 (d, 1H), 7.81 (d,



1H), 7.79-7.74 (m, 2H), 7.73-7.70 (m, 2H), 7.66-7.64 (m, 1H), 7.55-7.51



(m, 4H), 7.50-7.47 (m, 3H), 7.43-7.35 (m, 4H)


13
δ = 8.30-8.28 (m, 1H), 8.21-8.20 (m, 1H), 8.16-8.13 (m, 2H), 8.09-8.07
568.22
568.19



(m, 1H), 8.05-8.04 (m, 1H), 8.03-8.02 (m, 2H), 7.99-7.98 (m, 2H), 7.91-



7.89 (m, 1H), 7.82-7.80 (m, 1H), 7.65-7.64 (m, 1H), 7.62-7.60 (m, 2H),



7.59-7.58 (m, 1H), 7.52-7.51 (m, 1H), 7.50-7.49 (m, 1H), 7.48-7.47 (m,



2H), 7.42-7.36 (m, 4H)


16
δ = 8.32-8.30 (m, 1H), 8.21-8.20 (m, 1H), 8.15-8.12 (m, 3H), 8.08-8.06
618.25
618.21



(m, 1H), 8.04-8.03 (m, 2H), 8.01-7.99 (m, 1H), 7.92-7.91 (m, 1H), 7.90-



7.88 (m, 3H), 7.84-7.82 (m, 2H), 7.76-7.74 (m, 1H), 7.64-7.61 (m, 1H),



7.60-7.57 (m, 3H), 7.56-7.53 (dd, 1H), 7.50-7.47 (m, 2H), 7.41-7.36 (m,



3H)


22
δ = 8.47-8.45 (d, 1H), 8.42-8.41 (m, 2H), 8.40-8.39 (m, 2H), 8.25-8.23 (m,
723.21
723.24



1H), 8.20-8.19 (m, 2H), 8.17-8.15 (m, 2H), 8.14-8.11 (m, 3H), 8.08-8.07



(m, 1H), 8.03 (d, 1H), 7.68-7.62 (m, 7H), 7.53-7.49 (m, 2H), 7.45 (t, 1H),



7.42-7.38 (m, 4H)


25
δ = 8.33-8.31 (m, 1H), 8.30-8.28 (m, 1H), 8.15-8.12 (m, 3H), 8.07-8.05
618.18
618.21



(m, 1H), 8.04-8.03 (m, 1H), 8.01-8.00 (m, 1H), 7.92-7.91 (m, 2H), 7.90-



7.85 (m, 3H), 7.84-7.81 (m, 2H), 7.75-7.70 (m, 2H), 7.61-7.57 (m, 1H),



7.56-7.55 (m, 2H), 7.54-7.53 (m, 1H), 7.49-7.46 (m, 2H), 7.42 (d, 1H),



7.40-7.36 (m, 2H)


29
δ = 8.12-8.10 (m, 1H), 8.07 (d, 1H), 8.01-7.99 (m, 3H), 7.95-7.92 (m, 1H),
694.27
694.24



7.87-7.85 (m, 1H), 7.83-7.80 (m, 3H), 7.79-7.78 (m, 1H), 7.74-7.72 (m,



3H), 7.68-7.66 (m, 1H), 7.65-7.64 (m, 1H), 7.62-7.58 (m, 3H), 7.55-7.53



(m, 1H), 7.52-7.45 (m, 6H), 7.42 (d, 1H), 7.40-7.38 (m, 1H), 7.30-7.26 (tt,



1H), 7.04-7.00 (tt, 1H)


32
δ = 8.41 (d, 1H), 8.32-8.29 (m, 2H), 8.12-8.08 (m, 2H), 8.07-8.00 (m, 4H),
722.21
722.25



7.93-7.92 (m, 1H), 7.91-7.87 (m, 3H), 7.82-7.78 (m, 2H), 7.75-7.73 (m,



2H), 7.72-7.70 (m, 3H), 7.67-7.65 (m, 1H), 7.61-7.59 (m, 1H), 7.56-7.47



(m, 6H), 7.42 (d, 1H), 7.40-7.35 (m, 1H)


38
δ = 8.12-8.10 (m, 1H), 8.09-8.08 (m, 1H), 8.07-8.06 (m, 1H), 8.05-8.04
644.19
644.23



(m, 1H), 8.03-8.02 (m, 2H), 8.01-8.00 (m, 1H), 7.99-7.97 (m, 2H), 7.92-



7.91 (m, 1H), 7.90-7.89 (m, 1H), 7.88-7.86 (m, 1H), 7.83-7.82 (m, 1H),



7.80-7.79 (m, 1H), 7.65-7.63 (m, 2H), 7.62-7.59 (m, 4H), 7.52-7.49 (m,



3H), 7.48-7.47 (m, 1H), 7.41-7.35 (m, 4H)


42
δ = 8.41 (d, 1H), 8.20-8.19 (m, 1H), 8.18-8.16 (m, 1H), 8.12-8.10 (m, 1H),
725.22
721.25



8.09-8.07 (m, 1H), 8.06-8.05 (m, 2H), 8.03-8.00 (m, 2H), 7.93-7.91 (m,



2H), 7.90-7.85 (m, 4H), 7.81 (d, 1H), 7.79-7.76 (m, 1H), 7.73-7.70 (m,



1H), 7.66-7.63 (m, 3H), 7.62-7.58 (m, 3H), 7.51-7.47 (m, 4H), 7.42-7.35



(m, 3H)


45
δ = 8.36-8.35 (dd, 1H), 8.34-8.33 (dd, 1H), 8.29 (d, 2H), 8.22 (t, 1H), 8.16-
798.33
798.28



8.14 (m, 1H), 8.11-8.09 (m, 1H), 8.07-8.05 (m, 2H), 8.03-7.99 (m, 3H),



7.93-7.82 (m, 6H), 7.82-7.80 (m, 1H), 7.73-7.70 (m, 4H), 7.64-7.63 (m,



2H), 7.62-7.58 (m, 3H), 7.51-7.47 (m, 2H), 7.40-7.35 (m, 2H), 7.30-7.26



(m, 2H)


49
δ = 8.16-8.15 (m, 1H), 8.14-8.12 (m, 1H), 8.11-8.10 (m, 1H), 8.08-8.06
694.27
694.24



(m, 1H), 8.05-8.03 (m, 1H), 8.02-8.01 (m, 1H), 7.99-7.98 (m, 1H), 7.93-



7.91 (m, 2H), 7.90-7.89 (m, 2H), 7.88-7.87 (m, 2H), 7.86-7.85 (m, 1H),



7.83-7.82 (m, 2H), 7.81-7.79 (m, 2H), 7.77-7.76 (m, 1H), 7.68-7.65 (m,



1H), 7.62-7.61 (m, 1H), 7.60-7.57 (m, 2H), 7.56-7.55 (m, 1H), 7.54-7.53



(m, 1H), 7.49-7.46 (m, 2H), 7.44-7.41 (m, 1H), 7.40-7.36 (m, 1H), 7.35-



7.34 (dd, 1H)


51
δ = 8.19-8.18 (tt, 1H), 8.09-8.08 (m, 1H), 8.06-8.05 (m, 1H), 8.03-7.99 (m,
694.27
694.24



4H), 7.94-7.89 (m, 2H), 7.86-7.83 (m, 1H), 7.81-7.79 (m, 1H), 7.77-7.76



(m, 1H), 7.75-7.73 (m, 1H), 7.70-7.67 (m, 2H), 7.65-7.64 (m, 1H), 7.62-



7.50 (m, 2H), 7.56-7.53 (m, 2H), 7.52-7.51 (m, 3H), 7.50-7.48 (m, 2H),



7.47-7.45 (m, 1H), 7.43-7.41 (m, 1H), 7.40-7.35 (m, 1H), 7.30-7.26 (m,



1H), 7.05-7.01 (m, 1H)


55
δ = 8.45-8.43 (m, 1H), 8.30-8.28 (m, 1H), 8.27-8.26 (m, 1H), 8.23-22 (m,
695.21
695.24



1H), 8.13-8.11 (m, 1H), 8.08-8.06 (m, 2H), 8.04-8.03 (m, 2H), 8.01-7.99



(m, 3H), 7.97-7.94 (m, 1H), 7.93-7.89 (m, 2H), 7.88-7.83 (m, 3H), 7.76-



7.74 (m, 1H), 7.59-7.56 (m, 1H), 7.75-7.48 (m, 6H), 7.43-7.36 (m, 3H)


61
δ = 8.53 (d, 1H), 8.39 (d, 1H), 8.15-8.14 (m, 1H), 8.13-8.11 (m, 3H), 8.10-
569.21
569.19



8.07 (m, 3H), 8.03-8.02 (m, 2H), 8.01-7.99 (m, 2H), 7.95-7.93 (dd, 1H),



7.64-7.58 (m, 4H), 7.50-7.47 (m, 2H), 7.45-7.43 (m, 1H), 7.40-7.35 (m,



2H)


67
δ = 8.40-8.39 (m, 1H), 8.33-8.31 (m, 3H), 8.30-8.28 (m, 2H), 8.23-8.21
848.25
848.29



(m, 3H), 8.17-8.16 (m, 1H), 8.11-8.07 (m, 4H), 8.03-8.00 (m, 3H), 7.97-



7.93 (m, 3H), 7.85-7.83 (m, 1H), 7.76-7.74 (m, 1H), 7.64-7.59 (m, 3H),



7.53-7.52 (m, 1H), 7.51-7.47 (m, 5H), 7.43 (d, 1H), 7.40-7.35 (m, 2H),



7.31-7.27 (m, 2H)


70
δ = 8.47-8.45 (m, 1H), 8.31-8.29 (m, 1H), 8.23-8.21 (m, 2H), 8.20-8.19
695.27
695.24



(m, 1H), 8.13-8.11 (m, 1H), 8.10-8.09 (m, 1H), 8.08-8.06 (m, 2H), 8.05-



8.04 (m, 1H), 8.03-8.00 (m, 2H), 7.96-7.89 (m, 3H), 7.86-7.85 (m, 1H),



7.84-7.81 (m, 2H), 7.79-7.75 (m, 2H), 7.66-7.64 (m, 1H), 7.58-7.53 (m,



2H), 7.49-7.46 (m, 2H), 7.44-7.43 (m, 1H), 7.41-7.35 (m, 3H)


72
δ = 8.29-8.28 (m, 2H), 8.27-8.26 (m, 2H), 8.16 (d, 1H), 8.07 (d, 1H), 7.98-
568.22
568.19



7.96 (m, 4H), 7.78-7.73 (m, 3H), 7.59-7.57 (m, 1H), 7.56-7.53 (m, 1H),



7.52-7.49 (m, 3H), 7.47-7.42 (m, 4H), 7.40-7.36 (m, 2H)


75
δ = 8.31-8.30 (m, 2H), 8.27-8.26 (m, 2H), 8.24-8.23 (m, 1H), 8.17-8.15
618.18
618.21



(m, 1H), 8.07 (d, 1H), 8.02-8.01 (m, 1H), 8.00-7.98 (m, 4H), 7.97-7.95



(m, 1H), 7.94-7.92 (m, 1H), 7.87-7.85 (m, 1H), 7.76 (d, 1H), 7.62-7.59



(m, 1H), 7.58-7.57 (m, 1H), 7.56-7.53 (m, 2H), 7.52-7.47 (m, 4H), 7.42



(d, 1H), 7.40-7.35 (m, 1H)


79
δ = 8.39-8.37 (m, 2H), 8.29-8.27 (m, 3H), 8.25-8.24 (m, 2H), 8.20-8.19
722.19
722.25



(m, 2H), 8.14-8.13 (m, 1H), 8.07 (d, 1H), 8.02-7.99 (m, 4H), 7.78-7.75



(m, 1H), 7.73-7.70 (m, 4H), 7.59-7.57 (m, 1H), 7.54-7.48 (m, 5H), 7.43



(d, 1H), 7.40-7.37 (m, 1H), 7.31-7.28 (m, 2H)


84
δ = 8.56-8.54 (m, 1H), 8.42-8.40 (m, 1H), 8.29-8.28 (m, 2H), 8.20-8.19
569.22
569.19



(m, 1H), 8.17-8.16 (m, 2H), 8.09-8.08 (m, 1H), 8.06-8.03 (m, 2H), 8.01-



7.99 (m, 4H), 7.64-7.58 (m, 3H), 7.50-7.43 (m, 4H), 7.41-7.35 (m, 2H)


89
δ = 8.56-8.54 (dd, 1H), 8.42-8.41 (m, 2H), 8.36-8.34 (m, 1H), 8.30-8.29
695.22
695.24



(m, 1H), 8.28-8.27 (m, 2H), 8.20-8.18 (dd, 1H), 8.12-8.10 (dd, 1H), 8.09-



8.08 (m, 1H), 8.03 (d, 1H), 8.01-7.99 (m, 2H), 7.94-7.92 (m, 2H), 7.84-



7.81 (m, 2H), 7.73-7.71 (m, 2H), 7.64-7.58 (m, 4H), 7.50-7.36 (m, 6H)


100
δ = 8.52-8.51 (m, 2H), 8.32-8.31 (m, 2H), 8.22-8.21 (m, 1H), 8.19-8.18
721.24
721.25



(m, 1H), 8.14-8.11 (m, 2H), 8.08-8.06 (m, 1H), 8.02-8.01 (m, 1H), 7.99-



7.98 (m, 1H), 7.90-7.84 (m, 5H), 7.74-7.65 (m, 4H), 7.56-7.47 (m, 8H),



7.43-7.35 (m, 3H)


106
δ = 8.29-8.28 (m, 2H), 8.24-8.23 (m, 1H), 8.21-8.20 (m, 1H), 8.09-8.08
568.20
568.19



(m, 2H), 8.06-8.05 (m, 2H), 8.03-8.00 (m, 2H), 7.94-7.91 (m, 2H), 7.90-



7.87 (m, 2H), 7.84-7.83 (m, 1H), 7.82-7.81 (m, 1H), 7.63-7.58 (m, 4H),



7.51-7.47 (m, 2H), 7.40-7.34 (m, 2H)


116
δ = 8.50-8.49 (m, 2H), 8.45-8.44 (m, 2H), 8.43-8.42 (m, 2H), 8.34-8.33
799.28
799.27



(m, 1H), 8.32-8.31 (m, 1H), 8.26-8.25 (m, 2H), 8.18-8.16 (m, 2H), 8.09-



8.08 (m, 1H), 8.07-8.06 (m, 1H), 8.03 (d, 1H), 7.94-7.86 (m, 4H), 7.63-



7.58 (m, 8H), 7.51-7.47 (m, 2H), 7.42-7.34 (m, 4H)


121
δ = 8.65-8.64 (dd, 1H), 8.42-8.41 (m, 2H), 8.28-8.27 (m, 2H), 8.19-8.14
645.23
645.22



(m, 3H), 8.11-8.06 (m, 2H), 8.01-7.99 (m, 2H), 7.96-7.94 (m, 1H), 7.78-



7.74 (m, 3H), 7.68-7.66 (m, 1H), 7.60-7.57 (m, 1H), 7.54-7.38 (m, 9H)


130
δ = 8.31-8.26 (m, 5H), 8.18-8.17 (m, 1H), 8.09-8.08 (m, 1H), 8.03-8.02
744.28
744.26



(m, 5H), 7.92-7.88 (m, 1H), 7.86-7.83 (m, 3H), 7.77-7.74 (m, 2H), 7.65-



7.58 (m, 3H), 7.51-7.47 (m, 3H), 7.44-7.42 (m, 2H), 7.40-7.35 (m, 2H),



7.25-7.21 (m, 1H), 7.18-7.15 (m, 1H), 7.06-7.02 (m, 2H)









Example 1
A 15 Ω/cm2 (1200 Å) ITO glass substrate (Corning), as an anode, was cut to a size of 50 mm×50 mm×0.7 mm, washed with ultrasonic waves in isopropyl alcohol and pure water for 5 minutes each, and then cleaned with UV for 30 minutes and exposed to ozone. The ITO glass substrate was mounted on a vacuum depositor.
2-TNATA was vacuum deposited on the ITO glass substrate to form a HIL having a thickness of 600 Å, and NPB was then deposited on the HIL to form a HTL having a thickness of 300 Å. Then, ADN (as a host) and DPAVBi (as a dopant) were co-deposited on the HTL at a weight ratio of 98:2 to form an EML having a thickness of 300 Å.
Compound 3 was deposited on the EML to form an ETL having a thickness of 300 Å, and LiF was deposited on the ETL to form an EIL having a thickness of 10 Å. Al was deposited on the EIL to form a cathode having a thickness of 3,000 Å, thereby completing manufacture of an OLED.




Example 2
An OLED was manufactured in the same manner as in Example 1, except that Compound 16 was used instead of Compound 3 in the formation of the ETL.
Example 3
An OLED was manufactured in the same manner as in Example 1, except that Compound 38 was used instead of Compound 3 in the formation of the ETL.
Example 4
An OLED was manufactured in the same manner as in Example 1, except that Compound 51 was used instead of Compound 3 in the formation of the ETL.
Example 5
An OLED was manufactured in the same manner as in Example 1, except that Compound 72 was used instead of Compound 3 in the formation of the ETL.
Example 6
An OLED was manufactured in the same manner as in Example 1, except that Compound 89 was used instead of Compound 3 in the formation of the ETL.
Example 7
An OLED was manufactured in the same manner as in Example 1, except that Compound 130 was used instead of Compound 3 in the formation of the ETL.
Comparative Example 1
An OLED was manufactured in the same manner as in Example 1, except that Alq3 was used instead of Compound 3 in the formation of the ETL.




Comparative Example 2
An OLED was manufactured in the same manner as in Example 1, except that Compound A was used instead of Compound 3 in the formation of the ETL.
<Compound A>




Comparative Example 3
An OLED was manufactured in the same manner as in Example 1, except that Compound B was used instead of Compound 3 in the formation of the ETL.
<Compound B>




Comparative Example 4
An OLED was manufactured in the same manner as in Example 1, except that Compound C was used instead of Compound 3 in the formation of the ETL.
<Compound C>




Evaluation Example 1
Driving voltage, current density, brightness, efficiency, and half-life of the OLEDs of Examples 1 to 7 and Comparative Examples 1 to 4 were evaluated using a current-voltmeter, Kethley SMU 236 and a brightness photometer, PR650, and the results are shown in Table 2 below. The half-life was time consumed for an OLED to have 50% reduced brightness compared to its initial brightness.















TABLE 2








Driving
Current



Half-life




voltage
density
Brightness
Efficiency

(hr@



ETL
(V)
(mA/cm2)
(cd/m2)
(cd/A)
Color
100 mA/cm2)























Example 1
Compound 3
5.52
50
3365
6.73
Blue
407


Example 2
Compound 16
5.26
50
3275
6.55
Blue
415


Example 3
Compound 38
5.38
50
3235
6.47
Blue
422


Example 4
Compound 51
5.61
50
3105
6.21
Blue
376


Example 5
Compound 72
5.18
50
3030
6.06
Blue
411


Example 6
Compound 89
5.31
50
3140
6.28
Blue
395


Example 7
Compound
5.26
50
3075
6.15
Blue
402



130


Comparative
Alq3
7.35
50
2065
4.13
Blue
145


Example 1


Comparative
Compound A
6.16
50
2770
5.54
Blue
324


Example 2


Comparative
Compound B
6.08
50
2555
5.11
Blue
228


Example 3


Comparative
Compound C
6.03
50
2640
5.28
Blue
263


Example 4









Referring to Table 2, it was confirmed that the OLEDs of Examples 1 to 7 have better driving voltages, current densities, brightness, efficiency, and half-lives than the OLEDs of Comparative Examples 1 to 4.
As described above, according to the one or more of the above embodiments, an OLED including the pyrene-based compound may have high efficiency, low driving voltage, and long lifespan.
Example embodiments have been disclosed herein, and although specific terms are employed, they are used and are to be interpreted in a generic and descriptive sense only and not for purpose of limitation. In some instances, as would be apparent to one of ordinary skill in the art as of the filing of the present application, features, characteristics, and/or elements described in connection with a particular embodiment may be used singly or in combination with features, characteristics, and/or elements described in connection with other embodiments unless otherwise specifically indicated. Accordingly, it will be understood by those of skill in the art that various changes in form and details may be made without departing from the spirit and scope thereof as set forth in the following claims.

## Claims

1. A pyrene-based compound represented by Formula 1:



wherein, in Formula 1,
L11 is selected from a substituted or unsubstituted C3-C10 cycloalkylene group, a substituted or unsubstituted C1-C10 heterocycloalkylene group, a substituted or unsubstituted C3-C10 cycloalkenylene group, a substituted or unsubstituted C1-C10 heterocycloalkenylene group, a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, and a substituted or unsubstituted non-aromatic condensed polycycle;
at least one substituent of the substituted C3-C10 cycloalkylene group, substituted C1-C10 heterocycloalkylene group, substituted C3-C10 cycloalkenylene group, substituted C1-C10 heterocycloalkenylene group, substituted C6-C60 arylene group, substituted C1-C60 heteroarylene group, and substituted non-aromatic condensed polycyclic group is selected from
a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
n11 is an integer of 0 to 3;
m11 is an integer of 1 to 3;
R11 is represented by one of Formulae 2-1 and 2-2;
k11 is an integer of 1 to 4;
R12 to R14 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group(aryloxy), a C6-C60 arylthio group(arylthio), a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle; and
a C3-C10 cycloalkyl group, a C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycycle, each substituted with at least one of a deuterium atom, a halogen atom, 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 C1-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C1-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C1-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a12 is an integer of 1 to 5;
a13 and a14 are each independently an integer of 1 to 3;




wherein, in Formulae 2-1 and 2-2,
R21 to R27 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, 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, 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 of a deuterium atom, a halogen atom, 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 C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C3-C10 cycloalkyl group, a C3-C10 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, 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 heterocycloalkyl group, a C3-C10 cycloalkenyl group, a C3-C10 heterocycloalkenyl group, a C6-C60 aryl group, a C6-C60 aryloxy group, a C6-C60 arylthio group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a22 to a27 are each independently an integer of 0 to 3;
b11 to b16 are each independently an integer of 0 to 2;
the sum of b11, b12, and b13 is 1 or greater, and the sum of b14, b15, and b16 is 1 or greater; and
* is a binding site with L11, or a pyrene ring in Formula 1.

2. The pyrene-based compound as claimed in claim 1, wherein L11 is represented by Formulae 3-1 to 3-32:












wherein, in Formulae 3-1 to 3-32,
* and *′ represent a binding site with a pyrene ring, R11 or another L11 in Formula 1,
Y1 is selected from C(Q31)(Q32), N(Q33), an oxygen atom, a sulfur atom, and Si(Q34)(Q35);
Q31 to Q35 are each independently selected from a hydrogen atom, a deuterium atom, a C1-C20 alkyl group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group;
Z1 and Z2 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl 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; and
d6 is an integer of 1 to 5.

3. The pyrene-based compound as claimed in claim 1, wherein L11 is represented by Formulae 4-1 to 4-23:









where * and *′ represent a binding site with a pyrene ring, R11 or another L11 in Formula 1.

4. The pyrene-based compound as claimed in claim 1, wherein n11 and n12 each independently an integer of 0 or 1.

5. The pyrene-based compound as claimed in claim 1, wherein R11 is represented by one of Formulae 2-1a and 2-2a:



wherein, in Formulae 2-1a and 2-2a,
R21 to R27 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, and a C1-C60 alkoxy group;
a C1-C60 alkyl group and a C1-C60 alkoxy group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group;
a22 to a27 are each independently an integer of 0 to 3;
b13 and b14 are each independently an integer of 1 or 2; and
* is a binding site with L11 or a pyrene ring in Formula 1.

6. The pyrene-based compound as claimed in claim 1, wherein R11 is represented by one of Formula 2-1b:



wherein, in Formula 2-1b,
R21 is selected from
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
* is a binding site with L11 or a pyrene ring in Formula 1.

7. The pyrene-based compound as claimed in claim 1, wherein R12 to R14 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, 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 phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, 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, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.

8. The pyrene-based compound as claimed in claim 1, wherein R12 to R14 are each independently selected from
a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group;
a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, and a triazinyl group; and
a phenyl group, a naphthyl group, a fluorenyl group, a benzofluorenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one of a deuterium atom, a halogen atom, a cyano group, a nitro group, a C1-C20 alkyl group, a C1-C20 alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a spiro-fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, and a triazinyl group.

9. The pyrene-based compound as claimed in claim 1, wherein R12 is selected from
a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, and one selected from Formulae 5-1 to 5-34;

















where * represents a binding site with a pyrene ring in Formula 1.

10. The pyrene-based compound as claimed in claim 1, wherein R13 and R14 are each independently selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, and a tert-butoxy group.

11. The pyrene-based compound as claimed in claim 1, wherein a12 is 1.

12. The pyrene-based compound as claimed in claim 1 represented by one of Formulae 1-1 and 1-2:



wherein, descriptions of L11, n11, R12, and R21 are same as those described in claim 1.

13. The pyrene-based compound as claimed in claim 12, wherein
L11 is represented by one of Formulae 4-1 to 4-23; and
n11 is an integer of 0 or 1:











where * and *′ represent a binding site with a pyrene ring, R11 or another L11 in Formula 1.

14. The pyrene-based compound as claimed in claim 12, wherein R12 is selected from a hydrogen atom, a deuterium atom, a halogen atom, a cyano group, a nitro group, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a sec-butyl group, an iso-butyl group, a tert-butyl group, a methoxy group, an ethoxy group, a tert-butoxy group, and Formulae 5-1 to 5-34:
















where * represents a binding site with a pyrene ring in Formula 1.

15. The pyrene-based compound as claimed in claim 12, wherein R21 is selected from
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group; and
a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group, each substituted with at least one of a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a C6-C60 aryl group, a C2-C60 heteroaryl group, and a non-aromatic condensed polycyclic group.

16. The pyrene-based compound as claimed in claim 1, wherein the compound is one of Compounds 1 to 133:

17. An organic light-emitting device (OLED), comprising
a first electrode;
a second electrode facing the first electrode; and
an organic layer between the first electrode and the second electrode, the organic layer including an emission layer,
wherein the organic layer includes the pyrene-based compound as claimed in claim 1.

18. The OLED as claimed in claim 17, wherein:
the organic layer includes an electron transport region between the emission layer and the second electrode, and
the electron transport region includes the pyrene-based compound of claim 1.

19. The OLED as claimed in claim 18, wherein:
the electron transport region includes an electron transport layer, and the electron transport layer includes the pyrene-based compound of claim 1.

20. The OLED as claimed in claim 17, wherein the organic layer includes a hole transport region disposed between the first electrode and the emission layer.