Patent ID: 12225817

DETAILED DESCRIPTION

Reference will now be made in detail to exemplary embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present exemplary embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the exemplary embodiments are merely described below, by referring to the figures, to explain aspects. Expressions such as “at least one of,” when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list.

It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, the singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

The term “or” means “and/or.” It will be further understood that the terms “comprises” and/or “comprising,” or “includes” and/or “including” when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

“About” or “approximately” as used herein is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

A condensed cyclic compound may be represented by Formula 1.

In Formula 1, Ar1may be a group represented by Formula 2 and Ar2may be a group represented by Formula 3.

CY1in Formula 2 may be selected from a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group, and CY2and CY3in Formula 3 may be each independently selected from a benzene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

L1and L2in Formula 1 may be each independently a group represented by Formula 4 or a group represented by Formula 5, and at least one of L1and L2may be selected from groups represented by Formula 4.

CY4and CY5in Formulae 4 and 5 may be each independently selected from C5-C30carbocyclic groups.

R1to R4, R10, R20and R30in Formulae 2 to 5 may be each independently selected from a hydrogen, a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C60alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C7-C60arylalkyl group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted C2-C10heteroaryloxy group, a substituted or unsubstituted C2-C60heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7), and R40and R50may be each independently selected from a hydrogen, a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C7-C60arylalkyl group, a substituted or unsubstituted C1-C10heteroaryl group, a substituted or unsubstituted C2-C60heteroaryloxy group, a substituted or unsubstituted C2-C10heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7).

R40and R50may be each independently a hydrogen, a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C10alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C60aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C7-C60arylalkyl group, a substituted or unsubstituted C1-C10heteroaryl group, a substituted or unsubstituted C2-C10heteroaryloxy group, a substituted or unsubstituted C2-C60heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7).

a1, a2, a3, a4 and a5 in Formulae 2-5 respectively denote the number of R10(s), R20(s), R30(s), R40(s) and R50(s), and may each independently be an integer of 0 to 10.

When a1 is 2 or more, two or more R10(s) are the same or different; when a2 is 2 or more, two or more R20(s) are the same or different; when a3 is 2 or more, two or more R30(s) are the same or different; when a4 is 2 or more, two or more R40(s) are the same or different; and when a5 is 2 or more, two or more R50(s) are the same or different.

Each of * and *′ in Formulae 2 to 5 is a binding site to a neighboring atom.

According to an embodiment, in Formula 1, Ar1may be selected from groups represented by Formulae 2-1 to 2-6 and Ar2may be selected from groups represented by Formulae 3-1 to 3-7, but embodiments are not limited thereto:

In Formulae 2-1 to 2-6 and 3-1 to 3-7,

X1may be C(R17)(R1), N(R19), O or S,

X2may be C(R27)(R28), N(R29), O or S,

descriptions of R1to R4are the same as provided herein,

descriptions of R11to R19are the same as the description of R10,

descriptions of R21to R29are the same as the description of R20,

descriptions of R31to R34are the same as the description of R30, and

* is a binding site to a neighboring atom.

For example, R1to R4, R11to R19, R21to R29and R31to R34in Formulae 2-1 to 2-6 and 3-1 to 3-7 may be each independently selected from

a hydrogen, a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group and a C1-C20alkoxy group,

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzooxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group and a pyridobenzothiazinyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzoimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group and a pyridobenzothiazinyl group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, —Si(Q31)(Q32)(Q33), —N(Q34)(Q35) and —B(Q36)(Q37); and

—Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7),

wherein Q1to Q7and Q31to Q37may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group.

In some embodiments, R1to R4, R11to R19, R21to R29and R31to R34in Formulae 2-1 to 2-6 and 3-1 to 3-7 may be each independently selected from

a hydrogen, a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

In some embodiments, R1to R4, R11to R19, R21to R29and R31to R34in Formulae 2-1 to 2-6 and 3-1 to 3-7 may be each independently selected from a hydrogen, a deuterium, a cyano group (CN), a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a cyano group (CN), a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a cyano group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, but embodiments are not limited thereto.

In some embodiments, X1in Formula 2-1 to 2-6 may be O or S, but embodiments are not limited thereto.

In some embodiments, X1and X2in Formulae 2-1 to 2-6 and Formulae 3-1 to 3-6 may each independently be O or S.

In some embodiments, Ar1may be the same as Ar2in Formula 1; or

each of CY2and CY3in Formula 3 may be a benzene group, but embodiments are not limited thereto.

In some embodiments, in Formula 1,

Ar1may be represented by Formula 2-1, Ar2may be represented by Formula 3-1;

Ar1may be represented by Formula 2-2, Ar2may be represented by Formula 3-2; or

Ar1may be represented by Formula 2-6, and Ar2may be represented by Formula 3-6, but embodiments are not limited thereto.

In some embodiments, L1may be the same as L2in Formula 1.

CY4and CY5in Formulae 4 and 5 may be each independently selected from a benzene group, a naphthalene group, a fluorene group, a carbazole group, a dibenzofuran group, and a dibenzothiophene group.

According to an embodiment, L1and L2may be each independently selected from groups represented by Formula 4.

For example, L1and L2may be each independently selected from groups represented by Formula 4, and L1may be different than L2.

Alternatively, L1and L2may be each independently selected from groups represented by Formula 4, and L1may be the same as L2.

According to an embodiment, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-3:

In Formulae 1-1 to 1-3,

descriptions of Ar1and Ar2are the same as provided herein,

descriptions of R41to R48are each independently the same as the description of R40, and

descriptions of R51to R54are each independently the same as the description of R50.

According to an embodiment, the condensed cyclic compound may be represented by Formula 1-1, but embodiments are not limited thereto.

R41to R48and R51to R54in Formulae 1-1 to 1-3 may be each independently selected from

a hydrogen, a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

In some embodiments, R41to R48and R51to R54in Formulae 1-1 to 1-3 may be each independently selected from

a hydrogen, a deuterium, a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, but embodiments are not limited thereto.

According to an embodiment, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-3, An in Formulae 1-1 to 1-3 may be selected from groups represented by Formulae 2-1 to 2-6, and Ar2may be selected from groups represented by Formulae 3-1 to 3-7.

In some embodiments, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-3, An in Formulae 1-1 to 1-3 may be selected from groups represented by Formulae 2-1 to 2-6, and Ar2may be selected from groups represented by Formulae 3-1 to 3-7,

R1to R4, R11to R19, R21to R29and R31to R34may be each independently selected from

a hydrogen, a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group and a C1-C20alkoxy group;

C1-C20alkyl group and C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

R41to R48and R51to R54may be each independently selected from

a hydrogen, a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl 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 spirobifluorenyl 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 carbazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group and a dibenzocarbazolyl group, each substituted with at least one selected from a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C2-C20alkenyl group, a C2-C20alkynyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group.

In some embodiments, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-3, and in Formulae 1-1 to 1-3, Ar1may be selected from groups represented by Formulae 2-1 to 2-6, and Ar2may be selected from groups represented by Formulae 3-1 to 3-7,

R1to R4, R11to R19, R21to R29and R31to R34may be each independently selected from

a hydrogen, a deuterium, a cyano group (CN), a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a cyano group (CN), a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a cyano group, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

R41to R48and R51to R54may be each independently selected from

a hydrogen, a deuterium, a C1-C20alkyl group and a C1-C20alkoxy group;

a C1-C20alkyl group and a C1-C20alkoxy group, each substituted with at least one selected from a deuterium, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group and a dibenzothiophenyl group, each substituted with at least one selected from a deuterium, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group and —Si(Q31)(Q32)(Q33); and
—Si(Q1)(Q2)(Q3),

wherein Q1to Q3and Q31to Q33may be each independently selected from a hydrogen, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a biphenyl group, a terphenyl group and a naphthyl group, but embodiments are not limited thereto.

In some embodiments, the condensed cyclic compound may be represented by one of Formulae 1-1 to 1-3; in Formula 1-1 to 1-3, Ar1may be selected from groups represented by Formulae 2-1 to 2-6 and Ar2may be selected from groups represented by Formulae 3-1 to 3-7; and X1in Formulae 2-1 to 2-6 may be O or S (for example, X1and X2in Formulae 2-1 to 2-6 and 3-1 to 3-6 may each independently be O or S).

In some embodiments, the condensed cyclic compound may be represented by Formula 1-1, and in Formula 1-1, Ar1may be selected from groups represented by Formulae 2-1 to 2-6 and Ar2may be selected from groups represented by Formulae 3-1 to 3-7.

In some embodiments, the condensed cyclic compound may be represented by Formula 1-1; in Formula 1-1, Ar1may be selected from groups represented by Formulae 2-1 to 2-6 and Ar2may be selected from groups represented by Formulae 3-1 to 3-7; and X1in Formulae 2-1 to 2-6 may be O or S (for example, X1and X2in Formulae 2-1 to 2-6 and 3-1 to 3-6 may each independently be O or S).

The condensed cyclic compound may be selected from Compounds 1 to 108, but embodiments are not limited thereto:

At least one of L1and L2in Formula 1 may be selected from groups represented by Formula 4. In this regard, the condensed cyclic compound represented by Formula 1 may have steric hindrance, and thus have a high triplet energy value and excellent charge transfer characteristics. As a result, an electronic device including the condensed cyclic compound represented by Formula 1, for example, an organic light-emitting device, may have high efficiency and high luminance.

In some embodiments, in Formula 1, Ar1may be a group represented by Formula 2 and Ar2may be a group represented by Formula 3, and thus the condensed cyclic compound represented by Formula 1 may have excellent thermal stability. As a result, an electronic device including the condensed cyclic compound represented by Formula 1, for example, an organic light-emitting device, may have long lifespan.

R1to R4, R10, R20and R30in Formula 1 may be selected from a hydrogen, a deuterium, a hydroxyl group, a cyano group (CN), a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C60alkyl group, a substituted or unsubstituted C2-C60alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C6-C10aryloxy group, a substituted or unsubstituted C6-C10arylthio group, a substituted or unsubstituted C7-C10arylalkyl group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted C2-C60heteroaryloxy group, a substituted or unsubstituted C2-C10heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7), and R40and R50may be selected from a hydrogen, a deuterium, a hydroxyl group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C10alkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C60alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C6-C60aryloxy group, a substituted or unsubstituted C6-C10arylthio group, a substituted or unsubstituted C7-C10arylalkyl group, a substituted or unsubstituted C1-C10heteroaryl group, a substituted or unsubstituted C2-C10heteroaryloxy group, a substituted or unsubstituted C2-C10heteroarylthio group, a substituted or unsubstituted C3-C60heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q1)(Q2)(Q3), —N(Q4)(Q5), and —B(Q6)(Q7).

R1to R4, R10, R20, R30, R40and R50do not include “a halogen group including a fluoro group (—F)”, and thus the condensed cyclic compound represented by Formula 1 may have excellent heat resistance and thermal stability. Thus, when a thin film including the condensed cyclic compound represented by Formula 1 is formed through a deposition process, the condensed cyclic compound represented by Formula 1 may not decompose at a deposition temperature of a deposition process. As a result, an electronic device including the condensed cyclic compound represented by Formula 1, for example, an organic light-emitting device, may have long lifespan. In some embodiments, since R1to R4, R10, R20, R30, R40and R50may not include “a fluoro group (—F)”, “Ar1and Ar2” in Formula 1 may have an orbital contributing HOMO energy level, and “L1and L2” in Formula 1 may have an orbital contributing to LUMO energy level, and thus the orbital contributing to HOMO energy level and the orbital contributing to LUMO energy level may be separated and respectively distributed in moieties having different structures. As a result, the condensed cyclic compound represented by Formula 1 may have excellent charge transfer characteristics, and an electronic device including the condensed cyclic compound represented by Formula 1, for example, an organic light-emitting device, may present high efficiency.

For example, from the molecular orbital distribution of Compound 23 evaluated by using a Density Functional Theory (DFT) method including a Gaussian program structurally optimized at B3LYP/6-31G(d,p), it was found that B1and B3(an indolocarbazole ring) have an orbital contributing to HOMO energy level, and B2(a biphenylene group) has an orbital contributing to LUMO energy level. Thus the orbital contributing to HOMO energy level and the orbital contributing to LUMO energy level in a molecule of Compound 23 may be separated and respectively distributed in moieties having different structures.

For comparison, from the molecular orbital distribution of Compound A evaluated by using a DFT method including a Gaussian program structurally optimized at B3LYP/6-31G(d,p), it was found that A1(an indolocarbazole ring substituted with —F) may have an orbital contributing to HOMO energy level and A2(an indolocarbazole ring substituted with —F) may have an orbital contributing to LUMO energy level. Thus, the orbital contributing to HOMO energy level and the orbital contributing to LUMO energy level may be separated and respectively distributed in moieties having the same structures. Compound A having the aforementioned orbital distribution may have poor charge transfer characteristics, and thus an electronic device, including Compound A, for example, an organic light-emitting device, may have low luminescent efficiency.

Ph in Compound A denotes a phenyl group.

Each of R1to R4, R10, R20, R30, R40and R50may not have “a halogen atom” having high electron affinity, and thus the condensed cyclic compound represented by Formula 1 may have excellent hole transportation capability. As a result, an electronic device including the condensed cyclic compound represented by Formula 1, for example, an organic light-emitting device, may present high efficiency.

For example, HOMO, LUMO, and T1energy levels of Compounds 1 to 90 were evaluated through a simulation using a DFT method including a Gaussian program structurally optimized at B3LYP/6-31G(d,p). The results thereof are shown in Table 1 below:

TABLE 1Compound No.T1(eV)HOMO (eV)LUMO (eV)12.957−5.27−0.97222.924−5.285−1.14632.907−5.188−1.1242.835−5.328−1.25452.832−5.183−1.15762.984−5.255−1.19172.771−5.348−1.28182.78−5.204−1.21193.005−5.162−1.142102.892−5.249−1.137112.9−5.175−1.126122.87−5.292−1.196132.862−5.196−1.148142.802−5.286−1.299152.913−5.434−1.324162.801−5.133−1.199172.757−5.276−1.298182.919−5.26−1.154192.762−5.093−1.272202.97−5.214−1.16212.908−5.099−1.043222.824−5.012−1.199232.906−5.047−0.972242.824−4.894−1.016252.734−4.904−1.019272.967−4.975−1.038282.957−4.885−1.019292.679−4.86−1.057302.668−4.802−1.032312.966−5.035−1.024322.958−4.952−1.06332.96−5.249−1.015342.961−5.278−0.996352.906−5.168−1.083362.923−5.25−1.093372.84−5.251−1.135382.83−5.181−1.107392.982−5.238−1.202402.984−5.255−1.143412.78−5.266−1.189422.781−5.175−1.112433.013−5.236−1.084443.006−5.161−1.084452.908−5.174−1.08462.899−5.236−1.067472.873−5.252−1.107482.86−5.17−1.094492.808−5.207−1.176502.799−5.141−1.126512.919−5.257−1.101522.925−5.268−1.176532.762−5.2−1.206542.761−5.094−1.125552.972−5.207−1.107562.975−5.268−1.092572.923−5.006−0.955582.909−5.164−1.108592.824−4.919−1.042602.833−4.977−4.015612.744−4.821−1.03622.735−4.848−1.03632.974−4.965−1.042642.962−4.92−1.017652.683−4.846−1.07662.678−4.789−1.001672.966−4.926−1.028682.961−4.976−1.069692.967−5.07−1.041702.688−4.904−1.06712.835−5.059−1.06722.732−4.944−1.035732.913−5.13−1.155742.97−5.354−1.127752.757−5.267−1.275762.93−5.357−1.195772.806−5.286−1.264782.875−5.312−1.106803.008−5.307−1.112812.772−5.343−1.261822.984−5.383−1.151832.838−5.319−1.194842.925−5.32−1.114855.953−5.355−1.11863.006−5.308−1.153872.952−5.351−1.091882.97−5.363−1.18892.984−5.393−1.244902.969−5.029−1.04

Table 1 shows that Compounds 1 to 90 have excellent electric characteristics, for example, high T1energy level.

A method of synthesizing the condensed cyclic compound represented by Formula 1 may be understood by ordinary skill in the art by referring to Synthesis Examples.

In this regard, the condensed cyclic compound represented by Formula 1 may be suitable as a material of an organic layer of an organic light-emitting device, for example, a material for a hole transport layer, a material for an electron blocking layer and/or a host of an emission layer. According to another aspect, provided is an organic light-emitting device that includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer includes an emission layer, and

wherein the organic layer includes at least one of the condensed cyclic compounds represented by Formula 1.

While not wishing to be bound by theory, it is understood that when the organic light-emitting device includes the organic layer including the condensed cyclic compound represented by Formula 1 as described above, the organic light-emitting device has low driving voltage, high power efficiency, high luminous efficiency, high quantum luminance efficiency, and long lifespan.

For example, the condensed cyclic compound represented by Formula 1 may be included in the emission layer.

In some embodiments, the condensed cyclic compound represented by Formula 1 may be included in the emission layer, and the condensed cyclic compound represented by Formula 1 may be a material for delayed fluorescence.

According to an embodiment, the emission layer may include a host and a dopant (wherein an amount of the host is greater than an amount of the dopant), and the host may include the condensed cyclic compound represented by Formula 1. The condensed cyclic compound serving as a host may transfer energy to a dopant according to a delayed fluorescence emission mechanism. The dopant may include at least one of a fluorescent dopant and a phosphorescent dopant. The dopant may be selected from known dopants. The host may further include any suitable host selected from known hosts.

In some embodiments, the emission layer may include a host and a dopant (an amount of the host is greater than an amount of the dopant), and the dopant may include the condensed cyclic compound represented by Formula 1. The condensed cyclic compound as a dopant may emit delayed fluorescence according to a delayed fluorescence emission mechanism. The host may be selected from known dopants.

The emission layer may emit red, green or blue light.

According to an embodiment, the emission layer may be a blue emission layer including a phosphorescent dopant, but embodiments are not limited thereto.

In some embodiments, the condensed cyclic compound represented by Formula 1 may be included in a hole transport region.

For example, the hole transport region of the organic light-emitting device may include at least one of a hole transport layer and an electron blocking layer, and at least one of the hole transport layer and the electron blocking layer may include the condensed cyclic compound represented by Formula 1.

According to an embodiment, a hole transport region of the organic light-emitting device may include a hole transport layer, and the hole transport layer may include the condensed cyclic compound represented by Formula 1.

In some embodiments, a hole transport region of the organic light-emitting device may include an electron blocking layer, and the electron blocking layer may include the condensed cyclic compound represented by Formula 1. The electron blocking layer may directly contact the emission layer.

The expression as used herein “(an organic layer) includes at least one condensed cyclic compound” may be understood as “(organic layer) may include one condensed cyclic compound represented by Formula 1 or two or more different condensed cyclic compounds represented by Formula 1”.

For example, the organic layer may include only Compound 1 as the condensed cyclic compound. In this regard, Compound 1 may be included in the emission layer of the organic light-emitting device. Alternatively, the organic layer may include Compound 1 and Compound 2 as the condensed cyclic compounds. In this regard, Compound 1 and Compound 2 may be included in the same layer (for example, both Compound 1 and Compound 2 may be included in the emission layer), or in different layers (for example, Compound 1 may be included in the emission layer and Compound 2 may be included in the electron blocking layer).

The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode.

Alternatively, the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

For example, in the organic light-emitting device,

the first electrode may be an anode,

the second electrode may be a cathode, and

the organic layer may include a hole transport region disposed between the first electrode and the emission layer,

wherein an electron transport region may be disposed between the emission layer and the second electrode,

the hole transport region may include at least one selected from a hole injection layer, a hole transport layer and an electron blocking layer, and

the electron transport region may include at least one selected from a hole blocking layer, an electron transport layer and an electron injection layer.

As used herein, the term the “organic layer” refers to a single and/or a plurality of layers disposed between the first electrode and the second electrode in an organic light-emitting device. The “organic layer” may include not only organic compounds but also organometallic complexes including metals.

FIG.1is a schematic view of an organic light-emitting device10according to an embodiment of the present disclosure. Hereinafter, a structure and a method of manufacturing an organic light-emitting device according to an embodiment of the present disclosure will be described with reference toFIG.1. The organic light-emitting device10includes a first electrode11, an organic layer15, and a second electrode19, which are sequentially layered in the stated order.

A substrate may be additionally disposed under the first electrode11or on the second electrode19. The substrate may be a conventional substrate that is used in an organic light-emitting device, such as glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water repellency.

The first electrode11may be formed by vacuum-depositing or sputtering a material for forming the first electrode11on the substrate. The first electrode11may be an anode. The material for the first electrode11may be selected from materials with a high work function for easy hole injection. The first electrode11may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for the first electrode11may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). Alternatively, a metal such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag) may be used herein.

The first electrode11may have a single layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode11may have a triple-layer structure of ITO/Ag/ITO, but embodiments are not limited thereto.

The organic layer15is disposed on the first electrode11.

The organic layer15may include a hole transport region, an emission layer, and an electron transport region.

The hole transport region may be disposed between the first electrode11and the emission layer.

The hole transport region may include at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

The hole transport region may only include a hole injection layer or a hole transport layer. Alternatively, the hole transport region may include a structure in which a hole injection layer/a hole transport layer or a hole injection layer/a hole transport layer/an electron blocking layer are sequentially layered on the first electrode11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode11by using various methods such as vacuum-deposition, spin coating, casting, and a Langmuir-Blodgett (LB) method.

When a hole injection layer is formed by vacuum-deposition, though the conditions may vary depending on a compound that is used as a hole injection material and a structure and thermal properties of a desired hole injection layer, for example, the vacuum-deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10−8to about 10−3torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, but embodiments are not limited thereto.

When a hole injection layer is formed by spin coating, though the conditions may vary depending on a compound that is used as a hole injection material and a structure and thermal properties of a desired hole injection layer, the spin coating may be performed at a coating rate in a range of about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and at a temperature in a range of about 80° C. to 200° C. for removing a solvent after the spin coating, but embodiments are not limited thereto.

The conditions for forming a hole transport layer and an electron blocking layer may be inferred based on the conditions for forming the hole injection layer.

The hole transport region may include at least one selected from m-MTDATA, TDATA, 2-TNATA, NPB, p-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (Pani/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphor sulfonic acid (Pani/CSA), (polyaniline)/poly(4-styrenesulfonate) (PANI/PSS), a compound represented by Formula 201 below, and a compound represented by Formula 202 below:

Ar101and Ar102in Formula 201 may be each independently selected from

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group and a pentacenylene group; and

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group and a pentacenylene group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10alkyl group, a C2-C10alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C7-C60arylalkyl group, a C1-C60heteroaryl group, a C2-C60heteroaryloxy group, a C2-C60heteroarylthio group, a C3-C10heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group.

xa and xb in Formula 201 may each independently be an integer of 0 to 5, or may be 0, 1 or 2. For example, xa may be 1 and xb may be 0, but embodiments are not limited thereto.

R101to R108, R111to R119and R121to R124in Formulae 201 and 202 may be each independently selected from

a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, etc.) and a C1-C60alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, butoxy group, a pentoxy group, etc.);

a C1-C60alkyl group and a C1-C60alkoxy group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof and a phosphoric acid group or a salt thereof;

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group and a pyrenyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10alkyl group and a C1-C10alkoxy group,

but embodiments are not limited thereto.

R109in Formula 201 may be selected from

a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group; and

a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group, each substituted with at least one selected from a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20alkyl group, a C1-C20alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group and a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:

Descriptions of R101, R111, R112and R109in Formula 201A are the same as provided herein.

For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include Compounds HT1 to HT20, but embodiments are not limited thereto:

In some embodiments, the hole transport layer may include the condensed cyclic compound represented by Formula 1.

A thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may further include, in addition to the mentioned materials above, a charge-generating material to improve conductive properties. The charge-generating material may be homogeneously or non-homogeneously dispersed throughout the hole transport region.

The charge-generating material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenum oxide; and a compound containing a cyano group, such as Compound HT-D1 and HP-1, but embodiments are not limited thereto.

The hole transport region may further include a buffer layer.

The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.

An emission layer may be formed on the hole transport region by using various methods, such as vacuum-deposition, spin coating, casting, or an LB method. When the emission layer is formed by vacuum-deposition or spin coating, vacuum-deposition and coating conditions for the emission layer may be generally similar to the conditions for forming a hole injection layer, though the conditions may vary depending on the compound used.

The hole transport region may further include an electron blocking layer. The electron blocking layer may include a known material, for example, mCP, but embodiments are not limited thereto.

In some embodiments, the hole transport region may include an electron blocking layer, and the electron blocking layer may include the condensed cyclic compound represented by Formula 1.

A thickness of the electron blocking layer may be in a range of about 50 Å to about 1,000 Å, for example, about 70 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron blocking layer is within this range, excellent electron blocking characteristics may be obtained without a substantial increase in driving voltage.

When the organic light-emitting device is a full color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. Alternatively, the emission layer may have a structure in which the red emission layer, the green emission layer, and/or the blue emission layer are layered to emit white light or other various embodiments are possible.

The emission layer may include the condensed cyclic compound represented by Formula 1. For example, the emission layer may only include the condensed cyclic compound represented by Formula 1. In some embodiments, the emission layer may include a host and a dopant, and the host may include the condensed cyclic compound represented by Formula 1. In some embodiments, the emission layer may include a host and a dopant, and the dopant may include the condensed cyclic compound represented by Formula 1.

According to an embodiment, a dopant in the emission layer may be a phosphorescent dopant, and the phosphorescent dopant may include an organometallic compound represented by Formula 81:

In Formula 81,

M may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), palladium (Pd) and thulium (Tm),

Y81to Y84may each independently be carbon (C) or nitrogen (N),

Y81and Y82may be linked to each other by a single bond or a double bond, and Y83and Y84may be linked to each other by a single bond or a double bond,

CY81and CY82may be each independently selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isooxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzoimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group or a dibenzothiophene group, and CY81and CY82may be optionally further linked to each other by an organic linking group,

R81and R82may be each independently selected from a hydrogen, a deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF5, a substituted or unsubstituted C1-C10alkyl group, a substituted or unsubstituted C2-C60alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C10alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C6-C10aryloxy group, a substituted or unsubstituted C6-C10arylthio group, a substituted or unsubstituted C7-C10arylalkyl group, a substituted or unsubstituted C1-C10heteroaryl group, a substituted or unsubstituted C2-C60heteroaryloxy group, a substituted or unsubstituted C2-C10heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q1)(Q2), —Si(Q3)(Q4)(Q5), and —B(Q6)(Q7),

a81 and a82 may each independently be an integer of 1 to 5,

n81 may be an integer of 0 to 4,

n82 may be 1, 2 or 3,

L81may be a monovalent organic ligand, a divalent organic ligand or a trivalent organic ligand, and

descriptions for Q1to Q7are same as descriptions for Q1to Q3in —Si(Q1)(Q2)(Q3) in Formula 1.

Descriptions of R81and R82are the same as the description of R11.

The phosphorescent dopant may include at least one selected from Compounds PD1 to PD78 or Flr6, but embodiments are not limited thereto:

In some embodiments, the phosphorescent dopant may include PtOEP:

When the emission layer includes a host and a dopant, an amount of the dopant may be selected from a range of about 0.01 part by weight to about 20 parts by weight based on about 100 parts by weight of the host, but embodiments are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Then, an electron transport region may be disposed on the emission layer.

The electron transport region may include at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer, but is not limited thereto.

For example, the electron transport region may have a structure of a hole blocking layer/an electron transport layer/an electron injection layer or an electron transport layer/an electron injection layer, but it is not limited thereto. The electron transport layer may have a single layer structure or a multi-layer structure including two or more different materials.

The conditions for forming a hole blocking layer, an electron transport layer, and an electron injection layer, of the electron transport region, may be inferred based on the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may, for example, include at least one of BCP and Bphen, but is not limited thereto.

A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within this range, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include at least one selected from BCP, BPhen, Alq3, BAlq, TAZ, and NTAZ.

In some embodiments the electron transport layer may include at least one selected from Compounds ET1, ET2 and ET3, but it is not limited thereto.

A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within this range, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a metal-containing material in addition to the materials described 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 an electron injection layer (EIL) that facilitates electron injection from the second electrode19.

The electron injection layer may include at least one selected from LiQ, LiF, NaCl, CsF, Li2O, and BaO.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within this range, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode19is disposed on the organic layer15. The second electrode19may be a cathode. A material for the second electrode19may be a material having a relatively low work function, such as a metal, an alloy, an electrically conductive compound, and a mixture thereof. Detailed examples of the material for forming the second electrode19are lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). Alternatively, ITO or IZO may be used to form a transmissive second electrode19to manufacture a top emission light-emitting device, and such a variation may be possible.

According to an embodiment, the organic layer15of the organic light-emitting device10may include a hole transport region and an emission layer, and the hole transport region and the emission layer may include the condensed cyclic compound represented by Formula 1, wherein the condensed cyclic compound represented by Formula 1 included in the hole transport region may be the same as the condensed cyclic compound represented by Formula 1 included in the emission layer.

In some embodiments, the organic layer15of the organic light-emitting device10may include a hole transport region and an emission layer, and the hole transport region and the emission layer may include the condensed cyclic compound represented by Formula 1, wherein the condensed cyclic compound represented by Formula 1 included in the hole transport region may be different than the condensed cyclic compound represented by Formula 1 included in the emission layer.

Here, the hole transport region may include at least one of a hole transport layer and an electron blocking layer, and the condensed cyclic compound represented by Formula 1 may be included in:

i) the hole transport layer,

ii) the electron blocking layer or

iii) the hole transport layer and the electron blocking layer. The electron blocking layer may directly contact the emission layer.

Hereinbefore, an organic light-emitting device has been described with reference toFIG.1, but embodiments are not limited thereto.

A C1-C60alkyl group as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms. Detailed examples thereof are a methyl group, an ethyl group, a propyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. A C1-C10alkylene group as used herein refers to a divalent group having the same structure as a C1-C60alkyl group.

A C1-C60alkoxy group as used herein refers to a monovalent group represented by —OA101(wherein A101is the C1-C60alkyl group). Detailed examples thereof are a methoxy group, an ethoxy group, and an isopropyloxy group.

A C2-C10alkenyl group as used herein refers to a group formed by substituting at least one carbon-carbon double bond in the middle or at the terminal of the C2-C10alkyl group. Detailed examples thereof are an ethenyl group, a propenyl group, and a butenyl group. A C2-C10alkenylene group as used herein refers to a divalent group having the same structure as a C2-C10alkenyl group.

A C2-C60alkynyl group as used herein refers to a group formed by substituting at least one carbon-carbon triple bond in the middle or at the terminal of the C2-C10alkyl group. Detailed examples thereof are an ethynyl group and a propynyl group. A C2-C10alkynylene group as used herein refers to a divalent group having the same structure as a C2-C10alkynyl group.

A C3-C10cycloalkyl group as used herein refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms. Detailed examples thereof are a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. A C3-C10cycloalkylene group as used herein refers to a divalent group having the same structure as a C3-C10cycloalkyl group.

A C1-C10heterocycloalkyl group as used herein refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom and 1 to 10 carbon atoms. Detailed examples thereof are a tetrahydrofuranyl group and a tetrahydrothiophenyl group. A C1-C10heterocycloalkylene group as used herein refers to a divalent group having the same structure as a C1-C10heterocycloalkyl group.

A C3-C10cycloalkenyl group as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one double bond in its ring, and which is not aromatic. Detailed examples thereof are a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. A C3-C10cycloalkenylene group as used herein refers to a divalent group having the same structure as a C3-C10cycloalkenyl group.

A C1-C10heterocycloalkenyl group as used herein refers to a monovalent monocyclic group including at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Detailed examples of the C1-C10heterocycloalkenyl group are a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. A C2-C10heterocycloalkenylene group as used herein refers to a divalent group having the same structure as a C1-C10heterocycloalkenyl group.

A C6-C10aryl group as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C6-C10arylene group as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Detailed examples of the C6-C10aryl group are a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C6-C60aryl group and the C6-C10arylene group each include two or more rings, the rings may be fused to each other.

A C1-C10heteroaryl group as used herein refers to a monovalent group having a cyclic aromatic system including at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 60 carbon atoms. A C1-C10heteroarylene group as used herein refers to a divalent group having a cyclic aromatic system including at least one heteroatom selected from N, O, P, Si and S as a ring-forming atom and 1 to 60 carbon atoms. Detailed examples of the C1-C10heteroaryl 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 C1-C60heteroaryl group and the C1-C10heteroarylene group each include a plurality of rings, the rings may be fused to each other.

A C6-C10aryloxy group as used herein indicates —OA102(wherein A102is the C6-C60aryl group), a C6-C10arylthio group as used herein indicates —SA103(wherein A103is the C6-C60aryl group), and a C7-C60arylalkyl group as used herein indicates -A104A105(wherein A105is the C6-C59aryl group and A104is the C1-C53alkyl group).

A C2-C10heteroaryloxy group as used herein indicates —OA106(wherein A106is the C2-C60heteroaryl group), a C2-C10heteroarylthio group as used herein indicates —SA107(wherein A107is the C2-C10heteroaryl group), and a C3-C60heteroarylalkyl group as used herein indicates -A108A109(wherein A109is the C2-C59heteroaryl group and A108is the C1-C58alkyl group).

A monovalent non-aromatic condensed polycyclic group as used herein refers to a monovalent group that has two or more rings condensed to each other, and only carbon atoms (for example, the number of carbon atoms may be in a range of 8 to 60) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic in the entire molecular structure. Detailed examples of the non-aromatic condensed polycyclic group include a fluorenyl group. A divalent non-aromatic condensed polycyclic group as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

A monovalent non-aromatic condensed hetero-polycyclic group as used herein refers to a monovalent group that has a plurality of rings condensed with each other, has a heteroatom selected from N, O P, Si and S, other than carbon atoms (for example, the number of carbon atoms may be in a range of 1 to 60), as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic in the entire molecular structure. The monovalent non-aromatic condensed heteropolycyclic group includes a carbazolyl group. A divalent non-aromatic condensed hetero-polycyclic group as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed hetero-polycyclic group.

In Formula 1, at least one substituent of the substituted C1-C10alkyl group, substituted C2-C10alkenyl group, substituted C2-C10alkynyl group, substituted C3-C10cycloalkyl group, substituted C1-C10heterocycloalkyl group, substituted C3-C10cycloalkenyl group, substituted C1-C10heterocycloalkenyl group, substituted C6-C60aryl group, substituted C6-C60aryloxy group, substituted C6-C60arylthio group, substituted C7-C610arylalkyl group, substituted C1-C60heteroaryl group, substituted C2-C60heteroaryloxy group, substituted C2-C10heteroarylthio group, substituted C3-C60heteroarylalkyl group, substituted monovalent non-aromatic condensed polycyclic group and substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from

a deuterium, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10alkyl group, a C2-C10alkenyl group, a C2-C60alkynyl group and a C1-C10alkoxy group;

a C1-C60alkyl group, a C2-C60alkenyl group, a C2-C60alkynyl group and a C1-C60alkoxy group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C10aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C7-C10arylalkyl group, a C1-C6heteroaryl group, a C2-C60heteroaryloxy group, a C2-C10heteroarylthio group, a C3-C10heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q11)(Q12)(Q13), —N(Q14)(Q15) and —B(Q16)(Q17);

a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C7-C60arylalkyl group, a C1-C60heteroaryl group, a C2-C60heteroaryloxy group, a C2-C10heteroarylthio group, a C3-C10heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group;

a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C10aryl group, a C6-C10aryloxy group, a C6-C60arylthio group, a C7-C60arylalkyl group, a C1-C60heteroaryl group, a C2-C60heteroaryloxy group, a C2-C10heteroarylthio group, a C3-C10heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from a deuterium, —CD3, —CD2H, —CDH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C10alkyl group, a C2-C10alkenyl group, a C2-C60alkynyl group, a C1-C60alkoxy group, a C3-C10cycloalkyl group, a C1-C10heterocycloalkyl group, a C3-C10cycloalkenyl group, a C1-C10heterocycloalkenyl group, a C6-C60aryl group, a C6-C60aryloxy group, a C6-C60arylthio group, a C7-C60arylalkyl group, a C1-C60heteroaryl group, a C2-C10heteroaryloxy group, a C2-C10heteroarylthio group, a C3-C60heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q21)(Q22)(Q23), —N(Q24)(Q25) and —B(Q26)(Q27); and

—Si(Q31)(Q32)(Q33), —N(Q34)(Q35) and —B(Q36)(Q37), and

Q1to Q7, Q11to Q17, Q21to Q27and Q31to Q37may be each independently selected from a hydrogen, a deuterium, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C1-C10alkyl group, a substituted or unsubstituted C2-C10alkenyl group, a substituted or unsubstituted C2-C10alkynyl group, a substituted or unsubstituted C1-C10alkoxy group, a substituted or unsubstituted C3-C10cycloalkyl group, a substituted or unsubstituted C1-C10heterocycloalkyl group, a substituted or unsubstituted C3-C10cycloalkenyl group, a substituted or unsubstituted C1-C10heterocycloalkenyl group, a substituted or unsubstituted C6-C10aryl group, a substituted or unsubstituted C6-C10aryloxy group, a substituted or unsubstituted C6-C60arylthio group, a substituted or unsubstituted C7-C10arylalkyl group, a substituted or unsubstituted C1-C60heteroaryl group, a substituted or unsubstituted C2-C60heteroaryloxy group, a substituted or unsubstituted C2-C10heteroarylthio group, a substituted or unsubstituted C3-C10heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting “substituted” group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group and the carbon atoms (if any) contained in the substituent. For example, when the term “substituted C1-C10alkyl” refers to a C1-C60alkyl group substituted with C6-C10aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C7-C120.

The term “a biphenyl group” as used herein refers to a monovalent group in which two benzene rings are linked to each other by a single bond.

The term “a terphenyl group” as used herein refers to a monovalent group in which three benzene rings are linked to each other by a single bond.

Hereinafter, a compound and an organic light-emitting device according to an embodiment of the present disclosure will be described in detail with reference to Synthesis Examples and Examples. However, the present disclosure is not limited thereto. The expression “B was used instead of A” used in describing Synthesis Examples means that an amount of B used was identical to an amount of A used based on molar equivalence.

EXAMPLE

Synthesis Example 1: Synthesis of Compound 86

Synthesis of Intermediate 86-2

6.24 grams (g) (24.26 millimoles (mmol)) of 5H-benzofuro[3,2-c]carbazole was added to 80 milliliters (ml) of DMF and then 1.16 g (29.11 mmol) of NaH (60% dispersion in mineral oil) was added thereto at 0° C. The resulting mixture was stirred at room temperature for an hour. Then, 5.52 g (31.53 mmol) of 1-bromo-2-fluorobenzene was added thereto and stirred for 18 hours while being heated at 150° C. 100 ml of ethyl acetate was added thereto, and then the result was cleaned with 100 ml of water twice and dried with MgSO4. Then, ethyl acetate was removed therefrom by using a rotavapor to obtain a viscous product. The product was purified by silica gel column chromatography to obtain 7.6 g of Intermediate 86-2. The identity of obtained Intermediate 86-2 was confirmed by LC-MS.

Synthesis of Intermediate 86-1

11.35 g (27.53 mmol) of Intermediate 86-2 was melted with 92 ml of anhydrous THF and then 1.6 molar (M) (20.6 ml) of n-BuLi was slowly added thereto at −78° C. for an hour. After a 3-hour reaction, 8.80 g (46.80 mmol) of triisopropyl borate was added thereto and a reaction temperature was slowly increased to room temperature. Then, 1 normal (N) (10 ml) of HCl was added thereto, and the resultant was stirred for 2 hours. A solvent was removed by using a rotavapor, and the resultant was melted by adding 200 ml of methylene chloride thereto and cleaned with 100 ml of water twice, thereby obtaining a white solid. Slurry treatments by using 1 liter (L) of hexane and 1 L of MeOH were respectively performed on the white solid to obtain 6.5 g of Intermediate 86-1. The identity of obtained Intermediate 86-1 was confirmed by LC-MS.

C24H16BNO3: [M+H]=377.09

Synthesis of Compound 86

3.92 g of Intermediate 86-2, 4.34 g of Intermediate 86-1, 0.41 g (0.44 mmol) of Pd(PPh3)4and 2.45 g (17.71 mmol) of K2CO3were mixed with 35 ml/5 ml of THF/H2O, and the result was stirred for 18 hours while being heated at 80° C. The result was precipitated/stirred/filtered with 500 ml of MeOH to obtain a solid compound, and the solid compound was purified by silica gel column chromatography to obtain 3.9 g of Compound 86. The identity of obtained Compound 86 was confirmed by LC-MS.

C48H28N2O2: [M+H]=664.54

Synthesis Example 2: Synthesis of Compound 87

Compound 87 was synthesized in the same manner as in Synthesis Example 1, except that, when synthesizing Intermediate 86-2, 12H-benzofuro[2,3-a]carbazole was used instead of 5H-benzofuro[3,2-c]carbazole. The synthesized Compound was confirmed by LC-MS.

Synthesis Example 3: Synthesis of Compound 88

Compound 88 was synthesized in the same manner as in Synthesis Example 1, except that, when synthesizing Intermediate 86-2, 5H-benzo[4,5]thieno[3,2-c]carbazole was used instead of 5H-benzofuro[3,2-c]carbazole. The synthesized Compound was confirmed by LC-MS.

C48H28N2S2: [M+H]=696.12

Synthesis Example 4: Synthesis of Compound 89

Compound 89 was synthesized in the same manner as in Synthesis Example 1, except that, when synthesizing Intermediate 86-2, 12H-benzofuro[3,2-a]carbazole was used instead of 5H-benzofuro[3,2-c]carbazole. The synthesized Compound was confirmed by LC-MS.

C48H28N2O2: [M+H]=664.62

Synthesis Example 5: Synthesis of Compound 27

4.05 g of Ni(COD)2, 1.59 g of COD, and 2.30 g of bi-pyridyl were mixed with 24 ml of DMF and the resultant was heated to 85° C. and stirred for 30 minutes. Then, a mixture of 5 ml of toluene and 4.78 g of Intermediate 27-1 was slowly added thereto and the resultant was heated and stirred for 3 hours. Then, a mixture of conc. HCl/MeOH/acetone (1/1/1) was slowly added thereto to form a precipitate, the precipitate was filtered using a paper and cleaned with MeOH to obtain a solid compound, and the solid compound was subjected to silica hot filtering using xylene and recrystallization with dichloromethane/xylene to obtain 5.50 g of Compound 27. The obtained Compound 27 was confirmed by LC-MS.

C60H38N4: [M+H]=814.30

Synthesis Example 6: Synthesis of Compound 32

Compound 32 was synthesized in the same manner as in Synthesis Example 5, except that 5-(2-bromophenyl)-12-phenyl-5,12-dihydroindolo[3,2-a]carbazole was used instead of Intermediate 27-1. The synthesized Compound was confirmed by LC-MS.

C60H38N4: [M+H]=814.34

Synthesis Example 7: Synthesis of Compound 80

Compound 80 was synthesized in the same manner as in Synthesis Example 1, except that, when synthesizing Compound 86, (2-(9H-carbazol-9-yl)phenyl)boronic acid was used instead of Intermediate 86-1. The synthesized Compound was confirmed by LC-MS.

C42H26N20: [M+H]=574.18

Synthesis Example 8: Synthesis of Compound 91

Compound 91 was synthesized in the same manner as in Synthesis Example 1, except that, when synthesizing Compound 86, (2-(5H-benzo[4,5]thieno[3,2-c]carbazol-5-yl)phenyl)boronic acid was used instead of Intermediate 86-1. The synthesized Compound was confirmed by LC-MS.

C48H28N2OS: [M+H]=680.14

Synthesis Example 9: Synthesis of Compound 97

Compound 97 was synthesized in the same manner as in Synthesis Example 5, except that 5-(2-bromophenyl)-12,12-dimethyl-5,12-dihydroindeno[1,2-c]carbazole was used instead of Intermediate 27-1. The synthesized Compound was confirmed by LC-MS.

C54H40N2: [M+H]=716.33

Example 1

A glass substrate having a thickness of 1,500 Å and an indium tin oxide (ITO) electrode as a first electrode (anode) thereon was sonicated with distilled water, and then further sonicated with iso-propyl alcohol, acetone, and methanol, and dried to be placed in a plasma cleaner. Next, the glass substrate was cleaned for 5 minutes by using oxygen plasma and then mounted on a vacuum deposition apparatus.

Compound HT3 and Compound HP-1 were co-deposited on the ITO electrode of the glass substrate to form a hole injection layer having a thickness of 100 Å, and Compound HT3 was deposited on the hole injection layer to form a hole transport layer having a thickness of 1,300 Å. mCP was deposited on the hole transport layer to form an electron blocking layer having a thickness of 150 Å, thereby forming a hole transport region.

Compound 86 (host) and Flr6 (dopant, 10 percent by weight (wt %)) were co-deposited on the hole transport region to form an emission layer having a thickness of 300 Å.

BCP was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and Compound ET3 and Liq were vacuum-deposited on the hole blocking layer to form an electron transport layer having a thickness of 250 Å. Liq was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å and an Al second electrode (cathode) having a thickness of 1,000 Å was formed on the electron injection layer, thereby manufacturing an organic light-emitting device.

Examples 2 to 9 and Comparative Example 1

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that when forming an emission layer, compounds shown in Table 2 were used instead of Compound 86.

Evaluation Example 1: Characteristic Evaluation of Organic Light-Emitting Device

Driving voltage, current density, luminous efficiency, power efficiency, quantum luminance efficiency and lifespan of each of the organic light-emitting devices manufactured in Examples 1 to 9 and Comparative Example 1 were measured by using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000 Å). The results thereof are shown in Table 2. T95(at 500 candelas per meter, cd/m2) in Table 2 refers to an amount of time until luminance was decreased to 95% of its initial luminance. In Table 2, the driving voltage, luminous efficiency, power efficiency, quantum luminance efficiency and lifespan of Examples 1 to 9 were expressed in a relative value compared to “100”, which denotes the driving voltage, luminous efficiency, power efficiency, quantum luminance efficiency and lifespan of Comparative Example 1.

TABLE 2quantumLuminousPowerluminancedriving voltageefficiencyefficiencyefficiencyhost(V)(cd/A)(lm/W)(%)T95(hr)Example 18689%114%128%113%256%Example 287105%105%108%104%142%Example 388101%129%128%129%167%Example 48998%109%116%111%120%Example 527107%104%108%103%103%Example 632101%120%118%117%123%Example 78087%117%115%112%208%Example 89195%122%128%121%212%Example 99799%117%114%115%93%ComparativeCompound B100%100%100%100%100%Example 1

Table 2 shows that the organic light-emitting devices of Examples 1 to 9 have lower or comparable driving voltage, higher luminous efficiency, higher power efficiency, higher quantum luminance efficiency and longer of comparable lifespan, compared to the organic light-emitting device of Comparative Example 1.

It should be understood that exemplary embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each exemplary embodiment should typically be considered as available for other similar features or aspects in other exemplary embodiments.

While one or more exemplary embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present inventive concept as defined by the following claims.