CONDENSED CYCLIC COMPOUND, ORGANIC LIGHT EMITTING DEVICE INCLUDING CONDENSED CYCLIC COMPOUND, AND ELECTRONIC APPARATUS INCLUDING ORGANIC LIGHT EMITTING DEVICE

Abstract

Provided are a condensed cyclic compound represented by one of Formulae 1 to 4, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the organic light-emitting device:

Description

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to Korean Patent Application Nos. 10-2021-0053284, filed on Apr. 23, 2021, and 10-2022-0032233, filed on Mar. 15, 2022, in the Korean Intellectual Property Office, the contents of which are incorporated herein in their entirety by reference.

BACKGROUND

1. Field

The present disclosure relates to a condensed cyclic compound, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the organic light-emitting device.

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emissive devices which produce full-color images. In addition, OLEDs have wide viewing angles and exhibit excellent driving voltage and response speed characteristics.

OLEDs include an anode, a cathode, and an organic layer between the anode and the cathode and including an emission layer. A hole transport region may be between the anode and the emission layer, and an electron transport region may be between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. The excitons may transition from an excited state to a ground state, thus generating light.

SUMMARY

Provided are a novel condensed cyclic compound, an organic light-emitting device including the condensed cyclic compound, and an electronic apparatus including the organic light-emitting device.

Additional aspects will be set forth in part in the description which follows and, in part, will be apparent from the description, or may be learned by practice of the presented embodiments.

According to an aspect, a condensed cyclic compound is represented by one of Formulae 1 to 4

wherein, in Formulae 1 to 4,

Y₁ is B, N, P, or P(═O),

A₁ to A₃ are each independently a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group,

X₁ is O, S, Se, N(R₁₀), C(R₁₀)(R₂₀), Si(R₁₀)(R₂₀), Ge(R₁₀)(R₂₀), or P(═O)(R₁₀),

X₂ is O, S, Se, N(R₃₀), C(R₃₀)(R₄₀), Si(R₃₀)(R₄₀), Ge(R₃₀)(R₄₀), or P(═O)(R₃₀),

X₃ is a single bond, O, S, Se, N(R₅₀), C(R₅₀)(R₆₀), Si(R₅₀)(R₆₀), Ge(R₅₀)(R₆₀), or P(═O)(R₅₀),

Ar₁ to Ar₇ are each independently a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

a1 to a5 are each 1, 2, or 3,

R₁ to R₅, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ are each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀ heteroarylthio 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), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b1 to b3 are each independently an integer from 1 to 10,

a substituent of the substituted C₅-C₃₀ carbocyclic group, the substituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group is

deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro 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, or a phosphoric acid group or a salt thereof,

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro 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-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or any combination thereof,

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or any combination thereof,

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), or —P(═O)(Q₃₈)(Q₃₉), or

any combination thereof,

wherein Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group.

According to an aspect of another embodiment, an organic light-emitting device may include: a first electrode, a second electrode, and an organic layer between the first electrode and the second electrode, wherein the organic layer may include at least one condensed cyclic compound.

According to an aspect of another embodiment, an electronic apparatus may include the organic light-emitting device.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawings in which:

The FIG. 1 is a schematic cross-sectional view of an organic light-emitting device according to an exemplary embodiment; and

FIGS. 2A to 2E show diagrams schematically illustrating an energy transfer process according to an exemplary embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. 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 on 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 herein.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. As used herein, “a,” “an,” “the,” and “at least one” do not denote a limitation of quantity, and are intended to cover both the singular and plural, unless the context clearly indicates otherwise. For example, “an element” has the same meaning as “at least one element,” unless the context clearly indicates otherwise.

“Or” means “and/or.” As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. 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.

Furthermore, relative terms, such as “lower” or “bottom” and “upper” or “top,” may be used herein to describe one element's relationship to another element as illustrated in the Figures. It will be understood that relative terms are intended to encompass different orientations of the device in addition to the orientation depicted in the Figures. For example, if the device in one of the figures is turned over, elements described as being on the “lower” side of other elements would then be oriented on “upper” sides of the other elements. The exemplary term “lower,” can therefore, encompasses both an orientation of “lower” and “upper,” depending on the particular orientation of the figure. Similarly, if the device in one of the figures is turned over, elements described as “below” or “beneath” other elements would then be oriented “above” the other elements. The exemplary terms “below” or “beneath” can, therefore, encompass both an orientation of above and below.

“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% or 5% of the stated value.

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this disclosure 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.

The condensed cyclic compound may be represented by one of Formulae 1 to 4:

wherein, in Formulae 1 to 4, Y₁ may be B, N, P, or P(═O).

For example, in Formulae 1 to 4, Y₁ may be B.

A₁ to A₃ in Formulae 1 to 4 may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group.

In an embodiment, A₁ to A₃ in Formulae 1 to 4 may each independently be a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a fluorene group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

For example, A₁ to A₃ may each independently be a benzene group.

In Formulae 1 to 4, X₁ may be O, S, Se, N(R₁₀), C(R₁₀)(R₂₀), Si(R₁₀)(R₂₀), Ge(R₁₀)(R₂₀), or P(═O)(R₁₀),

X₂ may be O, S, Se, N(R₃₀), C(R₃₀)(R₄₀), Si(R₃₀)(R₄₀), Ge(R₃₀)(R₄₀), or P(═O)(R₃₀), and X₃ may be a single bond, O, S, Se, N(R₅₀), C(R₅₀)(R₆₀), Si(R₅₀)(R₆₀), Ge(R₅₀)(R₆₀), or P(═O)(R₅₀).

In an embodiment, X₁ in Formula 1 may be O, S, N(R₁₀), or C(R₁₀)(R₂₀).

In an embodiment, X₁ in Formula 2 may be O, S, N(R₁₀), or C(R₁₀)(R₂₀), and X₂ may be O, S, N(R₃₀), or C(R₃₀)(R₄₀).

For example, in Formula 2, X₁ and X₂ may each be O; X₁ and X₂ may each be S; X₁ may be N(R₁₀), and X₂ may be N(R₃₀); or X₁ may be C(R₁₀)(R₂₀), and X₂ may be C(R₃₀)(R₄₀).

In an embodiment, X₃ in Formula 1 may be O, S, N(R₁₀), or C(R₁₀)(R₂₀).

In an embodiment, in Formula 4, X₁ may be O, S, N(R₁₀), or C(R₁₀)(R₂₀), and X₃ may be a single bond.

Ar₁ to Ar₇ in Formulae 1 to 4 may each independently be a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group.

In an embodiment, Ar₁ to Ar₇ in Formulae 1 to 4 may each be a substituted or unsubstituted C₆-C₆₀ arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In an embodiment, Ar₁ to Ar₇ in Formulae 1 to 4 may each independently be:

a cyclopentane group, a cyclohexane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, a pentalene group, an indene group, an azulene group, a heptalene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, or any combination thereof.

For example, Ar₁ to Ar₇ in Formulae 1 to 4 may each independently be a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, or a pyrazine group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, or any combination thereof.

In some embodiments, Ar₁ to Ar₇ in Formulae 1 to 4 may each independently be a benzene group unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a phenyl group, or any combination thereof.

In one or more embodiments, Ar₁ to Ar₅ in Formulae 1 to 3 may each independently be a group represented by one of Formulae Ar-1 to Ar-3, and Ar₆ and Ar₇ in Formula 4 may each independently be a group represented by Formula Ar-4:

wherein, in Formulae Ar-1 to Ar-4,

X₂₁ to X₂₄ may each independently be C or N,

Z₁ may be deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl 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, or a carbazolyl group,

d1 may be an integer from 0 to 4,

d2 may be an integer from 0 to 3, and

*, *′, and *″ each indicate a binding site to an adjacent atom.

In Formulae 1 to 3, a1 to a5 may each be 1, 2, or 3. When a1 is 2 or 3, two or three of Ar₁(s) may be identical to or different from each other, when a2 is 2 or 3, two or three of Ar₂(s) may be identical to or different from each other, when a3 is 2 or 3, two or three of Ar₃(s) may be identical to or different from each other, when a4 is 2 or 3, two or three of Ar₄(s) may be identical to or different from each other, and when a5 is 2 or 3, two or three of Ar₅(s) may be identical to or different from each other.

In an embodiment, in Formulae 1 to 3, a1 and a3 may each be 2, and a2, a4, and a5 may each be 1, but embodiments are not limited thereto.

In an embodiment, a moiety represented by

in Formula 4 may be represented by one of Formulae 4-1 to 4-4:

• • a. herein, in Formulae 4-1 to 4-4,

Z₁ and Z₂ may each independently be: deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl 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, or a carbazolyl group,

d2 and d3 may each independently be an integer from 0 to 3, and

R₁₀ and R₂₀ may respectively be understood by referring to the descriptions of R₂₁ and R₂₂ provided herein,

* and *′ each indicate a binding site to an adjacent atom.

R₁ to R₅, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ in Formulae 1 to 4 may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀ heteroarylthio 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), —B(Q₆)(Q₇), or —P(═O)(Qa)(Q₉).

b1 to b3 in Formulae 1 to 4 may each independently be an integer from 1 to 10. In Formulae 1 to 4, when b1 is 2 or greater, at least two R₁(s) may be identical to or different from each other, when b2 is 2 or greater, at least two R₂(s) may be identical to or different from each other, and when b3 is 2 or greater, at least two R₃(s) may be identical to or different from each other.

In an embodiment, R₁ to R₅, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ in Formulae 1 to 4 may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, or a phosphoric acid group or a salt thereof;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —N(Q₃₁)(Q₃₂), or any combination thereof.

a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, —N(Q₃₁)(Q₃₂), or any combination thereof; or

—N(Q₁)(Q₂),

wherein Q₁, Q₂, Q₃₄, and Q₃₅ may each independently be: a C₁-C₁₀ alkyl group; a alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀ alkyl group, a phenyl group, or any combination thereof.

In one or more embodiments, in Formulae 1 to 4, R₁ to R₅, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ may each independently be:

hydrogen, deuterium, —F, or a cyano group;

a C₁-C₂₀ alkyl group or a C₁-C₂₀ alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; 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 pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy 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 pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; or

—N(Q₁)(Q₂),

wherein Q₁ and Q₂ may each independently be: a C₁-C₁₀ alkyl group; a C₁-C₁₀ alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀ alkyl group, a phenyl group, or any combination thereof.

In some embodiments, in Formulae 1 to 4, R₁ to R₅, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ may each independently be hydrogen, deuterium, —F, a cyano group, an amidino group, a group represented by Formulae 9-1 to 9-19, or a group represented by Formulae 10-1 to 10-194:

wherein, in Formulae 9-1 to 9-19 and 10-1 to 10-194, * indicates a binding site to an adjacent atom, “Ph” represents a phenyl group, and “TMS” represents a trimethylsilyl group.

In one or more embodiments, the condensed cyclic compound may be represented by Formula 1A, Formula 2A, Formula 3A, or Formula 4A:

wherein, in Formulae 1A, 2A, 3A, and 4A,

Ar₁₁ and Ar₁₂ may each be understood by referring to the description of Ar₁ provided herein,

Ar₃₁ and Ar₃₂ may each be understood by referring to the description of Ar₃ provided herein, and

X₁, X₂, A₁ to A₃, Ar₁ to Ar₇, R₁ to R₅, and b1 to b3 may respectively be understood by referring to the descriptions of X₁, X₂, A₁ to A₃, Ar₁ to Ar₇, R₁ to R₅, and b1 to b3 provided herein.

In one or more embodiments, the condensed cyclic compound may be represented by Formula 1A-1, Formula 2A-1, Formula 3A-1, or Formula 4A-1:

wherein, in Formulae 1A-1, 2A-1, 3A-1, and 4A-1,

b11, b22, and b31 may each independently be an integer from 1 to 3,

b12 and b21 may each independently be an integer from 1 to 4,

b32 may be an integer of 1 or 2,

Ar₁₁ and Ar₁₁ may each be understood by referring to the description of Ar₁ provided herein,

Ar₃₁ and Ar₃₂ may each be understood by referring to the description of Ar₃ provided herein, and

X₁, X₂, Ar₁ to Ar₇, and R₁ to R₅ may respectively be understood by referring to the descriptions of X₁, X₂, Ar₁ to Ar₇, and R₁ to R₅ provided herein.

In an embodiment, in Formulae 1A-1 to 3A-1, Ar₁₁, Ar₁₂, Ar₂, Ar₃₁, Ar₃₂, Ar₄, and Ar₅ may each independently be a group represented by one of Formulae Ar-1 to Ar-3, and in Formula 4A-1, Ar₆ and Ar₇ may each independently be a group represented by Formula Ar-4.

In one or more embodiments, the condensed cyclic compound may be represented by Formula 1A-2, Formula 2A-2, Formula 3A-2, or Formula 4A-2:

wherein, in Formulae 1A-2, 2A-2, 3A-2, and 4A-2,

b11, b22, and b31 may each independently be an integer from 1 to 3,

b12 and b21 may each independently be an integer from 1 to 4,

b32 may be an integer of 1 or 2,

Z₁, Z₂ and Z₁₁ to Z₁₆ may each independently be deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀ alkyl group, a C₁-C₆₀ alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl 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, or a carbazolyl group,

d1 and d11 to d16 may each independently be an integer from 0 to 4,

d2 and d3 may each independently be an integer from 0 to 3, and

X₁, X₂, and R₁ to R₅ may respectively be understood by referring to the descriptions of X₁, X₂, and R₁ to R₅ provided herein.

For example, in Formulae 1A-2, 2A-2, 3A-2, and 4A-2, X₁ may be O, S, N(R₁₀), or C(R₁₀)(R₂₀), and X₂ may be O, S, N(R₃₀), or C(R₃₀)(R₄₀).

For example, a group represented by any one of Formulae 1 to 4 may be one of Compounds 1 to 40:

The condensed cyclic compound may include a structure of a polycyclic aromatic compound additionally linked with at least two rings of A₁ to A₃ bound to boron by a linker having a structure represented by —Ar—X—Ar′— (e.g., a linker having a structure of —(Ar₁)_a1—X₁—(Ar₂)_a2—) to the polycyclic aromatic compound. Accordingly, structural distortion of the condensed cyclic compound may be reduced to increase molecular stability, and radially bulky groups may be arranged about a central atom, Y₁, to increase molecular orientation. Accordingly, an organic light-emitting device including the condensed cyclic compound may have improved efficiency and improved lifespan.

The difference (ΔE_ST) between a triplet energy level (eV) and a singlet energy level (eV) of the condensed cyclic compound represented by one of Formulae 1 to 4 may be 0 eV or greater and 0.5 eV or less. Therefore, the condensed cyclic compound may emit delayed fluorescence of high efficiency. For example, the condensed cyclic compound may emit thermal activated delayed fluorescence (TADF).

When the difference between a triplet energy level (eV) and a singlet energy level (eV) of the condensed cyclic compound is within this range, up-conversion from a triplet state to a singlet state may occur effectively, and thus, the of the condensed cyclic compound may emit delayed fluorescence.

Here, the triplet energy level and the singlet energy level of the condensed cyclic compound may be evaluated according to density functional theory (DFT) method, wherein structure optimization is performed at a degree of MPWB95, and 6-31G(d,p), for example, according to the DFT method of the Gaussian program.

For example, the highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO), triplet (T₁), and singlet (S₁) energy levels of some of the condensed cyclic compounds represented by Formula 1 and a comparative compound were evaluated by using the Gaussian program according to a density functional theory (DFT) method (structure optimization is performed at a degree of B3LYP, and 6-31G(d,p)). The results thereof are shown in Tables 1 to 4.

In Tables 1 to 4, S1_vert (vertical excitation energy of S1) indicates a calculated energy value at excitation from a ground state to a singlet (S1) state of a compound.

In Tables 1 to 4, T1_vert (vertical excitation energy of T1) indicates a calculated energy value at excitation from a ground state to a triplet (T1) state of a compound.

In Tables 1 to 4, f indicates an oscillator strength value. f is proportional to a light absorption intensity of a molecule and represents a rate at which the molecule is excited by absorbing light.

TABLE 1
Compound	HOMO	LUMO	S1	T1	f (S1)	ΔEST
No.	(eV)	(eV)	(eV)	(eV)	@ S0	(eV)
1	−4.90	−1.47	2.97	2.56	0.46	0.40
2	−4.93	−1.49	2.97	2.57	0.46	0.40
3	−4.80	−1.38	2.97	2.57	0.53	0.40
4	−4.78	−1.31	3.00	2.59	0.48	0.41
5	−5.09	−1.67	2.98	2.58	0.48	0.40
6	−5.14	−1.63	3.05	2.64	0.48	0.41
7	−4.98	−1.45	3.07	2.65	0.54	0.42
8	−5.00	−1.49	3.05	2.65	0.49	0.41
9	−4.85	−1.43	2.97	2.56	0.44	0.41
10	−4.84	−1.35	3.02	2.60	0.44	0.42
11	−4.77	−1.35	2.98	2.57	0.47	0.41
12	−4.77	−1.33	2.99	2.57	0.44	0.41
13	−4.99	−1.54	3.00	2.59	0.53	0.40
14	−4.98	−1.47	3.03	2.62	0.54	0.41
15	−4.90	−1.38	3.04	2.63	0.56	0.41
16	−4.88	−1.39	3.02	2.61	0.53	0.41
17	−5.00	−1.48	3.06	2.64	0.44	0.42
18	−5.01	−1.49	3.06	2.64	0.44	0.42
19	−4.94	−1.40	3.07	2.65	0.47	0.42
20	−4.95	−1.46	3.04	2.62	0.46	0.42

TABLE 2
Compound	HOMO	LUMO	S1	T1	f (S1)	ΔEST
No.	(eV)	(eV)	(eV)	(eV)	@ S0	(eV)
21	−4.86	−1.48	2.94	2.51	0.35	0.43
22	−4.85	−1.41	2.97	2.54	0.36	0.43
23	−4.78	−1.39	2.94	2.52	0.33	0.42
24	−4.77	−1.30	2.98	2.56	0.35	0.43
25	−4.98	−1.57	2.96	2.54	0.43	0.42
26	−4.96	−1.51	2.99	2.56	0.45	0.42
27	−4.88	−1.42	2.99	2.57	0.42	0.42
28	−4.88	−1.40	3.01	2.59	0.44	0.42
29	−4.95	−1.50	2.99	2.56	0.45	0.43
30	−4.97	−1.51	2.99	2.56	0.45	0.43
31	−4.87	−1.42	2.98	2.56	0.44	0.42
32	−4.89	−1.41	3.01	2.58	0.44	0.42

TABLE 3
Compound	HOMO	LUMO	S1	T1	f (S1)	ΔEST
No.	(eV)	(eV)	(eV)	(eV)	@ S0	(eV)
33	−4.71	−1.38	2.83	2.48	0.27	0.35
34	−4.67	−1.47	2.75	2.36	0.30	0.39
35	−4.57	−1.26	2.82	2.46	0.29	0.36
36	−4.73	−1.15	3.11	2.69	0.31	0.42
37	−4.90	−1.53	2.88	2.52	0.26	0.36
38	−4.90	−1.55	2.85	2.48	0.29	0.37
39	−4.77	−1.40	2.87	2.50	0.28	0.37
40	−4.84	−1.48	2.86	2.49	0.29	0.37

TABLE 4
Compound	HOMO	LUMO	S1	T1	f (S1)	ΔEST
No.	(eV)	(eV)	(eV)	(eV)	@ S0	(eV)
CP1	−4.74	−1.19	3.05	2.62	0.28	0.43
CP2	−4.82	−1.29	3.04	2.63	0.28	0.41
CP3	−4.77	−1.16	3.10	2.66	0.26	0.44

In Tables 1 to 4, the condensed cyclic compound of the present disclosure was found to have excellent electrical characteristics and a high oscillator strength and a low ΔE_ST.

The condensed cyclic compound may be suitable for use as an organic layer material of an organic light-emitting device, for example, an emission layer material, a hole transport region material, and/or an electron transport region material of the organic layer.

Accordingly, according to an aspect of another embodiment, an organic light-emitting device may include: a first electrode; a second electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and at least one condensed cyclic compound.

Since the organic light-emitting device has an organic layer including the condensed cyclic compound, the organic light-emitting device may have a low driving voltage, high efficiency, high luminance, high quantum efficiency, and long lifespan.

In an embodiment, in the organic light-emitting device,

the first electrode may be an anode, the second electrode may be a cathode,

the organic layer may include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode,

wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and

the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof, but embodiments are not limited thereto.

In an embodiment, the condensed cyclic compound may be included in the emission layer of the organic light-emitting device.

In an embodiment, the emission layer in the organic light-emitting device may include a host and a dopant, wherein the dopant may include at least one condensed cyclic compound.

In some embodiments, the emission layer may emit delayed fluorescence. The delayed fluorescence may be fluorescence emitted from the condensed cyclic compound as a dopant.

The emission layer may emit red light, green light, or blue light. In some embodiments, the emission layer may emit blue light. The maximum emission wavelength of the blue light may be in a range of about 420 nm to about 500 nm, for example, about 440 nm to about 480 nm or about 450 nm to about 470 nm.

For example, the condensed cyclic compound may be included in at least one of the hole transport region and the electron transport region.

DESCRIPTION OF FIG. 1

FIG. 1 illustrates a schematic cross-sectional view of an organic light-emitting device 10 according to an exemplary embodiment. Hereinafter, a structure of an organic light-emitting device according to one or more embodiments and a method of manufacturing the organic light-emitting device will be described with reference to FIG. 1.

The organic light-emitting device 10 in FIG. 1 may include a first electrode 11, an organic layer 15, and a second electrode 19, which may be sequentially layered in this stated order.

A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. The substrate may be a conventional substrate used in organic light-emitting devices, e.g., a 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 electrode 11 may be produced by depositing or sputtering, onto the substrate, a material for forming the first electrode 11. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be a material with a high work function for easy hole injection.

The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), or zinc oxide (ZnO). In some embodiments, the material for forming the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), aluminum-lithium (A₁-Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag).

The first electrode 11 may have a single-layered structure or a multi-layered structure including a plurality of layers. In some embodiments, the first electrode 11 may have a triple-layered structure of ITO/Ag/ITO, but embodiments are not limited thereto.

Organic Layer 15

The organic layer 15 may be on the first electrode 11.

The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

Hole Transport Region in Organic Layer 15

The hole transport region may be between the first electrode 11 and the emission layer.

The hole transport region may include at least one of a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

The hole transport region may include a hole injection layer only or a hole transport layer only. In some embodiments, the hole transport region may include a hole injection layer and a hole transport layer which are sequentially stacked on the first electrode 11. In some embodiments, the hole transport region may include a hole injection layer, a hole transport layer, and an electron blocking layer, which are sequentially stacked on the first electrode 11.

When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) deposition.

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

When a hole injection layer is formed by spin coating, the spin coating may be performed at a 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. to facilitate removal of a solvent after the spin coating, though the conditions may vary depending on a compound used as a hole injection material and a structure and thermal properties of a desired hole injection layer, but embodiments are not limited thereto.

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

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

Formula 202, or any combination thereof:

wherein, in Formula 201, Ar₁₀₁ and Ar₁₀₂ may each independently be:

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 chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group; or

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 chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof.

In Formula 201, xa and xb may each independently be an integer from 0 to 5. In some embodiments, xa and xb may each independently be 0, 1, or 2. In some embodiments, xa may be 1, and xb may be 0, but embodiments are not limited thereto.

In Formulae 201 and 202, R₁₀₁ to R₁₀₈, R₁₁₁ to R₁₁₉, and R₁₂₁ to R₁₂₄ may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group (e.g., a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, or a hexyl group), or a C₁-C₁₀ alkoxy group (e.g., a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group);

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, or any combination thereof, substituted, a C₁-C₁₀ alkyl group, and a C₁-C₁₀ alkoxy group;

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

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, or a pyrenyl group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, or any combination thereof,

but embodiments are not limited thereto.

R₁₀₉ in Formula 201 may be:

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

a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, each substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or a combination thereof.

In some embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but embodiments are not limited thereto:

wherein, in Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ may respectively be understood by referring to the descriptions of R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉ provided herein.

In some embodiments, the compounds represented by Formulae 201 and 202 may include Compounds HT1 to HT20, but embodiments are not limited thereto:

The 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, a hole transport layer, or any combination thereof, 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, 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. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, excellent hole transport characteristics may be obtained without a substantial increase in driving voltage.

The hole transport region may include a charge generating material as well as the aforementioned materials, to improve conductive properties of the hole transport region. The charge generating material may be substantially homogeneously or non-homogeneously dispersed in the hole transport region.

The charge generating material may include, for example, a p-dopant. The p-dopant may include one of a quinone derivative, a metal oxide, and a compound containing a cyano group, but embodiments are not limited thereto. For example, non-limiting examples of the p-dopant include a quinone derivative, such as tetracyanoquinodimethane (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 or Compound HT-D2, 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 depending on a wavelength of light emitted from the emission layer to improve the efficiency of an organic light-emitting device.

The emission layer may be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, vacuum deposition and coating conditions for forming the emission layer may be generally similar to those conditions for forming a hole injection layer, though the conditions may vary depending on a compound that is used.

The hole transport region may further include an electron blocking layer. The electron blocking layer may include any suitable known material, e.g., mCP, but embodiments are not limited thereto:

The thickness of the electron blocking layer may be in a range of about 50 Å to about 1,000 Å, and in some embodiments, about 70 Å to about 500 Å. When the thickness of the electron blocking layer is within any of these ranges, excellent electron blocking characteristics may be obtained without a substantial increase in driving voltage.

Emission Layer in Organic Layer 15

When the organic light-emitting device 10 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. In some embodiments, 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. In some embodiments, the structure of the emission layer may vary.

The emission layer may include the condensed cyclic compound represented by one of Formulae 1 to 4.

The emission layer may include the condensed cyclic compound represented by one of Formulae 1 to 4 only.

In some embodiments, the emission layer may include a host and a dopant, and the dopant may include the condensed cyclic compound represented by one of Formulae 1 to 4.

When the emission layer includes the host and the dopant, an amount of the dopant may be a range of about 0.01 parts to about 20 parts by weight based on about 100 parts by weight of the emission layer, but embodiments are not limited thereto. When the amount of the dopant is within this range, light emission without quenching may be realized.

The thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 200 Å to about 600 Å. When the thickness of the emission layer is within any of these ranges, improved luminescence characteristics may be obtained without a substantial increase in driving voltage.

Next, an electron transport region may be formed on the emission layer.

First Embodiment—Descriptions of FIG. 2A

In the First Embodiment, the condensed cyclic compound may be a fluorescence emitter. According to the First Embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host A’, and Host A may not be identical to the condensed cyclic compound). Host A may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto. Host A may be a fluorescent host.

General energy transfer of the First Embodiment may be explained according to FIG. 2A.

Singlet excitons may be produced from Host A in the emission layer, and singlet excitons produced from Host A may be transferred to a fluorescence emitter through Förster energy transfer (FRET).

A ratio of singlet excitons produced from Host A may be 25%, and thus, 75% of triplet excitons produced from Host A may be fused to one another to be converted into singlet excitons. Thus, the efficiency of the organic light-emitting device may be further improved. That is, efficiency of an organic light-emitting device may be further improved by using a triplet-triplet fusion mechanism.

According to the First Embodiment, a ratio of emission components emitted from the condensed cyclic compound to the total emission components emitted from the emission layer may be about 80% or greater, for example, about 90% or greater. In some embodiments, a ratio of emission components emitted from the condensed cyclic compound may be about 95% or greater to the total emission components emitted from the emission layer.

The condensed cyclic compound may emit fluorescence, and the host may not emit light.

In the First Embodiment, when the emission layer further includes Host A, in addition to the condensed cyclic compound, the amount of the condensed cyclic compound in the emission layer may be 50 parts by weight or less, e.g., 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of Host A in the emission layer may be 50 parts by weight or greater, e.g., 70 parts by weight or greater, based on 100 parts by weight of the emission layer, but embodiments are not limited thereto.

In the First Embodiment, when the emission layer further includes Host A, in addition to the condensed cyclic compound, Host A and the condensed cyclic compound may satisfy Condition A:

E(H_A)_s1>E_S1  Condition A

wherein, in Condition A,

E(H_A)_S1 indicates a lowest excited singlet energy level of Host A, and

E_S1 indicates a lowest excited singlet energy level of the condensed cyclic compound.

Here, E(H_A)_S1 and E_S1 may be evaluated by using Gaussian according to density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p)).

Second Embodiment—Descriptions of FIG. 2B

In the Second Embodiment, the condensed cyclic compound may be a delayed fluorescence emitter. According to the Second Embodiment, the emission layer may further include a host (hereinafter, referred to as ‘Host B’, and Host B may not be identical to the condensed cyclic compound). Host B may be understood by referring to the description of the host material provided herein, but embodiments are not limited thereto.

General energy transfer of the Second Embodiment may be explained according to FIG. 2B.

25% of singlet excitons produced from Host B in the emission layer may be transferred to a delayed fluorescence emitter through FRET. In addition, 75% of triplet excitons produced from Host B in the emission layer may be transferred to a delayed fluorescence emitter through Dexter energy transfer. Energy transferred to a triplet state of a delayed fluorescence emitter may undergo RISC to a singlet state. Accordingly, singlet excitons and triplet excitons produced from the emission layer may be transferred to the condensed cyclic compound. Thus, the organic light-emitting device may have improved efficiency.

According to the Second Embodiment, a ratio of emission components emitted from the condensed cyclic compound to the total emission components emitted from the emission layer may be about 80% or greater, for example, about 90% or greater. In some embodiments, a ratio of emission components emitted from the condensed cyclic compound may be about 95% or greater to the total emission components emitted from the emission layer.

Here, the condensed cyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the condensed cyclic compound may be a total of prompt emission components of the condensed cyclic compound and delayed fluorescence components by RISC of the condensed cyclic compound. In addition, Host B may not emit light.

In the Second Embodiment, when the emission layer further includes Host B, in addition to the condensed cyclic compound, the amount of the condensed cyclic compound in the emission layer may be 50 parts by weight or less, e.g., 30 parts by weight or less, based on 100 parts by weight of the emission layer, and the amount of Host B in the emission layer may be 50 parts by weight or greater, e.g., 70 parts by weight or greater, based on 100 parts by weight of the emission layer, but embodiments are not limited thereto.

In the Second Embodiment, when the emission layer further includes Host B, in addition to the condensed cyclic compound, Host B and the condensed cyclic compound may satisfy Condition B:

E(H_B)_S1>E_S1  Condition B

wherein, in Condition B,

E(H_B)_S1 indicates a lowest excited singlet energy level of Host B, and

E_S1 indicates a lowest excited singlet energy level of the condensed cyclic compound.

Here, E(H_B)_S1 and E_S1 may be evaluated by using Gaussian according to density functional theory (DFT) method (wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p)).

Third Embodiment—Descriptions of FIG. 2C

In the Third Embodiment, the condensed cyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer. In the Third Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host C’, and Host C may not be identical to the condensed cyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer A’, and Sensitizer A may not be identical to Host C and the condensed cyclic compound). Host C and Sensitizer A may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Third Embodiment, a ratio of emission components of the condensed cyclic compound in the emission layer may be about 80% or greater, for example, 90% or greater (or for example, 95% or greater) to the total emission components emitted from the emission layer. For example, the condensed cyclic compound may emit fluorescence. In addition, Host C and Sensitizer A may not each emit light.

General energy transfer of the Third Embodiment may be explained according to FIG. 2C.

Singlet and triplet excitons may be produced from Host C in the emission layer, and singlet and triplet excitons produced from Host C may be transferred to Sensitizer A and then to the condensed cyclic compound through FRET. 25% of singlet excitons produced from Host C may be transferred to Sensitizer A through FRET, and energy of 75% of triplet excitons produced from Host C may be transferred to singlet and triplet states of Sensitizer A. Energy transferred to a triplet state of Sensitizer A may undergo RISC to a singlet state, and then, singlet energy of Sensitizer A may be transferred to the condensed cyclic compound through FRET.

Accordingly, singlet excitons and triplet excitons produced from the emission layer may be transferred to the dopant. Thus, the organic light-emitting device may have improved efficiency. Further, energy loss of the organic light-emitting device may be significantly small. Thus, the organic light-emitting device may have improved lifespan characteristics.

In the Third Embodiment, when the emission layer further includes Host C and Sensitizer A, in addition to the condensed cyclic compound, Host C and Sensitizer A may satisfy Condition C-1 and/or C-2:

S ₁(H_C)≥S₁(S_A)  Condition C-1

S ₁(S_A)≥S₁(HC)  Condition C-2

wherein, in Conditions C-1 and C-2,

S₁(H_C) indicates a lowest excited singlet energy level of Host C,

S₁(S_A) indicates a lowest excited singlet energy level of Sensitizer A, and

S₁(HC) indicates a lowest excited singlet energy level of the condensed cyclic compound.

S₁(H_C), S₁(S_A), and S₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, according to the Gaussian according to DFT method.

When Host C, Sensitizer A, and the condensed cyclic compound satisfy Condition C-1 and/or C-2, FRET from Sensitizer A to the condensed cyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

Fourth Embodiment—Descriptions of FIG. 2D

In the Fourth Embodiment, the condensed cyclic compound may be used as a fluorescence emitter, and the emission layer may include a sensitizer, e.g., a phosphorescence sensitizer. In the Fourth Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host D’, and Host D may not be identical to the condensed cyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer B’, and Sensitizer B may not be identical to Host D and the condensed cyclic compound). Host D and Sensitizer B may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Fourth Embodiment, a ratio of emission components of the condensed cyclic compound in the emission layer may be about 80% or greater, for example, 90% or greater (or for example, 95% or greater) to the total emission components emitted from the emission layer. For example, the condensed cyclic compound may emit fluorescence. In addition, Host D and Sensitizer B may not each emit light.

General energy transfer of the Fourth Embodiment may be explained according to FIG. 2D.

75% of triplet excitons produced from Host D in the emission layer may be transferred to Sensitizer B through Dexter energy transfer, and energy of 25% of singlet excitons produced from Host D may be transferred to singlet and triplet states of Sensitizer B. Energy transferred to a singlet state of Sensitizer B may undergo ISC to a triplet state, and then, triplet energy of Sensitizer B may be transferred to the condensed cyclic compound through FRET.

Accordingly, singlet excitons and triplet excitons produced from the emission layer may be transferred to the dopant. Thus, the organic light-emitting device may have improved efficiency. Further, energy loss of the organic light-emitting device may be substantially minimized. Thus, the organic light-emitting device may have improved lifespan characteristics.

In the Third Embodiment, when the emission layer further includes Host D and Sensitizer B, in addition to the condensed cyclic compound, Host D and Sensitizer B may satisfy Condition D-1 and/or D-2:

T ₁(H_D)≥T₁(S_B)  Condition D-1

T ₁(S_B)≥S₁(HC)  Condition D-2

wherein, in Conditions D-1 and D-2,

T₁(H_D) indicates a lowest excited triplet energy level of Host D,

T₁(S_B) indicates a lowest excited triplet energy level of Sensitizer B, and

S₁(HC) indicates a lowest excited singlet energy level of the condensed cyclic compound.

T₁(H_D), T₁(S_B), and S₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d,p), for example, according to the Gaussian program according to the DFT method.

When Host D, Sensitizer B, and the condensed cyclic compound satisfy Condition D-1 and/or D-2, FRET from Sensitizer B to the condensed cyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

In the Third Embodiment and the Fourth Embodiment, a content of the sensitizer in the emission layer may be in a range of about 5 percent by weight (wt %) to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the content is within this range, energy transfer in the emission layer may effectively take place. Thus, the organic light-emitting device may have high efficiency and long lifespan.

In the Third Embodiment and the Fourth Embodiment, a content of the condensed cyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

In the Third Embodiment and the Fourth Embodiment, the sensitizer and the condensed cyclic compound may further satisfy Condition 5:

0 μs<T_decay(HC)<5 μs  Condition 5

In Condition 5, T_decay(HC) indicates a decay time of the condensed cyclic compound.

The decay time of the condensed cyclic compound was measured from a time-resolved photoluminescence (TRPL) spectrum at room temperature of a film (hereinafter, referred to as “Film (HC)”) having a thickness of 40 nm formed by vacuum-depositing the host and the condensed cyclic compound included in the emission layer on a quartz substrate at a weight ratio of 90:10 at a vacuum pressure of 10⁻⁷ torr.

Fifth Embodiment—Descriptions of FIG. 2E

In the Fifth Embodiment, the condensed cyclic compound may be used as a delayed fluorescence emitter, and the emission layer may include a sensitizer, e.g., a delayed fluorescence sensitizer. In the Fifth Embodiment, the emission layer may further include a host (hereinafter, the host may be referred to as ‘Host E’, and Host E may not be identical to the condensed cyclic compound and the sensitizer) and a sensitizer (hereinafter, the sensitizer may be referred to as ‘Sensitizer C’, and Sensitizer C may not be identical to Host E and the condensed cyclic compound). Host E and Sensitizer C may respectively be understood by referring to the description of the host material and the sensitizer material provided herein, but embodiments are not limited thereto.

In the Fifth Embodiment, a ratio of emission components of the condensed cyclic compound may be about 80% or greater, for example, 90% or greater (or for example, 95% or greater) to the total emission components emitted from the emission layer. In some embodiments, the condensed cyclic compound may emit fluorescence and/or delayed fluorescence. In addition, Host E and Sensitizer C may not each emit light.

Here, the condensed cyclic compound may emit fluorescence and/or delayed fluorescence, and the emission components of the condensed cyclic compound may be a total of prompt emission components of the condensed cyclic compound and delayed fluorescence components by RISC of the condensed cyclic compound.

General energy transfer of the Fifth Embodiment may be explained according to FIG. 2E.

25% of singlet excitons produced from Host E in the emission layer may be transferred to a singlet state of Sensitizer C through FRET, and energy of 75% of triplet excitons produced from Host E may be transferred to a triplet state of Sensitizer C, and then singlet energy of Sensitizer C may be transferred to the condensed cyclic compound through FRET. Subsequently, the triplet energy of Sensitizer C may be transferred to the condensed cyclic compound through Dexter energy transfer. Energy transferred to a triplet state of Sensitizer C may undergo RISC to a singlet state. Further, in a case of Sensitizer C, energy of triplet excitons produced from Sensitizer C may undergo reverse transfer to Host E and then to the condensed cyclic compound, thus emitting by reverse intersystem transfer.

Accordingly, singlet excitons and triplet excitons produced from the emission layer may be transferred to the dopant. Thus, the organic light-emitting device may have improved efficiency. Further, energy loss of the organic light-emitting device may be minimized. Thus, the organic light-emitting device may have improved lifespan characteristics.

In the Fifth Embodiment, when the emission layer further includes Host E and Sensitizer C, in addition to the condensed cyclic compound, Host E and Sensitizer C may satisfy Condition E-1, E-2, and/or E-3:

S ₁(H_E)≥S₁(S_C)  Condition E-1

S ₁(S_C)≥S₁(HC)  Condition E-2

T ₁(S_C)≥T₁(HC)  Condition E-3

In Conditions E-1, E-2, and E-3, S₁(H_E) indicates a lowest excited singlet energy level of Host E, S₁(S_C) indicates a lowest excited singlet energy level of Sensitizer C, S₁(HC) indicates a lowest excited singlet energy level of the condensed cyclic compound, T₁(S_C) indicates a lowest excited triplet energy level of Sensitizer C, and T₁(HC) indicates a lowest excited triplet energy level of the condensed cyclic compound.

S₁(H_E), S₁(S_C), S₁(HC), T₁(S_C), and T₁(HC) may be evaluated according to the DFT method, wherein structure optimization is performed at a degree of B3LYP, and 6-31G(d, p), for example, according to the DFT method of the Gaussian program.

When Host E, Sensitizer C, and the condensed cyclic compound satisfy Condition E-1, E-2, and/or E-3, Dexter transfer FRET from Sensitizer C to the condensed cyclic compound may be facilitated, and accordingly, the organic light-emitting device may have improved luminescence efficiency.

In the Fifth Embodiment, a content of Sensitizer C in the emission layer may be in a range of about 5 wt % to about 50 wt %, or for example, about 10 wt % to about 30 wt %. When the content is within this range, energy transfer in the emission layer may be effectively occurred. Thus, the organic light-emitting device may have high efficiency and long lifespan.

In the Fifth Embodiment, a content of the condensed cyclic compound in the emission layer may be in a range of about 0.01 wt % to about 15 wt %, or for example, about 0.05 wt % to about 3 wt %, but embodiments are not limited thereto.

Host

The host may not include a metal atom.

In an embodiment, the host may consist of one type of host. When the host consists of one type of host, the one type of host may be a bipolar host, an electron transporting host, and a hole transporting host described herein.

In one or more embodiments, the host may be a mixture of two or more types of hosts. In some embodiments, the host may be a mixture of an electron transporting host and a hole transporting host, a mixture of two different types of electron transporting hosts or a mixture of two different types of hole transporting hosts. The electron transporting host and the hole transporting host may respectively be understood by referring to the descriptions of the electron transporting host and the hole transporting host provided herein.

In an embodiment, the host may include an electron transporting host including at least one electron transporting moiety and a hole transporting host not including an electron transporting moiety.

The electron transporting moiety may be a cyano group, a π electron-depleted nitrogen-containing cyclic group, and a group represented by one of following Formulae:

wherein, in Formulae ET-moiety, *, *′, and *″ may each indicate a binding site to an adjacent atom.

In an embodiment, an electron transporting host in the emission layer 15 may include at least one of a cyano group, a π electron-depleted nitrogen-containing cyclic group, or any combination thereof.

In one or more embodiments, the electron transporting host in the emission layer 15 may include at least one cyano group.

In one or more embodiments, an electron transporting host in the emission layer 15 may include a cyano group, at least one π electron-depleted nitrogen-containing cyclic group, or any combination thereof.

In one or more embodiments, the host may include an electron transporting host and a hole transporting host, the electron transporting host may include at least one π electron-depleted nitrogen-free cyclic group and at least one electron transporting moiety, and the hole transporting host may include at least one π electron-depleted nitrogen-free cyclic group and may not include an electron transporting moiety.

The term “π electron-depleted nitrogen-containing cyclic group” as used herein refers to a cyclic group having at least one *—N═*′ moiety. Examples thereof may include: an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and a condensed ring of at least two π electron-depleted nitrogen-containing cyclic groups.

The π electron-depleted nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, and a triindolobenzene group; and a condensed ring of at least two π electron-depleted nitrogen-free cyclic group, but embodiments are not limited thereto.

In some embodiments, the electron transporting host may be Compounds represented by Formula E-1, and the hole transporting host may be Compounds represented by Formula H-1, but embodiments are not limited thereto:

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21  Formula E-1

wherein, in Formula E-1,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group and a substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may each independently be a single bond, groups represented by one of following Formulae, a substituted or unsubstituted C₅-C₆₀ carbocyclic group, and a substituted or unsubstituted C₁-C₆₀ heterocyclic group, wherein in the following Formulae, *, *′, and *″ may each indicate a binding site to an adjacent atom,

xb1 may be an integer from 1 to 5,

R₃₀₁ may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀₁), —P(═O)(Q₃₀₁)(Q₃₀₂), or —P(═S)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5,

wherein Q₃₀₁ to Q₃₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, and

at least one of Conditions H-1 to H-3 may be satisfied:

Condition H-1

wherein, at least one of Ar₃₀₁, L₃₀₁, and R₃₀₁ in Formula E-1 may each independently include a π electron-depleted nitrogen-containing cyclic group,

Condition H-2

wherein, in Formula E-1, L₃₀₁ may be a group represented by one of the following Formulae, and

Condition H-3

wherein, in Formula E-1, R₃₀₁ may be a cyano group, —S(═O)₂(Q₃₀₁), —S(═O)(Q₃₀), —P(═O)(Q₃₀₁)(Q₃₀₂), and —P(═S)(Q₃₀₁)(Q₃₀₂)

wherein, in Formulae H-1, 11, and 12,

L₄₀₁ may be:

a single bond; or

a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, or a triindolobenzene group, each unsubstituted or substituted with at least one of deuterium, a C₁-C₁₀ alkyl group, a alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a triphenylenyl group, a biphenyl group, a terphenyl group, tetraphenyl group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), or any combination thereof,

xd1 may be an integer from 1 to 10; and when xd1 is 2 or greater, at least two L₄₀₁(s) may be identical to or different from each other,

Ar₄₀₁ may be a group represented by Formulae 11 or 12,

Ar₄₀₂ may be:

a group represented by Formulae 11 or 12, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group; or

a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, each substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, a triphenylenyl group, or any combination thereof,

CY₄₀₁ and CY₄₀₂ may each independently be a benzene group, a naphthalene group, a fluorene group, a carbazole group, a benzocarbazole group, an indolocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, a benzonaphthofuran group, a benzonapthothiophene group, or a benzonaphthosilole group,

A₂₁ may be a single bond, O, S, N(R₅₁), C(R₅₁)(R₅₂), or Si(R₅₁)(R₅₂),

A₂₂ may be a single bond, O, S, N(R₅₃), C(R₅₃)(R₅₄), or Si(R₅₃)(R₅₄),

at least one of A₂₁, A₂₂, or any combination thereof in Formula 12 may not be a single bond,

R₅₁ to R₅₄, R₆₀, and R₇₀ may each independently be:

hydrogen, deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, or a C₁-C₂₀ alkoxy group;

a C₁-C₂₀ alkyl group and a C₁-C₂₀ alkoxy group, each substituted with at least one deuterium, a hydroxyl 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 naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;

a π electron-depleted nitrogen-free cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group);

a π electron-depleted nitrogen-free cyclic group (e.g., a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, and a triphenylenyl group) substituted with at least one deuterium, a hydroxyl group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, or any combination thereof,

—Si(Q₄₀₄)(Q₄₀₅)(Q₄₀₆),

e1 and e2 may each independently be an integer from 0 to 10,

wherein Q₄₀₁ to Q₄₀₆ may each independently be hydrogen, deuterium, a hydroxyl 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 naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a biphenyl group, a terphenyl group, or a triphenylenyl group, and

* indicates a binding site to an adjacent atom.

In some embodiments, in Formula E-1, Ar₃₀₁ and L₃₀₁ may each independently be a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, a dibenzothiophene group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof,

at least one of L₃₀₁ in the number of xb1 may each independently be an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, or an azacarbazole group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof, and

R₃₀₁ may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a tetraphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing tetraphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁ to Q₃₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, but embodiments are not limited thereto.

In some embodiments, Ar₃₀₁ may be: a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a dibenzofuran group, or a dibenzothiophene group, each unsubstituted or substituted with at least one deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

a group represented by Formulae 5-1 to 5-3 and 6-1 to 6-33, and

L₃₀₁ may be a group represented by Formulae 5-1 to 5-3 and 6-1 to 6-33:

wherein, in Formulae 5-1 to 5-3 and 6-1 to 6-33,

Z₁ may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a cyano group-containing phenyl group, a cyano group-containing biphenyl group, a cyano group-containing terphenyl group, a cyano group-containing naphthyl group, a pyridinyl group, a phenylpyridinyl group, a diphenylpyridinyl group, a biphenylpyridinyl group, a di(biphenyl)pyridinyl group, a pyrazinyl group, a phenylpyrazinyl group, a diphenylpyrazinyl group, a biphenylpyrazinyl group, a di(biphenyl)pyrazinyl group, a pyridazinyl group, a phenylpyridazinyl group, a diphenylpyridazinyl group, a biphenylpyridazinyl group, a di(biphenyl)pyridazinyl group, a pyrimidinyl group, a phenylpyrimidinyl group, a diphenylpyrimidinyl group, a biphenylpyrimidinyl group, a di(biphenyl)pyrimidinyl group, a triazinyl group, a phenyltriazinyl group, a diphenyltriazinyl group, a biphenyltriazinyl group, a di(biphenyl)triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), or —P(═O)(Q₃₁)(Q₃₂),

d4 may be 0, 1, 2, 3, or 4,

d3 may be 0, 1, 2, or 3,

d2 may be 0, 1, or 2, and

* and *′ each indicate a binding site to an adjacent atom.

wherein Q₃₁ to Q₃₃ may respectively be understood by referring to the descriptions of Q₃₁ to Q₃₃ provided herein.

In one or more embodiments, L₃₀₁ may be a group represented by Formulae 5-2, 5-3, and 6-8 to 6-33.

In one or more embodiments, R₃₀₁ may be a cyano group or a group represented by Formulae 7-1 to 7-18, and at least one Ar₄₀₂ in the number of xd11 may be a group represented by Formulae 7-1 to 7-18, but embodiments are not limited thereto:

wherein, in Formulae 7-1 to 7-18,

xb41 to xb44 may each be 0, 1, or 2, provided that xb41 in Formula 7-10 may not be 0, xb41+xb42 in Formulae 7-11 to 7-13 may not be 0, xb41+xb42+xb43 in Formulae 7-14 to 7-16 may not be 0, xb41+xb42+xb43+xb44 in Formulae 7-17 and 7-18 may not be 0, and * indicates a binding site to an adjacent atom.

In Formula E-1, at least two Ar₃₀₁(s) may be identical to or different from each other, and at least two L₃₀₁(s) may be identical to or different from each other. In Formula H-1, at least two L₄₀₁(s) may be identical to or different from each other, and at least two Ar₄₀₂(s) may be identical to or different from each other.

In an embodiment, the electron transporting host may include i) at least one a cyano group, a pyrimidine group, a pyrazine group, a triazine group, or any combination thereof, or ii) a triphenylene group, and the hole transporting host may include a carbazole group.

In one or more embodiments, the electron transporting host may include at least one cyano group.

The electron transporting host may be selected from, for example, Groups HE1 to HE7, but embodiments are not limited thereto:

In some embodiments, the electron transporting host may include DPEPO and TSPO1:

In some embodiments, the hole transporting host may be Group HH1, but embodiments are not limited thereto:

In some embodiments, the bipolar host may be Group HEH1, but embodiments are not limited thereto:

wherein “Ph” in Compounds 1 to 432 represents a phenyl group.

In some embodiments, the hole transporting host may include o-CBP or mCP:

In some embodiments, the host may be a fluorescent host, and the fluorescent host may be represented by, for example, one of Formulae FH-1 to FH-4.

In some embodiments, the fluorescent host may be represented by Formula FH-1.

wherein, in Formula FH-1,

Ar₁ to Ar₃ may each independently be a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

at least one of Ar₁ to Ar₃ may be a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or any combination thereof,

L₁₀ may be a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

a10 may be an integer from 0 to 3, and when a10 is 2 or greater, at least two L₁₀(s) may be identical to or different from each other,

R₁₀ and R₂₀ may be each independently hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b10 and b20 may each independently be an integer from 1 to 8,

when b10 is 2 or greater, at least two R₁₀(s) may be identical to or different from each other, and when b20 is 2 or greater, at least two R₂₀(s) may be identical to or different from each other,

c10 may be an integer from 1 to 9, and

when c10 is 2 or greater, at least two -[(L₁₀)_a10-(R₁₀)_b10](s) may be identical to or different from each other.

In some embodiments, the fluorescent host represented by Formula FH-1 may be Group FH1, but embodiments are not limited thereto:

In some embodiments, the fluorescent host may be represented by Formula FH-2:

wherein, in Formula FH-2,

X₁ may be O or S,

A₁ may be a C₅-C₆₀ carbocyclic group and a C₁-C₆₀ heterocyclic group,

L₁₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group or a substituted or unsubstituted C₁-C₆₀ heterocyclic group,

a11 may be an integer from 0 to 3,

Ar₁₁ and Ar₁₂ may each independently be a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each unsubstituted or substituted with at least one R_a,

b11 may be an integer from 1 to 5,

R₁₁, R₁₂, and R_a may each independently be hydrogen, 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 substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl 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), or —B(Q₆)(Q₇),

c11 may be an integer from 1 to 20,

c12 may be an integer from 1 to 4,

when c11 is 2 or greater, two adjacent R₁₁(s) may optionally be bound to each other to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group and a substituted or unsubstituted C₁-C₃₀heterocarbocyclic group, when c12 is 2 or greater, two adjacent R₁₂(s) may optionally be bound to each other to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group and a substituted or unsubstituted C₁-C₃₀heterocarbocyclic group,

A₁ and Ar₁₂ may optionally be bound to each other to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group via a first linking group a single bond, *—Ar₃₁—*′, *—O—*′, *—S—*′, *—[C(R₃₁)(R₃₂)]_k11—′, *—C(R₃₁)═′, *═C(R₃₁)—′, *—C(R₃₁)═C(R₃₂)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—N(R₃₁)—*′, *—P(R₃₁)—*′, *—[Si(R₃₁)(R₃₂)]_k11—*′, or *—P(R₃₁)(R₃₂)—*′,

Ar₃₁ may be a C₅-C₃₀ carbocyclic group,

R₃₁ and R₃₂ may each be understood by referring to the description of R₁₁ provided herein, and

k11 may be 1, 2, 3, and 4.

In some embodiments, the fluorescent host represented by Formula FH-2 may be Group FH2, but embodiments are not limited thereto:

In some embodiments, the fluorescent host may be represented by Formula FH-3:

wherein, in Formula FH-3,

Ar₁ may be a group represented by Formula 2:

Ar₁ may include at least one cyano group,

A₁ and A₂ may each independently be a C₅-C₃₀ carbocyclic group or a C₁-C₃₀ heterocyclic group,

L₁ may be a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

a1 may be 0, 1, 2, or 3,

when a1 is 2 or greater, at least two L₁(s) may be identical to different from each other,

m1 may be 0, 1, 2, or 3, and

Ar₁₁ may be a group represented by Formula 4, Ar₁₂ may be a group represented by Formula 5, and Ar₁₃ may be a group represented by Formula 6:

wherein, in Formulae 4 to 6,

R₁, R₁₀, R₂₀, R₃₀, R₄₀, R₅₀, and R₆₀ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀ heteroarylthio 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), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b1 may be an integer from 1 to 5,

when b1 is 2 or greater, at least two R₁(s) may be identical to or different from each other,

b10 may be an integer from 1 to 8,

when b10 is 2 or greater, at least two R₁₀(s) may be identical to or different from each other,

b20 and b30 may each independently be an integer from 1 to 4,

when b20 is 2 or greater, at least two R₂₀(s) may be identical to or different from each other, and when b30 is 2 or greater, at least two R₃₀(s) may be identical to or different from each other,

b40, b50, and b60 may each independently be an integer from 1 to 4,

when b40 is 2 or greater, at least two R₄₀(s) may be identical to or different from each other, when b50 is 2 or greater, at least two R₅₀(s) may be identical to or different from each other, and when b60 is 2 or greater, at least two R₆₀(s) may be identical to or different from each other, and

* and *′ each indicate a binding site to an adjacent atom.

In some embodiments, the fluorescent host represented by Formula FH-3 may be Group FH3, but embodiments are not limited thereto:

In some embodiments, the fluorescent host may be represented by Formula FH-4:

wherein, in Formula FH-4,

X₁ may be O or Se, and

Ar₁ may be a group represented by Formula 1A, and Ar₂ may be a group represented by Formula 1B:

wherein, in Formulae 4 to 6,

L₁ and L₂ may each independently be a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

a1 and a2 may each independently be an integer from 0 to 3,

when a1 is 2 or greater, at least two L₁(s) may be identical to or different from each other, and when a2 is 2 or greater, at least two L₂(s) may be identical to or different from each other,

R₁, R₂, R₁₀, R₂₀, R₃₀, and R₄₀ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), or —P(═O)(Q₈)(Q₉),

b1 and b2 may each independently be an integer from 1 to 5,

when b1 is 2 or greater, at least two R₁(s) may be identical to or different from each other, and when b2 is 2 or greater, at least two R₂(s) may be identical to or different from each other,

b10 and b20 may each independently be an integer from 1 to 8,

b30 and b40 may each independently be an integer from 1 to 3,

c1 and c2 may each independently be an integer from 1 to 8, and

a sum of b10 and c1 may be 9, and a sum of b20 and c2 may be 9.

In some embodiments, the fluorescent host represented by Formula FH-4 may be Group FH4, but embodiments are not limited thereto:

When the host is a mixture of an electron transporting host and a hole transporting host, a weight ratio of the electron transporting host to the hole transporting host may be in a range of about 1:9 to about 9:1, for example, about 2:8 to about 8:2, for example, about 4:6 to about 6:4, or for example, about 5:5. When a weight ratio of the electron transporting host to the hole transporting host is within any of these ranges, holes and electrons transport balance into the emission layer 15 may be achieved.

Dopant

The dopant may include the condensed cyclic compound.

Sensitizer

In some embodiments, the sensitizer may be a phosphorescent sensitizer including at least one metal a first-row transition metal, a second-row transition metal, a third-row transition metal, or any combination thereof.

In some embodiments, the sensitizer may include a metal (M₁₁) of at least one metal a first-row transition metal, a second-row transition metal, a third-row transition metal, or any combination thereof, and an organic ligand (L₁₁), and L₁₁ and M₁₁ may form 1, 2, 3, or 4 cyclometallated ring.

In some embodiments, the sensitizer may include an organometallic compound represented by Formula 101:

M₁₁(L₁₁)_n11(L₁₂)_n12  Formula 101

wherein, in Formula 101,

M₁₁ may be a first-row transition metal, a second-row transition metal, or a third-row transition metal,

L₁₁ may be a ligand represented by one of Formulae 1-1 to 1-4,

L₁₂ may be a monodentate ligand or a bidentate ligand,

n11 may be 1, and

n12 may be 0, 1, and 2:

wherein, in Formulae 1-1 to 1-4,

A₁ to A₄ may each independently be a substituted or unsubstituted C₅-C₃₀ carbocyclic group, a substituted or unsubstituted C₁-C₃₀ heterocyclic group, or a non-cyclic group,

Y₁₁ to Y₁₄ may each independently be a chemical bond, O, S, N(R₉₁), B(R₉₁), P(R₉₁), or C(R₉₁)(R₉₂),

T₁ to T₄ may each independently be a single bond, a double bond, *—N(R₉₃)—*′, *—B(R₉₃)—*′, *—P(R₉₃)—*′, *—C(R₉₃)(R₉₄)—*′, *—Si(R₉₃)(R₉₄)—*′, *—Ge(R₉₃)(R₉₄)—*′, *—S—*′, *—Se—*′, *—O—*′, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₉₃)=*′, *═C(R₉₃)—*′, *—C(R₉₃)═C(R₉₄)—*′, *—C(═S)—*′, or *—C≡C—*′,

a substituent of the substituted C₅-C₃₀ carbocyclic group, a substituent of the substituted C₁-C₃₀ heterocyclic group, and R₉₁ to R₉₄ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro 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-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted monovalent aromatic condensed polycyclic group, a substituted or unsubstituted monovalent aromatic condensed heteropolycyclic 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), —Ge(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂), and the substituent of the substituted C₅-C₃₀ carbocyclic group and the substituent of the substituted C₁-C₃₀ heterocyclic group may not each be hydrogen, and

*₁, *₂, *₃, and *₄ may each be a binding site to M₁₁,

wherein Q₁ to Q₃ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkyl group substituted with at least one of deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, and a C₆-C₆₀ aryl group, and a C₆-C₆₀ aryl group substituted with at least one of deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof.

In some embodiments, the sensitizer may be a compound of Groups I to VIII, but embodiments are not limited thereto:

A compound represented by Formula 1:

(L₁₀₁)_n101-M₁₀₁-(L₁₀₂)_m101  Formula A

wherein, in Formula A, L₁₀₁, n101, M₁₀₁, L₁₀₂, and m101 may respectively be understood by referring to the descriptions of L₁₀₁, n101, M₁₀₁, L₁₀₂, and m101 in Tables 5 to 7:

TABLE 5
Compound name	L101	n101	M101	L102	m101
BD001	LM1	3	Ir	—	0
BD002	LM2	3	Ir	—	0
BD003	LM3	3	Ir	—	0
BD004	LM4	3	Ir	—	0
BD005	LM5	3	Ir	—	0
BD006	LM6	3	Ir	—	0
BD007	LM7	3	Ir	—	0
BD008	LM8	3	Ir	—	0
BD009	LM9	3	Ir	—	0
BD010	LM10	3	Ir	—	0
BD011	LM11	3	Ir	—	0
BD012	LM12	3	Ir	—	0
BD013	LM13	3	Ir	—	0
BD014	LM14	3	Ir	—	0
BD015	LM15	3	Ir	—	0
BD016	LM16	3	Ir	—	0
BD017	LM17	3	Ir	—	0
BD018	LM18	3	Ir	—	0
BD019	LM19	3	Ir	—	0
BD020	LM20	3	Ir	—	0
BD021	LM21	3	Ir	—	0
BD022	LM22	3	Ir	—	0
BD023	LM23	3	Ir	—	0
BD024	LM24	3	Ir	—	0
BD025	LM25	3	Ir	—	0
BD026	LM26	3	Ir	—	0
BD027	LM27	3	Ir	—	0
BD028	LM28	3	Ir	—	0
BD029	LM29	3	Ir	—	0
BD030	LM30	3	Ir	—	0
BD031	LM31	3	Ir	—	0
BD032	LM32	3	Ir	—	0
BD033	LM33	3	Ir	—	0
BD034	LM34	3	Ir	—	0
BD035	LM35	3	Ir	—	0
BD036	LM36	3	Ir	—	0
BD037	LM37	3	Ir	—	0
BD038	LM38	3	Ir	—	0
BD039	LM39	3	Ir	—	0
BD040	LM40	3	Ir	—	0
BD041	LM41	3	Ir	—	0
BD042	LM42	3	Ir	—	0
BD043	LM43	3	Ir	—	0
BD044	LM44	3	Ir	—	0
BD045	LM45	3	Ir	—	0
BD046	LM46	3	Ir	—	0
BD047	LM47	3	Ir	—	0
BD048	LM48	3	Ir	—	0
BD049	LM49	3	Ir	—	0
BD050	LM50	3	Ir	—	0
BD051	LM51	3	Ir	—	0
BD052	LM52	3	Ir	—	0
BD053	LM53	3	Ir	—	0
BD054	LM54	3	Ir	—	0
BD055	LM55	3	Ir	—	0
BD056	LM56	3	Ir	—	0
BD057	LM57	3	Ir	—	0
BD058	LM58	3	Ir	—	0
BD059	LM59	3	Ir	—	0
BD060	LM60	3	Ir	—	0
BD061	LM61	3	Ir	—	0
BD062	LM62	3	Ir	—	0
BD063	LM63	3	Ir	—	0
BD064	LM64	3	Ir	—	0
BD065	LM65	3	Ir	—	0
BD066	LM66	3	Ir	—	0
BD067	LM67	3	Ir	—	0
BD068	LM68	3	Ir	—	0
BD069	LM69	3	Ir	—	0
BD070	LM70	3	Ir	—	0
BD071	LM71	3	Ir	—	0
BD072	LM72	3	Ir	—	0
BD073	LM73	3	Ir	—	0
BD074	LM74	3	Ir	—	0
BD075	LM75	3	Ir	—	0
BD076	LM76	3	Ir	—	0
BD077	LM77	3	Ir	—	0
BD078	LM78	3	Ir	—	0
BD079	LM79	3	Ir	—	0
BD080	LM80	3	Ir	—	0
BD081	LM81	3	Ir	—	0
BD082	LM82	3	Ir	—	0
BD083	LM83	3	Ir	—	0
BD084	LM84	3	Ir	—	0
BD085	LM85	3	Ir	—	0
BD086	LM86	3	Ir	—	0
BD087	LM87	3	Ir	—	0
BD088	LM88	3	Ir	—	0
BD089	LM89	3	Ir	—	0
BD090	LM90	3	Ir	—	0
BD091	LM91	3	Ir	—	0
BD092	LM92	3	Ir	—	0
BD093	LM93	3	Ir	—	0
BD094	LM94	3	Ir	—	0
BD095	LM95	3	Ir	—	0
BD096	LM96	3	Ir	—	0
BD097	LM97	3	Ir	—	0
BD098	LM98	3	Ir	—	0
BD099	LM99	3	Ir	—	0
BD100	LM100	3	Ir	—	0

TABLE 6
Compound name	L101	n101	M101	L102	m101
BD101	LM101	3	Ir	—	0
BD102	LM102	3	Ir	—	0
BD103	LM103	3	Ir	—	0
BD104	LM104	3	Ir	—	0
BD105	LM105	3	Ir	—	0
BD106	LM106	3	Ir	—	0
BD107	LM107	3	Ir	—	0
BD108	LM108	3	Ir	—	0
BD109	LM109	3	Ir	—	0
BD110	LM110	3	Ir	—	0
BD111	LM111	3	Ir	—	0
BD112	LM112	3	Ir	—	0
BD113	LM113	3	Ir	—	0
BD114	LM114	3	Ir	—	0
BD115	LM115	3	Ir	—	0
BD116	LM116	3	Ir	—	0
BD117	LM117	3	Ir	—	0
BD118	LM118	3	Ir	—	0
BD119	LM119	3	Ir	—	0
BD120	LM120	3	Ir	—	0
BD121	LM121	3	Ir	—	0
BD122	LM122	3	Ir	—	0
BD123	LM123	3	Ir	—	0
BD124	LM124	3	Ir	—	0
BD125	LM125	3	Ir	—	0
BD126	LM126	3	Ir	—	0
BD127	LM127	3	Ir	—	0
BD128	LM128	3	Ir	—	0
BD129	LM129	3	Ir	—	0
BD130	LM130	3	Ir	—	0
BD131	LM131	3	Ir	—	0
BD132	LM132	3	Ir	—	0
BD133	LM133	3	Ir	—	0
BD134	LM134	3	Ir	—	0
BD135	LM135	3	Ir	—	0
BD136	LM136	3	Ir	—	0
BD137	LM137	3	Ir	—	0
BD138	LM138	3	Ir	—	0
BD139	LM139	3	Ir	—	0
BD140	LM140	3	Ir	—	0
BD141	LM141	3	Ir	—	0
BD142	LM142	3	Ir	—	0
BD143	LM143	3	Ir	—	0
BD144	LM144	3	Ir	—	0
BD145	LM145	3	Ir	—	0
BD146	LM146	3	Ir	—	0
BD147	LM147	3	Ir	—	0
BD148	LM148	3	Ir	—	0
BD149	LM149	3	Ir	—	0
BD150	LM150	3	Ir	—	0
BD151	LM151	3	Ir	—	0
BD152	LM152	3	Ir	—	0
BD153	LM153	3	Ir	—	0
BD154	LM154	3	Ir	—	0
BD155	LM155	3	Ir	—	0
BD156	LM156	3	Ir	—	0
BD157	LM157	3	Ir	—	0
BD158	LM158	3	Ir	—	0
BD159	LM159	3	Ir	—	0
BD160	LM160	3	Ir	—	0
BD161	LM161	3	Ir	—	0
BD162	LM162	3	Ir	—	0
BD163	LM163	3	Ir	—	0
BD164	LM164	3	Ir	—	0
BD165	LM165	3	Ir	—	0
BD166	LM166	3	Ir	—	0
BD167	LM167	3	Ir	—	0
BD168	LM168	3	Ir	—	0
BD169	LM169	3	Ir	—	0
BD170	LM170	3	Ir	—	0
BD171	LM171	3	Ir	—	0
BD172	LM172	3	Ir	—	0
BD173	LM173	3	Ir	—	0
BD174	LM174	3	Ir	—	0
BD175	LM175	3	Ir	—	0
BD176	LM176	3	Ir	—	0
BD177	LM177	3	Ir	—	0
BD178	LM178	3	Ir	—	0
BD179	LM179	3	Ir	—	0
BD180	LM180	3	Ir	—	0
BD181	LM181	3	Ir	—	0
BD182	LM182	3	Ir	—	0
BD183	LM183	3	Ir	—	0
BD184	LM184	3	Ir	—	0
BD185	LM185	3	Ir	—	0
BD186	LM186	3	Ir	—	0
BD187	LM187	3	Ir	—	0
BD188	LM188	3	Ir	—	0
BD189	LM189	3	Ir	—	0
BD190	LM190	3	Ir	—	0
BD191	LM191	3	Ir	—	0
BD192	LM192	3	Ir	—	0
BD193	LM193	3	Ir	—	0
BD194	LM194	3	Ir	—	0
BD195	LM195	3	Ir	—	0
BD196	LM196	3	Ir	—	0
BD197	LM197	3	Ir	—	0
BD198	LM198	3	Ir	—	0
BD199	LM199	3	Ir	—	0
BD200	LM200	3	Ir	—	0

TABLE 7
Compound name	L101	n101	M101	L102	m101
BD201	LM201	3	Ir	—	0
BD202	LM202	3	Ir	—	0
BD203	LM203	3	Ir	—	0
BD204	LM204	3	Ir	—	0
BD205	LM205	3	Ir	—	0
BD206	LM206	3	Ir	—	0
BD207	LM207	3	Ir	—	0
BD208	LM208	3	Ir	—	0
BD209	LM209	3	Ir	—	0
BD210	LM210	3	Ir	—	0
BD211	LM211	3	Ir	—	0
BD212	LM212	3	Ir	—	0
BD213	LM213	3	Ir	—	0
BD214	LM214	3	Ir	—	0
BD215	LM215	3	Ir	—	0
BD216	LM216	3	Ir	—	0
BD217	LM217	3	Ir	—	0
BD218	LM218	3	Ir	—	0
BD219	LM219	3	Ir	—	0
BD220	LM220	3	Ir	—	0
BD221	LM221	3	Ir	—	0
BD222	LM222	3	Ir	—	0
BD223	LM223	3	Ir	—	0
BD224	LM224	3	Ir	—	0
BD225	LM225	3	Ir	—	0
BD226	LM226	3	Ir	—	0
BD227	LM227	3	Ir	—	0
BD228	LM228	3	Ir	—	0
BD229	LM229	3	Ir	—	0
BD230	LM230	3	Ir	—	0
BD231	LM231	3	Ir	—	0
BD232	LM232	3	Ir	—	0
BD233	LM233	3	Ir	—	0
BD234	LM234	3	Ir	—	0
BD235	LM235	3	Ir	—	0
BD236	LM236	3	Ir	—	0
BD237	LM237	3	Ir	—	0
BD238	LM238	3	Ir	—	0
BD239	LM239	3	Ir	—	0
BD240	LM240	3	Ir	—	0
BD241	LM241	3	Ir	—	0
BD242	LM242	3	Ir	—	0
BD243	LM243	3	Ir	—	0
BD244	LFM1	3	Ir	—	0
BD245	LFM2	3	Ir	—	0
BD246	LFM3	3	Ir	—	0
BD247	LFM4	3	Ir	—	0
BD248	LFM5	3	Ir	—	0
BD249	LFM6	3	Ir	—	0
BD250	LFM7	3	Ir	—	0
BD251	LFP1	3	Ir	—	0
BD252	LFP2	3	Ir	—	0
BD253	LFP3	3	Ir	—	0
BD254	LFP4	3	Ir	—	0
BD255	LFP5	3	Ir	—	0
BD256	LFP6	3	Ir	—	0
BD257	LFP7	3	Ir	—	0
BD258	LM47	2	Ir	AN1	1
BD259	LM47	2	Ir	AN2	1
BD260	LM47	2	Ir	AN3	1
BD261	LM47	2	Ir	AN4	1
BD262	LM47	2	Ir	AN5	1
BD263	LM11	2	Pt	—	0
BD264	LM13	2	Pt	—	0
BD265	LM15	2	Pt	—	0
BD266	LM45	2	Pt	—	0
BD267	LM47	2	Pt	—	0
BD268	LM49	2	Pt	—	0
BD269	LM98	2	Pt	—	0
BD270	LM100	2	Pt	—	0
BD271	LM102	2	Pt	—	0
BD272	LM132	2	Pt	—	0
BD273	LM134	2	Pt	—	0
BD274	LM136	2	Pt	—	0
BD275	LM151	2	Pt	—	0
BD276	LM153	2	Pt	—	0
BD277	LM158	2	Pt	—	0
BD278	LM180	2	Pt	—	0
BD279	LM182	2	Pt	—	0
BD280	LM187	2	Pt	—	0
BD281	LM201	2	Pt	—	0
BD282	LM206	2	Pt	—	0
BD283	LM211	2	Pt	—	0
BD284	LM233	2	Pt	—	0
BD285	LM235	2	Pt	—	0
BD286	LM240	2	Pt	—	0
BD287	LFM5	2	Pt	—	0
BD288	LFM6	2	Pt	—	0
BD289	LFM7	2	Pt	—	0
BD290	LFP5	2	Pt	—	0
BD291	LFP6	2	Pt	—	0
BD292	LFP7	2	Pt	—	0
BD293	LM47	1	Pt	AN1	1
BD294	LM47	1	Pt	AN2	1
BD295	LM47	1	Pt	AN3	1
BD296	LM47	1	Pt	AN4	1
BD297	LM47	1	Pt	AN5	1

In Tables 5 to 7, LM1 to LM243 may be understood by referring to Formulae 1-1 to 1-3 and Tables 8 to 10:

TABLE 8
Formula 1-1
Ligand name	R11	R12	R13	R14	R15	R16	R17	R18	R19	R20
LM1	X1	H	X3	H	X1	H	H	H	H	D
LM2	X1	H	X3	H	X1	H	H	H	D	H
LM3	X1	H	X3	H	X1	H	H	H	D	D
LM4	Y1	H	X3	H	Y1	H	H	H	D	D
LM5	Y2	H	X3	H	Y2	H	H	H	D	D
LM6	Y3	H	X3	H	Y3	H	H	H	D	D
LM7	Y3	D	X3	D	Y3	H	H	H	D	D
LM8	Y3	D	X3	D	Y3	D	H	H	D	D
LM9	Y3	D	X3	D	Y3	D	D	H	D	D
LM10	Y3	D	X3	D	Y3	D	D	D	D	D
LM11	Y3	D	Y11	D	Y3	D	D	D	D	D
LM12	Y3	D	Y11	D	Y3	H	X1	H	D	D
LM13	Y3	D	Y11	D	Y3	D	Y3	D	D	D
LM14	Y3	D	Y11	D	Y3	H	X4	H	D	D
LM15	Y3	D	Y11	D	Y3	D	Y12	D	D	D
LM16	X2	H	X3	H	X2	H	H	H	H	D
LM17	X2	H	X3	H	X2	H	H	H	D	H
LM18	X2	H	X3	H	X2	H	H	H	D	D
LM19	Y4	H	X3	H	Y4	H	H	H	D	D
LM20	Y5	H	X3	H	Y5	H	H	H	D	D
LM21	Y6	H	X3	H	Y6	H	H	H	D	D
LM22	Y7	H	X3	H	Y7	H	H	H	D	D
LM23	Y8	H	X3	H	Y8	H	H	H	D	D
LM24	Y9	H	X3	H	Y9	H	H	H	D	D
LM25	Y10	H	X3	H	Y10	H	H	H	D	D
LM26	Y10	D	X3	D	Y10	H	H	H	D	D
LM27	Y10	D	X3	D	Y10	D	H	H	D	D
LM28	Y10	D	X3	D	Y10	D	D	H	D	D
LM29	Y10	D	X3	D	Y10	D	D	D	D	D
LM30	Y10	D	Y11	D	Y10	D	D	D	D	D
LM31	Y10	D	Y11	D	Y10	H	X1	H	D	D
LM32	Y10	D	Y11	D	Y10	D	Y3	D	D	D
LM33	Y10	D	Y11	D	Y10	H	X4	H	D	D
LM34	Y10	D	Y11	D	Y10	D	Y12	D	D	D
LM35	X1	H	X4	H	X1	H	H	H	H	D
LM36	X1	H	X4	H	X1	H	H	H	D	H
LM37	X1	H	X4	H	X1	H	H	H	D	D
LM38	Y1	H	X4	H	Y1	H	H	H	D	D
LM39	Y2	H	X4	H	Y2	H	H	H	D	D
LM40	Y3	H	X4	H	Y3	H	H	H	D	D
LM41	Y3	D	X4	D	Y3	H	H	H	D	D
LM42	Y3	D	X4	D	Y3	D	H	H	D	D
LM43	Y3	D	X4	D	Y3	D	D	H	D	D
LM44	Y3	D	X4	D	Y3	D	D	D	D	D
LM45	Y3	D	Y12	D	Y3	D	D	D	D	D
LM46	Y3	D	Y12	D	Y3	H	X1	H	D	D
LM47	Y3	D	Y12	D	Y3	D	Y3	D	D	D
LM48	Y3	D	Y12	D	Y3	H	X4	H	D	D
LM49	Y3	D	Y12	D	Y3	D	Y12	D	D	D
LM50	X2	H	X4	H	X2	H	H	H	H	D
LM51	X2	H	X4	H	X2	H	H	H	D	H
LM52	X2	H	X4	H	X2	H	H	H	D	D
LM53	Y4	H	X4	H	Y4	H	H	H	D	D
LM54	Y5	H	X4	H	Y5	H	H	H	D	D
LM55	Y6	H	X4	H	Y6	H	H	H	D	D
LM56	Y7	H	X4	H	Y7	H	H	H	D	D
LM57	Y8	H	X4	H	Y8	H	H	H	D	D
LM58	Y9	H	X4	H	Y9	H	H	H	D	D
LM59	Y10	H	X4	H	Y10	H	H	H	D	D
LM60	Y10	D	X4	D	Y10	H	H	H	D	D
LM61	Y10	D	X4	D	Y10	D	H	H	D	D
LM62	Y10	D	X4	D	Y10	D	D	H	D	D
LM63	Y10	D	X4	D	Y10	D	D	D	D	D
LM64	Y10	D	Y12	D	Y10	D	D	D	D	D
LM65	Y10	D	Y12	D	Y10	H	X1	H	D	D
LM66	Y10	D	Y12	D	Y10	D	Y3	D	D	D
LM67	Y10	D	Y12	D	Y10	H	X4	H	D	D
LM68	Y10	D	Y12	D	Y10	D	Y12	D	D	D
LM69	X1	H	X5	H	X1	H	H	H	H	D
LM70	X1	H	X5	H	X1	H	H	H	D	H
LM71	X1	H	X5	H	X1	H	H	H	D	D
LM72	Y1	H	X5	H	Y1	H	H	H	D	D
LM73	Y2	H	X5	H	Y2	H	H	H	D	D
LM74	Y3	H	X5	H	Y3	H	H	H	D	D
LM75	Y3	D	X5	D	Y3	H	H	H	D	D
LM76	Y3	D	X5	D	Y3	D	H	H	D	D
LM77	Y3	D	X5	D	Y3	D	D	H	D	D
LM78	Y3	D	X5	D	Y3	D	D	D	D	D
LM79	Y3	D	Y13	D	Y3	D	D	D	D	D
LM80	Y3	D	Y13	D	Y3	H	X1	H	D	D
LM81	Y3	D	Y13	D	Y3	D	Y3	D	D	D
LM82	Y3	D	Y13	D	Y3	H	X4	H	D	D
LM83	Y3	D	Y13	D	Y3	D	Y12	D	D	D
LM84	X2	H	X5	H	X2	H	H	H	H	D
LM85	X2	H	X5	H	X2	H	H	H	D	H
LM86	X2	H	X5	H	X2	H	H	H	D	D
LM87	Y4	H	X5	H	Y4	H	H	H	D	D
LM88	Y5	H	X5	H	Y5	H	H	H	D	D
LM89	Y6	H	X5	H	Y6	H	H	H	D	D
LM90	Y7	H	X5	H	Y7	H	H	H	D	D
LM91	Y8	H	X5	H	Y8	H	H	H	D	D
LM92	Y9	H	X5	H	Y9	H	H	H	D	D
LM93	Y10	H	X5	H	Y10	H	H	H	D	D
LM94	Y10	D	X5	D	Y10	H	H	H	D	D
LM95	Y10	D	X5	D	Y10	D	H	H	D	D
LM96	Y10	D	X5	D	Y10	D	D	H	D	D
LM97	Y10	D	X5	D	Y10	D	D	D	D	D
LM98	Y10	D	Y13	D	Y10	D	D	D	D	D
LM99	Y10	D	Y13	D	Y10	H	X1	H	D	D
LM100	Y10	D	Y13	D	Y10	D	Y3	D	D	D
LM101	Y10	D	Y13	D	Y10	H	X4	H	D	D
LM102	Y10	D	Y13	D	Y10	D	Y12	D	D	D
LM103	X1	H	X6	H	X1	H	H	H	H	D
LM104	X1	H	X6	H	X1	H	H	H	D	H
LM105	X1	H	X6	H	X1	H	H	H	D	D
LM106	Y1	H	X6	H	Y1	H	H	H	D	D
LM107	Y2	H	X6	H	Y2	H	H	H	D	D
LM108	Y3	H	X6	H	Y3	H	H	H	D	D
LM109	Y3	D	X6	D	Y3	H	H	H	D	D
LM110	Y3	D	X6	D	Y3	D	H	H	D	D
LM111	Y3	D	X6	D	Y3	D	D	H	D	D
LM112	Y3	D	X6	D	Y3	D	D	D	D	D
LM113	Y3	D	Y14	D	Y3	D	D	D	D	D
LM114	Y3	D	Y14	D	Y3	H	X1	H	D	D
LM115	Y3	D	Y14	D	Y3	D	Y3	D	D	D
LM116	Y3	D	Y14	D	Y3	H	X4	H	D	D
LM117	Y3	D	Y14	D	Y3	D	Y12	D	D	D
LM118	X2	H	X6	H	X2	H	H	H	H	D
LM119	X2	H	X6	H	X2	H	H	H	D	H
LM120	X2	H	X6	H	X2	H	H	H	D	D
LM121	Y4	H	X6	H	Y4	H	H	H	D	D
LM122	Y5	H	X6	H	Y5	H	H	H	D	D
LM123	Y6	H	X6	H	Y6	H	H	H	D	D
LM124	Y7	H	X6	H	Y7	H	H	H	D	D
LM125	Y8	H	X6	H	Y8	H	H	H	D	D
LM126	Y9	H	X6	H	Y9	H	H	H	D	D
LM127	Y10	H	X6	H	Y10	H	H	H	D	D
LM128	Y10	D	X6	D	Y10	H	H	H	D	D
LM129	Y10	D	X6	D	Y10	D	H	H	D	D
LM130	Y10	D	X6	D	Y10	D	D	H	D	D
LM131	Y10	D	X6	D	Y10	D	D	D	D	D
LM132	Y10	D	Y14	D	Y10	D	D	D	D	D
LM133	Y10	D	Y14	D	Y10	H	X1	H	D	D
LM134	Y10	D	Y14	D	Y10	D	Y3	D	D	D
LM135	Y10	D	Y14	D	Y10	H	X4	H	D	D
LM136	Y10	D	Y14	D	Y10	D	Y12	D	D	D
LM137	X1	H	X7	H	X1	H	H	H	H	D
LM138	X1	H	X7	H	X1	H	H	H	D	H
LM139	X1	H	X7	H	X1	H	H	H	D	D
LM140	Y1	H	X7	H	Y1	H	H	H	D	D
LM141	Y2	H	X7	H	Y2	H	H	H	D	D
LM142	Y3	H	X7	H	Y3	H	H	H	D	D
LM143	Y3	D	X7	D	Y3	H	H	H	D	D
LM144	Y3	D	X7	D	Y3	D	H	H	D	D
LM145	Y3	D	X7	D	Y3	D	D	H	D	D
LM146	Y3	D	X7	D	Y3	D	D	D	D	D
LM147	Y3	D	X8	D	Y3	D	D	D	D	D
LM148	Y3	D	Y16	D	Y3	D	D	D	D	D
LM149	Y3	D	Y17	D	Y3	D	D	D	D	D
LM150	Y3	D	Y18	D	Y3	D	D	D	D	D
LM151	Y3	D	Y15	D	Y3	D	D	D	D	D
LM152	Y3	D	Y15	D	Y3	H	X1	H	D	D
LM153	Y3	D	Y15	D	Y3	D	Y3	D	D	D
LM154	Y3	D	Y16	D	Y3	D	Y3	D	D	D
LM155	Y3	D	Y17	D	Y3	D	Y3	D	D	D
LM156	Y3	D	Y18	D	Y3	D	Y3	D	D	D
LM157	Y3	D	Y15	D	Y3	H	X4	H	D	D
LM158	Y3	D	Y15	D	Y3	D	Y12	D	D	D
LM159	Y3	D	Y16	D	Y3	D	Y12	D	D	D
LM160	Y3	D	Y17	D	Y3	D	Y12	D	D	D
LM161	Y3	D	Y18	D	Y3	D	Y12	D	D	D
LM162	X2	H	X7	H	X2	H	H	H	H	D
LM163	X2	H	X7	H	X2	H	H	H	D	H
LM164	X2	H	X7	H	X2	H	H	H	D	D
LM165	Y4	H	X7	H	Y4	H	H	H	D	D
LM166	Y5	H	X7	H	Y5	H	H	H	D	D
LM167	Y6	H	X7	H	Y6	H	H	H	D	D
LM168	Y7	H	X7	H	Y7	H	H	H	D	D
LM169	Y8	H	X7	H	Y8	H	H	H	D	D
LM170	Y9	H	X7	H	Y9	H	H	H	D	D
LM171	Y10	H	X7	H	Y10	H	H	H	D	D
LM172	Y10	D	X7	D	Y10	H	H	H	D	D
LM173	Y10	D	X7	D	Y10	D	H	H	D	D
LM174	Y10	D	X7	D	Y10	D	D	H	D	D
LM175	Y10	D	X7	D	Y10	D	D	D	D	D
LM176	Y10	D	X8	D	Y10	D	D	D	D	D
LM177	Y10	D	Y16	D	Y10	D	D	D	D	D
LM178	Y10	D	Y17	D	Y10	D	D	D	D	D
LM179	Y10	D	Y18	D	Y10	D	D	D	D	D
LM180	Y10	D	Y15	D	Y10	D	D	D	D	D
LM181	Y10	D	Y15	D	Y10	H	X1	H	D	D
LM182	Y10	D	Y15	D	Y10	D	Y3	D	D	D
LM183	Y10	D	Y16	D	Y10	D	Y3	D	D	D
LM184	Y10	D	Y17	D	Y10	D	Y3	D	D	D
LM185	Y10	D	Y18	D	Y10	D	Y3	D	D	D
LM186	Y10	D	Y15	D	Y10	H	X4	H	D	D
LM187	Y10	D	Y15	D	Y10	D	Y12	D	D	D
LM188	Y10	D	Y16	D	Y10	D	Y12	D	D	D
LM189	Y10	D	Y17	D	Y10	D	Y12	D	D	D
LM190	Y10	D	Y18	D	Y10	D	Y12	D	D	D
LM191	X1	X7	H	H	X1	H	H	H	H	D
LM192	X1	X7	H	H	X1	H	H	H	D	H
LM193	X1	X7	H	H	X1	H	H	H	D	D
LM194	Y1	X7	H	H	Y1	H	H	H	D	D
LM195	Y2	X7	H	H	Y2	H	H	H	D	D
LM196	Y3	X7	H	H	Y3	H	H	H	D	D
LM197	Y3	X7	D	D	Y3	H	H	H	D	D
LM198	Y3	X7	D	D	Y3	D	H	H	D	D
LM199	Y3	X7	D	D	Y3	D	D	H	D	D
LM200	Y3	X7	D	D	Y3	D	D	D	D	D
LM201	Y3	Y15	D	D	Y3	D	D	D	D	D
LM202	Y3	Y16	D	D	Y3	D	D	D	D	D
LM203	Y3	Y17	D	D	Y3	D	D	D	D	D
LM204	Y3	Y18	D	D	Y3	D	D	D	D	D
LM205	Y3	Y15	D	D	Y3	H	X1	H	D	D
LM206	Y3	Y15	D	D	Y3	D	Y3	D	D	D
LM207	Y3	Y16	D	D	Y3	D	Y3	D	D	D
LM208	Y3	Y17	D	D	Y3	D	Y3	D	D	D
LM209	Y3	Y18	D	D	Y3	D	Y3	D	D	D
LM210	Y3	Y15	D	D	Y3	H	X4	H	D	D
LM211	Y3	Y15	D	D	Y3	D	Y12	D	D	D
LM212	Y3	Y16	D	D	Y3	D	Y12	D	D	D
LM213	Y3	Y17	D	D	Y3	D	Y12	D	D	D
LM214	Y3	Y18	D	D	Y3	D	Y12	D	D	D
LM215	X2	X7	H	H	X2	H	H	H	H	D
LM216	X2	X7	H	H	X2	H	H	H	D	H
LM217	X2	X7	H	H	X2	H	H	H	D	D
LM218	Y4	X7	H	H	Y4	H	H	H	D	D
LM219	Y5	X7	H	H	Y5	H	H	H	D	D
LM220	Y6	X7	H	H	Y6	H	H	H	D	D
LM221	Y7	X7	H	H	Y7	H	H	H	D	D
LM222	Y8	X7	H	H	Y8	H	H	H	D	D
LM223	Y9	X7	H	H	Y9	H	H	H	D	D
LM224	Y10	X7	H	H	Y10	H	H	H	D	D
LM225	Y10	X7	D	D	Y10	H	H	H	D	D
LM226	Y10	X7	D	D	Y10	D	H	H	D	D
LM227	Y10	X7	D	D	Y10	D	D	H	D	D
LM228	Y10	X7	D	D	Y10	D	D	D	D	D
LM229	Y10	X8	D	D	Y10	D	D	D	D	D
LM230	Y10	Y16	D	D	Y10	D	D	D	D	D
LM231	Y10	Y17	D	D	Y10	D	D	D	D	D
LM232	Y10	Y18	D	D	Y10	D	D	D	D	D
LM233	Y10	Y15	D	D	Y10	D	D	D	D	D
LM234	Y10	Y15	D	D	Y10	H	X1	H	D	D
LM235	Y10	Y15	D	D	Y10	D	Y3	D	D	D
LM236	Y10	Y16	D	D	Y10	D	Y3	D	D	D
LM237	Y10	Y17	D	D	Y10	D	Y3	D	D	D
LM238	Y10	Y18	D	D	Y10	D	Y3	D	D	D
LM239	Y10	Y15	D	D	Y10	H	X4	H	D	D
LM240	Y10	Y15	D	D	Y10	D	Y12	D	D	D
LM241	Y10	Y16	D	D	Y10	D	Y12	D	D	D
LM242	Y10	Y17	D	D	Y10	D	Y12	D	D	D
LM243	Y10	Y18	D	D	Y10	D	Y12	D	D	D

TABLE 9

Formula 1-2

Ligand name

R11

X11

R101

R102

R103

R104

R14

R15

R16

R17

R18

R19

R20

LFM1

Y10

N—Ph

D

D

D

D

D

Y10

D

D

D

D

D

LFM2

Y10

S

D

D

D

D

D

Y10

D

D

D

D

D

LFM3

Y10

O

D

D

D

D

D

Y10

D

D

D

D

D

LFM4

Y3

O

D

D

D

D

D

Y3

D

D

D

D

D

LFM5

Y10

O

D

D

D

D

D

Y10

D

D

D

D

D

LFM6

Y10

O

D

D

D

D

D

Y10

D

Y3

D

D

D

LFM7

Y10

O

D

D

D

D

D

Y10

D

Y12

D

D

D

TABLE 10

Formula 1-3

Ligand name

R11

X11

R101

R102

R103

R104

R14

R15

R16

R17

R18

R19

R20

LFP1

Y10

N—Ph

D

D

D

D

D

Y10

D

D

D

D

D

LFP2

Y10

S

D

D

D

D

D

Y10

D

D

D

D

D

LFP3

Y10

O

D

D

D

D

D

Y10

D

D

D

D

D

LFP4

Y3

O

D

D

D

D

D

Y3

D

D

D

D

D

LFP5

Y10

O

D

D

D

D

D

Y10

D

D

D

D

D

LFP6

Y10

O

D

D

D

D

D

Y10

D

Y3

D

D

D

LFP7

Y10

O

D

D

D

D

D

Y10

D

Y12

D

D

D

In Tables 8 to 10, X1 to X10 and Y1 to Y18 may be as follows, and “Ph” represents a phenyl group:

In some embodiments, the sensitizer may be represented by Formula 101 or Formula 102, and in this embodiment, the sensitizer may be referred to as a delayed fluorescence sensitizer:

wherein, in Formulae 101 and 102,

A₂₁ may be an acceptor group,

D21 may be a donor group,

m21 may be 1, 2, or 3, and n21 may b 1, 2, or 3,

in Formula 101, a sum of n21 and m21 may be 6 or less, and in Formula 102, a sum of n21 and m21 may be 5 or less, and

R₂₁ may be hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₇-C₆₀ alkyl aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstituted C₂-C₆₀ alkyl heteroaryl group, a substituted or unsubstituted C₁-C₆₀ heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀ heteroarylthio 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), —Ge(Q₁)(Q₂)(Q₃), —C(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), or —P(═S)(Q₁)(Q₂), and a plurality of R₂₁(s) may optionally be bound to each other to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclic group,

wherein Q₁ to Q₃ may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₇-C₆₀ alkyl aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a C₂-C₆₀ alkyl heteroaryl group, a C₁-C₆₀ heteroaryloxy group, a C₁-C₆₀ heteroarylthio group, a monovalent aromatic condensed polycyclic group, a monovalent aromatic condensed heteropolycyclic group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkyl group substituted with at least one of deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof, or a C₆-C₆₀ aryl group substituted with at least one of deuterium, —F, a cyano group, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof.

For example, in Formulae 101 and 102, A₂₁ may be a substituted or unsubstituted π electron-depleted nitrogen-free cyclic group.

In some embodiments, the π electron-depleted nitrogen-free cyclic group may be a benzene group, a heptalene group, an indene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentacene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, a pyrrole group, an isoindole group, an indole group, a furan group, a thiophene group, a benzofuran group, a benzothiophene group, a benzocarbazole group, a dibenzocarbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzothiophene sulfone group, a carbazole group, a dibenzosilole group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, and a triindolobenzene group; or a condensed ring of at least two π electron-depleted nitrogen-free cyclic groups, but embodiments are not limited thereto.

For example, in Formulae 101 and 102, D₂₁ may be: —F, a cyano group, a π electron-depleted nitrogen-containing cyclic group, or any combination thereof;

a C₁-C₆₀ alkyl group, a π electron-depleted nitrogen-containing cyclic group, or π electron-depleted nitrogen-free cyclic group, each substituted with at least one of —F, a cyano group, or any combination thereof; or

a π electron-depleted nitrogen-containing cyclic group substituted with at least one of deuterium, a C₁-C₆₀ alkyl group, a π electron-depleted nitrogen-containing cyclic group, π electron-depleted nitrogen-free cyclic group, or any combination thereof.

In some embodiments, the π electron-depleted nitrogen-free cyclic group may be understood by referring to the description of the π electron-depleted nitrogen-free cyclic groups provided herein.

The π electron-depleted nitrogen-containing cyclic group may be a cyclic group having at least one *—N=*′ moiety. Examples thereof may include: an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyridazine group, a pyrimidine group, an indazole group, a purine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, an azacarbazole group, and a benzimidazolobenzimidazole group; and a condensed ring of at least two π electron-depleted nitrogen-containing cyclic groups.

In some embodiments, the sensitizer may be Groups XI to XV, but embodiments are not limited thereto:

Electron Transport Region in Organic Layer 15

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

In some embodiments, the electron transport region may have a hole blocking layer/an electron transport layer/an electron injection layer structure or an electron transport layer/an electron injection layer structure, but embodiments are not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

The conditions for forming a hole blocking layer, an electron transport layer, and an electron injection layer 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, for example, may include at least one of BCP and Bphen, but embodiments are not limited thereto:

The thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. When the thickness of the hole blocking layer is within any of these ranges, excellent hole blocking characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may include at least one of BCP, BPhen, Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

In some embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments are not limited thereto:

The thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, and in some embodiments, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within any of these ranges, excellent electron transport characteristics may be obtained without a substantial increase in driving voltage.

The electron transport layer may further include a material containing metal, in addition to the materials described above.

The material containing metal may include a Li complex. The Li complex may include, e.g., Compound ET-D1 (LiQ) or Compound ET-D2:

The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19.

The electron injection layer may include at least one of LiQ, LiF, NaCl, CsF, Li₂O, BaO, or any combination thereof.

The thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, and in some embodiments, about 3 Å to about 90 Å. When the thickness of the electron injection layer is within any of these ranges, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

The second electrode 19 may be on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be a material with a relatively low work function, such as a metal, an alloy, an electrically conductive compound, or a mixture thereof. Examples of the material for forming the second electrode 19 may include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), and magnesium-silver (Mg—Ag). In some embodiments, ITO or IZO may be used to form a transmissive second electrode 19 to manufacture a top emission light-emitting device. In some embodiments, the material for forming the second electrode 19 may vary.

Hereinbefore the organic light-emitting device 10 has been described with reference to FIG. 1, but embodiments are not limited thereto.

General Definitions of Terms

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms. Examples thereof include 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. The term “C₁-C₆₀ alkylene group” as used herein refers to a divalent group having substantially the same structure as the C₁-C₆₀ alkyl group.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalent group represented by-OA₁₀₁ (wherein A₁₀₁ is a C₁-C₆₀ alkyl group). Examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a group formed by including at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀ alkyl group. Examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀ alkenylene group” as used herein refers to a divalent group having substantially the same structure as the C₂-C₆₀ alkenyl group.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a group formed by including at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀ alkyl group. Examples thereof include an ethenyl group and a propenyl group. The term “C₂-C₆₀ alkynylene group” as used herein refers to a divalent group having substantially the same structure as the C₂-C₆₀ alkynyl group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalent monocyclic saturated hydrocarbon group including 3 to 10 carbon atoms. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C₃-C₁₀ cycloalkyl group.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom of N, O, P, Si, S, Se, Te, Ge, or a combination thereof as a ring-forming atom and 1 to 10 carbon atoms. Examples thereof include a tetrahydrofuranyl group and a tetrahydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C₁-C₁₀ heterocycloalkyl group.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to a monovalent monocyclic group including 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, wherein the molecular structure as a whole is non-aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylene group” as used herein refers to a divalent group having substantially the same structure as the C₃-C₁₀ cycloalkenyl group.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group including at least one heteroatom of N, O, P, S, Si, Se, Te, Ge, or a combination thereof as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C₁-C₁₀ heterocycloalkenyl group include a 2,3-dihydrofuranyl group and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalent group having substantially the same structure as the C₁-C₁₀ heterocycloalkenyl group.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. The term “C₆-C₆₀ arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀ aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀ aryl group and a C₆-C₆₀ arylene group each include at least two rings, the at least two rings may be fused.

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system having at least one heteroatom N, O, P, Si, S, Se, Te, Ge, or a combination thereof as a ring-forming atom and 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system having at least one heteroatom N, O, P, Se, Te, Ge, or a combination thereof as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C₁-C₆₀ heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group each include at least two rings, the at least two rings may be fused.

The term “C₆-C₆₀ aryloxy group” as used herein refers to-OA₁₀₂ (wherein A₁₀₂ is a C₆-C₆₀ aryl group). The term “C₆-C₆₀ arylthio group” as used herein refers to-SA₁₀₃ (wherein A₁₀₃ is a C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and only carbon atoms (e.g., 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. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group that has two or more condensed rings and a heteroatom N, O, P, Si, and S and carbon atoms (e.g., 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. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀ carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group including 5 to 30 carbon atoms only as ring-forming atoms. The C₅-C₃₀ carbocyclic group may be a monocyclic group or a polycyclic group.

The term “C₁-C₃₀ heterocyclic group” as used herein refers to saturated or unsaturated cyclic group including 1 to 30 carbon atoms and at least one of heteroatom N, O, P, Si, S, Se, Te, Ge, or a combination thereof as ring-forming atoms. The C₁-C₃₀ heterocyclic group may be a monocyclic group or a polycyclic group.

At least one substituent of the substituted C₅-C₃₀ carbocyclic group, the substituted C₁-C₃₀ heterocyclic group, the substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substituted C₁-C₆₀ heteroaryloxy group, the substituted C₁-C₆₀ heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, or a C₁-C₆₀ alkoxy group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro 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-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), —P(═O)(Q₁₈)(Q₁₉), or a combination thereof;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one deuterium, —F, —Cl, —Br, —I, -CD₃, -CD₂H, -CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), —P(═O)(Q₂₈)(Q₂₉), or a combination thereof; or

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉),

wherein Q₁ to Q₉, Q₁₁ to Q₁₉, Q₂₁ to Q₂₉, and Q₃₁ to Q₃₉ may each independently be: hydrogen; deuterium; —F; —Cl, —Br; —I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphoric acid group or a salt thereof; a C₁-C₆₀ alkyl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof; a C₂-C₆₀ alkenyl group; a C₂-C₆₀ alkynyl group; a C₁-C₆₀ alkoxy group; a C₃-C₁₀ cycloalkyl group; a C₁-C₁₀ heterocycloalkyl group; a C₃-C₁₀ cycloalkenyl group; a C₁-C₁₀ heterocycloalkenyl group; a C₆-C₆₀ aryl group unsubstituted or substituted with deuterium, a C₁-C₆₀ alkyl group, a C₆-C₆₀ aryl group, or any combination thereof; a C₆-C₆₀ aryloxy group; a C₆-C₆₀ arylthio group; a C₁-C₆₀ heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic condensed heteropolycyclic group.

Hereinafter, a compound and an organic light-emitting device according to an embodiment will be described in detail with reference to Synthesis Examples and Examples, however, the present disclosure is not limited thereto. The wording “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.

EXAMPLES

Synthesis Example 1: Synthesis of Compound 17

Synthesis of Intermediate (A)

10 grams (g) (23.69 millimole (mmol)) of 2,2′-(oxybis(3,1-phenylene))bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolane) and 7.75 g (23.69 mmol) of bis(3-bromophenyl)amine were added to 120 mL of water and 400 mL of tetrahydrofuran. Then, 1.1 g (0.95 mmol) of tetrakis(triphenylphosphine)palladium(0) and 16.37 g (118.44 mmol) of potassium carbonate were added thereto. The mixture was under reflux at a temperature of 85° C. for 3 hours, followed by cooling. Then, an extraction process was performed by using ethyl acetate. The resulting solid was recrystallized by using methylene chloride and ethyl acetate to thereby obtain 7 g of light yellow solid. (yield: 88%)

LC-Mass (calculated value: 335.13 g/mol, measured value: M+1=336.121 g/mol)

Synthesis of Intermediate (B)

10 g (28.84 mmol) of 9-(3,4,5-trichlorophenyl)-9H-carbazole and 11.13 g (34.62 mmol) of di([1,1′-biphenyl]-4-yl)amine were added to 144 mL of toluene. Then, 0.83 g (1.44 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 1.184 g (2.88 mmol) of SPhos were added thereto, followed by addition of 4.16 g (43.27 mmol) of sodium butoxide. Then, the mixture was heated under reflux at a temperature of 110° C. for 2 hours. An extraction process was performed on the cooled mixture by using water and ethyl acetate. The solvent was removed therefrom, and acetone was added thereto to thereby obtain 8 g of a solid. (yield: 45%)

LC-Mass (calculated value: 630.16 g/mol, measured value: M+1=630.16 g/mol)

Synthesis of Intermediate (C)

6.85 g (10.85 mmol) of Intermediate (B) N-(5-(9H-carbazole-9-yl)-2,3-dichlorophenyl)-N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-4-amine and 4.0 g (11.93 mmol) of Intermediate (A) were added to 542 mL of xylene. Then, 0.99 g (1.08 mmol) of tris(dibenzylideneacetone)dipalladium(0) and 0.89 g (2.17 mmol) of SPhos were added thereto, followed by reflux at a temperature of 125° C. for 3 hours. After cooling the solution, methanol precipitation was performed to obtain 3.3 g of orange solid. (yield: 33%)

LC-Mass (calculated value: 929.32 g/mol, measured value: M+1=930.322 g/mol)

Synthesis of Compound 17

1.4 g (1.14 mmol) of Intermediate (C) was dissolved in 114 mL of t-butyl benzene. Then, the temperature was lowered to a temperature of −78° C., followed by addition of 1.77 mL (2.85 mmol) of t-butyl lithium. The temperature was raised to 60° C. from room temperature 10 minutes later, followed by stirring for 1 hour and 30 minutes. The temperature was lowered to ° C., and 0.22 mL (2.28 mmol) of boron tribromide was added thereto. Then, the temperature was raised to room temperature, followed by stirring for 1 hour. The temperature was lowered to 0° C. again, and 0.38 mL (2.28 mmol) of N,N-diisopropylethylamine was added thereto, followed by stirring at a temperature of 120° C. for 4 hours. The reaction mixture was cooled, and a sodium acetate solution was added thereto to complete the reaction. Then, water was added thereto. Next, t-butyl benzene was extracted to remove a solvent. Then, a purification process using methylene chloride and hexane at a ratio of 1:4 through a silica column to thereby obtain 0.3 g of Compound 17. (yield: 29%)

LC-Mass (calculated value: 903.34 g/mol, measured value: M+1=930.89 g/mol)

Synthesis Example 2: Synthesis of Compound 5

Compound 5 was synthesized in the same manner as in Synthesis of Compound 17, except that Intermediate (D) was used instead of Intermediate (C).

LC-Mass (calculated value: 943.30 g/mol, measured value: M+1=944.533 g/mol)

Example 1-1

An ITO glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm. Then the glass substrate was sonicated in acetone isopropyl alcohol and pure water for about 15 minutes each, and cleaned by exposure to ultraviolet rays and ozone for 30 minutes.

Subsequently, HAT-CN was deposited on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of 100 Å, NPB was deposited on the hole injection layer to form a first hole transport layer having a thickness of 500 Å, TCTA was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 Å, and mCP was deposited on the second hole transport layer to form an electron blocking layer having a thickness of 50 Å.

A first host (H1), a second host (H2), and an emitter (Compound 17) were co-deposited on the electron blocking layer to form an emission layer having a thickness of 400 Å. The first host and the second host were mixed at a ratio of 60:40, and the emitter was 3 wt %, based on the total weight of the first host, the second host, and the emitter.

DBFPO was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å. DBFPO and LiQ were co-deposited on the hole blocking layer at a weight ratio of 5:5 to form an electron transport layer having a thickness of 300 Å. LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Aluminum (Al) was deposited on the electron injection layer to form cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

Example 1-2 and Comparative Examples 1-1 to 1-3

Organic light-emitting devices were manufactured in the same manner as in Example 1-1, except that the compounds shown in Table 11 were used instead of Compound 17 in the formation of an emission layer.

Example 2-1

A glass substrate, on which an ITO electrode was formed, was cut to a size of 50 millimeters (mm)×50 mm×0.5 mm. Then the glass substrate was sonicated in acetone isopropyl alcohol and pure water for about 15 minutes in each solvent, and cleaned by exposure to ultraviolet rays with ozone for 30 minutes.

Subsequently, HAT-CN was deposited on the ITO electrode (anode) of the glass substrate to form a hole injection layer having a thickness of 100 Å, NPB was deposited on the hole injection layer to form a first hole transport layer having a thickness of 500 Å, TCTA was deposited on the first hole transport layer to form a second hole transport layer having a thickness of 50 Å, and mCP was deposited on the second hole transport layer to form an electron blocking layer having a thickness of 50 Å.

A first host (H1), a second host (H2), a sensitizer (S-1), and an emitter (Compound 1) were co-deposited on the electron blocking layer to form an emission layer having a thickness of 400 Å. The first host and the second host were mixed at a ratio of 60:40, and the sensitizer and the emitter were 15 wt % and 1 wt %, based on the total weight of the first host, the second host, the sensitizer, and the emitter, respectively.

DBFPO was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å. DBFPO and LiQ were co-deposited on the hole blocking layer at a weight ratio of 5:5 to form an electron transport layer having a thickness of 300 Å. LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å. Aluminum (Al) was deposited on the electron injection layer to form cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

Example 2-2 and Comparative Examples 2-1 to 2-3

Organic light-emitting devices were manufactured in the same manner as in Example 2-1, except that the compounds shown in Table 12 were used instead of Compound 17 in the formation of an emission layer.

Evaluation Example 2: Evaluation of Characteristics of Organic Light-Emitting Device

The driving voltage, maximum external quantum efficiency (EQE), and lifespan of the organic light-emitting devices manufactured in Example 1-1, Example 1-2, and Comparative Examples 1-1 to 1-3 and Example 2-1, Example 2-2, and Comparative Examples 2-1 to 2-3 were measured by using a Keithley 2400 current voltmeter and a luminance meter (Minolta Cs-1000A). The results thereof are shown in Tables 11 and 12. The maximum external quantum efficiency and lifespan in Tables 11 and 12 are represented as relative values (%).

	TABLE 11
				Lifespan
				(LT99, at
		Driving	Maximum external	6000 nit)
	Compound	voltage	quantum efficiency	(relative
	NO.	(V)	(relative value, %)	value, %)
Example 1	17	4.85	149	220
Example 2	5	4.81	145	217
Comparative	CP1	5.05	115	142
Example 1
Comparative	CP2	5.30	108	157
Example 2
Comparative	CP3	5.25	112	130
Example 3

	TABLE 12
				Lifespan
				(LT99, at
		Driving	Maximum external	6000 nit)
	Compound	voltage	quantum efficiency	(relative
	NO.	(V)	(relative value, %)	value, %)
Example 1	17	4.45	113	145
Example 2	5	4.3	111	148
Comparative	CP1	4.62	105	117
Example 1
Comparative	CP2	4.77	108	120
Example 2
Comparative	CP3	4.53	101	112
Example 3

Referring to the results of Table 11, the organic light-emitting devices of Examples 1-1 and 1-2 were found to have improved driving voltage, maximum external quantum efficiency, and lifespan characteristics, as compared with the organic light-emitting devices of Comparative Examples 1-1 to 1-3.

Referring to the results of Table 12, the organic light-emitting devices of Examples 2-1 and 2-2 were found to have improved driving voltage, maximum external quantum efficiency, and lifespan characteristics, as compared with the organic light-emitting devices of Comparative Examples 2-1 to 2-3.

As apparent from the foregoing description, when the condensed cyclic compound is used, an organic light-emitting device and an electron apparatus including the organic light-emitting device may have a high efficiency and long lifespan characteristics.

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

While one or more 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 as defined by the following claims.

Claims

1. A condensed cyclic compound represented by one of Formulae 1 to 4:

2. The condensed cyclic compound of claim 1, wherein A1 to A3 in Formulae 1 to 4 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a fluorene group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a quinoline group, an isoquinoline group, a quinoxaline group, or a quinazoline group.

3. The condensed cyclic compound of claim 1, wherein Ar1 to Ar7 in Formulae 1 to 4 are each independently a substituted or unsubstituted C6-C60 arylene group, a substituted or unsubstituted C1-C60 heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

4. The condensed cyclic compound of claim 1, wherein Ar1 to Ar7 in Formulae 1 to 4 are each independently: a cyclopentane group, a cyclohexane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, a pentalene group, an indene group, an azulene group, a heptalene group, an acenaphthene group, a fluorene group, a spiro-bifluorene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a phthalazine group, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, an indole group, a benzofuran group, a benzothiophene group, a benzosilole group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzosilole group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —SF5, a hydroxyl group, a cyano group, a nitro group, a C1-C60 alkyl group, a C1-C60 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylenyl group, a naphthacenyl group, a picenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl 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, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, or any combination thereof.

5. The condensed cyclic compound of claim 1, wherein Ar1 to Ar5 in Formulae 1 to 3 are each independently a group represented by one of Formulae Ar-1 to Ar-3, and Ar6 and Ar7 in Formula 4 are each independently a group represented by Formula Ar-4:

6. The condensed cyclic compound of claim 1, wherein a moiety represented by

7. The condensed cyclic compound of claim 1, wherein R1 to R5, R10, R20, R30, R40, R50, and R60 in Formulae 1 to 4 are each independently: hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, or a phosphoric acid group or a salt thereof;a C1-C20 alkyl group or a C1-C20 alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro 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, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, —N(Q31)(Q32), or any combination thereof;a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C1-C20 alkyl group, a C2-C20 alkenyl group, a C2-C20 alkynyl group, a C1-C20 alkoxy group, a cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pentalenyl group, an indenyl group, an azulenyl group, a heptalenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl 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 pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indolyl group, an isoindolyl group, a benzimidazolyl group, an indazolyl group, a carbazolyl 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 phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a furanyl group, a thiophenyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a thiadiazolyl group, a silolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoxazolyl group, a benzothiazolyl group, a benzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, —N(Q31)(Q32), or any combination thereof; or—N(Q1)(Q2),wherein Q1, Q2, Q31, and Q32 are each independently: a C1-C10 alkyl group; a C1-C10 alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.

8. The condensed cyclic compound of claim 1, wherein R1 to R5, R10, R20, R30, R40, R50, and R60 in Formulae 1 to 4 are each independently: hydrogen, deuterium, —F, or a cyano group;a C1-C20 alkyl group or a C1-C20 alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof;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 pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, or a dibenzothiophenyl group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C1-C20 alkyl group, a C1-C20 alkoxy 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 pyridinyl group, a pyrimidinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or any combination thereof; or—N(Q1)(Q2),wherein Q1 and Q2 are each independently: a C1-C10 alkyl group; a C1-C10 alkoxy group; or a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, each unsubstituted or substituted with deuterium, a C1-C10 alkyl group, a phenyl group, or any combination thereof.

9. The condensed cyclic compound of claim 1, wherein the condensed cyclic compound is represented by Formula 1A, Formula 2A, Formula 3A, or Formula 4A:

10. The condensed cyclic compound of claim 1, wherein the condensed cyclic compound is represented by Formula 1A-1, Formula 2A-1, Formula 3A-1, or Formula 4A-1:

11. The condensed cyclic compound of claim 10, wherein Ar11, Ar12, Ar2, Ar31, Ar32, Ar4, and Ar5 in Formulae 1A-1 to 3A-1 are each independently a group represented by one of Formulae Ar-1 to Ar-3, and Ar6 and Ar7 in Formula 4A-1 are each independently a group represented by Formula Ar-4:

12. The condensed cyclic compound of claim 1, wherein the condensed cyclic compound is represented by Formula 1A-2, Formula 2A-2, Formula 3A-2, or Formula 4A-2:

13. The condensed cyclic compound of claim 1, wherein the condensed cyclic compound is represented by one of Compounds 1 to 40:

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

15. The organic light-emitting device of claim 14, wherein the emission layer comprises the condensed cyclic compound.

16. The organic light-emitting device of claim 14, wherein the emission layer comprises a host and a dopant, and the dopant comprises the condensed cyclic compound.

17. The organic light-emitting device of claim 15, wherein the emission layer emits delayed fluorescence.

18. The organic light-emitting device of claim 15, wherein the emission layer emits blue light.

19. The organic light-emitting device of claim 14, wherein the emission layer comprises a host, an emitter, and a sensitizer, the host, the emitter, and the sensitizer are different from one other, and the condensed cyclic compound is comprised in the emitter.

20. An electronic apparatus comprising the organic light-emitting device of claim 14.