CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

CROSS-REFERENCE TO RELATED APPLICATION(S)

This application claims priority to and benefits of Korean Patent Application No. 10-2020-0018568 under 35 U.S.C. § 119, filed on Feb. 14, 2020, in the Korean Intellectual Property Office, the entire contents of which are incorporated herein by reference.

BACKGROUND
1. Technical Field

Embodiments relate to a condensed cyclic compound and an organic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that produce full-color images, and also have wide viewing angles, high contrast ratios, short response times, and excellent characteristics in terms of brightness, driving voltage, and response speed, compared to devices in the art.

The organic light-emitting device may include a first electrode disposed on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode, which are sequentially disposed on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.

SUMMARY

Embodiments include a condensed cyclic compound and an organic light-emitting device including the same.

Additional embodiments 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 embodiments of the disclosure.

In an embodiment, a condensed cyclic compound is represented by Formula 1:

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wherein in Formula 1,

ring A₁to ring A₄may each independently be a C₅-C₆₀carbocyclic group,

ring B1 may be selected from a C₅-C₆₀carbocyclic group and a C₁-C₆₀heterocyclic group,

Y₁and Y₂may each independently be selected from B and P(═O),

X₁may be O, N(R₁), S, or Se,

X₂may be O, N(R₂), S, or Se,

X₃may be O, N(R₃), S or Se,

X₄may be O, N(R₄), S, or Se,

L₁to L₅may each independently be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀heterocyclic group,

a1 to a5 may each independently be an integer from 0 to 3, wherein, when a1 is 0, *-(L₁)_a1-*′ indicates a single bond, when a2 is 0, *-(L₂)_a2-*′ indicates a single bond, when a3 is 0, *-(L₃)_a3-*′ indicates a single bond, when a4 is 0, *-(L₄)_a4-*′ indicates a single bond, and when a5 is 0, *-(L₅)_a5-*′ indicates a single bond,

Ar₁to Ar₅may each independently be selected from 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 substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio 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(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

b1 to b5 may each independently be an integer from 0 to 3,

c1 to c5 may each independently be an integer from 0 to 10,

R₁to R₄may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

R₁to R₄may optionally be linked to a neighboring group via a single bond, —C(Q₄)(Q₅)-, —Si(Q₄)(Q₅)-, —O—, —S—, —N(Q₄)-, —B(Q₄)-, C(═O)—, —S(═O)₂—, —S(═O)(Q₄)-, and —P(═O)(Q₄)- to form a heteroring,

Z₁and Z₂may each independently be selected from an electron withdrawing group and a C₁-C₆₀alkyl group in which at least one electron withdrawing group is substituted,

t1 and t2 may each independently be an integer from 1 to 10,

at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₂-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₂-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₂-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from

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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group,

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂),

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, each substituted with at least one selected from 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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, a terphenyl group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

Q₁to Q₅, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be selected from 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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryl group substituted with a C₁-C₆₀alkyl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group, and

* and *′ each indicate a binding site to a neighboring group.

In an embodiment, an organic light-emitting device may include a first electrode, a second electrode facing the first electrode, an organic layer disposed between the first electrode and the second electrode and including an emission layer, and a condensed cyclic compound represented by Formula 1.

In an embodiment, the first electrode may be an anode, and the second electrode may be a cathode. The organic layer may include the condensed cyclic compound, a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode. The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or any combination thereof. The electron transport region may include a buffer layer, a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In an embodiment, the emission layer may include the condensed cyclic compound.

In an embodiment, the condensed cyclic compound included in the emission layer may be a delayed fluorescence emitter, and the emission layer may emit delayed fluorescence.

In an embodiment, the host may include an anthracene compound, a carbazole compound, a benzimidazole compound, a phosphine oxide compound, an arylamine compound, a styrylamine compound, or a combination thereof.

In an embodiment, the emission layer may be a first emission layer that emits first color light, and the organic light-emitting device may further include between the first electrode and the second electrode i) a second emission layer that emits second color light, or ii) a second emission layer that emits second color light and a third emission layer that emits third color light. The first color light and the second color light may be emitted as mixed light, or the first color light, the second color light, and the third color light may be emitted as mixed light.

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, features, and advantages of certain embodiments of the disclosure will be more apparent from the following description taken in conjunction with the accompanying drawings, in which:

FIGS. 1 to 4 are each a schematic cross-sectional view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION OF THE EMBODIMENTS

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 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 of the detailed description.

As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. For example, “A and/or B” may be understood to mean “A, B, or A and B.” The terms “and” and “or” may be used in the conjunctive or disjunctive sense and may be understood to be equivalent to “and/or”. Throughout the disclosure, the expression “at least one of A, B, or C” may indicate only A, only B, only C, both A and B, both A and C, both B and C, all of A, B, and C, or variations thereof.

The term “at least one of” is intended to include the meaning of “at least one selected from the group consisting of” for the purpose of its meaning and interpretation. For example, “at least one of A and B” may be understood to mean “A, B, or A and B.” When preceding a list of elements, the term, “at least one of,” modifies the entire list of elements and does not modify the individual elements of the list.

As used herein, the singular forms “a,” “an” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “comprises”, “includes”, and/or “contains” as used herein specify the presence of stated features or components, but do not preclude the presence or addition of one or more other features or components.

It will be understood that when a layer, region, or component is referred to as being “on” or “onto” another layer, region, or component, it may be directly or indirectly formed on the other layer, region, or component. For example, intervening layers, regions, or components may be present.

The spatially relative terms “below”, “beneath”, “lower”, “above”, “upper”, or the like, may be used herein for ease of description to describe the relations between one element or component and another element or component as illustrated in the drawings. It will be understood that the spatially relative terms are intended to encompass different orientations of the device in use or operation, in addition to the orientation depicted in the drawings. For example, in the case where a device illustrated in the drawing is turned over, the device positioned “below” or “beneath” another device may be placed “above” another device. Accordingly, the illustrative term “below” may include both the lower and upper positions. The device may also be oriented in other directions and thus the spatially relative terms may be interpreted differently depending on the orientations.

The terms “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” may mean within one or more standard deviations, or within ±20%, 10%, or 5% of the stated value.

Sizes of elements in the drawings may be exaggerated for convenience of explanation. In other words, since sizes and thicknesses of components in the drawings are arbitrarily illustrated for convenience of explanation, the following embodiments of the disclosure are not limited thereto.

A condensed cyclic compound according to an embodiment is represented by Formula 1:

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In Formula 1,

ring A₁to ring A₄may each independently be a C₅-C₆₀carbocyclic group, and ring B₁may be selected from a C₅-C₆₀carbocyclic group and a C₁-C₆₀heterocyclic group.

In an embodiment, ring A₁to ring A₄may each independently be a C₆-C₆₀aryl group, and ring B₁may be selected from a C₆-C₆₀aryl group and a C₁-C₆₀heteroaryl group.

In an embodiment, ring A₁to ring A₄may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group, and

ring B₁may be selected from a benzene group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a quinoxaline group, a phthalazine group, a quinazoline group, a cinnoline group, and a naphthyridine group.

For example, ring A₁and ring A₂may each independently be a benzene group or a naphthalene group,

ring A₃and ring A₄may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, and a perylene group, and

ring B₁may be a benzene group.

For example, rings A₁to ring A₄may each independently be a benzene group, and ring B₁may be a benzene group.

In Formula 1, Y₁and Y₂may each independently be selected from B and P(═O).

In an embodiment, Y₁and Y₂may be identical to each other. For example, Y₁and Y₂may each independently be B.

In Formula 1, X₁may be O, N(R₁), S, or Se, X₂may be O, N(R₂), S, or Se, X₃may be O, N(R₃), S, or Se, and X₄may be O, N(R₄), S, or Se.

In an embodiment, (i) X₁may be N(R₁), X₂may be N(R₂), X₃may be N(R₃), and X₄may be N(R₄); (ii) X₁may be N(R₁), X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be N(R₄); (iii) X₁may be N(R₁), X₂may be N(R₂), X₃may be N(R₃), and X₄may be O, S, or Se; (iv) X₁may be N(R₁), X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be O, S, or Se; (v) X₁may be O, S, or Se, X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be N(R₄); (vi) X₁may be N(R₁), X₂may be O, S, or Se, X₃may be N(R₃), and X₄may be O, S, or Se; or (vii) X₁may be O, S, or Se, X₂may be O, S, or Se, X₃may be O, S, or Se, and X₄may be O, S, or Se.

In embodiments, both Yi and Y₂may be B, and (i) X₁may be N(R₁), X₂may be N(R₂), X₃may be N(R₃), and X₄may be N(R₄); (ii) X₁may be N(R₁), X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be N(R₄); (iii) X₁may be N(R₁), X₂may be N(R₂), X₃may be N(R₃), and X₄may be O, S, or Se; (iv) X₁may be N(R₁), X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be O, S, or Se; (v) X₁may be O, S, or Se, X₂may be N(R₂), X₃may be O, S, or Se, and X₄may be N(R₄); (vi) X₁may be N(R₁), X₂may be O, S, or Se, X₃may be N(R₃), and X₄may be O, S, or Se; or (vii) X₁may be O, S, or Se, X₂may be O, S, or Se, X₃may be O, S, or Se, and X₄may be O, S, or S.

In Formula 1, Li to L₅may each independently be selected from a substituted or unsubstituted C₅-C₆₀carbocyclic group and a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In an embodiment, Li to L₅may each independently be selected from:

a benzene group, a pentalene group, an indene group, a naphthalene group, an azulene group, a heptalene group, an indacene group, an acenaphthalene 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 pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pyrrole group, a thiophene group, a furan group, a silole 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 pyrimidine group, a pyridazine group, a triazine group, a benzofuran group, a benzothiophene group, a dibenzofuran group, a dibenzothiophene group, a carbazole group, a benzosilole group, a dibenzosilole group, a quinoline group, an isoquinoline group, a benzimidazole group, an imidazopyridine group, and an imidazopyrimidine group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a carbazolyl group, a benzosilolyl group, a dibenzosilolyl group, a quinolinyl group, an isoquinolinyl group, a benzimidazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

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

In Formula 1, a1 to a5 may each independently be an integer from 0 to 3, wherein, when a1 is 0, *-(L₁)_a1-*′ indicates a single bond, when a2 is 0, *-(L₂)_a2-*′ indicates a single bond, when a3 is 0, *-(L₃)_a3-*′ indicates a single bond, when a4 is 0, *-(L₄)_a4-*′ indicates a single bond, and when a5 is 0, *-(L₅)_a5-*′ indicates a single bond.

In Formula 1, Ar₁to Ar₅may each independently be selected from 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 substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₁-C₆₀heteroaryloxy group, a substituted or unsubstituted C₁-C₆₀heteroarylthio 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(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂).

In an embodiment, Ar₁to Ar₅may each independently be selected from:

hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₃-C₁₀cycloalkyl group, a C₆-C₂₀aryl group, a C₇-C₂₀aryl alkyl group, a C₁-C₂₀heteroaryl group, a C₂-C₂₀heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

a C₆-C₂₀aryl group, a C₇-C₂₀aryl alkyl group, a C₁-C₂₀heteroaryl group, a C₂-C₂₀heteroaryl alkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, a cyano group, a C₁-C₁₀alkyl group, and a C₃-C₁₀cycloalkyl group.

For example, Ar₁to Ar₅may each independently be selected from:

hydrogen, deuterium, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group;

a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group, each substituted with at least one selected from deuterium, —F, a cyano group;

a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, a cyano group, a cyclopentyl group, a cyclohexyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

In Formula 1, b1 to b5 may each independently be an integer from 0 to 3, and c1 to c5 may each independently be an integer from 0 to 10.

In Formula 1, R₁to R₄may each independently be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In an embodiment, R₁to R₄may each independently be selected from:

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-cyclopentane-fluorenyl group, a spiro-cyclohexane-fluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzoxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a phenoxazinyl group, and a phenothiazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a spiro-cyclopentane-fluorenyl group, a spiro-cyclohexane-fluorenyl group, a spiro-fluorene-benzofluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzoxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a phenoxazinyl group, a phenothiazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), and —B(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃may each independently be selected from hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₆-C₂₀aryl group, a C₆-C₂₀aryl group substituted with a C₁-C₂₀alkyl group, a C₆-C₂₀aryl group substituted with a C₆-C₂₀aryl group, a C₁-C₂₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, and a terphenyl group.

For example, R₁to R₄may each independently be selected from:

a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzoxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a phenoxazinyl group, and a phenothiazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pyrrolyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a furanyl group, a benzofuranyl group, a thiophenyl group, a benzothiophenyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a benzoxazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a phenoxazinyl group, and a phenothiazinyl group.

In Formula 1, R₁to R₄may optionally be linked to a neighboring group via a single bond, —C(Q₄)(Q₅)-, —Si(Q₄)(Q₅)-, —O—, —S—, —N(Q₄)-, —B(Q₄)-, C(═O)—, —S(═O)₂—, —S(═O)(Q₄)-, or —P(═O)(Q₄)- to form a heteroring.

In Formula 1, Z₁and Z₂may each independently be selected from an electron withdrawing group and a C₁-C₆₀alkyl group substituted with at least one electron withdrawing group,

The electron withdrawing group refers to a group that tends to attract an electron adjacent to hydrogen in a molecule.

For example, the electron withdrawing group may include a halogen group, a cyano group, a nitro group, a carbonyl group, or an alkyl group substituted in which at least one selected from a halogen group, a cyano group, a nitro group, and a carbonyl group is substituted. Without a particular limitation, the electron withdrawing group may include any atom having a stronger tendency to attract an electron than hydrogen.

For example, the electron withdrawing group may be selected from:

—F, —Cl, —Br, —I, and —CN; and

a C₁-C₂₀alkyl group substituted with at least one selected from —F, —Cl, —Br, —I, and —CN.

In Formula 1, t1 and t2 may each independently be an integer from 1 to 10. In an embodiment, t1 and t2 may each independently be 1 or 2.

In an embodiment, in Formula 1, ring A₁and ring A₂may each independently be a benzene group, t1 and t2 may each independently be 1 or 2, and c1 and c2 may each independently be 1 or 2.

In an embodiment, Formula 1 may be represented by one of Formulae 1-1 to 1-36:

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In Formulae 1-1 to 1-36,

A₃, A₄, B1, Y₁, Y₂, X₁, X₂, X₃, X₄, L₃, L₄, L₅, a3, a4, a5, Ar₃, Ar₄, Ar₅, b3, b4, b5, c3, c4, and c5 are the same as described above,

L₁₁, L₁₂, and L₁₃may each be understood as described in connection with Li,

all, a12, and a13 may each be understood as described in connection with a1,

Ar₁₁, Ar₁₂, and Ar₁₃may each be understood as described in connection with Ar₁,

b11, b12, and b13 may each be understood as described in connection with b1,

Ar₂₁, Ar₂₂, and Ar₂₃may each be understood as described in connection with Ar₂,

b21, b22, and b23 may each be understood as described in connection with b2,

Z₁₁, Z₁₂, and Z₁₃may each be understood as described in connection with Z₁, and

Z₂₁, Z₂₂, and Z₂₃may each be understood as described in connection with Z₂.

In an embodiment, in Formulae 1-1 to 1-36,

Z₁₁, Z₁₃, Z₂₁, and Z₂₃may each independently be selected from:

—F, —Cl, —Br, —I, and —CN; and

a C₁-C₂₀alkyl group substituted with at least one selected from —F, —Cl, —Br, —I, and —CN, and

Z₁₂and Z₂₂may each independently be selected from:

—F, —Cl, —Br, and —I; and

a C₁-C₂₀alkyl group substituted with at least one selected from —F, —Cl, —Br, —I, and —CN.

For example, in Formulae 1-1 to 1-36,

Z₁₁, Z₁₃, Z₂₁, and Z₂₃may each independently be selected from:

—F and —CN; and

a C₁-C₂₀alkyl group substituted with at least one selected from —F and —CN, and

Z₁₂and Z₂₂may each independently be selected from:

—F and a C₁-C₂₀alkyl group substituted with at least one —F.

In an embodiment, in Formulae 1-1 to 1-36, all of a11 to a13 and a21 to a23 may be 0, and all of Ar₁₁to Ar₁₃and Ar₂₁to Ar₂₃may be hydrogen.

In an embodiment, the condensed cyclic compound may be selected from Compounds 1 to 48, but embodiments are not limited thereto:

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The condensed cyclic compound represented by Formula 1 is capable of reverse intersystem crossing from a triplet excited state to a singlet excited state through thermal activity even at room temperature, resulting in delayed fluorescence. Since excitons in the triplet state are used for emission, luminescence efficiency may be improved.

In an embodiment, the condensed cyclic compound represented by Formula 1 may satisfy Equation 1:

ΔE_ST=S1−T1≤0.3 eV. <Equation 1>

In Equation 1, S1 is the singlet energy level of the condensed cyclic compound, and

T1 is the triplet energy level of the condensed cyclic compound.

Since the condensed cyclic compound according to an embodiment includes the condensed cyclic structure represented by Formula 1, the highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) are separated by multiple resonance between an N atom and a B atom to obtain thermally active delayed fluorescence (TADF) characteristics. Since the condensed cyclic compound has a rigid structure in which condensed cyclic group moieties, including boron atoms, share a benzene ring and are condensed, the structural change before and after the transition is small, thereby improving stability.

Since the condensed cyclic compound represented by Formula 1 has an amplified multiple resonance effect by including two boron atoms in one molecule, improved absorption and high luminescence efficiency may be obtained.

The electron withdrawing group bound to the condensed cyclic compound represented by Formula 1 contributes to the LUMO separation during the separation of the HOMO and the LUMO, thereby forming multiple resonance at the atomic level.

Compared to a case where the condensed cyclic compound represented by Formula 1 has an electron donating group while the multiple resonance is maintained by introducing an electron withdrawing group, the bond dissociation energy (BDE) is improved, thereby improving lifespan characteristics.

Upon the introduction of the electron withdrawing group, the spin orbit coupling between the triplet excited state and the singlet excited state is enhanced, thereby increasing the kRISC values and improving the TADF characteristics.

Since the condensed cyclic compound represented by Formula 1 has relatively high charge (hole or electron) transport ability, an exciton formation ratio in an emission layer of an organic light-emitting device using the condensed cyclic compound represented by Formula 1 may be improved. Accordingly, the organic light-emitting device may have low driving voltage, high efficiency, long lifespan, and high maximum quantum efficiency.

Synthesis methods of the condensed cyclic compound represented by Formula 1 may be recognizable by one of ordinary skill in the art by referring to Examples provided below.

At least one of such condensed cyclic compounds represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the condensed cyclic compounds may be included in at least one selected from a hole transport region, an electron transport region, and an emission layer. In embodiments, the condensed cyclic compound represented by Formula 1 may be used as a material for a capping layer located outside the pair of electrodes of an organic light-emitting device.

In an embodiment, provided is an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer disposed between the first electrode and the second electrode and including an emission layer; and at least one condensed cyclic compound represented by Formula 1.

In an embodiment, the organic layer of the organic light-emitting device may include the condensed cyclic compound represented by Formula 1.

In an embodiment, the first electrode may be an anode,

the second electrode may be a cathode,

the organic layer may include the condensed cyclic compound represented by Formula 1,

the organic layer may further 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,

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

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

In an embodiment, the emission layer of the organic light-emitting device may include the condensed cyclic compound. For example, the condensed cyclic compound included in the emission layer is a delayed fluorescence emitter, and the emission layer may emit delayed fluorescence.

In an embodiment, the emission layer may further include a host, the condensed cyclic compound included in the emission layer may be a dopant, and an amount of the host included in the emission layer may be greater than an amount of the condensed cyclic compound included in the emission layer. For example, the amount of the condensed cyclic compound may be from about 0.01 parts by weight to about 49.99 parts by weight based on 100 parts by weight of the emission layer.

For example, the host included in the emission layer may include an anthracene compound, a carbazole compound, a benzimidazole compound, a phosphine oxide compound, an arylamine compound, a styrylamine compound, or any combination thereof.

In an embodiment, the emission layer of the organic light-emitting device may include the condensed cyclic compound, and the emission layer may emit light having a maximum emission wavelength in a range of about 420 nm to about 480 nm.

In an embodiment, the emission layer may be a first emission layer that emits first color light,

the organic light-emitting device may further include between the first electrode and the second electrode i) at least one second emission layer that emits second color light or ii) at least one second emission layer that emits second color light and at least one third emission layer that emits third color light,

the maximum emission wavelength of the first color light, the maximum emission wavelength of the second color light, and the maximum emission wavelength of the third color light may be either identical to or different from each other, and

the first color light and the second color light may be emitted as mixed light, or the first color light, the second color light, and the third color light may be emitted as mixed light.

In an embodiment, the first color light, the second color light, and the third color light may have colors different from each other.

In an embodiment, a wavelength of maximum emission of the first color light, a wavelength of maximum emission of the second color light, and a wavelength of maximum emission of the third color light may be identical to each other.

In an embodiment, provided is an electronic apparatus including: the organic light-emitting device; and a thin-film transistor, wherein the first electrode of the organic light-emitting device electrically contacts one of a source electrode and a drain electrode of the thin-film transistor.

The term “an organic layer” as used herein refers to a single layer and/or multiple layers disposed between the first electrode and the second electrode of an organic light-emitting device. A material included in the “organic layer” is not limited to an organic material.

[Description of FIG. 1]

FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to an embodiment. The organic light-emitting device 10 includes a first electrode 110, an organic layer 150, and a second electrode 190.

Hereinafter, the structure of the organic light-emitting device 10 according to an embodiment and a method of manufacturing the organic light-emitting device 10 will be described in connection with FIG. 1.

[First Electrode 110]

In FIG. 1, a substrate may be disposed under the first electrode 110 or above the second electrode 190. The substrate may be a glass substrate or a plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be selected from materials with a high work function to facilitate hole injection.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, but embodiments are not limited thereto. In embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflectable electrode, a material for forming the first electrode 110 may be selected from magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinations thereof, but embodiments are not limited thereto.

The first electrode 110 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.

[Organic Layer 150]

The organic layer 150 is located on the first electrode 110. The organic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport region between the first electrode 110 and the emission layer, and an electron transport region between the emission layer and the second electrode 190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including different materials, or iii) a multi-layered structure having layers including different materials.

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

For example, the hole transport region may have a single-layered structure including a single layer including different materials, or a multi-layered structure having a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein for each structure, constituting layers are sequentially stacked from the first electrode 110 in this stated order, but the structure of the hole transport region is not limited thereto.

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

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In Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

L₂₀₅may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted or unsubstituted C₁-C₂₀alkylene group, a substituted or unsubstituted C₂-C₂₀alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁and R₂₀₂may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R₂₀₃and R₂₀₄may optionally be linked to each other via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

In an embodiment, in Formulae 201 and 202,

L₂₀₁to L₂₀₅may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a rubicenylene group, a coronenylene group, an ovalenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, and a pyridinylene group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃) and —N(Q₃₁)(Q₃₂),

Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

In embodiments, xa5 may be 1, 2, 3, or 4.

In embodiments, R₂₀₁to R₂₀₄and Q₂₀₁may each independently be selected from a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃are the same as described above.

In embodiments, at least one selected from R₂₀₁to R₂₀₃in Formula 201 may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments are not limited thereto.

In embodiments, in Formula 202, i) R₂₀₁and R₂₀₂may be linked to each other via a single bond, and/or ii) R₂₀₃and R₂₀₄may be linked to each other via a single bond.

In embodiments, R₂₀₁to R₂₀₄in Formula 202 may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments are not limited thereto.

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

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In an embodiment, the compound represented by Formula 201 may be represented by Formula 201-2, but embodiments are not limited thereto:

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In embodiments, the compound represented by Formula 201 may be represented by Formula 201-2(1), but embodiments are not limited thereto:

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In embodiments, the compound represented by Formula 201 may be represented by Formula 201A:

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In embodiments, the compound represented by Formula 201 may be represented-by-Formula-201A(1), but embodiments are not limited thereto:

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In embodiments, the compound represented by Formula 201 may be represented by Formula 201A-1, but embodiments are not limited thereto:

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In an embodiment, the compound represented by Formula 202 may be represented by Formula 202-1:

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In embodiments, the compound represented by Formula 202 may be represented by Formula 202-1(1):

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In embodiments, the compound represented by Formula 202 may be represented by Formula 202A:

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In embodiments, the compound represented by Formula 202 may be represented by Formula 202A-1:

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In Formulae 201-1, 201-2, 201-2(1), 201A, 201A(1), 201A-1, 202-1, 202-1(1), 202A, and 202A-1,

L₂₀₁to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂to R₂₀₄are the same as described above,

L₂₀₅may be selected from a phenylene group and a fluorenylene group,

X₂₁₁may be selected from O, S, and N(R₂₁₁),

X₂₁₂may be selected from O, S, and N(R₂₁₂),

R₂₁₁and R₂₁₂may each be understood as described in connection with R₂₀₃, and

R₂₁₃to R₂₁₇may each independently be selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, an ovalenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, and a pyridinyl group.

The hole transport region may include at least one compound selected from Compounds HT1 to HT48, but embodiments are not limited thereto:

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A thickness of the hole transport region may be in a range of about 100 Å to about 10,000 Å. For example, the thickness of the hole transport region may be in a range of about 100 Å to about 1,000 Å. When the hole transport region includes at least one selected from a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, and the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å. For example, the thickness of the hole injection layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the hole transport layer may be in a range of about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer, and the electron blocking layer may block the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may include the materials as described above.

[P-Dopant]

The hole transport region may further include a charge-generation material for the improvement of conductive properties. The charge-generation material may be homogeneously or non-homogeneously dispersed in the hole transport region.

The charge-generation material may be, for example, a p-dopant.

In an embodiment, the LUMO energy level of the p-dopant may be −3.5 eV or less.

The p-dopant may include at least one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments are not limited thereto.

In an embodiment, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) and F4-2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,12-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221,

but embodiments are not limited thereto:

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In Formula 221,

R₂₂₁to R₂₂₃may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and at least one selected from R₂₂₁to R₂₂₃may have at least one substituent selected from a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀alkyl group substituted with —F, a C₁-C₂₀alkyl group substituted with —Cl, a C₁-C₂₀alkyl group substituted with —Br, and a C₁-C₂₀alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

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, or a blue emission layer, according to a sub-pixel. In embodiments, the emission layer may have a stacked structure of two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer, in which the two or more layers contact each other or are separated from each other. In embodiments, the emission layer may include two or more materials selected from a red light-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

The emission layer may include a host and a dopant. The dopant may include at least one selected from a phosphorescent dopant and a fluorescent dopant.

An amount of the dopant in the emission layer may be, based on about 100 parts by weight of the host, in a range of about 0.01 parts by weight to about 15 parts by weight, but embodiments are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the emission layer may be in a range of about 200 Å to about 600 Å. When the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

[Host in Emission Layer]

In embodiments, the host may include a compound represented by Formula 301:

[Ar₃₀₁]_xb11-[(L₃₀₁)_xb1-R₃₀₁]_xb21 <Formula 301>

In Formula 301,

Ar₃₀₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁may be selected from 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-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl 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), and —P(═O)(Q₃₀₁)(Q₃₀₂), and

xb21 may be an integer from 1 to 5, and

Q₃₀₁to Q₃₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments are not limited thereto.

In an embodiment, Ar₃₀₁in Formula 301 may be selected from:

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, and a dibenzothiophene group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group, but embodiments are not limited thereto.

When xb11 in Formula 301 is 2 or more, two or more Ar₃₀₁(s) may be linked to each other via a single bond.

In embodiments, the compound represented by Formula 301 may be represented by Formula 301-1 or 301-2:

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In Formulae 301-1 and 301-2

ring A₃₀₁to ring A₃₀₄may each independently be selected from a benzene ring, a naphthalene ring, a phenanthrene ring, a fluoranthene ring, a triphenylene ring, a pyrene ring, a chrysene ring, a pyridine ring, a pyrimidine ring, an indene ring, a fluorene ring, a spiro-bifluorene ring, a benzofluorene ring, a dibenzofluorene ring, an indole ring, a carbazole ring, a benzocarbazole ring, a dibenzocarbazole ring, a furan ring, a benzofuran ring, a dibenzofuran ring, a naphthofuran ring, a benzonaphthofuran ring, a dinaphthofuran ring, a thiophene ring, a benzothiophene ring, a dibenzothiophene ring, a naphthothiophene ring, a benzonaphthothiophene ring, and a dinaphthothiophene ring,

X₃₀₁may be O, S, or N-[(L₃₀₄)_xb4-R₃₀₄],

R₃₁₁to R₃₁₄may each independently be selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁to Q₃₃are the same as described above,

L₃₀₂to L₃₀₄may each independently be understood as described in connection with L₃₀₁,

xb2 to xb4 may each independently be understood as described in connection with xb1, and

R₃₀₂to R₃₀₄may each independently be understood as described in connection with R₃₀₁.

For example, L₃₀₁to L₃₀₄in Formulae 301, 301-1, and 301-2 may each independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, a pentacenylene group, a thiophenylene group, a furanylene group, a carbazolylene group, an indolylene group, an isoindolylene group, a benzofuranylene group, a benzothiophenylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzocarbazolylene group, a dibenzosilolylene group, a pyridinylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a thiadiazolylene group, an oxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an imidazopyridinylene group, an imidazopyrimidinylene group, and an azacarbazolylene group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl 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, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃are the same as described above.

In an embodiment, R₃₀₁to R₃₀₄in Formulae 301, 301-1, and 301-2 may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl 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, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and an azacarbazolyl group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenyl group, a thiophenyl group, a furanyl group, a carbazolyl group, an indolyl group, an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl 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, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃are the same as described above.

In embodiments, the host may include an alkaline earth metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), an Mg complex, and a Zn complex.

The host may include at least one selected from 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and at least one selected from Compounds H1 to H55, but embodiments are not limited thereto:

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[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic complex represented by Formula 401:

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In Formulae 401 and 402,

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

L₄₀₁may be a ligand represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, when xc1 is 2 or more, two or more L₄₀₁(s) may be identical to or different from each other,

L₄₀₂may be an organic ligand, and xc2 may be an integer from 0 to 4, wherein, when xc2 may be 2 or more, two or more L₄₀₂(s) may be identical to or different from each other,

X₄₀₁to X₄₀₄may each independently be nitrogen or carbon,

X₄₀₁and X₄₀₃may be linked to each other via a single bond or a double bond, and X₄₀₂and X₄₀₄may be linked to each other via a single bond or a double bond,

ring A₄₀₁and ring A₄₀₂may each independently be a C₅-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

X₄₀₅may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)-*′, *—C(Q₄₁₁)(Q₄₁₂)-*′, *—C(Q₄₁₁)=C(Q₄₁₂)-*′, *—C(Q₄₁₁)=*′, or *═C═*′, wherein Q₄₁₁and Q₄₁₂may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

X₄₀₆may be a single bond, O, or S,

R₄₀₁and R₄₀₂may each independently be selected from 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-C₂₀alkyl group, a substituted or unsubstituted C₁-C₂₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), wherein Q₄₀₁to Q₄₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a C₆-C₂₀aryl group, and a C₁-C₂₀heteroaryl group,

xc11 and xc12 may each independently be an integer from 0 to 3, and

* and *′ in Formula 402 each indicate a binding site to a M in Formula 401.

In an embodiment, ring A₄₀₁and ring A₄₀₂in Formula 402 may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, and a dibenzothiophene group.

In embodiments, in Formula 402, i) X₄₀₁may be nitrogen and X₄₀₂may be carbon, or ii) X₄₀₁and X₄₀₂may each be nitrogen at the same time.

In embodiments, R₄₀₁and R₄₀₂in Formula 402 may each independently be selected from:

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-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a phenyl group, a naphthyl group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, and a norbornenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group;

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

—Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), and —P(═O)(Q₄₀₁)(Q₄₀₂), and

Q₄₀₁to Q₄₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but embodiments are not limited thereto.

In embodiments, when xc1 in Formula 401 is 2 or more, two A₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked to each other via X₄₀₇, which is a linking group, two A₄₀₂(s) may optionally be linked to each other via X₄₀₈, which is a linking group (see Compounds PD1 to PD4 and PD7). X₄₀₇and X₄₀₈may each independently be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₃)-*′, *—C(Q₄₁₃)(Q₄₁₄)-*′, or *—C(Q₄₁₃)=C(Q₄₁₄)-*′ (where Q₄₁₃and Q₄₁₄may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but embodiments are not limited thereto.

L₄₀₂in Formula 401 may be a monovalent, divalent, or trivalent organic ligand. For example, L₄₀₂may be selected from halogen, diketone (for example, acetylacetonate), carboxylic acid (for example, picolinate), —C(═O), isonitrile, —CN, and phosphorus (for example, phosphine, or phosphite), but embodiments are not limited thereto.

In embodiments, the phosphorescent dopant may be selected from, for example, Compounds PD1 to PD25, but embodiments are not limited thereto:

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[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may include the condensed-cyclic compound represented by Formula 1. The condensed cyclic compound represented by Formula 1 may be a thermally active delayed fluorescence emitter.

The fluorescent dopant may further include an arylamine compound or a styrylamine compound.

The fluorescent dopant may include a compound represented by Formula 501:

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In Formula 501,

Ar₅₀₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

L₅₀₁to L₅₀₃may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xd1 to xd3 may each independently be an integer from 0 to 3,

R₅₀₁and R₅₀₂may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and

xd4 may be an integer from 1 to 6.

In an embodiment, Ar₅₀₁in Formula 501 may be selected from:

a naphthalene group, a heptalene 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, and an indenophenanthrene group, each substituted with at least one selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In embodiments, L₅₀₁to L₅₀₃in Formula 501 may each independently be selected from:

In embodiments, R₅₀₁and R₅₀₂in Formula 501 may each independently be selected from:

Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In embodiments, xd4 in Formula 501 may be 2, but embodiments are not limited thereto.

For example, the fluorescent dopant may be selected from Compounds FD1 to FD22:

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In embodiments, the fluorescent dopant may be selected from the following compounds, but embodiments are not limited thereto.

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[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including different materials, or iii) a multi-layered structure having layers including different materials.

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

For example, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein for each structure, constituting layers are sequentially stacked from an emission layer. However, embodiments of the structure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a hole blocking layer, an electron control layer, or an electron transport layer in the electron transport region) may include a metal-free compound containing at least one π electron-depleted nitrogen-containing ring.

The “π electron-depleted nitrogen-containing ring” indicates a C₁-C₆₀heterocyclic group having at least one *—N═*′ moiety as a ring-forming moiety.

For example, the “π electron-depleted nitrogen-containing ring” may be i) a 5-membered to 7-membered heteromonocyclic group having at least one *—N═*′ moiety, ii) a heteropolycyclic group in which two or more 5-membered to 7-membered heteromonocyclic groups each having at least one *—N═*′ moiety are condensed with each other, or iii) a heteropolycyclic group in which at least one of 5-membered to 7-membered heteromonocyclic groups, each having at least one *—N═*′ moiety, is condensed with at least one C₅-C₆₀carbocyclic group.

Examples of the π electron-deficient nitrogen-containing ring include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an indazole ring, a purine ring, a quinoline ring, an isoquinoline ring, a benzoquinoline ring, a phthalazine ring, a naphthyridine ring, a quinoxaline ring, a quinazoline ring, a cinnoline ring, a phenanthridine ring, an acridine ring, a phenanthroline ring, a phenazine ring, a benzimidazole ring, an isobenzothiazole ring, a benzoxazole ring, an isobenzoxazole ring, a triazole ring, a tetrazole ring, an oxadiazole ring, a triazine ring, a thiadiazole ring, an imidazopyridine ring, an imidazopyrimidine ring, and an azacarbazole ring, but are not limited thereto.

For example, the electron transport region may include a compound represented by Formula 601:

[Ar₆₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21 <Formula 601>

In Formula 601,

Ar₆₀₁may be a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group, and

xe21 may be an integer from 1 to 5.

In an embodiment, at least one of Ar₆₀₁(s) in the number of xe11 and R₆₀₁(s) in the number of xe21 may include the π electron-deficient nitrogen-containing ring.

In an embodiment, Ar₆₀₁in Formula 601 may be selected from:

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, a carbazole 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 pyrimidine group, a pyridazine 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

Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

When xe11 in Formula 601 is 2 or more, two or more Ar₆₀₁(s) may be linked to each other via a single bond.

In embodiments, Ar₆₀₁in Formula 601 may be an anthracene group.

In embodiments, the compound represented by Formula 601 may be represented by Formula 601-1:

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In Formula 601-1,

X₆₁₄may be N or C(R₆₁₄), X₆₁₅may be N or C(R₆₁₅), X₆₁₆may be N or C(R₆₁₆), and at least one of X₆₁₄to X₆16 may be N,

L₆11 to L₆₁₃may each independently be understood as described in connection with L₆₀₁,

xe611 to xe613 may each independently be understood as described in connection with xe1,

R₆₁₁to R₆₁₃may each independently be understood as described in connection with R₆₀₁, and

R₆₁₄to R₆₁₆may each independently be selected from 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, and a naphthyl group.

In an embodiment, L₆₀₁and L₆₁₁to L₆₁₃in Formulae 601 and 601-1 may each independently be selected from:

but embodiments are not limited thereto.

In embodiments, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.

In embodiments, R₆₀₁and R₆₁₁to R₆₁₃in Formulae 601 and 601-1 may each independently be selected from:

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁and Q₆₀₂are the same as described above.

The electron transport region may include at least one compound selected from Compounds ET1 to ET36, but embodiments are not limited thereto:

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In embodiments, the electron transport region may include at least one compound selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1, 10-phenanthroline (Bphen), Alq3, BAIq, 3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole (TAZ), and NTAZ:

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Thicknesses of the buffer layer, the hole blocking layer, and the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å. For example, the thickness of the buffer layer may be in a range of about 30 Å to about 300 Å. For example, the thickness of the hole blocking layer may be in a range of about 30 Å to about 300 Å. For example, the thickness of the electron control layer may be in a range of about 30 Å to about 300 Å. When the thicknesses of the buffer layer, the hole blocking layer, and the electron control layer are within these ranges, excellent hole blocking characteristics or excellent electron control characteristics may be obtained without a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å. For example, the thickness of the electron transport layer may be in a range of about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layer in the electron transport region) may further include a metal-containing material.

The metal-containing material may include at least one selected from alkali metal complex and alkaline earth-metal complex. The alkali metal complex may include a metal ion selected from a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, a hydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxy diphenylthiadiazole, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments are not limited thereto.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium quinolate, LiQ) or ET-D2:

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The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 190. The electron injection layer may directly contact the second electrode 190.

The electron injection layer may have i) a single-layered structure including a single layer including a single material, ii) a single-layered structure including a single layer including different materials, or iii) a multi-layered structure having layers including different materials.

The electron injection layer may include an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In an embodiment, the alkali metal may be Li, Na, or Cs. In embodiments, the alkali metal may be Li or Cs, but embodiments are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and the rare earth metal compound may be selected from oxides and halides (for example, fluorides, chlorides, bromides, or iodides) of the alkali metal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, such as Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In an embodiment, the alkali metal compound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, but embodiments are not limited thereto.

The alkaline earth-metal compound may be selected from alkaline earth-metal oxides, such as BaO, SrO, CaO, Ba_xSr_1-xO (where 0<x<1), or Ba_xCa_1-xO (where 0<x<1). In an embodiment, the alkaline earth-metal compound may be selected from BaO, SrO, and CaO, but embodiments are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In an embodiment, the rare earth metal compound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃, but embodiments are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rare earth metal complex may include an ion of alkali metal, alkaline earth-metal, and rare earth metal as described above, and a ligand coordinated with a metal ion of the alkali metal complex, the alkaline earth-metal complex, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments are not limited thereto.

The electron injection layer may consist of an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å. For example, the thickness of the electron injection layer may be in a range of about 3 Å to about 90 Å. When the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.

[Second Electrode 190]

The second electrode 190 is located on the organic layer 150 having such a structure. The second electrode 190 may be a cathode which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from a metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.

The second electrode 190 may include at least one selected from lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ITO, and IZO, but embodiments are not limited thereto. The second electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure or a multi-layered structure including two or more layers.

[Description of FIGS. 2 to 4]

An organic light-emitting device 20 of FIG. 2 includes a first capping layer 210, a first electrode 110, an organic layer 150, and a second electrode 190 which are sequentially stacked in this stated order, an organic light-emitting device 30 of FIG. 3 includes a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220 which are sequentially stacked in this stated order, and an organic light-emitting device 40 of FIG. 4 includes a first capping layer 210, a first electrode 110, an organic layer 150, a second electrode 190, and a second capping layer 220.

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150, and the second electrode 190 may each be understood as described in connection with FIG. 1.

In the organic layer 150 of each of the organic light-emitting devices 20 and 40, light generated in an emission layer may pass through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer 210 toward the outside, and in the organic layer 150 of each of the organic light-emitting devices 30 and 40, light generated in an emission layer may pass through the second electrode 190, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer 220 toward the outside.

The first capping layer 210 and the second capping layer 220 may increase external luminescent efficiency according to the principle of constructive interference.

The first capping layer 210 and the second capping layer 220 may each independently be an organic capping layer including an organic material, an inorganic capping layer including an inorganic material, or a composite capping layer including an organic material and an inorganic material.

At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from a carbocyclic compound, a heterocyclic compound, an amine-based compound, a porphyrine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, and an alkaline earth-based complex. The carbocyclic compound, the heterocyclic compound, and the amine-based compound may be optionally substituted with a substituent containing at least one element selected from O, N, S, Se, Si, F, Cl, Br, and I. In an embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include an amine-based compound.

In an embodiment, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include the compound represented by Formula 201 or the compound represented by Formula 202.

In embodiments, at least one selected from the first capping layer 210 and the second capping layer 220 may each independently include a compound selected from Compounds HT28 to HT33 and Compounds CP1 to CP5, but embodiments are not limited thereto:

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Hereinbefore, the organic light-emitting device according to an embodiment has been described in connection with FIGS. 1 to 4. However, embodiments are not limited thereto.

Layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region may be formed in a certain region by using suitable methods selected from vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser-printing, and laser-induced thermal imaging.

When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by vacuum deposition, the deposition may be performed at a deposition temperature of about 100° C. to about 500° C., a vacuum degree of about 10⁻⁸torr to about 10⁻³torr, and a deposition speed of about 0.01 Å/sec to about 100 Å/sec by taking into account a material to be included in a layer to be formed and the structure of a layer to be formed.

When layers constituting the hole transport region, an emission layer, and layers constituting the electron transport region are formed by spin coating, the spin coating may be performed at a coating speed of about 2,000 rpm to about 5,000 rpm and at a heat treatment temperature of about 80° C. to 200° C. by taking into account a material to be included in a layer to be formed and the structure of a layer to be formed.

Definitions of Substituents

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched aliphatic saturated hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an isoamyl group, and a hexyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

The term “C₂-C₆₀alkenyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₆₀alkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkenyl group.

The term “C₂-C₆₀alkynyl group” as used herein refers to a hydrocarbon group having at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₆₀alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C₂-C₆₀alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

The term “C₁-C₆₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group), and examples thereof include a methoxy group, an ethoxy group, and an isopropyloxy group.

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term “C₃-C₁₀cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent monocyclic group having at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof and no aromaticity, and examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include two or more rings, the two or more rings may be fused to each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the two or more rings may be condensed with each other.

The term “C₆-C₆₀aryloxy group” as used herein refers to —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein refers to —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) having two or more rings condensed with each other, only carbon atoms as ring-forming atoms, and no aromaticity in its entire molecular structure. A detailed example of the monovalent non-aromatic condensed polycyclic group is a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 1 to 60 carbon atoms) having two or more rings condensed to each other, at least one heteroatom selected from N, O, Si, P, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. An example of the monovalent non-aromatic condensed heteropolycyclic group is a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₆₀carbocyclic group” as used herein refers to a monocyclic or polycyclic group that includes only carbon as a ring-forming atom and consists of 5 to 60 carbon atoms. The C₅-C₆₀carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C₅-C₆₀carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. In embodiments, depending on the number of substituents connected to the C₅-C₆₀carbocyclic group, the C₅-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₁-C₆₀heterocyclic group” as used herein refers to a group having the same structure as the C₅-C₆₀carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms may be in a range of 1 to 60).

In the specification, at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from 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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and —P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be selected from 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-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

The term “Ph” as used herein refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “ter-Bu” or “Bu^t” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

The term “biphenyl group” as used herein refers to “a phenyl group substituted with a phenyl group”. In other words, the “biphenyl group” is a substituted phenyl group having a C₆-C₆₀aryl group as a substituent.

The term “terphenyl group” as used herein refers to “a phenyl group substituted with a biphenyl group”. In other words, the “terphenyl group” is a substituted phenyl group having, as a substituent, a C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group.

* and *′ as used herein, unless defined otherwise, each refer to a binding site to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organic light-emitting device according to embodiments will be described in detail with reference to Synthesis Examples and Examples. The wording “B was used instead of A” used in describing Synthesis Examples refers to that an identical molar equivalent of B was used in place of A.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 1
(Synthesis of Intermediate Compound 1-1)

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4,6-dibromoisophthalonitrile (8.11 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g, 1.2 mM), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 5.66 g of Intermediate Compound 1-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (Yield: 43%).

(Synthesis of Intermediate Compound 1-2)

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Intermediate Compound 1-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (5.66 g), aniline (20.3 mL, 223 mM), Na-t-butoxide (25.5 g, 265 mM), tri-t-butylphosphine (0.493 g, 1.2 mM), Pd₂(dba)₃(971 mg, 1.06 mM), and toluene (400 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 18 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.4 g of Intermediate Compound 1-2 (4-(diphenylamino)-6-(phenylamino)isophthalonitrile) (Yield: 60%).

(Synthesis of Intermediate Compound 1-3)

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Intermediate Compound 1-2 (4-(diphenylamino)-6-(phenylamino)isophthalonitrile) (3.4 g), 1,3-dibromobenzene (25.0 g, 106 mM), Na-t-butoxide (1.47 g, 15 mM), tri-t-butylphosphine (60.7 mg), Pd₂(dba)₃(0.140 g, 0.15 mM), and toluene (200 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 8 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.0 g of Intermediate Compound 1-3 (6,6′-(1,3-phenylenebis(phenylazanediyl))bis(4-(diphenylamino)isophthalonitrile)) (Yield: 87%).

(Synthesis of Compound 1)

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Intermediate Compound 1-3 (6,6′-(1,3-phenylenebis(phenylazanediyl))bis(4-(diphenylamino)isophthalonitrile)) (3.0 g) and o-DCB (400 mL) were added to a flask, and BBr₃(1.13 mL, 12 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 180° C. and the mixed solution was stirred for 20 hours. The reaction solution was subjected to sublimation purification at a temperature of 440° C., so as to obtain Compound 1 (1.17 g).

Synthesis Example 2: Synthesis of Compound 6
(Synthesis of Intermediate Compound 6-1-1)

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4-bromo-6-fluoroisophthalonitrile (5.5 g), 3-chlorophenol (3.00 g), Cs₂CO₃(10.0 g), and NMP (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 140° C. for 13 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 4.9 g of Intermediate Compound 6-1-1 (4-bromo-6-(3-chlorophenoxy)isophthalonitrile) (Yield of 89%).

(Synthesis of Intermediate Compound 6-1-2)

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Intermediate Compound 6-1-1 (4-bromo-6-(3-chlorophenoxy)isophthalonitrile) (4.9 g), aniline (20.3 mL, 223 mM), Na-t-butoxide (25.5 g, 265 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(971 mg, 1.06 mM), and toluene (400 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 18 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.4 g of Intermediate Compound 6-1-2 (4-(3-chlorophenoxy)-6-(phenylamino)isophthalonitrile) (Yield: 85%).

(Synthesis of Intermediate Compound 6-2-1)

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4,6-dibromoisophthalonitrile (8.11 g, 30 mM), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 5.66 g of Intermediate Compound 6-2-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (Yield: 43%).

(Synthesis of Intermediate Compound 6-2-2)

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Intermediate Compound 6-2-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (5.66 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g, 1.2 mM), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.8 g of Intermediate Compound 6-2-2 (4,6-bis(diphenylamino)isophthalonitrile) (Yield: 60%).

(Synthesis of Intermediate Compound 6-3)

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Intermediate Compound 6-1-2 (4-(3-chlorophenoxy)-6-(phenylamino)isophthalonitrile) (3.4 g), Intermediate Compound 6-2-2 (4,6-bis(diphenylamino)isophthalonitrile) (3.8 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 2.1 g of Intermediate Compound 6-3 (4-((3-((2,4-dicyano-5-(diphenylamino)phenyl)(phenyl)amino)phenyl)(phenyl)amino)-6-phenoxyisophthalonitrile). (Yield: 60%)

(Synthesis of Compound 6)

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Intermediate Compound 6-3 (4-((3-((2,4-dicyano-5-(diphenylamino)phenyl)(phenyl)amino)phenyl)(phenyl)amino)-6-phenoxyisophthalonitrile) (2.1 g) and o-DCB (400 mL) were added to a flask, and BBr₃(1.13 mL, 12 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 180° C. and the mixed solution was stirred for 20 hours. The reaction solution was subjected to sublimation purification at a temperature of 440° C., so as to obtain Compound 6 (50 mg).

Synthesis Example 3: Synthesis of Compound 9
(Synthesis of Intermediate Compound 9-1)

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1,3-dibromo-5-fluorobenzene (8.0 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 5.5 g of Intermediate Compound 9-1 (3-bromo-5-fluoro-N,N-diphenylaniline) (Yield: 43%)

(Synthesis of Intermediate Compound 9-2)

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Intermediate Compound 9-1 (3-bromo-5-fluoro-N,N-diphenylaniline) (5.5 g), aniline (20.3 mL, 223 mM), Na-t-butoxide (25.5 g, 265 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(971 mg, 1.06 mM), and toluene (400 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 18 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.2 g of Intermediate Compound 9-2 (5-fluoro-N1,N1,N3-triphenylbenzene-1,3-diamine) (Yield: 60%).

(Synthesis of Intermediate Compound 9-3)

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Intermediate Compound 9-2 (5-fluoro-N1,N1,N3-triphenylbenzene-1,3-diamine) (3.2 g), 1,3-dibromobenzene (25.0 g, 106 mM), Na-t-butoxide (1.47 g, 15 mM), tri-t-butylphosphine (60.7 mg), Pd₂(dba)₃(0.140 g, 0.15 mM), and toluene (200 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 8 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 2.7 g of Intermediate Compound 9-3 (N1,N1′-(1,3-phenylene)bis(5-fluoro-N1,N3,N3-triphenylbenzene-1,3-diamine)) (Yield: 87%).

(Synthesis of Compound 9)

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Intermediate Compound 9-3 (N1,N1′-(1,3-phenylene)bis(5-fluoro-N1,N3,N3-triphenylbenzene-1,3-diamine)) (2.7 g) and o-DCB (400 mL) were added to a flask, and BBr₃(1.13 mL, 12 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 180° C. and the mixed solution was stirred for 20 hours. The reaction solution was subjected to sublimation purification at a temperature of 440° C., so as to obtain Compound 9 (1.0 g).

Synthesis Example 4: Synthesis of Compound 12
(Synthesis of Intermediate Compound 12-1)

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4,6-difluoroisophthalonitrile (5.8 g), resorcinol (3.10 g, 29 mM), Cs₂CO₃(10.0 g), and NMP (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 140° C. for 13 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.4 g of Intermediate Compound 12-1 (6,6′-(1,3-phenylenebis(oxy))bis(4-fluoroisophthalonitrile)) (Yield: 60%).

(Synthesis of Intermediate Compound 12-2)

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Intermediate Compound 12-1 (6,6′-(1,3-phenylenebis(oxy))bis(4-fluoroisophthalonitrile)) (3.4 g), phenol (3.0 g), Cs₂CO₃(10.0 g), and NMP (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 140° C. for 13 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 2.3 g of Intermediate Compound 12-2 (6,6′-(1,3-phenylenebis(oxy))bis(4-phenoxyisophthaonitrile)) (Yield of 73%)

(Synthesis of Compound 12)

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Intermediate Compound 12-2 (6,6′-(1,3-phenylenebis(oxy))bis(4-phenoxyisophthalonitrile)) (2.3 g) and o-xylene (500 mL) were added to a flask, and BBr₃(0.832 mL, 8.8 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 150° C. and the mixed solution was stirred for 24 hours. N-diisopropylethylamine (5.60 mL, 33 mM) was added thereto, and the reaction solution was subjected to sublimation purification, so as to obtain Compound 12 (50 mg)

Synthesis Example 5: Synthesis of Compound 17
(Synthesis of Intermediate Compound 17-1)

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2,4-dibromobenzonitrile (8.0 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g, 1.2 mM), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 5.5 g of Intermediate Compound 17-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (Yield: 65%).

(Synthesis of Intermediate Compound 17-2)

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Intermediate Compound 17-1 (4-bromo-6-(diphenylamino)isophthalonitrile) (5.5 g), aniline (20.3 mL, 223 mM), Na-t-butoxide (25.5 g, 265 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(971 mg, 1.06 mM), and toluene (400 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 18 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.3 g of Intermediate Compound 17-2 (4-(diphenylamino)-2-(phenylamino)benzonitrile) (Yield: 60%).

(Synthesis of Intermediate Compound 17-3)

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Intermediate Compound 17-2 (4-(diphenylamino)-2-(phenylamino)benzonitrile) (3.3 g), 1,3-dibromobenzene (25.0 g, 106 mM), Na-t-butoxide (1.47 g, 15 mM), tri-t-butylphosphine (60.7 mg), Pd₂(dba)₃(0.140 g, 0.15 mM), and toluene (200 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 8 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 2.7 g of Intermediate Compound 17-3 (6,6′-(1,3-phenylenebis(phenylazanediyl))bis(4-(diphenylamino)isophthalonitrile)) (Yield: 67%)

(Synthesis of Compound 17)

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Intermediate Compound 17-3 (6,6′-(1,3-phenylenebis(phenylazanediyl))bis(4-(diphenylamino)isophthalonitrile)) (2.7 g) and o-DCB (400 mL) were added to a flask, and BBr₃(1.13 mL, 12 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 180° C. and the mixed solution was stirred for 20 hours. The reaction solution was subjected to sublimation purification at a temperature of 440° C., so as to obtain Compound 17 (1.2 g).

Synthesis Example 6: Synthesis of Compound 33

_(Synthesis of Intermediate Compound 33-1)

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1,5-dibromo-2,3-difluorobenzene (8.2 g), diphenylamine (10.1 g, 60 mM), Na-t-butoxide (8.60 g, 90 mM), tri-t-butylphosphine (0.493 g, 1.2 mM), Pd₂(dba)₃(550 mg, 0.6 mM), and toluene (300 mL) were added to a flask, and the mixed solution was stirred at a temperature of 80° C. for 15 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 5.5 g of Intermediate Compound 33-1 (3-bromo-4,5-difluoro-N,N-diphenylaniline) (Yield: 65%).

(Synthesis of Intermediate Compound 33-2)

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Intermediate Compound 33-1 (3-bromo-4,5-difluoro-N,N-diphenylaniline) (5.5 g), aniline (20.3 mL, 223 mM), Na-t-butoxide (25.5 g, 265 mM), tri-t-butylphosphine (0.493 g), Pd₂(dba)₃(971 mg, 1.06 mM), and toluene (400 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 18 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 3.3 g of Intermediate Compound 33-2 (4,5-difluoro-N1,N1,N3-triphenylbenzene-1,3-diamine) (Yield: 63%).

(Synthesis of Intermediate Compound 33-3)

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Intermediate Compound 33-2 (4,5-difluoro-N1,N1,N3-triphenylbenzene-1,3-diamine) (3.3 g), 1,3-dibromobenzene (25.0 g, 106 mM), Na-t-butoxide (1.47 g, 15 mM), tri-t-butylphosphine (60.7 mg), Pd₂(dba)₃(0.140 g, 0.15 mM), and toluene (200 mL) were added to a flask, and the mixed solution was stirred at a temperature of 110° C. for 8 hours. The reaction solution was cooled to room temperature, and subjected to column separation, so as to obtain 2.8 g of Intermediate Compound 33-3 (N3,N3′-(1,3-phenylene)bis(4,5-difluoro-N1,N1,N3-triphenylbenzene-1,3-diamine)) (Yield: 88%).

(Synthesis of Compound 33)

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Intermediate Compound 33-3 (N3,N3′-(1,3-phenylene)bis(4,5-difluoro-N1,N1,N3-triphenylbenzene-1,3-diamine)) (2.8 g) and o-DCB (400 mL) were added to a flask, and BBr₃(1.13 mL, 12 mM) was added thereto at room temperature. Afterwards, the reaction temperature was raised up to 180° C. and the mixed solution was stirred for 20 hours. The reaction solution was subjected to sublimation purification at a temperature of 440° C., so as to obtain Compound 33 (0.9 g).

¹H NMR and MS/FAB of the compounds synthesized according to Synthesis Examples 1 to 6 are shown in Table 1 below.

Even compounds other than the compounds shown in Table 1 may be easily recognized by those skilled in the art by referring to the above synthesis routes and source materials.

TABLE 1

MS/FAB

Compound

¹H NMR (CDCl₃, 400 MHz)
found
calc.

1
δ = 6.83 (s, 1H), 7.00 (d, 4H), 7.08 (t, 8H),
862
862

7.18-24 (m, 12H), 7.25 (s, 1H), 7.29 (d, 2H),

7.43 (t, 2H), 7.71 (d, 2H)

6
δ = 6.83 (s, 1H), 7.00 (d, 4H), 7.01 (s, 1H),
787
787

7.07 (s, 1H), 7.08 (m, 6H), 7.18-24 (m, 7H),

7.25 (s, 1H), 7.29 (s, 1H), 7.35 (s, 1H), 7.43

(t, 2H), 7.71 (d, 2H)

9
δ = 6.83 (s, 1H), 6.94 (d, 4H), 7.00 (d, 4H),
798
798

7.01 (d, 2H), 7.08 (t, 8H), 7.18-24 (m, 10H),

7.25 (s, 1H), 7.29 (d, 2H), 7.71 (d, 2H)

12
δ = 6.65 (s, 1H), 7.00 (d, 2H), 7.07 (d, 2H),
562
562

7.25 (s, 1H), 7.35 (d, 2H), 7.71 (d, 2H)

17
δ = 6.83 (s, 1H), 7.00 (d, 4H), 7.01 (d, 2H),
812
812

7.02 (d, 2H), 7.08 (t, 8H), 7.18-24 (m, 10H),

7.25 (s, 1H), 7.29 (d, 2H), 7.52 (d, 2H), 7.71

(d, 2H)

33
δ = 6.83 (s, 1H), 6.92 (d, 2H), 7.00 (d, 4H),
834
834

7.01 (d, 2H), 7.08 (t, 8H), 7.18-24 (m, 10H),

7.25 (s, 1H), 7.29 (d, 2H), 7.71 (d, 2H)

Evaluation Examples
Evaluation Example 1: Evaluation of Bond Dissociation Energy of Compound

Regarding the compounds synthesized according to Synthesis Examples 1 to 8 and Compounds A to F, the weakest neutral/anion/cation bond dissociation energy was calculated by simulation according to the density functional theory (DFT) based on B3LYP/6-311 G** using a Gaussian 09 program.

TABLE 2

Minimum
Minimum
Minimum

neutral bond
anion bond
cation bond

dissociation
dissociation
dissociation

No.
energy
energy
energy

1
5.58
3.51
3.71

6
5.57
3.69
3.55

9
5.46
4.22
5.71

12
5.54
3.73
3.51

17
5.69
3.13
3.83

33
5.35
4.27
5.54

Compound A
3.22
2.29
3.47

Compound B
3.29
2.45
4.03

Compound C
N/A (no single
N/A
N/A

bond)

Compound D
3.11
1.32
3.28

Compound E
4.64
4.07
5.17

Compound F
3.23
2.16
3.74

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Referring to Table 2, the compounds according to an embodiment had the minimum bond dissociation energy levels higher than those of comparative Compounds A, B, and D to F, so that the compounds according to an embodiment were able to have strong structures and advantageous properties for long lifespan compared to the comparative compounds. In the case of the comparative Compound C, the compound did not include a single bond, so that the minimum bond dissociation energy thereof was not able to measure.

Evaluation Example 2: kRISC Evaluation of Compound

Regarding the compounds synthesized according to Synthesis Examples 1 to 8 and Compounds A to F, the kRISC values were calculated by simulation according to an ADF program using the following equation, the emission wavelengths were calculated by using a Gaussian 09 program, and the molecular weights were calculated by using a Materials Studio program, and the results are shown in Table 3 below.

$< Equation >$

$k_{RISC} = \frac{2 π}{\hat{h}} \frac{1}{\sqrt{4 π λ k_{s} T}} \exp [\frac{{(Δ E_{ST} + \overline{λ})}^{2}}{4 \hat{λ} k_{s} T}] {\langle (S_{1} \langle {\hat{H}}_{S D T} \rangle T_{s}) \rangle}^{2}$

TABLE 3

Emmission

wavelength
Molecular weight

No.
kRISC
(λmax, nm)
(MW)

1
1.24E+08
462
878.36

6
3.35E+07
460
787.46

9
3.94E+06
454
764.24

12
5.53E+06
448
562.11

17
1.92E+07
463
802.30

33
6.33E+06
466
802.23

Compound A
4.80E+05
459
1021.84

Compound B
2.25E+04
450
796.5

Compound C
2.39E+05
447
462.07

Compound D
9.90E+04
470
762.53

Compound E
4.71E+02
454
570.47

Compound F
1.91E+06
471
1096.95

Referring to Table 3, the compounds according to an embodiment had higher kRISC values than those of the comparative compounds, so that the compounds according to an embodiment had improved TADF characteristics, and based on the low molecular weights, the compounds according to an embodiment were found to be very suitable to implement an emission layer having a deep blue emission wavelength band.

Example 1

As an anode, a glass substrate with 15 Ωcm²(1,200 Å) ITO thereon, which was manufactured by Corning Inc., was cut to a size of 50 mm×50 mm×0.5 mm, and the glass substrate was sonicated by using isopropyl alcohol and pure water for 15 minutes each, and ultraviolet (UV) light was irradiated for 30 minutes thereto and ozone was exposed thereto for cleaning. The resultant glass substrate was loaded onto a vacuum deposition apparatus.

m-MTDATA was vacuum-deposited on the glass substrate to form a hole injection layer having a thickness of 600 Å, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 100 Å.

Subsequently, on the hole transport layer, BAIq and Compound 1 were co-deposited as a host and a dopant, respectively, at a weight ratio of 97:3 to form an emission layer having a thickness of 300 Å.

BAIq was deposited on the emission layer to form a hole blocking layer having a thickness of 100 Å, and Alq₃was deposited on the hole blocking layer to form an electron transport layer having a thickness of 200 Å.

LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and A1 was deposited on the electron injection layer to form a cathode having a thickness of 2,000 Å, thereby manufacturing an organic light-emitting device.

Examples 2 and 5 and Comparative Examples 1 to 6

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that the compounds of Table 4 were used to form emission layers.

Evaluation Example 3: Evaluation of Device Characteristics

Regarding the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Examples 1 to 6, efficiency (cd/A) at current density of 10 mA/cm², emission wavelength, and a period of time that was taken until the initial luminance at current density of 10 mA/cm²was reduced by 95% (half-life) are measured, and the results are shown in Table 4 below.

TABLE 4

Emission

Luminescent
Efficiency
wavelength
LT95

material
(cd/A)
(λmax, nm)
(hr)

Example 1
Compound 1
368
462
293

Example 2
Compound 6
320
460
282

Example 3
Compound 9
295
454
234

Example 4
Compound 12
301
448
270

Example 5
Compound 17
307
463
256

Example 6
Compound 33
299
466
241

Comparative
Compound A
99
459
168

Example 1

Comparative
Compound B
81
450
72

Example 2

Comparative
Compound C
89
447
2

Example 3

Comparative
Compound D
84
470
99

Example 4

Comparative
Compound E
80
454
1

Example 5

Comparative
Compound F
155
471
188

Example 6

Referring to Table 4, it was confirmed that the organic light-emitting devices of Examples 1 to 6 including the compounds according to an embodiment had significantly improved efficiency and lifespan characteristics, compared to those of the organic light-emitting devices of Comparative Examples 1 to 6.

According to the embodiments, an organic light-emitting device including a condensed cyclic compound may have high efficiency and a long lifespan.

Although the disclosure has been described with reference to the Synthesis Examples and Examples, these examples are provided for illustrative purpose only, and one of ordinary skill in the art may understand that these examples may have various modifications and other examples equivalent thereto. Accordingly, the scope of the disclosure should be determined by the technical concept of the claims.

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 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.

CONDENSED-CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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