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

CROSS-REFERENCE TO RELATED APPLICATIONS

This application claims the benefit of Korean Patent Application Nos. 10-2015-0182792 filed on Dec. 21, 2015, and 10-2016-0046499 filed on Apr. 15, 2016 in the Korean Intellectual Property Office, the disclosure of which are incorporated herein in their entirety by reference.

BACKGROUND
1. Field

One or more embodiments relate to a condensed cyclic compound and an organic light-emitting device including the same.

SUMMARY

Organic light-emitting devices are self-emission devices that offer advantages such as wide viewing angles, high contrast ratios, short response times, and excellent luminance, driving voltage, and response speed characteristics, and produce full-color images.

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. Then, the excitons are transitioned from an excited state to a ground state, thereby generating light.

SUMMARY

One or more embodiments include a novel condensed cyclic compound and an organic light-emitting device including the same.

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

According to one or more embodiments, a condensed cyclic compound is represented by Formula 1:

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In Formula 1,

ring A may be selected from a C₅-C₃₀carbocyclic ring and a C₂-C₃₀heterocyclic ring,

X₁may be C(R₁) or N, X₂may be C(R₂) or N, at least one of X₁and X₂may be N,

R₁to R₁₁may each independently be a group represented by one of Formulae 2-1 to 2-5 group, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a hydrazino group, a hydrazono group, substituted or unsubstituted C₁-C₆₀alkyl group, substituted or unsubstituted C₂-C₆₀alkenyl group, substituted or unsubstituted C₂-C₆₀alkynyl group, substituted or unsubstituted C₁-C₆₀alkoxy group, substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂):

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L₁to L₁₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

a1 to a11 may each independently be 0, 1, 2, 3, 4, or 5,

Ar₁to Ar₇may be a substituted or unsubstituted C₁-C₆₀alkyl group, substituted or unsubstituted C₂-C₆₀alkenyl group, substituted or unsubstituted C₂-C₆₀alkynyl group, substituted or unsubstituted C₁-C₆₀alkoxy group, substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group,

b1 to b4 may each independently be 1, 2, or 3,

c3 may be 0, 1, 2, 3, 4, 5, or 6,

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

deuterium (-D), —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, 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),

wherein Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃ custom character each independently 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, and

* indicates a binding site to a neighboring atom.

According to another aspect, an organic light-emitting device includes a first electrode; a second electrode facing the first electrode; and an organic layer that is disposed between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes at least one of condensed cyclic compounds represented by Formula 1.

BRIEF DESCRIPTION OF THE DRAWINGS

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

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

FIG. 2 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;

FIG. 3 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment; and

FIG. 4 is a schematic cross-sectional view of an organic light-emitting device according to an embodiment;

DETAILED DESCRIPTION

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

A condensed cyclic compound according to an embodiment of the present disclosure is represented by Formula 1:

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Ring A in Formula 1 may be selected from a C₅-C₃₀carbocyclic ring and a C₂-C₃₀heterocyclic ring. For example, ring A may be selected from a benzene group, a pyridine group, a pyridazine group, a pyrimidine group, a pyrazine group, a naphthalene group, a quinoline group, an isoquinoline group, a cinnoline group, a quinazoline group, a quinoxaline group, a naphthyridine group, an anthracene group, a phenanthrene group, a benzoquinoline group, a phenanthridine group, an acridine group, a phenanthroline group, and a phenazine group. In one embodiment, ring A may be selected from a benzene group, a pyridine group, a naphthalene group, a quinoline group, and an isoquinoline group, but embodiments of the present disclosure are not limited thereto.

In Formula 1, X₁may be C(R₁) or N, X₂may be C(R₂) or N, and at least one of X₁and X₂may be N.

R₁to R₁₁in Formula 1 may each independently be selected from the group represented by one of Formulae 2-1 to 2-5, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a hydrazino group, a hydrazono group, substituted or unsubstituted C₁-C₆₀alkyl group, substituted or unsubstituted C₂-C₆₀alkenyl group, substituted or unsubstituted C₂-C₆₀alkynyl group, substituted or unsubstituted C₁-C₆₀alkoxy group, substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), wherein Q₁to Q₃may 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:

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* in Formulae 2-1 to 2-5 indicates a binding site to a neighboring atom.

L₁to L₁₁in Formulae 2-1 to 2-5 may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group. For example, L₁to L₁₁may 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 pyrrolylene group, a thiophenylene group, a furanylene group, an imidazolylene group, a pyrazolylene group, a thiazolylene group, an isothiazolylene group, an oxazolylene group, an isoxazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, an isoindolylene group, an indolylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a carbazolylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzimidazolylene group, a benzofuranylene group, a benzothiophenylene group, an isobenzothiazolylene group, a benzoxazolylene group, an isobenzoxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, a triazinylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a benzocarbazolylene group, a dibenzosilolylene group, a dibenzocarbazolylene group, a thiadiazolylene group, an imidazopyridinylene group, and an imidazopyrimidinylene 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 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 pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, and a carbazolyl group.

In one embodiment, L₁to L₁₁may each independently be selected from groups represented by Formulae 3-1 to 3-25:

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In Formulae 3-1 to 3-25,

Y₁may be O, S, C(Z₅)(Z₆), N(Z₇), or Si(Z₅)(Z₉),

Z₁to Z₉may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein 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,

d3 may be an integer from 1 to 3,

d4 may be an integer from 1 to 4,

d6 may be an integer from 1 to 6,

d8 may be an integer from 1 to 8, and

* and *′ each indicate a binding site to a neighboring atom. For example, L₁to L₁₁may each independently be selected from groups represented by Formulae 4-1 to 4-19, but embodiments of the present disclosure are not limited thereto:

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* and *′ in Formulae 4-1 to 4-19 each indicate a binding site to a neighboring atom.

a1 to a11 in Formulae 2-1 to 2-5 may each independently be O, 1, 2, 3, 4, or 5.

a1 indicates the number of L₁(s), wherein, when a1 is 0, *-(L₁)_a1-*′ indicates a single bond, and when a1 is two or more, two or more L₁(s) may be identical to or different from each other. a2 to a11 may be understood by referring to the description of a1 and the structures of Formulae 2-1 to 2-5. For example, a1 to a10 may each independently be 0, 1, 2, or 3, but embodiments of the present disclosure are not limited thereto.

Ar₁to Ar₇in Formulae 2-1 to 2-5 may be selected from a substituted or unsubstituted C₁-C₆₀alkyl group, substituted or unsubstituted C₂-C₆₀alkenyl group, substituted or unsubstituted C₂-C₆₀alkynyl group, substituted or unsubstituted C₁-C₆₀alkoxy group, substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. For example, Ar₁to Ar₇may 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 pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a dibenzosilolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzonaphthofuranyl group, a dinaphthofuranyl group, a benzonaphthothiophenyl group, a dinaphthothiophenyl group, a benzonaphthosilolyl group, and a dinaphthosilolyl 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 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 pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzosilolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a thiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, a benzonaphthofuranyl group, a dinaphthofuranyl group, a benzonaphthothiophenyl group, a dinaphthothiophenyl group, a benzonaphthosilolyl group, a dinaphthosilolyl group, —Si(Q₃₁)(₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

In one embodiment, Ar₁to Ar₇may each independently be selected from groups represented by Formulae 5-1 to 5-25:

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In Formulae 5-1 to 5-25,

Y₃₁may be O, S, C(Z₃₃)(Z₃₄), N(Z₃₅), or Si(Z₃₆)(Z₃₇),

Z₃₁to Z₃₇may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, and —Si(Q₃₁)(Q₃₂)(Q₃₃), wherein 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,

e3 may be an integer from 1 to 3,

e4 may be an integer from 1 to 4,

e5 may be an integer from 1 to 5,

e6 may be an integer from 1 to 6,

e7 may be an integer from 1 to 7,

e9 may be an integer from 1 to 9, and

* indicates a binding site to a neighboring atom. For example, Ar₁to Ar₇may each independently be selected from groups represented by Formulae 6-1 to 6-18, but embodiments of the present disclosure are not limited thereto:

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* in Formulae 6-1 to 6-18 indicates a binding site to a neighboring atom.

b1 to b4 in Formulae 2-1 to 2-4 may each independently be 1, 2, or 3. For example, b1 to b4 may be 1, but embodiments of the present disclosure are not limited thereto.

In one embodiment, R₁to R₁₁may 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 triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, and an imidazopyrimidinyl 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-C₁₀alkyl group, a C₁-C₁₀alkoxy 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 triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂); and

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁) and —P(═O)(Q₁)(Q₂),

wherein Q₁to Q₃and Q₃₁to Q₃₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy 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 triphenylenyl group, a pyrenyl group, a chrysenyl group, and a carbazolyl group.

In one embodiment, R₁to R₁₁may each independently be selected from:

the group represented by one of Formulae 2-1 to 2-5, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

wherein 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 of the present disclosure are not limited thereto.

c3 in Formula 1 may be 0, 1, 2, 3, 4, 5, or 6. c3 indicates the number of R₃(s), wherein, when c3 is two or more, two or more R₃(s) may be identical to or different from each other. For example, c3 may be 0, 1, 2, or 3, but embodiments of the present disclosure are not limited thereto.

In one embodiment, in Formula 1, X₁may be N, X₂may be C(R₂), R₂may be selected from groups represented by Formulae 2-1 to 2-5, and R₃to R₁₁may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, in Formula 1, X₁may be C(R₁), X₂may be N, R₁may be selected from groups represented by Formulae 2-1 to 2-5, and R₃to R₁₁may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, in Formula 1, R₃may be selected from groups represented by Formulae 2-1 to 2-5, R₁, R₂and R₄to R₁₁may each independently be selected from the group represented by Formula 2-5, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, Formula 1 may be represented by one of Formulae 1A to 1S:

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In Formulae 1A to 1S,

R₃₁to R₃₆may be the same as described in connection with R₃, and

X₁, X₂, and R₃to R₁₁are the same as described above.

In one embodiment, in Formulae 1A to 1S, X₁may be N, X₂may be C(R₂), and R₂may be selected from groups represented by Formulae 2-1 to 2-5. For example, in Formulae 1A to 1S, X₁may be N, X₂may be C(R₂), R₂may be selected from groups represented by Formulae 2-1 to 2-5, R₃₁to R₃₆and R₄to R₁₁may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, in Formulae 1A to 1S, X₁may be C(R₁), X₂may be N, and R₁may be selected from groups represented by Formulae 2-1 to 2-5. For example, in Formulae 1A to 1S, X₁may be C(R₁), X₂may be N, R₁may be selected from groups represented by Formulae 2-1 to 2-5, and R₃₁to R₃₆and R₄to R₁₁may 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, in Formulae 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X₁may be N, X₂may be C(R₂), and R₃₂may be selected from groups represented by Formulae 2-1 to 2-5. For example, in Formulae 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X₁may be N, X₂may be C(R₂), R₃₂may be selected from groups represented by Formulae 2-1 to 2-5, and R₂, R₃₁, R₃₃to R₃₆and R₄to R₁₁may each independently be selected from the group represented by Formula 2-5, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

In one embodiment, in Formulae 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X₁may be C(R₁), X₂may be N, and R₃₂may be selected from groups represented by Formulae 2-1 to 2-5. For example, in Formulae 1A, 1B, 1D to 1G, 1I to 1N, and 1P to 1S, X₁may be C(R₁), X₂may be N, R₃₂may be selected from groups represented by Formulae 2-1 to 2-5, R₁, R₃₁, R₃₃to R₃₆, and R₄to R₁₁may each independently be selected from the group represented by Formula 2-5, 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, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a carbazolyl group, a benzocarbazolyl group, and a dibenzocarbazolyl group.

The condensed cyclic compound represented by Formula 1 may be one of Compounds 1 to 192, but embodiments of the present disclosure are not limited thereto:

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The condensed cyclic compound represented by Formula 1 has excellent charge transport characteristics and thermal stability. Accordingly, an organic light-emitting device including the condensed cyclic compound represented by Formula 1 may have a low driving voltage, high efficiency, high luminance, and a long lifespan.

A method of synthesizing the condensed cyclic compound represented by Formula 1 may be understood by referring to the following examples.

At least one of the condensed cyclic compounds represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. In one or more embodiments, the condensed cyclic compound may be included in an electron transport region.

The expression “(an organic layer) includes at least one of the condensed cyclic compounds” used herein may include a case in which “(an organic layer) includes identical condensed cyclic compounds represented by Formula 1” and a case in which “(an organic layer) includes two or more different condensed cyclic compounds represented by Formula 1.”

For example, the organic layer may include, as the condensed cyclic compound, only Compound 1. In this regard, Compound 1 may exist only in an electron transport layer of the organic light-emitting device. In one or more embodiments, the organic layer may include, as the condensed cyclic compound, Compound 1 and Compound 2. In one or more embodiments, Compound 1 and Compound 2 may both exist in an identical layer (for example, Compound 1 and Compound 2 may both exist in an electron transport layer), or may exist in different layers (for example, Compound 1 may exist in an electron transport layer and Compound 2 may exist in an electron injection layer).

The organic layer includes i) a hole transport region that is disposed between the first electrode (anode) and the emission layer and includes at least one of a hole injection layer, a hole transport layer, an emission auxiliary layer, and an electron blocking layer, and ii) an electron transport region that is disposed between the emission layer and the second electrode (cathode) and includes at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer. The electron transport region may include at least one condensed cyclic compound represented by Formula 1. For example, the electron transport region of the organic light-emitting device may include the electron transport layer, wherein the electron transport layer may include at least one of the condensed cyclic compound represented by Formula 1. For example, the electron transport region of the organic light-emitting device may include an electron injection layer, and the electron injection layer may include at least one of the organometallic compounds represented by Formula 1.

The organic light-emitting device may further include at least one selected from a first capping layer disposed in a pathway along which light generated in an emission layer travels toward outside through the first electrode and a second capping layer disposed in a pathway along which light generated in an emission layer travels toward outside through the second electrode, and the at least one selected from the first capping layer and the second capping layer may include at least one of the condensed cyclic compounds represented by Formula 1.

For example, the organic light-emitting device may have i) a stack structure including a first electrode, an organic layer, a second electrode, and a second capping layer which are sequentially stacked in this stated order, ii) a stack structure including a first capping layer, a first electrode, an organic layer, and a second electrode which are sequentially stacked in this stated order, or iii) a stack structure including a first capping layer, a first electrode, an organic layer, a second electrode, and a second capping layer which are sequentially stacked in this stated order, and at least one selected from the first capping layer and the second capping layer may include the condensed cyclic compound.

The term “organic layer” used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the 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 the present embodiment and a method of manufacturing the same will be described in connection with FIG. 1.

[First Electrode 110]

In FIG. 1, a substrate may be additionally 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-reflective electrode, or a transmissive electrode. When the first electrode 110 is a transmissible electrode, a material for forming a first electrode may be selected from indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinations thereof, but embodiments of the present disclosure are not limited thereto. In one or more embodiments, when the first electrode 110 is a semi-transmissible electrode or a reflectable electrode, a material for forming a first electrode 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 of the present disclosure 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 disposed 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 a plurality of layers including different materials.

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

For example, the hole transport region may have a single-layered structure including a single layer including a plurality of 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, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, 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, substituted or unsubstituted C₂-C₂₀alkenylene group, substituted or unsubstituted C₃-C₁₀cycloalkylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, 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,

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, 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 via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group, and R₂₀₃and R₂₀₄may optionally be linked via a single bond, a dimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁to L₂₀₅may each independently be selected from:

wherein 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 one or more embodiments, xa1 to xa4 may each independently be 0, 1, or 2.

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

In one or more 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

wherein Q₃₁to Q₃₃may be the same as described above.

In one or more embodiments, at least one of 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 of the present disclosure are not limited thereto.

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

In one or more embodiments, at least one of 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 of the present disclosure are not limited thereto.

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

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For example, the compound represented by Formula 201 may be represented by Formula 201A(1), but embodiments of the present disclosure are not limited thereto:

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

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

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

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

L₂₀₁to L₂₀₃, xa1 to xa3, xa5, and R₂₀₂to R₂₀₄may be the same as described above,

R₂₁₁and R₂₁₂may be the same as described in connection with R₂₀₃,

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 HT39, but embodiments of the present disclosure 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, 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, a thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, and a thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example about 100 Å to about 1,500 Å. When the thickness of each of the hole transport region, the hole injection layer, and the hole transport layer is within these ranges, satisfactory hole transport 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 each include the materials as described above.

[p-Dopant]

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

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

In one embodiment, a lowest unoccupied molecular orbital (LUMO) 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 one 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);

metal oxide, such as tungsten oxide and molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221, but embodiments of the present disclosure 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, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and at least one of 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 one or more 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 one or more embodiments, the emission layer may include two or more materials selected from a red-light emission material, a green-light emission material, and a blue-light emission 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, in general, in a range of about 0.01 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

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

[Host in Emission Layer]

The host may include a compound represented by Formula 301.

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

In Formula 301,

Ar₃₀₁may be selected from 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, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, 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, wherein

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 of the present disclosure are not limited thereto.

In one 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),

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

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

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In Formulae 301-1 to 301-2,

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

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 Q₃₃may be the same as described above,

L₃₀₂to L₃₀₄may each independently be the same as described in connection with L₃₀₁.

Xb2 to xb4 may each independently be the same as described in connection with xb1, and

R₃₀₂to R₃₀₄may each independently be the same 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 aza carbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may be the same as described above.

In one 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 aza carbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

wherein Q₃₁to Q₃₃may be the same as described above.

In one or more 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 Compounds H1 to H55, but is not limited thereto:

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

In one or more embodiments, 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 selected from ligands represented by Formula 402, and xc1 may be 1, 2, or 3, wherein, when xc1 is two 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 is two 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 via a single bond or a double bond, and X₄₀₂and X₄₀₄may be linked via a single bond or a double bond,

A₄₀₁and A₄₀₂may each independently be selected from 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(Q₄₁₁)=*, Q₄₁₁and Q₄₁₂may be hydrogen, deuterium, 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, substituted or unsubstituted C₁-C₂₀alkyl group, substituted or unsubstituted C₁-C₂₀alkoxy group, substituted or unsubstituted C₃-C₁₀cycloalkyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, 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 10,

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

In one embodiment, A₄₀₁and 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 one or more embodiments, in Formula 402, i) X₄₀₁may be nitrogen, and X₄₀₂may be carbon, or ii) X₄₀₁and X₄₀₂may all be nitrogen.

In one or more 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),

wherein 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 of the present disclosure are not limited thereto.

In one or more embodiments, when xc1 in Formula 401 is two or more, two A₄₀₁(s) in two or more L₄₀₁(s) may optionally be linked via X₄₀₇, which is a linking group, or two A₄₀₂(S) in two or more L₄₀₁(s) may optionally be linked 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)-*′ (herein, Q₄₁₃and Q₄₁₄may each independently be selected from hydrogen, deuterium, C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but embodiments of the present disclosure 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 of the present disclosure are not limited thereto.

In one or more embodiments, the phosphorescent dopant may be selected from, for example, Compounds PD1 to PD25, but embodiments of the present disclosure are not limited thereto:

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[Fluorescent Dopant in Emission Layer]

The fluorescent dopant may 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, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, 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, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, 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 one 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 one or more embodiments, L₅₀to L₅₀₃in Formula 501 may each independently be selected from:

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

wherein Q₃₁to Q₃₃may 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 one or more embodiments, xd4 in Formula 501 may be two, but embodiments of the present disclosure are not limited thereto.

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

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In one embodiment, the fluorescent dopant may be selected from the following compounds, but embodiments of the present disclosure 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 a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and an electron injection layer, but embodiments of the present disclosure 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.

For example, 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 condensed cyclic compound represented by Formula 1.

In one embodiment, 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 heteropoly cyclic 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 heteropoly cyclic 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-depleted nitrogen-containing ring include an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a 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, thiadiazol group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group, but are not limited thereto.

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

[Ar₆₀₁]_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, substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, substituted or unsubstituted C₃-C₁₀cycloalkenylene group, substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, substituted or unsubstituted C₆-C₆₀arylene group, substituted or unsubstituted C₁-C₆₀heteroarylene group, 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, substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, substituted or unsubstituted C₃-C₁₀cycloalkenyl group, substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, substituted or unsubstituted C₆-C₆₀aryl group, substituted or unsubstituted C₆-C₆₀aryloxy group, substituted or unsubstituted C₆-C₆₀arylthio group, substituted or unsubstituted C₁-C₆₀heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, 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), wherein 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 one embodiment, at least one selected from Ar₆₀₁in the number of xe11 and R₆₀₁in the number of xe21 may include the π electron-depleted nitrogen-containing ring described above.

In one embodiment, ring 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, naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, phenanthroline group, phenazine group, a benzimidazole group, an iso-benzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazol group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

wherein 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 two or more, two or more Ar₆₀₁(S) may be linked via a single bond.

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

In one or more 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), at least one of X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may each independently be the same as described in connection with L₆₀₁,

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

R₆₁₁to R₆₁₃may each independently be the same 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 one embodiment, L₆₀₁and L₆₁₁to L₆₁₃in Formulae 601 and 601-1 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, and an azacarbazolyl group, but embodiments of the present disclosure are not limited thereto.

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

In one or more embodiments, R₆₀₁and R₆₁₁to R₆₁₃in Formulae 601 and 601-1 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, and an azacarbazolyl group; and

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂),

wherein Q₆₀₁and Q₆₀₂are the same as described above.

The electron transport region may include at least one compound represented by Compounds ET1 to ET36, but embodiments of the present disclosure are not limited thereto:

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

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

A thickness of the electron transport layer may be from about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer is within the ranges described above, excellent electron transport characteristics may be obtained 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, in addition to the materials described above, 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 an 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, an 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 phenylan oxazole, a hydroxy phenylthiazole, a hydroxy diphenylan oxadiazole, a hydroxy diphenylthiadiazol, a hydroxy phenylpyridine, a hydroxy phenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, a phenanthroline, and a cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

In one embodiment, 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 a plurality of layers including different materials.

The electron injection layer may include alkali metal, alkaline earth metal, 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 one embodiment, the alkali metal may be Li, Na, or Cs. In one or more embodiments, the alkali metal may be Li or Cs, but embodiments of the present disclosure 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 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, KI, or RbI. In one embodiment, the alkali metal compound may be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, but embodiments of the present disclosure are not limited thereto.

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

The rare-earth metal compound may be selected from YbF₃, ScF₃, ScO₃, Y₂O₃, Ce₂O₃, GdF₃, and TbF₃In one embodiment, the rare-earth metal compound may be selected from YbF₃, ScF₃, TbF₃, YbI₃, ScI₃, and TbI₃, but embodiments of the present disclosure 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, and the rare-earth metal complex may each independently be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenylan oxazole, hydroxy phenylthiazole, hydroxy diphenylan oxadiazole, hydroxy diphenylthiadiazol, hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxy phenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene, but embodiments of the present disclosure are not limited thereto.

The electron injection layer may consist of alkali metal, alkaline earth metal, 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 one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, alkali metal, alkaline earth metal, rare-earth metal, alkali metal compound, alkaline earth-metal compound, rare-earth metal compound, alkali metal complex, alkaline earth-metal complex, rare-earth metal complex, or any combinations 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, about 3 Å to about 90 Å. If the thickness of the electron injection layer is within the ranges described above, excellent electron injection characteristics may be obtained without a substantial increase in driving voltage.

[Second Electrode 190]

The second electrode 190 may be disposed on the organic layer 150 having such a structure. The second electrode 190 may be a cathode that is an electron injection electrode, and in this regard, as a metal for forming the second electrode 190, metal, alloy, an electrically conductive compound, and a combination thereof, each having a low work function, may be used.

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 of the present disclosure are not limited thereto. The first electrode 190 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

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

[Description of FIGS. 2 to 4]

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

Regarding FIGS. 2 to 4, the first electrode 110, the organic layer 150, and the second electrode 190 may be understood by referring to the description presented 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 and the first capping layer 210 toward the outside, wherein the first electrode 110 may be a semi-transmissive electrode or a transmissive electrode. 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 and the second capping layer 220 toward the outside, wherein the second electrode 190 may be a semi-transmissive electrode or a transmissive electrode.

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 include the condensed cyclic compound represented by Formula 1.

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 carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrin derivatives, phthalocyanine derivatives, naphthalocyanine derivatives, alkali metal complexes, and alkaline earth-based complexes. 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 one 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 one 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 one or more 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 of the present disclosure 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, but embodiments of the present disclosure are not limited thereto.

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

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

When respective layers constituting the hole transport region, an emission layer, and respective 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., depending on a material to be included in a layer and the structure of each layer to be formed.

[General Definition of Substituents]

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched saturated aliphatic 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 iso-amyl 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 saturated monocyclic group having at least one heteroatom selected from N, O, 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 does not have 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. Non-limiting 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” 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. Non-limiting 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 rings may be condensed to each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has at least one heteroatom selected from N, O, 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 heterocyclic 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. Non-limiting 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 rings may be condensed to 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) that has two or more rings condensed to each other, only carbon atoms as a ring-forming atom, and non-aromaticity in the entire molecular structure. Examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. The term “divalent non-aromatic condensed polycyclic group,” used herein, refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group,” used herein, refers to a monovalent group (for example, having 2 to 60 carbon atoms) that has two or more rings condensed to each other, has at least one heteroatom selected from N, O, Si, P, and S, other than carbon atoms, as a ring-forming atom, and has non-aromaticity in the entire molecular structure. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having 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 having 5 to 60 carbon atoms in which a ring-forming atom is a carbon atom only. The C₅-C₆₀carbocyclic group may be an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C₅-C₆₀carbocyclic group may be a monovalent group, such as a cyclic phenyl group, such as benzene, or a divalent group, such as a phenylene group. In one or more 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 C₁-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).

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

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

wherein 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” used herein represents a phenyl group, the term “Me” used herein represents a methyl group, the term “Et” used herein represents an ethyl group, the term “ter-Bu” or “Bu^t” used herein represents a tert-butyl group, and “OMe” used herein represents a methoxy group.

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

* and *′ 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 indicates that a molar equivalent of A was identical to a molar equivalent of B.

EXAMPLE
Synthesis Example 1: Synthesis of Compound 5

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Synthesis of Intermediate A-1

Phenylboronic acid (2.44 g, 20.0 mmol), 9-bromo-10-nitrophenanthrene (6.04 g, 20.0 mmol), Pd(PPh₃)₄(1.16 g, 1.00 mmol), tetrabutylammonium bromide (TBAB) (0.322 g, 1.00 mmol), and Na₂CO₃(6.28 g, 60.0 mmol) were dissolved in 80 mL of a mixed solution of toluene/ethanol/H₂O (3/3/1), and then, stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and then, an extraction process was performed three times thereon by using 60 mL of water and 60 mL of diethylether. An organic layer was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 4.91 g of Intermediate A-1 (yield of 82%). The obtained compound was identified by LC-MS. C₂₀H₁₃NO₂: M+1 299.1

Synthesis of Intermediate A-2

Intermediate A-1 (4.91 g, 16.4 mmol), Tin (5.84 g, 49.2 mmol), and 8.2 mL (82 mmol, conc. 36.5%) of HCl were dissolved in 60 mL of ethanol, and then, stirred at a temperature of 100° C. for 8 hours. The reaction solution was cooled to room temperature, and then, 5 g of sodium hydroxide dissolved in 10 mL of water was added to a filtrate obtained by filtering under reduced pressure, and then, the result was subjected three times to an extraction process using 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 3.98 g (yield of 90%) of Intermediate A-2. The obtained compound was identified by LC-MS. C₂₀H₁₅N: M+1 269.1

Synthesis of Intermediate A-3

Intermediate A-2 (3.98 g, 14.7 mmol) and 3-bromobenzaldehyde (5.38 g, 29.4 mmol) were dissolved in 30 mL of trifluoroacetic acid, and then, the mixture was stirred in a seal tube at a temperature of 130° C. for 3 days. The reaction solution was cooled to room temperature, and then, the reaction was quenched by using NaHCO₃. The result was subjected to an extraction process using 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 3.83 g (yield of 60%) of Intermediate A-3. The obtained compound was identified by LC-MS. C₂₇H₁₆BrN: M+1 433.1

Synthesis of Compound 5

Intermediate A-3 (3.83 g, 8.82 mmol), 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile (3.05 g, 10 mmol), Pd(PPh₃)₄(0.51 g, 0.44 mmol), and K₂CO₃(3.66 g, 2.65 mmol) were dissolved in 60 mL of a mixed solution including THF/H₂O (a volumetric ratio of 2/1), and then, the mixture was stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and then, 40 mL of water was added thereto, and an extraction process was performed three times on the result by using 50 mL of ethyl ether. An organic layer obtained therefrom was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 3.63 g of Compound 5 (yield of 72%). The obtained compound was identified by MS/FAB and ¹H NMR. C₄₃H₂₈N₂cal. 572.23, found 572.22.

Synthesis Example 2: Synthesis of Compound 7

3.83 g of Compound 7 (yield of 70%) was obtained in the same manner as used to synthesize Compound 5 in Synthesis Example 1, except that 9-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2-carbonitrile was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₆H₂₇N₃O cal. 621.22, found 621.23.

Synthesis Example 3: Synthesis of Compound 12

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Synthesis of Intermediate B-1

6.05 g of Intermediate B-1 (yield of 80%) was obtained in the same manner as used to synthesize Intermediate A-1, except that 4-bromophenylboronic acid was used instead of phenylboronic acid. The obtained compound was identified by LC-MS. C₂₀H₁₂NBrO₂: M+1 377.0

Synthesis of Intermediate B-2

5.01 g of Intermediate B-2 (yield of 90%) was obtained in the same manner as used to synthesize Intermediate A-2, except that Intermediate B-1 was used instead of Intermediate A-1. The obtained compound was identified by LC-MS. C₂₀H₁₄BrN: M+1 347.0

Synthesis of Intermediate B-3

4.38 g of Intermediate B-3 (yield of 70%) was obtained in the same manner as used to synthesize Intermediate A-3, except that Intermediate B-2 was used instead of Intermediate A-2. The obtained compound was identified by LC-MS. C₂₇H₁₆BrN: M+1 433.1

Synthesis of Compound 12

4.57 g of Compound 12 (yield of 65%) was obtained in the same manner as used to synthesize Compound 5, except that 2-(3-(dinaphtho[2,1-b:1′,2′-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₅₃H₃₁NO cal. 697.24, found 697.23.

Synthesis Example 4: Synthesis of Compound 19

3.98 g of Compound 19 (yield of 60%) was obtained in the same manner as used to synthesize Compound 12 in Synthesis Example 3, except that 4,4,5,5-tetramethyl-2-(10-(naphthalen-1-yl)anthracen-9-yl)-1,3,2-dioxaborolane was used instead of 2-(3-(dinaphtho[2,1-b:1′,2′-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The obtained compound was identified by MS/FAB and ¹H NMR. C₅₁H₃₁N cal. 657.25, found 657.26.

Synthesis Example 5: Synthesis of Compound 30

4.27 g of Compound 30 (yield of 68%) was obtained in the same manner as in Synthesis Example 3, except that, in synthesizing Intermediate B-1, (4-bromonaphthalen-1-yl)boronic acid was used instead of 4-bromophenylboronic acid, and, in synthesizing Compound 12, 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile was used instead of 2-(3-(dinaphtho[2,1-b: 1′,2′-d]furan-6-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₇H₃₀N₂cal. 622.24, found 622.25.

Synthesis Example 6: Synthesis of Compound 47

4.23 g (yield of 63%) of Compound 47 was obtained in the same manner as in Synthesis Example 1, except that, in synthesizing Intermediate A-1, 2-naphthaleneboronic acid was used instead of a phenylboronic acid, and, in synthesizing Compound 5, 9-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2-carbonitrile was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₅₀H₂₉N₃cal. 671.24, found 671.23.

Synthesis Example 7: Synthesis of Compound 56

4.36 g of Compound 56 (yield of 70%) was obtained in the same manner as used to synthesize Synthesis Example 1, except that, in synthesizing Intermediate A-1, 2-pyridineboronic acid was used instead of a phenylboronic acid, and, in synthesizing Compound 5, 2-(dinaphtho[2,1-b:1′,2′-d]furan-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₆H₂₆N₂O cal. 622.20, found 622.19.

Synthesis Example 8: Synthesis of Compound 67

3.52 g of Compound 67 (yield of 60%) was obtained in the same manner as in Synthesis Example 1, except that, in synthesizing Intermediate A-1,4-pyridineboronic acid was used instead of a phenylboronic acid, in synthesizing Intermediate A-3,4-bromobenzaldehyde was used instead of 3-bromobenzaldehyde, and, in synthesizing Compound 5,3,3′-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)dipyridine was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₂H₂₆N₄cal. 586.22, found 586.21.

Synthesis Example 9: Synthesis of Compound 79

4.51 g of Compound 79 (yield of 67%) was obtained in the same manner as in Synthesis Example 1, except that, in synthesizing Intermediate A-1,8-quinolineboronic acid was used instead of a phenylboronic acid, and, in synthesizing Compound 5, 9-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole-2-carbonitrile was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₉H₂₈N₄cal. 672.23, found 672.22.

Synthesis Example 10: Synthesis of Compound 88

4.64 g of Compound 88 (yield of 69%) was obtained in the same manner as in Synthesis Example 1, except that, in synthesizing Intermediate A-1,3-isoquinolineboronic acid was used instead of phenylboronic acid, and, in synthesizing Compound 5, 2-(dinaphtho[2,1-b:1′,2′-d]furan-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was used instead of 9,9-dimethyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-fluorene-2-carbonitrile. The obtained compound was identified by MS/FAB and ¹H NMR. C₅₀H₂₈N₂O cal. 672.22, found 672.20.

Synthesis Example 11: Synthesis of Compound 89

Intermediate B-3 (3.91 g, 9.00 mmol) prepared according to Synthesis Example 3 was dissolved in 30 mL of THF, and then, at a temperature of −80° C., n-butyllithium (3.6 mL, 2.5 M in hexane) was added thereto. After one hour, at the same temperature, chlorodiphenylphosphine (1.99 g, 9 mmol) was added to the resultant mixture. The mixture was stirred at room temperature for 3 hours, followed by adding water thereto, and then, washed three times with diethylether (30 mL). A diethylether layer obtained after the washing was dried by using MgSO₄, and then, dried under reduced pressure to obtain a product. Then, 30 mL of H₂O₂was added to the product and stirred for 1 hour. Water was added to the resultant product, which was then washed three times with diethylether (30 mL). A diethylether layer obtained after the washing was dried by using MgSO₄, and then, dried under reduced pressure to obtain a product, which was then separation-purified by silica gel column chromatography to obtain 3.00 g of Compound 89 (yield of 60%), which was white solid. The obtained compound was identified by MS/FAB and ¹H NMR. C₃₉H₂₆NOP cal. 555.18, found 555.19.

Synthesis Example 12: Synthesis of Compound 91

Intermediate B-3 (4.35 g, 10.0 mmol) prepared according to Synthesis Example 3, diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide (4.04 g, 10.0 mmol), Pd(PPh₃)₄(0.58 g, 0.50 mmol), and K₂CO₃(4.15 g, 30.0 mmol) were dissolved in 60 mL of a mixed solution including THF/H₂O (a volumetric ratio of 2/1), and then, stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, followed by adding with 40 mL of water thereto, and then, washed three times with 50 mL of diethylether. A collected organic layer was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 4.29 g (yield of 68%) of Compound 91. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₅H₃₀NOP cal. 631.21, found 631.22.

Synthesis Example 13: Synthesis of Compound 103

3.45 g of Compound 103 (yield of 67%) was obtained in the same manner as in Synthesis Example 11, except that, in synthesizing Intermediate B-1, (4-bromonaphthalen-1-yl) boronic acid was used instead of 4-bromophenylboronic acid. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₃H₂₈NOP cal. 605.19, found 605.18.

Synthesis Example 14: Synthesis of Compound 119

4.29 g of Compound 119 (yield of 68%) was obtained in the same manner as in Synthesis Example 12, except that, in synthesizing Compound 91,4,4,5,5-tetramethyl-2-(10-(phenylsulfonyl)anthracen-9-yl)-1,3,2-dioxaborolane was used instead of diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide The obtained compound was identified by MS/FAB and ¹H NMR. C₄₇H₂₉NO₂S cal. 671.19, found 671.18.

Synthesis Example 15: Synthesis of Compound 129

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Synthesis of Intermediate C-1

9-bromophenanthrene (2.57 g, 10.0 mmol) was dissolved in 30 mL of THF, and then, at a temperature of −80° C., n-butyllithium (4.0 mL, 2.5 M in Hexane) was added thereto. After one hour, at the same temperature, 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.24 mL, 11 mmol) was added thereto. The resultant mixture was stirred at room temperature for 3 hours, followed by adding water thereto, and then, washed three times with 30 mL of diethylether. A diethylether layer obtained after the washing was dried by using MgSO₄, and then, dried under reduced pressure to obtain a product, which was then separation-purified by silica gel column chromatography to obtain 1.88 g (yield of 62%) of Intermediate C-1. The obtained compound was identified by MS/FAB and ¹H NMR. C₂₀H₃₁BO₂: M+1 378.0

Synthesis of Intermediate C-2

Intermediate C-1 (3.04 g, 10.0 mmol), 1,4-dibromo-2-nitrobenzene (2.81 g, 10.0 mmol), Pd(PPh₃)₄(0.58 g, 0.50 mmol), tetrabutylammonium bromide (TBAB) (0.161 g, 0.50 mmol), and Na₂CO₃(3.14 g, 30.0 mmol) were dissolved in 40 mL of a mixed solution including toluene/ethanol/H₂O (3/3/1), and then, stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, and then, subjected to an extraction process three times by using 60 mL of water and 60 mL of diethylether. An organic layer obtained therefrom was dried by using MgSO₄, and the residue obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 3.06 g of Intermediate C-2 (yield of 81%). The obtained compound was confirmed by LC-MS. C₂₀H₁₂NBrO₂: M+1 378.0

Synthesis of Intermediate C-3

Intermediate C-2 (3.78 g, 10.0 mmol), Tin (3.56 g, 30.0 mmol), and HCl 5.0 mL (50 mmol, conc. 36.5%) were dissolved in 40 mL of ethanol, and then, the mixture was stirred at a temperature of 100° C. for 8 hours. The reaction solution was cooled to room temperature, and then, 5 g of sodium hydroxide dissolved in 10 mL of water was added to a filtrate obtained by filtering the reaction solution under reduced pressure. The resultant product was subjected to an extraction process three times by using 60 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried by using MgSO₄, and the residual obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 2.99 g (yield of 86%) of Intermediate C-3. The obtained compound was confirmed by LC-MS. C₂₀H₁₄BrN: M+1 348.0

Synthesis of Intermediate C-4

Intermediate C-3 (3.48 g, 10.0 mmol) and 3-bromobenzaldehyde (3.70 g, 20.0 mmol) were dissolved in 20 mL of trifluoroacetic acid, and then, the mixture was stirred in a seal tube at a temperature of 130° C. for 3 days. The reaction solution was cooled to room temperature, followed by quenching using NaHCO₃. The resultant solution was subjected to an extraction process three times by using 40 mL of water and 60 mL of dichloromethane. An organic layer obtained therefrom was dried by using MgSO₄, and the residual obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 2.99 g of Intermediate C-4 (yield of 69%). The obtained compound was confirmed by LC-MS. C₂₇H₁₆BrN: M+1 434.1

Synthesis of Compound 129

Intermediate C-4 (4.34 g, 10.00 mmol) was dissolved in 30 mL of THF, and then, at a temperature of −80° C., n-butyllithium (4.0 mL, 2.5 M in hexane) was added thereto. After one hour, at the same temperature, chlorodiphenylphosphine (2.20 g, 10 mmol) was added to the mixture. The resultant mixture was stirred at room temperature for 3 hours, followed by adding water thereto, and then, washed three times with diethylether (30 mL). A diethylether layer was dried by using MgSO₄, and then, dried under reduced pressure to obtain a product. Then, 30 mL of H₂O₂was added thereto and stirred for 1 hour. After the stirring, water was added thereto, and the resultant product was washed three times with diethylether (30 mL). A diethylether layer obtained after the washing was dried by using MgSO₄, and then, dried under reduced pressure to obtain a product, which was then separation-purified by silica gel column chromatography to obtain 3.27 g of Compound 129 (yield of 59%). The obtained compound was identified by MS/FAB and ¹H NMR. C₃₉H₂₆NOP cal. 555.18, found 555.19.

Synthesis Example 16: Synthesis of Compound 134

Intermediate C-4 (4.34 g, 10.0 mmol) prepared according to Synthesis Example 15, diphenyl(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide (5.04 g, 10.0 mmol), Pd(PPh₃)₄(0.58 g, 0.50 mmol), and K₂CO₃(4.15 g, 30.0 mmol) were dissolved in 60 mL of a mixed solution including THF/H₂O (a volumetric ratio of 2/1), and then, the mixture was stirred at a temperature of 80° C. for 16 hours. The reaction solution was cooled to room temperature, followed by adding 40 mL of water thereto, and then, subjected to an extraction process three times by using 50 mL of diethylether. A collected organic layer was dried by using MgSO₄, and the residual obtained by evaporating a solvent therefrom was separation-purified by silica gel column chromatography, thereby completing the preparation of 4.29 g (yield of 68%) of Compound 134. The obtained compound was identified by MS/FAB and ¹H NMR. C₅₃H₃₄NOP cal. 731.24, found 731.23.

Synthesis Example 17: Synthesis of Compound 138

4.37 g (yield of 64%) of Compound 138 was obtained in the same manner as in Synthesis Example 16, except that, in synthesizing Intermediate C-2,3,6-dibromo-2-nitropyridine was used instead of 1,4-dibromo-2-nitrobenzene, and, in synthesizing Compound 134, diphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)naphthalen-1-yl)phosphine oxide was used instead of diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₈H₃₁N₂OP cal. 682.22, found 682.21.

Synthesis Example 18: Synthesis of Compound 143

3.88 g (yield of 64%) of Compound 143 was obtained in the same manner as in Synthesis Example 15, except that, in synthesizing Intermediate C-2,1,4-dibromo-2-nitronaphthalene was used instead of 1,4-dibromo-2-nitrobenzene. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₃H₂₈NOP cal. 605.19, found 605.18.

Synthesis Example 19: Synthesis of Compound 146

4.43 g of Compound 146 (yield of 65%) was obtained in the same manner as used to synthesize Synthesis Example 16, except that, in synthesizing Intermediate C-2,1,4-dibromo-2-nitronaphthalene was used instead of 1,4-dibromo-2-nitrobenzene, and, in synthesizing Compound 134, diphenyl(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phosphine oxide was used instead of diphenyl(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₈H₃₁N₂OP cal. 682.22, found 682.21.

Synthesis Example 20: Synthesis of Compound 153

4.17 g of Compound 153 (yield of 61%) was obtained in the same manner as in Synthesis Example 16, except that, in synthesizing Intermediate C-2,5,8-dibromo-6-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and, in synthesizing Compound 134, diphenyl(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)phosphine oxide was used instead of diphenyl(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₇H₃₀N₃OP cal. 685.22, found 685.23.

Synthesis Example 21: Synthesis of Compound 154

4.43 g (yield of 65%) of Compound 154 was obtained in the same manner as in Synthesis Example 16, except that, in synthesizing Intermediate C-2,5,8-dibromo-7-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and, in synthesizing Compound 134, diphenyl(3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)phenyl)phosphine oxide was used instead of diphenyl(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₈H₃₁N₂OP cal. 682.22, found 682.21.

Synthesis Example 22: Synthesis of Compound 168

4.12 g of Compound 168 (yield of 66%) was obtained in the same manner as in Synthesis Example 16, except that, in synthesizing Intermediate C-2,5,8-dibromo-6-nitroquinoline was used instead of 1,4-dibromo-2-nitrobenzene, and, in synthesizing Compound 134, 2-(phenylsulfonyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine was used instead of diphenyl(10-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)anthracen-9-yl)phosphine oxide. The obtained compound was identified by MS/FAB and ¹H NMR. C₄₁H₂₅N₃O₂S cal. 623.17, found 623.18.

Additional compounds were synthesized by using the same synthesis paths and methods as described above and appropriate intermediate materials. Table 1 shows ¹H NMR and MS/FAB of these compounds are shown in Table 1.

Synthesis methods for other compounds than the compounds shown in Table 1 may be understood by one of ordinary skill in the art by referring to the synthesis paths and source materials described above.

TABLE 1

MS/FAB

Compound

¹H NMR (CDCl₃400 MHz) δ
found
calc.

5
δ = 9.23 (d, 1H), 8.87 (d, 1H), 8.69-8.65 (m, 2H), 8.36-
572.22
572.23

8.34 (m, 1H), 8.22 (d, 1H), 7.92-7.76 (m, 7H), 7.70-7.64 (m,

3H), 7.60-7.45 (m, 4H), 7.36 (t, 1H), 7.12-7.08 (m, 1H),

1.65 (s, 6H)

7
δ = 9.22 (d, 1H), 8.86 (d, 1H), 8.69-8.66 (m, 2H), 8.57-
621.23
621.22

8.55 (m, 1H), 8.23-8.21 (m, 2H), 8.08 (d, 1H), 8.03 (d, 1H),

7.92-7.76 (m, 7H), 7.70-7.48 (m, 8H), 7.41 (t, 1H), 7.32-

7.28 (m, 1H), 7.13-7.09 (m, 1H)

12
δ = 9.23-9.19 (m, 1H), 8.83 (t, 2H), 8.69-8.63 (m, 4H),
697.23
697.24

8.33 (s, 1H), 8.06-7.90 (m, 7H), 7.86-7.48 (m, 15H), 7.09 (t,

1H)

19
δ = 9.22-9.20 (m, 1H), 8.82, 8.73-8.65 (m, 4H), 8.18 (d,
657.26
657.25

1H), 7.98-7.96 (m, 2H), 7.86-7.79 (m, 6H), 7.72-7.44 (m,

10H), 7.40-7.27 (m, 5H), 7.09 (t, 1H), 6.96 (t, 1H)

30
δ = 9.27 (d, 1H), 8.86 (d, 1H), 8.70 (d, 1H), 8.67 (d, 1H),
622.25
622.24

8.28 (s, 1H), 8.20-8.18 (m, 2H), 8.06-8.02 (m, 2H), 7.95-

7.79 (m, 5H), 7.74-7.45 (m, 8H), 7.23 (t, 1H), 7.07 (t, 1H),

1.66 (s, 6H)

47
δ = 9.29-9.26 (m, 1H), 8.82-8.76 (m, 2H), 8.70-8.64 (m, 3
671.23
671.24

H), 8.23, 8.16-8.03 (m, 5H), 7.94 (d, 1H), 7.89-7.79 (m, 6

H), 7.70-7.45 (m, 8H), 7.42 (t, 1H), 7.32-7.28 (m, 1H),

7.13 (t, 1H)

56
δ = 9.31-9.28 (m, 1H), 9.01 (d, 1H), 8.89-8.76 (m, 5H), 8.60-
622.19
622.20

8.56 (m, 2H), 8.39 (s, 1H), 7.96-7.87 (m, 6H), 7.83-

7.78 (m, 3H), 7.72-7.48 (m, 6H), 7.37 (t, 1H)

67
δ = 9.52-9.50 (m, 1H), 9.23-9.21 (m, 1H), 8.94 (d, 2H), 8.81
586.21
586.22

(d, 1H), 8.69-8.65 (m, 4H), 8.46 (d, 1H), 8.38-8.35 (m,

2H), 8.06-8.00 (m, 3H), 7.95-7.79 (m, 8H), 7.54-7.46 (m,

3H)

79
δ = 9.53-9.51 (m, 1H), 9.18 (d, 1H), 8.80-8.70 (m, 3H), 8.46
672.22
672.23

(d, 1H), 8.27 (d, 1H), 8.23 (d, 1H), 8.08 (d, 1H), 8.04-

7.94 (m, 3H), 7.86-7.76 (m, 5H), 7.70-7.48 (m, 8H), 7.41 (t,

1H), 7.31-7.28 (m, 1H), 7.16 (t, 1H)

88
δ = 9.55 (d, 1H), 9.37-8.34 (m, 1H), 8.92 (d, 1H), 8.85-
672.20
672.22

8.76 (m, 3H), 8.67-8.63 (m, 2H), 8.39 (d, 1H), 8.29 (dd, 1H),

8.19 (d, 1H), 8.01-7.76 (m, 11H), 7.72-7.48 (m, 6H)

89
δ = 9.23-9.16(m, 2H), 8.74-8.66(m, 3H), 7.95-7.93(m, 1H),
555.19
555.18

7.85-7.81(m, 5H), 7.69-7.61(m, 7H), 7.55-7.47(m, 3H), 7.45-

7.39(m, 4H), 7.12-7.07(m, 1H)

91
δ = 9.23-9.21(m, 1H), 8.71-8.65(m, 2H), 8.52-8.50(m, 1H),
631.22
631.21

8.37-8.36(m, 1H), 8.13-8.11(m, 1H), 7.98-7.97(m, 2H), 7.87-

7.81(m, 4H), 7.68-7.61(m, 8H), 7.57-7.48(m, 5H), 7.44-

7.41(m, 4H), 7.12-7.08(m, 1H)

103
δ = 9.29-9.24(m, 2H), 8.96-8.94(m, 1H), 8.78-8.71(m, 2H),
605.18
605.19

8.67-8.66(m, 1H), 8.01-8.00(m, 2H), 7.85-7.81(m, 2H), 7.74-

7.72(m, 4H), 7.68-7.66(m, 2H), 7.63-7.53(m, 5H), 7.51-

7.49(m, 1H), 7.41-7.39(m, 4H), 7.08-7.06(m, 1H)

119
δ = 9.76-9.74(m, 1H), 9.26-9.22(m, 2H), 8.85-8.68(m, 4H),
671.18
671.19

8.06-8.01(m, 2H), 7.96-7.93(m, 3H), 7.80-7.63(m, 12H), 7.54-

7.52(m, 2H), 7.44-7.42(m, 4H)

129
δ = 8.84-8.83(m, 2H), 8.71-8.61(m, 4H), 8.00-7.99(m, 2H),
555.19
555.18

7.84-7.74(m, 3H), 7.70-7.68(m, 5H), 7.64-7.62(m, 4H), 7.49-

7.42(m, 5H)

134
δ = 8.84-8.83(m, 2H), 8.71-8.62(m, 3H), 8.20-8.18(m, 2H),
731.23
731.24

8.04-8.00(m, 3H), 7.83-7.68(m, 4H), 7.64-7.62(m, 8H), 7.54-

7.45(m, 6H), 7.39-7.37(m, 4H), 7.19-7.16(m, 2H)

138
δ = 8.93-8.85(m, 4H), 8.73-8.71(m, 1H), 8.59-8.55(m, 2H),
682.21
682.22

8.01-7.92(m, 4H), 7.79-7.72(m, 10H), 7.64-7.63(m, 2H), 7.53-

7.51(m, 3H), 7.45-7.39(m, 5H)

143
δ = 8.92-8.90(m, 2H), 8.85-8.69(m, 5H), 8.02-8.00(m, 2H),
605.18
605.19

7.80-7.69(m, 8H), 7.65-7.63(m, 4H), 7.55-7.53(m, 3H), 7.40-

7.38(m, 4H)

146
δ = 8.93-8.85(m, 4H), 8.79-8.77(m, 2H), 8.66-8.59(m, 2H),
682.21
682.22

8.40-8.39(m, 1H), 8.02-7.97(m, 3H), 7.83-7.80(m, 6H), 7.74-

7.69(m, 2H), 7.64-7.63(m, 4H), 7.50-7.48(m, 3H), 7.41-

7.39(m, 4H)

153
δ = 9.76-9.74(m, 1H), 9.26-9.22(m, 2H), 8.85-8.68(m, 4H),
685.23
685.22

8.06-8.01(m, 2H), 7.96-7.93(m, 3H), 7.80-7.63(m, 12H), 7.54-

7.52(m, 2H), 7.44-7.42(m, 4H)

154
δ = 9.06-9.02(m, 2H), 8.94-8.79(m, 3H), 8.65-8.63(m, 1H),
682.21
682.22

8.39-8.38(m, 1H), 8.22-8.21(m, 1H), 8.02-7.93(m, 3H), 7.80-

7.74(m, 3H), 7.65-7.63(m, 9H), 7.57-7.56(m, 1H), 7.50-

7.48(m, 3H), 7.44-7.41(m, 4H)

168
δ = 9.76-9.74(m, 2H), 9.26-9.25(m, 1H), 8.85-8.77(m, 3H),
623.18
623.17

8.70-8.69(m, 1H), 8.40-8.38(m, 1H), 8.15-8.14(m, 1H), 8.05-

8.02(m, 4H), 7.89-7.80(m, 3H), 7.74-7.69(m, 2H), 7.65-

7.55(m, 7H)

Example 1

As a substrate and an anode, a Corning 150/cm²(1200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, and then, sonicated with isopropyl alcohol and pure water, each for 5 minutes, and then, cleaned by exposure to ultraviolet light for 30 minutes, and then, to ozone. The resultant glass substrate was mounted on a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on the ITO anode on the glass substrate to form a hole injection layer having a thickness of 600 Å, and then, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å.

9,10-di-naphthalene-2-yl-anthracene (ADN), which is a host, and 4,4′-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi), which is a dopant, were co-deposited at a weight ratio of 98 2 on the hole transport layer to form an emission layer having a thickness of 300 Å.

Compound 5 was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 3,000 Å, thereby completing manufacture of an organic light-emitting device.

embedded image

Examples 2 to 22 and Comparative Examples 1 and 2

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

Evaluation Example 1

The driving voltage, current density, luminance, efficiency, emission color, and half lifespan of the organic light-emitting devices manufactured according to Examples 1 to 22 and Comparative Examples 1 and 2 were measured by using Keithley SMU 236 and luminance meter PR650. Results thereof are shown in Table 2.

TABLE 2

Driving
Current

voltage
density
Luminance
Efficiency
Emission
Half lifespan

Material
(V)
(mA/cm²)
(cd/m²)
(cd/A)
color
(hr @100 mA/cm²)

Example 1
Compound 5
3.60
50
3,425
7.20
Blue
618

Example 2
Compound 7
3.42
50
3,755
8.12
Blue
625

Example 3
Compound 12
3.54
50
3,500
7.53
Blue
656

Example 4
Compound 19
3.38
50
3,615
8.07
Blue
602

Example 5
Compound 30
3.47
50
3,830
8.27
Blue
635

Example 6
Compound 47
3.33
50
3,550
7.75
Blue
620

Example 7
Compound 56
3.46
50
3,745
8.03
Blue
635

Example 8
Compound 67
3.50
50
3,570
7.55
Blue
662

Example 9
Compound 79
3.47
50
3,600
8.10
Blue
627

Example 10
Compound 88
3.52
50
3,815
8.16
Blue
640

Example 11
Compound 89
3.60
50
3,425
6.85
Blue
618

Example 12
Compound 91
3.42
50
3,755
7.51
Blue
625

Example 13
Compound 103
3.54
50
3,500
7.00
Blue
656

Example 14
Compound 119
3.38
50
3,615
7.23
Blue
602

Example 15
Compound 129
3.47
50
3,830
7.66
Blue
635

Example 16
Compound 134
3.34
50
3,727
7.45
Blue
627

Example 17
Compound 138
3.41
50
3,750
7.50
Blue
637

Example 18
Compound 143
3.37
50
3,627
7.25
Blue
608

Example 19
Compound 146
3.52
50
3,635
7.27
Blue
650

Example 20
Compound 153
3.59
50
3,487
6.97
Blue
591

Example 21
Compound 154
3.42
50
3,562
7.12
Blue
613

Example 22
Compound 168
3.48
50
3,612
7.22
Blue
647

Comparative
Compound A
5.06
50
3,010
6.52
Blue
325

Example 1

Comparative
Compound B
4.88
50
2,948
5.89
Blue
411

Example 2

embedded image

Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 22 had better characteristics than those of Comparative Examples 1 and 2, in terms of a driving voltage, luminance, efficiency, and a half lifespan.

An organic light-emitting device including the condensed cyclic compound according to an embodiment may have a low driving voltage, high luminance, high efficiency, and a long lifespan.

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

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

Number	Date	Country	Kind
10-2015-0182792	Dec 2015	KR	national
10-2016-0046499	Apr 2016	KR	national

Number	Name	Date	Kind
5645948	Shi et al.	Jul 1997	A
8253129	Kawamura	Aug 2012	B2
8986855	Lim et al.	Mar 2015	B2
9005771	Ma et al.	Apr 2015	B2
9028978	Kim et al.	May 2015	B2
10069083	Jeong et al.	Sep 2018	B2
20070170419	Gerhard	Jul 2007	A1
20070241670	Sapochak	Oct 2007	A1
20140103325	Shin et al.	Apr 2014	A1
20160204357	Jang	Jul 2016	A1

Number	Date	Country
10-17860	Jan 1998	JP
11-87067	Mar 1999	JP
2002-63989	Feb 2002	JP
4060669	Dec 2007	JP
10-0525408	Nov 2005	KR
10-2010-0088613	Aug 2010	KR
10-2011-0077871	Jul 2011	KR
10-2012-0023780	Mar 2012	KR
10-2012-0122982	Jul 2012	KR
10-2012-0138673	Dec 2012	KR
10-2013-0000230	Jan 2013	KR
10-2013-0007162	Jan 2013	KR
10-2013-0135178	Oct 2013	KR
1558495	Nov 2014	KR
10-2015-0051119	Nov 2015	KR
10-2015-0139125	Dec 2015	KR

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

Information

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Date Issued

Inventors

Original Assignees

Examiners

Agents

CPC

Field of Search

CPC

International Classifications

Term Extension

Abstract

Description

Claims

Priority Claims (2)

US Referenced Citations (10)

Foreign Referenced Citations (16)

Non-Patent Literature Citations (6)

Related Publications (1)

Entry
Tang, “Organic electroluminescent diodes”, Appl.Phys. Lett. ; 51, 913 (1987); doi: 10.1063/1.98799.
Adachi, Appl. Phys. Lett. “Confinement of charge carriers and molecular excitons within 5nmthick emitter layer in organic electroluminescent devices with a double heterostructure”; 57, 531 (1990); doi: 10.1063/1.103638.
Sakamoto, “Synthesis, Characterization, and Electron-Transport”, J. Am. Chem. Soc. 2000, 122, 1832-1833.
Yamaguchi, “Diphenylamino-Substituted 2,5-Diarylsiloles for Single-Layer Organic Electroluminescent Devices”, Chem. Lett., 98 (2001).
Johansson, “Solid-State Amplified Spontaneous Emission in Some Spiro-Type Molecules: A New Concept for the Design of Solid State Lasing Molecules” Adv. Mater., 10, 1136 (1998).
Tao, “Sharp green electroluminescence from 1H-pyrazolo[3,4-b]quinoline-based light-emitting diodes”, Appl. Phys. Lett., 77, 1575 (2000).