ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

CROSS-REFERENCE TO RELATED APPLICATION

This application claims the benefit of Korean Patent Application No. 10-2019-0030024, filed on Mar. 15, 2019, in the Korean Intellectual Property Office, the disclosure of which is incorporated herein in its entirety by reference.

BACKGROUND
1. Field

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

2. Description of the Related Art

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

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

SUMMARY

One or more embodiments include a novel organometallic 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.

An aspect of the present disclosure provides an organometallic compound represented by Formula 1:

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In Formula 1,

M₁may be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm),

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

L₁and L₄may each independently be selected from a single bond, *—O—*′, *—S—*', *—C(R₅)(R₆)—*′, *—C(R₅)—*′, *—C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′,

L₂and L₃may each independently be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′,

at least one selected from L₂and L₃may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, and at least one pair of R₅and R₆selected from R₅and R₆in L₂and R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

a1 and a4 may each independently be selected from 0, 1, 2, and 3, wherein the sum of a1 and a4 may be 1 or more, when a1 is 0, ring A₁and ring A₂are not linked with each other, and when a4 is 0, ring A₁and ring A₄are not linked with each other,

a2 and a3 may each independently be selected from 1, 2, and 3,

Y₁to Y₄may each independently be selected from a carbon atom (C) and a nitrogen atom (N),

B₁to B₄may each independently be selected from a chemical bond, *—O—*′, and *—S—*′,

R₁to R₆may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-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(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),

two neighboring substituents among R₁to R₆may optionally be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

b1 to b4 may each independently be an integer from 1 to 5,

* and *′ each indicate a binding site to a neighboring atom,

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

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group;

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

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 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), and

Q₁to Q₃, 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 amino 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.

Another aspect of the present disclosure provides an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode and including an emission layer; and at least one organometallic compound 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 view of an organic light-emitting device according to an embodiment;

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

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

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

DETAILED DESCRIPTION

An organometallic compound according to an embodiment is represented by Formula 1 below:

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In Formula 1, M₁may be selected from platinum (Pt), palladium (Pd), copper (Cu), zinc (Zn), silver (Ag), gold (Au), rhodium (Rh), iridium (Ir), ruthenium (Ru), rhenium (Re), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), and thulium (Tm).

In one embodiment, M₁may be selected from Pt, Pd, Cu, Ag, and Au. For example, M₁may be Pt.

In Formula 1, ring A₁to ring A₄may each independently be selected from a C₅-C₆₀carbocyclic group and a C₁-C₆₀heterocyclic group.

In one embodiment, ring A₁to ring A₄in Formula 1 may each independently be selected from a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, an azulene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a furan group, a thiophene group, a silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an indenopyridine group, an indolopyridine group, a benzofuropyridine group, a benzothienopyridine group, a benzosilolopyridine group, an indenopyrimidine group, an indolopyrimidine group, a benzofuropyrimidine group, a benzothienopyrimidine group, a benzosilolopyrimidine group, a dihydropyridine group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a 2,3-dihydroimidazole group, a triazole group, a 2,3-dihydrotriazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a pyrazolopyridine group, a furopyrazole group, a thienopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, a furoimidazole group, a thienoimidazole group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, an imidazopyrazine group, a 2,3-dihydroimidazopyrazine group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

In one embodiment, in Formula 1, ring A₃may be a 6-membered ring including one or more N atoms, and one selected from ring A₁, ring A₂, and ring A₄may be a 5-membered ring including two or more N atoms.

In one or more embodiments, in Formula 1, ring A₃may be a 6-membered ring including one or more N atoms, and one selected from ring A₁and ring A₂may be a 5-membered ring including two or more N atoms.

In one or more embodiments, in Formula 1, ring A₃may be a 6-membered ring including one or more N atoms, and Y₃may be N. For example, ring A₃may be a pyridine group.

In one embodiment, in Formula 1, ring A₃may be a group which is represented by Formula 2-2(1) and in which Y₁₅is N,

ring A₁, ring A₂, and ring A₄may each independently be selected from groups represented by Formulae 2-1(1) to 2-1(35) and 2-2(1) to 2-2(25):

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In Formulae 2-1(1) to 2-1(35) and 2-2(1) to 2-2(25),

Y₁₅may be a carbon atom (C) or a nitrogen atom (N),

X₂₁may be N or C(R₂₁), X₂₂may be N or C(R₂₂), X₂₃may be N or C(R₂₃), X₂₄may be N or C(R₂₄), X₂₅may be N or C(R₂₅), X₂₆may be N or C(R₂₆), X₂₇may be N or C(R₂₇), and X₂₈may be N or C(R₂₈),

X₂₉may be C(R_29a)(R_29b), Si(R_29a)(R_29b), N(R₂₉), O, or S,

X₃₀may be C(R_30a)(R_30b), Si(R_30a)(R_30b), N(R₃₀), O, or S,

R₂₁to R₃₀and R_25ato R_30bmay each independently be the same as defined in connection with R₁to R₄in Formula 1,

* indicates a binding site to B₁, B₂, B₃, or B₄, and

*′ and *″ each indicate a binding site to a neighboring atom.

In one embodiment, in Formulae 2-1(1) to 2-1(35) and 2-2(1) to 2-2(25), R₂₁to R₃₀and R_25ato R_30bmay each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano 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 cyano group, a phenyl group, and a biphenyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, and a triazinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, and a triazinyl group.

For example, in Formulae 2-1(1) to 2-1(35) and 2-2(1) to 2-2(25), R₂₁to R₃₀and R_25ato R_30bmay each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a pyridinyl group.

In one embodiment, in Formula 1, a4 may be 0, ring A₁and ring A₄may each independently be selected from groups represented by Formulae 2-1(1) to 2-1(35), ring A₂may be selected from groups represented by Formulae 2-2(1) to 2-2(25), ring A₃may be a group which is represented by Formula 2-2(1) and in which Y₁₅is N.

For example, in Formula 1, a4 may be 0, ring A₁may be a group represented by Formula 2-1(32), ring A₂may be a group represented by Formula 2-2(1), ring A₃may be a group which is represented by Formula 2-2(1) and in which Y₁₅is N, and ring A₄ring may be a group represented by Formula 2-1(1).

In one embodiment, in Formula 1, a4 may be 0, ring A₁and ring A₄may each independently be a group represented by Formula 2-1(1), ring A₂may be a group represented by Formula 2-2(10), 2-2(12), or 2-2(20), and ring A₃may be a group which is represented by Formula 2-2(1) and in which Y₁₅is N.

In Formula 1, L₁and L₄may each independently be selected from a single bond, *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, and

L₂and L₃may each independently be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)≡C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, wherein at least one selected from L₂and L₃may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′.

When at least one selected from L₂and L₃is selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, at least one pair of R₅and R₆selected from R₅and R₆in L₂and R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

That is, when L₂is selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′ and L₃is selected from *—O—*′, *—S—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, and *—P(R₅)—*′, R₅and R₆in L₂may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

when L₃is selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′ and L₂is selected from *—O—*′, *—S—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, and *—P(R₅)—*′, R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group, and

when L₂and L₃are each independently selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, at least one pair of R₅and R₆selected from R₅and R₆in L₂and R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In Formula 1, a1 and a4 may each independently be selected from 0, 1, 2, and 3, wherein the sum of a1 and a4 is 1 or more. When a1 is 0, ring A₁and ring A₂are not linked with each other, and when a4 is 0, ring A₁and ring A₄are not linked with each other.

a1 indicates the number of L₁, wherein, when a1 is two or more, a plurality of L₁(s) may be identical to or different from each other. When L₁is a single bond, ring A₁and ring A₂may be directly linked with each other.

a4 indicates the number of L₄, wherein, when a4 is two or more, a plurality of L₂(s) may be identical to or different from each other. When L₄is a single bond, ring A₁and ring A₄may be directly linked with each other.

In one embodiment, the sum of a1 and a4 in Formula 1 may be 1. That is, a1 may be 1, and a4 may be 0; or a1 may be 0, and a4 may be 1.

For example, a1 may be 1, and a4 may be 0.

In Formula 1, a2 and a3 may each independently be selected from 1, 2, and 3.

a2 indicates the number of L₂, wherein, when a2 is 2 or more, a plurality of L₂(s) may be identical to or different from each other. a3 indicates the number of L₃, wherein, when a3 is 2 or more, a plurality of L₃(s) may be identical to or different from each other.

In one embodiment, in Formula 1, i) a2 and a3 may each be 1, L₂may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, L₃may be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, and *—N(R₅)—*′, and R₅and R₆in L₂may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group;

ii) a2 and a3 may each be 1, L₂may be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, and *—N(R₅)—*′, L₃may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, and R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group; or

iii) a2 and a3 may each be 1, L₂and L₃may each independently be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, and at least one pair of R₅and R₆selected from R₅and R₆in L₂and R₅and R₆in L₃may be linked to form a substituted or unsubstituted C₅-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group.

In one embodiment, in Formula 1, at least one selected from L₂and L₃may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, and at least one pair of R₅and R₆selected from R₅and R₆in L₂and R₅and R₆in L₃may be linked to form a group represented by Formula 3:

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In Formula 3,

X₃₁may be selected from a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(R₃₃)(R₃₄)—*, *—C(R₃₃)═C(R₃₄)—*′, *—Si(R₃₃)(R₃₄)—*′, and *—Ge(R₃₃)(R₃₄)—*′,

A₃₁and A₃₂may each independently be selected from a C₆-C₃₀carbocyclic group and a C₁-C₃₀heterocyclic group,

R₃₁to R₃₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-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(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

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,

b31 and b32 may each independently be selected from 1, 2, 3, 4, 5, and 6, and

* indicates a binding site to C, Si, P, or Ge.

In one or more embodiments, at least one selected from L₂and L₃in Formula 1 may be selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′, wherein a pair of R₅and R₆selected from R₅(s) in the number of L₂and R₆(s) in the number L₃may be linked with each other to form a group represented by Formula 3A:

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In Formula 3A,

X₃₁and R₃₁to R₃₄may each independently be the same as defined in connection with Formula 3,

b31 and b32 may each independently be selected from 1, 2, 3, and 4, and

* indicates a binding site to C, Si, P, or Ge.

In one embodiment, in Formulae 3 and 3A, R₃₁to R₃₄may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano 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 cyano group, a phenyl group, and a biphenyl group;

For example, R₃₁to R₃₄in Formulae 3 and 3A may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a pyridinyl group.

In Formula 1, Y₁to Y₄may each independently be selected from a carbon atom (C) and a nitrogen atom (N).

In one embodiment, i) Y₁, Y₂, and Y₄may each be C, and Y₃may be N; ii) Y₁and Y₂may each be C, and Y₃and Y₄may each be N; iii) Y₁and Y₄may each be C, and Y₂and Y₃may each be N; or iv) Y₂and Y₄may each be C, and Y₁and Y₃may each be N.

For example, i) Y₁, Y₂, and Y₄may each be C, and Y₃may be N; or ii) Y₁and Y₄may each be C, and Y₂and Y₃may each be N.

In one embodiment, each of B₁to B₄may be a chemical bond, Y₃may be N, and a bond between Y₃and M₁may be a coordinate bond,

i) Y₁, Y₂, and Y₄may each be C, one bond selected from a bond between Y₁and M₁, a bond between Y₂and M₁, and a bond between Y₄and M₁may be a coordinate bond, and the others thereof may be a covalent bond;

ii) Y₁and Y₄may each be C, Y₂may be N, a bond between Y₂and M₁may be a coordinate bond, and a bond between Y₁and M₁and a bond between Y₄and M₁may be a covalent bond; or

iii) Y₁may be N, Y₂and Y₄may each be C, a bond between Y₁and M₁may be a coordinate bond, and a bond between Y₂and M₁and a bond between Y₄and M₁may be a covalent bond.

In Formula 1, B₁to B₄may each independently be selected from a chemical bond, *—O—*′, and *—S—*′.

When B₁is a chemical bond, Y₁and M₁may be directly linked with each other, when B₂is a chemical bond, Y₂and M₁may be directly linked with each other, when B₃is a chemical bond, Y₃and M₁may be directly linked with each other, and when B₄is a chemical bond, Y₄and M₁may be directly linked with each other.

In one embodiment, in Formula 1, i) each of B₁to B₄may be a chemical bond; or ii) at least one selected from B₁to B₄may be *—O—*′ or *—S—*′, and the others thereof may be a chemical bond.

For example, each of B₁to B₄may be a chemical bond. In one embodiment, each of B₁to B₃may be a chemical bond, and B₄may be *—O—*′.

In Formula 1, R₁to R₆may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-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(Q₁)(Q₂)(Q₃), —B(Q₁)(Q₂), —N(Q₁)(Q₂), —P(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)(Q₁), —S(═O)₂(Q₁), —P(═O)(Q₁)(Q₂), and —P(═S)(Q₁)(Q₂),

In one embodiment, R₁to R₆may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano 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 cyano group, a phenyl group, and a biphenyl group;

In one or more embodiments, R₁to R₆may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, and a pyridinyl group.

In Formula 1, b1 to b4 may each independently be an integer from 1 to 5.

b1 indicates the number of R₁, wherein, when b1 is two or more, two or more R₁(s) may be identical to or different from each other.

b2 indicates the number of R₂, wherein, when b2 is two or more, two or more R₂(s) may be identical to or different from each other.

b3 indicates the number of R₃, wherein, when b3 is two or more, two or more R₃(s) may be identical to or different from each other.

b4 indicates the number of R₄, wherein, when b4 is two or more, two or more R₄(s) may be identical to or different from each other.

In the description regarding Formula 1, * and *′ each indicate a binding site to a neighboring atom.

In the description regarding Formula 1, at least one substituent of the substituted C₅-C₆₀carbocyclic group, the substituted C₁-C₆₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

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

In one embodiment, the organometallic compound may be represented by one of Formulae 1-1 to 1-3:

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In Formulae 1-1 to 1-3,

L₂and L₃may each independently be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′,

X₁and X₂may each independently be selected from C, Si, P, and Ge,

X₂₂may be N or C(R₂₂), X₂₃may be N or C(R₂₃), and X₂₄may be N or C(R₂₄),

X₃₂may be selected from a single bond, *—O—*′, *—S—*′, *—Se—*′, *—C(R₃₇)(R₃₈)—*, *—C(R₃₇)═C(R₃₈)—*′, *—Si(R₃₇)(R₃₈)—*′ and *—Ge(R₃₇)(R₃₈)—*′,

R₂₂to R₂₄may each independently be the same as defined in connection with R₃in Formula 1, R₃₁to R₃₄may each independently be the same as described above, and R₃₅to R₃₈may each independently be the same as defined in connection with R₃₁to R₃₄in Formula 3,

b31, b32, b35, and b36 may each independently be selected from 1, 2, 3, and 4,

M₁, ring A₁, ring A₂, ring A₄, L₁, L₄, a1, a4, Y₁to Y₄, B₁to B₄, R₁, R₂, R₄, b1, b2, and b4 may each independently be the same as defined in connection with Formula 1.

In one embodiment, in Formulae 1-1 to 1-3,

i) L₂and L₃may each independently be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, and *—N(R₅)—*′;

ii) L₂may be *—N(R₅)—*′, and R₅may be linked with neighboring R₂or R₂₂; or

iii) L₃may be *—N(R₅)—*′, and R₅may be linked with neighboring R₄or R₂₄.

In one embodiment, in Formulae 1-1 to 1-3, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), and X₂₄may be C(R₂₄). For example, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), X₂₄may be C(R₂₄), R₂₂and R₂₄may be hydrogen, and R₂₃may be hydrogen or a tert-butyl group.

In one or more embodiments, in Formulae 1-1 to 1-3, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), X₂₄may be C(R₂₄), and at least one selected from R₂₂to R₂₄, R₃₁, R₃₂, R₃₅, and R₃₆may not be hydrogen.

In one or more embodiments, the organometallic compound may be represented by one of Formulae 1-1A to 1-3A:

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In Formulae 1-1A to 1-3A,

L₂, L₃, X₁, X₂, X₂₂to X₂₄, R₃₁, R₃₂, R₃₅, R₃₆, b31, b32, b35, and b36 may each independently be the same as defined in connection with Formulae 1-1 to 1-3, and

M₁, ring A₁, ring A₂, ring A₄, L₁, L₄, a1, a4, Y₁to Y₄, B₁to B₄, R₁, R₂, R₄, b1, b2, and b4 may each independently be the same as defined in connection with Formula 1.

In one embodiment, in Formulae 1-1A to 1-3A,

i) L₂and L₃may each independently be selected from *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, and *—N(R₅)—*′;

ii) L₂may be *—N(R₅)—*′, and R₅may be linked with neighboring R₂or R₂₂; or

iii) L₃may be *—N(R₅)—*′, and R₅may be linked with neighboring R₄or R₂₄.

In one embodiment, in Formulae 1-1A to 1-3A, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), and X₂₄may be C(R₂₄). For example, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), X₂₄may be C(R₂₄), R₂₂and R₂₄may be hydrogen, and R₂₃may be hydrogen or a tert-butyl group.

In one or more embodiments, in Formulae 1-1A to 1-3A, X₂₂may be C(R₂₂), X₂₃may be C(R₂₃), X₂₄may be C(R₂₄), and at least one selected from R₂₂to R₂₄, R₃₁, R₃₂, R₃₅, and R₃₆may not be hydrogen.

In one embodiment, the organometallic compound represented by Formula 1 may be one selected from Compounds 1 to 40:

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In the organometallic compound represented by Formula 1, ring A₃is linked to ring A₂and ring A₄via linkers L₂and L₃, thereby increasing the rigidity of ring A₃. In addition, in the organometallic compound represented by Formula 1, bond dissociation energy of a metal center M₁and ring A₃may be increased, as compared with an organometallic complex including an organic ligand in which one of linkers L₂and L₃does not exist (that is, an organic ligand with which ring A₂and ring A₃are not linked, or ring A₃and ring A₄are not linked). Accordingly, the stability in the ground state of the organometallic compound may be increased, thereby improving the lifespan thereof. Therefore, the durability of the organic light-emitting device to which the organometallic compound is applied may be increased, thereby improving the lifespan thereof.

Furthermore, since the organometallic compound represented by Formula 1 has a high energy level of a triplet metal-centered state (³MC state), the stability of the compound in the excited state may be improved. Therefore, since a non-radiative decay phenomenon is reduced, when the organometallic compound is applied to an electronic device, for example, an organic light-emitting device, the device may have a long lifespan.

Furthermore, at least one selected from the linkers L₂and L₃is selected from *—C(R₅)(R₆)—*′, *—Si(R₅)(R₆)—*′, *—P(R₅)(R₆)—*′, and *—Ge(R₅)(R₆)—*′. The at least one selected from the linkers L₂and L₃includes a ring structure in which R₅and R₆bonded to an atom (C, Si, P, or Ge) in the linkers are linked via a single bond or a linking group. This ring structure causes steric hindrance in the organometallic compound represented by Formula 1. When the organometallic compound is applied to an emission layer dopant of the organic light-emitting device, it may hinder the formation of excimer or exciplex due to an interaction between the dopants or between the dopant and the host. Therefore, it is possible to maintain high efficiency and color purity during the driving of the device.

A synthesis method for the organometallic compound represented by Formula 1 would be apparent to those of ordinary skill in the art by referring to the following examples.

The organometallic compound represented by Formula 1 may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound may be included in an emission layer. The organometallic compound may act as a dopant in the emission layer. In one or more embodiments, the organometallic compound of Formula 1 may be used as a material for a capping layer located outside a pair of electrodes of an organic light-emitting device.

Accordingly, there is provided an organic light-emitting device including: a first electrode; a second electrode facing the first electrode; an organic layer between the first electrode and the second electrode; and at least one organometallic compound represented by Formula 1.

In one embodiment, the organic layer of the organic light-emitting device may include the at least one organometallic compounds represented by Formula 1.

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

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

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

In one or more embodiments, the emission layer of the organic light-emitting device may include the at least one organometallic compound.

In one or more embodiments, the emission layer of the organic light-emitting device may include the at least one organometallic compound, the emission layer may further include a host, and an amount of the host included in the emission layer may be larger than an amount of the organometallic compound included in the emission layer. For example, the amount of the organometallic compound may be in a range of about 0.01 parts by weight to about 30 parts by weight based on 100 parts by weight of the emission layer.

In one embodiment, the emission layer may include the organometallic compound, and the emission layer may emit blue light or green light. For example, the emission layer may emit blue light or green light having a wavelength of maximum emission in a range of about 400 nm or more and about 600 nm or less, for example, a wavelength of maximum emission in a range of about 460 nm or more and about 570 nm or less. The wavelength of maximum emission of the organometallic compound is a value obtained through quantum simulation using a density functional theory (DFT) calculation method.

In one embodiment, the hole transport region may include an electron blocking layer, and the electron blocking layer may include the organometallic compound; or the electron transport region may include a hole blocking layer, and the hole blocking layer may include the organometallic compound.

In one embodiment, the hole transport region may include a p-dopant having a lowest unoccupied molecular orbital (LUMO) energy level of −3.5 eV or less.

In one embodiment, the electron transport region may include a phosphine oxide-containing compound and/or a silyl-containing compound. For example, the electron transport region may include a hole blocking layer, the hole blocking layer may directly contact the emission layer, and the hole blocking layer may include the phosphine oxide-containing compound and/or a silyl-containing compound.

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

[Description of FIG. 1]

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

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

[First Electrode 110]

In FIG. 1, a substrate may be 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 transmissive 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-transmissive 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 may be 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 a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

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

For example, the hole transport region may have a single-layered structure including a single layer including 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. For each structure, constituting layers are sequentially stacked from the first electrode 110 in this stated order, but the structure of the hole transport region is not limited thereto.

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

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In Formulae 201 and 202,

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

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

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

xa5 may be an integer from 1 to 10,

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

For example, in Formula 202, R₂₀₁and R₂₀₂may optionally be linked 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:

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

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

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

Q₃₁to Q₃₃are the same as described above.

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

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

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a phenyl group substituted with a C₁-C₁₀alkyl group, a phenyl group substituted with —F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

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

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

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In one embodiment, 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 L_203,xa1 to xa3, xa5, and R₂₀₂to R₂₀₄may be understood by referring to corresponding description presented herein,

R₂₁₁and R₂₁₂may each independently be the same as defined in connection with R₂₀₃, and

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

The hole transport region may include at least one compound selected from Compounds HT1 to HT39, but embodiments of the present disclosure are not limited thereto:

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A thickness of the hole transport region may be from about 100 Å to about 10,000 Å, for example, about 100 Å to about 3,000 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 thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

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

[p-Dopant]

The hole transport region may further include, 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, the p-dopant may have a LUMO energy level of −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 of the present disclosure 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 2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

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

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

a compound represented by Formula 221,

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

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, or a blue emission layer, according to a sub-pixel. In 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-emitting material, a green light-emitting material, and a blue light-emitting material, in which the two or more materials are mixed with each other in a single layer to emit white light.

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

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

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

[Host in Emission Layer]

In one or more embodiments, the host may include a compound represented by Formula 301 below:

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

In Formula 301,

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

xb11 may be 1, 2, or 3,

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

xb1 may be an integer from 0 to 5,

R₃₀₁may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5,

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), and

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

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 Formula 301-1 or 301-2:

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In Formulae 301-1 to 301-2,

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

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

R₃₁₁to R₃₁₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

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

L₃₀₁, xb1, R₃₀₁, and Q₃₁to Q₃₃may be understood by referring to corresponding description presented herein,

L₃₀₂to L₃₀₄may each independently be the same as defined in connection with L₃₀₁,

xb2 to xb4 may each independently be the same as defined in connection with xb1, and

R₃₀₂to R₃₀₄may each independently be the same as defined 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 croup, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁to Q₃₃are the same as described above.

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

Q₃₁to Q₃₃are the same as described above.

In one embodiment, the host may include an alkaline earth-metal complex. For example, the host may be selected from a Be complex (for example, Compound H55), a 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 embodiments of the present disclosure are not limited thereto:

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

The phosphorescent dopant may include the organometallic compound represented by Formula 1.

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

M(L₄₀₁)_xc1(L₄₀₂)_xc2 <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═*′, wherein Q₄₁₁and Q₄₁₂may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group,

X₄₀₆may be a single bond, O, or S,

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

xc11 and xc12 may each independently be an integer from 0 to 10, and

* 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 each be nitrogen at the same time.

In one or more embodiments, R₄₀₂and R₄₀₂in Formula 402 may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

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

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

a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; and

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

Q₄₀₁to Q₄₀₃may each independently be selected from a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, and a naphthyl group, but embodiments 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)-*′ (wherein Q₄₁₃and Q₄₁₄may each independently be hydrogen, deuterium, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group), but embodiments of the present disclosure are not limited thereto.

L₄₀₂in Formula 401 may be a monovalent, divalent, or trivalent organic ligand. For example, L₄₀₂may be 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 below:

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In Formula 501,

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

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

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

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

xd4 may be an integer from 1 to 6.

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

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

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

In one or more embodiments, xd4 in Formula 501 may be 2, 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 or more embodiments, 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.

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

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

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

Examples of the π electron-depleted nitrogen-containing ring include an imidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, an isoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, an indazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, a phthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline, a phenanthridine, an acridine, a phenanthroline, a phenazine, a benzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, a triazole, a tetrazole, an oxadiazole, a triazine, a thiadiazole, an imidazopyridine, an imidazopyrimidine, and an azacarbazole, 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, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

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

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

xe21 may be an integer from 1 to 5.

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

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, a naphthyridine group, a quinoxaline group, a quinazoline group, a cinnoline group, a phenanthridine group, an acridine group, a phenanthroline group, a phenazine group, a benzimidazole group, an isobenzothiazole group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a thiadiazole group, an imidazopyridine group, an imidazopyrimidine group, and an azacarbazole group; and

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

When xe11 in Formula 601 is 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), and X₆₁₆may be N or C(R₆₁₆), wherein at least one selected from X₆₁₄to X₆₁₆may be N,

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

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

R₆₁₁to R₆₁₃may each independently be the same as defined 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:

—S(═O)₂(Q₆₀₁) and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁and Q₆₀₂are the same as described above.

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

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In one or more embodiments, the electron transport region may include at least one selected from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-dphenyl-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 transport region may have excellent hole 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 range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

The electron transport region (for example, the electron transport layer in the electron transport region) may further include, 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 a Li ion, a Na ion, a K ion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex may include a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Sr ion, and a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may be selected from a hydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, a hydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyl oxazole, a hydroxy phenylthiazole, a hydroxy diphenyl oxadiazole, a hydroxy diphenylthiadiazole, 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.

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

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

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

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

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In 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 the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, such as Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF, KF, LiI, NaI, CsI, or KI. In 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 oxides, 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, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In 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, or the rare earth metal complex may be selected from hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline, hydroxy acridine, hydroxy phenanthridine, hydroxy phenyl oxazole, hydroxy phenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole, 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 an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any combinations thereof, as described above. In one or more embodiments, the electron injection layer may further include an organic material. When the electron injection layer further includes an organic material, an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal compound, an alkaline earth-metal compound, a rare earth metal compound, an alkali metal complex, an alkaline earth-metal complex, a rare earth metal complex, or any 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. When a thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without 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 which is an electron injection electrode, and in this regard, a material for forming the second electrode 190 may be selected from metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function.

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

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

[Description of FIGS. 2 to 4]

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 luminescence efficiency according to the principle of constructive interference.

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

At least one selected from the first capping layer 210 and the second capping layer 220 may each independently include at least one material selected from carbocyclic compounds, heterocyclic compounds, amine-based compounds, porphyrine 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.

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

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

[General Definition of Substituents]

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

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

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

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

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

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

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

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. 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” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group 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 fused to each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a carbocyclic aromatic system that has at least one heteroatom selected from N, O, Si, P, and S as a ring-forming atom, in addition to 1 to 60 carbon atoms. 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 with each other.

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

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

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

The term “C₅-C₆₀carbocyclic group” as used herein refers to a monocyclic or polycyclic group having 5 to 60 carbon atoms in which a ring-forming atom is a carbon atom only. The term “C₅-C₆₀carbocyclic group” as used herein refers to an aromatic carbocyclic group or a non-aromatic carbocyclic group. The C₅-C₆₀carbocyclic group may be a ring, such as benzene, a monovalent group, such as a phenyl group, or a divalent group, such as a phenylene group. In 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 C₅-C₆₀carbocyclic group, except that as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S is used in addition to carbon (the number of carbon atoms may be in a range of 1 to 60).

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

a 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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-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), and —B(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 amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-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), and —B(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), and

Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, a biphenyl group, and a terphenyl group.

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

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

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

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

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

SYNTHESIS EXAMPLE
Synthesis Example 1: Synthesis of Compound 1

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(1) Synthesis of Intermediate [1-A]

2,6-dibromo-4-(tert-butyl)pyridine (1.0 eq), carbazole (3.0 eq), Pd₂(dba)₃(0.2 eq), Sphos (0.4 eq), and K₃PO₄(2.0 eq) were dissolved in toluene (0.5 M) and stirred at a temperature of 120° C. for 12 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulphate and concentrated, and column chromatography was used to obtain Intermediate [1-A] (yield: 65%).

(2) Synthesis of Intermediate [1-B]

Intermediate [1-A] (1.0 eq) was dissolved in tetrahydrofuran (0.5 M), n-buthylithium (1.2 eq) was slowly added thereto while stirring at a temperature of −78° C., and the reaction mixture was stirred for 2 hours. 3-bromobenzaldehyde (1.2 eq) was slowly added thereto while stirring at a temperature of −78° C., and the reaction mixture was stirred at room temperature for 12 hours. An organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulphate and concentrated, and column chromatography was used to Intermediate [1-B] (yield: 42%).

(3) Synthesis of Intermediate [1-C]

Intermediate [1-B] (1.0 eq) and DDQ (2.0 eq) were dissolved in dichloromethane (0.5 M) and stirred at room temperature for 0.5 hours. An organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulphate and concentrated, and column chromatography was used to obtain Intermediate [1-C] (yield: 90%).

(4) Synthesis of Intermediate [1-D]

Magnesium turning (5.0 eq) was dissolved in tetrahydrofuran (0.5 M), and I₂(0.01 eq) was added thereto. 2-bromo biphenyl (1.2 eq) was slowly added thereto while stirring the reaction mixture at room temperature, and was stirred for 3 hours. After the reaction mixture was cooled to a temperature of −78° C., Intermediate [1-C] (0.1 eq) dissolved in tetrahydrofuran (0.5 M) was slowly added thereto while stirring the reaction mixture. The reaction mixture was heated to a temperature of 70° C. and stirred for 12 hours. An organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate and concentrated, and column chromatography was used to obtain Intermediate [1-D] (yield: 46%).

(5) Synthesis of Intermediate [1-E]

Intermediate [1-D] (1.0 eq) was dissolved in acetic acid (0.5 M) and 35% HCl aqueous solution (0.5 M) and stirred at a temperature of 120° C. for 12 hours. After the reaction mixture was cooled to room temperature, and pH was adjusted to 6 to 7 by using 3N NaOH aqueous solution. An organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate and concentrated, and column chromatography was used to obtain Intermediate [1-E] (yield: 55%).

(6) Synthesis of Intermediate [1-F]

Intermediate [1-E] (1.0 eq), imidazole (1.2 eq), CuI (0.01 eq), K₂CO₃(2.0 eq), and L-Proline (0.02 eq) were dissolved in dimethylsulfonate (0.1 M) and stirred at a temperature of 160° C. for 48 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate and concentrated, and column chromatography was used to obtain Intermediate [1-F] (yield: 43%).

(7) Synthesis of Intermediate [1-G]

Intermediate [1-F] (1.0 eq) and iodomethane (3.0 eq) were dissolved in THF (1.0 M) and stirred at a temperature of 70° C. for 12 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate and concentrated, and column chromatography was used to obtain Intermediate [1-G] (yield: 83%).

(8) Synthesis of Compound 1

Intermediate [1-G] (1.0 eq), dichloro(1,2-dicyclooctadiene)platinum (Pt(COD)Cl₂) (1.1 eq), and sodium acetate (2.0 eq) were dissolved in dioxane (0.1M) and stirred at a temperature of 120° C. for 72 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulfate and concentrated, and column chromatography was used to Compound 1 (yield: 22%).

Synthesis Example 2: Synthesis of Compound 2

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(1) Synthesis of Intermediate [2-A]

Intermediate [2-A] (yield: 41%) was synthesized in the same manner as in Synthesis of Intermediate [1-B], except that 2,6-dibromo-4-(tert-butyl)pyridine was used instead of Intermediate [1-A], and benzaldehyde was used instead of 3-bromobenzaldehyde.

(2) Synthesis of Intermediate [2-B]

Intermediate [2-B] (yield: 67%) was synthesized in the same manner as in Synthesis of Intermediate [1-C], except that Intermediate [2-A] was used instead of Intermediate [1-B].

(3) Synthesis of Intermediate [2-C]

Intermediate [2-C] (yield: 43%) was synthesized in the same manner as in Synthesis of Intermediate [1-D], except that Intermediate [2-B] was used instead of Intermediate [1-C].

(4) Synthesis of Intermediate [2-D]

Intermediate [2-D] (yield: 43%) was synthesized in the same manner as in Synthesis of Intermediate [1-E], except that Intermediate [2-C] was used instead of Intermediate [1-D].

(5) Synthesis of Intermediate [2-E]

Intermediate [2-E] (yield: 44%) was synthesized in the same manner as in Synthesis of Intermediate [1-B], except that Intermediate [2-D] was used instead of Intermediate [1-A].

(6) Synthesis of Intermediate [2-F]

Intermediate [2-F] (yield: 62%) was synthesized in the same manner as in Synthesis of Intermediate [1-C], except that Intermediate [2-E] was used instead of Intermediate [1-B].

(7) Synthesis of Intermediate [2-G]

Intermediate [2-G] (yield: 43%) was synthesized in the same manner as in Synthesis of Intermediate [1-D], except that Intermediate [2-F] was used instead of Intermediate [1-C].

(8) Synthesis of Intermediate [2-H]

Intermediate [2-H] (yield: 47%) was synthesized in the same manner as in Synthesis of Intermediate [1-E], except that Intermediate [2-G] was used instead of Intermediate [1-D].

(9) Synthesis of Intermediate [2-I]

Intermediate [2-I] (yield: 52%) was synthesized in the same manner as in Synthesis of Intermediate [1-F], except that Intermediate [2-H] was used instead of Intermediate [1-E].

(10) Synthesis of Intermediate [2-J]

Intermediate [2-J] (yield: 86%) was synthesized in the same manner as in Synthesis of Intermediate [1-G], except that Intermediate [2-I] was used instead of Intermediate [1-F].

(11) Synthesis of Compound 2

Compound 2 (yield: 24%) was synthesized in the same manner as in Synthesis of Compound 1, except that Intermediate [2-J] was used instead of Intermediate [1-G].

Synthesis Example 3: Synthesis of Compound 3

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(1) Synthesis of Intermediate [3-A]

Intermediate [3-A] (yield: 27%) was synthesized in the same manner as in Synthesis of Intermediate [1-B], except that Intermediate [2-D] was used instead of Intermediate [1-A], and 1-methyl-2-phenyl-1H-imidazole-4-carbaldehyde was used instead of 3-bromobenzaldehyde.

(2) Synthesis of Intermediate [3-B]

Intermediate [3-B] (yield: 62%) was synthesized in the same manner as in Synthesis of Intermediate [1-C], except that Intermediate [3-A] was used instead of Intermediate [1-B].

(3) Synthesis of Intermediate [3-C]

Intermediate [3-C] (yield: 51%) was synthesized in the same manner as in Synthesis of Intermediate [1-D], except that Intermediate [3-B] was used instead of Intermediate [1-C].

(4) Synthesis of Intermediate [3-D]

Intermediate [3-D] (yield: 45%) was synthesized in the same manner as in Synthesis of Intermediate [1-E], except that Intermediate [3-C] was used instead of Intermediate [1-D].

(5) Synthesis of Compound 3

Compound 3 (yield: 31%) was synthesized in the same manner as in Synthesis of Compound 1, except that Intermediate [3-D] was used instead of Intermediate [1-G].

Synthesis Example 4: Synthesis of Compound 4

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(1) Synthesis of Intermediate [4-A]

2,6-dibromo-4-(tert-butyl)pyridine (1.0 eq), phenol (1.2 eq), CuI (0.01 eq), K₂CO₃(2.0 eq), and L-Proline (0.02 eq) were dissolved in dimethylsulfonate (0.1 M) and stirred at a temperature of 160′ C. for 48 hours. After the reaction mixture was cooled to room temperature, an organic layer was extracted therefrom three times by using dichloromethane and water. The extracted organic layer was dried by using magnesium sulphate and concentrated, and column chromatography was used to obtain Intermediate [4-A] (yield: 57%).

(2) Synthesis of Intermediate [4-B]

Intermediate [4-B] (yield: 29%) was synthesized in the same manner as in Synthesis of Intermediate [1-B], except that Intermediate [4-A] was used instead of Intermediate [1-A].

(3) Synthesis of Intermediate [4-C]

Intermediate [4-C] (yield: 62%) was synthesized in the same manner as in Synthesis of Intermediate [1-C], except that Intermediate [4-B] was used instead of Intermediate [1-B].

(4) Synthesis of Intermediate [4-D]

Intermediate [4-D] (yield: 49%) was synthesized in the same manner as in Synthesis of Intermediate [1-D], except that Intermediate [4-C] was used instead of Intermediate [1-C].

(5) Synthesis of Intermediate [4-E]

Intermediate [4-E] (yield: 47%) was synthesized in the same manner as in Synthesis of Intermediate [1-E], except that Intermediate [4-D] was used instead of Intermediate [1-D].

(6) Synthesis of Intermediate [4-F]

Intermediate [4-F] (yield: 54%) was synthesized in the same manner as in Synthesis of Intermediate [1-F], except that Intermediate [4-E] was used instead of Intermediate [1-E].

(7) Synthesis of Intermediate [4-G]

Intermediate [4-G] (yield: 81%) was synthesized in the same manner as in Synthesis of Intermediate [1-G], except that Intermediate [4-F] was used instead of Intermediate [1-F].

(8) Synthesis of Compound 4

Compound 4 (yield: 27%) was synthesized in the same manner as in Synthesis of Compound 1, except that Intermediate [4-G] was used instead of Intermediate [1-G].

Synthesis Example 5: Synthesis of Compound 5

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(1) Synthesis of Intermediate [5-A]

Intermediate [5-A] (yield: 51%) was synthesized in the same manner as in Synthesis of Intermediate [4-A], except that Intermediate [2-D] (1.0 eq) was used instead of 2,6-dibromo-4-(tert-butyl)pyridine, and 3-bromophenol (1.2 eq) was used instead of phenol.

(2) Synthesis of Intermediate [5-B]

Intermediate [5-B] (yield: 52%) was synthesized in the same manner as in Synthesis of Intermediate [1-F], except that Intermediate [5-A] was used instead of Intermediate [1-E]

(3) Synthesis of Intermediate [5-C]

Intermediate [5-C] (yield: 77%) was synthesized in the same manner as in Synthesis of Intermediate [1-G], except that Intermediate [5-B] was used instead of Intermediate [1-F].

(4) Synthesis of Compound 5

Compound 5 (yield: 24%) was synthesized in the same manner as in Synthesis of Compound 1, except that Intermediate [5-C] was used instead of Intermediate [1-G].

¹H NMR and LC-MS of Compounds synthesized according to Synthesis Examples 1 to 5 are shown in Table 1.

Synthesis methods of compounds other than Compounds shown in Table 1 may also be easily recognized by those of ordinary skill in the art by referring to the synthesis mechanisms and source materials described above.

TABLE 1

Com-

pound

LC-MS

No.

¹H NMR (CDCl₃, 400 MHz)
found
calc.

1
8.65 (d, 1H), 8.55 (d, 1H), 8.15 (d, 1H), 7.90-
813.22
813.24

6.54 (m, 20H), 3.67 (s, 3H), 1.32 (s, 9H)

2
8.61 (d, 1H), 7.87-6.60 (m, 25H), 6.49 (d,
888.30
888.28

1H), 3.62 (s, 3H), 1.30 (s, 9H)

3
7.92-7.18 (m, 27H), 7.06 (s, 1H), 3.73 (s,
888.21
888.28

3H), 1.29 (s, 9H)

4
8.66 (d, 1H), 8.12-6.55 (m, 18H), 3.58 (s,
740.24
740.21

3H), 1.34 (s, 9H)

5
8.58 (d, 1H), 8.03-6.27 (m, 18H), 5.67 (s,
740.19
740.21

1H), 3.69 (s, 3H), 1.31 (s, 9H)

EVALUATION EXAMPLE

Quantum simulation was performed on i) A percentage of a triplet metal-to-ligand charge transfer state (³MLCT), ii) a simulation value (λ_max^sim) and an experiment value (λ_max^exp) of a wavelength of maximum emission, iii) an energy level of a triplet metal-centered state (³MC), and iv) bond dissociation energy of an N atom of pyridine (Py) in a ligand and a metal center Pt of Comparative Examples 1 to 5, and results thereof are shown in Table 2.

TABLE 2

ΔE_HOMO-LUMO

Pt—Py bond

(eV)
λ_max^sim(nm)
λ_max^exp(nm)

³MLCT (%)
dissociation energy (eV)

Comparative
2.66
465.8094
453
11.0
2.96

Compound 1

Comparative
1.73
714.005
—
—
—

Compound 2

Comparative
1.63
756.637
—
—
—

Compound 3

Comparative
2.59
478.1594
480
14.8
3.18

Compound 4

Comparatve
2.34
529.0396
515
15.1
3.01

Compound 5

Compound 1
2.23
555.13
543
16.2
3.21

Compound 2
2.22
557.64
546
17.6
3.27

Compound 3
2.64
468.5062
458
17.1
3.10

Compound 4
2.51
493.5235
479
15.7
3.07

Compound 5
2.93
422.5108
431
15.4
3.04

<Comparative Compound 1>

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<Comparative Compound 2>

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<Comparative Compound 3>

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<Comparative Compound 4>

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<Comparative Compound 5>

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EXAMPLE
Example 1

As an anode, a Corning 15 Ω/cm²(1,200 Å) ITO glass substrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated with isopropyl alcohol and pure water each for 5 minutes, and then cleaned by exposure to ultraviolet rays and ozone for 30 minutes. Then, the ITO glass substrate was provided to a vacuum deposition apparatus. 2-TNATA was vacuum-deposited on the ITO glass substrate to form a hole injection layer having a thickness of 600 Å, and 4,4′-bis[N-(1-naphthyl)-N-phenylaminobiphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 Å. Compound 1 (dopant) (weight ratio of 10%) and 3,3-di(9H-carbazol-9-yl)biphenyl (mCBP) (host) were co-deposited on the hole transport layer to form an emission layer having a thickness of 300 Å. Then, diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was vacuum-deposited on the emission layer to form a hole blocking layer having a thickness of 50 Å. Then, Alq₃was deposited on the hole blocking layer to form an electron transport layer having thickness of 300 Å, an alkali metal halide 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 to a thickness 3,000 Å (cathode electrode) to form an LiF/Al electrode, thereby completing the manufacture of an organic light-emitting device.

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Examples 2 to 5

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds 2 to 5 were each used instead of Compound 1 as a dopant in forming an emission layer.

Comparative Examples 1 to 3

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Comparative Compounds 1, 4, and 5 were each used instead of Compound 1 as a dopant in forming an emission layer.

The driving voltage, luminance, luminescence efficiency, and maximum emission efficiency of the organic light-emitting devices manufactured according to Examples 1 to 5 and Comparative Examples 1 to 3 were measured at a current density of 50 mA/cm²by using Keithley SMU 236 and a luminance meter PR650, and an amount of time (lifespan) that lapsed when luminance was 50% of initial luminance (100%) was measured. Results thereof are shown in Table 3.

TABLE 3

Wavelength

of

Driving
Current

maximum

voltage
density
Luminance
Efficiency
emission
Emission

Emission layer
(V)
(mA/cm²)
(cd/m²)
(cd/A)
(nm)
color

Example
Compound 1
5.16
50
5351
10.7
543
Green

1

Example
Compound 2
5.07
50
5603
11.2
546
Green

2

Example
Compound 3
5.48
50
4033
8.07
458
Blue

3

Example
Compound 4
5.24
50
4272
8.54
479
Blue

4

Example
Compound 5
5.62
50
3995
7.99
431
Blue

5

Comparative
Comparative
5.45
50
3910
7.82
453
Blue

Example
Compound 1

1

Comparative
Comparative
6.85
50
3860
7.72
480
Blue

Example
Compound 4

2

Comparative
Comparative
5.22
50
4556
9.11
515
Green

Example
Compound 5

3

From Table 3, it is confirmed that the green organic light-emitting devices of Examples 1 and 2, in which the compounds according to one or more embodiments are used in an emission layer as a dopant, have an improved driving voltage and increased luminescence efficiency, as compared with the green organic light-emitting device of Comparative Example 3.

It is confirmed that the blue organic light-emitting devices of Examples 3 to 5, in which the compounds according to one or more embodiments are used in an emission layer as a dopant, have improved luminescence efficiency, as compared with the blue organic light-emitting device of Comparative Example 1, and have a low driving voltage and high luminescence efficiency, as compared with the blue organic light-emitting device of Comparative Example 2.

That is, when the compounds according to one or more embodiments are used in the organic light-emitting device, high color purity may be implemented, and a suitable effect may be exhibited in terms of driving voltage and efficiency.

The organic light-emitting device including the organometallic compound may have a low driving voltage, high efficiency, a long lifespan, and high color purity.

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.

ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

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