ORGANOMETALLIC COMPOUND, LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND ELECTRONIC APPARATUS INCLUDING LIGHT-EMITTING DEVICE

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2021-0030364, filed on Mar. 8, 2021, in the Korean Intellectual Property Office, the entire content of which is hereby incorporated by reference.

BACKGROUND
1. Field

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

2. Description of the Related Art

Light-emitting devices are self-emissive devices that have wide viewing angles, high contrast ratios, short response times, and/or suitable (e.g., excellent) characteristics in terms of brightness, driving voltage, and/or response speed.

Light-emitting devices may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked 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 transition from an excited state to a ground state to thereby generate light.

SUMMARY

Aspects according to one or more embodiments are directed toward an organometallic compound and a light-emitting device including the organometallic compound.

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 of the disclosure.

According to one or more embodiments, an organometallic compound may be represented by Formula 1.

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In Formula 1,

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

Y₁to Y₄may each independently be N or C,

A₁to A₅may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

B₁to B₄may each independently be a chemical bond, O, or S,

L₁to L₃may each independently be a single bond, *—O—*′, *—S—*′, *—C(R₆)(R₇)—*′, *—C(R₆)═*′, *═C(R₇)—*′, *—C(R₆)═C(R₇)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₆)—*′, *—N(R₆)—*′, *—P(R₆)*′, *—Si(R₆)(R₇)—*′, *—P(R₆)(R₇)—*′, or *—Ge(R₆)(R₇)—*′,

a1 to a3 may each independently be an integer from 1 to 3,

V₁may be a single bond, O, S, C(R₈₁)(R₈₂), or Si(R₈₁)(R₈₂),

R₁to R₇, R₈₁, and R₈₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

R₁and R₆of L₁, R₂and R₆of L₁and/or L₂, R₃and R₆of L₂and/or L₃, and R₄and R₅may optionally be bound to each other to form a substituted or unsubstituted C₃-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group,

R₃and R₅may be separated from each other without bonding to each other,

b1 to b5 may each independently be an integer from 1 to 10, and

R_10amay be

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group,

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof,

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof, or

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

wherein Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, or a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

According to one or more embodiments, a light-emitting device may include a first electrode, a second electrode facing the first electrode, an interlayer 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

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

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

FIG. 2 is a schematic cross-sectional view of an electronic apparatus according to an embodiment; and

FIG. 3 is a schematic cross-sectional view of an electronic apparatus according to another embodiment.

DETAILED DESCRIPTION

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

An organometallic compound may be represented by Formula 1:

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

In an embodiment, M₁may be Pt, Pd, Cu, Ag, or Au. For example, M₁may be Pt, but embodiments are not limited thereto.

In Formula 1, Y₁to Y₄may each independently be N or C.

In an embodiment, in Formula 1,

Y₁to Y₃may each be C, and Y₄may be N,

Y₁, Y₂, and Y₄may each be C, and Y₃may be N,

Y₁, Y₃, and Y₄may each be C, and Y₂may be N,

Y₂to Y₄may each be C, and Y₁may be N,

Y₁and Y₄may each be C, and Y₂and Y₃may each be N,

Y₁and Y₄may each be N, and Y₂and Y₃may each be C,

Y₁and Y₂may each be C, and Y₃and Y₄may each be N,

Y₁and Y₂may each be N, and Y₃and Y₄may each be C,

Y₁and Y₃may each be C, and Y₂and Y₄may each be N, or

Y₁and Y₃may each be N, and Y₂and Y₄may each be C.

In some embodiments, Y₁to Y₃may each be C, and Y₄may be N.

In an embodiment, Y₁may be C and may be a carbon atom of a carbene moiety.

In Formula 1, A₁to A₅may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group.

In some embodiments, A₁to A₅may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a carbene moiety-containing 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 isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a 2,3-dihydrobenzimidazole group, an imidazopyridine group, a 2,3-dihydroimidazopyridine group, an imidazopyrimidine group, a 2,3-dihydroimidazopyrimidine group, 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, or a 5,6,7,8-tetrahydroquinoline group.

In an embodiment, at least one of A₁to A₃may be a carbene moiety-containing group. For example, at least one of A₁to A₃may be an imidazole group including a carbene moiety or a benzimidazole group including a carbene moiety.

In some embodiments, A₁may be a group represented by one of Formulae A1-1 to A1-15,

A₂may be a group represented by one of Formulae A2-1 to A2-11, and

A₃may be a group represented by one of Formulae A3-1 to A3-11:

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wherein, in Formulae A1-1 to A1-15, A2-1 to A2-11, and A3-1 to A3-11,

Y₁to Y₃may respectively be defined by referring to the descriptions of Y₁to Y₃provided herein,

Z₁₁to Z₁₈, Z₂₁to Z₂₇, and Z₃₁to Z₃₇may each independently be C or N,

Z₁₉, Z₂₈, and Z₃₈may each independently be O, S, C, or Si,

* indicates a binding site to M, and

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

In some embodiments, in Formula 1, A₁may be a group represented by Formula A1-14 or A1-15.

In an embodiment, in Formula 1, Y₄may be N, and A₄may be a pyridine group.

In an embodiment, a moiety represented by

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in Formula 1 may be represented by one of Formulae A4-1 to A4-20:

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wherein, in Formulae A4-1 to A4-20,

R₄₁to R₄₃may each be defined by the description of R₄provided herein,

R₅₁to R₅₄may each be defined by the description of R₅provided herein,

R₈₁and R₈₂may respectively be defined by the descriptions of R₈₁and R₈₂provided herein (in connection with Formula 1), and

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

In Formula 1, B₁to B₄may each independently be a chemical bond, O, or S.

The chemical bond may be a covalent bond or a coordinate bond.

In an embodiment, in Formula 1, B₁to B₄may each be a chemical bond,

B₁may be O or S, and B₂to B₄may each be a chemical bond,

B₂may be O or S, and B₁, B₃, and B₄may each be a chemical bond,

B₃may be O or S, and B₁, B₂, and B₄may each be a chemical bond, or

B₄may be O or S, and B₁, B₂, and B₃may each be a chemical bond.

In some embodiments, in Formula 1,

a bond between Y₁and B₁or a bond between Y₁and M₁may be a coordinate bond,

a bond between Y₂and B₂or a bond between Y₂and M₁may be a covalent bond,

a bond between Y₃and B₃or a bond between Y₃and M₁may be a covalent bond, and

a bond between Y₄and B₄or a bond between Y₄and M₁may be a coordinate bond.

In an embodiment, B₁to B₄may each be a chemical bond, and B₁and B₄may each be a coordinate bond, and B₂and B₃may each be a covalent bond.

In an embodiment, Y₁may be C, and B₁may be a coordinate bond.

In one or more embodiments, Y₁to Y₃may each be C, Y₄may be N, B₁and B₄may each be a coordinate bond, and B₂and B₃may each be covalent bond.

In Formula 1, L₁to L₃may each independently be a single bond, *—O—*′, *—S—*′, *—C(R₆)(R₇)—*′, *—C(R₆)═*′, *═C(R₇)—*′, *—C(R₆)═C(R₇)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₆)—*′, *—N(R₆)—*′, *—P(R₆)—*′, *—Si(R₆)(R₇)—*′, *—P(R₆)(R₇)—*′, or *—Ge(R₆)(R₇)—*′.

In some embodiments, L₁to L₃may each independently be a single bond, *—O—*′, *—S—*′, *—C(R₆)(R₇)—*′, *—B(R₆)—*′, *—N(R₆)—*′, *—Si(R₆)(R₇)—*′, or *—P(R₆)(R₇)—*′.

In an embodiment, L₁and L₃may each be a single bond.

In an embodiment, L₂may be *—O—*′, *—S—*′, or *—C(R₆)(R₇)—*′.

For example, L₁and L₃may each be a single bond, and L₂may be *—O—*′, but embodiments are not limited thereto.

In Formula 1, a1 to a3 may each independently be an integer from 1 to 3. For example, a1 to a3 may each be 1.

a1 indicates the number of L₁(s), and when a1 is 2 or greater, two or more L₁(s) may be identical to or different from each other. a2 indicates the number of L₂(s), and when a2 is 2 or greater, two or more L₂(s) may be identical to or different from each other. a3 indicates the number of L₃(s), and when a3 is 2 or greater, two or more L₃(s) may be identical to or different from each other.

In an embodiment, L₁and L₃may each be a single bond, and L₂may be *—O—*′, *—S—*′, or *—C(R₆)(R₇)—*′, and a1 to a3 may each be 1.

In Formula 1, V₁may be a single bond, O, S, C(R₈₁)(R₈₂), or Si(R₈₁)(R₈₂).

In Formula 1, R₁to R₇, R₈₁, and R₈₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂).

R₁and R₆, R₂and R₆, R₃and R₆(e.g., R₁and R₆of L₁, R₂and R₆of L₁and/or L₂, R₃and R₆of L₂and/or L₃), and R₄and R₅may optionally be bound to each other to form a substituted or unsubstituted C₃-C₆₀carbocyclic group or a substituted or unsubstituted C₁-C₆₀heterocyclic group, and R₃and R₅may be separated from each other without bonding to each other.

In some embodiments, R₃and R₅may not be bound to each other to form a cyclic group and may be separated, and a ligand of the organometallic compound may not include a condensed ring including both A₃and A₅.

In some embodiments, R₁to R₇, R₈₁, and R₈₂may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, or a C₁-C₂₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, 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 perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, or an indolocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, 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 perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, an indolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), or —B(Q₁)(Q₂),

wherein Q₁to Q₃and Q₃₁to Q₃₃may each independently be: a C₁-C₂₀alkyl group; a C₁-C₂₀alkoxy group; or a C₃-C₂₀carbocyclic group or a C₁-C₂₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

In one or more embodiments, R₁to R₇, R₈₁, and R₈₂may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, or a cyano group;

a C₁-C₂₀alkyl group or a C₁-C₂₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a cyano group, a phenyl group, a naphthyl group, a biphenyl group, a terphenyl group, or any combination thereof;

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, or a triazinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CF₃, a cyano 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 phenanthrenyl group, an anthracenyl group, a pyridinyl group, a pyrimidinyl group, a carbazolyl group, a triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), or any combination thereof; or

—Si(Q₁)(Q₂)(Q₃),

In some embodiments, R₁to R₇, R₈₁, and R₈₂may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, a cyano group, —CF₃, —CCl₃, —CBr₃, —Cl₃, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group;

a phenyl group, a biphenyl group, a terphenyl group, or a pyridinyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CF₃, a cyano group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), or any combination thereof; or

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁to Q₃and Q₃₁to Q₃₃may each independently be a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, or a terphenyl group.

In an embodiment, at least one of R₁to R₄may be:

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), or —B(Q₁)(Q₂),

In some embodiments, at least one of R₁to R₄may be a group represented by Formula 6-1 or 6-2, or —Si(Q₁)(Q₂)(Q₃):

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wherein, in Formulae 6-1 and 6-2,

Z₇₁and Z₇₂may each independently be a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl 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, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), or —B(Q₃₁)(Q₃₂),

Z₇₃to Z₇₇may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a phenyl group, a naphthyl group, a fluorenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), or —B(Q₃₁)(Q₃₂), and

k1 and k2 may each independently be an integer from 1 to 5,

wherein Q₁to Q₃and Q₃₃to Q₃₃may each independently be a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, or a terphenyl group, and

* indicates a binding site to an adjacent atom.

In some embodiments, at least one of R₁to R₄may be a group represented by one of Formulae 7-1 to 7-37, or —Si(Q₁)(Q₂)(Q₃), wherein Q₁to Q₃may each independently be a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, or a terphenyl group, but embodiments are not limited thereto:

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wherein, in Formulae 7-1 to 7-37,

“i-Pr” represents an iso-propyl group, “t-Bu” represents a tert-butyl group, “TMS” represents a trimethylsilyl group, and “Ph” represents a phenyl group, and

* indicates a binding site to an adjacent atom.

In Formula 1, b1 to b5 may each independently be an integer from 1 to 10.

b1 indicates the number of R₁(s), and when b1 is 2 or greater, two or more R₁(s) may be identical to or different from each other. b2 indicates the number of R₂(s), and when b2 is 2 or greater, two or more R₂(s) may be identical to or different from each other. b3 indicates the number of R₃(s), and when b3 is 2 or greater, two or more R₃(s) may be identical to or different from each other. b4 indicates the number of R₄(s), and when b4 is 2 or greater, two or more R₄(s) may be identical to or different from each other. b5 indicates the number of R₅(s), and when b5 is 2 or greater, two or more R₅(s) may be identical to or different from each other.

In some embodiments, an organometallic compound may be represented by Formula 1A or Formula 1B:

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wherein, in Formulae 1A and 1B,

A₂to A₅, Y₂to Y₄, B₁to B₄, L₁to L₃, a1 to a3, V₁, R₂to R₅, and b2 to b5 may respectively be defined by referring to the descriptions of A₂to A₅, Y₂to Y₄, B₁to B₄, L₁to L₃, a1 to a3, V₁, R₂to R₅, and b2 to b5 provided herein (e.g., in connection with Formula 1),

X₁₁may be C(R₁₁) or N, X₁₂may be C(R₁₂) or N, X₁₃may be C(R₁₃) or N, and X₁₄may be C(R₁₄) or N, and

R₁₁to R₁₅may each be defined by referring to the description of R₁provided herein (e.g., in connection with Formula 1).

In an embodiment, in Formulae 1A and 1B, R₁₅may be deuterium, —F, —Cl, —Br, —I, a cyano group, —CF₃, —CCl₃, —CBr₃, —Cl₃, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a group represented by one of Formulae 7-1 to 7-37.

In an embodiment, the organometallic compound may be represented by one selected from the group consisting of Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4:

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wherein, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4,

M₁, L₂, R₈₁, and R₈₂may respectively be defined by referring to the descriptions of M₁, L₂, R₈₁, and R₈₂provided herein (e.g., in connection with Formula 1),

X₁₁may be C(R₁₁) or N, X₁₂may be C(R₁₂) or N, X₁₃may be C(R₁₃) or N, and X₁₄may be C(R₁₄) or N,

X₃₁may be C(R₃₁) or N, X₃₂may be C(R₃₂) or N, and X₃₃may be C(R₃₃) or N,

R₁₁to R₁₅may each be defined by referring to the description of R₁provided herein (e.g., in connection with Formula 1),

R₂₁to R₂₃may each be defined by referring to the description of R₂provided herein (e.g., in connection with Formula 1),

R₃₁to R₃₃may each be defined by referring to the description of R₃provided herein (e.g., in connection with Formula 1),

R₄₁to R₄₃may each be defined by referring to the description of R₄provided herein (e.g., in connection with Formula 1), and

R₅₁to R₅₄may each be defined by referring to the description of R₅provided herein (e.g., in connection with Formula 1).

In an embodiment, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4, at least one of R₁₁to R₁₅, R₂₁to R₂₃, R₃₁to R₃₃, or R₄₁to R₄₃may be:

—Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), or —B(Q₁)(Q₂),

For example, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4, at least one of R₁₁to R₁₅, R₂₁to R₂₃, R₃₁to R₃₃, or R₄₁to R₄₃may be a group represented by one of Formulae 7-1 to 7-37 or —Si(Q₁)(Q₂)(Q₃), wherein Q₁to Q₃may each independently be a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, or a terphenyl group.

In an embodiment, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4, R₁₅may be deuterium, —F, —Cl, —Br, —I, a cyano group, —CF₃, —CCl₃, —CBr₃, —Cl₃, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, or a group represented by one of Formulae 7-1 to 7-37.

In some embodiments, in Formulae 1A-1 to 1A-4 and 1B-1 to 1B-4,

i) X₃₁may be C(R₃₁), X₃₂may be C(R₃₂), and X₃₃may be C(R₃₃),

ii) X₃₁may be C(R₃₁), X₃₂may be C(R₃₂), and X₃₃may be N,

iii) X₃₁may be C(R₃₁), X₃₂may be N, and X₃₃may be C(R₃₃), or

iv) X₃₁may be N, X₃₂may be C(R₃₂), and X₃₃may be C(R₃₃).

In an embodiment, the organometallic compound may be one of Compounds BD1 to BD20, but embodiments are not limited thereto:

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In Compounds BD1 to BD20, “d₅” represents substitution with 5 deuterium atoms (D). The organometallic compound represented by Formula 1 may include a

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moiety in which ring A₄is condensed to an adjacent *—N(A₅)-*′ group via a linking group V₁. Accordingly, the organometallic compound may have an increased structural rigidity, and thus, a bonding energy between ring A₄and a metal center M₁may increase. Therefore, the organometallic compound may have improved overall molecular stability. For example, when ring A₄is a pyridine, because the pyridine is condensed to the *—N(A₅)-*′ group adjacent to the pyridine, the bonding energy around the pyridine may increase, and accordingly, a bond between a ligand of the organometallic compound and the metal center may be prevented or substantially prevented from breaking. Accordingly, the organometallic compound may have suitable (e.g., excellent) stability, and thus, an electronic device, e.g., a light-emitting device, including the organometallic compound may have suitable (e.g., excellent) luminescence efficiency and improved lifespan.

R₃and R₅in the organometallic compound represented by Formula 1 may be separated from each other without bonding to each other. Therefore, a ligand of the organometallic compound may not include a condensed ring including both A₃and A₅. For example, when R₃is condensed to R₅to form a ring, the planarity of the organometallic complex may increase, and thus, intermolecular interaction between dopants or between dopants and hosts may increase. Therefore, the full width at half maximum (FWHM) of the photoluminescence spectrum of the organometallic compound may increase, and the photoluminescence spectrum may be red-shifted, which is an adverse effect. In the organometallic compound according to one or more embodiments, R₃and R₅may be separated from each other. Accordingly, the FWHM of the photoluminescence spectrum of the organometallic compound may be narrow. In addition, the organometallic compound according to one or more embodiments may emit light in a shorter wavelength region, thereby improving color reproducibility of blue light.

In an embodiment, at least one of R₁to R₅in the organometallic compound may include a bulky group that may induce steric hindrance. Due to the bulky substituent, the rotational motion and/or vibrational motion of the organometallic compound may be suppressed to thereby prevent or substantially prevent decomposition of the ligand-metal center. In addition, when the organometallic compound is applied to a light-emitting device, red shift due to formation of excimers may be suppressed, thus allowing high color purity to be realized, and lifespan characteristics may be improved.

As the organometallic compound represented by Formula 1 may have a high triplet metal-centered state (³MC state) energy, rapid transition from an excited state to a ground state may occur without energy loss. Thus, a light-emitting device including the organometallic compound may have high efficiency and long lifespan characteristics.

The organometallic compound represented by Formula 1 may have a small bond angle around the C—N bond (the C—N1 bond below) of the supporting moiety because of an enhanced binding force between the pyridine and the metal, and three bonds bound to the pyridine. Due to the less distorted geometrical structure, the bond dissociation energy of the organometallic compound may increase.

In one embodiment, at least one of rings A₁to A₃in the organometallic compound represented by Formula 1 may a include a ring having a carbene carbon as a coordination atom. For example, at least one of rings A₁to A₃may be an imidazole group or a benzimidazole group including a carbene carbon as a coordination atom. The binding force between the carbene carbon and the metal may be greater than the binding force between nitrogen and the metal, and as d-d* transition is suppressed by the strong electron donor of the carbene carbon, the organometallic compound may be optically and/or electrically stable, and prevent or substantially prevent non-radiative transition. Accordingly, when the organometallic compound is applied to a light-emitting device, the light-emitting device may have long lifespan and high efficiency.

The highest occupied molecular orbital (HOMO) energy level and lowest unoccupied molecular orbital (LUMO) energy level of each of the compounds were measured according to differential pulse voltammetry (DPV). The triplet (T₁) energy level, presence rate of triplet metal-to-ligand charge transfer state (³MLCT), triplet metal-centered state (³MC) energy level, and bond dissociation energy of the carbon-nitrogen bond (the C—N1, C—N2, and C—N3 bonds) were evaluated by simulation utilizing the density functional theory (DFT) method of the Gaussian program structurally optimized with the B3LYP/6-31 G(d,p). The results thereof are shown in Table 1.

TABLE 1

T₁
T₁
MLCT

³MC
BDE (Kcal/mol)

HOMO (eV)
LUMO (eV)
(nm)
(eV)
(%)
(eV)
C-N1
C-N2
C-N3

C1
−4.94
−1.58
484
2.64
9.15
0.42
22.8
28.2
27.2

L-11
−5.00
−1.79
495
2.50
10.13
0.35
20.9
29.5
25.5

L-12
−5.12
−1.95
534
2.32
12.50
0.22
20.8
26.5
24.3

L-21
−5.02
−1.49
466
2.66
12.61
0.65
22.4
30.2
25.1

1
−5.08
−1.86
479
2.59
11.46
0.72
36.3
28.9
27.2

2
−5.20
−2.11
455
2.73
14.30
0.69
35.3
29.9
27.0

3
−5.25
−2.13
447
2.77
12.22
0.65
30.4
27.8
25.6

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A method of synthesizing the organometallic compound represented by Formula 1 may be apparent to one of ordinary skill in the art by referring to Synthesis Examples provided herein.

The organometallic compound represented by Formula 1 may be utilized in a light-emitting device (e.g., an organic light-emitting device). According to one or more embodiments, a light-emitting device may include: a first electrode; a second electrode facing the first electrode; an interlayer between the first electrode and the second electrode and including an emission layer and at least one organometallic compound represented by Formula 1.

In some embodiments,

the first electrode of the light-emitting device may be an anode,

the second electrode of the light-emitting device may be a cathode,

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

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

The electron transport region may include a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and/or an electron injection layer.

In an embodiment, the interlayer may include the organometallic compound. In some embodiments, the organometallic compound may be included in a capping layer, which is disposed on outer sides of a pair of electrodes in a light-emitting device.

In an embodiment, the emission layer in the interlayer may include the organometallic compound. For example, the emission layer may include a host and a dopant, and the organometallic compound included in the emission layer may serve as a dopant. A content of the organometallic compound in the emission layer may be in a range of about 0.1 parts to about 49.99 (e.g., 49.9 or less than 50) parts by weight, based on 100 parts by weight of the emission layer.

For example, the host may be a carbazole-containing compound.

In an embodiment, the emission layer may include the organometallic compound, and blue light having a maximum emission wavelength in a range of about 430 nm to about 490 nm, for example, about 445 nm to about 465 nm, may be emitted from the emission layer.

In an embodiment, the electron transport region in the interlayer may include a phosphine oxide-containing compound.

In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside a first electrode (e.g., on the side facing oppositely away from a second electrode) or a second capping layer located outside a second electrode (e.g., on the side facing oppositely away from the first electrode), and at least one of the first capping layer or the second capping layer may include the organometallic compound represented by Formula 1. The first capping layer and the second capping layer may respectively be understood by referring to the descriptions of the first capping layer and the second capping layer provided herein.

In some embodiments, the light-emitting device may include:

a first capping layer located outside the first electrode and including the organometallic compound represented by Formula 1;

a second capping layer located outside the second electrode and including the organometallic compound represented by Formula 1; or

the first capping layer and the second capping layer.

The expression that an “(interlayer and/or a capping layer) includes at least one organometallic compound” as used herein may be construed as referring to that the “(interlayer and/or the capping layer) may include one organometallic compound of Formula 1 or two different organometallic compounds of Formula 1”.

For example, the interlayer and/or the capping layer may include only Compound BD1 as the organometallic compound. In this embodiment, Compound BD1 may be included in the emission layer of the light-emitting device. In some embodiments, both Compounds BD1 and BD2 may be included in the interlayer as organometallic compounds. In this embodiment, Compounds BD1 and BD2 may be included in the same layer (for example, both Compounds BD1 and BD2 may be included in an emission layer) or in different layers (for example, Compound BD1 may be included in an emission layer, and Compound BD2 may be included in an electron transport region).

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

According to one or more embodiments, an electronic apparatus may include the light-emitting device. The electronic apparatus may further include a thin-film transistor. In some embodiments, the electronic apparatus may further include a thin-film transistor including a source electrode and a drain electrode, and a first electrode of the light-emitting device may be electrically connected to the source electrode or the drain electrode. The electronic apparatus may further include a color filter, a color-conversion layer, a touchscreen layer, a polarization layer, or any combination thereof. The electronic apparatus may be defined by referring to the description of the electronic apparatus provided herein.

Description of FIG. 1

FIG. 1 is a schematic cross-sectional view of a light-emitting device 10 according to an embodiment. The light-emitting device 10 may include a first electrode 110, an interlayer 130, and a second electrode 150.

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

First Electrode 110

In FIG. 1, a substrate may be additionally located under the first electrode 110 or above the second electrode 150. The substrate may be a glass substrate or a plastic substrate. The substrate may be a flexible substrate including plastic having suitable (e.g., excellent) heat resistance and durability, for example, polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

The first electrode 110 may be formed by depositing or sputtering, on the substrate, a material for forming the first electrode 110. When the first electrode 110 is an anode, a high work function material that may easily inject holes may be utilized as a material for a first electrode.

The first electrode 110 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. When the first electrode 110 is a transmissive electrode, a material for forming the first electrode 110 may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), or any combinations thereof. In some embodiments, when the first electrode 110 is a semi-transmissive electrode or a reflective electrode, magnesium (Mg), silver (Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), or any combination thereof may be utilized as a material for forming the first electrode 110.

The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including two or more layers. In some embodiments, the first electrode 110 may have a triple-layered structure of ITO/Ag/ITO.

Interlayer 130

The interlayer 130 may be on the first electrode 110. The interlayer 130 may include an emission layer.

The interlayer 130 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 150.

The interlayer 130 may further include one or more metal-containing compounds such as one or more organometallic compounds, inorganic materials such as quantum dots, and/or the like, in addition to various suitable organic materials.

The interlayer 130 may include: i) two or more emitting units sequentially stacked between the first electrode 110 and the second electrode 150; and ii) a charge generation layer located between the two adjacent emitting units. When the interlayer 130 includes the two or more emitting units and the charge generation layer, the light-emitting device 10 may be a tandem light-emitting device.

Hole Transport Region in Interlayer 130

The hole transport region may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of 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 a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.

For example, the hole transport region may have a multi-layered structure, e.g., a hole injection layer/hole transport layer structure, a hole injection layer/hole transport layer/emission auxiliary layer structure, a hole injection layer/emission auxiliary layer structure, a hole transport layer/emission auxiliary layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, wherein constituting layers of each structure are sequentially stacked on the first electrode 110 in the respective stated order.

The hole transport region may include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof:

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wherein, in Formulae 201 and 202,

L₂₀₁to L₂₀₄may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

L₂₀₅may be *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a C₁-C₂₀alkylene group unsubstituted or substituted with at least one R_10a, a C₂-C₂₀alkenylene group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xa1 to xa4 may each independently be an integer from 0 to 5,

xa5 may be an integer from 1 to 10,

R₂₀₁to R₂₀₄and Q₂₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

R₂₀₁and R₂₀₂may optionally be bound to each other via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10ato form a C₈-C₆₀polycyclic group (e.g., a carbazole group and/or the like) unsubstituted or substituted with at least one R_10a(e.g., Compound HT16 described herein),

R₂₀₃and R₂₀₄may optionally be bound to each other via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R_10a, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10ato form a C₈-C₆₀polycyclic group unsubstituted or substituted with at least one R_10a, and

na1 may be an integer from 1 to 4.

In some embodiments, Formulae 201 and 202 may each include at least one of the groups represented by Formulae CY201 to CY217:

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wherein, in Formulae CY201 to CY217, R_10band R_10cmay each independently be defined by referring to the descriptions of R_10a, ring CY₂₀₁to ring CY₂₀₄may each independently be a C₃-C₂₀carbocyclic group or a C₁-C₂₀heterocyclic group, and at least one hydrogen in Formulae CY201 to CY217 may be unsubstituted or substituted with R_10a.

In some embodiments, in Formulae CY201 to CY217, ring CY₂₀₁to ring CY₂₀₄may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

In one or more embodiments, Formulae 201 and 202 may each include at least one of the groups represented by Formulae CY201 to CY203.

In one or more embodiments, Formula 201 may include at least one of the groups represented by Formulae CY201 to CY203 and at least one of the groups represented by Formulae CY204 to CY217.

In one or more embodiments, in Formula 201, xa1 may be 1, R₂₀₁may be a group represented by any one of Formulae CY201 to CY203, xa2 may be 0, and R₂₀₂may be a group represented by one of Formulae CY204 to CY207.

In one or more embodiments, each of Formulae 201 and 202 may not include any of the groups represented by Formulae CY201 to CY203.

In one or more embodiments, each of Formulae 201 and 202 may not include any of the groups represented by Formulae CY201 to CY203, and may include at least one of the groups represented by Formulae CY204 to CY217.

In one or more embodiments, each of Formulae 201 and 202 may not include any of the groups represented by Formulae CY201 to CY217.

In some embodiments, the hole transport region may include one of Compounds HT1 to HT46, 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/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:

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The thickness of the hole transport region may be in a range of about 50 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 4,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, or any combination thereof, the thickness of the hole injection layer may be in a range of about 100 Å to about 9,000 Å, for example, about 100 Å to about 1,000 Å, the thickness of the hole transport layer may be in a range of about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within any of these ranges, suitable (e.g., excellent) hole transport characteristics may be obtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. The electron blocking layer may prevent or reduce the flow (e.g., leakage) of electrons from the emission layer to a hole transport region. Materials that may be included in the hole transport region may also be included in an emission auxiliary layer and an electron blocking layer.

p-Dopant

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

The charge generating material may include, for example, a p-dopant.

In some embodiments, a lowest unoccupied molecular orbital (LUMO) energy level of the p-dopant may be −3.5 eV or less.

In some embodiments, the p-dopant may include a quinone derivative, a compound containing a cyano group, a compound containing element EL1 and element EL2 (to be described in more detail below), or any combination thereof.

Examples of the quinone derivative may include TCNQ, F4-TCNQ, and/or the like.

Examples of the compound containing a cyano group include HAT-CN, a compound represented by Formula 221, and/or the like:

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wherein, in Formula 221,

R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, and

at least one of R₂₂₁to R₂₂₃may each independently be: a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each substituted with a cyano group; —F; —Cl; —Br; —I; a C₁-C₂₀alkyl group substituted with a cyano group, —F, —Cl, —Br, —I, or any combination thereof; or any combination thereof.

In the compound containing element EL1 and element EL2, element EL1 may be a metal, a metalloid, or a combination thereof, and element EL2 may be a non-metal, a metalloid, or a combination thereof.

Examples of the metal may include: an alkali metal (e.g., lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and/or the like); an alkaline earth metal (e.g., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and/or the like); a transition metal (e.g., titanium (Ti), zirconium (Zr), hafnium (Hf), vanadium (V), niobium (Nb), tantalum (Ta), chromium (Cr), molybdenum (Mo), tungsten (W), manganese (Mn), technetium (Tc), rhenium (Re), iron (Fe), ruthenium (Ru), osmium (Os), cobalt (Co), rhodium (Rh), iridium (Ir), nickel (Ni), palladium (Pd), platinum (Pt), copper (Cu), silver (Ag), gold (Au), and/or the like); a post-transition metal (e.g., zinc (Zn), indium (In), tin (Sn), and/or the like); a lanthanide metal (e.g., lanthanum (La), cerium (Ce), praseodymium (Pr), neodymium (Nd), promethium (Pm), samarium (Sm), europium (Eu), gadolinium (Gd), terbium (Tb), dysprosium (Dy), holmium (Ho), erbium (Er), thulium (Tm), ytterbium (Yb), lutetium (Lu), and/or the like); and/or the like.

Examples of the metalloid may include silicon (Si), antimony (Sb), tellurium (Te), and/or the like.

Examples of the non-metal may include oxygen (O), halogen (e.g., F, Cl, Br, I, and/or the like), and/or the like.

For example, the compound containing element EL1 and element EL2 may include a metal oxide, a metal halide (e.g., a metal fluoride, a metal chloride, a metal bromide, a metal iodide, and/or the like), a metalloid halide (e.g., a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, and/or the like), a metal telluride, or any combination thereof.

Examples of the metal oxide may include tungsten oxide (e.g., WO, W₂O₃, WO₂, WO₃, W₂O₅, and/or the like), vanadium oxide (e.g., VO, V₂O₃, VO₂, V₂O₅, and/or the like), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, and/or the like), rhenium oxide (e.g., ReO₃and/or the like), and/or the like.

Examples of the metal halide may include an alkali metal halide, an alkaline earth metal halide, a transition metal halide, a post-transition metal halide, a lanthanide metal halide, and/or the like.

Examples of the alkali metal halide may include LiF, NaF, KF, RbF, CsF, LiCl, NaCl, KCl, RbCl, CsCl, LiBr, NaBr, KBr, RbBr, CsBr, LiI, NaI, KI, RbI, CsI, and/or the like.

Examples of the alkaline earth metal halide may include BeF₂, MgF₂, CaF₂, SrF₂, BaF₂, BeCl₂, MgCl₂, CaCl₂, SrCl₂, BaCl₂, BeBr₂, MgBr₂, CaBr₂, SrBr₂, BaBr₂, BeI₂, MgI₂, CaI₂, SrI₂, BaI₂, and/or the like.

Examples of the transition metal halide may include titanium halide (e.g., TiF₄, TiCl₄, TiBr₄, TiI₄, and/or the like), zirconium halide (e.g., ZrF₄, ZrCl₄, ZrBr₄, ZrI₄, and/or the like), hafnium halide (e.g., HfF₄, HfCl₄, HfBr₄, HfI₄, and/or the like), vanadium halide (e.g., VF₃, VCl₃, VBr₃, VI₃, and/or the like), niobium halide (e.g., NbF₃, NbCl₃, NbBr₃, NbI₃, and/or the like), tantalum halide (e.g., TaF₃, TaCl₃, TaBr₃, TaI₃, and/or the like), chromium halide (e.g., CrF₃, CrCl₃, CrBr₃, CrI₃, and/or the like), molybdenum halide (e.g., MoF₃, MoCl₃, MoBr₃, MoI₃, and/or the like), tungsten halide (e.g., WF₃, WCl₃, WBr₃, WI₃, and/or the like), manganese halide (e.g., MnF₂, MnCl₂, MnBr₂, MnI₂, and/or the like), technetium halide (e.g., TcF₂, TcCl₂, TcBr₂, TcI₂, and/or the like), rhenium halide (e.g., ReF₂, ReCl₂, ReBr₂, ReI₂, and/or the like), iron halide (e.g., FeF₂, FeCl₂, FeBr₂, FeI₂, and/or the like), ruthenium halide (e.g., RuF₂, RuCl₂, RuBr₂, RuI₂, and/or the like), osmium halide (e.g., OsF₂, OsCl₂, OsBr₂, OsI₂, and/or the like), cobalt halide (e.g., CoF₂, CoCl₂, CoBr₂, CoI₂, and/or the like), rhodium halide (e.g., RhF₂, RhCl₂, RhBr₂, RhI₂, and/or the like), iridium halide (e.g., IrF₂, IrCl₂, IrBr₂, IrI₂, and/or the like), nickel halide (e.g., NiF₂, NiCl₂, NiBr₂, NiI₂, and/or the like), palladium halide (e.g., PdF₂, PdCl₂, PdBr₂, PdI₂, and/or the like), platinum halide (e.g., PtF₂, PtCl₂, PtBr₂, PtI₂, and/or the like), copper halide (e.g., CuF, CuCl, CuBr, CuI, and/or the like), silver halide (e.g., AgF, AgCl, AgBr, AgI, and/or the like), gold halide (e.g., AuF, AuCl, AuBr, AuI, and/or the like), and/or the like.

Examples of the post-transition metal halide may include zinc halide (e.g., ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, and/or the like), indium halide (e.g., InI₃and/or the like), tin halide (e.g., SnI₂and/or the like), and/or the like.

Examples of the lanthanide metal halide may include YbF, YbF₂, YbF₃, SmF₃, YbCl, YbCl₂, YbCl₃, SmCl₃, YbBr, YbBr₂, YbBr₃, SmBr₃, YbI, YbI₂, YbI₃, SmI₃, and/or the like.

Examples of the metalloid halide may include antimony halide (e.g., SbCl₅and/or the like) and/or the like.

Examples of the metal telluride may include alkali metal telluride (e.g., Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te, and/or the like), alkaline earth metal telluride (e.g., BeTe, MgTe, CaTe, SrTe, BaTe, and/or the like), transition metal telluride (e.g., TiTe₂, ZrTe₂, HfTe₂, V₂Te₃, Nb₂Te₃, Ta₂Te₃, Cr₂Te₃, Mo₂Te₃, W₂Te₃, MnTe, TcTe, ReTe, FeTe, RuTe, OsTe, CoTe, RhTe, IrTe, NiTe, PdTe, PtTe, Cu₂Te, CuTe, Ag₂Te, AgTe, Au₂Te, and/or the like), post-transition metal telluride (e.g., ZnTe and/or the like), lanthanide metal telluride (e.g., LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, and/or the like), and/or the like.

Emission Layer in Interlayer 130

When the light-emitting device 10 is a full color light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and/or a blue emission layer, according to a sub-pixel. In one or more embodiments, the emission layer may have a stacked structure. The stacked structure may include two or more layers selected from a red emission layer, a green emission layer, and a blue emission layer. The two or more layers may be in direct contact with each other. In some embodiments, the two or more layers may be separated from each other. In one or more embodiments, the emission layer may include two or more materials. The two or more materials may include a red light-emitting material, a green light-emitting material, and/or a blue light-emitting material. The two or more materials may be mixed with each other in a single layer. The two or more materials mixed with each other in the single layer may emit white light.

The emission layer may include a host and a dopant. The dopant may be a phosphorescent dopant, a fluorescent dopant, or any combination thereof.

The amount of the dopant in the emission layer may be in a range of about 0.01 parts to about 15 parts by weight based on 100 parts by weight of the host.

In some embodiments, the emission layer may include a quantum dot.

The emission layer may include a delayed fluorescence material. The delayed fluorescence material may serve as a host or a dopant in the emission layer.

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

Host

The host may include a compound represented by Formula 301:

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

wherein, in Formula 301,

Ar₃₀₁and L₃₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xb11 may be 1, 2, or 3,

xb1 may be an integer from 0 to 5,

R₃₀₁may be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂), —B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), or —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁to Q₃₀₃may each independently be defined by referring to the description of Q₁provided herein.

In some embodiments, when xb11 in Formula 301 is 2 or greater, at least two Ar₃₀₁(s) may be bound via a single bond.

In some embodiments, the host may include a compound represented by Formula 301-1, a compound represented by Formula 301-2, or any combination thereof:

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wherein, in Formulae 301-1 and 301-2,

ring A₃₀₁to ring A₃₀₄may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

X₃₀₁may be O, S, N-[(L₃₀₄)_xb4-R₃₀₄], C(R₃₀₄)(R₃₀₅), or Si(R₃₀₄)(R₃₀₅),

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

L₃₀₁, xb1, and R₃₀₁may respectively be defined by referring to the descriptions of L₃₀₁, xb1, and R₃₀₁provided herein,

L₃₀₂to L₃₀₄may each independently be defined by referring to the description of L₃₀₁provided herein,

xb2 to xb4 may each independently be defined by referring to the description of xb1 provided herein, and

R₃₀₂to R₃₀₅and R₃₁₁to R₃₁₄may each independently be defined by referring to the description of R₃₀₁provided herein.

In some embodiments, the host may include an alkaline earth-metal complex, a post-transitional metal complex, or any combination thereof. For example, the host may include a Be complex (e.g., Compound H55), a Mg complex, a Zn complex, or any combination thereof.

In some embodiments, the host may include one of Compounds H1 to H124, 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), or any combination thereof:

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Phosphorescent Dopant

The emission layer may include the organometallic compound represented by Formula 1 described herein as a phosphorescent dopant.

Fluorescent Dopant

The fluorescent dopant may include an amine group-containing compound, a styryl group-containing compound, or any combination thereof.

In some embodiments, the fluorescent dopant may include a compound represented by Formula 501:

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wherein, in Formula 501,

Ar₅₀₁, L₅₀₁to L₅₀₃, R₅₀₁, and R₅₀₂may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xd1 to xd3 may each independently be 0, 1, 2, or 3, and

xd4 may be 1, 2, 3, 4, 5, or 6.

In some embodiments, in Formula 501, Ar₅₀₁may include a condensed ring group (e.g., an anthracene group, a chrysene group, or a pyrene group) in which at least three monocyclic groups are condensed together.

In some embodiments, xd4 in Formula 501 may be 2.

In some embodiments, the fluorescent dopant may include one of Compounds FD1 to FD36, DPVBi, DPAVBi, or any combination thereof:

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Delayed Fluorescence Material

The emission layer may include a delayed fluorescence material.

The delayed fluorescence material described herein may be any suitable compound that may emit delayed fluorescence according to a delayed fluorescence emission mechanism.

The delayed fluorescence material included in the emission layer may serve as a host or a dopant, depending on kind (e.g., type) of other materials included in the emission layer.

In some embodiments, a difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material may be about 0 eV or greater and about 0.5 eV or less. When the difference between a triplet energy level (eV) of the delayed fluorescence material and a singlet energy level (eV) of the delayed fluorescence material is within this range, up-conversion from a triplet state to a singlet state in the delayed fluorescence material may occur effectively, thereby improving the luminescence efficiency and/or the like of the light-emitting device 10.

In some embodiments, the delayed fluorescence material may include: i) a material including at least one electron donor (e.g., a π electron-rich C₃-C₆₀cyclic group such as a carbazole group and/or the like) and at least one electron acceptor (e.g., a sulfoxide group, a cyano group, a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group, and/or the like), and/or ii) a material including a C₈-C₆₀polycyclic group including at least two cyclic groups condensed to each other and sharing boron (B), and/or the like.

Examples of the delayed fluorescence material may include at least one of Compounds DF1 to DF9:

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Quantum Dots

The emission layer may include quantum dots.

The term “quantum dot” as used herein refers to a crystal of a semiconductor compound and may include any suitable material capable of emitting light of various suitable wavelengths according to the size of the crystal.

The diameter of the quantum dot may be, for example, in a range of about 1 nm to about 10 nm.

The quantum dots may be synthesized by a wet chemical process, an organic metal (e.g., organometallic) chemical vapor deposition process, a molecular beam epitaxy process, or any similar process.

The wet chemical process is a method of growing a quantum dot crystal particle by mixing a precursor material with an organic solvent. When the crystal grows, the organic solvent may naturally serve as a dispersant coordinated on the surface of the quantum dot crystal and control the growth of the crystal. Thus, the wet chemical method may be easier to perform than the vapor deposition process such a metal organic chemical vapor deposition (MOCVD) or a molecular beam epitaxy (MBE) process. Further, the growth of quantum dot particles may be controlled with a lower manufacturing cost.

The quantum dot may include a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element or compound; or any combination thereof.

Examples of the group II-VI semiconductor compound may include a binary compound such as CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnO, HgS, HgSe, HgTe, MgSe, and/or MgS; a ternary compound such as CdSeS, CdSeTe, CdSTe, ZnSeS, ZnSeTe, ZnSTe, HgSeS, HgSeTe, HgSTe, CdZnS, CdZnSe, CdZnTe, CdHgS, CdHgSe, CdHgTe, HgZnS, HgZnSe, HgZnTe, MgZnSe, and/or MgZnS; a quaternary compound such as CdZnSeS, CdZnSeTe, CdZnSTe, CdHgSeS, CdHgSeTe, CdHgSTe, HgZnSeS, HgZnSeTe, and/or HgZnSTe; or any combination thereof.

Examples of the group III-V semiconductor compound may include a binary compound such as GaN, GaP, GaAs, GaSb, AlN, AlP, AlAs, AlSb, InN, InP, InAs, and/or InSb; a ternary compound such as GaNP, GaNAs, GaNSb, GaPAs, GaPSb, AlNP, AlNAs, AlNSb, AlPAs, AlPSb, InGaP, InNP, InAlP, InNAs, InNSb, InPAs, and/or InPSb; a quaternary compound such as GaAlNP, GaAlNAs, GaAlNSb, GaAlPAs, GaAlPSb, GaInNP, GaInNAs, GaInNSb, GaInPAs, GaInPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; or any combination thereof. In some embodiments, the group III-V semiconductor compound may further include a group II element. Examples of the group III-V semiconductor compound further including the group II element may include InZnP, InGaZnP, InAlZnP, and/or the like.

Examples of the group III-VI semiconductor compound may include a binary compound such as GaS, GaSe, Ga₂Se₃, GaTe, InS, InSe, In₂S₃, In₂Se₃, InTe, and/or the like; a ternary compound such as InGaS₃, InGaSe₃, and/or the like; or any combination thereof.

Examples of the group I-III-VI semiconductor compound may include a ternary compound such as AgInS, AgInS₂, CuInS, CuInS₂, CuGaO₂, AgGaO₂, AgAlO₂, or any combination thereof.

Examples of the group IV-VI semiconductor compound may include a binary compound such as SnS, SnSe, SnTe, PbS, PbSe, and/or PbTe; a ternary compound such as SnSeS, SnSeTe, SnSTe, PbSeS, PbSeTe, PbSTe, SnPbS, SnPbSe, and/or SnPbTe; a quaternary compound such as SnPbSSe, SnPbSeTe, and/or SnPbSTe; or any combination thereof.

The group IV element or compound may be a single element material such as Si and/or Ge; a binary compound such as SiC and/or SiGe; or any combination thereof.

Individual elements included in the multi-element compound, such as a binary compound, a ternary compound, and/or a quaternary compound, may be present in a particle thereof at a uniform or non-uniform concentration.

The quantum dot may have a single structure in which the concentration of each element included in the quantum dot is uniform or a core-shell double structure. In some embodiments, in a quantum dot with a core-shell structure, materials included in the core may be different from materials included in the shell.

The shell of the quantum dot may serve as a protective layer for preventing or reducing chemical denaturation of the core to maintain semiconductor characteristics and/or as a charging layer for imparting electrophoretic characteristics to the quantum dot. The shell may have a monolayer or a multilayer structure. An interface between a core and a shell may have a concentration gradient where a concentration of elements present in the shell decreases toward the core.

Examples of the shell of the quantum dot may include a metal oxide, a metalloid oxide, a nonmetal oxide, a semiconductor compound, or a combination thereof. Examples of the metal oxide, the metalloid oxide, or the nonmetal oxide may include: a binary compound such as SiO₂, Al₂O₃, TiO₂, ZnO, MnO, Mn₂O₃, Mn₃O₄, CuO, FeO, Fe₂O₃, Fe₃O₄, CoO, Co₃O₄, and/or NiO; a ternary compound such as MgAl₂O₄, CoFe₂O₄, NiFe₂O₄, and/or CoMn₂O₄; and any combination thereof. Examples of the semiconductor compound may include a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; or any combination thereof. In some embodiments, the semiconductor compound may be CdS, CdSe, CdTe, ZnS, ZnSe, ZnTe, ZnSeS, ZnTeS, GaAs, GaP, GaSb, HgS, HgSe, HgTe, InAs, InP, InGaP, InSb, AlAs, AlP, AlSb, or any combination thereof.

The quantum dot may have a full width at half maximum (FWHM) of an emission wavelength spectrum of about 45 nm or less, about 40 nm or less, or about 30 nm or less. When the FWHM of the quantum dot is within these ranges, color purity or color reproducibility may be improved. In addition, because light emitted through the quantum dot is emitted in all directions, an optical viewing angle may be improved.

In addition, the quantum dot may be, for example, a spherical, pyramidal, multi-arm, or cubic nanoparticle, a nanotube, a nanowire, a nanofiber, or a nanoplate particle.

By adjusting the size of the quantum dot, the energy band gap may also be adjusted, thereby obtaining light of various suitable wavelengths in the quantum dot emission layer. By utilizing quantum dots of various suitable sizes, a light-emitting device that may emit light of various suitable wavelengths may be realized. In some embodiments, the size of the quantum dot may be selected such that the quantum dot may emit red, green, and/or blue light. In addition, the size of the quantum dot may be selected such that the quantum dot may emit white light by combining light of various suitable light colors.

Electron Transport Region in Interlayer 130

The electron transport region may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of 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 a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, and/or an electron injection layer.

In some embodiments, 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 constituting layers of each structure are sequentially stacked on the emission layer in the respective stated order.

The electron transport region (e.g., a buffer layer, a hole blocking layer, an electron control layer, and/or an electron transport layer in the electron transport region) may include a metal-free compound including at least one π electron-deficient nitrogen-containing C₁-C₆₀cyclic group.

In some embodiments, the electron transport region may include a compound represented by Formula 601:

[Ar₆₀₁]_xe11-[(L₆₀₁)_xe1-R₆₀₁]_xe21 Formula 601

wherein, in Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xe11 may be 1, 2, or 3,

xe1 may be 0, 1, 2, 3, 4, or 5,

R₆₀₁may be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be defined by referring to the description of Q₁provided herein,

xe21 may be 1, 2, 3, 4, or 5, and

at least one of Ar₆₀₁, L₆₀₁, or R₆₀₁may each independently be a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group unsubstituted or substituted with at least one R_10a.

In some embodiments, when xe11 in Formula 601 is 2 or greater, two or more Ar₆₀₁(s) may be bound to each other via a single bond.

In some embodiments, in Formula 601, Ar₆₀₁may be a substituted or unsubstituted anthracene group.

In some embodiments, the electron transport region may include a compound represented by Formula 601-1:

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wherein, in Formula 601-1,

X₆₁₄may be N or C(R₆₁₄), X₆₁₅may be N or C(R₆₁₅), X₆₁₆may be N or C(R₆₁₆), and at least one selected from X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may each independently be defined by referring to the description of L₆₀₁provided herein,

xe611 to xe613 may each independently be defined by referring to the description of xe1 provided herein,

R₆₁₁to R₆₁₃may each independently be defined by referring to the description of R₆₀₁provided herein, and

R₆₁₄to R₆₁₆may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a.

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

The electron transport region may include one of Compounds ET1 to ET45, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAlq, TAZ, NTAZ, or any combination thereof:

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The thickness of the electron transport region may be in a range of about 100 Angstroms (Å) to about 5,000 Å, for example, about 160 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are each within these ranges, suitable (e.g., excellent) electron transport characteristics may be obtained without a substantial increase in driving voltage.

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

The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, or a cesium (Cs) ion. A metal ion of the alkaline earth metal complex may be a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, or a barium (Ba) ion. Each ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may independently be a hydroxyquinoline, a hydroxyisoquinoline, a hydroxybenzoquinoline, a hydroxyacridine, a hydroxyphenanthridine, a hydroxyphenyloxazole, a hydroxyphenylthiazole, a hydroxyphenyloxadiazole, a hydroxyphenylthiadiazole, a hydroxyphenylpyridine, a hydroxyphenylbenzimidazole, a hydroxyphenylbenzothiazole, a bipyridine, a phenanthroline, a cyclopentadiene, or any combination thereof.

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

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The electron transport region may include an electron injection layer that facilitates the injection of electrons from the second electrode 150. The electron injection layer may be in direct contact with the second electrode 150.

The electron injection layer may have i) a single-layered structure consisting of a single layer consisting of a single material, ii) a single-layered structure consisting of 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-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof.

The alkali metal may be Li, Na, K, Rb, Cs or any combination thereof. The alkaline earth metal may be Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may be Sc, Y, Ce, Tb, Yb, Gd, or any combination thereof.

The alkali metal-containing compound, the alkaline earth metal-containing compound, and the rare earth metal-containing compound may respectively be one or more oxides, halides (e.g., fluorides, chlorides, bromides, or iodides), tellurides, or any combination thereof of each of the alkali metal, the alkaline earth metal, and the rare earth metal.

The alkali metal-containing compound may be one or more alkali metal oxides such as Li₂O, Cs₂O, and/or K₂O, alkali metal halides such as LiF, NaF, CsF, KF, LiI, NaI, CsI, and/or KI, or any combination thereof. The alkaline earth-metal-containing compound (e.g., oxide) may include one or more alkaline earth-metal oxides, such as BaO, SrO, CaO, Ba_xSr_1-xO (wherein x is a real number satisfying 0<x<1), and/or Ba_xCa_1-xO (wherein x is a real number satisfying 0<x<1). The rare earth metal-containing compound may include YbF₃, ScF₃, Sc₂O₃, Y₂O₃, Ce₂O₃, GdF₃, TbF₃, YbI₃, ScI₃, TbI₃, or any combination thereof. In some embodiments, the rare earth metal-containing compound may include a lanthanide metal telluride. Examples of the lanthanide metal telluride may include LaTe, CeTe, PrTe, NdTe, PmTe, SmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, La₂Te₃, Ce₂Te₃, Pr₂Te₃, Nd₂Te₃, Pm₂Te₃, Sm₂Te₃, Eu₂Te₃, Gd₂Te₃, Tb₂Te₃, Dy₂Te₃, Ho₂Te₃, Er₂Te₃, Tm₂Te₃, Yb₂Te₃, Lu₂Te₃, and/or the like.

The alkali metal complex, the alkaline earth metal complex, and the rare earth metal complex may include: i) one of ions of the alkali metal, the alkaline earth metal, and the rare earth metal described above, and ii) a ligand bond to the metal ion, e.g., hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

The electron injection layer may include (e.g., consist of) an alkali metal, an alkaline earth metal, a rare earth metal, an alkali metal-containing compound, an alkaline earth metal-containing compound, a rare earth metal-containing compound, an alkali metal complex, an alkaline earth metal complex, a rare earth metal complex, or any combination thereof, as described above. In some embodiments, the electron injection layer may further include an organic material (e.g., a compound represented by Formula 601).

In some embodiments, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (e.g., an alkali metal halide), or ii) a) an alkali metal-containing compound (e.g., an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. In some embodiments, the electron injection layer may be a KI:Yb co-deposition layer, a RbI:Yb co-deposition layer, and/or the like.

When the electron injection layer further includes an organic material, the alkali metal, the alkaline earth metal, the rare earth metal, the alkali metal-containing compound, the alkaline earth metal-containing compound, the rare earth metal-containing compound, the alkali metal complex, the alkaline earth metal complex, the rare earth metal complex, or any combination thereof may be homogeneously or non-homogeneously dispersed in a matrix including the organic material.

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

Second Electrode 150

The second electrode 150 may be on the interlayer 130. In an embodiment, the second electrode 150 may be a cathode, which is an electron injection electrode. In this embodiment, a material for forming the second electrode 150 may be a material having a low work function, for example, a metal, an alloy, an electrically conductive compound, or any combination thereof.

The second electrode 150 may include lithium (Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), ytterbium (Yb), silver-ytterbium (Ag—Yb), ITO, IZO, or any combination thereof. The second electrode 150 may be a transmissive electrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 150 may have a single-layered structure, or a multi-layered structure including two or more layers.

Capping Layer

A first capping layer may be located outside the first electrode (e.g., on the side facing oppositely away from the second electrode) 110, and/or a second capping layer may be located outside the second electrode (e.g., on the side facing oppositely away from the first electrode) 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.

In the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the first electrode 110 (which may be a semi-transmissive electrode or a transmissive electrode) and through the first capping layer to the outside. In the light-emitting device 10, light emitted from the emission layer in the interlayer 130 may pass through the second electrode 150 (which may be a semi-transmissive electrode or a transmissive electrode) and through the second capping layer to the outside.

The first capping layer and the second capping layer may improve the external luminescence efficiency based on the principle of constructive interference. Accordingly, the optical extraction efficiency of the light-emitting device 10 may be increased, thus improving the luminescence efficiency of the light-emitting device 10.

The first capping layer and the second capping layer may each include a material having a refractive index of 1.6 or higher (at 589 nm).

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

At least one of the first capping layer or the second capping layer may each independently include one or more carbocyclic compounds, one or more heterocyclic compounds, one or more amine group-containing compounds, one or more porphine derivatives, one or more phthalocyanine derivatives, one or more naphthalocyanine derivatives, one or more alkali metal complexes, one or more alkaline earth metal complexes, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and/or the amine group-containing compound may optionally be substituted with O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In some embodiments, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.

In some embodiments, at least one of the first capping layer or the second capping layer may each independently include the compound represented by Formula 201, the compound represented by Formula 202, or any combination thereof.

In one or more embodiments, at least one of the first capping layer or the second capping layer may each independently include one of Compounds HT28 to HT33, one of Compounds CP1 to CP6, β-NPB, or any combination thereof:

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Film

The organometallic compound represented by Formula 1 may be included in various suitable films. According to one or more embodiments, a film includes the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or, a light-controlling member) (e.g., a color filter, a color-conversion member, a capping layer, a light extraction efficiency improvement layer, a selective light-absorbing layer, a polarization layer, a quantum dot-containing layer, and/or the like), a light-blocking member (e.g., a light reflection layer and/or a light-absorbing layer), or a protection member (e.g., an insulating layer and/or a dielectric material layer).

Electronic Apparatus

The light-emitting device may be included in various suitable electronic apparatuses. In some embodiments, an electronic apparatus including the light-emitting device may be an emission apparatus (e.g., a light-emitting apparatus) and/or an authentication apparatus.

The electronic apparatus (e.g., an emission apparatus) may further include, in addition to the light-emitting device, i) a color filter, ii) a color-conversion layer, or iii) a color filter and a color-conversion layer. The color filter and/or the color-conversion layer may be disposed on at least one traveling direction of light emitted from the light-emitting device. For example, light emitted from the light-emitting device may be blue light or white light. The light-emitting device may be defined by referring to the descriptions provided herein. In some embodiments, the color-conversion layer may include quantum dots. The quantum dot (e.g., each quantum dot) may be, for example, the quantum dot described herein.

The electronic apparatus may include a first substrate. The first substrate may include a plurality of sub-pixel areas, the color filter may include a plurality of color filter areas respectively corresponding to the plurality of sub-pixel areas, and the color-conversion layer may include a plurality of color-conversion areas respectively corresponding to the plurality of sub-pixel areas.

A pixel-defining film may be located among the plurality of sub-pixel areas to define each sub-pixel area.

The color filter may further include a plurality of color filter areas and light-blocking patterns between the plurality of color filter areas, and the color-conversion layer may further include a plurality of color-conversion areas and light-blocking patterns between the plurality of color-conversion areas.

The plurality of color filter areas (or the plurality of color-conversion areas) may include: a first area emitting a first color light; a second area emitting a second color light; and/or a third area emitting a third color light, and the first color light, the second color light, and/or the third color light may have different maximum emission wavelengths. In some embodiments, the first color light may be red light, the second color light may be green light, and the third color light may be blue light. In some embodiments, the plurality of color filter areas (or the plurality of color-conversion areas) may each include quantum dots. In some embodiments, the first area may include red quantum dots (e.g., red-light emitting quantum dots), the second area may include green quantum dots (e.g., green-light emitting quantum dots), and the third area may not include a quantum dot. The quantum dot may be defined by referring to the description of the quantum dot provided herein. The first area, the second area, and/or the third area may each further include an emitter.

In some embodiments, the light-emitting device may emit a first light, the first area may absorb the first light to emit a 1-1 color light, the second area may absorb the first light to emit a 2-1 color light, and the third area may absorb the first light to emit a 3-1 color light. In this embodiment, the 1-1 color light, the 2-1 color light, and the 3-1 color light may each have a different maximum emission wavelength. In some embodiments, the first light may be blue light, the 1-1 color light may be red light, the 2-1 color light may be green light, and the 3-1 light may be blue light.

The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein the source electrode or the drain electrode (e.g., the drain electrode) may be electrically connected to the first electrode or the second electrode of the light-emitting device (e.g., the first electrode).

The thin-film transistor may further include a gate electrode, a gate insulating film, and/or the like.

The active layer may include a crystalline silicon, an amorphous silicon, an organic semiconductor, and/or an oxide semiconductor.

The electronic apparatus may further include an encapsulation unit for sealing the light-emitting device. The encapsulation unit may be located between the color filter and/or the color-conversion layer and the light-emitting device. The encapsulation unit may allow light to pass to the outside from the light-emitting device and prevent or substantially prevent the air and/or moisture to permeate to the light-emitting device at the same time. The encapsulation unit may be a sealing substrate including transparent glass or a plastic substrate. The encapsulation unit may be a thin-film encapsulating layer including at least one of an organic layer or an inorganic layer. When the encapsulation unit is a thin-film encapsulating layer, the electronic apparatus may be flexible.

In addition to the color filter and/or the color-conversion layer, various suitable functional layers may be disposed on the encapsulation unit depending on the usage of an electronic apparatus. Examples of the functional layer may include a touch screen layer, a polarization layer, and/or the like. The touch screen layer may be a resistive touch screen layer, a capacitive touch screen layer, or an infrared beam touch screen layer. The authentication apparatus may be, for example, a biometric authentication apparatus that identifies an individual according to biometric information (e.g., a fingertip, a pupil, and/or the like).

The authentication apparatus may further include a biometric information collecting unit, in addition to the light-emitting device described above.

The electronic apparatus may be applicable to various suitable displays, an optical source, a lighting (e.g., an lighting apparatus), a personal computer (e.g., a mobile personal computer), a cellphone (e.g., mobile phone), a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, and/or an endoscope display device), a fish finder, various suitable measurement devices, gauges (e.g., gauges of an automobile, an airplane, and/or a ship), and/or a projector.

Descriptions of FIGS. 2 and 3

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

An emission apparatus in FIG. 2 may include a substrate 100, a thin-film transistor, a light-emitting device, and an encapsulation unit 300 sealing the light-emitting device.

The substrate 100 may be a flexible substrate, a glass substrate, or a metal substrate. A buffer layer 210 may be on the substrate 100. The buffer layer 210 may prevent or reduce penetration of impurities through the substrate 100 and may provide a flat surface on the substrate 100.

A thin-film transistor may be on the buffer layer 210. The thin-film transistor may include an active layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The active layer 220 may include an inorganic semiconductor such as silicon and/or polysilicon, an organic semiconductor, and/or an oxide semiconductor, and may include a source area, a drain area, and a channel area.

A gate insulating film 230 for insulating the active layer 220 from the gate electrode 240 may be on the active layer 220, and the gate electrode 240 may be on the gate insulating film 230.

An interlayer insulating film 250 may be on the gate electrode 240. The interlayer insulating film 250 may be between the gate electrode 240 and the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to provide insulation therebetween.

The source electrode 260 and the drain electrode 270 may be on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source area and the drain area of the active layer 220, and the source electrode 260 and the drain electrode 270 may be adjacent to (e.g., connected to) the exposed source area and the exposed drain area of the active layer 220.

Such a thin-film transistor may be electrically connected to a light-emitting device to drive the light-emitting device and may be protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or a combination thereof. A light-emitting device may be on the passivation layer 280. The light-emitting device may include a first electrode 110, an interlayer 130, and a second electrode 150.

The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not fully cover the drain electrode 270 and may expose a specific area of the drain electrode 270, and the first electrode 110 may be disposed to connect to the exposed area of the drain electrode 270.

A pixel-defining film 290 may be on the first electrode 110. The pixel-defining film 290 may expose a specific area of the first electrode 110, and the interlayer 130 may be formed in the exposed area of the first electrode 110. The pixel-defining film 290 may be a polyimide or polyacryl organic film. In some embodiments, some higher layers (e.g., one or more upper layers) of the interlayer 130 may extend to the upper portion of the pixel-defining film 290 and may be disposed in the form of a common layer.

The second electrode 150 may be on the interlayer 130, and a capping layer 170 may be additionally formed on the second electrode 150. The capping layer 170 may be formed to cover the second electrode 150.

The encapsulation unit 300 may be on the capping layer 170. The encapsulation unit 300 may be on the light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation unit 300 may include: an inorganic film including silicon nitride (SiN_x), silicon oxide (SiO_x), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxy methylene, poly aryllate (or polyacrylate), hexamethyl disiloxane, an acrylic resin (e.g., polymethyl methacrylate, polyacrylic acid, and/or the like), an epoxy resin (e.g., aliphatic glycidyl ether (AGE) and/or the like), or any combination thereof; or a combination of the inorganic film and the organic film.

FIG. 3 is a schematic cross-sectional view of another light-emitting apparatus according to an embodiment.

The emission apparatus shown in FIG. 3 may be substantially identical to the emission apparatus shown in FIG. 2, except that a light-shielding pattern 500 and a functional area 400 are additionally located on the encapsulation unit 300. The functional area 400 may be i) a color filter area, ii) a color-conversion area, or iii) a combination of a color filter area and a color-conversion area. In some embodiments, the light-emitting device included in the emission apparatus shown in FIG. 3 may be a tandem light-emitting device.

Manufacturing Method

The layers constituting the hole transport region, the emission layer, and the layers constituting the electron transport region may be formed in a specific region by utilizing one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, ink-jet printing, laser printing, and/or laser-induced thermal imaging.

When layers constituting the hole transport region, the emission layer, and layers constituting the electron transport region are each independently formed by vacuum-deposition, the vacuum-deposition may be performed at a deposition temperature in a range of about 100° C. to about 500° C., at a vacuum degree in a range of about 10⁻⁸torr to about 10⁻³torr, and at a deposition rate in a range of about 0.01 Angstroms per second (Å/sec) to about 100 Å/sec, depending on the material to be included in each layer and the structure of each layer to be formed.

General Definitions of Terms

The term “C₃-C₆₀carbocyclic group” as used herein refers to a cyclic group consisting of only 3 to 60 carbon atoms as ring-forming atoms. The term “C₁-C₆₀heterocyclic group” as used herein refers to a cyclic group having 1 to 60 carbon atoms in addition to a heteroatom as ring-forming atoms. The C₃-C₆₀carbocyclic group and the C₁-C₆₀heterocyclic group may each be a monocyclic group consisting of one ring or a polycyclic group in which two or more rings are condensed. For example, the number of ring-forming atoms in the C₁-C₆₀heterocyclic group may be in a range of 3 to 61.

The term “cyclic group” as used herein may include the C₃-C₆₀carbocyclic group and the C₁-C₆₀heterocyclic group.

The term “π electron-rich C₃-C₆₀cyclic group” as used herein refers to a cyclic group having 3 to 60 carbon atoms and not including *—N═*′ as a ring-forming moiety. The term “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein refers to a heterocyclic group having 1 to 60 carbon atoms and *—N═*′ as a ring-forming moiety.

In some embodiments,

the C₃-C₆₀carbocyclic group may be i) a T1 group or ii) a group in which at least two T1 groups are condensed (for example, the C₃-C₆₀carbocyclic group may be a cyclopentadiene group, an adamantane group, a norbornane group, a benzene group, a pentalene group, a naphthalene group, an azulene group, an indacene group, an acenaphthylene group, a phenalene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a perylene group, a pentaphene group, a heptalene group, a naphthacene group, a picene group, a hexacene group, a pentacene group, a rubicene group, a coronene group, an ovalene group, an indene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, an indenophenanthrene group, and/or an indenoanthracene group),

the C₁-C₆₀heterocyclic group may be i) a T2 group, ii) a group in which at least two T2 groups are condensed, or iii) a group in which at least one T2 group is condensed with at least one T1 group (for example, a pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonapthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like),

the π electron-rich C₃-C₆₀cyclic group may be i) a T1 group, ii) a condensed group in which at least two T1 groups are condensed, iii) a T3 group, iv) a condensed group in which at least two T3 groups are condensed, or v) a condensed group in which at least one T3 group is condensed with at least one T1 group (for example, the π electron-rich C₃-C₆₀cyclic group may be a C₃-C₆₀carbocyclic group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, a thiophene group, a furan group, an indole group, a benzoindole group, a naphthoindole group, an isoindole group, a benzoisoindole group, a naphthoisoindole group, a benzosilole group, a benzothiophene group, a benzofuran group, a carbazole group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an indenocarbazole group, an indolocarbazole group, a benzofurocarbazole group, a benzothienocarbazole group, a benzosilolocarbazole group, a benzoindolocarbazole group, a benzocarbazole group, a benzonaphthofuran group, a benzonapthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, and/or the like), and

the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be i) a T4 group, ii) a group in which at least two T4 groups are condensed, iii) a group in which at least one T4 group is condensed with at least one T1 group, iv) a group in which at least one T4 group is condensed with at least one T3 group, or v) a group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed (for example, the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like),

wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or a bicyclo[2.2.1]heptane) group, a norbornene group, a bicyclo[1.1.1]pentane group, a bicyclo[2.1.1]hexane group, a bicyclo[2.2.2]octane group, or a benzene group,

the T2 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, a borole group, a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a tetrazine group, a pyrrolidine group, an imidazolidine group, a dihydropyrrole group, a piperidine group, a tetrahydropyridine group, a dihydropyridine group, a hexahydropyrimidine group, a tetrahydropyrimidine group, a dihydropyrimidine group, a piperazine group, a tetrahydropyrazine group, a dihydropyrazine group, a tetrahydropyridazine group, or a dihydropyridazine group,

the T3 group may be a furan group, a thiophene group, a 1H-pyrrole group, a silole group, or a borole group, and

the T4 group may be a 2H-pyrrole group, a 3H-pyrrole group, an imidazole group, a pyrazole group, a triazole group, a tetrazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, an azasilole group, an azaborole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, or a tetrazine group.

The term “cyclic group”, “C₃-C₆₀carbocyclic group”, “C₁-C₆₀heterocyclic group”, “π electron-rich C₃-C₆₀cyclic group”, or “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein may each be a group condensed with any suitable cyclic group, a monovalent group, or a polyvalent group (e.g., a divalent group, a trivalent group, a quadvalent group, and/or the like), depending on the structure of the formula to which the term is applied. For example, a “benzene group” may be a benzene ring, a phenyl group, a phenylene group, and/or the like, and this may be understood (e.g., defined) by one of ordinary skill in the art, depending on the structure of the formula including the “benzene group”.

Examples of the monovalent C₃-C₆₀carbocyclic group and the monovalent C₁-C₆₀heterocyclic group may include 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, and a monovalent non-aromatic condensed heteropolycyclic group. Examples of the divalent C₃-C₆₀carbocyclic group and the divalent C₁-C₆₀heterocyclic group may include a C₃-C₁₀cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group.

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof may include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, and a tert-decyl 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 monovalent hydrocarbon group having at least one carbon-carbon double bond in the middle and/or at a terminal end (e.g., the terminus) of the C₂-C₆₀alkyl group. Examples thereof may 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 monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle and/or at a terminal end (e.g., the terminus) of the C₂-C₆₀alkyl group. Examples thereof may 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 a C₁-C₆₀alkyl group). Examples thereof may 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 including 3 to 10 carbon atoms. Examples of the C₃-C₁₀cycloalkyl group may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl (or a bicyclo[2.2.1]heptyl) group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl 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 cyclic group including at least one heteroatom in addition to carbon atoms as a ring-forming atom and having 1 to 10 carbon atoms. Examples thereof may 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 cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and is not aromatic (e.g., has no aromaticity). Examples thereof may 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 cyclic group including at least one heteroatom in addition to carbon atoms as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group may 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-C₁₀heterocycloalkylene 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. The term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl 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 heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, a fluorenyl group, and an ovalenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each independently include two or more rings, the two or more rings may be fused with each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system further including at least one heteroatom in addition to carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system further including at least one heteroatom in addition to carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group may include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, a benzoquinolinyl group, an isoquinolinyl group, a benzoisoquinolinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthrolinyl group, a phthalazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiofuranyl group, and a naphthyridinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each independently include two or more rings, the two or more rings may be fused with each other.

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group having two or more rings condensed with each other and only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group may include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl group, an adamantyl group, and an indenoanthracenyl group. The term “divalent non-aromatic condensed polycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed polycyclic group.

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group having two or more rings condensed to each other and at least one heteroatom in addition to carbon atoms as ring-forming atoms (for example, having 1 to 60 carbon atoms) and, wherein the molecular structure as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a 9,9-dihydroacridinyl group, an azaadamantyl group, and a 9H-xanthenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

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

The term “C₇-C₆₀aryl alkyl group” as used herein refers to a monovalent group represented by -A₁₀₄A₁₀₅(where A₁₀₄may be a C₁-C₅₄alkylene group, and A₁₀₅may be a C₆-C₅₉aryl group), and the term “C₂-C₆₀heteroaryl alkyl group” as used herein refers to a monovalent group represented by -A₁₀₆A₁₀₇(where A₁₀₆may be a C₁-C₅₉alkylene group, and A₁₀₇may be a C₁-C₅₉heteroaryl group).

The term “R_10a” as used herein may be:

deuterium (-D), —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀aryl alkyl group, a C₂-C₆₀heteroaryl alkyl group, —Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), —P(═O)(Q₁₁)(Q₁₂), or any combination thereof;

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀aryl alkyl group, or a C₂-C₆₀heteroaryl alkyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀aryl alkyl group, a C₂-C₆₀heteroaryl alkyl group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof; or

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

Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃and Q₃₁to Q₃₃may each independently be: hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C₁-C₆₀alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof; a C₇-C₆₀aryl alkyl group; or a C₂-C₆₀heteroaryl alkyl group.

The term “heteroatom” as used herein refers to any atom other than a carbon atom. Examples of the heteroatom may include O, S, N, P, Si, B, Ge, Se, or any combination thereof.

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

The term “biphenyl group” as used herein refers to a phenyl group substituted with a phenyl group. The “biphenyl group” belongs to 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 or a phenyl group substituted with two phenyl groups. The “terphenyl group” belongs to a substituted phenyl group having a C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group or a C₆-C₆₀aryl group as a substituent.

The symbols * and *′ as used herein, unless defined otherwise, each refer to a binding site to an adjacent atom in a corresponding formula or moiety.

Hereinafter, compounds and a light-emitting device according to one or more embodiments will be described in more detail with reference to Synthesis Examples and Examples. The expression “B was utilized instead of A” used in describing Synthesis Examples refers to that an amount of B utilized was identical to an amount of A utilized in terms of molar equivalents.

SYNTHESIS EXAMPLES
Synthesis Example 1: Synthesis of Compound BD17

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1) Synthesis of Intermediate [17-A] (9-(4-methoxypyridin-2-yl)-9H-pyrido[2,3-b]indole)

A mixture of 0.5 grams (g) (2.97 millimole (mmol)) of 9H-pyrido[2,3-b]indole, 0.458 mL (4.46 mmol) of 4-methoxy-2-fluoropyridine, and 1.233 g (8.92 mmol) of potassium carbonate in 10 milliliters (mL) of dimethyl sulfoxide (DMSO) was heated at a temperature of 140° C. overnight. The reaction mixture was extracted utilizing ethyl acetate (EA) and water, and an organic layer was extracted therefrom and washed with saline water and concentrated. The obtained solid was subjected to chromatography (EA:n-hexane=1:5) to thereby obtain Intermediate [17-A]. (yield: 68%)

2) Synthesis of Intermediate [17-B]

Intermediate [17-A] was dissolved in a mixed solvent of acetic acid and bromic acid at a ratio of 1:2, and the mixture was heated at a temperature of 120° C. overnight. The mixture solution cooled to room temperature was neutralized by utilizing 2N NaOH aqueous solution, and the resulting solid was filtered. The filtered solid was dried to obtain Intermediate [17-B]. (yield: 80%)

3) Synthesis of Intermediate [17-C]

Intermediate [17-B], 1,3-dibromobenzene (1.0 eq.), copper iodide (0.1 eq.), potassium phosphate (2.0 eq.), and L-proline (0.1 eq.) were suspended in 100 mL of a dimethyl formamide solvent, and the temperature was raised to 120° C., followed by stirring for 12 hours. Once the reaction was complete, the solvent was removed therefrom under reduced pressure, and an organic layer was extracted utilizing methylene chloride and distilled water. The organic layer was washed three times utilizing distilled water, dried utilizing magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate was purified through column chromatography to thereby obtain Intermediate [17-C]. (yield: 79%)

4) Synthesis of Intermediate [17-D]

Intermediate [17-C], N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine, Pd₂(dba)₃, SPhos, and sodium tert-butoxide were added to a reaction vessel, the mixture was suspended in 100 mL of toluene, and the temperature was raised to 120° C., followed by stirring for 4 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom utilizing ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying utilizing sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain Intermediate [17-D]. (yield: 88%)

5) Synthesis of Intermediate [17-E]

Intermediate [17-D], triethyl orthoformate, and 37% aqueous hydrochloric acid solution were added to a reaction vessel, and the temperature was raised to 80° C., followed by stirring for 12 hours. Once the reaction was complete, the temperature was cooled to room temperature, and the resulting solid was filtered and washed utilizing ether. Then, the washed solid was dried to thereby obtain Intermediate [17-E]. (yield: 95%)

6) Synthesis of Intermediate [17-F]

Intermediate [17-E] was dissolved in a mixed solvent of methanol and water at a ratio of 2:1, and NH₄PF₆was added thereto for solidification. The resulting solid was stirred at room temperature for 24 hours, filtered, and washed utilizing ether to thereby obtain Intermediate [17-F]. (yield: 99%)

7) Synthesis of Compound BD17

Intermediate [17-F], dichloro(1,5-cyclooctadiene) platinum, and sodium acetate were suspended in 300 mL of 1,4-dioxane, and the temperature was raised to 110° C., followed by stirring for 72 hours. Once the reaction was complete, the temperature was cooled to room temperature, 250 mL of distilled water was added thereto, and an organic layer was extracted therefrom utilizing ethyl acetate, and the extracted organic layer was washed utilizing saturated aqueous hydrochloric acid solution, and dried utilizing MgSO₄. The resulting product was subjected to column chromatography to thereby obtain Compound BD17. (yield: 28%)

Synthesis Example 2: Synthesis of Compound BD1

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1) Synthesis of Intermediate [1-A] (9-(3-bromophenyl)-9H-pyrido[2,3-b]indole)

A mixture of 9H-pyrido[2,3-b]indole, 1-bromo-3-fluorobenzene, and potassium carbonate in DMSO was heated at a temperature of 140° C. overnight. The reaction mixture was extracted utilizing ethyl acetate (EA) and water, and an organic layer was extracted therefrom and washed with saline solution and concentrated. The obtained solid was subjected to chromatography (EA:n-hexane=1:3) to thereby obtain Intermediate [1-A]. (yield: 66%)

2) Synthesis of Intermediate [1-B]

Intermediate [1-B] was synthesized in substantially the same manner as in Synthesis of Intermediate [17-C] in Synthesis Example 1, except that Intermediate [1-A] was utilized instead of Intermediate [17-B], and 5-(1H-benzo[d]imidazol-1-yl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-ol was utilized instead of 1,3-bromobenzene.

3) Synthesis of Intermediate [1-C]

Intermediate [1-B] was dissolved in a dichloromethane solvent, and methyl iodide was added thereto. The reaction solution was stirred for 12 hours at room temperature. Once the reaction was complete, distilled water was added thereto, followed by drying utilizing magnesium sulfate. The resultant was subjected to column chromatography utilizing a mixed solvent of methanol and dichloromethane at a ratio of 5:95 to thereby obtain Intermediate [1-C]. (yield: 84%)

4) Synthesis of Intermediate [1-D]

Intermediate [1-D] was synthesized in substantially the same manner as in Synthesis of Intermediate [17-F] in Synthesis Example 1, except that Intermediate [1-C]was utilized instead of Intermediate [17-E].

5) Synthesis of Compound BD1

Compound BD1 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that Intermediate [1-D]was utilized instead of Intermediate [17-F].

Synthesis Example 3: Synthesis of Compound BD2

Compound BD2 was synthesized in substantially the same manner as in Synthesis of Compound BD1 in Synthesis Example 2, except that 5-(1H-benzo[d]imidazol-1-yl)-6′-phenyl-[1,1′:2′,1″-terphenyl]-3-ol was utilized instead of 5-(1H-benzo[d]imidazol-1-yl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-ol.

Synthesis Example 4: Synthesis of Compound BD3

Compound BD3 was synthesized in substantially the same manner as in Synthesis of Compound BD1 in Synthesis Example 2, except that 5-(1H-benzo[d]imidazol-1-yl)-2′,6′-di-tert-butyl-[1,1′-biphenyl]-3-ol was utilized instead of 5-(1H-benzo[d]imidazol-1-yl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-ol.

Synthesis Example 5: Synthesis of Compound BD4

Compound BD4 was synthesized in substantially the same manner as in Synthesis of Compound BD1 in Synthesis Example 2, except that 5-(1H-benzo[d]imidazol-1-yl)-[1,1′-biphenyl]-3-ol was utilized instead of 5-(1H-benzo[d]imidazol-1-yl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-ol.

Synthesis Example 6: Synthesis of Compound BD5

Compound BD5 was synthesized in substantially the same manner as in Synthesis of Compound BD1 in Synthesis Example 2, except that 3-(1H-benzo[d]imidazol-1-yl)-5-(triphenylsilyl)phenol was utilized instead of 3-(1H-benzo[d]imidazol-1-yl)-2′,4′,6′-trimethyl-[1,1′-biphenyl]-3-ol.

Synthesis Example 7: Synthesis of Compound BD6

Compound BD6 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that N¹-mesitylbenzene-1,2-diamine was utilized instead of N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine.

Synthesis Example 8: Synthesis of Compound BD7

Compound BD7 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that N¹-(2,6-di-tert-butylphenyl)benzene-1,2-diamine was utilized instead of N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine.

Synthesis Example 9: Synthesis of Compound BD8

Compound BD8 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that N¹-([1,1′:3′,1″-terphenyl]-2′-yl)benzene-1,2-diamine was utilized instead of N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine.

Synthesis Example 10: Synthesis of Compound BD9

Compound BD9 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d10)benzene-1,2-diamine was utilized instead of N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine.

Synthesis Example 11: Synthesis of Compound BD10

Compound BD10 was synthesized in substantially the same manner as in Synthesis of Compound BD17 in Synthesis Example 1, except that N¹-([1,1′:2′,1″:3″,1′″:2′″,1″″-quinquephenyl]-2″-yl)benzene-1,2-diamine was utilized instead of N¹-([1,1′:3′,1″-terphenyl]-2′-yl-2,2″,3,3″,4,4″,5,5″,6,6″-d₁₀)benzene-1,2-diamine.

Compounds synthesized in Synthesis Examples 1 to 11 were identified by ¹H-NMR and matrix-assisted laser desorption/ionization mass spectrometry time-of-flight (MALDI-TOF). The results thereof are shown in Table 2.

Methods of synthesizing compounds other than compounds shown in Table 2 may be easily understood by those skilled in the art by referring to the synthesis pathways and raw materials described above.

TABLE 2

Com-

MALDI-TOF

pound

MS[M⁺]

No.

¹H NMR (CDCl₃, 500 MHz) (ppm)
found
calc.

BD1
δ 8.74 (d, 1H), 8.65 (d, 1H), 8.42 (m, 1H),
777.45
777.79

8.08 (d, 1H), 7.41~7.48 (m, 5H), 7.18

(m, 2H), 7.06 (m, 3H), 6.75 (m, 2H), 6.48

(m, 1H), 5.55 (m, 2H), 3.04 (s, 3H), 2.92

(s, 6H), 2.88 (s, 6H), 2.48 (s, 3H), 2.42

(s, 3H), 1.32 (s, 9H)

BD2
δ 8.73 (d, 1H), 8.37~8.42 (m, 2H), 8.18
886.92
887.22

(d, 1H), 7.44~7.51 (m, 5H), 7.22 (m, 2H),

7.08 (m, 3H), 6.66 (m, 2H), 6.52 (m, 1H),

5.80 (m, 2H), 2.90 (s, 6H), 2.89 (s, 6H),

2.52 (s, 3H), 2.44 (s, 3H), 1.29 (s, 9H)

BD3
δ 8.77 (d, 1H), 8.24 (d, 1H), 8.08 (d, 2H),
847.10
847.28

7.35~7.48 (m, 6H), 7.24 (m, 3H), 7.04

(m, 3H), 6.55 (m, 2H), 6.42 (m, 1H), 5.59

(m, 2H), 3.00 (s, 3H), 2.92 (s, 6H), 2.78

(s, 6H), 2.42 (s, 3H), 2.40 (s, 3H), 1.29

(s, 9H)

BD4
δ 8.74 (d, 1H), 8.65 (d, 1H), 8.42 (m, 1H),
734..99
735.16

8.08 (d, 1H), 7.41~7.48 (m, 5H), 7.18

(m, 2H), 7.06 (m, 3H), 6.75 (m, 2H), 6.48

(m, 1H), 5.55 (m, 2H), 3.04 (s, 3H), 2.92

(s, 6H), 2.88 (m, 3H), 2.48 (s, 3H), 1.32

(s, 9H), 1.21 (s, 18H)

BD5
δ 8.65 (m, 2H), 8.41 (m, 1H), 8.29 (m, 1H),
917.10
917.21

8.04 (d, 1H), 7.41~7.48 (m, 3H), 6.98~7.08

(m, 5H), 6.95 (m, 1H), 6.63~6.69 (m, 4H),

5.55 (m, 1H), 3.00 (s, 3H), 2.92 (s, 6H),

2.88 (m, 3H), 2.46 (s, 3H), 1.35 (s, 9H)

BD6
δ 8.54 (d, 1H), 8.30 (d, 1H), 8.12 (m, 1H),
763.22
763.76

8.01 (d, 1H), 7.41~7.49 (m, 5H), 7.22

(m, 2H), 7.12 (m, 3H), 6.56 (m, 2H), 6.28

(m, 2H), 5.78 (m, 2H), 3.09 (s, 3H), 2.92

(s, 6H), 2.46 (m, 3H), 1.32 (s, 9H), 0.35

(s, 9H)

BD7
δ 8.65 (d, 1H), 8.55 (d, 1H), 8.40 (m, 1H),
833.48
833.91

8.00 (d, 1H), 7.41~7.45 (m, 5H), 7.28

(m, 2H), 7.01 (m, 2H), 6.75 (m, 2H), 6.48

(m, 1H), 5.53 (m, 2H), 3.05 (s, 3H), 2.90

(s, 6H), 2.85 (m, 3H), 2.42 (s, 3H), 1.28

(s, 9H), 1.20 (s, 18H)

BD8
δ 8.98 (s, 1H), 8.55 (d, 1H), 8.10~8.13
873.05
873.21

(d, 1H), 7.82 (2H), 7.57 (d, 2H), 7.28~7.33

(m, 2H), 7.12~7.18 (m, 1H), 6.98~7.00

(m, 2H), 6.72 (m, 2H), 3.64 (s, 3H)

BD9
δ 8.45 (m, 1H), 8.09~8.13 (m, 2H), 7.84
870.10
870.20

(s, 1H), 7.54~7.57 (m, 1H), 7.40~7.44

(m, 1H), 7.25~7.30 (m, 2H), 6.98~7.02

(m, 2H), 6.68~6.72 (m, 2H) 3.68 (s, 3H),

1.34 (s, 9H)

BD10
δ 8.54~8.57 (m, 2H), 7.55~7.64 (m, 4H),
1025.11
1025.27

7.25~7.34 (m, 3H), 6.85 (d, 2H), 6.70~6.73

(m, 4H), 3.47 (s, 6H)

BD17
δ 7.55~7.58 (m, 2H), 7.30 (t, 1H), 6.89~6.92
884.12
884.25

(d, 2H), 6.80~6.84 (m, 2H), 6.38~6.41

(s, 2H), 2.86 (s, 6H), 2.73 (s, 6H)

EXAMPLE
Example 1

A Corning 15 Ohms per square centimeter (Ω/cm₂) (1,200 Å) ITO glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes each, and cleaned by exposure to ultraviolet rays with ozone to utilize the glass substrate as an anode. Then, the glass substrate was mounted to a vacuum-deposition apparatus.

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

3,3-di(9H-carbazol-9-yl)biphenyl (mCBP) as a host and Compound BD1 as a dopant were co-deposited on the hole transport layer (at a weight ratio of 90:10) to form an emission layer having a thickness of 300 Å.

Diphenyl(4-(triphenylsilyl)phenyl)-phosphine oxide (TSPO1) was vacuum-deposited on the emission layer to a thickness of 50 Å to form a hole blocking layer. Alq₃was deposited on the hole blocking layer as an electron transport layer to a thickness of 300 Å. LiF, which is a halogenated alkali metal, was deposited on the electron transport layer to a thickness of 10 Å as an electron injection layer, and Al was vacuum-deposited to a thickness of 3,000 Å to form a LiF/Al cathode, thereby completing the manufacture of a light-emitting device.

Examples 2 to 5

Light-emitting devices were manufactured in substantially the same manner as in Example 1, except that the compounds shown in Table 3 were utilized instead of Compound BD1 as a dopant in the formation of a respective emission layer.

Comparative Examples 1 to 4

Light-emitting devices were manufactured in substantially the same manner as in Example 1, except that Compounds C1 to C3 and L-21 were utilized instead of Compound BD1 as a dopant in the formation of a respective emission layer.

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The driving voltage, current density, luminance, luminescence efficiency, and maximum emission wavelength of the light-emitting devices manufactured according to each of Examples 1 to 5 and Comparative Examples 1 to 4 were measured by utilizing Kethley SMU 236 and a luminance meter PR650. The lifespan (T₉₀) was measured by measuring a time (hour) for the luminance of each light-emitting device to decline to 90% of its initial luminance. The results thereof are shown in Table 3.

TABLE 3

Maximum

Driving
Current

Emission
emission
T₉₀

Emission
voltage
density
Luminance
efficiency
wavelength
lifespan

layer
(V)
(mA/cm²)
(Cd/m²)
(cd/A)
(nm)
(hours)

Example 1
BD1
5.1
5.3
1,000
19.8
456
35

Example 2
BD4
4.1
5.5
1,000
20.5
461
88

Example 3
BD8
4.2
5.4
1,000
18.9
459
108

Example 4
BD10
4.2
4.9
1,000
20.8
462
95

Example 5
BD17
4.3
4.8
1,000
24.9
455
125

Comparative
Compound
4.6
4.4
1,000
22.5
454
15

Example 1
C1

Comparative
Compound
5.2
5.0
1,000
20.5
470
6.5

Example 2
C2

Comparative
Compound
4.7
5.3
1,000
10.5
489
0.2

Example 3
C3

Comparative
Compound
4.8
4.9
1,000
19.9
465
5.0

Example 4
L-21

Referring to the results of Table 3, the light-emitting devices of Examples 1 to 5, including the compounds according to one or more embodiments as emission layer dopants, were each found to have equal to or improved driving voltage and luminescence efficiency, and significantly improved lifespan, as compared with the light-emitting devices of Comparative Examples 1 to 4.

In other words, when the compounds according to one or more embodiments are utilized in a light-emitting device, the device may have suitable (e.g., excellent) driving voltage, luminescence efficiency, and/or lifespan.

The light-emitting device including the organometallic compound may have a low driving voltage, high efficiency, and long lifespan. In addition, emission wavelength may be easily controlled to thereby realize high colorimetric purity.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Further, the use of “may” when describing embodiments of the inventive concept refers to “one or more embodiments of the inventive concept.”

As used herein, the term “substantially,” “about,” and similar terms are used as terms of approximation and not as terms of degree, and are intended to account for the inherent deviations in measured or calculated values that would be recognized by those of ordinary skill in the art. “About” or “approximately,” as used herein, is inclusive of the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art, considering the measurement in question and the error associated with measurement of the particular quantity (i.e., the limitations of the measurement system). For example, “about” may mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

Also, any numerical range recited herein is intended to include all subranges of the same numerical precision subsumed within the recited range. For example, a range of “1.0 to 10.0” is intended to include all subranges between (and including) the recited minimum value of 1.0 and the recited maximum value of 10.0, that is, having a minimum value equal to or greater than 1.0 and a maximum value equal to or less than 10.0, such as, for example, 2.4 to 7.6. Any maximum numerical limitation recited herein is intended to include all lower numerical limitations subsumed therein and any minimum numerical limitation recited in this specification is intended to include all higher numerical limitations subsumed therein. Accordingly, Applicant reserves the right to amend this specification, including the claims, to expressly recite any sub-range subsumed within the ranges expressly recited herein.

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, and equivalents thereof.

ORGANOMETALLIC COMPOUND, LIGHT-EMITTING DEVICE INCLUDING ORGANOMETALLIC COMPOUND, AND ELECTRONIC APPARATUS INCLUDING LIGHT-EMITTING DEVICE

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