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

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2022-0005328, filed on Jan. 13, 2022, 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 a light-emitting device including an organometallic compound, an electronic apparatus including the light-emitting device, and the organometallic compound.

2. Description of the Related Art

From among light-emitting devices, self-emissive devices have relatively wide viewing angles, high contrast ratios, short response times, and/or excellent or suitable characteristics in terms of luminance, 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 move toward the emission layer through the hole transport region, and electrons provided from the second electrode move toward the emission layer through the electron transport region. Carriers, such as the holes and electrons, recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state, thereby generating light.

SUMMARY

Aspects according to one or more embodiments of the present disclosure are directed toward a light-emitting device including a novel organometallic compound, an electronic apparatus including the light-emitting device, and the novel 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, a light-emitting device includes

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 an organometallic compound represented by Formula 1.

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In Formula 1,

M may be platinum (Pt) or palladium (Pd),

Y₁to Y₄may each independently be a chemical bond, O, S, or Se, wherein the chemical bond may be a covalent bond or a coordinate bond,

X₁to X₄may each independently be C or N,

ring CY₁to ring CY₄may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group,

at least one of (e.g., at least one selected from the group consisting of) ring CY₁to ring CY₄may include a 5-membered ring,

L₁to L₃may each independently be a single bond, *—C(R_1a)(R_1b)—*′, *—C(R_1a)═*′, *═C(R_1a)—*′, *—C(R_1a)═C(R_1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R_1a)—*′, *—N(R_1a)—*′, *—O—*′, *—P(R_1a)—*′, *—Si(R_1a)(R_1b)—*′, *—P(═O)(R_1a)—*′, *—S(═O)—*′, *—S(═O)₂—*¹, *—Ge(R_1a)(R_1b)—*′, *—Se—*′, a C₃-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a, or any combination thereof, wherein * and *′ each indicate a binding site to a neighboring atom,

n1 to n3 may each independently be an integer from 1 to 10,

R₁to R₄, R_1a, and R_1bmay 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 C₁-C₆₀alkylthio 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, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

a1 to a4 may each independently be an integer from 0 to 10,

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),

Q₁to Q_3,Q₁₁to Q_13,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, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; 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-C₆₀arylalkyl group; or a C₂-C₆₀heteroarylalkyl group, and

the organometallic compound represented by Formula 1 may satisfy at least one of <Condition 1-1>to <Condition 1-5>

<Condition 1-1>

at least one selected from the group consisting of Y₁and Y₄is not a chemical bond, and L₂is not a single bond,

<Condition 1-2>

Y₂is not a chemical bond, and L₁is not a single bond,

<Condition 1-3>

Y₂is not a chemical bond, and L₂is not a single bond,

<Condition 1-4>

Y₃is not a chemical bond, and L₂is not a single bond, and

<Condition 1-5>

Y₃is not a chemical bond, and L₃is not a single bond.

According to one or more embodiments, an electronic apparatus includes the light-emitting device.

According to one or more embodiments, provided is the 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, and duplicative descriptions thereof may not be provided. 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 drawings, 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”, “at least one selected from a, b, and c”, “at least one selected from the group consisting of a, b, and c”, etc., indicates only a, only b, only c, both (e.g., simultaneously) a and b, both (e.g., simultaneously) a and c, both (e.g., simultaneously) b and c, all of a, b, and c, or variations thereof.

A light-emitting device according to an embodiment of the present disclosure may include: a first electrode; a second electrode facing the first electrode; an interlayer located between the first electrode and the second electrode and including an emission layer; and an organometallic compound represented by Formula 1:

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wherein, in Formula 1, M may be platinum (Pt) or palladium (Pd).

Y₁to Y₄in Formula 1 may each independently be a chemical bond, O, S, or Se, wherein the chemical bond may be a covalent bond or a coordinate bond.

In an embodiment, i) Y₁may be O, S, or Se, and Y₂to Y₄may each be a chemical bond, ii) Y₂may be O, S, or Se, and Y₁, Y₃, and Y₄may each be a chemical bond, iii) Y₃may be O, S, or Se, and Y₁, Y₂, and Y₄may each be a chemical bond, or iv) Y₄may be O, S, or Se, and Y₁to Y₃may each be a chemical bond.

X₁to X₄in Formula 1 may each independently be C or N.

In an embodiment, i) when Y₁is O, S, or Se, X₁may be C, ii) when Y₂is O, S, or Se, X₂may be C, iii) when Y₃is O, S, or Se, X₃may be C, and iv) when Y₄is O, S, or Se, X₄may be C.

Ring CY₁to ring CY₄in Formula 1 may each independently be a C₅-C₃₀carbocyclic group or a C₁-C₃₀heterocyclic group.

In an embodiment, at least one of ring CY₁to ring CY₄may include a 5-membered ring.

In an embodiment, when at least one of (e.g., at least one selected from the group consisting of) ring CY₁to ring CY₄includes a 5-membered ring, at least one of the 5-membered rings may be bonded to M in Formula 1 via one of Y₁to Y₄.

For example, when ring CY₁includes a 5-membered ring, the 5-membered ring may be bonded to M in Formula 1 via Y₁, and the 5-membered ring may be bonded to ring CY2 via L₁. For example, when ring CY2 includes a 5-membered ring, the 5-membered ring may be bonded to M in Formula 1 via Y₂, the 5-membered ring may be bonded to ring CY₁via L₁, and the 5-membered ring may be bonded to ring CY₃via L₂. For example, when ring CY₃includes a 5-membered ring, the 5-membered ring may be bonded to M in Formula 1 via Y₃, the 5-membered ring may be bonded to ring CY2 via L₂, and the 5-membered ring may be bonded to ring CY₄via L₃. For example, when ring CY₄includes a 5-membered ring, the 5-membered ring may be bonded to M in Formula 1 via Y₄, and the 5-membered ring may be bonded to ring CY₃via L₃.

In an embodiment, when at least one of ring CY₁to ring CY₄includes a 5-membered ring, the 5-membered ring may include at least one nitrogen. For example, the 5-membered ring may include one nitrogen, and may optionally further include nitrogen (e.g., a second nitrogen), oxygen (O), and/or sulfur (S).

In an embodiment, at least two of ring CY₁to ring CY₄may each independently be a C₁-C₃₀heterocyclic group.

In an embodiment, two of ring CY₁to ring CY₄may each independently be a C₅-C₃₀carbocyclic group, and the remaining two of ring CY₁to ring CY₄may each independently be a C₁-C₃₀heterocyclic group. In this regard, at least one of the C₁-C₃₀heterocyclic groups may be a 5-membered ring.

For example, ring CY₁to ring CY₄may 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 thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an azabenzogermole group, an azabenzothiophene group, an azabenzoselenophene group, an azabenzofuran group, an azacarbazole group, an azadibenzoborole group, an azadibenzophosphole group, an azafluorene group, an azadibenzosilole group, an azadibenzogermole group, an azadibenzothiophene group, an azadibenzoselenophene group, an azadibenzofuran group, an azadibenzothiophene 5-oxide group, an aza-9H-fluorene-9-one group, an azadibenzothiophene 5,5-dioxide 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 triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole 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, ring CY₁to ring CY₄may each independently be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluorene-9-one group, a dibenzothiophene 5,5-dioxide 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 triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, or a benzothiadiazole group.

In an embodiment, moieties represented by

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in Formula 1 may each independently be one of the groups represented by Formulae CY(1)-1 to CY(1)-18:

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wherein, in Formulae CY(1)-1 to CY(1)-18,

X₁₁may be C or N,

Z₁may be O, S, or Se,

Z₂may be O, S, Se, N(R_11a), C(R_11a)(R_11b), or Si(R_11a)(R_11b),

R₁₁, R₁₂, R_11a, and R_11bmay 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 C₁-C₆₀alkylthio 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, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

b11 may be an integer from 0 to 4,

b12 may be an integer from 0 to 6,

b13 may be an integer from 0 to 2,

b14 may be an integer from 0 to 3,

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

R_10aand Q₁to Q₃are respectively the same as described herein.

In an embodiment, R₁₁, R₁₂, R_11a, and R_11bmay each independently be hydrogen, deuterium, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heteroaryl group unsubstituted or substituted with at least one R_10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R_10a, or a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R_10a. R_10ais the same as described herein.

In an embodiment, R₁₁, R₁₂, R_11a, and R_11bmay 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, or a C₁-C₂₀alkylthio group;

a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, or a C₁-C₂₀alkylthio group, each substituted with deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, or an azadibenzosilolyl 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 C₁-C₂₀alkoxy group, a C₁-C₂₀alkylthio group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a C₁-C₁₀alkylphenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzoimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzoisothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azafluorenyl group, an azadibenzosilolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —B(Q₃₁)(Q₃₂), —P(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

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

Q₁to Q₃and Q₃₁to Q₃₃may each independently be: —CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, or —CD₂CDH_2;or

an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group, each unsubstituted or substituted with at least one of deuterium, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, or a triazinyl group.

In an embodiment, moieties represented by

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in Formula 1 may each independently be one of the groups represented by Formulae CY(2)-1 to CY(2)-18:

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wherein, in Formulae CY(2)-1 to CY(2)-18,

X₁₂may be C or N,

Z₃may be O, S, or Se,

Z₄may be O, S, Se, N(R_21a), C(R_21a)(R_21b), or Si(R_21a)(R_21b),

R₂₁, R₂₂, R_21a, and R_21bmay 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 C₁-C₆₀alkylthio 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, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

b21 may be an integer from 0 to 3,

b22 may be an integer from 0 to 5,

b23 may be 0 or 1,

b24 may be an integer from 0 to 4,

b25 may be an integer from 0 to 2,

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

R_10aand Q₁to Q₃are respectively the same as described herein.

In an embodiment, R₂₁, R₂₂, R_21a, and R_21bmay each independently be hydrogen, deuterium, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heteroaryl group unsubstituted or substituted with at least one R_10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R_10a, or a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R_10a. R_10ais the same as described herein.

In an embodiment, R₂₁, R₂₂, R_21a, and R_21beach 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, or a C₁-C₂₀alkylthio group;

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

L₁to L₃in Formula 1 may each independently be a single bond, *—C(R_1a)(R_1b)—*′, *—C(R_1a)═*′, *′C(R_1a)—*′, *—C(R_1a)═C(R_1b)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R_1a)—*′, *—N(R_1a)—*′, *—O—*′, *—P(R_1a)—*′, *—Si(R_1a)(R_1b)—*′, *—P(═O)(R_1a)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—Ge(R_1a)(R_1b)—*′, *—Se—*′, a C₃-C₃₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₃₀heterocyclic group unsubstituted or substituted with at least one R_10a, or any combination thereof (e.g., the any combination being selected from L₁, L₂, and L₃, each of L₁, L₂, and L₃independently being one of the above disclosed single bond or groups). * and *′ each indicate a binding site to a neighboring atom. R_1aand R_1bare respectively the same as respectively described herein.

In an embodiment, L₁to L₃may each independently be a single bond, *—C(R_1a)(R_1b)—*′, *—C(R_1a)═*′, *′C(R_1a)—*′, *—C(R_1a)═C(R_1b)—*′, *—C≡C—*′, *—Se—*′, a C₁-C₃₀arylene group unsubstituted or substituted with at least one R_10a, or any combination thereof.

For example, L₁to L₃may each independently be a single bond, *—C(R_1a)(R_1b)—*′, *—C(R_1a)═*′, *′C(R_1a)—*′, *—C(R_1a)═C(R_1b)—*′, *—C≡C—*′, *—Se—*′, a phenylene group, a naphthylene group, a phenanthrenylene group, an anthracenylene group, a pyrenylene group, a chrysenylene group, or any combination thereof.

n1 to n4 in Formula 1 may each independently be an integer from 1 to 10.

In an embodiment, *-(L₁)_n1-*′, *-(L₂)_n2-*′, and *-(L₃)_n3—*′ in Formula 1 may each independently be a single bond, at least one of the groups represented by Formulae L-1 to L-32, or any combination thereof:

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* and *′ in the groups represented by Formulae L-1 to L-32 each indicate a binding site to a neighboring atom.

R₁to R₄, R_1a, and R_1bin Formula 1 may 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 C₁-C₆₀alkylthio 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, —C(Q₁)(Q₂)(Q₃), —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂). R_10aand Q₁to Q₃are respectively the same as described herein.

In an embodiment, R₁to R₄, R_1a, and R_1bmay 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, or a C₁-C₂₀alkylthio group;

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

In an embodiment, R₁to R₄may each independently be hydrogen, deuterium, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heteroaryl group unsubstituted or substituted with at least one R_10a, a monovalent non-aromatic condensed polycyclic group unsubstituted or substituted with at least one R_10a, or a monovalent non-aromatic condensed heteropolycyclic group unsubstituted or substituted with at least one R_10a. R_10ais the same as described herein.

In an embodiment, R₁to R₄may each independently be: hydrogen or deuterium;

a C₁-C₁₀alkyl group unsubstituted or substituted with deuterium, a phenyl group, or any combination thereof; or

a phenyl group or a naphthyl group, each unsubstituted or substituted with deuterium, a C₁-C₁₀alkyl group, a phenyl group, or any combination thereof.

a1 to a4 in Formula 1 may each independently be an integer from 0 to 10.

The organometallic compound represented by Formula 1 may satisfy at least one of <Condition 1-1>to <Condition 1-5>:

<Condition 1-1>

at least one of Y₁or Y₄is not a chemical bond, and L₂is not a single bond;

<Condition 1-2>

Y₂is not a chemical bond, and L₁is not a single bond;

<Condition 1-3>

Y₂is not a chemical bond, and L₂is not a single bond;

<Condition 1-4>

Y₃is not a chemical bond, and L₂is not a single bond; and

<Condition 1-5>

Y₃is not a chemical bond, and L₃is not a single bond.

In an embodiment, the organometallic compound may satisfy one of <Condition 1-1>to <Condition 1-5>.

In one or more embodiments, the organometallic compound represented by Formula 1 may satisfy one of <Condition 1-6>and <Condition 1-7>:

<Condition 1-6>

Y₂is not a chemical bond, and L₃is not a single bond; and

<Condition 1-7>

Y₃is not a chemical bond, and L₁is not a single bond.

In an embodiment, the organometallic compound may have a triplet metal-to-ligand charge transfer (³MLCT) value of 20% or more, 21% or more, 22% or more, or 23% or more.

In an embodiment, the organometallic compound may be one of Compounds D1 to D67:

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The organometallic compound represented by Formula 1 has a structure in which M, which is a metal, is bonded to at least one of ring CY₁to ring CY₄via a linker that is not a chemical bond (for example, oxygen, etc.), and at least one of L₁to L₃, which are linkers between ring CY₁to ring CY₄, is not a single bond. That is, M is bonded to at least one of ring CY₁to ring CY₄via a linker that is O, S, or Se (i.e., not a chemical bond) and at least one of L₁to L₃is not a single bond.

Because of such a structure, a planar structure may be easily formed in the organometallic compound, and as a result, a structure in a ground state may be stabilized, thereby obtaining a high ³MLCT value. Accordingly, the usage of the organometallic compound may improve efficiency characteristics of a light-emitting device, and may realize (e.g., provide) an electronic device (for example, an organic light-emitting device) having high efficiency characteristics.

The highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the bandgap, the Ti energy level, the maximum emission wavelength (λmax), and the ³MLCT of some compounds of the organometallic compound represented by Formula 1 and comparative compounds are evaluated utilizing the density functional theory (DFT) method of the Gaussian program (structurally optimized at the level of B3LYP, 6-31G(d,p)), and results thereof are shown in Table 1. In Table 1, Ti is a value obtained by calculating the energy when molecules of a compound are excited from a ground state to a triplet (T₁) state.

TABLE 1

Com-
HOMO
LUMO
Bandgap
T₁
λ max

pound
(eV)
(eV)
(eV)
(eV)
(nm)

³MLCT

Example 1
D1
−4.64
−2.03
2.61
2.37
522
65

Example 2
D2
−4.69
−1.98
2.71
2.31
537
56

Example 3
D3
−4.65
−2.03
2.61
2.36
526
55

Example 4
D4
−4.62
−2.05
2.58
2.34
531
55

Example 5
D5
−4.74
−2.06
2.68
2.35
528
53

Example 6
D6
−4.70
−2.05
2.66
2.31
537
48

Example 7
D7
−4.67
−2.05
2.63
2.36
525
47

Example 8
D8
−4.61
−2.04
2.57
2.34
530
47

Example 9
D9
−4.65
−1.69
2.96
2.37
523
46

Example 10
D10
−4.74
−2.01
2.72
2.38
520
42

Example 11
D11
−4.70
−2.09
2.61
2.35
527
41

Example 12
D12
−4.68
−2.08
2.60
2.36
525
41

Example 13
D13
−4.65
−2.05
2.61
2.36
526
40

Example 14
D14
−4.71
−2.00
2.71
2.38
521
39

Example 15
D15
−4.75
−2.03
2.72
2.39
519
37

Example 16
D16
−4.66
−1.98
2.68
2.38
522
35

Example 17
D17
−5.22
−2.22
3.00
2.06
602
33

Example 18
D18
−4.62
−1.28
3.33
2.47
503
31

Example 19
D19
−4.73
−2.11
2.62
2.02
615
30

Example 20
D20
−4.81
−1.44
3.36
2.46
504
30

Example 21
D21
−4.84
−2.09
2.75
2.05
605
29

Example 22
D22
−5.06
−1.78
3.27
2.23
557
29

Example 24
D24
−4.88
−1.14
3.74
2.60
477
29

Example 25
D25
−4.91
−1.15
3.76
2.62
473
29

Example 26
D26
−5.04
−1.98
3.06
2.26
550
27

Example 27
D27
−4.84
−2.15
2.69
1.93
641
27

Example 28
D28
−4.92
−2.10
2.82
2.00
621
27

Example 29
D29
−4.82
−1.10
3.72
2.62
474
27

Example 30
D30
−4.97
−1.97
3.01
1.81
685
26

Example 31
D31
−5.02
−1.79
3.23
2.39
519
26

Example 32
D32
−4.77
−2.11
2.67
2.38
520
26

Example 33
D33
−4.99
−1.86
3.13
2.22
558
26

Example 34
D34
−5.05
−1.45
3.60
2.53
491
26

Example 35
D35
−4.68
−1.44
3.23
2.54
489
25

Example 36
D36
−4.86
−1.30
3.56
2.61
474
25

Example 37
D37
−4.90
−1.04
3.85
2.57
482
25

Example 38
D38
−5.01
−2.01
3.01
1.81
684
25

Example 39
D39
−4.89
−1.97
2.92
2.39
519
25

Example 40
D40
−4.84
−1.54
3.31
2.48
500
25

Example 41
D41
−5.05
−1.22
3.84
2.53
491
25

Example 42
D42
−4.78
−1.42
3.36
2.47
502
25

Example 43
D43
−4.69
−1.06
3.63
2.54
487
25

Example 44
D44
−5.12
−2.00
3.12
1.81
684
24

Example 45
D45
−5.04
−1.92
3.13
2.27
547
24

Example 46
D46
−4.87
−1.01
3.86
2.69
461
24

Example 47
D47
−4.92
−1.54
3.39
2.46
504
24

Example 48
D48
−5.10
−2.25
2.85
2.06
602
23

Example 49
D49
−5.28
−2.08
3.20
1.94
639
23

Example 50
D50
−4.87
−1.85
3.01
2.42
512
23

Example 51
D51
−5.12
−1.94
3.18
2.27
547
23

Example 52
D52
−4.67
−2.05
2.63
2.38
522
66

Example 53
D53
−4.64
−2.03
2.62
2.37
522
65

Example 54
D54
−4.68
−2.08
2.60
2.37
523
63

Example 55
D55
−4.64
−2.03
2.61
2.32
534
55

Example 56
D56
−4.65
−2.04
2.61
2.35
527
55

Example 57
D57
−4.66
−2.03
2.64
2.29
541
52

Example 58
D58
−4.68
−2.04
2.64
2.37
524
46

Example 59
D59
−4.68
−2.04
2.63
2.37
524
45

Example 60
D60
−4.80
−2.06
2.74
2.40
517
45

Example 61
D61
−4.64
−2.03
2.61
2.36
526
43

Example 62
D62
−4.71
−2.00
2.71
2.38
521
40

Example 63
D63
−4.74
−2.09
2.65
2.37
522
33

Example 64
D64
−4.66
−1.97
2.69
2.37
522
33

Example 65
D65
−4.71
−2.01
2.70
2.38
521
32

Example 66
D66
−4.74
−2.09
2.65
2.38
522
26

Comparative
R2
−5.01
−1.88
3.13
2.32
525
5.84

Example 2

Comparative
R3
−4.87
−1.76
3.11
2.40
497
1.06

Example 3

Comparative
R4
−4.86
−2.29
2.57
1.87
662
9.23

Example 4

Comparative
R5
−5.62
−2.09
3.53
2.68
463
10.37

Example 5

Comparative
R6
−4.78
−1.71
3.07
2.12
585
6.4

Example 6

Comparative
R7
−4.80
−1.73
3.07
2.12
585
6.3

Example 7

Comparative
R8
−4.78
−1.78
3.00
2.05
605
5.3

Example 8

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From Table 1, it is confirmed that the compounds represented by Formula 1 according to the present disclosure show higher ³MLCT value and have excellent or suitable characteristics as a luminescent material.

Methods of synthesizing the organometallic compound represented by Formula 1 may be easily understood to those of ordinary skill in the art by referring to Synthesis Examples and/or Examples described herein.

In an embodiment,

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 located between the first electrode and the emission layer and an electron transport region located 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 hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

In one or more embodiments, the interlayer of the light-emitting device may include the organometallic compound represented by Formula 1.

In one or more embodiments, the emission layer of the light-emitting device may include the organometallic compound represented by Formula 1.

In one or more embodiments, the emission layer may be to emit red light, green light, or blue light.

In one or more embodiments, the emission layer of the light-emitting device may include a dopant and a host, and the organometallic compound represented by Formula 1 may be included in the dopant. For example, the organometallic compound may act (e.g., serve) as a dopant. For example, the emission layer may be to emit red light, green light, or blue light.

In one or more embodiments, the electron transport region of the light-emitting device may include a hole blocking layer, and the hole blocking layer may include a phosphine oxide-containing compound, a silicon-containing compound, or any combination thereof. For example, the hole blocking layer may be in direct contact with the emission layer.

In one or more embodiments, the light-emitting device may further include at least one of a first capping layer located outside the first electrode or a second capping layer located outside the second electrode, and the organometallic compound represented by Formula 1 may be included in at least one of the first capping layer or the second capping layer. The first capping layer and/or the second capping layer are respectively the same those as described herein.

In an embodiment, 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 “(interlayer and/or capping layer) includes an organometallic compound” as used herein may be understood as “(interlayer and/or capping layer) may include one kind of organometallic compound represented by Formula 1 or two different kinds of organometallic compounds, each represented by Formula 1.”

For example, the interlayer and/or the capping layer may include only Compound 1 as the organometallic compound. In this regard, a Compound 1 may be present in the emission layer of the light-emitting device. In one or more embodiments, the interlayer may include, as the organometallic compound, Compound 1 and Compound 2. In this regard, Compound 1 and Compound 2 may be present in substantially the same layer (for example, both (e.g., simultaneously) Compound 1 and Compound 2 may be present in the emission layer), or may be present in different layers (for example, Compound 1 may be present in the emission layer, and Compound 2 may be present in the electron transport region).

The term “interlayer” as used herein refers to a single layer and/or all of a plurality of layers located between the first electrode and the second electrode of the light-emitting device.

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 includes 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 will be described with reference to FIG. 1.

First electrode 110

In FIG. 1, a substrate may be additionally disposed under the first electrode 110 and/or on the second electrode 150. As the substrate, a glass substrate or a plastic substrate may be utilized. In one or more embodiments, the substrate may be a flexible substrate, and may include plastics with excellent or suitable heat resistance and durability, such as polyimide, polyethylene terephthalate (PET), polycarbonate, polyethylene naphthalate, polyarylate (PAR), polyetherimide, or any combination thereof.

The first electrode 110 may be formed by, for example, depositing or sputtering a material for forming the first electrode 110 on the substrate. When the first electrode 110 is an anode, the material for forming the first electrode 110 may be a high work function material that facilitates injection of holes.

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

The first electrode 110 may have a single-layered structure consisting of a single layer or a multi-layered structure including a plurality of layers. For example, the first electrode 110 may have a three-layered structure of ITO/Ag/ITO.

Interlayer 130

The interlayer 130 is disposed on the first electrode 110. The interlayer 130 includes an emission layer.

The interlayer 130 may further include a hole transport region located between the first electrode 110 and the emission layer and an electron transport region located between the emission layer and the second electrode 150.

The interlayer 130 may further include, in addition to one or more suitable organic materials, a metal-containing compound, such as an organometallic compound, an inorganic material, such as a quantum dot, and/or the like.

In one or more embodiments, 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 or more emitting units. When the interlayer 130 includes the two or more emitting units and the charge generation layer as described above, 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 (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including 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 any combination thereof.

For example, the hole transport region may have a multi-layered structure including 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, with the constituting layers of each structure being stacked sequentially from the first electrode 110 in the respective stated order.

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

embedded image

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—*′, *—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 linked to each other via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R₁₀a, or a C₂-C₅alkenylene group unsubstituted or substituted with at least one R_10ato form a C₈-C₆₀polycyclic group (for example, a carbazole group, etc.) unsubstituted or substituted with at least one R_10a(for example, see Compound HT16, etc.),

R₂₀₃and R₂₀₄may optionally be linked to each other via a single bond, a C₁-C₅alkylene group unsubstituted or substituted with at least one R₁₀a, 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 one or more embodiments, each of Formulae 201 and 202 may 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_10care each the same as described in connection with R_10a, ring CY201 to ring CY204 may 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_10aas described herein.

In an embodiment, ring CY201 to ring CY204 in Formulae CY201 to CY217 may each independently be a benzene group, a naphthalene group, a phenanthrene group, or an anthracene group.

In one or more embodiments, each of Formulae 201 and 202 may 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 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 (e.g., may exclude) any of the groups represented by Formulae CY201 to CY203.

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

In an embodiment, the hole transport region may include at least 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/camphor sulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate) (PANI/PSS), or any combination thereof:

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

The emission auxiliary layer may increase light-emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by the emission layer, and the electron blocking layer may block or reduce the leakage of electrons from the emission layer to the hole transport region. Materials that may be included in the hole transport region may be included in the emission auxiliary layer and the electron blocking layer.

p-dopant

The hole transport region may further include, in addition to these materials, a charge-generation material for the improvement of conductive properties. The charge-generation material may be uniformly or non-uniformly dispersed in the hole transport region (for example, in the form of a single layer consisting of a charge-generation material).

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

In one or more embodiments, the LUMO energy level of the p-dopant may be −3.5 eV or less.

In an embodiment, the p-dopant may include a quinone derivative, a cyano group-containing compound, 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 cyano group-containing compound may include HAT-CN and a compound represented by Formula 221:

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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 any combination thereof, and element EL₂may be a non-metal, a metalloid, or any combination thereof.

Examples of the metal may include: an alkali metal (for example, lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), etc.); an alkaline earth metal (for example, beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), etc.); a transition metal (for example, titanium (T₁), 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), etc.); a post-transition metal (for example, zinc (Zn), indium (In), tin (Sn), etc.); and a lanthanide metal (for example, 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), etc.).

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

Examples of the non-metal may include oxygen (O) and halogen (for example, F, Cl, Br, I, etc.).

For example, the compound containing element EL1 and element EL₂may include a metal oxide, a metal halide (for example, a metal fluoride, a metal chloride, a metal bromide, a metal iodide, etc.), a metalloid halide (for example, a metalloid fluoride, a metalloid chloride, a metalloid bromide, a metalloid iodide, etc.), a metal telluride, or any combination thereof.

Examples of the metal oxide may include tungsten oxide (for example, WO, W₂O₃, WO₂, WO₃, W₂O₅, etc.), vanadium oxide (for example, VO, V₂O₃, V)₂, V₂O₅, etc.), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, etc.), and rhenium oxide (for example, ReO₃, etc.).

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, and a lanthanide metal halide.

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

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, and BaI₂.

Examples of the transition metal halide may include titanium halide (for example, TiF₄, TiCl₄, TiBr₄, TiI₄, etc.), zirconium halide (for example, ZrF₄, ZrCl₄, ZrBr₄, ZrI₄, etc.), hafnium halide (for example, HfF₄, HfC₁₄, HfBr₄, HfI₄, etc.), vanadium halide (for example, VF₃, VCl₃, VBr₃, VI₃, etc.), niobium halide (for example, NbF₃, NbC₁₃, NbBr₃, NbI₃, etc.), tantalum halide (for example, TaF₃, TaCl₃, TaBr₃, Tal₃, etc.), chromium halide (for example, CrF₃, CrCl₃, CrBr₃, CrI₃, etc.), molybdenum halide (for example, MoF₃, MoCl₃, MoBr₃, Mol₃, etc.), tungsten halide (for example, WF₃, WCl₃, WBr₃, WI₃, etc.), manganese halide (for example, MnF₂, Mncl₂, MnBr₂, MnI₂, etc.), technetium halide (for example, TcF₂, Tccl₂, TcBr₂, TcI₂, etc.), rhenium halide (for example, ReF₂, Recl₂, ReBr₂, ReI₂, etc.), iron halide (for example, FeF₂, Fecl₂, FeBr₂, FeI₂, etc.), ruthenium halide (for example, RuF₂, Rucl₂, RuBr₂, RuI₂, etc.), osmium halide (for example, OsF₂, Oscl₂, OsBr2, 0s12, etc.), cobalt halide (for example, CoF₂, CoCl₂, CoBr₂, CoI₂, etc.), rhodium halide (for example, RhF₂, RhCl₂, RhBr₂, RhI₂, etc.), iridium halide (for example, IrF₂, IrCl₂, IrBr₂, IrI₂, etc.), nickel halide (for example, NiF₂, NiCl₂, NiBr₂, NiI₂, etc.), palladium halide (for example, PdF₂, Pdcl₂, PdBr₂, PdI₂, etc.), platinum halide (for example, PtF₂, Ptcl₂, PtBr₂, PtI₂, etc.), copper halide (for example, CuF, CuCl, CuBr, Cul, etc.), silver halide (for example, AgF, AgCl, AgBr, AgI, etc.), and gold halide (for example, AuF, AuCl, AuBr, Aul, etc.).

Examples of the post-transition metal halide may include zinc halide (for example, ZnF₂, ZnCl₂, ZnBr₂, ZnI₂, etc.), indium halide (for example, InI₃, etc.), and tin halide (for example, SnI₂, etc.).

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

Examples of the metalloid halide may include antimony halide (for example, SbCl₅, etc.).

Examples of the metal telluride may include an alkali metal telluride (for example, Li₂Te, Na₂Te, K₂Te, Rb₂Te, Cs₂Te, etc.), an alkaline earth metal telluride (for example, BeTe, MgTe, CaTe, SrTe, BaTe, etc.), a transition metal telluride (for example, 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, etc.), a post-transition metal telluride (for example, ZnTe, etc.), and a lanthanide metal telluride (for example, LaTe, CeTe, PrTe, NdTe, PmTe, EuTe, GdTe, TbTe, DyTe, HoTe, ErTe, TmTe, YbTe, LuTe, etc.).

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

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

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

In one or more embodiments, the emission layer may include a quantum dot.

In one or more embodiments, the emission layer may include a delayed fluorescence material. The delayed fluorescence material may act (e.g., serve) as a host or a dopant in the emission layer.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the emission layer is within these ranges, excellent or suitable light-emission 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 the same as described in connection with Q₁.

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

In one or more 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 each independently be the same as respectively described herein,

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

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

R₃₀₂to R₃₀₅and R₃₁₁to R₃₁₄may each independently be the same as described in connection with R₃₀₁.

In one or more embodiments, the host may include an alkaline earth metal complex, a post-transition metal complex, or any combination thereof. For example, the host may include a Be complex (for example, Compound H55), an Mg complex, a Zn complex, or any combination thereof.

In one or more embodiments, the host may include at least one of Compounds H1 to H128, 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 phosphorescent dopant may include at least one transition metal as a central metal.

The phosphorescent dopant may include a monodentate ligand, a bidentate ligand, a tridentate ligand, a tetradentate ligand, a pentadentate ligand, a hexadentate ligand, or any combination thereof.

The phosphorescent dopant may be electrically neutral.

In an embodiment, the phosphorescent dopant may include an organometallic compound represented by Formula 401:

M(L₄₀₁)_xc1(L₄₀₂)_xc2 Formula 401

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wherein, in Formulae 401 and 402,

M may be a transition metal (for example, iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (T₁), gold (Au), hafnium (Hf), europium (Eu), terbium (Tb), rhodium (Rh), rhenium (Re), or thulium (Tm)),

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

L₄₀₂may be an organic ligand, and xc2 may be 0, 1, 2, 3, or 4, wherein, when xc2 is 2 or more, two or more of L₄₀₂(s) may be identical to or different from each other,

X₄₀₁and X₄₀₂may each independently be nitrogen or carbon,

ring A₄₀₁and ring A₄₀₂may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

T₄₀₁may be a single bond, *—O—*′, *—S—*′, *—C(═O)—*′, *—N(Q₄₁₁)—*′, *—C(Q₄₁₁)(Q₄₁₂)—*′, *—C(Q₄₁₁)═C(Q₄₁₂)—*′, *—C(Q₄₁₁)=*′, or *′C=*′,

X₄₀₃and X₄₀₄may each independently be a chemical bond (for example, a covalent bond or a coordination bond), O, S, N(Q₄₁₃), B(Q₄₁₃), P(Q₄₁₃), C(Q₄₁₃)(Q₄₁₄), or Si(Q₄₁₃)(Q₄₁₄),

Q₄₁₁to Q₄₁₄may each independently be the same as described in connection with Q₁,

R₄₀₁and R₄₀₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₂₀alkyl group unsubstituted or substituted with at least one R_10a, a C₁-C₂₀alkoxy 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 R₁₀a, —Si(Q₄₀₁)(Q₄₀₂)(Q₄₀₃), —N(Q₄₀₁)(Q₄₀₂), —B(Q₄₀₁)(Q₄₀₂), —C(^═O)(Q₄₀₁), —S(═O)₂(Q₄₀₁), or —P(═O)(Q₄₀₁)(Q₄₀₂),

Q₄₀₁to Q₄₀₃may each independently be the same as described in connection with Q₁,

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

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

In an embodiment, in Formula 402, i) X₄₀₁may be nitrogen, and X₄₀₂may be carbon, or ii) each of X₄₀₁and X₄₀₂may be nitrogen.

In one or more embodiments, when xc1 in Formula 401 is 2 or more, two ring A₄₀₁(s) in two or more of L₄₀₁(s) may optionally be linked to each other via T₄₀₂, which is a linking group, and/or two ring A₄₀₂(s) may be optionally be linked to each other via T4o3, which is a linking group (see Compounds PD1 to PD4 and PD7). T₄₀₂and T4o3 are each independently the same as described in connection with T₄₀₁.

L₄₀₂in Formula 401 may be an organic ligand. For example, L₄₀₂may include a halogen group, a diketone group (for example, an acetylacetonate group), a carboxylic acid group (for example, a picolinate group), —C(═O), an isonitrile group, a —CN group, a phosphorus group (for example, a phosphine group, a phosphite group, etc.), or any combination thereof.

The phosphorescent dopant may include, for example, at least one of compounds PD1 to PD39, or any combination thereof:

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Fluorescent Dopant

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

In one or more 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 one or more embodiments, Ar₅₀₁in Formula 501 may be a condensed cyclic group (for example, an anthracene group, a chrysene group, a pyrene group, etc.) in which three or more monocyclic groups are condensed together.

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

For example, the fluorescent dopant may include: at least 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.

In the present specification, the delayed fluorescence material may be selected from compounds capable of emitting delayed fluorescent light based on a delayed fluorescence emission mechanism.

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

In an embodiment, 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 equal to or greater than 0 eV and equal to or less than 0.5 eV. When the difference between the triplet energy level (eV) of the delayed fluorescence material and the singlet energy level (eV) of the delayed fluorescence material satisfies the above-described range, up-conversion from the triplet state to the singlet state of the delayed fluorescence materials may effectively occur, and thus, the luminescence efficiency of the light-emitting device 10 may be improved.

In some embodiments, the delayed fluorescence material may include i) a material including at least one electron donor (for example, a π electron-rich C₃-C₆₀cyclic group, such as a carbazole group) and at least one electron acceptor (for example, a sulfoxide group, a cyano group, and/or a π electron-deficient nitrogen-containing C₁-C₆₀cyclic group), and/or ii) a material including a C₈-C₆₀polycyclic group in which two or more cyclic groups are condensed while sharing boron (B).

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

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Quantum Dot

The emission layer may include a quantum dot.

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 one or more suitable emission wavelengths according to the size of the crystal.

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

The quantum dot may be synthesized by a wet chemical process, a metal organic chemical vapor deposition process, a molecular beam epitaxy process, or any process similar thereto.

The wet chemical process is a method including mixing a precursor material with an organic solvent and then growing a quantum dot crystal particle. When the crystal grows, the organic solvent naturally acts (e.g., serves) as a dispersant coordinated on the surface of the quantum dot crystal and controls the growth of the crystal so that the growth of quantum dot particles can be controlled through a lower cost process, which is easier to perform than vapor deposition methods, such as metal organic chemical vapor deposition (MOCVD) and/or molecular beam epitaxy (MBE),

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 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 an embodiment, 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, and InAlZnP.

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

Examples of the Group semiconductor compound may include: a ternary compound, such as AgInS, AgInS₂, CuInS, CuInS₂, CuGaO₂, AgGaO₂, and/or AgAlO_2;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 include: a single element compound, such as Si and/or Ge; a binary compound, such as SiC and/or SiGe; or any combination thereof.

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

In an embodiment, the quantum dot may have a single structure in which the concentration of each element in the quantum dot is substantially uniform, or a core-shell dual structure. For example, in a quantum dot with a core-shell structure, a material included in the core and a material included in the shell may be different from each other.

The shell of the quantum dot may act (e.g., serve) as a protective layer that prevents or reduces chemical degeneration of the core to maintain semiconductor characteristics, and/or as a charging layer that imparts electrophoretic characteristics to the quantum dot. The shell may be a single layer or a multi-layer. The interface between the core and the shell may have a concentration gradient in which the concentration of an element existing in the shell decreases toward the center of the core.

Examples of the shell of the quantum dot may include an oxide of metal, metalloid, and/or non-metal, a semiconductor compound, or a combination thereof. Examples of the oxide of metal, metalloid, and/or non-metal 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; or any combination thereof. Examples of the semiconductor compound may include, as described herein, 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. For example, the semiconductor compound may include 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.

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

In some embodiments, the quantum dot may be in the form of a spherical particle, a pyramidal particle, a multi-arm particle, a cubic nanoparticle, a nanotube particle, a nanowire particle, a nanofiber particle, or a nanoplate particle.

Because the energy band gap may be adjusted by controlling the size of the quantum dot, light having one or more suitable wavelength bands may be obtained from the emission layer including the quantum dot. Accordingly, by utilizing quantum dots of different sizes, a light-emitting device that emits light of one or more suitable wavelengths may be implemented. For example, the size of the quantum dot may be selected to emit red, green and/or blue light. In some embodiments, the size of the quantum dot may be configured to emit white light by combination of light of one or more suitable 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 (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including different materials.

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

In an embodiment, 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, with the constituting layers of each structure being stacked sequentially from the emission layer in the respective stated order.

The electron transport region (for example, the buffer layer, the hole blocking layer, the electron control layer, and/or the 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 an embodiment, the electron transport region may include a compound represented by Formula 601:

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

wherein, in Formula 601,

Ar601 and 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 R₁₀a, —SI(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁), —S(═O)₂(Q₆₀₁), or —P(═O)(Q₆₀₁)(Q₆₀₂),

Q₆₀₁to Q₆₀₃may each independently be the same as described in connection with Q₁,

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

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

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

In one or more embodiments, Ar₆₀₁in Formula 601 may be a substituted or unsubstituted anthracene group.

In one or more 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 of X₆₁₄to X₆₁₆may be N,

L₆₁₁to L₆₁₃may each independently be the same as described in connection with L_601,

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

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

R₆₁₄to R₆₁₆may each independently be 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, xe1 and xe611 to xe613 in Formulae 601 and 601-1 may each independently be 0, 1, or 2.

The electron transport region may include at least 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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A thickness of the electron transport region may be in a range of about 100 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, a thickness 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 a thickness of the electron transport layer may be in a range of about 100 A 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 region are within these ranges, satisfactory electron transporting 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 Li ion, a Na ion, a K ion, a Rb ion, or a Cs ion, and a metal ion of the alkaline earth metal complex may be a Be ion, a Mg ion, a Ca ion, a Sr ion, or a Ba ion. A ligand coordinated with the metal ion of the alkali metal complex or the alkaline earth-metal complex may include hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, cyclopentadiene, or any combination thereof.

For example, the metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (LiQ) or 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 (e.g., consisting of) a plurality of different materials, or iii) a multi-layered structure including a plurality of layers including 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 include Li, Na, K, Rb, Cs, or any combination thereof. The alkaline earth metal may include Mg, Ca, Sr, Ba, or any combination thereof. The rare earth metal may include 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 be one or more oxides, halides (for example, fluorides, chlorides, bromides, iodides, etc.), and/or tellurides of the alkali metal, the alkaline earth metal, and the rare earth metal, or any combination thereof.

The alkali metal-containing compound may include: one or more alkali metal oxides, such as Li₂O, Cs₂O, and/or K₂O; alkali metal halides, such as LiF, NaF, CsF, KF, Lil, Nal, CsI, and/or KI; or any combination thereof. The alkaline earth metal-containing compound may include an alkaline earth metal compound, such as BaO, SrO, CaO, Ba_xSr_1−xO (wherein x is a real number satisfying the condition of 0<x<1), and/or Ba_xCa_1−xO (wherein x is a real number satisfying the condition of 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 one or more embodiments, the rare earth metal-containing compound may include 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, and Lu₂Te_3.

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 and ii), as a ligand bonded to the metal ion, for example, hydroxyquinoline, hydroxyisoquinoline, hydroxybenzoquinoline, hydroxyacridine, hydroxyphenanthridine, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxyphenyloxadiazole, hydroxyphenylthiadiazole, hydroxyphenylpyridine, hydroxyphenyl benzimidazole, 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 one or more embodiments, the electron injection layer may further include an organic material (for example, a compound represented by Formula 601).

In an embodiment, the electron injection layer may include (e.g., consist of) i) an alkali metal-containing compound (for example, an alkali metal halide), or ii) a) an alkali metal-containing compound (for example, an alkali metal halide); and b) an alkali metal, an alkaline earth metal, a rare earth metal, or any combination thereof. For example, the electron injection layer may be a KI:Yb co-deposited layer, an RbI:Yb co-deposited layer, a LiF:Yb co-deposited 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 uniformly or non-uniformly dispersed in a matrix including the organic material.

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

Second Electrode 150

The second electrode 150 is disposed on the interlayer 130 as described above. The second electrode 150 may be a cathode, which is an electron injection electrode, and as a material for forming the second electrode 150, a metal, an alloy, an electrically conductive compound, or any combination thereof, each having a low work function, may be utilized.

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 a plurality of layers.

Capping Layer

A first capping layer may be located outside the first electrode 110 (e.g., on the side of the first electrode 110 facing oppositely away from the second electrode 150), and/or a second capping layer may be located outside the second electrode 150 (e.g., on the side of the second electrode 150 facing oppositely away from the first electrode 110). In one or 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 the 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 the 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 the stated order.

Light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted (e.g., emitted) toward the outside through the first electrode 110, which is a semi-transmissive electrode or a transmissive electrode, and the first capping layer, or, light generated in the emission layer of the interlayer 130 of the light-emitting device 10 may be extracted (e.g., emitted) toward the outside through the second electrode 150, which is a semi-transmissive electrode or a transmissive electrode, and the second capping layer.

The first capping layer and the second capping layer may increase external luminescence efficiency according to the principle of constructive interference. Accordingly, the light extraction efficiency of the light-emitting device 10 may be increased, so that the luminescence efficiency of the light-emitting device 10 may be improved.

Each of the first capping layer and the second capping layer may include a material having a refractive index of 1.6 or more (at a wavelength of 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 a carbocyclic compound, a heterocyclic compound, an amine group-containing compound, a porphine derivative, a phthalocyanine derivative, a naphthalocyanine derivative, an alkali metal complex, an alkaline earth metal complex, or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may optionally be substituted with a substituent including O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In an embodiment, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.

In one or more embodiments, at least one of the first capping layer or the second capping layer may each independently include a compound represented by Formula 201, a 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 at least one of Compounds HT28 to HT33, at least 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 one or more suitable films. Accordingly, another aspect of the present disclosure provides a film including the organometallic compound represented by Formula 1. The film may be, for example, an optical member (or a light control means) (for example, a color filter, a color conversion member, a capping layer, a light extraction efficiency enhancement layer, a selective light absorbing layer, a polarizing layer, a quantum dot-containing layer, etc.), a light-blocking member (for example, a light reflective layer, a light absorbing layer, etc.), and/or a protective member (for example, an insulating layer, a dielectric layer, etc.).

Electronic Apparatus

The light-emitting device may be included in one or more suitable electronic apparatuses. For example, the electronic apparatus including the light-emitting device may be a light-emitting apparatus, an authentication apparatus, and/or the like.

The electronic apparatus (for example, a light-emitting 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 located in at least one traveling direction of light emitted from the light-emitting device. For example, the light emitted from the light-emitting device may be blue light or white light. The light-emitting device is the same as described above. In an embodiment, the color conversion layer may include a quantum dot. The quantum dot may be, for example, a quantum dot as described herein.

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

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

The color filter may further include a plurality of color filter areas and light-shielding patterns located among the plurality of color filter areas, and the color conversion layer may further include a plurality of color conversion areas and light-shielding patterns located among 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 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. For example, 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. For example, the plurality of color filter areas (or the plurality of color conversion areas) may include quantum dots. In an embodiment, the first area may include red quantum dots, the second area may include green quantum dots, and the third area may not include (e.g., may exclude) quantum dots. The quantum dot is the same as described herein. The first area, the second area, and/or the third area may each further include a scatterer.

In one or more embodiments, the light-emitting device may be to emit a first light, the first area may be to absorb the first light to emit a first-first color light, the second area may be to absorb the first light to emit a second-first color light, and the third area may be to absorb the first light to emit a third-first color light. In this regard, the first-first color light, the second-first color light, and the third-first color light may have different maximum emission wavelengths. For example, the first light may be blue light, the first-first color light may be red light, the second-first color light may be green light, and the third-first color light may be blue light.

The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device as described above. The thin-film transistor may include a source electrode, a drain electrode, and an activation layer, wherein the source electrode or the drain electrode may be electrically connected to the first electrode or the second electrode of the light-emitting device.

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

The activation layer may include crystalline silicon, amorphous silicon, an organic semiconductor, an oxide semiconductor, and/or the like.

The electronic apparatus may further include a sealing portion for sealing the light-emitting device. The sealing portion may be located between the color filter and/or the color conversion layer and the light-emitting device. The sealing portion allows light from the light-emitting device to be extracted to the outside, and concurrently (e.g., simultaneously) prevents or reduces penetration of ambient air and/or moisture into the light-emitting device. The sealing portion may be a sealing substrate including a transparent glass substrate and/or a plastic substrate. The sealing portion may be a thin-film encapsulation layer including at least one layer of an organic layer and/or an inorganic layer. When the sealing portion is a thin-film encapsulating layer, the electronic apparatus may be flexible.

Various suitable functional layers may be additionally disposed on the sealing portion, in addition to the color filter and/or the color conversion layer, according to the usage of the electronic apparatus. The functional layers may include a touch screen layer, a polarizing layer, and/or the like. The touch screen layer may be a pressure-sensitive touch screen layer, a capacitive touch screen layer, or an infrared touch screen layer.

The authentication apparatus may further include, in addition to the light-emitting device as described above, a biometric information collector. The authentication apparatus may be, for example, a biometric authentication apparatus that authenticates an individual by utilizing biometric information of a living body (for example, fingertips, pupils, etc.).

The electronic apparatus may be applied to one or more suitable displays, light sources, lighting apparatuses, personal computers (for example, a mobile personal computer), mobile phones, digital cameras, electronic organizers, electronic dictionaries, electronic game machines, medical instruments (for example, electronic thermometers, sphygmomanometers, blood glucose meters, pulse measurement devices, pulse wave measurement devices, electrocardiogram displays, ultrasonic diagnostic devices, and/or endoscope displays), fish finders, one or more suitable measuring instruments, meters (for example, meters for a vehicle, an aircraft, and/or a vessel), projectors, and/or the like.

Description of FIGS. 2 and 3

FIG. 2 is a cross-sectional view of a light-emitting apparatus 180 according to an embodiment.

The light-emitting apparatus 180 of FIG. 2 includes a substrate 100, a thin-film transistor (TFT), a light-emitting device, and an encapsulation portion 300 that seals 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 disposed 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.

The TFT may be disposed on the buffer layer 210. The TFT may include an activation layer 220, a gate electrode 240, a source electrode 260, and a drain electrode 270.

The activation 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 region, a drain region, and a channel region.

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

An interlayer insulating film 250 may be disposed on the gate electrode 240. The interlayer insulating film 250 may be located between the gate electrode 240 and the source electrode 260 to insulate the gate electrode 240 from the source electrode 260 and between the gate electrode 240 and the drain electrode 270 to insulate the gate electrode 240 from the drain electrode 270.

The source electrode 260 and the drain electrode 270 may be disposed on the interlayer insulating film 250. The interlayer insulating film 250 and the gate insulating film 230 may be formed to expose the source region and the drain region of the activation layer 220, and the source electrode 260 and the drain electrode 270 may be located in contact with the exposed portions of the source region and the drain region of the activation layer 220.

The TFT is electrically connected to a light-emitting device to drive the light-emitting device, and is covered and protected by a passivation layer 280. The passivation layer 280 may include an inorganic insulating film, an organic insulating film, or any combination thereof. A light-emitting device is provided 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 disposed on the passivation layer 280. The passivation layer 280 may be located to expose a certain region of the drain electrode 270 without fully covering the drain electrode 270, and the first electrode 110 may be located to be connected to the exposed region of the drain electrode 270.

A pixel defining layer 290 including an insulating material may be disposed on the first electrode 110. The pixel defining layer 290 may expose a certain region of the first electrode 110, and the interlayer 130 may be formed in the exposed region of the first electrode 110. The pixel defining layer 290 may be a polyimide or polyacrylic organic film. In one embodiment, one or more layers of the interlayer 130 may extend beyond the upper portion of the pixel defining layer 290 in the form of a common layer.

The second electrode 150 may be disposed 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 portion 300 may be disposed on the capping layer 170. The encapsulation portion 300 may be disposed on a light-emitting device to protect the light-emitting device from moisture and/or oxygen. The encapsulation portion 300 may include: an inorganic film including silicon nitride (SiNx), silicon oxide (SiOx), indium tin oxide, indium zinc oxide, or any combination thereof; an organic film including polyethylene terephthalate, polyethylene naphthalate, polycarbonate, polyimide, polyethylene sulfonate, polyoxymethylene, polyarylate, hexamethyldisiloxane, an acrylic resin (for example, polymethyl methacrylate, polyacrylic acid, etc.), an epoxy-based resin (for example, aliphatic glycidyl ether (AGE), etc.), or any combination thereof; or a combination of the inorganic film and the organic film.

FIG. 3 is a cross-sectional view of a light-emitting apparatus 190 according to another embodiment.

The light-emitting apparatus 190 of FIG. 3 is the same as the light-emitting apparatus 180 of FIG. 2, except that a light-shielding pattern 500 and a functional region 400 are additionally disposed on the encapsulation portion 300. The functional region 400 may be i) a color filter area, ii) a color conversion area, or iii) a combination of the color filter area and the color conversion area. In an embodiment, the light-emitting device included in the light-emitting apparatus 190 of FIG. 3 may be a tandem light-emitting device.

Manufacturing Method

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

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

Definition of Terms

The term “C₃-C₆₀carbocyclic group” as used herein refers to a cyclic group consisting of only carbon atoms as ring-forming atoms and having 3 to 60 carbon atoms, and the term “C₁-C₆₀heterocyclic group” as used herein refers to a cyclic group that has, in addition to 1 to 60 carbon atoms, a heteroatom as a ring-forming atom. 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 with each other. For example, the C₁-C₆₀heterocyclic group may have 3 to 61 ring-forming atoms.

The term “cyclic group” as used herein may include both 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 that has 3 to 60 carbon atoms and does not include *—N=*′ as a ring-forming moiety. The term “π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein refers to a heterocyclic group that has 1 to 60 carbon atoms and includes *—N═*′ as a ring-forming moiety.

For example,

the C₃-C₆₀carbocyclic group may be i) a T1 group or ii) a condensed cyclic group in which at least two T1 groups are condensed with each other (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, or an indenoanthracene group),

the C₁-C₆₀heterocyclic group may be i) a T2 group, ii) a condensed cyclic group in which at least two T2 groups are condensed with each other, or iii) a condensed cyclic group in which at least one T2 group and at least one T1 group are condensed with each other (for example, the C₁-C₆₀heterocyclic group may be 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 benzonaphthothiophene 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, etc.),

the π electron-rich C₃-C₆₀cyclic group may be i) a T1 group, ii) a condensed cyclic group in which at least two T1 groups are condensed with each other, iii) a T3 group, iv) a condensed cyclic group in which at least two T3 groups are condensed with each other, or v) a condensed cyclic group in which at least one T3 group and at least one T1 group are condensed with each other (for example, the π electron-rich C₃-C₆₀cyclic group may be the 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 benzonaphthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, etc.),

the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group may be i) a T4 group, ii) a condensed cyclic group in which at least two T4 groups are condensed with each other, iii) a condensed cyclic group in which at least one T4 group and at least one T1 group are condensed with each other, iv) a condensed cyclic group in which at least one T4 group and at least one T3 group are condensed with each other, or v) a condensed cyclic group in which at least one T4 group, at least one T1 group, and at least one T3 group are condensed with one another (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, etc.),

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 terms “the cyclic group,” “the C₃-C₆₀carbocyclic group,” “the C₁-C₆₀heterocyclic group,” “the π electron-rich C₃-C₆₀cyclic group,” or “the π electron-deficient nitrogen-containing C₁-C₆₀cyclic group” as used herein each refer to a group condensed to (e.g., combined together with) any cyclic group, a monovalent group, or a polyvalent group (for example, a divalent group, a trivalent group, a tetravalent group, etc.) according to the structure of a formula for which the corresponding term is used. For example, the “benzene group” may be a benzo group, a phenyl group, a phenylene group, and/or the like, which may be easily understood by one of ordinary skill in the art according to the structure of a 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, and 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 that has 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 isononyl 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 substantially 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 at a main chain (e.g., in the middle) and/or at a terminal end (e.g., the terminus) of the C₂-C₆₀alkyl group, and 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 substantially 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 at a main chain (e.g., in the middle) and/or at a terminal end (e.g., the terminus) of the C₂-C₆₀alkyl group, and 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 substantially 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 Ani is the C₁-C₆₀alkyl group), and 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 cyclic group having 3 to 10 carbon atoms, and examples thereof may include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group (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 substantially the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent saturated monocyclic group that includes, in addition to 1 to 10 carbon atoms, at least one heteroatom, as ring-forming atoms, and 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 substantially 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 the ring thereof and no aromaticity, and 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 substantially the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent cyclic group that includes, in addition to 1 to 10 carbon atoms, at least one heteroatom, as ring-forming atoms, and having at least one carbon-carbon double bond in the cyclic structure thereof. 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-C₁₀heterocycloalkenylene group” as used herein refers to a divalent group having substantially 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 of 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group may 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 include two or more rings, the two or more rings may be condensed with each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system that has, in addition to 1 to 60 carbon atoms, at least one heteroatom, as ring-forming atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having a heterocyclic aromatic system that has, in addition to 1 to 60 carbon atoms, at least one heteroatom, as ring-forming 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 include two or more rings, the two or more rings may be condensed 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 to each other, only carbon atoms (for example, having 8 to 60 carbon atoms) as ring-forming atoms, and no aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). 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, in addition to carbon atoms (for example, having 1 to 60 carbon atoms), further including at least one heteroatom, as ring-forming atoms, and having non-aromaticity in its entire molecular structure (e.g., is not aromatic when considered as a whole). Examples of the monovalent non-aromatic condensed heteropolycyclic group may include a pyrrolyl group, a thiophenyl group, a furanyl group, an indolyl group, a benzoindolyl group, a naphthoindolyl group, an isoindolyl group, a benzoisoindolyl group, a naphthoisoindolyl group, a benzosilolyl group, a benzothiophenyl group, a benzofuranyl group, a dibenzosilolyl group, a dibenzothiophenyl group, a dibenzofuranyl group, an azacarbazolyl group, an azafluorenyl group, an azadibenzosilolyl group, an azadibenzothiophenyl group, an azadibenzofuranyl group, a pyrazolyl group, an imidazolyl group, a triazolyl group, a tetrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, an oxadiazolyl group, a thiadiazolyl group, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a benzoxadiazolyl group, a benzothiadiazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an imidazotriazinyl group, an imidazopyrazinyl group, an imidazopyridazinyl group, an indeno carbazolyl group, an indolocarbazolyl group, a benzofurocarbazolyl group, a benzothienocarbazolyl group, a benzosilolocarbazolyl group, a benzoindolocarbazolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphtho silolyl group, a benzofurodibenzofuranyl group, a benzofurodibenzothiophenyl group, an azaadamantyl group, and a benzothienodibenzothiophenyl 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 the C₆-C₆₀aryl group), and the term “C₆-C₆₀arylthio group” as used herein refers to a monovalent group represented by —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “C₇-C₆₀arylalkyl group” as used herein refers to a monovalent group represented by -A₁₀₄A₁₀₅(wherein A₁₀₄is a C₁-C₅₄alkylene group, and A₁₀₅is a C₆-C₅₉aryl group), and the term “C₂-C₆₀heteroarylalkyl group” as used herein refers to a monovalent group represented by -A₁₀₆A₁₀₇(wherein A₁₀₆is a C₁-C₅₉alkylene group, and A₁₀₇is a C₁-C₅₉heteroaryl group).

The term “R_10a” as used herein refers to:

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, a C₇-C₆₀arylalkyl group, a C₂-C₆₀heteroarylalkyl 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 Q_3,Q₁₁to Q_13,Q₂₁to Q₂₃, and Q₃₁to Q₃₃as used herein may 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, or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, a cyano group, or any combination thereof; 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-C₆₀arylalkyl group; or a C₂-C₆₀heteroarylalkyl 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 refers to a phenyl group, the term “Me” as used herein refers to a methyl group, the term “Et” as used herein refers to an ethyl group, the term “tert-Bu” or “But” as used herein refers to a tert-butyl group, and the term “OMe” as used herein refers to a methoxy group.

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

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

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

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

EXAMPLES
Synthesis Example 1: Synthesis of Compound D31
1. Synthesis of Intermediate Compound 31-3

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Compound 31-2 (1.15 g, 4.15 mmol), Compound 31-1 (620 mg, 3.5 mmol), Pd(dppf)Cl₂(100 mg), and K₂CCh (0.95 g, 6.9 mmol) were dissolved in dioxane (10 mL) and H₂O (2 mL), and then heated at 110° C. under nitrogen gas for 6 hours. After cooling, H₂O (10 mL) was added thereto, and an extraction process was performed thereon three times utilizing EtOAc (10 mL) to collect an organic layer, which was then dried over Na₂SO₄and concentrated with a Rotavapor. The obtained solid was purified by high performance liquid chromatography (HPLC) to thereby obtain Intermediate Compound 31-3 (300 mg, yield of 25%).

2. Synthesis of Intermediate Compound 31-6

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Pd(OAc)₂(0.5 mol %), Pcy₃(1.0 mol %), Compound 31-4 (0.5 mmol), Compound 31-5 (0.75 mmol), K₃PO₄·3H₂O (3.0 eq.), and toluene (2.0 mL) were mixed in a sealed tube, and then heated at 80° C. under nitrogen gas for 10 minutes. After completion of the reaction, an organic layer was separated from the mixture utilizing ethyl acetate and water, and an aqueous layer was extracted from the mixture utilizing ethyl acetate. The separated organic layer was dried over Na₂SO₄, and purified and separated by chromatography utilizing silica gel to thereby obtain Intermediate Compound 31-6.

3. Synthesis of Intermediate Compound 31-7

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9-Borabicyclo[3.3.1]nonane (199.6 mL, 0.5 M in THF) was added to a N₂-purged flask containing Intermediate Compound 31-6 (4.0 g, 16.3 mmol) and stirred at room temperature for 24 hours. Then, Compound 31-3 (7.5 g, 24.8 mmol), Ph₃P (697.9 mg, 2.66 mmol), (Ph₃P)₄Pd (384.3 mg, 0.33 mmol), and aq. 3N NaOH (13.7 mL) were added thereto. After stirring at 60° C. for 22 hours, the mixture was diluted with EtOAc (150 mL), and subjected to an extraction process three times utilizing aq. 1 N H₂SO₄(200 mL). Then, the pH was adjusted to 14, and an aqueous layer was extracted from the mixture three times utilizing EtOAc (150 mL). The extracted organic layer was washed with brine (100 mL), dried over Na₂SO₄, and then concentrated. The obtained material was purified and separated by column chromatography utilizing silica gel utilizing CH₂Cl₂and hexane as development solvents to thereby obtain Intermediate Compound 31-7 (yield of 49%).

4. Synthesis of Intermediate Compound 31-8

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Intermediate Compound 31-7 (2.50 g, 5.77 mmol) and pyridine hydrochloride (3.95 g, 34.1 mmol) were heated at 200° C. for 6 hours. After adding water thereto, the mixture was subjected to an extraction process utilizing ethyl acetate, dried over Na₂SO₄, and then purified and separated by column chromatography utilizing silica gel utilizing CH₂Cl₂and hexane as development solvents to thereby obtain Intermediate Compound 31-8 (1.31 g, yield of 52%).

5. Synthesis of Compound D31

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Acetic acid (30 mL), Intermediate Compound 31-8 (1.06 g, 2.50 mmol), and Pt salt (1.15 g, 2.79 mmol) were added to a 250 mL round-bottom flask, degassed with nitrogen for 30 minutes, and then heated at 130° C. in an oil bath until Intermediate compound 31-8 was completely reacted (for about 4 days). After cooling, the mixture was mixed with heptane, and the mixed solution was stirred and filtered. The obtained solid was purified by silica gel column chromatography utilizing a mixed solvent including dichloromethane (DCM) and ethyl acetate (2% of ethyl acetate in DCM) to thereby obtain Compound D31 (423 mg, yield of 39.9%). The obtained compound was identified by liquid chromatography-mass spectroscopy (LC-MS) as Compound D31.

Preparation Example 1

As a substrate and an anode, a glass substrate with 15 Ω/cm²(1,200 Å) ITO thereon (product of Corning Inc.) was cut to a size of 50 mm×50 mm×0.7 mm, sonicated utilizing isopropyl alcohol and pure water for 5 minutes each, and then washed by irradiation of ultraviolet rays and exposure of ozone thereto for 30 minutes. Then, the glass substrate was mounted on a vacuum deposition apparatus.

2-TNATA was vacuum-deposited on an ITO anode on the glass substrate to form a hole injection layer having a thickness of 200 Å, and NPB was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of 300 A.

CBP (host) and Compound D6 (dopant) were co-deposited at a weight ratio of 94:6 on the hole transport layer to form an emission layer having a thickness of 300 Å.

TPBi was deposited on the emission layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and then, Al was vacuum-deposited on the electron injection layer to form a cathode having a thickness of 1,000 Å, thereby completing the manufacture of an organic light-emitting device.

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Preparation Examples 2 to 5 and Comparative Preparation Examples 1 to 5

Organic light-emitting devices were manufactured in substantially the same manner as in Preparation Example 1, except that compounds shown in Table 2 were respectively utilized instead of Compound D6 in forming respective emission layers.

Evaluation Example 2

The driving voltage, current density, efficiency, and lifespan of each of the organic light-emitting devices manufactured according to Preparation Examples 1 to 5 and Comparative Preparation Examples 1 to 5 were measured by utilizing Keithley SMU 236 and a luminance meter PR_650,and the results are shown in Table 2. In this regard, the driving voltage and luminescence efficiency were measured based on the luminance of 1,000 cd/m².

TABLE 2

Maximum

Emission

Dopant
Driving
luminescence
Luminescence
wave-

com-
voltage
efficiency
efficiency
length

pound
(V)
(cd/A)
(cd/A)
(nm)

Preparation
D6
3.1
47.94
47.93
579

Example 1

Preparation
D13
3.1
47.93
47.92
541

Example 2

Preparation
D22
3.1
47.89
47.87
565

Example 3

Preparation
D27
2.9
46.96
46.94
662

Example 4

Preparation
D49
2.9
46.94
46.92
722

Example 5

Comparative
R2
3.8
29.67
19.58
541

Preparation

Example 1

Comparative
R3
3.6
12.17
12.09
517

Preparation

Example 2

Comparative
R6
3.6
39.07
37.19
593

Preparation

Example 3

Comparative
R7
3.6
38.64
36.65
594

Preparation

Example 4

Comparative
R8
3.6
32.97
29.34
616

Preparation

Example 5

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From Table 2, it was confirmed that the organic light-emitting devices according to Preparation Examples 1 to 5 each had superior driving voltage and luminescence efficiency characteristics to those of the organic light-emitting devices according to Comparative Preparation Examples 1 to 5.

According to the one or more embodiments, the utilization of the organometallic compound may enable the manufacture of a light-emitting device having excellent or suitable efficiency characteristics and a high-quality electronic apparatus including the light-emitting device.

The use of “may” when describing embodiments of the present disclosure refers to “one or more embodiments of the present disclosure”.

As used herein, the terms “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.

Any numerical range recited herein is intended to include all sub-ranges 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.

The electronic apparatus, the display device, and/or any other relevant devices or components according to embodiments of the present invention described herein may be implemented utilizing any suitable hardware, firmware (e.g. an application-specific integrated circuit), software, or a combination of software, firmware, and hardware. For example, the various components of the device may be formed on one integrated circuit (IC) chip or on separate IC chips. Further, the various components of the device may be implemented on a flexible printed circuit film, a tape carrier package (TCP), a printed circuit board (PCB), or formed on one substrate. Further, the various components of the device may be a process or thread, running on one or more processors, in one or more computing devices, executing computer program instructions and interacting with other system components for performing the various functionalities described herein. The computer program instructions are stored in a memory which may be implemented in a computing device using a standard memory device, such as, for example, a random access memory (RAM). The computer program instructions may also be stored in other non-transitory computer readable media such as, for example, a CD-ROM, flash drive, or the like. Also, a person of skill in the art should recognize that the functionality of various computing devices may be combined or integrated into a single computing device, or the functionality of a particular computing device may be distributed across one or more other computing devices without departing from the scope of the embodiments of the present disclosure.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the drawings, it will be understood by those of ordinary skill in the art that one or more suitable 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.

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

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