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

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean Patent Application No. 10-2020-0166929, filed on Dec. 2, 2020, in the Korean Intellectual Property Office, the entire content of which is incorporated herein by reference.

BACKGROUND
1. Field

One or more embodiments of the present disclosure are directed toward an organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device.

2. Description of the Related Art

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

Light-emitting devices may include a first electrode on a substrate, and a hole transport region, an emission layer, an electron transport region, and a second electrode sequentially stacked on the first electrode. Holes provided from the first electrode may move toward the emission layer through the hole transport region, and electrons provided from the second electrode may move toward the emission layer through the electron transport region. Carriers, such as holes and electrons, may then recombine in the emission layer to produce excitons. These excitons transition from an excited state to a ground state to thereby generate light.

SUMMARY

One or more aspects of embodiments of the present disclosure are directed toward a novel organometallic compound, a light-emitting device including the organometallic compound, and an electronic apparatus including the light-emitting device.

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

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

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In Formulae 1, 1A, and 1B,

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

X₁may be C, and a bond between X₁and M may be a coordinate bond,

X₂to X₄, Y₁, and Y₂may each independently be C or N,

one of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a coordinate bond, and other two bonds may each be a covalent bond,

CY₂to CY₄may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

L₁to L₃may each independently be a single bond, *—O—*′, *—S—*′, *—Se—*′, *—S(═O)₂—*′, *—C(R₅)(R₆)—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(═O)(R₅)—*′, or *—Ge(R₅)(R₆)—*′,

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

R₁to R₆and R₁₁may each independently be a group represented by Formula 1A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

at least two groups of R₁in a number of b1, R₂in a number of b2, R₃in a number of b3, R₄in a number of b4, R₅, or R₆may optionally be bound to each other to form 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,

at least one of R₁₁, R₁in a number of b1, R₂in a number of b2, R₃in a number of b3, or R₄in a number of b4 may be a group represented by Formula 1A,

b1 may be 1 or 2,

b2 to b4 may each independently be an integer from 1 to 10,

A₁may be a group represented by Formula 1B,

c1 may be an integer from 1 to 5,

Z₁and Z₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

k1 may be an integer from 0 to 4,

k2 may be an integer from 1 to 7,

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

R_10amay be

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

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

a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, or a C₆-C₆₀arylthio group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₆₀carbocyclic group, a C₁-C₆₀heterocyclic group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, —Si(Q₂₁)(Q₂₂)(Q₂₃), —N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), —P(═O)(Q₂₁)(Q₂₂), or any combination thereof, or

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

wherein Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆alkoxy group, or a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

According to one or more embodiments, a light-emitting device may include a first electrode, a second electrode facing the first electrode, and an interlayer between the first electrode and the second electrode, the interlayer including an emission layer, wherein the light-emitting device may include the organometallic compound represented by Formula 1.

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

BRIEF DESCRIPTION OF THE DRAWINGS

The above and other aspects, features, and advantages of 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 one or more embodiments;

FIG. 2 is a schematic cross-sectional view of an electronic apparatus according to one or more embodiments; and

FIG. 3 is a schematic cross-sectional view of an electronic apparatus according to one or more other embodiments.

DETAILED DESCRIPTION

Reference will now be made in more detail to embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to like elements throughout. In this regard, the present embodiments may have different forms and should not be construed as being limited to the descriptions set forth herein. Accordingly, the embodiments are merely described below, by referring to the figures, to explain aspects of the present description. As used herein, the term “and/or” includes any and all combinations of one or more of the associated listed items. As used herein, expressions such as “at least one of”, “one of”, and “selected from”, when preceding a list of elements, modify the entire list of elements and do not modify the individual elements of the list. For example, the expression “at least one of a, b or c” indicates only a, only b, only c, both a and b, both a and c, both b and c, all of a, b, and c, or variations thereof. Further, 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 singular forms “a,” “an,” and “the” are intended to include the plural forms as well, unless the context clearly indicates otherwise.

It will be further understood that the terms “includes,” “including,” “comprises,” and/or “comprising,” when used in this specification, specify the presence of stated features, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, steps, operations, elements, components, and/or groups thereof.

As used herein, the terms “use,” “using,” and “used” may be considered synonymous with the terms “utilize,” “utilizing,” and “utilized,” respectively.

It will be understood that when an element is referred to as being “on,” “connected to,” or “coupled to” another element, it may be directly on, connected, or coupled to the other element or one or more intervening elements may also be present. When an element is referred to as being “directly on,” “directly connected to,” or “directly coupled to” another element, there are no intervening elements present. 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.

An organometallic compound may be represented by Formula 1:

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

In one or more embodiments, in Formula 1, M may be Pt, Pd, Ni, Au, Ag, or Cu, but embodiments are not limited thereto. For example, M may be Pt, Pd, or Au.

In Formula 1, X₁may be C, and a bond between X₁and M may be a coordinate bond.

In Formula 1, X₂to X₄may each independently be C or N, one of a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a coordinate bond, and other two bonds may each be a covalent bond.

For example, in Formula 1, X₂may be C, X₃may be C, X₄may be N; X₂may be C, X₃may be N, and X₄may be C; or X₂may be N, X₃may be C, and X₄may be C, but embodiments are not limited thereto.

In one or more embodiments, in Formula 1, X₂may be C, X₃may be C, X₄may be N, a bond between X₂and M, a bond between X₃, and M may each be a covalent bond, and a bond between X₄and M may be a coordinate bond.

In Formula 1, Y₁and Y₂may each independently be C or N.

In one or more embodiments, Y₁and Y₂may each be C.

In Formula 1, CY₂to CY₄may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group.

In one or more embodiments, CY₂to 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 dibenzoselenophenegroup, 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-fluoren-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 isooxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a tetrazole group, a benzopyrazole group, a benzimidazole group, a benzotriazole, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, an indazole group, an imidazopyridine group, an imidazopyrimidine group, an imidazopyrazine group, an imidazopyridazine group, a pyrazolopyridine group, a pyrazolopyrimidine group, a pyrazolopyrazine group, a pyrazolopyridazine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

In one or more embodiments, in Formula 1, CY₂may be a group represented by one of Formulae CY2-1 to CY2-9,

CY₃may be a group represented by one of Formulae CY3-1 to CY3-10,

CY₄may be a group represented by one of Formulae CY4-1 to CY4-9, or

any combination thereof:

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wherein, in Formulae CY2-1 to CY2-9, CY3-1 to CY3-10, and CY4-1 to CY4-9,

Z₂₁to Z₂₇, Z₃₁to Z₃₇, and Z₄₁to Z₄₈may each independently be C or N,

Y₂₁, Y₃₁, and Y₄₁may each independently be N, O, S, C, or Si,

X₂to X₄may respectively be understood by referring to the descriptions of X₂to X₄provided herein,

* indicates a binding site to M, and

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

In Formula 1, L₁to L₃may each independently be a single bond, *—O—*′, *—S—*′, *Se—*′, *—S(═O)₂—*′ *—C(R₅)(R₆)—*′, *—C(R₅)═*′, *═C(R₅)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)*′, *—C(═S)—*′, *—C≡C—*′, *—B(R₅)—*′, *—N(R₅)—*′, *—P(R₅)—*′, *—Si(R₅)(R₆)—*′, *—P(═O)(R₅)—*′, or *—Ge(R₅)(R₆)*′,

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

In one or more embodiments, in Formula 1, L₁may be a single bond, L₂may be *—O—*′ or *—S*′, and L₃may be *—N(R₅)*′.

For example, L₁may be a single bond, L₂may be *—O—*′ or *—S—*′, L₃may be *—N(R₅)—*′, and a1 to a3 may each be 1.

In Formula 1, R₁to R₆and R₁₁may each independently be a group represented by Formula 1A, hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

at least one of R₁₁, R₁in a number of b1, R₂in a number of b2, R₃in a number of b3, or R₄in a number of b4 may be a group represented by Formula 1A,

In one or more embodiments, in Formula 1, R₁to R₆and R₁₁may each independently be:

a group represented by Formula 1A, hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₆₀alkyl group or a C₁-C₆alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof,

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, or an indolocarbazolyl group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentacenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, a silolyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an indolyl group, an isoindolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a benzoisoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a benzoquinoxalinyl group, a quinazolinyl group, a benzoquinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a benzothiazolyl group, a benzoisothiazolyl group, a benzoxazolyl group, a benzoisoxazolyl group, a triazolyl group, a tetrazolyl group, a thiadiazolyl group, an oxadiazolyl group, a triazinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a naphthobenzofuranyl group, a naphthobenzothiophenyl group, a naphthobenzosilolyl group, a dibenzocarbazolyl group, a dinaphthofuranyl group, a dinaphthothiophenyl group, a dinaphthosilolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an oxazolopyridinyl group, a thiazolopyridinyl group, a benzonaphthyridinyl group, an azafluorenyl group, an azaspiro-bifluorenyl group, an azacarbazolyl group, an azadibenzofuranyl group, an azadibenzothiophenyl group, an azadibenzosilolyl group, an indenopyrrolyl group, an indolopyrrolyl group, an indenocarbazolyl group, an indolocarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), —P(═O)(Q₃₁)(Q₃₂), or any combination thereof; or

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

wherein Q₁to Q₃and Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₁to Q₃and Q₃₁to Q₃₃provided herein.

In one or more embodiments, in Formula 1, R₁to R₆and R₁₁may each independently be:

a group represented by Formula 1A, hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, or a group represented by one selected from the group consisting of Formulae 9-1 to 9-31 and 10-1 to 10-7:

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wherein, in Formulae 9-1 to 9-31 and 10-1 to 10-7,

“Et” represents an ethyl group,

“i-Pr” represents an iso-propyl group,

“t-Bu” represents a tert-butyl group,

“D” represents deuterium, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, in Formula 1, R₁₁may be a group represented by Formula 1A.

In Formulae 1A and 1B, Z₁and Z₂may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

k1 may be an integer from 0 to 4, and

k2 may be an integer from 1 to 7.

In Formula 1A, A₁may be a group represented by Formula 1B.

In Formula 1A, c1 indicates the number of A₁(s), and c1 may be an integer from 1 to 5.

In some embodiments, the group represented by Formula 1A may be represented by one of Formulae 1A-1 to 1A-14:

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wherein, in Formulae 1A-1 to 1A-14,

Z₁₁to Z₁₅may each independently be understood by referring to the description of Z₁provided herein,

A11 to A13 may each independently be substantially the same as described herein with reference to A1,

A₁may be understood by referring to the description of A₁in Formula 1A, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, in Formulae 1A-1 to 1A-14, Z₁₁to Z₁₅may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, or a tert-hexyl group.

In one or more embodiments, the group represented by Formula 1A may be a group represented by Formula 1A-7-1:

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wherein, in Formula 1A-7-1,

Z₁₂to Z₁₄may each independently be understood by referring to the description of Z₁provided herein,

Z₂₁and Z₂₂may each independently be understood by referring to the description of Z₂provided herein,

k21 and k22 may each independently be an integer from 1 to 7, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, in Formula 1A-7-1,

Z₁₂to Z₁₄may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, or a tert-hexyl group, and

Z₂₁and Z₂₂may each be hydrogen.

In one or more embodiments, in Formula 1, at least one of R₁in a number of b1, R₂in a number of b2, R₃in a number of b3, R₄in a number of b4, R₅, R₆, or R₁₁may be deuterium, —CH₂D, —CHD₂, —CD₃, a phenyl group substituted with at least one deuterium, or a group represented by one of Formulae 10-2 to 10-7:

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wherein, in Formulae 10-2 to 10-7,

“D” represents deuterium, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, a moiety represented by

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in Formula 1 may be a group represented by Formula L1-1 or Formula L1-2:

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wherein, in Formulae 1-1 and L1-2,

R_1ato R_1dmay each independently be understood by referring to the description of R₁provided herein,

R_2ato R_2cmay each independently be understood by referring to the description of R₂provided herein,

M, A₁, c1, Z₁, and k1 may respectively be understood by referring to the descriptions of M, A₁, c1, Z₁, and k1 provided herein, and

* indicates a binding site to L₂.

In one or more embodiments, a moiety represented by

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in Formula 1 may be a group represented by Formula L2-1 or Formula L2-2:

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

R_3aand R_3bmay each independently be understood by referring to the description of R₃provided herein,

R_4ato R_4emay each independently be understood by referring to the description of R₄provided herein,

R_5ato R_5dmay each independently be understood by referring to the description of R_10aprovided herein,

M may be understood by referring to the description of M in Formula 1, and

* indicates a binding site to L₂.

In one embodiment, the organometallic compound may be represented by any one of Formulae 1-1 to 1-4:

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wherein, in Formulae 1-1 to 1-4,

M, L₂, A₁, c1, Z₁, and k1 may respectively be understood by referring to the descriptions of M, L₂, A₁, c1, Z₁, and k1 provided herein,

R_1ato R_1dmay each independently be understood by referring to the description of R₁provided herein,

R_2ato R_2cmay each independently be understood by referring to the description of R₂provided herein,

R_3aand R_3bmay each independently be understood by referring to the description of R₃provided herein,

R_4ato R_4emay each independently be understood by referring to the description of R₄provided herein, and

R_5ato R_5dmay each independently be understood by referring to the description of R_10aprovided herein.

In one or more embodiments, in Formulae 1-1 to 1-4, R_1ato R_1d, R_2ato R_2c, R_3a, R_3b, R_4ato R_4e, and Ra to R_5dmay each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a methyl group, an ethyl group, a propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neo-pentyl group, an iso-pentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an iso-hexyl group, a sec-hexyl group, a tert-hexyl group, or a group represented by one selected from the group consisting of Formulae 9-1 to 9-31 and 10-1 to 10-7:

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wherein, in Formulae 9-1 to 9-31 and 10-1 to 10-7,

“Et” represents an ethyl group,

“i-Pr” represents an iso-propyl group,

“t-Bu” represents a tert-butyl group,

“D” represents deuterium, and

* indicates a binding site to an adjacent atom.

In some embodiments, in Formula 1-1 to 1-4, at least one of R_1ato R_1d, R_2ato R_2c, R_3a, R_3b, R_4ato R_4e, or R_5ato R_5dmay be represented by deuterium, —CH₂D, —CHD₂, —CD₃, or a group represented by one of Formulae 10-1 to 10-7:

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wherein, in Formulae 10-1 to 10-7,

“D” represents deuterium, and

* indicates a binding site to an adjacent atom.

In one or more embodiments, the organometallic compound may be one of Compounds BD01 to BD210:

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wherein, in Compounds BD01 to BD210, D₄indicates substitution with four deuteriums (D).

In the organometallic compound represented by Formula 1, a triplet (T1) energy of A₁group represented by Formula 1B may be about 0.01 eV or higher than a triplet energy of another moiety in the molecule. Because a bulky group such as a group represented by Formula 1A is substituted on the ligand, the group represented by Formula 1A may induce steric hindrance to thereby suppress or reduce substituent rotation and maintain structural rigidity of the molecule. Accordingly, when the organometallic compound is used as a dopant, intermolecular interaction between homogeneous or heterogeneous molecules may be suppressed or reduced to thereby suppress or reduce self-aggregation or aggregation with a host material. Due to such a structural characteristic, two types (or kinds) of energy transfer, including metal to ligand charge transfer (³MLCT) and intraligand charge transfer (³ILCT), may be activated. Accordingly, a light-emitting device including the organometallic compound may have improved efficiency and lifespan.

In addition, the organometallic compound represented by Formula 1 may include at least one carbon-deuterium (C-D) bond. A C-D bond may have a short bonding length, as compared with a C—H bond, and the binding energy may increase about 13 kcal/mol. Thus, the internal energy of the organometallic compound may decrease, and stability of the complex molecule may improve. Accordingly, upon energy transition in the molecule, nonradiative transition may be prevented or reduced to thereby improve a photoluminescence quantum yield (PLQY).

In the organometallic compound represented by Formula 1, a carbene-containing ligand and the group represented by Formula 1A may be disposed (e.g., positioned) to be substantially perpendicular to a carbene-containing core. Thus, the overall molecular conjugation may be broken or decreased. Accordingly, an emission wavelength may be blue-shifted, and thus, when the organometallic compound is applied to a light-emitting device, the light-emitting device may emit deep-blue light. Accordingly, the light-emitting device may exhibit improved colorimetric purity and color reproducibility.

Therefore, an electronic device, e.g., a light-emitting device, including the organometallic compound may have a low driving voltage, high efficiency, long lifespan, and/or high colorimetric purity.

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 Examples described herein.

At least one of the organometallic compounds represented by Formula 1 may be used in a light-emitting device (e.g., an organic light-emitting device).

According to one or more embodiments, a light-emitting device may include a first electrode; a second electrode facing the first electrode; an interlayer located between the first electrode and the second electrode and including an emission layer and the organometallic compound represented by Formula 1.

In some embodiments,

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

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

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

In one or more embodiments, the organometallic compound may be included in an interlayer, e.g., an emission layer, of the light-emitting device.

In one or more embodiments, the emission layer may include a host and a dopant, and the dopant may include the organometallic compound. For example, the organometallic compound may serve as an emission layer dopant. A content (e.g., amount) of the dopant in the emission layer may be in a range of about 0.1 parts to about 49.99 parts by weight, based on 100 parts by weight of the emission layer.

The emission layer may emit red light, green light, blue light, and/or white light. In some embodiments, the emission layer may emit blue light. Blue light having a maximum emission wavelength in a range of about 440 nm to about 475 nm may be emitted from the emission layer. A bottom emission-based CIE_xcolor-coordinate of the blue light may be in a range of about 0.13 to about 0.14, and a CIE_ycolor-coordinate may be in a range of about 0.06 to about 0.25, but embodiments are not limited thereto.

In one or more embodiments, the host may include different types (or kinds) of hosts. In some embodiments, the host may include a hole transporting host and an electron transporting host.

In one or more embodiments, the host may include an electron transporting host represented by Formula 2, a hole transporting host represented by Formula 3, or any combination thereof:

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wherein, in Formulae 2 and 3,

X₂₁may be N or C-(L₂₄)_a24-(R₂₄)_b24, X₂₂may be N or C-(L₂₅)_a25-(R₂₅)_b25, and X₂₃may be N or C-(L₂₆)_a26-(R₂₆)_b26,

X₃₁may be selected from a single bond, O, S, N(R₃₄), C(R₃₄)(R₃₅), and Si(R₃₄)(R₃₅),

CY₃₁and CY₃₂may each independently be a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group,

L₂₁to L₂₆and L₃₁to L₃₃may 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,

a21 to a26 and a31 to a33 may each independently be an integer from 0 to 5,

R₂₁to R₂₆and R₃₁to R₃₅may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

b21 to b26, b31 to b33, n31, and n32 may each independently be an integer from 1 to 5, and

R_10aand Q₁to Q₃may respectively be understood by referring to the descriptions of R_10aand Q₁to Q₃provided herein.

In Formula 2, when a21 is 0, (L₂₁)_a21may be a single bond, when a22 is 0, (L₂₂)_a22may be a single bond, when a23 is 0, (L₂₃)_a23may be a single bond, when a24 is 0, (L₂₄)_a24may be a single bond, when a25 is 0, (L₂₅)_a25may be a single bond, and when a26 is 0, (L₂₆)_a26may be a single bond.

In some embodiments, in Formula 2, a21 to a26 may each independently be 0 or 1.

In one or more embodiments, in Formula 2, L₂₁to L₂₆may each independently be a phenylene group unsubstituted or substituted with at least one R_10a.

In some embodiments, in Formula 3, CY₃₁and CY₃₂may 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 dibenzoselenophenegroup, 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-fluoren-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 isooxazole 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, but embodiments are not limited thereto.

In one or more embodiments, in Formulae 2 and 3, R₂₁to R₂₆and R₃₁to R₃₅may each independently be:

hydrogen, deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, or a nitro group;

a C₁-C₆₀alkyl group or a C₁-C₆₀alkoxy group, each unsubstituted or substituted with deuterium, —F, —Cl, —Br, —I, —CH₂D, —CHD₂, —CD₃, —CH₂F, —CHF₂, —CF₃, a hydroxyl group, a cyano group, a nitro group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, an adamantyl group, a norbornyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof;

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

wherein Q₁to Q₃and Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₁to Q₃and Q₃₁to Q₃₃provided herein.

In some embodiments, in Formula 2, R₂₁to R₂₆may each independently be:

a phenyl group or a carbazolyl group, each unsubstituted or substituted with a C₁-C₁₀alkyl group, a phenyl group, a carbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), or any combination thereof; or

—Si(Q₁)(Q₂)(Q₃),

wherein Q₁to Q₃and Q₃₁to Q₃₃may respectively be understood by referring to the descriptions of Q₁to Q₃and Q₃₁to Q₃₃provided herein.

In one or more embodiments, in Formula 2, at least one of R₂₁in a number of b21, R₂₂in a number of b22, or R₂₃in a number of b23 may be: a phenyl group, a carbazolyl group, each unsubstituted or substituted with a phenyl group, a carbazolyl group, Si(Q₁)(Q₂)(Q₃), or any combination thereof.

In one or more embodiments, the electron transporting host represented by Formula 2 may include at least one deuterium. In some embodiments, at least one selected from R₂₁to R₂₆may be deuterium, or at least one selected from L₂₁to L₂₆and R₂₁to R₂₆may be substituted with at least one deuterium.

In one or more embodiments, the hole transporting host represented by Formula 3 may include at least one deuterium. In some embodiments, at least one selected from R₃₁to R₃₅may be deuterium, or at least one selected from L₃₁to L₃₃and R₃₁to R₃₅may be substituted with at least one deuterium.

For example, the electron transporting host represented by Formula 2 may be one of Compounds ETH1 to ETH16, and the hole transporting host represented by Formula 3 may be one of Compounds HTH1 to HTH16, but embodiments are not limited thereto:

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The electron transporting host represented by Formula 2 and the hole transporting host represented by Formula 3 may form an exciplex.

In one or more embodiments, the host may include the electron transporting host represented by Formula 2 and the hole transporting host represented by Formula 3. In this embodiment, the electron transporting host and the hole transporting host may form an exciplex. Thus, when the electron transporting host and the hole transporting host are used as co-hosts in the emission layer, a light-emitting device may have high efficiency and long lifespan.

A content ratio of the electron transporting host to the hole transporting host in the emission layer may be in a range of about 90:10 to about 10:90, for example, about 80:20 to about 20:80, or for example, about 70:30 to about 30:70, but embodiments are not limited thereto.

In one or more embodiments, the dopant may further include a delayed fluorescent material.

For example, the delayed fluorescent material may be a compound represented by Formula 4:

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wherein, in Formula 4,

W₄₁may be O, S, N(R_41a) or C(R_41a)(R_41b), W₄₂may be O, S, N(R_42a), or C(R_42a)(R_42b), W₄₃may be O, S, N(R_43a), or C(R_43a)(R_43b), and W₄₄may be O, S, N(R_44a), or C(R_44a)(R_44b),

R_41a, R_41b, R_42a, R_42b, R_43a, R_43b, R_44a, R_44b, R_45a, R_45b, R₄₆, R₄₇, R₄₈, and R₄₉may each independently be hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, a C₁-C₆₀alkyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkenyl group unsubstituted or substituted with at least one R_10a, a C₂-C₆₀alkynyl group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀alkoxy group unsubstituted or substituted with at least one R_10a, a C₃-C₆-carbocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a, a C₁-C₆₀aryloxy group unsubstituted or substituted with at least one R_10a, a C₆-C₆₀arylthio group unsubstituted or substituted with at least one R_10a, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂), —C(═O)(Q₁), —S(═O)₂(Q₁), or —P(═O)(Q₁)(Q₂),

b46 and b49 may each independently be an integer from 1 to 4,

b47 and b48 may each independently be an integer from 1 to 3,

R_10aand Q₁to Q₃may respectively be understood by referring to the descriptions of R_10aand Q₁to Q₃provided herein.

An excited triplet energy level of the organometallic compound represented by Formula 1 and an excited triplet energy level of the compound represented by Formula 4 may be small such that dexter energy transition may occur.

A difference between an excited triplet energy level of the compound represented by Formula 4 and an excited singlet energy level thereof may be very small (e.g., about 0.3 eV or less). Thus, due to reverse intersystem crossing (RISC) mechanism, excitons of the excited triplet energy may be transferred to excitons of the excited singlet energy.

Accordingly, in a case of a light-emitting device further including the compound represented by Formula 4 according to one or more embodiments, excited triplet excitons transitioned from the organometallic compound may not be quenched and may be transitioned to an excited singlet state, and then transitioned to a ground state. Thus, an (organic) light-emitting device having high efficiency and long lifespan may be manufactured.

In one or more embodiments, the compound represented by Formula 4 may be a fluorescence emitter. For example, the compound represented by Formula 4 may be a delayed fluorescence dopant.

In one or more embodiments, W₄₁may be N(R_41a), W₄₂may be N(R_42a), W₄₃may be N(R_43a), or W₄₄may be N(R_44a). For example, W₄₁may be N(R_41a), and W₄₂may be N(R_42a). For example, W₄₁may be N(R_41a), W₄₂may be N(R_42a), and W₄₃may be N(R_43a). For example, W₄₁may be N(R_41a), W₄₂may be N(R_42a), and W₄₄may be N(R_44a). For example, W₄₂may be N(R_42a), W₄₃may be N(R_43a), and W₄₄may be N(R_44a). For example, W₄₁may be N(R_41a), W₄₂may be N(R_42a), W₄₃may be N(R_43a), and W₄₄may be N(R_44a).

In one or more embodiments, R₄₇and R₄₈may each be —N(Q₁)(Q₂), wherein Q₁and Q₂may each independently be a C₆-C₆₀aryl group unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₁₀alkyl group, a phenyl group, a biphenyl group, or any combination thereof, and b47 and b48 may each be 1.

For example, the compound represented by Formula 4 may be one of Compounds DFD1 to DFD12, but embodiments are not limited thereto:

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In one or more embodiments, the light-emitting device may include at least one of a first capping layer located outside the first electrode or a second capping layer located outside the second electrode. In some embodiments, the at least one of the first capping layer or the second capping layer may include the organometallic compound represented by Formula 1. The first capping layer and the second capping layer may respectively be understood by referring to the descriptions of the first capping layer and the second capping layer provided herein.

In some embodiments, the at least one of the first capping layer or the second capping layer may have a refractive index of about 1.6 or higher at a wavelength of 589 nanometers (nm).

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

For example, Compound BD01 may only be included in the interlayer as the organometallic compound. In this embodiment, Compound BD01 may be included in the emission layer of the light-emitting device. In some embodiments, Compounds BD01 and BD02 may be included in the interlayer as the organometallic compounds. In this embodiment, Compounds BD01 and BD02 may be included in the same layer (for example, both Compounds BD01 and BD02 may be included in an emission layer) or in different layers (for example, Compound BD01 may be included in an emission layer, and Compound BD02 may be included in an electron transport region).

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

Description of FIG. 1

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

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

First Electrode 110

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

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

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

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

Interlayer 130

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

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

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

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

Hole Transport Region in Interlayer 130

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

The hole transport region may include a hole injection layer, a hole transport layer, an emission auxiliary layer, an electron blocking layer, or a combination thereof.

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

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

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wherein, in Formulae 201 and 202,

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

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

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

xa5 may be an integer from 1 to 10,

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

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

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

na1 may be an integer from 1 to 4.

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

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

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

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

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

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

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

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

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

In some embodiments, the hole transport region may include one of Compounds HT1 to HT46, m-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly(4-styrenesulfonate (PANI/PSS), or any combination thereof:

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

The emission auxiliary layer may increase light emission efficiency by compensating for an optical resonance distance according to the wavelength of light emitted by an emission layer. The electron blocking layer may reduce or eliminate the flow of electrons from an electron transport region. The emission auxiliary layer and the electron blocking layer may each independently include any of the aforementioned materials.

p-Dopant

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

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

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

In some embodiments, the p-dopant may include a quinone derivative, a cyano group-containing compound, elements EL1 and/or EL2-containing compound, or any combination thereof.

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

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

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wherein, in Formula 221,

R₂₂₁to R₂₂₃may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aor a C₁-C₆heterocyclic 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 independently 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 elements EL1 and/or EL2-containing compound, element EL1 may be metal, metalloid, or a combination thereof, and element EL2 may be non-metal, metalloid, or a combination thereof.

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

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

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

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

Examples of the metal oxide may include tungsten oxide (e.g., WO, W₂O₃, WO₂, WO₃, W₂O₅, and/or the like), vanadium oxide (e.g., VO, V₂O₃, VO₂, V₂O₅, and/or the like), molybdenum oxide (MoO, Mo₂O₃, MoO₂, MoO₃, Mo₂O₅, and/or the like), rhenium oxide (e.g., ReO₃, and/or the like), and the like.

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

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

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

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

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

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

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

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

Emission Layer in Interlayer 130

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

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

In one or more embodiments, the host may include the electron transporting host represented by Formula 2, the hole transporting host represented by Formula 3, or any combination thereof.

The dopant may include the organometallic compound represented by Formula 1. In some embodiments, the dopant may further include the compound represented by Formula 4.

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

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

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

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

Host

The host may include the electron transporting host represented by Formula 2, the hole transporting host represented by Formula 3, or the 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 be understood by referring to the description of Q₁provided herein.

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

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

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

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

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

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

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

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

xb2 to xb4 may each be understood by referring to the descriptions of xb1 provided herein, and

R₃₀₂to R₃₀₅and R₃₁₁to R₃₁₄may each be understood by referring to the descriptions of R₃₀₁provided herein.

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

In some embodiments, the host may include one of Compounds H1 to H124, 9,10-di(2-naphthyl)anthracene (ADN), 2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN), 9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN), 4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene (mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), or any combination thereof:

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Phosphorescent Dopant

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

Fluorescent Dopant

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

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

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wherein, in Formula 501,

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

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

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

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

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

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

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Delayed Fluorescence Material

The emission layer may include a delayed fluorescence material.

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

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

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

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

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

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Quantum Dot

The emission layer may include quantum dots.

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

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

Quantum dots may be synthesized by a wet chemical process, an organic metal chemical vapor deposition process, a molecular beam epitaxy process, or any similar suitable process.

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

The quantum dot may include a group II-VI semiconductor compound; a group III-V semiconductor compound; a group III-VI semiconductor compound; a group I-III-VI semiconductor compound; a group IV-VI semiconductor compound; a group IV element, a group IV 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; and 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, GalnNSb, GaInPAs, GalnPSb, InAlNP, InAlNAs, InAlNSb, InAlPAs, and/or InAlPSb; and any combination thereof. In some embodiments, the group III-V semiconductor compound may further include a group II element. Examples of the group III-V semiconductor compound further including the group II element may include InZnP, InGaZnP, InAlZnP, and the like.

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

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

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

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

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

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

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

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

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

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

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

Electron Transport Region in Interlayer 130

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

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

In some embodiments, the electron transport region may have an electron transport layer/electron injection layer structure, a hole blocking layer/electron transport layer/electron injection layer structure, an electron control layer/electron transport layer/electron injection layer structure, or a buffer layer/electron transport layer/electron injection layer structure, wherein the layers of each structure are sequentially stacked on the emission layer in each stated order.

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

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

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

wherein, in Formula 601,

Ar₆₀₁and L₆₀₁may each independently be a C₃-C₆₀carbocyclic group unsubstituted or substituted with at least one R_10aand/or a C₁-C₆₀heterocyclic group unsubstituted or substituted with at least one R_10a,

xe11 may be 1, 2, or 3,

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

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

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

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

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

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

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

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

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wherein, in Formula 601-1,

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

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

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

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

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

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

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

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The thickness of the electron transport region may be in a range of about 50 Angstroms (Å) to about 5,000 Å, for example, about 100 Å to about 4,000 Å. When the electron transport region includes a buffer layer, a hole blocking layer, an electron control layer, an electron transport layer, or any combination thereof, the thicknesses of the buffer layer, the hole blocking layer, or the electron control layer may each independently be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å, and the thickness of the electron transport layer may be in a range of about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thicknesses of the buffer layer, the hole blocking layer, the electron control layer, the electron transport layer, and/or the electron transport layer are each within these ranges, excellent (or improved) electron transport characteristics may be obtained without a substantial increase in driving voltage.

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

The metal-containing material may include an alkali metal complex, an alkaline earth metal complex, or any combination thereof. A metal ion of the alkali metal complex may be a lithium (Li) ion, a sodium (Na) ion, a potassium (K) ion, a rubidium (Rb) ion, and/or a cesium (Cs) ion. A metal ion of the alkaline earth metal complex may be a beryllium (Be) ion, a magnesium (Mg) ion, a calcium (Ca) ion, a strontium (Sr) ion, and/or a barium (Ba) ion. A ligand coordinated with the metal ion of the alkali metal complex and the alkaline earth metal complex may each independently be 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, e.g., Compound ET-D1 (LiQ) and/or Compound ET-D2:

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The electron transport region may include an electron injection layer that facilitates 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 including (e.g., consisting of) a single layer including (e.g., consisting of) a single material, ii) a single-layered structure including (e.g., consisting of) a single layer including a plurality of different materials, or iii) a multi-layered structure having a plurality of layers including a plurality of different materials.

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

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

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

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

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

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

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

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

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

Second Electrode 150

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

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

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

Capping Layer

A first capping layer may be located outside the first electrode 110, and/or a second capping layer may be located outside the second electrode 150. In some embodiments, the light-emitting device 10 may have a structure in which the first capping layer, the first electrode 110, the interlayer 130, and the second electrode 150 are sequentially stacked in this stated order, a structure in which the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order, or a structure in which the first capping layer, the first electrode 110, the interlayer 130, the second electrode 150, and the second capping layer are sequentially stacked in this stated order.

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

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

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

The first capping layer and the second capping layer may each independently be a capping layer including an organic material, an inorganic capping layer including an inorganic material, and/or a 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 carbocyclic compound(s), heterocyclic compound(s), amine group-containing compound(s), porphine derivative(s), phthalocyanine derivative(s), naphthalocyanine derivative(s), alkali metal complex(es), alkaline earth metal complex(es), or any combination thereof. The carbocyclic compound, the heterocyclic compound, and the amine group-containing compound may each independently be optionally substituted with a substituent of O, N, S, Se, Si, F, Cl, Br, I, or any combination thereof. In some embodiments, at least one of the first capping layer or the second capping layer may each independently include an amine group-containing compound.

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

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

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Electronic Apparatus

The light-emitting device may be included in one or more suitable electronic apparatuses. In some embodiments, an electronic apparatus including the light-emitting device may be an emission apparatus and/or an authentication apparatus.

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

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

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

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

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

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

The electronic apparatus may further include a thin-film transistor, in addition to the light-emitting device. The thin-film transistor may include a source electrode, a drain electrode, and an active layer, wherein one of the source electrode and the drain electrode may be electrically connected (e.g., electrically coupled) to one of the first electrode and 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 active layer may include a crystalline silicon, an amorphous silicon, an organic semiconductor, and/or an oxide semiconductor.

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

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

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

The electronic apparatus may be applicable to various suitable displays, an optical source, lighting, a personal computer (e.g., a mobile personal computer), a cellphone, a digital camera, an electronic note, an electronic dictionary, an electronic game console, a medical device (e.g., an electronic thermometer, a blood pressure meter, a glucometer, a pulse measuring device, a pulse wave measuring device, an electrocardiograph recorder, an ultrasonic diagnosis device, an endoscope display device), a fish finder, various measurement devices, gauges (e.g., gauges of an automobile, an airplane, a ship), a projector, without limitation.

Descriptions of FIGS. 2 and 3

FIG. 2 is a schematic cross-sectional view of a light-emitting apparatus according to one or more embodiments.

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

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

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

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

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

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

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

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

The first electrode 110 may be on the passivation layer 280. The passivation layer 280 may not fully cover the drain electrode 270 and may expose a specific or set area of the drain electrode 270, and the first electrode 110 may be disposed to connect (e.g., to electrically couple) to the exposed drain electrode 270.

A pixel-defining film 290 may be on the first electrode 110. The pixel-defining film 290 may expose a specific or set area of the first electrode 110, and the interlayer 130 may be formed in the exposed area. The pixel-defining film 290 may include one or more suitable organic insulating materials, inorganic insulating materials, and/or organic/inorganic composite insulating materials. In some embodiments, the pixel-defining film 290 may be a polyimide and/or a polyacryl organic film. In one or more embodiments, some or more layers of the interlayer 130 may extend to the upper portion of the pixel-defining film 290 and may be disposed in the form of a common layer.

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

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

FIG. 3 is a schematic cross-sectional view of another light-emitting apparatus according to one or more embodiments.

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

Manufacturing Method

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

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

General Definitions of Terms

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

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

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

In some embodiments,

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

the C₁-C₆₀heterocyclic group may be i) a T2 group, ii) a group in which at least two T2 groups are condensed, or iii) a group in which at least one T2 group is condensed with at least one T1 group (for example, 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 benzonapthothiophene group, a benzonaphthosilole group, a benzofurodibenzofuran group, a benzofurodibenzothiophene group, a benzothienodibenzothiophene group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, an oxadiazole group, a thiazole group, an isothiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzoisoxazole group, a benzothiazole group, a benzoisothiazole group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a benzoisoquinoline group, a quinoxaline group, a benzoquinoxaline group, a quinazoline group, a benzoquinazoline group, a phenanthroline group, a cinnoline group, a phthalazine group, a naphthyridine group, an imidazopyridine group, an imidazopyrimidine group, an imidazotriazine group, an imidazopyrazine group, an imidazopyridazine group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, and/or the like),

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

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

wherein the T1 group may be a cyclopropane group, a cyclobutane group, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclooctane group, a cyclobutene group, a cyclopentene group, a cyclopentadiene group, a cyclohexene group, a cyclohexadiene group, a cycloheptene group, an adamantane group, a norbornane (or 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, and/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, and/or a tetrazine group,

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

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

Examples of the monovalent C₃-C₆₀carbocyclic group and the monovalent C₁-C₆heterocyclic group may include a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group. Examples of the divalent C₃-C₆₀carbocyclic group and the divalent C₁-C₆₀heterocyclic group may include a C₃-C₁₀cycloalkylene group, a C₁-C₁₀heterocycloalkylene group, a C₃-C₁₀cycloalkenylene group, a C₁-C₁₀heterocycloalkenylene group, a C₆-C₆₀arylene group, a C₁-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

The term “C₁-C₆₀alkyl group” as used herein refers to a linear or branched aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and examples thereof include a methyl group, an ethyl group, an n-propyl group, an iso-propyl 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 iso-hexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an iso-heptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an iso-octyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an iso-nonyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an iso-decyl group, a sec-decyl group, and a tert-decyl group. The term “C₁-C₆₀alkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀alkyl group.

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

The term “C₂-C₆₀alkynyl group” as used herein refers to a monovalent hydrocarbon group having at least one carbon-carbon triple bond in the middle and/or at either terminus of the C₂-C₆₀alkyl group. Examples thereof include an ethynyl group and a propynyl group. The term “C₂-C₆alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₆₀alkynyl group.

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

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group including 3 to 10 carbon atoms. Examples of the C₃-C₁₀cycloalkyl group as used herein include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantyl group, a norbornyl (bicyclo[2.2.1]heptyl) group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, and a bicyclo[2.2.2]octyl group. The term “C₃-C₁₀cycloalkylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkyl group.

The term “C₁-C₁₀heterocycloalkyl group” as used herein refers to a monovalent cyclic group including at least one heteroatom other than carbon atoms as a ring-forming atom and having 1 to 10 carbon atoms. Examples thereof include a 1,2,3,4-oxatriazolidinyl group, a tetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent cyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring, and is not aromatic. Examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent cyclic group including at least one heteroatom other than carbon atoms as a ring-forming atom, 1 to 10 carbon atoms, and at least one double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group include a 4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Examples of the C₆-C₆₀aryl group include a phenyl group, a pentalenyl group, a naphthyl group, an azulenyl group, an indacenyl group, an acenaphthyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenyl group, a heptalenyl group, a naphthacenyl group, a picenyl group, a hexacenyl group, a pentacenyl group, a rubicenyl group, a coronenyl group, and an ovalenyl group. The term “C₆-C₆₀arylene group” as used herein refers to a divalent group having the same structure as the C₆-C₆₀aryl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each independently include two or more rings, the respective rings may be fused.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having a heterocyclic aromatic system further including at least one heteroatom other than carbon atoms as a ring-forming atom and 1 to 60 carbon atoms. Examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, 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, and a naphthyridinyl group. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having the same structure as the C₁-C₆₀heteroaryl group. When the C₁-C₆heteroaryl group and the C₁-C₆₀heteroarylene group each independently include two or more rings, the respective rings may be fused.

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group that has two or more rings condensed and only carbon atoms (e.g., 8 to 60 carbon atoms) as ring forming atoms, wherein the molecular structure when considered as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed polycyclic group include an indenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, an indenophenanthrenyl 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 that has two or more condensed rings and at least one heteroatom other than carbon atoms (e.g., 1 to 60 carbon atoms), as a ring-forming atom, wherein the molecular structure when considered as a whole is non-aromatic. Examples of the monovalent non-aromatic condensed heteropolycyclic group include a 9,10-dihydroacridinyl group and a 9H-xanthenyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having substantially the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₆-C₆₀aryloxy group” as used herein refers to a monovalent group represented by —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group). The term “C₆-C₆₀arylthio group” as used herein refers to a monovalent group represented by —SA₁₀₃(wherein A103 is the C₆-C₆₀aryl group).

The term “R_10a” as used herein may be:

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

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

Q₁to Q₃, Q₁₁to Q₁₃, Q₂₁to Q₂₃, and Q₃₁to Q₃₃may each independently be hydrogen; deuterium; —F; —Cl; —Br; —I; a hydroxyl group; a cyano group; a nitro group; a C₁-C₆alkyl group; a C₂-C₆₀alkenyl group; a C₂-C₆₀alkynyl group; a C₁-C₆₀alkoxy group; or a C₃-C₆₀carbocyclic group or a C₁-C₆₀heterocyclic group, each unsubstituted or substituted with deuterium, —F, a cyano group, a C₁-C₆₀alkyl group, a C₁-C₆₀alkoxy group, a phenyl group, a biphenyl group, or any combination thereof.

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, and any combination thereof.

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

The term “biphenyl group” as used herein may refer to a phenyl group substituted with a phenyl group. For example, the “biphenyl group” may be “a substituted phenyl group” having a “C₆-C₆₀aryl group” as a substituent.

The term “terphenyl group” as used herein may refer to a phenyl group substituted with biphenyl group. For example, the “terphenyl group” may be “a substituted phenyl group” having a “C₆-C₆₀aryl group substituted with a C₆-C₆₀aryl group” as a substituent.

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

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

Synthesis Examples

Compounds 1 to 6 used in the Synthesis Examples are as follows:

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Synthesis Example 1: Synthesis of Intermediate (IM-1-1)

11.5 grams (g) of 2,6-dibromoaniline (Compound 1) (45.7 millimole (mmol)), 1.1 g of Pd(PPh₃)₄(0.9 mmol), K₂CO₃(137.1 mmol), and 8.7 g of [1,2]azaborinino[1,2-a][1,2]azaborinin-1-ylboronic acid (50.3 mmol) were added to a reaction vessel, and suspended in 300 milliliters (mL) of toluene and 100 mL of H₂O, followed by heating at a temperature of 100° C. for 6 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 11.9 g (34.3 mmol) of Intermediate IM-1-1 (yield: 75%).

Synthesis Example 2: Synthesis of Intermediate (IM-1-2)

13.5 g of Intermediate IM-1-2 (33.4 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-1-1, except that 2,6-dibromo-4-(tert-butyl)aniline (Compound 2) was used instead of 2,6-dibromoaniline (Compound 1) (yield: 73%).

Synthesis Example 3: Synthesis of Intermediate (IM-2-1)

11.9 g of Intermediate IM-1-1 (34.3 mmol), 9.4 g of 1-iodo-2-nitrobenzene (37.7 mmol), 0.6 g of Pd₂(dba)₃(0.69 mmol), 0.6 g of SPhos (1.37 mmol), and 5.3 g of NaO^tertBu (54.9 mmol) were added to a reaction vessel and suspended in 343 mL of toluene, followed by heating at a temperature of 120° C. for 4 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 12.5 g (26.8 mmol) of Intermediate IM-2-1 (yield: 78%).

Synthesis Example 4: Synthesis of Intermediate (IM-2-2)

13.1 g of Intermediate IM-2-2 (25.0 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-2-1, except that Intermediate IM-1-2 was used instead of Intermediate IM-1-1 (yield: 73%).

Synthesis Example 5: Synthesis of Intermediate (IM-3-1)

12.5 g of Intermediate IM-2-1 (26.8 mmol) and 3.2 g of Sn (26.8 mmol) were added to a reaction vessel and suspended in 268 mL of ethanol, followed by adding 3.2 mL of HCl (37%) dropwise thereto and heating at 80° C. for 10 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 9.4 g (21.4 mmol) of Intermediate IM-3-1 (yield: 80%).

Synthesis Example 6: Synthesis of Intermediate (IM-3-2)

10.3 g of Intermediate IM-3-2 (20.9 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-3-1, except that Intermediate IM-2-2 was used instead of Intermediate IM-2-1 (yield: 78%).

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Synthesis Example 7: Synthesis of Intermediate (IM-4-1)

5.0 g of Intermediate IM-3-1 (11.4 mmol), 6.1 g of 2-(3-bromo-5-(tert-butyl)phenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d₄(Compound 3) (11.4 mmol), 0.2 g of Pd₂(dba)₃(0.2 mmol), 1.9 g of SPhos (4.6 mmol), and 1.7 g of NaO^tertBu (18.2 mmol) were added to a reaction vessel and suspended in 114 mL of toluene, followed by heating at a temperature of 120° C. for 4 hours. Once the reaction was complete, the temperature was lowered to room temperature, and 300 mL of distilled water was added thereto. Then, an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed with saturated NaCl aqueous solution, followed by drying using sodium sulfate. The resulting product was subjected to column chromatography to thereby obtain 7.6 g (8.6 mmol) of Intermediate IM-4-1 (yield: 75%).

Synthesis Example 8: Synthesis of Intermediate (IM-4-2)

7.8 g of Intermediate IM-4-2 (8.3 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-4-1, except that Intermediate IM-3-2 was used instead of Intermediate IM-3-1 (yield: 73%).

Synthesis Example 9: Synthesis of Intermediate (IM-4-3)

13.5 g of Intermediate IM-4-3 (15.2 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-4-2, except that 2-(3-bromophenoxy)-9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazole-5,6,7,8-d₄(Compound 4), instead of Compound 3, was reacted with Intermediate IM-3-2 (yield: 75%).

Synthesis Example 10: Synthesis of Intermediate (IM-4-4)

8.2 g of Intermediate IM-4-4 (8.4 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-4-3, except that 2-((5-bromo-[1,1′-biphenyl]-3-yl-2′,3′,4′,5′,6′-d₅)oxy)-9-(4-(tert-butyl)py-ridin-2-yl)-9H-carbazole-5,6,7,8-d₄(Compound 5), instead of Compound 4, was reacted with Intermediate IM-3-2 (yield: 74%).

Synthesis Example 11: Synthesis of Intermediate (IM-4-5)

8.4 g of Intermediate IM-4-5 (7.8 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-4-4, except that 2-((5-bromo-2′,4′,6′-tri-tert-butyl-[1,1′-biphenyl]-3-yl)oxy)-9-(4-(tert-butyl)-pyridin-2-yl)-9H-carbazole-5,6,7,8-d₄(Compound 6), instead of Compound 5, was reacted with Intermediate IM-3-1, instead of Intermediate IM-3-2 (yield: 68%).

Synthesis Example 12: Synthesis of Intermediate (IM-4-6)

8.4 g of Intermediate IM-4-6 (7.4 mmol) was synthesized in substantially the same manner as in Synthesis of Intermediate IM-4-5, except that 2-((5-bromo-2′,4′,6′-tri-tert-butyl-[1,1′-biphenyl]-3-yl)oxy)-9-(4-(tert-butyl)-pyridin-2-yl)-9H-carbazole-5,6,7,8-d₄(Compound 6) was reacted with Intermediate IM-3-2 instead of Intermediate IM-3-1 (yield: 65%).

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Synthesis Example 13: Synthesis of Intermediate (IM-5-1)

7.6 g of Intermediate IM-4-1 (8.6 mmol), 86 mL of triethyl orthoformate (516 mmol), and 1.0 mL of HCl (37%) (10.3 mmol) were added to a reaction vessel, followed by heating at a temperature of 80° C. for 12 hours. Once the reaction was complete, the temperature was cooled to room temperature, and the resulting solid was filtered and washed using ether. Then, the washed solid was dried to thereby obtain 7.2 g (7.7 mmol) of Intermediate IM-5-1 at a yield of 90%.

Synthesis Example 14: Synthesis of Intermediates IM-5-2 to IM-5-6

7.3 g of Intermediate IM-5-2 (7.4 mmol), 6.9 g of Intermediate IM-5-3 (7.4 mmol), 7.4 g of Intermediate IM-5-4 (7.3 mmol), 8.0 g of Intermediate IM-5-5 (7.1 mmol), and 8.4 g of Intermediate IM-5-6 (7.1 mmol) were respectively synthesized in substantially the same manner as in Synthesis of Intermediate IM-5-1, except that Intermediate IM-4-2, Intermediate IM-4-3, Intermediate IM-4-4, Intermediate IM-4-5, and Intermediate IM-4-6 were respectively used instead of Intermediate IM-4-1, at a yield of 86%, 86%, 85%, 83%, and 82%, respectively.

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Synthesis Example 15: Synthesis of Intermediate (IM-6-1)

7.2 g of Intermediate IM-5-1 (7.7 mmol) and 3.8 g of NH₄PF₆(23.1 mmol) were added to a reaction vessel, followed by suspension in a mixture solution of 100 mL of methanol and 50 mL of water and stirring at room temperature for 24 hours. Once the reaction was complete, the resulting solid was filtered and washed using ether. Then, the washed solid was dried to thereby obtain 7.0 g (6.9 mmol) of Intermediate IM-6-1 at a yield of 90%.

Synthesis Example 16: Synthesis of Intermediates IM-6-2 to IM-6-6

7.6 g of Intermediate IM-6-2 (6.9 mmol), 6.9 g of Intermediate IM-6-3 (6.8 mmol), 8.0 g of Intermediate IM-6-4 (7.1 mmol), 8.5 g of Intermediate IM-6-5 (6.9 mmol), and 8.8 g of Intermediate IM-6-6 (6.8 mmol) were respectively synthesized in substantially the same manner as in Synthesis of Intermediate IM-6-1, except that Intermediate IM-5-2, Intermediate IM-5-3, Intermediate IM-5-4, Intermediate IM-5-5, and Intermediate IM-5-6 were respectively used instead of Intermediate IM-5-1, at a yield of 90%, 88%, 92%, 90%, and 89%, respectively.

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Synthesis Example 17: Synthesis of Compound BD04

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7.0 g of Intermediate IM-6-1 (6.9 mmol), 2.8 g of dichloro(1,5-cyclooctadiene)platinum (7.6 mmol), and 1.7 g of NaOAc (20.7 mmol) were suspended in 150 mL of 1,4-dioxane, followed by heating at a temperature of 110° C. for 72 hours. Once the reaction was complete, the temperature was cooled to room temperature, 150 mL of distilled water was added thereto, and an organic layer was extracted therefrom using ethyl acetate, and the extracted organic layer was washed using NaCl aqueous solution and dried using MgSO₄. The resulting product was subjected to column chromatography to thereby obtain 2.6 g (2.4 mmol) of Compound BD04 (yield: 35%).

Synthesis Example 18: Synthesis of Compound BD19

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2.8 g of Compound BD19 (2.4 mmol) was synthesized in substantially the same manner as in Synthesis of Compound BD04, except that Intermediate IM-6-2 was used instead of Intermediate IM-6-1 (yield: 35%).

Synthesis Example 19: Synthesis of Compound BD17

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2.4 g of Compound BD17 (2.2 mmol) was synthesized in substantially the same manner as in Synthesis of Compound BD04, except that Intermediate IM-6-3 was used instead of Intermediate IM-6-1 (yield: 32%).

Synthesis Example 20: Synthesis of Compound BD22

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2.9 g of Compound BD22 (2.5 mmol) was synthesized in substantially the same manner as in Synthesis of Compound BD04, except that Intermediate IM-6-4 was used instead of Intermediate IM-6-1 (yield: 36%).

Synthesis Example 21: Synthesis of Compound BD10

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2.9 g of Compound BD10 (2.3 mmol) was synthesized in substantially the same manner as in Synthesis of Compound BD04, except that Intermediate IM-6-5 was used instead of Intermediate IM-6-1 (yield: 34%).

Synthesis Example 22: Synthesis of Compound BD25

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3.2 g of Compound BD25 (2.4 mmol) was synthesized in substantially the same manner as in Synthesis of Compound BD04, except that Intermediate IM-6-6 was used instead of Intermediate IM-6-1 (yield: 35%).

Compounds synthesized in Synthesis Examples 17 to 22 were identified by ¹H nuclear magnetic resonance (NMR) and matrix-assisted laser desorption/ionization mass spectrometry time-of-flight mass spectroscopy (MALDI-TOF MS). The results thereof are shown in Table 1.

Methods of synthesizing compounds other than the compounds synthesized in Synthesis Examples 17 to 22 may be easily understood by those skilled in the art by referring to the synthesis pathways and raw materials described above.

TABLE 1

MALDI-TOF MS [M⁺]

Compound

¹H NMR (CDCl₃, 500 MHz)
found
calc.

BD04
δ 9.01 (d, ³J_H-H= 6.3 Hz, 1H), 8.08 (s, 1H), 7.86 (d, ³J_H-H= 8.3
1091.4134
1091.4131

Hz, 1H), 7.64 (d, ³J_H-H= 8.3 Hz, 1H), 7.60-7.40 (m, 3H), 7.32

(d, ³J_H-H= 8.2 Hz, 1H), 7.24-7.22 (m, 3H), 7.15-7.00 (m, 2H),

6.89 (d, ³J_H-H= 8.2 Hz, 1H), 6.86-6.65 (m, 7H), 6.37 (dd,

³J_H-H= 8.1 Hz, 2H), 6.19 (dd, ³J_H-H= 6.3 Hz, ⁴J_H-H= 1.7 Hz,

1H), 6.16 (dd, ³J_H-H= 8.1 Hz, 2H), 5.32 (dd, ³J_H-H= 8.1 Hz,

2H), 1.42 (s, 9H), 1.29 (s, 9H).

BD19
δ 9.03 (d, ³J_H-H= 6.3 Hz, 1H), 8.01 (s, 1H), 7.86 (d, ³J_H-H=
1147.4761
1147.4757

8.3 Hz, 1H), 7.64 (d, ³J_H-H= 8.3 Hz, 1H), 7.60-7.40 (m, 2H),

7.32 (d, ³J_H-H= 8.2 Hz, 1H), 7.24-7.22 (m, 3H), 7.15-7.00

(m, 2H), 6.89 (d, ³J_H-H= 8.2 Hz, 1H), 6.86-6.65 (m, 7H),

6.37 (dd, ³J_H-H= 8.1 Hz, 2H), 6.19 (dd, ³J_H-H= 6.3 Hz, ⁴J_H-H=

1.7 Hz, 1H), 6.16 (dd, ³J_H-H= 8.1 Hz, 2H), 5.32 (dd, ³J_H-H=

8.1 Hz, 2H), 1.42 (s, 9H), 1.31 (s, 9H), 1.29 (s, 9H).

BD17
δ 9.10 (d, ³J_H-H= 6.3 Hz, 1H), 8.12 (s, 1H), 7.88 (d, ³J_H-H=
1091.4136
1091.4131

8.3 Hz, 1H), 7.63 (d, ³J_H-H= 8.3 Hz, 1H), 7.62-7.41 (m, 3H),

7.31 (d, ³J_H-H= 8.2 Hz, 1H), 7.24-7.22 (m, 3H), 7.16-7.01

(m, 2H), 6.87 (d, ³J_H-H= 8.2 Hz, 1H), 6.86-6.65 (m, 7H),

6.36 (dd, ³J_H-H= 8.1 Hz, 2H), 6.18 (dd, ³J_H-H= 6.3 Hz,

⁴J_H-H= 1.7 Hz, 1H), 6.15 (dd, ³J_H-H= 8.1 Hz, 2H), 5.34

(dd, ³J_H-H= 8.1 Hz, 2H), 1.31 (s, 9H), 1.29 (s, 9H).

BD22
δ 9.00 (d, ³J_H-H= 6.3 Hz, 1H), 8.03 (s, 1H), 7.87 (d, ³J_H-H=
1172.4763
1172.4758

8.3 Hz, 1H), 7.65 (d, ³J_H-H= 8.3 Hz, 1H), 7.58-7.38 (m, 2H),

7.30 (d, ³J_H-H= 8.2 Hz, 1H), 7.26-7.23 (m, 3H), 7.16-7.01

(m, 2H), 6.87 (d, ³J_H-H= 8.2 Hz, 1H), 6.87-6.64 (m, 7H),

6.36 (dd, ³J_H-H= 8.1 Hz, 2H), 6.18 (dd, ³J_H-H= 6.3 Hz, ⁴J_H-H=

1.7 Hz, 1H), 6.14 (dd, ³J_H-H= 8.1 Hz, 2H), 5.31 (dd, ³J_H-H=

8.1 Hz, 2H), 1.42 (s, 9H), 1.30 (s, 9H).

BD10
δ 9.01 (d, ³J_H-H= 6.3 Hz, 1H), 8.08 (s, 1H), 7.84 (d, ³J_H-H=
1279.5701
1279.5696

8.3 Hz, 1H), 7.64 (d, ³J_H-H= 8.3 Hz, 1H), 7.60-7.41 (m, 2H),

7.29 (d, ³J_H-H= 8.2 Hz, 1H), 7.28-7.21 (m, 4H), 7.16-7.00

(m, 4H), 6.89 (d, ³J_H-H= 8.2 Hz, 1H), 6.85-6.63 (m, 7H),

6.33 (dd, ³J_H-H= 8.1 Hz, 2H), 6.18 (dd, ³J_H-H= 6.3 Hz, ⁴J_H-H=

1.7 Hz, 1H), 6.12 (dd, ³J_H-H= 8.1 Hz, 2H), 5.26 (dd, ³J_H-H=

8.1 Hz, 2H), 1.35 (s, 18H), 1.31 (s, 9H), 1.30 (s, 9H).

BD25
δ 9.12 (d, ³J_H-H= 6.3 Hz, 1H), 8.02 (s, 1H), 7.86 (d, ³J_H-H=
1335.6325
1335.6322

8.3 Hz, 1H), 7.64 (d, ³J_H-H= 8.3 Hz, 1H), 7.60-7.41 (m, 2H),

7.29 (d, ³J_H-H= 8.2 Hz, 1H), 7.27-7.22 (m, 3H), 7.16-7.00

(m, 4H), 6.88 (d, ³J_H-H= 8.2 Hz, 1H), 6.86-6.64 (m, 7H),

6.32 (dd, ³J_H-H= 8.1 Hz, 2H), 6.17 (dd, ³J_H-H= 6.3 Hz,

⁴J_H-H=1.7 Hz, 1H), 6.11 (dd, ³J_H-H= 8.1 Hz, 2H), 5.28 (dd,

³J_H-H= 8.1 Hz, 2H), 1.42 (s, 9H), 1.35 (s, 18H), 1.31 (s,

9H), 1.30 (s, 9H).

EXAMPLES
Example 1

A Corning 15 Ohms per square centimeter (Ω/cm²) (1,200 Å) ITO glass substrate was cut to a size of 50 millimeters (mm)×50 mm×0.7 mm, sonicated in isopropyl alcohol and pure water for 5 minutes in each solvent, and cleaned by exposure to ultraviolet rays with ozone to use the glass substrate as an anode. Then, the glass substrate was mounted onto a vacuum-deposition apparatus. 2-TNATA was vacuum-deposited on the glass substrate to form a hole injection layer having a thickness of 600 Å. Then, 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB) was vacuum-deposited on the hole injection layer to form a hole transport layer having a thickness of about 300 Å. Compound ETH1 and Compound HTH15 were mixed at a weight ratio of 3:7 as a mixture host to be deposited on the hole transport layer, Compound BD04 was used as a dopant (dopant 13 wt %), and ETH1, HTH15, and BD04 were co-deposited to form an emission layer to a thickness of 400 Å. Subsequently, HBL-1 was vacuum-deposited to a thickness of 50 Å to form a hole blocking layer. Alq₃was deposited on the hole blocking layer as an electron transport layer to a thickness of 300 Å, LiF was deposited on the electron transport layer to a thickness of 10 Å as an electron injection layer, Al was vacuum-deposited to a thickness of 3,000 Å to form a LiF/Al cathode, thereby completing the manufacture of a light-emitting device.

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Example 2

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that ETH2 and HTH15 were used as a mixture host at a weight ratio of 3:7 to form an emission layer.

Example 3

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that ETH2 and HTH15 were used as a mixture host at a weight ratio of 3:7 to form an emission layer, and BD19 was used instead of BD04.

Example 4

Example 5

Example 6

Example 7

Example 8

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that ETH2 and HTH15 were mixed as a mixture host at a weight ratio of 3:7 to form an emission layer, and BD17 (13 wt %) and a delayed fluorescence dopant DFD7 (0.4 wt %), instead of BD04, were co-deposited to form an emission layer having a thickness of 400 Å.

Comparative Example 1

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound BD-CE1 was used instead of Compound BD04 to form an emission layer.

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Comparative Example 2

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound BD-CE2 was used instead of Compound BD04 to form an emission layer.

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Comparative Example 3

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound BD-CE3 was used instead of Compound BD04 to form an emission layer.

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Comparative Example 4

A light-emitting device was manufactured in substantially the same manner as in Example 1, except that Compound BD-CE4 was used instead of Compound BD04 to form an emission layer.

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The driving voltage, color coordinates, luminescence efficiency, color-conversion efficiency (luminescence efficiency/CIE_y), maximum emission wavelength (nm), and lifespan (T95) at luminance of 1,000 cd/m²of the light-emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 to 4 were measured by using Keithley source-measure unit (SMU) 236 and a luminance meter PR650. The results thereof are shown in Table 2. In Table 2, the lifespan (T95) indicates a time (in hours) that it took for the luminance of each light-emitting device to decline to 95% of its initial luminance under the same condition.

TABLE 2

Color-
Maximum

Driving

Luminescence
conversion
emission
Lifespan

Luminance
voltage

efficiency
efficiency
wavelength
(T95,

(cd/m²)
(V)
CIE_(x,y)
(cd/A)
(cd/A/y)
(nm)
hour)

Example 1
1,000
4.9
(0.134,
22.1
122.3
462
121.0

0.181)

Example 2
1,000
4.9
(0.134,
22.1
122.3
462
140.0

0.181)

Example 3
1,000
4.8
(0.135,
22.5
127.1
463
156.0

0.177)

Example 4
1,000
4.6
(0.135,
23.3
127.8
463
170.2

0.183)

Example 5
1,000
4.6
(0.135,
21.4
137.1
461
133.0

0.56)

Example 6
1,000
4.7
(0.134,
23.6
138.1
461
135.0

0.171)

Example 7
1,000
4.7
(0.134,
23.6
138.1
461
148.3

0.171)

Example 8
1,000
4.3
(0.135,
20.7
152.9
461
200.4

0.135)

Comparative
1,000
4.7
(0.134,
22.9
118.5
462
45.0

Example 1

0.193)

Comparative
1,000
4.3
(0.199,
26.8
92.4
463
4.0

Example 2

0.290)

Comparative
1,000
4.7
(0.136,
24.6
120.6
464
35.0

Example 3

0.205)

Comparative
1,000
4.7
(0.134,
23.3
115.6
462
28.0

Example 4

0.194)

As shown in Table 2, the light-emitting devices of Examples 1 to 8 were each found to exhibit excellent color-conversion efficiency and long lifespan in a blue emission area, as compared with the light-emitting devices of Comparative Examples 1 to 4.

When the compound according to one or more embodiments is used in a light-emitting device, the device may have excellent (desired) driving voltage, efficiency, colorimetric purity, and/or lifespan.

As apparent from the foregoing description, a light-emitting device including the organometallic compound may have a low driving voltage, high efficiency, high colorimetric purity, and long lifespan.

It should be understood that embodiments described herein should be considered in a descriptive sense only and not for purposes of limitation. Descriptions of features or aspects within each embodiment should typically be considered as available for other similar features or aspects in other embodiments. While one or more embodiments have been described with reference to the figures, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope of the present disclosure as defined by the following claims and their equivalents.

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

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