ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND DIAGNOSTIC COMPOSITION INCLUDING THE ORGANOMETALLIC COMPOUND

BACKGROUND
1. Field

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

2. Description of the Related Art

Organic light-emitting devices (OLEDs) are self-emission devices, which have better characteristics including wide viewing angles, high contrast ratios, short response times, and excellent brightness, driving voltage, and response speed, and produce full-color images.

In an example, an organic light-emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be disposed between the anode and the emission layer, and an electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. The holes and the electrons recombine in the emission layer to produce excitons. These excitons transit from an excited state to a ground state, thereby generating light.

Meanwhile, luminescent compounds may be used to monitor, sense, or detect a variety of biological materials including cells and proteins. An example of the luminescent compounds includes a phosphorescent luminescent compound.

Various types of organic light emitting devices are known. However, there still remains a need in OLEDs having low driving voltage, high efficiency, high brightness, and long lifespan.

SUMMARY

One or more embodiments include a novel organometallic compound, an organic light-emitting device including the organometallic compound, and a diagnostic composition including the organometallic compound.

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

According to one or more embodiments, an organometallic compound is represented by Formula 1A:

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In Formula 1A,

M may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au),

X₁may be O or S, a bond between X₁and M may be a covalent bond,

X₂and X₃may each independently be C or N,

X₄may be N,

one bond selected from a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a covalent bond, and the others thereof may each be a coordinate bond,

Y₁and Y₃to Y₅may each independently be C or N,

a bond between X₂and Y₃, a bond between X₂and Y₄, a bond between Y₄and Y₅, a bond between Y₅and X₅₁, a bond between X₅₁and Y₃may each be a chemical bond,

CY₁to CY₅may each independently be selected from a C₅-C₃₀carbocyclic group and a C₁-C₃₀heterocyclic group, wherein CY₄is not a benzimidazole group,

a cyclometallated ring formed by CY₅, CY₂, CY₃, and M may be a 6-membered ring,

X₅₁may be selected from O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), C(═O), N, C(R₇), Si(R₇), and Ge(R₇),

R₇and R₈may be optionally linked via a first linking group to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

L₁to L₄and L₇may each independently be selected from a substituted or unsubstituted C₅-C₃₀carbocyclic group and a substituted or unsubstituted C₁-C₃₀heterocyclic group,

b1 to b4 and b7 may each independently be an integer from 0 to 5,

R₁to R₄, R₇, and R₈may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₁₀alkyl group, a substituted or unsubstituted C₂-C₁₀alkenyl group, a substituted or unsubstituted C₂-C₁₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₇-C₆₀arylalkyl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀heteroaryloxy group, a substituted or unsubstituted C₂-C₆₀heteroarylthio group, a substituted or unsubstituted C₃-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉),

c1 to c4 may each independently be an integer from 1 to 5,

a1 to a4 may each independently be 0, 1, 2, 3, 4, or 5,

two of a plurality of neighboring groups R₁may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of a plurality of neighboring groups R₂may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of a plurality of neighboring groups R₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of a plurality of neighboring groups R₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two or more neighboring groups selected from R₁to R₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

a1 to a4 may each independently be 1, 2, 3, 4, or 5, and at least one selected from R₁to R₄may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C1-C10 heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C1-C10 heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₁₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, in the cases where i) M is Pt, ii) X₁is O, iii) X₂and X₄are each N, X₃is C, a bond between X₂and M and a bond between X₄and M are each a coordinate bond, and a bond between X₃and M is a covalent bond, iv) Y₁to Y₅are each C, v) a bond between Y₅and X₅₁and a bond between Y₃and X₅₁are each a single bond, vi) CY₁, CY₂, and CY₃are each a benzene group, and CY₄is a pyridine group, vii) X₅₁is O, S, or N-[(L₇)_b7-(R₇)_c7], and viii) b7 is 0, c7 is 1, and R₇is a substituted or unsubstituted C₁-C₁₀alkyl group,

at least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₁-C₃₀heterocyclic group, the substituted C₁-C₁₀alkyl group, the substituted C₂-C₁₀alkenyl group, the substituted C₂-C₁₀alkynyl group, the substituted C₁-C₁₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C1-C10 heterocycloalkyl group, the substituted C3-C10 cycloalkenyl group, the substituted C1-C10 heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₇-C₁₀arylalkyl group, the substituted C₁-C₁₀heteroaryl group, the substituted C₂-C₁₀heteroaryloxy group, the substituted C₂-C₁₀heteroarylthio group, the substituted C₃-C₁₀heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₁₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —S(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₁₀arylalkyl group, a C₁-C₁₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₁₀heteroarylthio group, a C₃-C₁₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉), and

Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, and Q₃₁to Q₃₉may each independently be selected from hydrogen, deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₁-C₆₀alkyl group substituted with at least one selected from deuterium, a C₁-C₆₀alkyl group, and a C₆-C₆₀aryl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryl group substituted with at least one selected from deuterium, a C₁-C₆₀alkyl group, and a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

According to one or more embodiments, an organic light-emitting device includes:

a first electrode;

a second electrode; and

an organic layer disposed between the first electrode and the second electrode,

wherein the organic layer includes an emission layer and at least one organometallic compound.

The organometallic compound may act as a dopant in the organic layer.

According to one or more embodiments, a diagnostic composition includes at least one of the organometallic compound represented by Formula 1A.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the FIGURE which is a schematic view of an organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

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

It will be understood that when an element is referred to as being “on” another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements present.

It will be understood that, although the terms first, second, third etc. may be used herein to describe various elements, components, regions, layers, and/or sections, these elements, components, regions, layers, and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer, or section from another element, component, region, layer, or section. Thus, a first element, component, region, layer, or section discussed below could be termed a second element, component, region, layer, or section without departing from the teachings of the present embodiments.

The terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting. 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.

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

Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the relevant art and the present disclosure, and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.

Exemplary embodiments are described herein with reference to cross section illustrations that are schematic illustrations of idealized embodiments. As such, variations from the shapes of the illustrations as a result, for example, of manufacturing techniques and/or tolerances, are to be expected. Thus, embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, a region illustrated or described as flat may, typically, have rough and/or nonlinear features. Moreover, sharp angles that are illustrated may be rounded. Thus, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the present claims.

“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” can mean within one or more standard deviations, or within ±30%, 20%, 10%, 5% of the stated value.

In an embodiment, an organometallic compound is provided.

An organometallic compound according to an embodiment may be represented by Formula 1A:

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In Formula 1A, M may be beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).

For example, M in Formula 1A may be platinum (Pt), but embodiments of the present disclosure are not limited thereto.

The organometallic compound represented by Formula 1A may be a neutral compound which does not consist of an ion pair of an anion and a cation.

In Formula 1A, X₁may be O or S, and a bond between X₁and M may be a covalent bond.

For example, in Formula 1A, X₁may be O, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, X₂and X₃may each independently be C or N, and X₄may be N.

In an embodiment, in Formula 1A, X₃may be C, and X₂and X₄may each be N.

In Formula 1A, one bond selected from a bond between X₂and M, a bond between X₃and M, and a bond between X₄and M may be a covalent bond, and the others thereof may each be a coordinate bond.

In an embodiment, a bond between X₂and M and a bond between X₄and M may each be a coordinate bond, and a bond between X₃and M may be a covalent bond.

For example, in Formula 1A,

i) X₂and X₄may each be N, X₃may be C, a bond between X₂and M and a bond between X₄and M may each be a coordinate bond, and a bond between X₃and M may be a covalent bond; or

ii) X₃and X₄may each be N, X₂may be C, a bond between X₃and M and a bond between X₄and M may each be a coordinate bond, and a bond between X₂and M may be a covalent bond.

In Formula 1A, Y₁and Y₃to Y₅may each independently be C or N.

For example, in Formula 1A, Y₁and Y₃may each be C, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, a bond between X₂and Y₃, a bond between X₂and Y₄, bond between Y₄and Y₅, a bond between Y₅and X₅₁, and a bond between X₅₁and Y₃may each be a chemical bond (for example, a single bond, a double bond, a covalent bond or the like).

In Formula 1A, CY₁to CY₅may each independently be selected from a C₅-C₃₀carbocyclic group and a C₁-C₃₀heterocyclic group. Here, CY₄is not a benzimidazole group.

For example, in Formula 1A, CY₁to CY₄may each independently be selected from a) a 6-membered ring, b) a condensed ring having two or more 6-membered rings that are condensed to each other, and c) a condensed ring having two or more 6-membered rings and one 5-membered ring that are condensed to each other, wherein the 6-membered ring may be selected from a cyclohexane group, a cyclohexene group, an adamantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, and the 5-membered ring may be selected from a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a silole group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, and a thiadiazole group.

In an embodiment, CY₁to CY₄may each independently be selected from 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 furan group, a thiophene group, silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, azadibenzosilole 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, phenanthroline group, a cinnoline group, a phthalazine group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole 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 benzooxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a 5,6,7,8-tetrahydrophthalazine group, and a 5,6,7,8-tetrahydrocinnoline group.

In one or more embodiments, CY₁to CY₄may each independently be selected from 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 fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, an azadibenzosilole 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 cinnoline group, a phthalazine group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a 5,6,7,8-tetrahydrophthalazine group, and a 5,6,7,8-tetrahydrocinnoline group, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, CY₅may be a 5-membered ring.

In Formula 1A, a cyclometallated ring formed by CY₅, CY₂, CY₃, and M may be a 6-membered ring.

In Formula 1A, X₅₁may be selected from O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), C(═O), N, C(R₇), Si(R₇), and Ge(R₇), R₇and R₈may be optionally linked via a first linking group to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group (for example, a C₅-C₆5-membered to 7-membered cyclic group, or a C₅-C₆5-membered to 7-membered cyclic group substituted with at least one of deuterium, a cyano group, —F, a C₁-C₁₀alkyl group, and a C₆-C₁₄aryl group). Here, L₇, b7, R₇, c7, and R₈are each independently the same as described below.

The first linking group may be selected from a single bond, *—O—*′, *—S—*′, *—C(R₅)(R₆)—*′, *—C(R₅)=*′, *═C(R₆)—*′, *—C(R₅)═C(R₆)—*′, *—C(═O)—*′, *—C(═S)—*′, *—C≡C—*′, *—N(R₅)—*′, *—Si(R₅)(R₆)—*′, and *—P(R₅)(R₆)—*′, R₅and R₆are each independently the same as described in connection with R₁, and * and *′ each indicate a binding site to a neighboring atom.

In Formula 1A, L₁to L₄and L₇may each independently be selected from a substituted or unsubstituted C₅-C₃₀carbocyclic group and a substituted or unsubstituted C₁-C₃₀heterocyclic group.

For example, in Formula 1A, L₁to L₄and L₇may each independently be selected from:

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 furan group, a thiophene group, silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, azadibenzosilole 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, phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole 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 benzooxadiazole group, and a benzothiadiazole group; and 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 furan group, a thiophene group, silole group, an indene group, a fluorene group, an indole group, a carbazole group, a benzofuran group, a dibenzofuran group, a benzothiophene group, a dibenzothiophene group, a benzosilole group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, azadibenzosilole 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, phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an iso-oxazole 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 benzooxadiazole group, and a benzothiadiazole group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a triazinyl group, a fluorenyl group, a dimethylfluorenyl group, a diphenylfluorenyl group, a carbazolyl group, a phenylcarbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a dimethyldibenzosilolyl group, a diphenyldibenzosilolyl group, —N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉),

Q₃₁to Q₃₉may each independently be selected from:

—CH₃, —CD₃, —CD₂H, —CDH₂, —CH₂CH₃, —CH₂CD₃, —CH₂CD₂H, —CH₂CDH₂, —CHDCH₃, —CHDCD₂H, —CHDCDH₂, —CHDCD₃, —CD₂CD₃, —CD₂CD₂H, and —CD₂CDH₂;

an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each substituted with at least one selected from deuterium, a C₁-C₁₀alkyl group, and a phenyl group, but embodiments of the present disclosure are not limited thereto.

In an embodiment, in Formula 1A, L₁to L₄and L₇may each independently be selected from:

a benzene group, a pyridine group, and a pyrimidine group; and

a benzene group, a pyridine group, and a pyrimidine group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a pyridinyl group, and a pyrimidinyl group, —N(Q₃₁)(Q₃₂), —S(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉) (wherein Q₃₁to Q₃₉are each independently the same as described herein),

but embodiments of the present disclosure are not limited thereto.

In Formula 1A, b1 to b4 and b7 respectively indicate the number of L₁to L₄and L₇, and may each independently be an integer from 0 to 5. When b1 is 0, *-(L₁)_b1-*′ may be a single bond. When b1 is two or more, two or more groups L₁may be identical to or different from each other. b2 to b4 and b7 are each independently the same as described in connection with b1.

In an embodiment, in Formula 1A, b1 to b4 and b7 may be each independently 0 or 1, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, R₁to R₄, R₇, and R₈may each independently be selected from hydrogen, deuterium, —F, —C, —Br, —I, —SF₅, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₇-C₆₀arylalkyl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₆₀heteroaryloxy group, a substituted or unsubstituted C₂-C₆₀heteroarylthio group, a substituted or unsubstituted C₃-C₆₀heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉).

For example, R₁to R₄, R₇, and R₈may each independently be selected from:

hydrogen, deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, —SF₅, a C₁-C₂₀alkyl group, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl (adamantyl) group, a norbornanyl (norbornyl) group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group;

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group and —Si(Q₃₃)(Q₃₄)(Q₃₅); and

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉), and

Q₁to Q₉and Q₃₃to Q_3aare each independently the same as described in connection with Q₃₁.

In an embodiment, R₁to R₄, R₇, and R₈may each independently be selected from:

hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, 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, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, 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, a tert-decyl group, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and a dibenzosilolyl group, each substituted with at least one selected from deuterium, —F, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a cyano group, a nitro group, a C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group and —Si(Q₃₃)(Q₃₄)(Q₃₅); and

—N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉), and

Q₁to Q₉and Q₃₃to Q₃₅are each independently the same as described herein, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R₁to R₄, R₇, and R₈may each independently be selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, —C₂F₅, —C₂F₄H, —C₂F₃H₂, —C₂F₂H₃, —C₂FH₄, groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-167, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉) (wherein Q₁to Q₉are each independently the same as described herein), but embodiments of the present disclosure are not limited thereto:

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In groups represented by Formulae 9-1 to 9-19 and Formulae 10-1 to 10-167, * indicate a binding site to a neighboring group, “Ph” indicates a phenyl group, and “TMS” indicates a trimethylsilyl group.

In Formula 1A, c1 to c4 respectively indicate the number of R₁to R₄, and may each independently be an integer from 1 to 5. When c1 is two or more, two or more groups R₁may be identical to or different from each other. c2 to c4 are each independently the same as described in connection with c1.

In an embodiment, in Formula 1A, c1 to c4 may each independently be 1 or 2, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, a1 to a4 respectively indicate the number of *-[(L₁)_b1-(R₁)_c1], *-[(L₂)_b2-(R₂)_c2], *-[(L₃)_b3-(R₃)_c3], and *-[(L₄)_b4-(R₄)_c4], and may each independently be 0, 1, 2, 3, 4, or 5. When a1 is two or more, two or more groups *-[(L₁)_b1-(R₁)_c1] may be identical to or different from each other. When a2 is two or more, two or more groups *-[(L₂)_b2—(R₂)_c2] may be identical to or different from each other. When a3 is two or more, two or more groups *-[(L₃)_b3-(R₃)_c3] may be identical to or different from each other. When a4 is two or more, two or more groups *-[(L₄)_b4-(R₄)_c4] may be identical to or different from each other. However, embodiments of the present disclosure are not limited thereto.

For example, in Formula 1A, a1 to a4 may each independently be 1, 2, 3, 4, or 5, and

i) at least one selected from R₁to R₄may not be hydrogen,

ii) at least one selected from R₁, R₂, and R₄may not be hydrogen,

iii) at least one selected from R₁to R₃may not be hydrogen, or

iv) at least one selected from R₁and R₂may not be hydrogen, but embodiments of the present disclosure are not limited thereto.

In Formula 1A, i) two of a plurality of neighboring groups R₁may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, ii) two of a plurality of neighboring groups R₂may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, iii) two of a plurality of neighboring groups R₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, iv) two of a plurality of neighboring groups R₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, and v) two or more neighboring groups selected from R₁to R₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

For example, in Formula 1A, i) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₁, ii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₂, iii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₃, iv) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of a plurality of neighboring groups R₄, and v) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two or more neighboring groups selected from R₁to R₄may each independently be selected from:

a cyclopentadiene group, a cyclohexane group, a cycloheptane group, an adamantane group, a norbornane group, a norbornene group, a bicycle-heptane group, a bicyclo-octane group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a naphthalene group, an anthracene group, a tetracene group, a phenanthrene group, a dihydronaphthalene group, a phenalene group, a benzothiophene group, a benzofuran group, an indene group, an indole group, a benzosilole group, an azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, and an azabenzosilole group; and

R_1amay be the same as described in connection with R₁.

“An azabenzothiophene group, an azabenzofuran group, an azaindene group, an azaindole group, an azabenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, an azafluorene group, an azacarbazole group, and an azadibenzosilole group” as used herein mean hetero-rings that respectively have the same backbones as “a benzothiophene group, a benzofuran group, an indene group, an indole group, a benzosilole group, a dibenzothiophene group, a dibenzofuran group, a fluorene group, a carbazole group, and a dibenzosilole group', wherein at least one of carbons forming rings thereof is substituted with nitrogen.

In an embodiment, in Formula 1A,

i) a bond between Y₃and X₅₁and a bond between Y₅and X₅₁may each be a single bond, and X₅₁may be C(R₇)(R₈), Si(R₇)(R₈), or C(═O),

ii) a bond between Y₃and X₅₁and a bond between Y₅and X₅₁may each be a single bond, X₅₁may be N-[(L₇)_b7-(R₇)_c7], and R₇may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₅-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₇-C₆₀arylalkyl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted C₂-C₁₀heteroaryloxy group, a substituted or unsubstituted C₂-C₁₀heteroarylthio group, a substituted or unsubstituted C₃-C₁₀heteroarylalkyl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, or

iii) one bond selected from a bond between Y₃and X₅₁and a bond between Y₅and X₅₁may be a single bond, and the others thereof may each be a double bond, and X₅₁may be N, C(R₇), or Si(R₇).

In one or more embodiments, in Formula 1A, X₅₁may be N-[(L₇)_b7-(R₇)_c7], and R₇may be selected from:

a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a fluorenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a pyrrolyl group, a thiophenyl group, a furanyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolyl group, an isoxazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, an isoindolyl group, an indolyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzosilolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅), and

Q₃₃to Q₃₅are each independently the same as described herein.

In one or more embodiments, in Formula 1A, X₅₁may be N-[(L₇)_b7-(R₇)_c7], and R₇may be selected from groups represented by Formulae 10-1 to 10-128 and groups represented by Formulae 10-131 to 10-167, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 1A,

in cases where i) M is Pt, ii) X₁is O, iii) X₂and X₄are each N, X₃is C, a bond between X₂and M and a bond between X₄and M are each a coordinate bond, and a bond between X₃and M is a covalent bond, iv) Y₁to Y₅are each C, v) a bond between Y₅and X₅₁and a bond between Y₃and X₅₁are each a single bond, vi) CY₁, CY₂, and CY₃are each a benzene group, and CY₄is a pyridine group, vii) X₅₁is O, S, or N-[(L₇)_b7-(R₇)_c7], and viii) b7 is 0, c7 is 1, and R₇is a substituted or unsubstituted C₁-C₆₀alkyl group,

In one or more embodiments, Formula 1A, in which X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7], b7 may be 0, c7 may be 1, and R₇may be a substituted or unsubstituted C₁-C₆₀alkyl group may be satisfied with at least one selected from “Condition 1” to “Condition 6”:

Condition 1

Condition 2

X₁may be S

Condition 3

X₃and X₄may each be N, X₂may be C, a bond between X₃and M and a bond between X₄and M may each be a coordinate bond, and a bond between X₂and M may be a covalent bond;

Condition 4

at least one selected from Y₁to Y₅may not be C;

Condition 5

at least one selected from CY₁, CY₂, and CY₃may not be a benzene group; and

Condition 6

CY₄may not be a pyridine group

In one or more embodiments, the organometallic compound may be represented by Formula 1A, wherein

M may be Pt,

X₁may be O,

X₂and X₄may each be N, X₃may be C, a bond between X₂and M and a bond between X₄and M may each be a coordinate bond, a bond between X₃and M may be a covalent bond,

Y₁to Y₅may each be C,

a bond between Y₅and X₅₁, a bond between Y₃and X₅₁may each be a single bond,

CY₁, CY₂, and CY₃may each be a benzene group, CY₄may be a pyridine group,

X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7],

b7 may be 0, c7 may be 1, R₇may be a substituted or unsubstituted C₁-C₆₀alkyl group,

a1 to a4 may each independently be 1, 2, 3, or 4, and

at least one selected from R₁to R₄may each independently be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments, the organometallic compound may be represented by Formula 1A, wherein

M may be Pt,

X₁may be O,

X₂and X₄may each be N, X₃may be C, a bond between X₂and M and a bond between X₄and M may each be a coordinate bond, a bond between X₃and M may be a covalent bond,

Y₁to Y₅may each be C,

a bond between Y₅and X₅₁, a bond between Y₃and X₅₁may each be a single bond,

CY₁, CY₂, and CY₃may each be a benzene group, CY₄may be a pyridine group,

X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7],

b7 may be 0, c7 may be 1,

R₇may be selected from:

a C₁-C₃₀alkyl group; and

a C₁-C₃₀alkyl group substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, C₁-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group,

a1 to a4 may each independently be 1, 2, 3, or 4, and

at least one selected from R₁to R₄may each independently be selected from:

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 1A,

X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7], b7 may be 0, c7 may be 1,

R₇may be selected from:

a C₁-C₃₀alkyl group, and

a1 to a4 may each independently be 1, 2, 3, or 4, and

at least one selected from R₁to R₄may each independently be selected from:

In an embodiment, in Formula 1A, a moiety represented by

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may be represented by one selected from Formulae CY1-1 to CY1-16:

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In Formulae CY1-1 to CY1-16,

Y₁may be the same as described herein,

X₁₁may be N or C-[(L₁₁)_b11-(R₁₁)_c11], X₁₂may be N or C-[(L₁₂)_b12-(R₁₂)_c12], X₁₃may be N or C-[(L₁₃)_b13-(R₁₃)_c13], X₁₄may be N or C-[(L₁₄)_b14-(R₁₄)_c14], X₁₅may be N or C-[(L₁₅)_b15-(R₁₅)_c15], X₁₆may be N or C-[(L₁₆)_b16-(R₁₆)_c16], X₁₇may be N or C-[(L₁₇)_b17-(R₁₇)_c17], X₁₈may be N or C-[(L₁₈)_b18-(R₁)_c18],

X₁₉may be C(R₁₉)(R_19b), N-[(L₁₉)_b19-(R₁₉)_c19], O, S, or Si(R₁₉)(R_19b),

L₁₁to L₁₉may each independently be the same as described in connection with L₁,

b11 to b19 may each independently be the same as described in connection with b1,

R₁₁to R₁₉and R_1ato R_1cmay each independently be the same as described in connection with R₁,

c11 to c19 may each independently be the same as described in connection with c1,

*′ indicates a binding site to M of Formula 1A, and

* indicates a binding site to CY5 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

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may be represented by one selected from Formulae A1(1) to A1(30):

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In Formulae A1(1) to A1(30),

Y₁, L₁, b1, R₁, and c1 may each independently be the same as described herein,

X₁₉may be C(R_19a)(R_19b), N-[(L₁₉)_b19-(R₁₉)_c19], O, S, or Si(R_19a)(R_19b),

L₁₉, b19, and c19 may each independently be the same as described in connection with L₁, b1, and c1,

R₁₅to R₁₉and R_1ato R_1cmay each independently be the same as described in connection with R₁,

a16 may be an integer from 0 to 6,

a15 may be an integer from 0 to 5,

a14 may be an integer from 0 to 4,

a13 may be an integer from 0 to 3,

a12 may be an integer from 0 to 2,

*′ indicates a binding site to M of Formula 1A, and

* indicates a binding site to CY5 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

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may be represented by one selected from Formulae CY2-1 to CY2-4:

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X₅₁in Formula CY2-1 may be O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), or C(═O), X₅₁in Formulae CY2-2 to CY2-4 may be N, C(R₇), Si(R₇), or Ge(R₇), L₇, b7, R₇, R₈, c7, and c8 may each independently be the same as described herein,

in Formulae CY2-1 to CY2-4,

X₂may be the same as described herein,

X₂₁may be N or C-[(L₂₁)_b21-(R₂₁)_c21], X₂₂may be N or C-[(L₂₂)_b22-(R₂₂)_c22], X₂₃may be N or C-[(L₂₃)_b23-(R₂₃)_c23],

L₂₁to L₂₃may each independently be the same as described in connection with L₂,

b21 to b23 may each independently be the same as described in connection with b2,

R₂₁to R₂₃may each independently be the same as described in connection with R₂,

c21 to c23 may each independently be the same as described in connection with c2,

*′ indicates a binding site to M of Formula 1A,

* indicates a binding site to CY1 of Formula 1A, and

*″ indicates a binding site to CY3 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae A2(1) to A2(16):

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X₅₁in Formulae A2(1) to A2(4) may be O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), or C(═O), X₅₁in Formulae A2(5) to A2(16) may be N, C(R₇), Si(R₇), or Ge(R₇), L₇, b7, R₇, R₈, c7, and c8 may each independently be the same as described herein,

in Formulae A2(1) to A2(16),

X₂, L₂, b2, R₂, and c2 may each independently be the same as described herein,

a23 may be an integer from 0 to 3,

a22 may be an integer from 0 to 2,

*′ indicates a binding site to M of Formula 1A,

* indicates a binding site to CY1 of Formula 1A, and

*″ indicates a binding site to CY3 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae CY3-1 to CY3-11:

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In Formulae CY3-1 to CY3-11, X₃may be the same as described herein,

X₃₁may be N or C-[(L₃₁)_b31-(R₃₁)_c31], X₃₂may be N or C-[(L₃₂)_b32-(R₃₂)_c32], X₃₃may be N or C-[(L₃₃)_b33-(R₃₃)_c33], X₃₄may be N or C-[(L₃₄)_b34-(R₃₄)_c34], X₃₅may be N or C-[(L₃₅)_b35-(R₃₅)_c35], X₃₆may be N or C-[(L₃₆)_b36-(R₃₆)_c36], X₃₇may be N or C-[(L₃₇)_b37-(R₃₇)_c37],

X₃₉may be C(R_39a)(R_39b), N-[(L₃₉)_b39-(R₃₉)_c39], O, S, or Si(R_39a)(R_39b),

L₃₁to L₃₇and L₃₉may each independently be the same as described in connection with L₃,

b31 to b37 and b39 may each independently be the same as described in connection with b3,

R₃₁to R₃₉and R_39ato R_39bmay each independently be the same as described in connection with R₃,

c31 to c37 and c39 may each independently be the same as described in connection with c3,

*′ indicates a binding site to M of Formula 1A,

* indicates a binding site to CY4 of Formula 1A, and

*″ indicates a binding site to CY2 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae A3(1) to A3(17):

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In Formulae A3(1) to A3(17),

X₃, L₃, b3, R₃, and c3 may each independently be the same as described herein,

X₃₉may be C(R_39a)(R_39b), N-[(L₃₉)_b39-(R₃₉)_c39], O, S, or Si(R_39a)(R_39b),

L₃₉, b39, and c39 may each independently be the same as described in connection with L₃, b3, and c3,

R₃₁to R₃₉and R_39ato R_39bmay each independently be the same as described in connection with R₃,

a35 may be an integer from 0 to 5,

a34 may be an integer from 0 to 4,

a33 may be an integer from 0 to 3,

a32 may be an integer from 0 to 2,

*′ indicates a binding site to M of Formula 1A,

* indicates a binding site to CY4 of Formula 1A, and

*″ indicates a binding site to CY2 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae CY4-1 to CY4-16:

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In Formulae CY4-1 to CY4-16,

X₄may be the same as described herein,

X₄₁may be Nor C-[(L₄₁)_b41-(R₄₁)_c41], X₄₂may be Nor C-[(L₄₂)_b42-(R₄₂)_c42], X₄₃may be N or C-[(L₄₃)_b43-(R₄₃)_c43], X₄₄may be Nor C-[(L₄₄)_b44-(R₄₄)_c44], X₄₅may be Nor C-[(L₄₅)_b45-(R₄₅)_c45], X₄₆may be N or C-[(L₄₆)_b46-(R₄₆)_c46], X₄₇may be N or C-[(L₄₇)_b47-(R₄₇)_c47], X₄₈may be N or C-[(L₄₈)_b48-(R₄₈)_c48],

X₄₉may be C(R_49a)(R_49b), N-[(L₄₉)_b49-(R₄₉)_c49], O, S, or Si(R_49a)(R_49b),

L₄₁to L₄₉may each independently be the same as described in connection with L₄,

b41 to b49 may each independently be the same as described in connection with b4,

R₄₁to R₄₉and R_49ato R_49cmay each independently be the same as described in connection with R₄,

c41 to c49 may each independently be the same as described in connection with c4,

*′ indicates a binding site to M of Formula 1A, and

* indicates a binding site to CY3 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae A4(1) to A4(45):

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In Formulae A4(1) to A4(45),

X₄, L₄, b4, R₄, and c4 may each independently be the same as described herein,

X₄₉may be C(R_49a)(R_49b), N-[(L₄₉)_b49-(R₄₉)_c49], O, S, or Si(R_49a)(R_49b),

L₄₉, b49, and c49 may each independently be the same as described in connection L₄, b4, and c4,

R₄₅to R₄₉and R_49ato R_49cmay each independently be the same as described in connection R₄,

a46 may be an integer from 0 to 6,

a45 may be an integer from 0 to 5,

a44 may be an integer from 0 to 4,

a43 may be an integer from 0 to 3,

a42 may be an integer from 0 to 2,

*′ indicates a binding site to M of Formula 1A, and

* indicates a binding site to CY3 of Formula 1A.

In one or more embodiments, in Formula 1A, a moiety represented by

embedded image

may be represented by one selected from Formulae CY1(1) to CY1(8), and/or a moiety represented by

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may be represented by one selected from Formulae CY2(1) to CY2(4), and/or a moiety represented by

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may be represented by one selected from Formulae CY3(1) to CY3(24), and/or a moiety represented by

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may be represented by one selected from Formulae CY4(1) to CY4(67):

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X₅₁in Formulae CY2(1) to CY2(4) may be O, S, N-[(L₇)_b7-(R₇)_c7], C(R₇)(R₈), Si(R₇)(R₈), Ge(R₇)(R₈), or C(═O), L₇, b7, R₇, R₈, c7, and c8 may each independently be the same as described herein,

in Formulae CY1(1) to CY1(8), Formulae CY2(1) to CY2(4), Formulae CY3(1) to CY3(24), and Formulae CY4(1) to CY4(67),

X₂to X₄, Y₁, L₁to L₄, b1 to b4, R₁to R₄, and c1 to c4 may each independently be the same as described herein,

X₃₉may be C(R_39a)(R_39b), N-[(L₃₉)_b39-(R₃₉)_c39], O, S, or Si(R_39a)(R_39b),

X₄₉may be C(R_49a)(R_49b), N-[(L₄₉)_b49-(R₄₉)_c49], O, S, or Si(R_49a)(R_49b),

L_1aand L_1bmay each independently be the same as described in connection with L₁,

R_1aand R_1bmay each independently be the same as described in connection with R₁,

L_3a, L_3b, and L₃₉may each independently be the same as described in connection with L₃,

R_3a, R_3b, R₃₉, R_39a, and R_39bmay each independently be the same as described in connection with R₃,

b39 and c39 may each independently be the same as described in connection with b3 and c3,

L_4a, L_4b, and L₄₉may each independently be the same as described in connection with L₄,

R_4a, R_4b, R₄₉, R_49a, and R_49bmay each independently be the same as described in connection with R₄,

b49 and c49 may each independently be the same as described in connection with b4 and c4,

*-(L₁)_b1-(R₁)_c1, *-(L_1a)_b1-(R_1a)_c1, *-(L_1b)_b1-(R_1b)_c1, *-(L₂)_b2-(R₂)_c2, *-(L₃)_b3-(R₃)_c3, *-(L_3a)_b3-(R_3a)_c3, *-(L_3b)_b3-(R_3b)_c3, *-(L₄)_b4-(R₄)_c4, *-(L_4a)_b4-(R_4a)_c4, and *-(L_4b)_b4-(R_4b)_c4may each not be hydrogen, wherein * indicates a bonding site to a neighboring atom,

in Formulae CY1(1) to CY1(8), Formulae CY2(1) to CY2(4), Formulae CY3(1) to CY3(24), and Formulae CY4(1) to CY4(67), *′ indicates a binding site to M of Formula 1A,

in Formulae CY1(1) to CY1(8), * indicates a binding site to CY5 of Formula 1A,

in Formulae CY2(1) to CY2(4), * indicates a binding site to CY1 of Formula 1A and indicates a binding site to CY3 of Formula 1A,

in Formulae CY3(1) to CY3(24), *″ indicates a binding site to CY2 of Formula 1A and * indicates a binding site to CY4 of Formula 1A, and

in Formulae CY4(1) to CY4(67), * indicates a binding site to CY3 of Formula 1A.

In one or more embodiments, the organometallic compound may be represented by Formula 1:

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In Formula 1,

M, X₁to X₄, Y₁, Y₃to Y₅, CY1 to CY5, X₅₁(wherein X₅₁in Formula 1 is not N, C(R₇), Si(R₇), or Ge(R₇)), 1 to L₄, L₇, b1 to b4, b7, R₁to R₄, c1 to c4, and a1 to a4 may each independently be the same as described herein,

Y₂, Y₆to Y₉may each independently be N or C,

Y₁₀and Y₁₁may each independently be C, N, O, or S, and

a bond between Y₁and Y₁₀, a bond between Y₁and Y₂, a bond between X₂and Y₃, a bond between X₂and Y₄, a bond between Y₄and Y₅, a bond between Y₄and Y₆, a bond between X₃and Y₇, a bond between X₃and Y₅, a bond between X₄and Y₉, and a bond between X₄and Y₁₁may each independently be a single bond or a double bond, and a bond between Y₂and Y₃, a bond between Y₆and Y₇, and a bond between Y₈and Y₉may each be a single bond.

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

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In Formula 1-1,

M, X₁to X₃, and X₅₁may each independently be the same as described herein,

X₁₁may be N or C-[(L₁₁)_b11-(R₁₁)_c11], X₁₂may be N or C-[(L₁₂)_b12-(R₁₂)_c12], X₁₃may be N or C-[(L₁₃)_b13-(R₁₃)_c13], X₁₄may be N or C-[(L₁₄)_b14-(R₁₄)_c14],

L₁₁to L₁₄, b11 to b14, R₁₁to R₁₄and c11 to c14 may each independently be the same as described in connection with L₁, b1, R₁, and c1,

X₂₁may be N or C-[(L₂₁)_b21-(R₂₁)_c21], X₂₂may be N or C-[(L₂₂)_b22-(R₂₂)_c22], X₂₃may be N or C-[(L₂₃)_b23-(R₂₃)_c23],

L₂₁to L₂₃, b21 to b23, R₂₁to R₂₃and c21 to c23 may each independently be the same as described in connection with L₂, b2, R₂, and c2,

X₃₁may be N or C-[(L₃₁)_b31-(R₃₁)_c31], X₃₂may be N or C-[(L₃₂)_b32-(R₃₂)_c32], X₃₃may be N or C-[(L₃₃)_b33-(R₃₃)_c33],

L₃₁to L₃₃, b31 to b33, R₃₁to R₃₃and c31 to c33 may each independently be the same as described in connection with L₃, b3, R₃, and c3,

X₄₁may be N or C-[(L₄₁)_b41-(R₄₁)_c41], X₄₂may be N or C-[(L₄₂)_b42-(R₄₂)_c42], X₄₃may be N or C-[(L₄₃)_b43-(R₄₃)_c43], X₄₄may be N or C-[(L₄₄)_b44-(R₄₄)_c44],

L₄₁to L₄₄, b41 to b44, R₄₁to R₄₄and c41 to c44 may each independently be the same as described in connection with L₄, b4, R₄, and c4,

two of R₁₁to R₁₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of R₂₁to R₂₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group,

two of R₃₁to R₃₃may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, and

two of R₄₁to R₄₄may optionally be linked to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group.

For example, in Formula 1-1, i) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of R₁₁to R₁₄, ii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of R₂₁to R₂₃, iii) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of R₃₁to R₃₂, iv) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two of R₄₁to R₄₄, and v) a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀heterocyclic group, formed by linking two or more neighboring groups selected from R₁₁to R₁₄, R₂₁to R₂₃, R₃₁to R₃₃, and R₄₁to R₄₄may each independently be selected from:

but embodiments of the present disclosure are not limited thereto.

R_1amay be the same as described in connection with R₁.

For example, the organometallic compound may be represented by Formula 1-1, and in Formula 1-1,

X₁₁may be C-[(L₁₁)_b11-(R₁₁)_c11], X₁₂may be C-[(L₁₂)_b12-(R₁₂)_c12], X₁₃may be C-[(L₁₃)_b13-(R₁₃)_c13], X₁₄may be C-[(L₁₄)_b14-(R₁₄)_c14], X₂₁may be C-[(L₂₁)_b21-(R₂₁)_c21], X₂₂may be C-[(L₂₂)_b22-(R₂₂)_c22], X₂₃may be C-[(L₂₃)_b23-(R₂₃)_c23], X₃₁may be C-[(L₃₁)_b31-(R₃₁)_c31], X₃₂may be C-[(L₃₂)_b32-(R₃₂)_c32], X₃₃may be C-[(L₃₃)_b33-(R₃₃)_c33], X₄₁may be C-[(L₄₁)_b41-(R₄₁)_c41], X₄₂may be C-[(L₄₂)_b42-(R₄₂)_c42], X₄₃may be C-[(L₄₃)_b43-(R₄₃)_c43], X₄₄may be C-[(L₄₄)_b44-(R₄₄)_c44],

X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7],

b7 may be 0, c7 may be 1,

R₇may be selected from:

a C₁-C₃₀alkyl group; and

at least one selected from R₁₁to R₁₄, R₂₁to R₂₃, R₃₁to R₃₃, and R₄₁to R₄₄may be selected from:

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments the organometallic compound may be represented by Formula 1-1, and in Formula 1-1,

X₅₁may be O, S, or N-[(L₇)_b7-(R₇)_c7],

b7 may be 0, c7 may be 1,

R₇may be selected from:

a C₁-C₃₀alkyl group; and

R₁₁to R₁₄, R₂₁to R₂₃, R₃₁to R₃₃, and R₄₁to R₄₄may each independently be selected from hydrogen, deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-19, groups represented by Formulae 10-1 to 10-167, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₅)(Q₇), and —P(═O)(Q₈)(Q₉) (wherein Q₁to Q₉are each independently the same as described herein), and

in Formula 1-1, at least one selected from R₁₁to R₁₄, R₂₁to R₂₃, R₃₁to R₃₃, and R₄₁to R₄₄may each independently be selected from groups represented by Formulae 10-1 to 10-167, but embodiments of the present disclosure are not limited thereto.

For example, the organometallic compound may be one selected from Compounds 1-1 to 1-88, Compounds 2-1 to 2-47, and Compounds 3-1 to 3-582, but embodiments of the present disclosure are not limited thereto:

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Formula 1A includes a 5-membered ring represented by CY5, Formula 1A includes a cyclometallated ring formed by CY5, CY2, CY3, and M in Formula 1A which is a 6-membered ring (see Formula 1A′). Accordingly, a stable bond angle may be formed between a tetradentate ligand and a metal in Formula 1A, thereby improving a molecular stability of the organometallic compound represented by Formula 1A:

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In addition, in Formula 1A, in cases where i) M is Pt, ii) X₁is O, iii) X₂and X₄are each N, X₃is C, a bond between X₂and M and a bond between X₄and M are each a coordinate bond, and a bond between X₃and M is a covalent bond, iv) Y₁to Y₅are each C, v) a bond between Y₅and X₅₁and a bond between Y₃and X₅₁are each a single bond, vi) CY1, CY2, and CY3 are each a benzene group, and CY4 is a pyridine group, vii) X₅₁is O, S, or N-[(L₇)_b7-(R₇)_c7], and viii) b7 is 0, c7 is 1, and R₇is a substituted or unsubstituted C₁-C₆₀alkyl group, a1 to a4 may each independently be 1, 2, 3, 4, or 5, and at least one selected from R₁to R₄may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group. Thus, the organometallic compound represented by Formula 1A may have improved molecular orientation, and in this regard, an electronic device, for example, an organic light-emitting device, which includes the organometallic compound represented by Formula 1A, may have improved efficiency and lifespan.

X₄in Formula 1A may be N. Thus, the organometallic compound represented by Formula 1A may emit a phosphorescent light emission having a high luminescent efficiency due to a intermolecular charge transfer mechanism.

Furthermore, CY₄in Formula 1A may not be a benzimidazole group. In an embodiment, CY₄in Formula 1A may be selected from a) 6-membered ring, b) a condensed ring having two or more 6-membered rings that are condensed to each other, and c) a condensed ring having two or more 6-membered rings and one 5-membered ring that are condensed to each other, wherein the 6-membered ring may be selected from a cyclohexane group, a cyclohexene group, an adamantane group, a norbornane group, a norbornene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group, and the 5-membered ring may be selected from a cyclopentane group, a cyclopentene group, a cyclopentadiene group, a furan group, a thiophene group, a silole 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, and a thiadiazole group. Thus, the organometallic compound represented by Formula 1A may emit a phosphorescent light emission having a high luminescent efficiency due to an intermolecular charge transfer mechanism.

For example, a highest occupied molecular orbital (HOMO) energy level, a lowest unoccupied molecular orbital (LUMO) energy level, a singlet (Si) energy level, and a triplet (Ti) energy level of each of Compounds 1-28, 1-30, 1-17, 1-9, and 1-12 were evaluated by using a density functional theory (DFT) method of a Gaussian program (a structure was optimized at a B3LYP, 6-31G(d,p) level). Evaluation results thereof are shown in Table 1.

TABLE 1

Compound
HOMO
LUMO
S₁energy level
T₁energy level

No.
(eV)
(eV)
(eV)
(eV)

1-28
−4.869
−1.589
2.728
2.472

1-30
−4.994
−1.793
2.661
2.439

1-17
−4.794
−1.528
2.721
2.47

1-9
−4.782
−1.528
2.719
2.466

1-12
−4.813
−1.598
2.693
2.395

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Referring to Table 1, it has been determined that the organometallic compound represented by Formula 1A has electrical characteristics suitable for use as a dopant of an electronic device, for example, an organic light-emitting device.

Synthesis methods of the organometallic compound represented by Formula 1A may be recognizable by one of ordinary skill in the art by referring to Synthesis Examples provided below.

The organometallic compound represented by Formula 1A is suitable for use in an organic layer of an organic light-emitting device, for example, for use as a dopant in an emission layer of the organic layer. Thus, another aspect of the present disclosure provides an organic light-emitting device that includes: a first electrode; a second electrode; and an organic layer that is disposed between the first electrode and the second electrode and includes an emission layer, wherein the organic layer includes at least one of the organometallic compound represented by Formula 1A.

The organic light-emitting device may have, due to the inclusion of an organic layer including the organometallic compound represented by Formula 1A, a low driving voltage, high efficiency, high power, high quantum efficiency, a long lifespan, a low roll-off ratio, and excellent color purity.

The organometallic compound represented by Formula 1A may be used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Formula 1A may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (that is, an amount of the organometallic compound represented by Formula 1A is smaller than an amount of the host).

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

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

The first electrode may be an anode, which is a hole injection electrode, and the second electrode may be a cathode, which is an electron injection electrode; or the first electrode may be a cathode, which is an electron injection electrode, and the second electrode may be an anode, which is a hole injection electrode.

For example, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode, and the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

The term “organic layer” as used herein refers to a single layer and/or a plurality of layers disposed between the first electrode and the second electrode of the organic light-emitting device. The “organic layer” may include, in addition to an organic compound, an organometallic complex including metal.

The FIGURE is a schematic view of an organic light-emitting device 10 according to an embodiment. Hereinafter, the structure of an organic light-emitting device according to an embodiment and a method of manufacturing an organic light-emitting device according to an embodiment will be described in connection with the FIGURE. The organic light-emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked.

A substrate may be additionally disposed under the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate that is used in general organic light-emitting devices may be used, and the substrate may be a glass substrate or a transparent plastic substrate, each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance.

The first electrode 11 may be formed by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material for forming the first electrode 11 may be selected from materials with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode may be, for example, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO₂), and zinc oxide (ZnO). In one or more embodiments, magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as the material for forming the first electrode.

The first electrode 11 may have a single-layered structure or a multi-layered structure including two or more layers. For example, the first electrode 11 may have a three-layered structure of ITO/Ag/ITO, but the structure of the first electrode 110 is not limited thereto.

The organic layer 15 is disposed on the first electrode 11.

The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

The hole transport region may be disposed between the first electrode 11 and the emission layer.

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

The hole transport region may include only either a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may have a hole injection layer/hole transport layer structure or a hole injection layer/hole transport layer/electron blocking layer structure, which are sequentially stacked in this stated order from the first electrode 11.

A hole injection layer may be formed on the first electrode 11 by using one or more suitable methods selected from vacuum deposition, spin coating, casting, or Langmuir-Blodgett (LB) deposition.

When a hole injection layer is formed by vacuum deposition, the deposition conditions may vary according to a compound that is used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a vacuum pressure of about 10⁻⁸torr to about 10⁻³torr, and a deposition rate of about 0.01 Angstroms per second (A/sec) to about 100 Å/sec. However, the deposition conditions are not limited thereto.

When the hole injection layer is formed using spin coating, coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal properties of the hole injection layer. For example, a coating speed may be from about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a temperature at which a heat treatment is performed to remove a solvent after coating may be from about 80° C. to about 200° C. However, the coating conditions are not limited thereto.

Conditions for forming a hole transport layer and an electron blocking layer may be understood by referring to conditions for forming the hole injection layer.

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

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In Formula 201, Ar₁₀₁and Ar₁₀₂may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, and a pentacenylene group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₁₀arylalkyl group, a C₁-C₁₀heteroaryl group, a C₂-C₁₀heteroaryloxy group, a C₂-C₁₀heteroarylthio group, a C₃-C₁₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

In Formula 201, xa and xb may each independently be an integer from 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1 and xb may be 0, but embodiments of the present disclosure are not limited thereto.

In Formulae 201 and 202, R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄may each independently be selected from:

hydrogen, deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, a propyl group, a butyl group, pentyl group, a hexyl group, and the like), and a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and the like);

a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, and a phosphoric acid group or a salt thereof; a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, a fluorenyl group, and a pyrenyl group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₁₀alkyl group, and a C₁-C₁₀alkoxy group; but embodiments of the present disclosure are not limited thereto.

In Formula 201, R₁₀₉may be selected from:

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group; and

a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, and a pyridinyl group.

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

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In Formula 201A, R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉may be understood by referring to the description provided herein.

For example, the compound represented by Formula 201, and the compound represented by Formula 202 may include Compounds HT1 to HT20 below, but embodiments of the present disclosure are not limited thereto:

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A thickness of the hole transport region may be in a range of about 100 Angstroms (Å) to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the thickness of the hole injection layer may be in a range of about 100 Å to about 10,000 Å, and 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, and for example, about 100 Å to about 1,500 Å. While not wishing to be bound by theory, it is understood that when the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transporting characteristics may be obtained without a substantial increase in driving voltage.

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

The charge-generation material may be, for example, a p-dopant. The p-dopant may be one selected from a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are a quinone derivative, such as tetracyanoquinonedimethane (TCNQ) or 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinonedimethane (F4-TCNQ); a metal oxide, such as a tungsten oxide or a molybdenium oxide; and a cyano group-containing compound, such as Compound HT-D1 or Compound HT-D2 below, but embodiments of the present disclosure are not limited thereto:

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The hole transport region may include a buffer layer.

The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of a formed organic light-emitting device may be improved.

Then, an emission layer may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, or the like. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied in forming the hole injection layer although the deposition or coating conditions may vary according to a material that is used to form the emission layer.

Meanwhile, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be selected from materials for the hole transport region described above and materials for a host to be explained later. However, the material for the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for the electron blocking layer may be mCP, which will be explained later.

The emission layer may include a host and a dopant, and the dopant may include the organometallic compound represented by Formula 1A.

The host may include at least one selected from TPBi, TBADN, ADN (also referred to as “DNA”), CBP, CDBP, TCP, mCP, Compound H50, and Compound H51:

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

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In Formula 301, Ar₁₁₁and Ar₁₁₂may each independently be selected from:

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group; and

a phenylene group, a naphthylene group, a phenanthrenylene group, and a pyrenylene group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.

In Formula 301, Ar₁₁₃to Ar₁₁may each independently be selected from:

a C₁-C₁₀alkyl group, a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group; and

a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group, each substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group.

In Formula 301, g, h, i, and j may each independently be an integer from 0 to 4, for example, 0, 1, or 2.

In Formula 301, Ar₁₁₃to Ar₁₁may each independently be selected from:

a C₁-C₁₀alkyl group substituted with at least one selected from a phenyl group, a naphthyl group, and an anthracenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group;

a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group, each substituted with at least one selected from deuterium, —F, —C, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, and a fluorenyl group; and

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but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, the host may include a compound represented by Formula 302:

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In Formula 302, Ar₁₂₂to Ar₁₂₅are the same as described in detail in connection with Ar₁₁₃in Formula 301.

In Formula 302, Ar₁₂₆and Ar₁₂7 may each independently be a C₁-C₁₀alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may be 0, 1, or 2.

The compound represented by Formula 301 and the compound represented by Formula 302 may include Compounds H1 to H42 below, but embodiments of the present disclosure are not limited thereto.

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When the organic light-emitting device is a full-color organic light-emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, due to a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, the emission layer may emit white light.

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

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 A, for example, about 200 Å to about 600 Å. While not wishing to be bound by theory, it is understood that when the thickness of the emission layer is within this range, excellent light-emission characteristics may be obtained without a substantial increase in driving voltage.

Then, an electron transport region may be disposed on the emission layer.

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

For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a single-layered structure or a multi-layered structure including two or more different materials.

Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer which constitute the electron transport region may be understood by referring to the conditions for forming the hole injection layer.

When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of BCP, Bphen, and BAlq but embodiments of the present disclosure are not limited thereto:

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A thickness of the hole blocking layer may be in a range of about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 Å. While not wishing to be bound by theory, it is understood that when the thickness of the hole blocking layer is within these ranges, the hole blocking layer may have improved hole blocking ability without a substantial increase in driving voltage.

The electron transport layer may further include at least one selected from BCP, Bphen, Alq3, BAlq, TAZ, and NTAZ:

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In one or more embodiments, the electron transport layer may include at least one of Compounds ET1 to ET25, but embodiments of the present disclosure are not limited thereto:

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A 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. While not wishing to be bound by theory, it is understood that when the thickness of the electron transport layer is within the range described above, the electron transport layer may have satisfactory electron transport characteristics without a substantial increase in driving voltage.

Also, the electron transport layer may further include, in addition to the materials described above, a metal-containing material.

The metal-containing material may include a Li complex. The Li complex may include, for example, Compound ET-D1 (lithium 8-hydroxyquinolate, LiQ) or Compound ET-D2:

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The electron transport region may include an electron injection layer that promotes flow of electrons from the second electrode 19 thereinto.

The electron injection layer may include at least one selected from LiF, NaCl, CsF, Li₂, and BaO.

A thickness of the electron injection layer may be in a range of about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. While not wishing to be bound by theory, it is understood that when the thickness of the electron injection layer is within the range described above, the electron injection layer may have satisfactory electron injection characteristics without a substantial increase in driving voltage.

The second electrode 19 is disposed on the organic layer 15. The second electrode 19 may be a cathode. A material for forming the second electrode 19 may be selected from metal, an alloy, an electrically conductive compound, and a combination thereof, which have a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca), magnesium-indium (Mg—In), or magnesium-silver (Mg—Ag) may be used as a material for forming the second electrode 19. In one or more embodiments, to manufacture a top-emission type light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.

Hereinbefore, the organic light-emitting device has been described with reference to the FIGURE, but embodiments of the present disclosure are not limited thereto.

Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by Formula 1A.

The organometallic compound represented by Formula 1A provides high luminescent efficiency. Accordingly, a diagnostic composition including the organometallic compound may have high diagnostic efficiency.

The diagnostic composition may be used in various applications including a diagnosis kit, a diagnosis reagent, a biosensor, and a biomarker.

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

The term “C₁-C₁₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₁₀alkyl group), and non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy (iso-propoxy) group.

The term “C₂-C₁₀alkenyl group” as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon double bond in the middle or at the terminus of the C₂-C₁₀alkyl group, and examples thereof include an ethenyl group, a propenyl group, and a butenyl group. The term “C₂-C₁₀alkenylene group” as used herein refers to a divalent group having the same structure as the C₂-C₁₀alkenyl group.

The term “C₂-C₁₀alkynyl group” as used herein refers to a hydrocarbon group formed by including at least one carbon-carbon triple bond in the middle or at the terminus of the C₂-C₁₀alkyl group, and examples thereof include an ethynyl group, and a propynyl group. The term “C₂-C₁₀alkynylene group” as used herein refers to a divalent group having the same structure as the C₂-C₁₀alkynyl group.

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

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

The term “C₃-C₁₀cycloalkenyl group” as used herein refers to a monovalent monocyclic group that has 3 to 10 carbon atoms and at least one carbon-carbon double bond in the ring thereof, that is non-aromatic, and non-limiting examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. The term “C₃-C₁₀cycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₃-C₁₀cycloalkenyl group.

The term “C₁-C₁₀heterocycloalkenyl group” as used herein refers to a monovalent monocyclic group that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, 1 to 10 carbon atoms, and at least one carbon-carbon double bond in its ring. Examples of the C₁-C₁₀heterocycloalkenyl group are a 2,3-dihydrofuranyl group, and a 2,3-dihydrothiophenyl group. The term “C₁-C₁₀heterocycloalkenylene group” as used herein refers to a divalent group having the same structure as the C₁-C₁₀heterocycloalkenyl group.

The term “C₆-C₆₀aryl group” as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and the term “C₆-C₆₀arylene group” as used herein refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. Non-limiting examples of the C₆-C₆₀aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. When the C₆-C₆₀aryl group and the C₆-C₆₀arylene group each include two or more rings, the rings may be fused to each other.

The term “C₁-C₆₀heteroaryl group” as used herein refers to a monovalent group having an aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. The term “C₁-C₆₀heteroarylene group” as used herein refers to a divalent group having an aromatic system that has at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and 1 to 60 carbon atoms. Non-limiting examples of the C₁-C₆₀heteroaryl group include a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, and an isoquinolinyl group. When the C₁-C₆₀heteroaryl group and the C₁-C₆₀heteroarylene group each include two or more rings, the rings may be fused to each other.

The term “C₆-C₆₀aryloxy group” as used herein indicates —OA₁₀₂(wherein A₁₀₂is the C₆-C₆₀aryl group), the term “C₆-C₆₀arylthio group” as used herein indicates —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group), and the term “C₇-C₆₀arylalkyl group” as used herein indicates -A₁₀₄A₁₀₅(wherein A₁₀₄is the C₆-C₅₉aryl group and A₁₀₅is the C₁-C₅₃alkyl group).

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

The term “monovalent non-aromatic condensed heteropolycyclic group” as used herein refers to a monovalent group (for example, having 2 to 60 carbon atoms) having two or more rings condensed to each other, a heteroatom selected from N, O, P, Si, and S, other than carbon atoms, as a ring-forming atom, and no aromaticity in its entire molecular structure. Non-limiting examples of the monovalent non-aromatic condensed heteropolycyclic group include a carbazolyl group. The term “divalent non-aromatic condensed heteropolycyclic group” as used herein refers to a divalent group having the same structure as the monovalent non-aromatic condensed heteropolycyclic group.

The term “C₅-C₃₀carbocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, 5 to 30 carbon atoms only. The C₅-C₃₀carbocyclic group may be a monocyclic group or a polycyclic group.

The term “C₁-C₃₀heterocyclic group” as used herein refers to a saturated or unsaturated cyclic group having, as a ring-forming atom, at least one heteroatom selected from N, O, Si, P, and S other than 1 to 30 carbon atoms. The C₁-C₃₀heterocyclic group may be a monocyclic group or a polycyclic group.

At least one substituent of the substituted C₅-C₃₀carbocyclic group, the substituted C₂-C₃₀heterocyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₇-C₆₀arylalkyl group, the substituted C₁-C₆₀heteroaryl group, the substituted C₂-C₆₀heteroaryloxy group, the substituted C₂-C₆₀heteroarylthio group, the substituted C₃-C₆₀heteroarylalkyl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —S(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₇-C₆₀arylalkyl group, a C₁-C₆₀heteroaryl group, a C₂-C₆₀heteroaryloxy group, a C₂-C₆₀heteroarylthio group, a C₃-C₆₀heteroarylalkyl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), —B(Q₂₆)(Q₂₇), and —P(═O)(Q₂₈)(Q₂₉); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), —B(Q₃₆)(Q₃₇), and —P(═O)(Q₃₈)(Q₃₉), and

When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraph, the number of carbon atoms in the resulting “substituted” group is defined as the sum of the carbon atoms contained in the original (unsubstituted) group and the carbon atoms (if any) contained in the substituent. For example, when the term “substituted C₁-C₃₀alkyl” refers to a C₁-C₃₀alkyl group substituted with C₆-C₃₀aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C₇-C₆₀.

Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Examples and Examples. However, the organic light-emitting device is not limited thereto. The wording “B was used instead of A” used in describing Synthesis Examples means that the number of molar equivalents of A used was identical to the number of molar equivalents of B used.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 1-1

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Synthesis of Intermediate A (2-(5-bromo-3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane)

10 grams (g) (0.024 moles, mol) of 3,5-dibromo-3′,5′-di-tert-butyl-1,1′-biphenyl and 9.0 g (0.036 mol, 1.5 equivalents, equiv.) of bispinacolato diboron were added to a flask, and 4.6 g (0.048 mol, 2 equiv.) of potassium acetate and 0.96 g (0.05 equiv.) of PdCl₂(dppf) were added to the flask. Then, 100 milliliters (ml) of toluene was added thereto, and the resultant mixture was refluxed overnight at a temperature of 100° C. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered therefrom. The filtrate was washed by using ethyl acetate (EA)/H₂O, and purified by column chromatography to obtain 5.6 g (yield: 50%) of Intermediate A. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.

HRMS (MALDI) calcd for C₂₆H₃₆BBrO₂: m/z 470.1992, found: 470.1994

Synthesis of Intermediate B (2-(5-bromo-3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-yl)pyridine)

5.6 g (0.014 mol, 1.2 equiv.) of Intermediate A, 1.9 g (0.012 mol, 1 equiv.) of 2-bromopyridine, 0.61 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 3.1 g (0.036 mol, 3 equiv.) of potassium carbonate were dissolved in a solvent (25 mL, 0.8 molar, M) in which tetrahydrofuran (THF) and distilled water (H₂O) were mixed at a ratio of 3:1, and the mixed solution was refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered therefrom. The filtrate was washed by using EA/H₂O, and purified by column chromatography (while increasing a volume rate of methylene chloride (MC)/hexane (Hex) to between 25% and 50%) to obtain 4 g (yield: 80%) of Intermediate B. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.

HRMS (MALDI) calcd for C₂₅H₂₆BrN: m/z 421.1405, found: 421.1407

Synthesis of Intermediate C (2-(3′,5′-di-tert-butyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-3-yl)pyridine)

4 g (0.009 mol) of Intermediate B (2-(5-bromo-3′,5′-di-tert-butyl-[1,1′-biphenyl]-3-yl)pyridine) and 3.6 g (0.014 mol, 1.5 equiv.) of bispinacolato diboron were added to a flask, and 1.9 g (0.019 mol, 2 equiv.) of potassium acetate and 0.39 g (0.05 equiv.) of PdCl₂(dppf) were added to the flask. Then, 32 mL of toluene was added thereto, and the resultant mixture was refluxed overnight at a temperature of 100° C. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered therefrom. The filtrate was washed by using EA/H₂O, and purified by column chromatography to obtain 2.4 g (yield: 56%) of Intermediate C. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.

HRMS (MALDI) calcd for C₃₁H₄₀BNO₂: m/z 469.3152, found: 469.3155

Synthesis of Intermediate E (2-(4-(3′, 5′-di-tert-butyl-5-(pyridin-2-yl)-[1,1′-biphenyl]-3-yl)-1-methyl-1H-benzo[d]imidazol-2-yl)phenol)

2.4 g (0.005 mol, 1.2 equiv.) of Intermediate C, 1.3 g (0.004 mol, 1 equiv.) of Intermediate D (2-(4-bromo-1-methyl-1H-benzo[d]imidazol-2-yl)phenol), 0.35 g (0.001 mol, 0.07 equiv.) of tetrakis(triphenylphosphine)palladium(0), and 1.8 g (0.013 mol, 3 equiv.) of potassium carbonate were dissolved in 20 mL of a solvent in which tetrahydrofuran (THF) and distilled water (H₂O) were mixed at a ratio of 3:1, and the mixed solution was refluxed for 12 hours. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered therefrom. The filtrate was washed by using EA/H₂O, and purified by column chromatography (while increasing a volume rate of MC/Hex to between 25% and 50%) to obtain 1.7 g (yield: 73%) of Intermediate E. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.

HRMS (MALDI) calcd for C₃₉H₃₉N₃O: m/z 565.3093, found: 565.3096

Synthesis of Compound 1-1

1.4 g (2.5 mmol) of Intermediate E and 1.23 g (3 mmol, 1.2 equiv.) of K₂PtCl₄were dissolved in 25 mL of a solvent in which 20 mL of AcOH and 5 mL of H₂O were mixed, and the mixed solution was refluxed for 16 hours. The refluxed mixture thus obtained was cooled to room temperature, and the precipitate was filtered therefrom. The precipitate was dissolved again in MC and washed by using H₂O. The organic layer was purified by column chromatography (MC 40%, EA 1%, Hex 59%) to obtain 0.7 g (purity: 99% or more) of Compound 1-1. The obtained product was confirmed by Mass Spectrometry and HPLC analysis.

HRMS (MALDI) calcd for C₃₉H₃₇N₃OPt: m/z 758.26, found: 758.26

Synthesis Example 2: Synthesis of Compound 1-28

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Synthesis of Intermediate H

Intermediate H was synthesized in the same manner as Intermediate E in Synthesis Example 1, except that Intermediate F and Intermediate G were used instead of Intermediate D and Intermediate C, respectively.

HRMS (MALDI) calcd for C₄₂H₄₇N₃OSi: m/z 637.3488, found: 637.3485

Synthesis of Compound 1-28

Compound 1-28 (1.5 g, yield: 52%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate H was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₂H₄₅N₃OPtSi: m/z 830.2980, found: 830.2983

Synthesis Example 3: Synthesis of Compound 1-30

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Synthesis of Intermediate J

Intermediate J was synthesized in the same manner as Intermediate E in Synthesis Example 1, except that Intermediate F and Intermediate I were used instead of Intermediate D and Intermediate C, respectively.

HRMS (MALDI) calcd for C₄₀H₄₁N₃O: m/z 579.3250, found: 579.3252

Synthesis of Compound 1-30

Compound 1-30 (1.2 g, yield: 56%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate J was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₀H₃₉N₃OPt: m/z 772.2741, found: 772.2745

Synthesis Example 4: Synthesis of Compound 1-17

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Synthesis of Intermediate L

Intermediate L was synthesized in the same manner as Intermediate E in Synthesis Example 1, except that Intermediate F and Intermediate K were used instead of Intermediate D and Intermediate C, respectively.

HRMS (MALDI) calcd for C₄₆H₄₅N₃O: m/z 655.3563, found: 655.3567

Synthesis of Compound 1-17

Compound 1-17 (1.7 g, yield: 57%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate L was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₆H₄₃N₃OPt: m/z 848.3054, found: 848.3053

Synthesis Example 5: Synthesis of Compound 1-9

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Synthesis of Intermediate N

Intermediate N was synthesized in the same manner as Intermediate E in Synthesis Example 1, except that Intermediate F and Intermediate M were used instead of Intermediate D and Intermediate C, respectively.

HRMS (MALDI) calcd C₄₈H₅N₃OSi: m/z 713.3801, found: 713.3804

Synthesis of Compound 1-9

Compound 1-9 (1.2 g, yield: 52%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate N was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₈H₄N₃OPtSi: m/z 906.3293, found: 906.3297

Synthesis Example 6: Synthesis of Compound 1-12

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Synthesis of Intermediate R

Intermediate R was synthesized in the same manner as Intermediate E in

Synthesis Example 1, Except that Intermediate F and Intermediate Q were Used Instead of Intermediate D and Intermediate C, Respectively

HRMS (MALDI) calcd for C₄₅H₄₃N₃O: m/z 641.3406, found: 641.3408

Synthesis of Compound 1-12

Compound 1-12 (1.0 g, yield: 45%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate R was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₅H₄₁N₃OPt: m/z 834.2897, found: 834.2892

Synthesis Example 7: Synthesis of Compound 3-417

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Synthesis of Intermediate U

Intermediate U was synthesized in the same manner as Intermediate E in Synthesis Example 1, except that Intermediate S and Intermediate T were used instead of Intermediate D and Intermediate C, respectively.

HRMS (MALDI) calcd for C₅₁H₄₉N₃₀: m/z 719.3876, found: 719.3874

Synthesis of Compound 3-417

Compound 3-417 (1.2 g, yield: 55%) was synthesized in the same manner as Compound 1-1 in Synthesis Example 1, except that Intermediate U was used instead of Intermediate E.

HRMS (MALDI) calcd for C₄₅H₄₁N₃OPt: m/z 912.3367, found: 912.3369

Example 1

An ITO glass substrate on which an ITO electrode (anode) is deposited was cut to a size of 50 mm×50 mm×0.5 mm (mm=millimeter), sonicated with acetone, iso-propyl alcohol, and pure water each for 15 minutes, and cleaned by exposure to ultraviolet (UV) rays and ozone for 30 minutes.

Then, m-MTDATA was deposited on an ITO electrode (anode) of the glass substrate at a deposition rate of 1 Angstroms per second (A/sec) to form a hole injection layer having a thickness of 600 Angstroms (Å), and α-NPD (also referred to as NPB) was deposited on the hole injection layer at a deposition rate of 1 Å/sec to form a hole transport layer having a thickness of 250 Å.

Compound 1-28 (dopant) and CBP (host) were co-deposited on the hole transport layer at a deposition rate of 0.1 Å/sec and 1 Å/sec, respectively, to form an emission layer having a thickness of 400 Å.

BAlq was deposited on the emission layer at a deposition rate of 1 Å/sec to form a hole blocking layer having a thickness of 50 Å, Alq₃was deposited on the hole blocking layer to form an electron transport layer having a thickness of 300 Å, LiF was deposited on the electron transport layer to form an electron injection layer having a thickness of 10 Å, and A1 was vacuum-deposited on the electron injection layer to form a second electrode (cathode) having a thickness of 1,200 Å, thereby completing the manufacture of an organic light-emitting device having a structure of ITO/m-MTDATA (600 Å)/α-NPD (250 Å)/CBP+Compound 1-28 (10 wt %) (400 Å)/BAlq (50 Å)/Alq₃(300 Å)/LiF (10 Å)/A1 (1,200 Å).

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Examples 2 to 6 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in the same manner as in Example 1, except that Compounds shown in Table 2 were each used instead of Compound 1-28 as a dopant in forming an emission layer.

Evaluation Example 1: Evaluation of Characteristics of Organic Light-Emitting Devices

The driving voltage, luminescent efficiency, quantum emission efficiency, roll-off ratio, and lifespan (T₉₅) characteristics of the organic light-emitting device manufactured according to Examples 1 to 6 and Comparative Examples 1 to 4 were evaluated, and results thereof are shown in Table 2. Devices used for the evaluation were a current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A). The lifespan (T₉₅) (at 6,000 nit) indicates an amount of time that lapsed when luminance was 95% of initial luminance (100%) in a relative manner with respect to those of the organic light-emitting device of Example 6. The roll-off ratio was calculated according to Equation 20. The luminescence efficiency are also provided in a relative manner with respect to those of the organic light-emitting device of Example 5.

Roll off={1−(efficiency at 9,000 nit/maximum light-emission efficiency)}×100% Equation 20

TABLE 2

Luminescent

Lifespan

efficiency
Quantum

(%)

Driving
(%)
emission
Roll-off
(T₉₅)

voltage
(relative
efficiency
ratio
(relative

Dopant
(V)
value)
(%)
(%)
value)

Example 1
Compound 1-28
4.11
81%
84%
14%
24%

Example 2
Compound 1-30
4.14
80%
89%
15%
11%

Example 3
Compound 1-17
4.10
84%
87%
11%
28%

Example 4
Compound 1-9
3.90
91%
91%
9%
15%

Example 5
Compound 1-12
3.82
100%
100%
6%
75%

Example 6
Compound 3-417
3.94
92%
94%
10%
100%

Comparative
Compound A
4.57
50%
69%
11%
18%

Example 1

Comparative
Compound B
4.00
61%
56%
9%
0%

Example 2

Comparative
Compound C
4.97
62%
61%
35%
4%

Example 3

Comparative
Compound D
4.78
57%
60%
19%
0%

Example 4

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Referring to Table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 6 have improved driving voltage, luminescent efficiency, quantum emission efficiency, roll-off ratio, and lifespan characteristics, as compared with those of the organic light-emitting devices of Comparative Examples 1 to 4.

As described above, an organometallic compound according to embodiments of the present disclosure has excellent electrical characteristics and thermal stability, and accordingly, an organic light-emitting device including the organometallic compound may have excellent driving voltage, light-emission efficiency, quantum emission efficiency, roll-off ratio, and lifespan characteristics. In addition, due to excellent phosphorescent luminescence characteristics of the organometallic compound, the organometallic compound may provide a diagnostic composition having high diagnostic efficiency.

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.

	Number	Date	Country
Parent	15641299	Jul 2017	US
Child	17128400		US

ORGANOMETALLIC COMPOUND, ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME, AND DIAGNOSTIC COMPOSITION INCLUDING THE ORGANOMETALLIC COMPOUND

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