ORGANIC LIGHT-EMITTING DEVICE

BACKGROUND
1. Field

One or more embodiments relate to an organic light-emitting device.

2. Description of the Related Art

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

An example of such organic light-emitting devices 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 transition from an excited state to a ground state, thereby generating light.

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 high-quality organic light-emitting device.

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

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

a first electrode;

a second electrode facing the first electrode; and

an emission layer disposed between the first electrode and the second electrode, the emission layer including an emission layer,

wherein the organic layer includes:

i) an organometallic compound represented by Formula 1; and

ii) at least one selected from a first compound represented by Formula 51, a second compound represented by Formula 61, a third compound represented by Formula 81, and a fourth compound represented by Formula 91:

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M in Formula 1 may be selected from iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), and rhodium (Rh),

in Formula 1, L₁may be a ligand represented by Formula 2A, and n1 may be 1, 2, or 3, wherein when n1 is two or more, two or more groups L₁may be identical to or different from each other,

in Formula 1, L₂may be selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand, and a tetravalent organic ligand, and n2 may be 0, 1, 2, 3, or 4, wherein when n2 is two or more, two or more groups L₂may be identical to or different from each other,

L₁and L₂in Formula 1 may be different from each other,

R₁to R₃in Formula 2A may each independently be selected from 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, and —Si(Q₅₁)(Q₅₂)(Q₅₃),

X₁in Formula 2A may be selected from O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃),

in Formula 2A, Y₁may be N, C(R₄₁), or C linked to a pyridine ring, Y₂may be N, C(R₄₂), or C linked to a pyridine ring, Y₃may be N, C(R₄₃), or C linked to a pyridine ring, Y₄may be N, C(R₄₄), or C linked to a pyridine ring, Y₅may be N or C(R₄₅), Y₆may be N or C(R₄₆), Y₇may be N or C(R₄₇), Y₈may be N or C(R₄₅), and one selected from Y₁to Y₄may be C linked to a pyridine ring,

R₁₁, R₂₁to R₂₃, and R₄₁to R₄₈in Formula 2A may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, 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 substituted or unsubstituted C₁-C₆₀alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀alkynyl group, a substituted or unsubstituted C₁-C₆₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀arylthio group, a substituted or unsubstituted C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁)(Q₂), —Si(Q₃)(Q₄)(Q₅), —B(Q₆)(Q₇), and —P(═O)(Q₈)(Q₉),

two or more groups R₁₁may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring,

two or more selected from R₄₁to R₄₄may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring,

two or more selected from R₄₅to R₄₈may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring,

in Formula 2A, b1 may be an integer selected from 0 to 3, and b4 may be an integer selected from 1 to 4,

* and *′ in Formula 2A each indicate a binding site to M in Formula 1,

ring A₈₁in Formula 61 may be represented by Formula 61A,

ring A62 in Formula 61 may be represented by Formula 61B,

X₆₁in Formula 61B may be N-[(L₆₂)_a62-(R₆₂)_b62], S, O, S(═O), S(═O)₂, C(═O), C(R₆₃)(R₆₄), Si(R₆₃)(R₆₄), P(R₆₃), P(═O)(R₆₃), or C═N(R₆₃),

in Formula 61, X₇₁may be C(R₇₁) or N, X₇₂may be C(R₇₂) or N, X₇₃may be C(R₇₃) or N, X₇₄may be C(R₇₄) or N, X₇₅may be C(R₇₅) or N, X₇₆may be C(R₇₆) or N, X₇₇may be C(R₇₇) or N, and X₇₈may be C(R₇₈) or N,

L₅₁to L₅₃, L₈₁, L₆₂, and L₉₁to L₉₅in Formulae 51, 61, 61B, and 91 may each independently be selected from a single bond, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group,

a51 to a53, a61, a62, and a91 to a95 in Formulae 51, 61, 61B, and 91 may each independently be an integer selected from 1 to 5,

R₅₁to R₅₃, R₈₁to R₆₄, R₇₁to R₇₉, and R₉₁to R₉₅in Formulae 51, 61, 61A, 61B, and 91 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇),

b61, b62, and b79 in Formulae 61A and 61B may each independently be an integer selected from 0 to 3,

in Formula 81, Z₁₁may be N or C(R_a), Z₁₂may be N or C(R_b), Z₁₃may be N or C(R_c), Z₁₄may be N or C(R_d), Z₁₅may be N or C(R_e), Z₁₀may be N or C(R_f), Z₁₇may be N or C(R_g), Z₁₈may be N or C(R_h), Z₁₉may be N or C(R_i), and at least one selected from Z₁₁to Z₁₉may be N,

R₈₁to R₉₀and R_ato R_iin Formula 81 may each independently be selected from hydrogen, deuterium, a substituted or unsubstituted C₁-C₁₀alkyl group, and a substituted or unsubstituted C₆-C₁₂aryl group,

the number of 6-membered rings substituted with a triphenylene core in Formula 81 may be six or less,

L₈₁in Formula 81 may be selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group,

a81 to a83 in Formula 81 may each independently be 0 or 1,

in Formula 81, a81+a82+a83≥1,

at least one selected from L₉₁to L₉₅and R₉₁to R₉₅in Formula 91 may include a carbazole ring or a triphenylene ring, and

at least one substituent selected from a substituent(s) of the substituted C₁-C₂₀alkylene group, the substituted C₂-C₂₀alkenylene group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensed polycyclic group, the substituted divalent non-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, the substituted monovalent non-aromatic condensed heteropolycyclic group, the substituted phenylene group, the substituted biphenylene group, and the substituted terphenylene 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 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, and a C₁-C₆₀alkoxy group;

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —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-C₁₀alkyl group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, 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 C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₂₁)(Q₂₂), —Si(Q₂₃)(Q₂₄)(Q₂₅), and —B(Q₂₆)(Q₂₇); and

—N(Q₃₁)(Q₃₂), —Si(Q₃₃)(Q₃₄)(Q₃₅), and —B(Q₃₆)(Q₃₇),

wherein Q₁to Q₉, Q₁₁to Q₁₉, Q₂₁to Q₂₉, to Q₃₉, and Q₅₁to Q₅₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

BRIEF DESCRIPTION OF THE DRAWINGS

These and/or other aspects will become apparent and more readily appreciated from the following description of the embodiments, taken in conjunction with the accompanying drawing in which:

FIG. 1 is a schematic cross-sectional 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 disclosure. 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.

An organic light-emitting device according to an embodiment may include:

a first electrode;

a second electrode facing the first electrode; and

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

wherein the organic layer includes an emission layer.

The organic layer may include:

i) an organometallic compound represented by Formula 1; and

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Hereinafter, the compounds will be sequentially described.

Organometallic Compound Represented by Formula 1

L₂in Formula 1 may be selected from a monovalent organic ligand, a divalent organic ligand, a trivalent organic ligand, and a tetravalent organic ligand, and n2 may be 0, 1, 2, 3, or 4, wherein when n2 is two or more, two or more groups L₂may be identical to or different from each other.

L₁and L₂in Formula 1 may be different from each other.

In one or more embodiments, n1 in Formula 1 may be 1.

In one or more embodiments, the organometallic compound represented by Formula 1 may be an electrically neutral compound, not a salt consisting of an ionic pair.

In one or more embodiments, in Formula 1, M may be Ir and the sum of n1 and n2 may be 3; or M may be Pt and the sum of n1 and n2 may be 2, and the organometallic compound represented by Formula 1 may be electrically neutral.

In one or more embodiments, R₁to R₃in Formula 2A may each independently be selected from:

a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, and —Si(Q₅₁)(Q₅₂)(Q₅₃);

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy 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-C₁₀alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a 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 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 dibenzocarbazolyl group, an imidazopyridinyl group, and an imidazopyrimidinyl group,

wherein Q₅₁to Q₅₃may 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 iso-butyl 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 are not limited thereto.

In one or more embodiments, R₁and R₃in Formula 2A may each independently be selected from:

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, and —Si(Q₅₁)(Q₅₂)(Q₅₃); and

wherein Q₅₁to Q₅₃may each independently be selected from:

In one or more embodiments, Q₅₁to Q₅₃may each independently be a methyl group or an ethyl group.

In one or more embodiments, in Formula 2A,

R₁to R₃may all be identical to one another;

R₁and R₃may be identical to each other and R₂and R₁may be different from each other; or

R₁to R₃may all be different from one another.

X₁in Formula 2A may be selected from O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃).

In one or more embodiments, X₁in Formula 2A may be selected from O, S, and N(R₂₁).

In one or more embodiments, X₁in Formula 2A may be O, but is not limited thereto.

In one or more embodiments, R₁₁, R₂₁to R₂₃, and R₄₁to R₄₈in Formula 2A may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, —SF₅, 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, and a C₁-C₂₀alkoxy group;

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —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-C₁₀alkyl group, a C₁-C₁₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄heteroaryl 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-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₁₄aryl group, a C₁-C₁₄heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

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

wherein Q₁to Q₉may each independently be selected from a substituted or unsubstituted C₁-C₂₀alkyl group, a substituted or unsubstituted C₁-C₂₀alkoxy group, a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₁₄aryl group, a substituted or unsubstituted C₁-C₁₄heteroaryl 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, to R₂₃, and R₄₁to R₄₈in Formula 2A may each independently be selected from:

—B(Q₆)(Q₇) and —P(═O)(Q₈)(Q₉),

wherein Q₆to Q₉may each independently be selected from:

but embodiments are not limited thereto.

In one or more embodiments, R₁₁, R₂₁to R₂₃, and R₄₁to R₄₈in Formula 2A may 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 iso-butyl 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, and a pyrimidinyl group;

a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, 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, and a pyrimidinyl 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, and a pyrimidinyl group; and —B(Q₆)(Q₇) and —P(═O)(Q₈)(Q₉),

wherein Q₆to Q₉may each independently be selected from:

In one or more embodiments, R₁₁, R₂₁to R₂₃, and R₄₁to R₄₈in Formula 2A may 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 9-17, and groups represented by Formulae 10-1 to 10-30, but embodiments are not limited thereto:

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wherein * in Formulae 9-1 to 9-17 and 10-1 to 10-30 indicates a binding site to a neighboring atom.

In Formula 2A, b1 may be an integer selected from 0 to 3, and b4 may be an integer selected from 1 to 4.

In one or more embodiments, R₂₁to R₂₃in X₁of Formula 2A may each independently be selected from:

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 pyridinyl group, a pyrimidinyl group, and a triazinyl group; and

In Formula 2A, b1 indicates the number of groups R₁₁, wherein when b1 is two or more 2, two or more groups R₁₁may be identical to or different from each other, and b4 indicates the number of groups —Si(R₁)(R₂)(R₃), wherein when b4 is two or more, two or more groups —Si(R₁)(R₂)(R₃) may be identical to or different from each other.

In one or more embodiments, in Formula 2A, b1 may be 0, 1, or 2, and b4 may be 1 or 2, but embodiments are not limited thereto.

In one or more embodiments, in Formula 2A, b1 may be 0, 1, or 2, and b4 may be 1, but embodiments of the present disclosure are not limited thereto.

in Formula 2A, two or more groups R₁₁may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring (for example, a cyclopentane ring, a cyclohexane ring, an adamantane ring, a norbornane ring, a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a pyrene ring, a chrysene ring, or the like), two or more selected from R₄₁to R₄₄may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring (for example, a cyclopentane ring, a cyclohexane ring, an adamantane ring, a norbornane ring, a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a pyrene ring, a chrysene ring, or the like), and two or more selected from R₄₅to R₄₈may optionally be linked to form a saturated or unsaturated C₄-C₆₀ring (for example, a cyclopentane ring, a cyclohexane ring, an adamantane ring, a norbornane ring, a benzene ring, a pyridine ring, a pyrimidine ring, a naphthalene ring, a pyrene ring, a chrysene ring, or the like).

In one or more embodiments, two groups R₁₁in Formula 2A may be linked to form a substituted or unsubstituted cyclohexane or a substituted or unsubstituted benzene ring, but embodiments are not limited thereto.

In one or more embodiments, Y₁to Y₈in Formula 2A may not all be N.

In one or more embodiments, Y₁or Y₃in Formula 2A may be N.

In one or more embodiments, Y₅or Y₆in Formula 2A may be N.

In one or more embodiments, one or two selected from Y₃, Y₅, and Y₆in Formula 2A may be N.

In one or more embodiments, L₁in Formula 1 may be selected from ligands represented by Formulae 2A-1 to 2A-16:

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In Formulae 2A-1 to 2A-16, R₁to R₃, Y₁to Y₈, R₁₁, b1, and b4 are the same as described above, R₁₅is the same as described above in connection with R₁₁, b5 may be an integer selected from 0 to 8, and * and *′ each indicate a binding site to M in Formula 1.

In one or more embodiments,

in Formulae 2A-1 to 2A-16, Y₁may be C(R₄₁), Y₂may be C(R₄₁), Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₅), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14, and 2A-16, Y₁may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14, and 2A-16, Y₁may be C(R₄₁), Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14, and 2A-16, Y₁may be C(R₄₁), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14, and 2A-16, Y₁may be N, Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-1, 2A-2, 2A-4, 2A-5, 2A-6, 2A-8, 2A-9, 2A-10, 2A-12, 2A-13, 2A-14, and 2A-16, Y₁may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-3, 2A-7, 2A-11, and 2A-15, Y₃may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-3, 2A-7, 2A-11, and 2A-15, Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-3, 2A-7, 2A-11, and 2A-15, Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A-3, 2A-7, 2A-11, and 2A-15, Y₃may be N, Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅); or

in Formulae 2A-3, 2A-7, 2A-11, and 2A-15, Y₃may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₅), but embodiments are not limited thereto.

A maximum emission wavelength may be reduced in the following order: i) an organometallic compound including a ligand represented by Formula 2A-4, 2A-8, 2A-12, or 2A-16, ii) an organometallic compound including a ligand represented by Formula 2A-2, 2A-6, 2A-10, or 2A-14, iii) an organometallic compound including a ligand represented by Formula 2A-3, 2A-7, 2A-11, or 2A-15, and iv) an organometallic compound including a ligand represented by Formula 2A-1, 2A-5, 2A-9, or 2A-13. That is, the maximum emission wavelength of the organometallic compound including the ligand represented by Formula 2A-1, 2A-5, 2A-9, or 2A-13 in Formula 2A-1 to 2A-16 is lowest.

In one or more embodiments, L₁in Formula 1 may be selected from ligands represented by Formulae 2AA-1, 2AA-2, 2AA-3, 2AA-4, and 2AB. For example, when L₁in Formula 1 is selected from ligands represented by Formulae 2AA-1 and 2AB, the organic light-emitting device including the organometallic compound represented by Formula 1 may have high efficiency and long lifespan characteristics:

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wherein, in Formulae 2AA-1, 2AA-2, 2AA-3, 2AA-4, and 2AB, R₁to R₃, Y₁to Y₈, R₁₁, and b1 are the same as described above, R₁₅is the same as described above in connection with R₁₁, b5 may be an integer selected from 0 to 8, and * and *′ each indicate a binding site to M in Formula 1.

In one or more embodiments, in Formula 2A-1 to 2A-16, 2AA-1, 2AA-2, 2AA-3, 2AA-4, and 2AB,

R₁to R₃may each independently be selected from:

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

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, and —Si(Q₅₁)(Q₅₂)(Q₅₃); and

wherein Q₅₁to Q₅₃may each independently be selected from:

X₁may be selected from O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃),

Y₁to Y₈are the same as described above,

R₁₁, R₁₅, R₂₁to R₂₃, and R₄₁to R₄₈may each independently be selected from:

—B(Q₆)(Q₇) and —P(═O)(Q₈)(Q₉),

wherein Q₆to Q₉may each independently be selected from:

b1 may be an integer selected from 0 to 3,

b4 may be 1 or 2, and

b5 may be an integer selected from 0 to 8, but embodiments are not limited thereto.

In one or more embodiments, L₁in Formula 1 may be selected from ligands represented by Formulae 2A(1) and 2A(40):

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In Formulae 2A(1) to 2A(40), R₁to R₃, Y₁to Y₈, and R₁₁are the same as described above, R_11aand R_11bare the same as described above in connection with R₁₁, and * and *′ each indicate a binding site to M in Formula 1, wherein R₁₁, R_11a, and R_11bmay not be hydrogen.

In one or more embodiments,

in Formulae 2A(1) to 2A(40), Y₁may be C(R₄₁), Y₂may be C(R₄₁), Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₈), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28), and 2A(31) to 2A(36), Y₁may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₅);

in Formulae 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28), and 2A(31) to 2A(36), Y₁may be C(R₄₁), Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28), and 2A(31) to 2A(36), Y₁may be C(R₄₁), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28), and 2A(31) to 2A(36), Y₁may be N, Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(1) to 2(4), 2A(7) to 2A(12), 2A(15) to 2A(20), 2A(23) to 2A(28), and 2A(31) to 2A(36), Y₁may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37), and 2A(38), Y₃may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be C(R₄₈), Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37), and 2A(38), Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₈), Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37), and 2A(38), Y₃may be C(R₄₃), Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₈);

in Formulae 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37), and 2A(38), Y₃may be N, Y₄may be C(R₄₄), Y₅may be N, Y₆may be C(R₄₆), Y₇may be C(R₄₇), and Y₈may be C(R₄₈); or

in Formulae 2A(5), 2A(6), 2A(13), 2A(14), 2A(21), 2A(22), 2A(29), 2A(30), 2A(37), and 2A(38), Y₃may be N, Y₄may be C(R₄₄), Y₅may be C(R₄₅), Y₆may be N, Y₇may be C(R₄₇), and Y₈may be C(R₄₈), but embodiments are not limited thereto.

In one or more embodiments, in Formulae 2A(1) and 2A(40),

R₁to R₃may each independently be selected from:

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, and —Si(Q₅₁)(Q₅₂)(Q₅₃); and

wherein Q₅₁to Q₅₃may each independently be selected from:

X₁may be selected from O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃),

Y₁to Y₈are the same as described above, and

R₁₁, R_11a, R_11b, R₂₁to R₂₃, and R₄₁to R₄₈may each independently be selected from:

—B(Q₆)(Q₇) and —P(═O)(Q₈)(Q₉),

(provided that R₁₁, R_11a, and R_11bin Formulae 2A(1) to 2A(40) are not hydrogen),

wherein Q₆to Q₉may each independently be selected from:

In one or more embodiments, in Formulae 2A(1) to 2A(40),

R₁to R₃may each independently be selected from:

an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, a naphthyl group, and —Si(Q₅₁)(Q₅₂)(Q₅₃); and

wherein Q₅₁to Q₅₃may each independently be selected from:

X₁may be O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃),

Y₁to Y₈are the same described above,

R₁₁, R_11a, R_11b, and R₄₁to R₄₈may be selected from deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, groups represented by Formulae 9-1 to 9-17, and groups represented by Formulae 10-1 to 10-30,

R₂₁to R₂₃may each independently be selected from:

but embodiments are not limited thereto.

L₂in Formula 1 may be selected from ligands represented by Formulae 3A to 3G:

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wherein, in Formulae 3A to 3G,

Y₁₁to Y₁₀may each independently be carbon (C) or nitrogen (N), Y₁₁and Y₁₂may be linked via a single bond or a double bond, Y₁₃and Y₁₄may be linked via a single bond or a double bond, and Y₁₅and Y₁₀may be linked via a single bond or a double bond,

CY₃to CY₅may each independently be selected from a C₅-C₆₀cyclic group and a C₂-C₆₀heterocyclic group (which may be a monocyclic group or a polycyclic group), and CY₃and CY₄may optionally be additionally linked via an organic linking group,

a1 to a3 may each independently be an integer selected from 1 to 5, A₁may be P or As,

X_11a, X_11b, X_12a, X_12b, X_13a, and X_13bmay each independently be selected from N, O, N(R₃₄), P(R₃₅)(R₃₆), and As(R₃₇)(R₃₈) (provided that X_12a, X_12b, X_13a, and X_13bare neither N nor O);

R_33″ and R_34″ may each independently be selected from a single bond, a double bond, a substituted or unsubstituted C₁-C₅alkylene group, a substituted or unsubstituted C₂-C₅alkenylene group, and a substituted or unsubstituted C₆-C₁₀arylene group;

Z₁to Z₃, R₃₁, R_32a, R_32b, R_32c, R_33a, R_33b, R₃₄to R₃₈, R_35a, R_35b, R_35c, and R_35dmay each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₁-C₆₀heteroaryl 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),

* and *′ each indicate a binding site to M in Formula 1, and

at least one substituent selected from a substituent(s) of the substituted C₁-C₅alkylene group, the substituted C₂-C₅alkenylene group, the substituted C₆-C₁₀arylene group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₈₀alkenyl group, the substituted C₂-C₈₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —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 C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

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

wherein Q₁to Q₉, Q₁₁to Q₁₉, to Q₂₉, and to Q₃₉may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 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, CY₃to CY₅in Formulae 3A and 3B may each independently be selected from a benzene group, a naphthalene group, a fluorene group, a spiro-bifluorene group, an indene group, a pyrrole group, a thiophene group, a furan group, an imidazole group, a pyrazole group, a thiazole group, an isothiazole group, an oxazole group, an isoxazole group, a pyridine group, a pyrazine group, a pyrimidine group, a pyridazine group, a quinoline group, an isoquinoline group, a benzoquinoline group, a quinoxaline group, a quinazoline group, a carbazole group, a benzimidazole group, a benzofuran group, a benzothiophene group, an isobenzothiophene group, a benzoxazole group, an isobenzoxazole group, a triazole group, a tetrazole group, an oxadiazole group, a triazine group, a dibenzofuran group, a dibenzothiophene group, and a 5,6,7,8-tetrahydroisoquinoline group, but embodiments are not limited thereto.

In one or more embodiments, L₂in Formula 1 may be selected from ligands represented by Formulae 3-1 to 3-111, but are not limited thereto:

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wherein, in Formulae 3-1 to 3-111,

Z₁, Z₂, Z_1a, Z_1b, Z_2a, Z_2b, Z_2c, R_34a, R_34b, and R_34cmay each independently be selected from:

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

wherein Q₁to Q₉and Q₄₄to Q₄₉may each independently be selected from:

aa2 and ab2 may each independently be 1 or 2,

aa3 and ab3 may each independently be selected from 1, 2, and 3,

aa4 and ab4 may each independently be selected from, 1, 2, 3, and 4, and

* and *′ each indicate a binding site to M in Formula 1.

Z₁, Z₂, Z_1a, Z_1b, Z_2a, Z_2b, Z_2c, R_34a, R_34b, and R_34cin Formulae 3-1 to 3-111 may each independently be selected from:

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

wherein Q₁to Q₉may each independently be selected from:

but embodiments are not limited thereto.

In one or more embodiments, L₂in Formula 1 may be selected from ligands represented by Formulae 3-1 (1) to 3-1 (59) and 3-111:

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In one or more embodiments, in Formulae 3-1(1) to 3-1(59) and 3-111,

Z₁, Z₂, Z_1a, Z_1b, Z_1c, Z_1d, Z_2a, Z_2b, Z_2c, Z_2d, R_34a, R_34b, and R_34cmay each independently be selected from deuterium, —F, a cyano group, a nitro group, —SF₅, —CH₃, —CD₃, —CD₂H, —CDH₂, —CF₃, —CF₂H, —CFH₂, —Si(Q₃)(Q₄)(Q₅), groups represented by Formulae 9-1 to 9-17, and groups represented by Formulae 10-1 to 10-30,

wherein Q₃to Q₅may each independently be selected from:

* and *′ each indicate a binding site to M in Formula 1.

In one or more embodiments, in Formula 1, M may be Ir and n1+n2 may be 3; or M may Pt and n1+n2 may be 2, the organometallic compound represented by Formula 1 may be electrically neutral, L₁in Formula 1 may be selected from ligands represented by Formulae 2A-1 to 2A-16, 2AA-1, 2AA-2, 2AA-3, 2AA-4, and 2AB, but embodiments are not limited thereto.

In one or more embodiments, in Formula 1, M may be Ir and n1+n2 may be 3; or M may be Pt and n1+n2 may be 2, the organometallic compound represented by Formula 1 may be electrically neutral, L₁in Formula 1 may be selected from ligands represented by Formulae 2A-1, 2A-5, 2AA-1, and 2AB, and L₂may be selected from ligands represented by Formulae 3-1 to 3-111 (for example, ligands represented by Formulae 3-1(1) to 3-1 (59) and 3-111), but embodiments are not limited thereto.

In one or more embodiments, in Formula 1, M may be Ir and the sum of n1 and n2 may be 3; or M may be Pt and the sum of n1 and n2 may be 2, the organometallic compound represented by Formula 1 may be electrically neutral, L₁in Formula 1 may be selected from ligands represented by Formulae 2A(1) to 2A(40), and L₂in Formula 1 is selected from ligands represented by Formulae 3-1 to 3-111 (for example, ligands represented by Formulae 3-1(1) to 3-1(59) and 3-111), but embodiments are not limited thereto.

In one or more embodiments, the organometallic compound represented by Formula 1 may be one selected from Compounds 1 to 564, but is not limited thereto.

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L₁in the organometallic compound represented by Formula 1 may be selected from ligands represented by Formula 2A, and b4 in Formula 2A may be one or more. That is, a substituent of a pyridine-based ring in Formula 2A may include at least one —Si(R₁)(R₂)(R₃). Since —Si(R₁)(R₂)(R₃) increases a spin density of a metal M of Formula 1, the organic light-emitting device including the organometallic compound represented by Formula 1, which includes the ligand represented by Formula 2A, may have high efficiency.

X₁in Formula 2A may be selected from O, S, S(═O)₂, N(R₂₁), and Si(R₂₂)(R₂₃). Thus, charge mobility of the organometallic compound including the ligand represented by Formula 2A is improved and energy level adjustment is facilitated, thereby improved the efficiency and lifespan of the organic light-emitting device including the organometallic compound.

For example, the highest occupied molecular orbital (HOMO) energy level, lowest unoccupied molecular orbital (LUMO) energy level, singlet (S₁) energy level, and triplet (T₁) energy level of Compounds 1, 2, 8, 22, 139, 146, 304, 305, 321, 323, 327, and 419 were evaluated by a density functional theory (DFT) method of a Gaussian program (the structure was optimized at B3LYP, 6-31G(d,p) level). Results thereof are shown in Table 1.

TABLE 1

S₁energy
T₁energy

Compound No.
HOMO (eV)
LUMO (eV)
level (eV)
level (eV)

Compound 1
−4.842
−1.262
2.887
2.616

Compound 2
−4.874
−1.309
2.869
2.591

Compound 8
−4.812
−1.249
2.875
2.608

Compound 22
−4.812
−1.250
2.889
2.633

Compound 139
−4.827
−1.283
2.867
2.589

Compound 146
−4.829
−1.261
2.872
2.510

Compound 304
−4.781
−1.267
2.837
2.586

Compound 305
−4.773
−1.244
2.852
2.600

Compound 321
−4.856
−1.369
2.803
2.555

Compound 323
−4.820
−1.281
2.849
2.591

Compound 327
−4.863
−1.304
2.887
2.614

Compound 419
−4.756
−1.331
2.753
2.525

Compound 1

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Compound 2

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Compound 8

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Compound 22

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Compound 139

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Compound 146

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Compound 304

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Compound 305

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Compound 321

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Compound 323

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Compound 327

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Compound 419

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First, Second, and Fourth Compounds Respectively Represented by Formulae 51, 61, and 91

Ring A₆₁in Formula 61 may be represented by Formula 61A, and ring A₆₂in Formula 61 may be represented by Formula 61B.

In Formula 61, ring A₆₁may be represented by Formula 61A, and ring A₆₂may be represented by Formula 61B. Ring A₆₁may be condensed with a neighboring 5-membered ring and ring A₆₂, while sharing carbon therewith, and ring A₆₂may be condensed with ring A₆₁and a neighboring 6-membered ring, while sharing carbon therewith.

X₆₁in Formula 61B may be N-[(L₆₂)_a62-(R₆₂)_b62], S, O, S(═O), S(═O)₂, C(═O), C(R₆₃)(R₆₄), Si(R₆₃)(R₆₄), P(R₆₃), P(═O)(R₆₃), or C═N(R₆₃).

In Formula 61, X₇₁may be C(R₇₁) or N, X₇₂may be C(R₇₂) or N, X₇₃may be C(R₇₃) or N, X₇₄may be C(R₇₄) or N, X₇₅may be C(R₇₅) or N, X₇₆may be C(R₇₆) or N, X₇₇may be C(R₇₇) or N, and X₇₈may be C(R₇₈) or N.

In one or more embodiments, in Formula 61, X₇₁may be C(R₇₁), X₇₂may be C(R₇₂), X₇₃may be C(R₇₃), X₇₄may be C(R₇₄), X₇₅may be C(R₇₅), X₇₆may be C(R₇₆), X₇₇may be C(R₇₇), and X₇₃may be C(R₇₃).

L₅₁to L₅₃, L₆₁, L₆₂, and L₉₁to L₉₅in Formulae 51, 61, 61B, and 91 may each independently be selected from a single bond, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀heteroarylene group, a substituted or unsubstituted divalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted divalent non-aromatic condensed heteropolycyclic group.

In one or more embodiments, L₅₁to L₅₃, L₆₁, L₆₂, and to L₉₅in Formulae 51, 61, 61B, and 91 may each independently be selected from:

a single bond, a cyclopentylene group, a cyclohexylene group, a cyclopentenylene group, a cyclohexenylene group, a cycloheptenylene group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a benzoindenylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a benzimidazolylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, an imidazopyrimidinylene group, an imidazopyridinylene group, a pyrrolylene group, a furanylene group, a thiophenylene group, a silolylene group, an isoindolylene group, an indolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, a benzonaphthofuranylene group, a benzonaphthothiophenylene group, a benzonaphthosilolylene group, a pyridoindolylene group, a benzofuropyridinylene group, a benzothienopyridinylene group, a pyrimidoindolylene group, a benzofuropyrimidinylene group, a benzothienopyrimidinylene group, a phenoxazinylene group, a pyridobenzooxazinylene group, and a pyridobenzothiazinylene group; and

a cyclopentylene group, a cyclohexylene group, a cyclopentenylene group, a cyclohexenylene group, a cycloheptenylene group, a phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an indacenylene group, an acenaphthylene group, a benzoindenylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, a pentaphenylene group, a hexacenylene group, an imidazolylene group, a pyrazolylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, an indazolylene group, a purinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a cinnolinylene group, a phenanthridinylene group, an acridinylene group, a phenanthrolinylene group, a phenazinylene group, a benzoxazolylene group, a benzimidazolylene group, a thiazolylene group, an isothiazolylene group, a benzothiazolylene group, an isoxazolylene group, an oxazolylene group, a triazolylene group, a tetrazolylene group, an oxadiazolylene group, an imidazopyrimidinylene group, an imidazopyridinylene group, a pyrrolylene group, a furanylene group, a thiophenylene group, a silolylene group, an isoindolylene group, an indolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, a benzonaphthofuranylene group, a benzonaphthothiophenylene group, a benzonaphthosilolylene group, a pyridoindolylene group, a benzofuropyridinylene group, a benzothienopyridinylene group, a pyrimidoindolylene group, a benzofuropyrimidinylene group, a benzothienopyrimidinylene group, a phenoxazinylene group, a pyridobenzooxazinylene group, and a pyridobenzothiazinylene 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, C₁-C₂₀alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

wherein Q₃₃to Q₃₅may each independently be selected from a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, a pyridinyl group, and a phenylpyridinyl group.

In one or more embodiments, L₅₁to L₅₃, L₆₁, L₆₂, and L₉₁to L₉₅in Formulae 51, 61, 61B, and 91 may each independently be selected from a single bond and groups represented by Formulae 4-1 to 4-36, but embodiments are not limited thereto:

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wherein, in Formulae 4-1 to 4-36,

Y₂₁may be O, S, N(Z₂₃), C(Z₂₃)(Z₂₄), or Si(Z₂₃)(Z₂₄),

Z₂₁to Z₂₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

d2 may be an integer selected from 0 to 2,

d3 may be an integer selected from 0 to 3,

d4 may be an integer selected from 0 to 4,

d5 may be an integer selected from 0 to 5,

d6 may be an integer selected from 0 to 6,

d8 may be an integer selected from 0 to 8, and

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

a51 to a53, a61, a62, and a91 to a95 in Formulae 51, 61, 61B, and 91 respectively indicate the number of groups L₅₁to L₅₃, L₆₁, L₆₂, and L₉₁to L₉₅, and may each independently be an integer selected from 1 to 5.

In one or more embodiments, a51 to a53, a61, a62, and a91 to a95 in Formulae 51, 61, 61B, and 91 may each independently be 1, 2, or 3, or may each independently be 1 or 2, but embodiments are not limited thereto.

When a51 in Formula 51 is two or more, two or more groups L₅₁may be identical to or different from each other. a52 to a53, a61, a62 and a91 to a95 are the same as described above in connection with a51.

R₅₁to R₅₃, R₆₁to R₆₄, R₇₁to R₇₉, and R₉₁to R₉₅in Formulae 51, 61, 61A, 61B, and 91 may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), and —B(Q₁₆)(Q₁₇).

In one or more embodiments, L₅₁to L₅₃, L₆₁, L₆₂, and to L₉₅in Formulae 51, 61, 61B, and 91 may each independently be selected from:

a single bond, a phenylene group, a naphthylene group, a benzoindenylene group, a fluorenylene group, a spiro-bifluorenylene group, a benzofluorenylene group, a dibenzofluorenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthrenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylene group, a pyridinylene group, a pyrazinylene group, a pyrimidinylene group, a pyridazinylene group, a triazinylene group, a quinolinylene group, an isoquinolinylene group, a benzoquinolinylene group, a phthalazinylene group, a naphthyridinylene group, a quinoxalinylene group, a quinazolinylene group, a phenanthridinylene group, a phenanthrolinylene group, an imidazopyrimidinylene group, an imidazopyridinylene group, a pyrrolylene group, a furanylene group, a thiophenylene group, a silolylene group, an isoindolylene group, an indolylene group, a benzofuranylene group, a benzothiophenylene group, a benzosilolylene group, a carbazolylene group, a dibenzofuranylene group, a dibenzothiophenylene group, a dibenzosilolylene group, a benzocarbazolylene group, a benzonaphthofuranylene group, a benzonaphthothiophenylene group, and a benzonaphthosilolylene 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 C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

but embodiments are not limited thereto.

R₅₁to R₅₃, R₆₁to R₆₄, R₇₁to R₇₉, and R₉₁to R₉₅in Formulae 51, 61, 61A, 61B, and 91 may each independently be selected from:

a C₁-C₂₀alkyl group and a C₁-C₂₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an 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 cyclopentyl group, a cyclohexyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a phenyl group, a pentalenyl group, an indenyl group, a naphthyl group, an azulenyl group, a heptalenyl group, an indacenyl group, an acenaphthyl group, a benzoindenyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group, a perylenyl group, a pentaphenyl group, a hexacenyl group, an imidazolyl group, a pyrazolyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, an indazolyl group, a purinyl group, a quinolinyl group, an isoquinolinyl group, a benzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, a quinoxalinyl group, a quinazolinyl group, a cinnolinyl group, a phenanthridinyl group, an acridinyl group, a phenanthrolinyl group, a phenazinyl group, a benzoxazolyl group, a benzimidazolyl group, a thiazolyl group, an isothiazolyl group, a benzothiazolyl group, an isoxazolyl group, an oxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, an imidazopyrimidinyl group, an imidazopyridinyl group, a pyrrolyl group, a furanyl group, a thiophenyl group, a silolyl group, an isoindolyl group, an indolyl group, a benzofuranyl group, a benzothiophenyl group, a benzosilolyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a dibenzosilolyl group, a benzocarbazolyl group, a benzonaphthofuranyl group, a benzonaphthothiophenyl group, a benzonaphthosilolyl group, a pyridoindolyl group, a benzofuropyridinyl group, a benzothienopyridinyl group, a pyrimidoindolyl group, a benzofuropyrimidinyl group, a benzothienopyrimidinyl group, a phenoxazinyl group, a pyridobenzooxazinyl group and a pyridobenzothiazinyl 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 C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅); and

—Si(Q₁₃)(Q₁₄)(Q₁₅),

wherein Q₁₃to Q₁₅and Q₃₃to Q₃₅may each independently be selected from a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, a pyridinyl group, and a phenylpyridinyl group.

In one or more embodiments, R₅₁to R₅₃, R₆₁to R₆₄, R₇₁to R₇₉, and R₉₁to R₉₅in Formulae 51, 61, 61A, 61B, and 91 may each independently be selected from groups represented by Formulae 5-1 to 5-15, 6-1 to 6-6, and 7-1 to 7-50, but embodiments are not limited thereto:

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wherein, in Formulae 5-1 to 5-15, 6-1 to 6-6, and 7-1 to 7-50,

Y₃₁may be O, S, N(Z₃₃), C(Z₃₃)(Z₃₄), or Si(Z₃₃)(Z₃₄),

Z₃₁to Z₃₄may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

e2 may be an integer selected from 0 to 2,

e3 may be an integer selected from 0 to 3,

e4 may be an integer selected from 0 to 4,

e5 may be an integer selected from 0 to 5,

e6 may be an integer selected from 0 to 6,

e7 may be an integer selected from 0 to 7,

e9 may be an integer selected from 0 to 9, and

* indicates a binding site to a neighboring atom.

b61, b62, and b79 in Formulae 61A and 61B respectively indicate the number of groups R₆₁, R₆₂, and R₇₉, and may each independently be an integer selected from 0 to 3. In one or more embodiments, b61 and b62 may be 1 or 2, but embodiments are not limited thereto.

In one or more embodiments, in Formula 51,

L₅₁to L₅₃may each independently be selected from a single bond and groups represented by Formulae 4-1 to 4-18,

a51 to a53 may each independently be 1 or 2,

R₅₁to R₅₃may each independently be selected from:

groups represented by Formulae 5-1 to 5-15 and 6-1 to 6-6, and

at least one selected from R₅₁to R₅₃may be selected from groups represented by Formulae 6-1 to 6-6.

In one or more embodiments, X₆₁in Formula 61 may be N-[(L₆₂)_a62-(R₆₂)_b62].

In one or more embodiments, in Formula 61,

X₆₁may be N-[(L₆₂)_a62-(R₆₂)_b62],

at least one selected from L₆₁and L₆₂may be selected from groups represented by Formulae 4-19 to 4-36,

a61 and a62 may each independently be 1 or 2,

at least one selected from R₆₁and R₆₂may be selected from groups represented by Formulae 7-1 to 7-50,

b61 and b62 may be 1, but embodiments are not limited thereto.

In one or more embodiments, in Formula 61,

X₆₁may be N-[(L₆₂)_a62-(R₆₂)_b62],

at least one selected from R₆₁and R₆₂may be selected from groups represented by Formulae 6-1 to 6-6, and

b61 and b62 may be 1, but embodiments are not limited thereto.

At least one selected from to L₉₅and R₉₁to R₉₅in Formula 91 may include a carbazole ring or a triphenylene ring. That is, the fourth compound represented by Formula 91 essentially includes at least one carbazole ring and at least one triphenylene ring.

In one or more embodiments,

the first compound may be represented by one selected from Formulae 51-1 to 51-3,

the second compound may be represented by one selected from Formulae 61-1 to 61-6,

the fourth compound may be represented by one selected from Formulae 91-1 to 91-14, but embodiments are not limited thereto:

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wherein L₅₁, L₅₃, a51, a53, R₅₁, and R₅₃in Formulae 51-1 to 51-3 are the same as described above,

X₆₁, L₆₁, a61, R₆₁, b61, R₇₁to R₇₉, and b79 in Formulae 61-1 to 61-6 are the same as described above,

in Formulae 91-1 to 91-14,

L₉₁, a91, and R₉₁to R₉₅are the same as described above,

L₉₆is the same as described above in connection with L₉₁,

a96 may be 1 or 2,

Z₃₁to Z₃₃may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₂-C₂₀alkenyl group, a C₂-C₂₀alkynyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, a pyridinylphenyl group, a naphthyl group, an anthracenyl group, a pyrenyl group, a phenanthrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, a phenylpyridinyl group, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinyl group, an isoquinolinyl group, a phthalazinyl group, a quinoxalinyl group, a cinnolinyl group, a quinazolinyl group, a carbazolyl group, a dibenzofuranyl group, a dibenzothiophenyl group, and —Si(Q₃₃)(Q₃₄)(Q₃₅),

e3 may be an integer selected from 0 to 3, and

e4 may be an integer selected from 0 to 4.

Third Compound Represented by Formula 81

In Formula 81, Z₁₁may be N or C(R_a), Z₁₂may be N or C(R_b), Z₁₁may be N or C(R_c), Z₁₄may be N or C(R_d), Z₁₅may be N or C(R_e), Z₁₀may be N or C(R_f), Z₁₇may be N or C(R_g), Z₁₈may be N or C(R_h), Z₁₉may be N or C(R_i), and at least one selected from Z₁₁to Z₁₉may be N.

Accordingly, since the third compound easily accepts electrons when an electric field is applied thereto, an organic light-emitting device including the third compound may have a low driving voltage. Since the third compound also includes a triphenylene core, the third compound may have a bipolar structure. Therefore, in the organic light-emitting device including the third compound represented by Formula 81, a flow of hole and electron may be balanced. Thus, the organic light-emitting device including the third compound may have high efficiency.

In one or more embodiments, R₈₁to R₉₀and R_ato R_iin Formula 81 may each independently be selected from hydrogen, deuterium, a C₁-C₁₀alkyl group, and groups represented by Formulae 5-1 to 5-15, but embodiments are not limited thereto.

The number of 6-membered rings substituted with a triphenylene core in Formula 81 may be six or less,

L₈₁in Formula 81 may be selected from a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, and a substituted or unsubstituted terphenylene group,

a81 to a83 in Formula 81 may each independently be 0 or 1, and

in Formula 81, a81+a82+a83≥1.

The 6-membered rings substituted with the triphenylene core in Formula 81 may refer to all 6-membered rings directly or indirectly linked to the triphenylene core and may include a 6-membered ring including a carbon atom, a nitrogen atom, or any combinations thereof.

The third compound may be represented by Formula 81-1 or 81-2:

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wherein various substituents in Formulae 81-1 and 81-2 are the same as described above.

The third compound represented by Formula 81 may have at least one kink structure.

The kink structure refers to a structure in which two linking portions that link three rings to one another do not form a linear structure with each other. For example, in the case of a phenylene group, an o-phenylene group and an m-phenylene group, in which linking portions do not form a linear structure, have the kink structure. A p-phenylene group, in which the linking portions form a linear structure, does not have a kink structure.

The kink structure in Formula 81 may be formed around a linking group (L₈₁) and/or arylene group/heteroarylene group.

In one or more embodiments, when a81 of Formula 81 is zero, that is, when *-(L₈₁)_a81-*′ is a single bond, the kink structure may be formed around an arylene group/heteroarylene group.

In one or more embodiments, when a81 of Formula 81A is 1, the kink structure may be formed around a linking group (L₈₁) in Formula 81. In one or more embodiments, L₈₁in Formula 81 may be a substituted or unsubstituted phenylene group having a kink structure, a substituted or unsubstituted biphenylene group having a kink structure, or a substituted or unsubstituted terphenylene group having a kink structure. In one or more embodiments, L₈₁in Formula 81 may be selected from groups represented by Formulae 8-1 to 8-36:

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wherein Z₄₁to Z₄₃in Formulae 8-1 to 8-36 are the same as described above in connection with R₈₁in Formula 81, and * and *′ each indicate a binding site to a neighboring atom.

Formula 81 may have at least two kink structures. In one or more embodiments, Formula 81 may have at least two to four kink structures.

Since the third compound represented by Formula 81 has the kink structure as described above, it is possible to appropriately localize charges and effectively control a flow of a conjugated system. Thus, an organic light-emitting device including the third compound represented by Formula 81 may have a long lifespan.

Also, in the third compound represented by Formula 81, stacking between molecules may be effectively prevented. Accordingly, in the case of forming a film by using the third compound represented by Formula 81, it is possible to improve process stability and reduce a deposition temperature. The stacking prevention effect may be further improved when a81 of Formula 81 is 1.

Specific Examples of First to Fourth Compounds

The first compound may be selected from Compounds A1 to A18,

the second compound may be selected from Compounds B1 to B30,

the third compound may be selected from Compounds A-1 to A-125,

the fourth compound may be selected from Compounds B-10 to B-161, C-10 to C-33, and D-10 to D-29, but embodiments are not limited thereto:

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Synthesis methods of the organometallic compound represented by Formula 1 and the first to fourth compounds may be recognized by those of ordinary skill in the art by referring to Synthesis Examples to be described below.

Organic Light-Emitting Device

The organometallic compound represented by Formula 1 may be 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, and at least one selected from the first to fourth compounds may be used as a host.

Therefore, in one or more embodiments, the emission layer of the organic light-emitting device may include a dopant and a host, the dopant may include one or more of organometallic compounds represented by Formula 1, and the host may include at least one selected from the first to fourth compounds.

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

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

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

In one or more embodiments, the first electrode may be an anode, the second electrode may be a cathode, the organic layer may 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, the hole transport region may include at least one layer selected from a hole injection layer, a hole transport layer, and an electron blocking layer, and the electron transport region may include at least one layer selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

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

FIG. 1 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 FIG. 1. 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 at least one selected from a hole injection layer, a hole transport layer, an electron blocking layer, and a buffer layer.

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 material 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 to about 500° C., a vacuum pressure of about 10′⁸to about 10′³torr, and a deposition rate of about 0.01 to about 100 Angstroms per second (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, (3-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:

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Ar₁₀₁and Ar₁₀₂in Formula 201 may 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, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀alkoxy group, a C₃-C₁₀cycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀heterocycloalkyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group.

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

R₁₀₁to R₁₀₈, R₁₁₁to R₁₁₉, and R₁₂₁to R₁₂₄in Formulae 201 and 202 may each independently be selected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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, etc.), and a C₁-C₁₀alkoxy group (for example, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, etc.);

a C₁-C₁₀alkyl group and a C₁-C₁₀alkoxy 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, 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.

R₁₀₉in Formula 201 may 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, —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, an anthracenyl group, and a pyridinyl group.

According to an embodiment, the compound represented by Formula 201 may be represented by Formula 201A, but is not limited thereto:

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R₁₀₁, R₁₁₁, R₁₁₂, and R₁₀₉in Formula 201A may 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 illustrated 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 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 below, but are not limited thereto.

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The hole transport region may include a buffer layer.

Also, 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 (EML) 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 to form the hole injection layer although the deposition or coating conditions may vary according to the 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 first through fourth compounds. 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, the dopant may include the organometallic compound represented by Formula 1, and the host may include at least one selected from the first compound to the fourth compound.

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 stack 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 to about 15 parts by weight based on 100 parts by weight of the host, but is not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. 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 at least one selected from a hole blocking layer, an electron transport layer, and an electron injection layer.

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 is 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 a compound represented by Formula 440 or Formula 441:

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L₄₁and L₄₂in Formulae 440 and 441 may each independently be selected from:

a C₆-C₆₀arylene group, a C₂-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group; and

a C₆-C₆₀arylene group, a C₂-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group and a triazinyl group,

a41 and a42 in Formulae 440 and 441 may each independently be an integer selected from 0 to 5,

Ar₄₁and Ar₄₂in Formulae 440 and 441 may each independently be selected from:

a C₆-C₆₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

a C₆-C₆₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, a C₁-C₂₀alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a naphthyl group, a fluorenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group,

R₄₁and R₄₂in Formulae 440 and 441 may each independently be selected from:

a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, benzopyrimidinyl group, an imidazopyridinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, and a phenanthrenyl 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 benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, benzopyrimidinyl group, an imidazopyridinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, and a phenanthrenyl group.

L₄₁and L₄₂in Formulae 440 and 441 may be the same as described in connection with L₂.

In one or more embodiments, the electron transport layer may include a compound represented by Formula 442:

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In Formula 42, T₁may be N or C(R₂₀₁), T₂may be N or C(R₂₀₂), T₃may be N or C(R₂₀₃), and at least one selected from T₁to T₃may be N,

R₂₀₁to R₂₀₃in Formulae 440 and 441 may each independently selected from:

hydrogen, 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 C₆-C₆₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

Ar₂₀₁to Ar₂₀₃in Formulae 440 and 441 may each independently be selected from:

a C₆-C₆₀arylene group, a C₂-C₆₀heteroarylene group, a divalent non-aromatic condensed polycyclic group, and a divalent non-aromatic condensed heteropolycyclic group; and

p, q, and r in Formulae 440 and 441 may each independently be 0, 1, or 2; and

Ar₂₁₁and Ar₂₁₃in Formulae 440 and 441 may each independently be selected from:

a C₆-C₆₀aryl group, a C₂-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic condensed heteropolycyclic group; and

In an embodiment, at least two selected from T₁to T₃in Formula 442 may be N.

In one or more embodiments, T₁to T3 in Formula 442 may all be N.

Ar₂₀₁to Ar₂₀₃in Formula 442 may each independently be selected from:

a phenylene group, a naphthylene group, anthrylene group, a pyrenylene group, a fluorenylene group, a triphenylenyl group, a pyridinylene group and a pyrimidinylene group; and

a phenylene group, a naphthylene group, anthrylene group, a pyrenylene group, a fluorenylene group, a triphenylenyl group, a pyridinylene group, and a pyrimidinylene group, each substituted with at least one selected from a phenyl group, a naphthyl group, an anthryl group, a pyrenyl group, a fluorenyl group, a triphenylenyl group, a pyridinyl group, and a pyrimidinyl group, but embodiments of the present disclosure are not limited thereto.

p, q, and r in Formula 442 may each independently be 0, 1, or 2. In an embodiment, p, q, and r in Formula 442 may each independently be 0 or 1, but embodiments of the present disclosure are not limited thereto.

Ar₂₁₁to Ar₂₁₃in Formula 442 may each independently be selected from:

a phenyl group, a naphthyl group, a pyrenyl group, a chrysenyl group, a fluorenyl group, a phenanthrenyl group, a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, benzopyrimidinyl group, an imidazopyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazinyl 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 fluorenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto.

In an embodiment, at least one selected from Ar₂₁₁to Ar₂₁₃in Formula 442 may each independently be selected from:

a benzimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, benzopyrimidinyl group, an imidazopyrimidinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a pyridinyl group, a pyrimidinyl group, a pyrazinyl group, and a triazinyl 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 fluorenyl group, a pyrenyl group, a chrysenyl group, a phenanthrenyl group, a pyridinyl group, a pyrimidinyl group, and a triazinyl group, but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, at least one selected from Ar₂₁₁to Ar₂₁₃in Formula 442 may be a substituted or unsubstituted phenanthrenyl group.

For example, the electron transport region may include at least one selected from Compounds ET1 to ET16, but embodiments of the present disclosure are not limited thereto:

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In an embodiment, the electron transport region may include an electron transport layer, and the electron transport layer may include a compound represented by at least one selected from Formulae 440, 441, and 442, but embodiments of the present disclosure are not limited thereto.

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 quinolate, LiQ) or ET-D2.

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The electron transport region may include an electron injection layer (EIL) 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, Li₂O, BaO, and LiQ.

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 FIG. 1, but is not limited thereto.

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. Non-limiting examples thereof include a methyl group, an ethyl group, a propyl group, an iso-butyl 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-C₆₀alkoxy group” as used herein refers to a monovalent group represented by —OA₁₀₁(wherein A₁₀₁is the C₁-C₆₀alkyl group). Non-limiting examples thereof include a methoxy group, an ethoxy group, and an iso-propyloxy (iso-propoxy) group.

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

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

The term “C₃-C₁₀cycloalkyl group” as used herein refers to a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms. 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. 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, and which is not aromatic. 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.

A C₆-C₆₀aryl group as used herein refers to a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, and a C₆-C₆₀arylene group 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 a heterocyclic 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 a heterocyclic 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), and a C₆-C₆₀arylthio group as used herein indicates —SA₁₀₃(wherein A₁₀₃is the C₆-C₆₀aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as used herein refers to a monovalent group (for example, having 8 to 60 carbon atoms) that has two or more rings condensed to each other, only carbon atoms as a ring-forming atom, and which is non-aromatic in the 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) that has two or more rings condensed to each other, has a heteroatom selected from N, O, P, and S, other than carbon atoms, as a ring-forming atom, and which is non-aromatic in the 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.

In the present specification, at least one substituent selected from a substituent(s) of the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀alkenyl group, the substituted C₂-C₆₀alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀cycloalkenyl group, the substituted C₁-C₁₀heterocycloalkenyl group, the substituted C₆-C₆₀aryl group, the substituted C₆-C₆₀aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be selected from:

a C₁-C₆₀alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀alkynyl group, and a C₁-C₆₀alkoxy group, each substituted with at least one selected from deuterium, —F, —Cl, —Br, —I, —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 C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, —N(Q₁₁)(Q₁₂), —Si(Q₁₃)(Q₁₄)(Q₁₅), —B(Q₁₆)(Q₁₇), and —P(═O)(Q₁₈)(Q₁₉);

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

wherein Q₁to Q₉, Q₁₁to Q₁₉, to Q₂₉, and Q₃₁to Q₃₉may each independently be selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a 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 C₁-C₆₀heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, and a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

When a group containing a specified number of carbon atoms is substituted with any of the groups listed in the preceding paragraphs, 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-C₆₀alkyl” refers to a C₁-C₆₀alkyl group substituted with C₆-C₆₀aryl group, the total number of carbon atoms in the resulting aryl substituted alkyl group is C₇-C₁₂₀.

Hereinafter, a compound and an organic light-emitting device according to embodiments are described in detail with reference to Synthesis Example 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 an amount of A used was identical to an amount of B used, in terms of a molar equivalent.

EXAMPLES
Synthesis Example 1: Synthesis of Compound 1

Synthesis of Compound A1

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9 grams (g) (39.09 millimoles, mmol) of 2-bromo-5-(trimethylsilyl)pyridine, 13.22 g (44.96 mmol) of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 2.26 g (1.95 mmol) of Pd(PPh₃)₄, and 16.21 g (117.27 mmol) of K₂CO₃were mixed with 210 milliliters (mL) of tetrahydrofuran (THF) and 70 mL of distilled water. The mixture was agitated under reflux for 18 hours. The temperature was reduced to room temperature, the organic layer was extracted by using methylene chloride (MC), anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration, and the dried solution was filtered. The obtained filtrate was concentrated under reduced pressure and the obtained residual was purified by column chromatography (MC:Hexane=1:1) to obtain 7.4 g (60%) of Compound A1.

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14.66 g (94.44 mmol) of 2-phenylpyridine and 14.80 g (41.97 mmol) of iridium chloride were mixed with 210 mL of ethoxyethanol and 70 mL of distilled water, and the mixture was agitated under reflux for 24 hours to carry out the reaction. Then, the temperature was reduced to room temperature. The generated solid was filtered, separated, and thoroughly washed with water, methanol, and hexane in that order. The obtained solid was dried in a vacuum oven to obtain 19.5 g (87%) of Compound M2A.

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6.01 g (5.60 mmol) of Compound M2A was mixed with 45 mL of MC, 2.88 g (11.21 mmol) of AgOTf was dissolved in 15 mL of methanol and added thereto. The mixture was agitated for 18 hours at room temperature while blocking light with an aluminum foil to carry out the reaction. A solid (Compound M1A) obtained by removing a solid generated by celite filtration and decompressing a filtrate was used in the next reaction, without performing an additional purification thereon.

Synthesis of Compound 1

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8 g (11.22 mmol) of Compound M1A and 4.28 g (13.47 mmol) of Compound A1 were mixed with 100 mL of ethanol, and the resultant was agitated under reflux for 18 hours to carry out the reaction. Then, the temperature was reduced to room temperature. The resulting mixture was filtered to separate a solid, which was then thoroughly washed with ethanol and hexane. Column chromatography was then performed thereon using MC and hexane at a ratio of 40:60 to obtain 2.54 g (28%) of Compound 1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₂H₃₄IrN₃OSi: m/z 817.2100, Found: 817.2104

Synthesis Example 2: Synthesis of Compound 3

Synthesis of Compound B1

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8.5 g (55%) of Compound B1 was obtained in the same manner as Compound A1 in Synthesis Example 1, except that 13.47 g (46.92 mmol) of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole were used instead of 13.22 g (44.96 mmol) of 2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

Synthesis of Compound 3

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2.4 g (32%) of Compound 3 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.42 mmol) of Compound M1A and 3.97 g (10.10 mmol) of Compound B1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.28 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₈H₃₉IrN₄Si: m/z 892.2573, Found: 892.2575

Synthesis Example 3: Synthesis of Compound 8

Synthesis of Compound C3

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18.55 g (73.92 mmol) of 2,5-dibromo-4-methylpyridine, 18.81 g (88.70 mmol) of dibenzo[b,d]furan-2-ylboronic acid, 1.66 g (7.39 mmol) of Pd(OAc)₂, 3.88 g (14.78 mmol) of PPh₃, and 20.43 g (147.84 mmol) of K₂CO₃were mixed with 200 mL of acetonitrile and 100 mL of methanol. The mixture was agitated at a temperature of 50° C. for 18 hours, and the resultant was cooled to room temperature and filtered. The organic layer was extracted therefrom by using MC, anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration, and the dried resulting solution was filtered. A filtrate was concentrated under reduced pressure and the obtained residual was purified by column chromatography (MC:Hx=60:40) to obtain 13.0 g (52%) of Compound C3.

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12.24 g (36.20 mmol) of Compound C3 was mixed with THF 300 mL, and the mixture was cooled to −78° C. 33.94 mL (54.30 mmol) of 1.6 molar (M) n-BuLi was slowly added thereto and was agitated at −78° C. for 1 hour. Then, 6.89 mL (54.30 mmol) of TMSCl was added thereto, and a reaction was carried out at −78° C. for 1 hour. The temperature was then raised to room temperature and the reaction was further carried out for 12 hours. The organic layer obtained therefrom was extracted by using MC, and anhydrous magnesium sulfate was added thereto to remove water therefrom. The obtained filtrate was concentrated under reduced pressure and column chromatography was performed on the obtained residual with EA:Hexane=4:96 to obtain 8.0 g (67%) of Compound C2.

Synthesis of Compound 8

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2.05 g (29%) of Compound 8 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.42 mmol) of Compound M1A and 3.35 g (10.11 mmol) of Compound C2 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₃H₃₆IrN₃OSi: m/z 831.2257, Found: 831.2259

Synthesis Example 4: Synthesis of Compound 22

Synthesis of Compound C1

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7.1 g (21.42 mmol) of Compound C2 was mixed with 100 mL of THF The mixture was cooled to −78° C. and 26.8 mL (53.54 mmol) of lithium diisopropylamide (LDA) was slowly added thereto. The resulting mixture was agitated at −78° C. for 1 hour to perform a reaction. The temperature was raised to room temperature and the reaction was further carried out for 1.5 hours. The temperature was then reduced to −78° C., 5.03 mL (53.54 mmol) of 2-bromopropane was slowly added to the resultant, the temperature was raised to room temperature, and the reaction was carried out for 12 hours. The organic layer obtained therefrom was extracted by using MC, and anhydrous magnesium sulfate was added thereto to remove water. The obtained filtrate was concentrated under reduced pressure and column chromatography was performed on the obtained residual with EA:Hexane=4:96 to obtain 6.80 g (85%) of Compound C1.

Synthesis of Compound 22

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2.30 g (31%) of Compound 22 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.42 mmol) of Compound M1A and 3.77 g (10.10 mmol) of Compound C1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.28 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₆H₄₂IrN₃OSi: m/z 873.2726, Found: 873.2720

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1.3 g (17%) of Compound 32 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.41 mmol) of Compound M1A and 3.92 g (10.09 mmol) of Compound D1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₆H₄₃IrN₄OSi: m/z 888.2835, Found: 888.2830

Synthesis Example 6: Compound 35

Synthesis of Compound E3

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13.7 g (69%) of Compound E3 was obtained in the same manner as Compound C₃in Synthesis Example 3, except that 15.64 g (49.97 mmol) of 2,5-dibromo-4-phenylpyridine and 12.71 g (55.96 mmol) of dibenzo[b,d]furan-2-ylboronic acid were respectively used instead of 18.55 g (73.92 mmol) of 2,5-dibromo-4-methylpyridine and 18.81 g (88.70 mmol) of dibenzo[b,d]furan-2-ylboronic acid.

Synthesis of Compound E2

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6.6 g (66%) of Compound E2 was obtained in the same manner as Compound C₂in Synthesis Example 3, except that 10.17 g (25.41 mmol) of Compound E3 was used instead of 12.24 g (36.20 mmol) of Compound C3.

Synthesis of Compound 35

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1.8 g (24%) of Compound 35 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.41 mmol) of Compound M1A and 3.97 g (10.09 mmol) of Compound E2 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₈H₃₈IrN₃OSi: m/z 893.2413, Found: 893.2417

Synthesis Example 7: Synthesis of Compound 146

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2.1 g (31%) of Compound 146 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (8.41 mmol) of Compound M1A and 3.2 g (10.09 mmol) of Compound F1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₂H₃₄IrN₃OSi: m/z 817.2100, Found: 817.2097

Synthesis Example 8: Synthesis of Compound 300

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17.2 g (86%) of Compound M2B was obtained in the same manner as Compound M2A in Synthesis Example 1, except that 15.05 g (66.14 mmol) of 2-phenyl-5-(trimethylsilyl)pyridine and iridium 4.10 g (11.62 mmol) of chloride were respectively used instead of 14.66 g (94.44 mmol) of 2-phenylpyridine and 14.80 g (41.97 mmol) of iridium chloride.

Synthesis of Compound M1B

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Compound M1B was obtained in the same manner as Compound M1A in Synthesis Example 1, except that 4.76 g (3.5 mmol) of Compound M2B was used instead of 6.01 g (5.60 mmol) of Compound M2A.

Synthesis of Compound 300

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1.3 g (19%) of Compound 300 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (6.99 mmol) of Compound M1B and 2.66 g (8.39 mmol) of Compound A1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₈H₅₀IrN₃OSi₃: m/z 961.2891, Found: 961.2887

Synthesis Example 9: Synthesis of Compound 305

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1.4 g (20%) of Compound 305 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (6.99 mmol) of Compound M1B and 3.14 g (8.39 mmol) of Compound C1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₅₂H₅₈IrN₃OSi₃: m/z 1017.3517, Found: 1017.3512

Synthesis Example 10: Synthesis of Compound 322

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1.1 g (16%) of Compound 322 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (6.99 mmol) of Compound M1B and 2.78 g (8.74 mmol) of Compound G1 were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₄₇H₄₉IrN₄OSi₃: m/z 962.2843, Found: 962.2843

Synthesis Example 11: Synthesis of Compound 327

Synthesis of Compound M2C

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8.3 g (83%) of Compound M2C was obtained in the same manner as Compound M2A in Synthesis Example 1, except that 8.3 g (26.15 mmol) of Compound A1 and 4.10 g (11.62 mmol) of iridium chloride were respectively used instead of 14.66 g (94.44 mmol) of 2-phenylpyridine and 14.80 g (41.97 mmol) of iridium chloride.

Synthesis of Compound M1C

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Compound M1C was obtained in the same manner as Compound M1A in Synthesis Example 1, except that 4.973 g (2.89 mmol) of Compound M2C was used instead of 6.01 g (5.60 mmol) of Compound M2A.

Synthesis of Compound 327

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1.4 g (25%) of Compound 327 was obtained in the same manner as Compound 1 in Synthesis Example 1, except that 6.00 g (5.78 mmol) of Compound M1C and 1.08 g (6.94 mmol) of phenylpyridine were respectively used instead of 8 g (11.22 mmol) of Compound M1A and 4.46 g (13.47 mmol) of Compound A1. The obtained product was confirmed by Mass and HPLC analysis.

HRMS (MALDI) calcd for C₅₁H₄₄IrN₃O₂Si₂: m/z 979.2601, Found: 979.2603

Synthesis Example 12: Synthesis of Compound A-1

Reaction Scheme (131)12

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Under a nitrogen atmosphere, 20 g (56.5 mmol) of Intermediate 1-1 was dissolved in 0.2 liters (L) of tetrahydrofuran (THF), and 15.1 g (56.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.65 g (0.57 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 19.5 g (141 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature 80° C. for 20 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 22.1 g (85%) of Compound A-1.

HRMS (70 eV, EI+): m/z calcd for C₃₃H₂₁N₃: 459.1735, found: 459.

Elemental Analysis: C, 86%; H, 5%

Synthesis Example 13: Synthesis of Compound A-13

Reaction Scheme (131)13

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Under a nitrogen atmosphere, 20 g (46.5 mmol) of Intermediate 1-3 was dissolved in 0.2 L of tetrahydrofuran (THF), and 12.4 g (46.5 mmol) of 4-chloro-2,6-diphenylpyridine and 0.54 g (0.47 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 16.1 g (116 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 17 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 18.9 g (76%) of Compound A-13.

HRMS (70 eV, EI+): m/z calcd for C₄₁H₂₇N: 533.2143, found: 533.

Elemental Analysis: C, 92%; H, 5%

Synthesis Example 14: Synthesis of Compound A-14

Reaction Scheme (131)14

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Under a nitrogen atmosphere, 20 g (46.5 mmol) of Intermediate 1-3 was dissolved in 0.2 L of tetrahydrofuran (THF), and 12.4 g (46.5 mmol) of 2-chloro-4,6-diphenylpyrimidine and 0.54 g (0.47 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. Then, 16.1 g (116 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 15 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 20.4 g (82%) of Compound A-14.

HRMS (70 eV, EI+): m/z calcd for C₄₀H₂₆N₂: 534.2096, found: 534.

Elemental Analysis: C, 90%; H, 5%

Synthesis Example 15: Compound A-15

Reaction Scheme (131)15

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Under a nitrogen atmosphere, 20 g (46.5 mmol) of Intermediate 1-3 was dissolved in 0.2 L tetrahydrofuran (THF), and 12.4 g (46.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.54 g (0.47 mmol) of triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 16.1 g (116 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 20 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). The anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 21.2 g (85%) of Compound A-15.

HRMS (70 eV, EI+): m/z calcd for C₃₉H₂₅N₃: 535.2048, found: 535.

Elemental Analysis: C, 87%; H, 5%

Synthesis Example 16: Synthesis of Compound A-24

Reaction Scheme (131)16

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Under a nitrogen atmosphere, 20 g (46.5 mmol) of Intermediate 1-5 was dissolved in 0.2 L of tetrahydrofuran (THF), and 12.4 g (46.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.54 g (0.47 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 16.1 g (116 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 27 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 19.7 g (79%) of Compound A-24.

HRMS (70 eV, EI+): m/z calcd for C₃₉H₂₅N₃: 535.2048, found: 535.

Elemental Analysis: C, 87%; H, 5%

Synthesis Example 17: Synthesis of Compound A-33

Reaction Scheme (131)17

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Under a nitrogen atmosphere, 20 g (39.5 mmol) of Intermediate 1-7 was dissolved in 0.2 L of tetrahydrofuran (THF), and 10.6 g (39.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 13.6 g (98.8 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 23 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 17.9 g (74%) of Compound A-33.

HRMS (70 eV, EI+): m/z calcd for C₄₅H₂₉N₃: 611.2361, found: 611.

Elemental Analysis: C, 88%; H, 5%

Synthesis Example 18: Synthesis of Compound A-69

Reaction Scheme (131)18

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Under a nitrogen atmosphere, 20 g (39.5 mmol) of Intermediate 1-9 was dissolved in 0.2 L of tetrahydrofuran (THF), 10.6 g (39.5 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 13.6 g (98.8 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 32 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 15.2 g (63%) of Compound A-69.

HRMS (70 eV, EI+): m/z calcd for C₄₅H₂₉N₃: 611.2361, found: 611.

Elemental Analysis: C, 88%; H, 5%

Synthesis Example 19: Synthesis of Compound A-87

Reaction Scheme (131)19

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Under a nitrogen atmosphere, 20 g (34.3 mmol) of Intermediate 1-11 was dissolved in 0.2 L of tetrahydrofuran (THF), 9.19 g (34.3 mmol) of 2-chloro-4,6-diphenyl-1,3,5-triazine and 0.4 g (0.34 mmol) of tetrakis(triphenylphosphine)palladium were added thereto and the reaction mixture was agitated. 11.9 g (85.8 mmol) of potassium carbonate saturated in water was added thereto, and the resultant was heated at a temperature of 80° C. for 29 hours under reflux. After the reaction was completed, water was added to the reaction solution and the mixture was extracted by using dichloromethane (DCM). Then, an anhydrous magnesium sulfate (MgSO₄) was added thereto to perform dehydration. The resultant was filtered and concentrated under reduced pressure. The obtained residual was separated and purified by flash column chromatography to obtain 16.3 g (69%) of Compound A-87.

HRMS (70 eV, EI+): m/z calcd for C₅₁H₃₃N₃: 687.2674, found: 687.

Elemental Analysis: C, 89%; H, 5%

Synthesis Example 20: Synthesis of Compound C-10

Reaction Scheme (131)20

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10 g (34.83 mmol) of phenylcarbazolyl boronic acid, 11.77 g (38.31 mmol) of Intermediate 141-2, 14.44 g (104.49 mmol) of potassium carbonate, 0.80 g (0.7 mmol) of tetrakis-(triphenylphosphine)palladium (0) were suspended in 140 ml of toluene and 50 ml of distilled water, and the suspended solution was refluxed and agitated for 12 hours. Then, the resultant was extracted with dichloromethane and distilled water, and the obtained organic layer was filtered through silica gel. Then, after removing an organic solution therefrom, a solid product was obtained through a silica gel column with hexane:dichloromethane=7:3 (volume to volume, v/v), and recrystallized with dichloromethane and n-hexane to obtain 14.4 g (88%) of Compound C-10.

HRMS (70 eV, EI+): m/z calcd for C₃₆H₂₃N: 469.18, found: 469

Elemental Analysis: C, 92%; H, 5%

Synthesis Example 21: Synthesis of Compound B-10

Reaction Scheme (131)21

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Synthesis of Compound (J)

26.96 g (81.4 mmol) of N-phenyl carbazole-3-boronic acid pinacolate and 23.96 g (97.36 mmol) of 3-bromo carbazole were mixed with 230 mL of tetrahydrofuran and 100 ml of 2 molar (M) potassium carbonate aqueous solution, and the mixture was heated under reflux in a nitrogen stream for 12 hours. After the reaction was completed, a solid produced by pouring methanol into the reactant was filtered and then dissolved in chlorobenzene, activated carbon and anhydrous magnesium sulfate were added thereto, and the mixture was agitated. The solution was filtered and recrystallized by using chlorobenzene and methanol to obtain 22.6 g (68%) of Compound (J).

HRMS (70 eV, EI+): m/z calcd for C₃₀H₂₀N₂: 408.16, found: 408

Elemental Analysis: C, 88%; H, 5%

Synthesis of Compound B-10

22.42 g (54.88 mmol) of Compound (J), 20.43 g (65.85 mmol) of 2-bromo-4,6-diphenylpyridine, and 7.92 g (82.32 mmol) of tertiary butoxy sodium were dissolved in 400 ml of toluene, and 1.65 g (1.65 mmol) of palladium dibenzylideneamine and 1.78 g (4.39 mmol) of tertiary butyl phosphorus were added in a dropwise fashion. The reaction solution was heated under reflux at 110° C. under a nitrogen stream for 12 hours. After the reaction was completed, a solid produced by pouring methanol into the reactant was filtered and then dissolved in chlorobenzene, activated carbon and anhydrous magnesium sulfate were added to thereto, and the mixture was agitated. The solution was filtered and recrystallized by using chlorobenzene and methanol to obtain 28.10 g (80%) of Compound B-10.

HRMS (70 eV, EI+): m/z calcd for C₄₇H₃₁N₃: 637.25, found: 637

Elemental Analysis: C, 89%; H, 5%

Synthesis Example 22: Synthesis of Compound B-31

Reaction Scheme (131)22

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9.97 g (30.95 mmol) of phenylcarbazolyl bromide, 9.78 g (34.05 mmol) of phenylcarbazolyl boronic acid, 12.83 g (92.86 mmol) of potassium carbonate, and 1.07 g (0.93 mmol) of tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml of toluene and 50 ml of distilled water, and the suspended solution was refluxed and agitated for 12 hours. Then, the resultant was extracted with dichloromethane and distilled water, and the organic layer was filtered through silica gel therefrom. Then, after removing an organic solution therefrom, a solid product obtained was recrystallized with dichloromethane and n-hexane, obtaining 13.8 g (92%) of Compound B-31.

HRMS (70 eV, EI+): m/z calcd for C₃₆H₂₄N₂: 484.19, found: 484

Elemental Analysis: C, 89%; H, 5%

Compound 23: Synthesis of Compound B-34

Reaction Scheme (131)23

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14.62 g (30.95 mmol) of triphenyl carbazolyl bromide, 9.78 g (34.05 mmol) of phenylcarbazolyl boronic acid, 12.83 g (92.86 mmol) of potassium carbonate, and 1.07 g (0.93 mmol) of tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml of toluene and 50 ml of distilled water, and the suspended solution was refluxed and agitated for 12 hours. Then, the resultant was extracted with dichloromethane and distilled water, and the organic layer produced therein was filtered through silica gel. Then, a solid product obtained after removing an organic solution therefrom was recrystallized with dichloromethane and n-hexane to obtain 16.7 g (85%) of Compound B-34.

HRMS (70 eV, EI+): m/z calcd for C₄₇H₂₉N₂: 621.23, found: 621

Elemental Analysis: C, 91%; H, 5%

Synthesis Example 24: Synthesis of Compound B-43

Reaction Scheme (131)24

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12.33 g (30.95 mmol) of biphenylcarbazolyl bromide, 12.37 g (34.05 mmol) of biphenylcarbazolyl boronic acid, 12.83 g (92.86 mmol) of potassium carbonate, and 1.07 g (0.93 mmol) of tetrakis-(triphenylphosphine)palladium (0) were suspended in 120 ml of toluene and 50 ml of distilled water, and the suspended solution was refluxed and agitated for 12 hours. Then, the resultant was extracted with dichloromethane and distilled water, and the organic layer produced therein was filtered through silica gel. Then, a solid product obtained after removing an organic solution therefrom was recrystallized with dichloromethane and n-hexane to obtain 18.7 g (92%) of Compound B-43.

HRMS (70 eV, EI+): m/z calcd for C₄₈H₃₂N₂: 636.26, found: 636

Elemental Analysis: C, 91%; H, 5%

Synthesis Example 25: Synthesis of Compound B-114

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Under a nitrogen atmosphere, 20.00 g (50.21 mmol) of 3-bromo-N-biphenylcarbazole and 18.54 g (50.21 mmol) of N-phenylcarbazole-3-boronic ester were mixed with 175 mL of tetrahydrofuran:toluene (1:1) and 75 mL of 2 M potassium carbonate solution in a 500-mL round-bottom flask with an agitator, 2.90 g (2.51 mmol) of tetrakis-(triphenylphosphine)palladium (0) was added thereto, and the mixture was heated under reflux under a nitrogen stream for 12 hours. After the reaction was completed, a solid produced by pouring the reactant into methanol was filtered, thoroughly washed with water and methanol, and dried. The result obtained therefrom was heated and dissolved in 700 mL of chlorobenzene, the solution was filtered through silica gel, and the solvent was completely removed. Then, the resultant was heated and dissolved in 400 mL of chlorobenzene and then recrystallized to obtain 19.15 g (68%) of Compound A2.

calcd. C₄₂H₂₈N₂: C, 89.97; H, 5.03; N, 5.00; found: C, 89.53; H, 4.92; N, 4.89

Synthesis Example 26: Synthesis of Compound B-14

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Compound B-14 was synthesized in the same manner as in Synthesis Example 24, except that Intermediate B-14(1) (3-bromo-9-(2,6-diphenylpyridin-4-yl)-9H-carbazole) and Intermediate B-14(2) ((9-([1,1′:3′,1″-terphenyl]-5′-yl)-9H-carbazol-3-yl)boronic acid) were respectively used instead of biphenylcarbazolyl bromide and biphenylcarbazolylboronic acid.

Synthesis Example 27: Synthesis of Compound B-15

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Compound B-15 was synthesized in the same manner as in Synthesis Example 24, except that Intermediate B-15(1) (3-bromo-9-(4,6-diphenylpyridin-2-yl)-9H-carbazole) and Intermediate B-15(2) ((9-(naphthalen-1-yl)-9H-carbazol-3-yl)boronic acid) were respectively used instread of biphenylcarbazolyl bromide and biphenylcarbazolylboronic acid.

Example 1

An anode was prepared by cutting an ITO glass substrate, on which an ITO electrode was deposited, to a size of 50 mm×50 mm×0.5 mm (mm=millimeter), ultrasonically cleaning the ITO glass substrate (anode) using acetone, iso-propyl alcohol, and pure water each for 15 minutes, and exposing the ITO glass substrate (anode) to irradiation of UV for 30 minutes and ozone to clean.

Compound HT3 and F4-TCNQ (a centration of F4-TCNQ in a hole injection layer was 3 percent by weight, wt %) were co-deposited on the anode at a deposition rate of 1 Angstrom per second (Å/sec) to form a hole injection layer having a thickness of 100 Angstroms (Å), and Compound HT3 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 1,660 Å.

A dopant and a host were co-deposited on the hole transport layer to form an emission layer having a thickness of 400 Å.

Materials used as the dopant and the host in Examples and Comparative Examples, content of the dopant in the emission layer, a weight ratio between two hosts when two host were used are shown in Table 2 below.

Compound ET16 and LiQ were co-deposited on the emission layer at a weight ratio of 5:5 to form an electron transport layer having a thickness of 360 Å. Then, LiQ was deposited on the electron transport layer to form an electron injection layer having a thickness of 5 Å, and an A1 electrode having a thickness of 800 Å was formed on the electron injection layer, thereby completing the manufacture of an organic light-emitting device.

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

The driving voltage, current efficiency, power efficiency, and lifespan (T₉₅) of the organic light-emitting devices manufactured in Examples 1 to 8 and Comparative Examples 1 and 2 were evaluated. Results thereof are shown in Table 2. This evaluation was performed using a current-voltage meter (Keithley 2400) and a luminescence meter (Minolta Cs-1,000A), and the lifespan (T₉₅) (at 6000 nit) was evaluated by measuring the amount of time that elapsed until luminance was reduced to 95% of the initial brightness of 100%.

TABLE 2

Driving
Current
Power
Lifespan

Host
Weight ratio of
Voltage
Efficiency
Efficiency
(hr)

Dopant
host 1
host 2
host 1:host 2
(V)
(cd/A)
(lm/W)
(T₉₅)

Example 1
Compound 1
Compound
Compound
5:5
4.3
53
38.7
250

(10 wt %)
B-31
A-14

Example 2
Compound 1
Compound
Compound
5:5
4.1
55
42.1
265

(10 wt %)
B-43
A-15

Example 3
Compound 3
Compound
Compound
5:5
4.5
50
34.9
190

(10 wt %)
B-43
B-14

Example 4
Compound 3
Compound
Compound
5:5
4.2
51
38.1
200

(10 wt %)
B-43
B-15

Example 5
Compound
Compound
Compound
5:5
4.1
55
42.1
290

146
B-31
A-14

(10 wt %)

Example 6
Compound
Compound
Compound
5:5
4.0
56
44.0
320

146
B-43
A-15

(10 wt %)

Example 7
Compound
Compound
Compound
5:5
3.7
51
43.3
215

322
B-31
A-14

(10 wt %)

Example 8
Compound
Compound
Compound
5:5
3.6
53
46.2
240

322
B-43
A-15

(10 wt %)

Comparative
Ir(ppy)₃
Compound
Compound
5:5
4.8
45
29.4
110

Example 1
(10 wt %)
B-31
B-14

Comparative
Comparative
Compound
Compound
5:5
4.6
48
32.8
135

Example 2
Compound A
B-31
B-14

(10 wt %)

Compound 1

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Compound 3

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Compound 8

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Compound 22

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Compound 32

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Compound 35

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Compound 146

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Compound 300

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Compound 305

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Compound 322

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Compound 327

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Comparative Compound A

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A-14

A-15

B-14

B-15

B-31

B-43

Referring to table 2, it was confirmed that the organic light-emitting devices of Examples 1 to 8 had excellent driving voltage, current efficiency, power efficiency, and lifespan characteristics, compared to those of Comparative Examples 1 and 2.

According to one or more embodiments, the organic light-emitting device may have low driving voltage, high efficiency, and long lifespan characteristics.

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	15387137	Dec 2016	US
Child	17381374		US

ORGANIC LIGHT-EMITTING DEVICE

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