Organometallic compound, organic light-emitting device including same, and electronic device including organic light-emitting device

Abstract

Disclosed are an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. The organometallic compound is represented by Formula 1, where M1 is a transition metal, L1 is a ligand represented by Formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, where X1 is C or N; x2 is C or N; x3 is C or N; and X4 is C or N; y1 is O, S or Se; ring CY1 and ring CY3 are each independently a 5-membered heterocyclic group, a 5-membered heterocyclic group fused with a C5-C30 carbocyclic group, or a 5-membered heterocyclic group fused with a C1-C30 heterocyclic group; ring CY2, ring CY4, and ring CY5 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group; and the remaining groups and variables in Formulae 1A and 1B are as defined herein. Formula 1M1 (L1) n1 (L2) n2 # imgabs0 #

Description

[0001] CROSS-REFERENCE TO RELATED APPLICATIONS

[0002] This application claims priority to and the benefits of Korean Patent Application No. 10-2023-0150291 filed on November 2, 2023 in the Korean Intellectual Property Office, and all rights arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field

[0003] One or more aspects relate to an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. Background Art

[0004] Organic light emitting devices (OLEDs) are self-emitting devices having excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed. In addition, OLEDs can produce full-color images.

[0005] An organic light emitting device typically includes an anode, a cathode, and an organic layer disposed between the anode and the cathode and including 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. Holes and electrons recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] One or more aspects relate to an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device.

[0007] Additional aspects will be set forth in part in the detailed description which follows and, in part, will be apparent from the detailed description, or may be learned by practice of the exemplary embodiments presented herein.

[0008] According to one aspect, an organometallic compound represented by Formula 1 is provided:

[0009] Formula 1

[0010] M 1 (L 1 ) n1 (L 2 ) n2

[0011] Among them, in formula 1,

[0012] M 1 For transition metals,

[0013] L 1is a ligand represented by Formula 1A,

[0014] L 2 is a ligand represented by Formula 1B, and

[0015] n1 and n2 are each independently 1 or 2,

[0016] Formula 1A

[0017]

[0018] Formula 1B

[0019]

[0020] Wherein, in Formula 1A and 1B,

[0021] X 1 C or N, X 2 C or N, X 3 is C or N, and X 4 is C or N,

[0022] Y 1 is O, S or Se,

[0023] Cyclo 1 and CY 3 Each independently is a 5-membered heterocyclic group, and C 5 -C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 a 5-membered heterocyclic group fused to a heterocyclic group,

[0024] Cyclo 2 CY 4 and CY 5 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0025] R 1 To R 4 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),

[0026] R 5 for:

[0027] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio,

[0028] cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, each unsubstituted or substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39)、-P(=O)(Q 38 )(Q 39 ), or a combination thereof, or

[0029] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),

[0030] T 1 for:

[0031] deuterium;

[0032] Each of the C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, or

[0033] Each is deuterated and C 1 -C 10 alkyl-substituted cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl,

[0034] b1 to b5 and c1 are each independently an integer from 1 to 10,

[0035] Substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently:

[0036] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio,

[0037] Each of the following C 1 -C 60Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof,

[0038] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group,

[0039] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q29 ), or a combination thereof, or

[0040] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0041] Q 1 To Q 9 , Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0042] According to another aspect, an organic light emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0043] At least one organic metal compound represented by Formula 1 may be included in an emission layer of the organic layer, and the at least one organic metal compound represented by Formula 1 included in the emission layer may serve as a dopant. BRIEF DESCRIPTION OF THE DRAWINGS

[0044] The above and other aspects, features, and advantages of some exemplary embodiments will become more apparent from the following detailed description considered in conjunction with the accompanying drawings, in which:

[0045] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0046] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings, wherein the same reference numerals refer to the same elements throughout. In this regard, the exemplary embodiments may have different forms and should not be construed as being limited to the detailed description set forth herein. Therefore, exemplary embodiments are only described in further detail below with reference to the accompanying drawings to illustrate some aspects and features of the detailed description. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Throughout the disclosure, the expression "at least one (kind) of a, b or c" means only a, only b, only c, both a and b, both a and c, both b and c, all of a, b and c, or variations thereof.

[0047] The terms used herein are only used for the purpose of describing one or more exemplary embodiments and are not intended to be restrictive. As used herein, the singular forms "a (kind) (indefinite article) (a, an)" and "said (the)" are also intended to include plural forms, unless the context clearly indicates otherwise. The term "or" means "and / or". It will be further understood that the term "comprising" or "including" when used in this specification indicates that there are stated features, regions, wholes, steps, operations, elements, and / or components, but does not exclude the presence or addition of one or more other features, regions, wholes, steps, operations, elements, components, and / or their collections.

[0048] It will be understood that although the terms first, second, third, etc. can be used to describe various elements, components, regions, layers and / or parts in this article, these elements, components, regions, layers and / or parts should not be limited by these terms. These terms are only used to distinguish an element, component, region, layer or part from other elements, components, regions, layers or parts. Therefore, without departing from the teaching of the present embodiment, the first element, component, region, layer or part discussed below can be referred to as the second element, component, region, layer or part.

[0049] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0050] It will be understood that when an element is referred to as being “on” another element, it can be in direct contact with the other element or intervening elements may exist therebetween. In contrast, when an element is referred to as being “directly on” another element, there are no intervening elements.

[0051] 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 consistent with their meaning in the context of this disclosure and the relevant art, and will not be interpreted in an idealized or overly formal sense unless clearly so defined herein.

[0052] As used herein, "about" or "approximately" includes 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 taking into account the measurement in question and the errors associated with the 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 ±10% or 5% relative to the stated value.

[0053] As used herein, an "energy level" (e.g., a singlet state (S 1 ) energy level or triplet state (T 1 ) energy level) is expressed as an absolute value from the vacuum energy level. In addition, when the energy level is referred to as "deep", "high" or "large", the energy level has a large absolute value based on the vacuum energy level of "0 electron volt (eV)", and when the energy level is referred to as "shallow", "low" or "small", the energy level has a small absolute value based on the vacuum energy level of "0 eV".

[0054] According to one aspect, the organometallic compound is represented by Formula 1:

[0055] Formula 1

[0056] M 1 (L 1 ) n1 (L 2 ) n2

[0057] Where M in Formula 1 1 For transition metals.

[0058] For example, M 1 It may be a first row transition metal of the periodic table, a second row transition metal of the periodic table, or a third row transition metal of the periodic table.

[0059] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), palladium (Pd), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0060] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).

[0061] In one or more embodiments, M 1 It may be iridium (Ir).

[0062] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0063] In one or more embodiments, the sum of n1 and n2 may be 2 or 3.

[0064] In one or more embodiments, M 1 It may be iridium (Ir), and the sum of n1 and n2 may be 3.

[0065] In one or more embodiments, M 1 It may be platinum (Pt), and the sum of n1 and n2 may be 2.

[0066] L in Formula 1 1 is a ligand represented by Formula 1A:

[0067] Formula 1A

[0068]

[0069] Wherein, in Formula 1A, X 1 is C or N, and X 2 It is C or N.

[0070] In one or more embodiments, X 1 Can be N, and X 2 Can be C.

[0071] Ring CY in Formula 1A 1 is a 5-membered heterocyclic group, 5 -C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 The heterocyclic group is a condensed 5-membered heterocyclic group.

[0072] In one or more embodiments, CY 1 It may be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

[0073] Ring CY in Formula 1A 2 C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0074] In one or more embodiments, CY 2It may be a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0075] In one or more embodiments, in Formula 1A,

[0076] Cyclo 1 may be an imidazole group or a benzimidazole group, and

[0077] Cyclo 2 It may be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0078] In one or more embodiments, in Formula 1A, The moiety represented by may be a group represented by one of the formulae CY(1)-1 to CY(1)-3:

[0079]

[0080] Wherein, in formulas CY(1)-1 to CY(1)-3,

[0081] X 11 Can be C(R 11a )、C(R 11a )(R 11b ), N, or N(R 11a ),

[0082] X 12 Can be C(R 12a )、C(R 12a )(R 12b ), N, or N(R 12a ),

[0083] X 13 Can be C(R 13a )、C(R 13a )(R 13b ), N, or N(R 13a ),

[0084] Cyclo 10 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0085] R 10 , R 11a , R 11b , R 12a , R 12b , R 13a , and R 13b can be independently as described herein for R 1 As defined,

[0086] b10 can be an integer from 1 to 10,

[0087] represents a single bond or a double bond,

[0088] *Indicates the same as M 1 The binding site, and

[0089] *” indicates the binding site with the adjacent atoms.

[0090] In one or more embodiments, the ring CY in formula CY(1)-2 and CY(1)-3 10 It may be a benzene group, a naphthyl group, a pyrimidine group, a pyrazine group, or a pyridazine group.

[0091] In one or more embodiments, in Formula 1A, The moiety represented by may be a group represented by one of the formulae CY(2)-1 to CY(2)-16:

[0092]

[0093] Wherein, in formulas CY(2)-1 to CY(2)-16,

[0094] R 21 To R 24 can be independently as described herein for R 2 Defined, the condition is R 21 To R 24 It cannot be hydrogen.

[0095] *' indicates that the 1 The binding site, and

[0096] *” indicates the binding site with the adjacent atoms.

[0097] In one or more embodiments, L 1 It may be a ligand represented by Formula 1A-1 or Formula 1A-2:

[0098]

[0099] Wherein, in Formulas 1A-1 and 1A-2,

[0100] R10 To R 13 can be independently as described herein for R 1 As defined,

[0101] R 2 As described in this article,

[0102] c2 and c10 may each independently be an integer from 1 to 4, and

[0103] * and *' respectively represent 1 binding site.

[0104] In one or more embodiments, R in Formula 1A-1 and 1A-2 11 Can be substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, or substituted or unsubstituted C 6 -C 60 Aryl.

[0105] L in Formula 1 2 is a ligand represented by Formula 1B:

[0106] Formula 1B

[0107]

[0108] Wherein, in Formula 1B, X 3 is C or N, and X 4 It is C or N.

[0109] In one or more embodiments, X 3 Can be N, and X 4 Can be C.

[0110] Y in Formula 1B 1 It is O, S or Se.

[0111] Ring CY in Formula 1B 3 is a 5-membered heterocyclic group, 5 -C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 The heterocyclic group is a condensed 5-membered heterocyclic group.

[0112] In one or more embodiments, CY 3 It may be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

[0113] Ring CY in Formula 1B 4 and CY 5 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0114] In one or more embodiments, CY 4 and CY 5 Each of the above groups may independently be a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0115] In one or more embodiments, in Formula 1B,

[0116] Cyclo 3 may be an imidazole group or a benzimidazole group, and

[0117] Cyclo 4 and CY 5 Each may independently be a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0118] In one or more embodiments, in Formula 1B, The moiety represented by may be a group represented by one of the formulae CY(3)-1 to CY(3)-3:

[0119]

[0120] Wherein, in formulas CY(3)-1 to CY(3)-3,

[0121] X 31 Can be C(R 31a )、C(R 31a )(R 31b ), N, or N(R 31a ),

[0122] X 32 Can be C(R 32a )、C(R 32a )(R 32b ), N, or N(R 32a ),

[0123] X33 Can be C(R 33a )、C(R 33a )(R 33b ), N, or N(R 33a ),

[0124] Cyclo 30 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0125] R 30 , R 31a , R 31b , R 32a , R 32b , R 33a , and R 33b can be independently as described herein for R 3 As defined,

[0126] b30 can be an integer from 1 to 10,

[0127] represents a single bond or a double bond,

[0128] *Indicates the same as M 1 The binding site, and

[0129] *” indicates the binding site with the adjacent atoms.

[0130] In one or more embodiments, in Formula 1B, The moiety represented by may be a group represented by one of the formulae CY(4)-1 to CY(4)-6:

[0131]

[0132] Wherein, in formulas CY(4)-1 to CY(4)-6,

[0133] X 4 , Y 1 , R 4 , and R 5 may each independently be as described herein,

[0134] T 11 To T 16 can be independently as described herein for T 1 As defined,

[0135] R 41 and R 42 can be independently as described herein for R 4 As defined,

[0136] b41 can be 1 or 2,

[0137] b51 can be an integer from 1 to 4,

[0138] b52 can be an integer from 1 to 3,

[0139] *' indicates that the 1 The binding site, and

[0140] *” indicates the binding site with the adjacent atoms.

[0141] In one or more embodiments, L 2 It may be a ligand represented by Formula 1B-1 or 1B-2:

[0142]

[0143] Wherein, in Formulas 1B-1 and 1B-2,

[0144] X 4 , Y 1 , R 4 , R 5 , and T 1 may each be as described herein,

[0145] R 30 To R 33 can be independently as described herein for R 3 As defined,

[0146] c4 can be 1 or 2,

[0147] c3 and c5 can each independently be an integer from 1 to 4,

[0148] c10 may be an integer from 1 to 6, and

[0149] * and *' respectively represent 1 binding site.

[0150] In one or more embodiments, R in Formula 1B-1 and 1B-2 31 Can be substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, or substituted or unsubstituted C 6 -C 60 Aryl.

[0151] R in Formula 1A and 1B 1 To R 4 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ).

[0152] In one or more embodiments, R 1 To R 4 Can be independently:

[0153] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0154] Each of the following C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof;

[0155] Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;

[0156] cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or

[0157] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),and

[0158] Q 1 To Q 9 Can be independently:

[0159] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD2 CD 2 H, or -CD 2 CDH 2 ;

[0160] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0161] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0162] R in Formula 1B 5 for:

[0163] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio;

[0164] cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, each unsubstituted or substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2-C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 38 )、-P(=O)(Q 38 )(Q 39 ), or a combination thereof; or

[0165] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),

[0166] Where Q 1 To Q 9 and Q 31 To Q 39 As defined herein.

[0167] In one or more embodiments, R 5 Can be:

[0168] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0169] Each of the following C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof;

[0170] cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl;

[0171] cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, or a combination thereof; or

[0172] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),and

[0173] Q 1 To Q 9 Can be independently:

[0174] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0175] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0176] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C1 -C 10 Alkyl, phenyl, or a combination thereof.

[0177] In one or more embodiments, R 1 To R 4 Can be independently:

[0178] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0179] A group represented by one of formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, or 10-201 to 10-353; or

[0180] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5 ),and

[0181] R 5 Can be:

[0182] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0183] A group represented by one of the formulas 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1, 10-2, 10-12 to 10-58, 10-67 to 10-69, 10-99 to 10-101, 10-105 to 10-114, 10-206, 10-207, 10-211 to 10-217, 10-232 to 10-237, 10-273 to 10-281, 10-283 to 10-304, 10-311 to 10-314, 10-344, or 10-345; or -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5 ), where Q 1 To Q 5 As defined in this article:

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193] In formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, "Ph" is a phenyl group, "TMS" is a trimethylsilyl group, and "TMG" is a trimethylgermyl group.

[0194] T in Formula 1B 1 for:

[0195] deuterium;

[0196] Each of the C 1 -C 10 alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl; or

[0197] Each is deuterated and C 1 -C 10 Alkyl-substituted cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl.

[0198] In formula 1B, (T 1 ) c1 In other words, the number of R in formula 1B is b4 4 and R with quantity b5 5 Among all the groups, there are c1 T 1 , where T 1 As defined herein. In other words, satisfying T 1 Definition of R 4 Group and meet T 1 Definition of R 5 The group is also called T 1 .

[0199] In one or more embodiments, T 1 Can be:

[0200] -CD 3 、-CD 2 H, or -CDH 2 ;or

[0201] A group represented by one of formulae 8-1 to 8-14:

[0202]

[0203] * in Formulae 8-1 to 8-14 represents a bonding site with an adjacent atom.

[0204] b1 to b5 and c1 in Formulas 1A and 1B are each independently an integer of 1 to 10. * and *' in Formulas 1A and 1B each represent 1 binding site.

[0205] In one or more embodiments, c1 in Formula 1B may be 1 or 2.

[0206] In one or more embodiments, the organometallic compound represented by Formula 1 may be represented by one of Compounds 1 to 60:

[0207]

[0208]

[0209]

[0210]

[0211] In one or more embodiments, the organometallic compound represented by Formula 1 may be electrically neutral.

[0212] The organometallic compound represented by Formula 1 satisfies the structure of Formula 1 described above and includes ligands represented by Formulas 1A and 1B, and Formula 1B includes a substituent containing deuterium (T 1 ). Due to this structure, the organic metal compound represented by Formula 1 has excellent light emitting characteristics, and has characteristics suitable for use as a light emitting material with high color purity by controlling the emission wavelength range.

[0213] The organometallic compound represented by Formula 1 may have excellent electrical mobility, and thus, an electronic device such as an organic light emitting device including at least one of the organometallic compounds represented by Formula 1 may exhibit low driving voltage, high external quantum efficiency, and / or long lifetime.

[0214] The density functional theory (DFT) method of Gaussian 09 program was used to calculate the highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the singlet state (S) energy level and the molecular structure of the organometallic compound represented by Formula 1 under the condition of optimizing the molecular structure at the B3LYP level. 1 ) energy level, and triplet state (T 1 ) energy levels, and the results are shown in Table 1. The energy levels are expressed in electron volts (eV).

[0215] Table 1

[0216]

[0217]

[0218] As confirmed by Table 1, the organometallic compound represented by Formula 1 has such electrical characteristics as to be suitable for use as a dopant for electronic devices such as organic light emitting devices.

[0219] In one or more embodiments, the maximum emission wavelength (emission peak wavelength or peak emission wavelength, λ) of the emission peak of the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound represented by Formula 1 is max ) may be from about 490 nanometers (nm) to about 550 nm, from about 500 nm to about 540 nm, or from about 510 nm to about 530 nm.

[0220] The synthesis method of the organometallic compound represented by Formula 1 may be recognized by one of ordinary skill in the art by referring to the synthesis examples provided below.

[0221] The organic metal compound represented by Formula 1 may be suitable for use in an organic layer of an organic light-emitting device, for example, suitable for use as a dopant in an emission layer of the organic layer. Therefore, according to one or more embodiments, an organic light-emitting device includes a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organic metal compound represented by Formula 1. The at least one organic metal compound represented by Formula 1 may be included in the emission layer.

[0222] By including at least one of the organometallic compounds represented by Formula 1 as described above, the organic light emitting device may have excellent driving voltage, excellent maximum external quantum efficiency, and excellent lifespan characteristics.

[0223] The organic metal compound represented by Formula 1 may be used between the electrode pairs of the organic light-emitting device. For example, the organic metal compound represented by Formula 1 may be included in the emission layer. In this regard, the organic metal compound represented by Formula 1 may be used as a dopant, and the emission layer may further include a host. When the emission layer further includes a host, the amount of the host in the emission layer may be greater than the amount of the at least one organic metal compound represented by Formula 1 in the emission layer based on weight.

[0224] In one or more embodiments, the emitting layer may emit green light. For example, the emitting layer may emit green light having a maximum emission wavelength of about 490 nm to about 550 nm, about 500 nm to about 540 nm, or about 510 nm to about 530 nm.

[0225] As used herein, the expressions “(the organic layer) includes at least one organometallic compound represented by Formula 1” and “(the organic layer) includes at least one of the organometallic compounds represented by Formula 1” may be used interchangeably herein and may be interpreted as “(the organic layer) may include one organometallic compound represented by Formula 1, or at least two different organometallic compounds represented by Formula 1”.

[0226] For example, the organic layer may include only Compound 1 as the at least one organic metal compound represented by Formula 1. In this regard, Compound 1 may be included in the emission layer of the organic light-emitting device. In one or more embodiments, the organic layer may include Compound 1 and Compound 2 as the at least one organic metal compound represented by Formula 1. In this regard, Compound 1 and Compound 2 may be present in the same layer (for example, both Compound 1 and Compound 2 may be present in the emission layer).

[0227] The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode, and the second electrode may be an anode as a hole injection electrode.

[0228] For example, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer (HIL), a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer (EIL), or a combination thereof.

[0229] The term "organic layer" as used herein refers to a single layer or a plurality of layers disposed between the first electrode and the second electrode of the organic light emitting device. In addition to organic compounds, the "organic layer" may also include an organic metal complex including a metal, and the like.

[0230] Figure 1 FIG. 1 is a schematic cross-sectional view of an organic light-emitting device 10 according to one or more embodiments. Figure 1 The structure and manufacturing method of the organic light emitting device 10 according to one or more embodiments are described. The organic light emitting device 10 may have a structure in which the first electrode 11, the organic layer 15, and the second electrode 19 are sequentially stacked in the stated order.

[0231] A substrate may be further provided under the first electrode 11 or on the second electrode 19. The substrate may be a substrate used in a conventional organic light-emitting device, for example, a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and / or waterproofness.

[0232] The first electrode 11 can be formed by, for example, depositing or sputtering a material for forming the first electrode 11 onto the substrate. The first electrode 11 can be an anode. The material for forming the first electrode 11 can be selected from materials having a high work function to facilitate hole injection. The first electrode 11 can be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. The material for forming the first electrode 11 can be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).

[0233] The first electrode 11 may have a single-layer structure or a multi-layer structure including at least two layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the structure of the first electrode 11 is not limited thereto.

[0234] The organic layer 15 may be disposed on the first electrode 11 .

[0235] The organic layer 15 may include a hole transport region, an emission layer, and an electron transport region.

[0236] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0237] The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.

[0238] The hole transport region may include only a hole injection layer or a hole transport layer. In one or more embodiments, the hole transport region may be a hole injection layer / hole transport layer structure, or a hole injection layer / hole transport layer / electron blocking layer structure, wherein the corresponding layers of each structure are sequentially stacked in the stated order starting from the first electrode 11.

[0239] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using various methods such as vacuum deposition, spin coating, casting, and / or Langmuir-Blodgett (LB) deposition, but the embodiment is not limited thereto.

[0240] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the compound used as the material for forming the hole injection layer, and the structure and thermal characteristics of the hole injection layer to be formed, and may include a deposition temperature of about 100° C. to about 500° C., ... -8 To about 10 -3 Torr vacuum pressure, and about 0.01 angstroms / second ( / second) to about However, the deposition conditions are not limited thereto.

[0241] When the hole injection layer is formed by spin coating, coating conditions may vary according to a compound used as a material for forming the hole injection layer, and a structure and thermal characteristics of the hole injection layer, and may include a coating speed of about 2,000 revolutions per minute (rpm) to about 5,000 rpm, and a heat treatment temperature of about 80° C. to about 200° C. for removing a solvent after coating. However, the coating conditions are not limited thereto.

[0242] The conditions for forming the hole transport layer and the electron blocking layer may refer to the description provided for the conditions for forming the hole injection layer.

[0243] The hole transport region may include, for example, at least one of 4,4′,4″-tris(3-methylphenylamino)triphenylamine (m-MTDATA), 4,4′,4″-tris(N,N-diphenylamino)triphenylamine (TDATA), 4,4′,4″-tris{N-(2-naphthyl)-N-phenylamino}-triphenylamine (2-TNATA), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (NPB), β-NPB, N,N′-bis(3-methylphenyl)-N,N′-diphenyl-[1,1-biphenyl]-4,4′-diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4,4′-diamine ... '-cyclohexylenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4'-bis[N,N'-(3-methylphenyl)amino]-3,3'-dimethylbiphenyl (HMTPD), 4,4',4"-tri(N-carbazolyl)triphenylamine (TCTA), polyaniline / dodecylbenzenesulfonic acid (PANI / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (PANI / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), a compound represented by Formula 201, or a compound represented by Formula 202, but the embodiment is not limited thereto:

[0244]

[0245] Formula 201

[0246]

[0247] Formula 202

[0248]

[0249] Ar in Formula 201 101 and Ar 102 Can be independently:

[0250] Phenylene, cyclopentadienylene, indenylene, naphthylene, azulenylene, heptalenylene, acenaphthenylene, fluorenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyren ... phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene, phenanthrenylene phenylene, tetraphenylene, perylene, perylene, or pentphenylene; or

[0251] each substituted with at least one of the following: phenylene, pentalene, indenylene, naphthylene, azulenylene, heptalene, acenaphthene, fluorenylene, phenalenylene, phenanthrenylene, anthracenylene, fluoranthenylene, benzo[9,10]phenanthrenylene, pyrenylene, acenaphthene, fluor ... phenanthrenylene, phenanthrenylene, phen phenylene, tetraphenylene, perylene, or pentphenylene: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

[0252] Xa and xb in Formula 201 may each independently be an integer from 0 to 5, or 0, 1, or 2. For example, Xa may be 1, and Xb may be 0, but Xa and Xb are not limited thereto.

[0253] R in formula 201 and 202 101 To R 108 , R 111 To R 119 and R 121 To R 124 Can be independently:

[0254] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentyloxy, etc.), or C 1 -C 10 Alkylthio;

[0255] Each of the following C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or a combination thereof;

[0256] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0257] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 1 -C 10 An alkylthio group, or a combination thereof, but the embodiment is not limited thereto.

[0258] R in Formula 201 109 Can be:

[0259] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0260] Phenyl, naphthyl, anthracenyl, or pyridyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 alkylthio, phenyl, naphthyl, anthracenyl, pyridyl, or a combination thereof.

[0261] According to one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0262] Formula 201A

[0263]

[0264] R in Formula 201A 101 , R 111 , R 112 , and R 109 Each may be as described herein.

[0265] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, at least one of compounds HT1 to HT20:

[0266]

[0267]

[0268]

[0269] The thickness of the hole transport region may be about 100 angstroms. to about For example to about When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer may have a thickness of about to about For example to about And the thickness of the hole transport layer may be about to about For example to about When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics may be obtained without a significant increase in driving voltage.

[0270] In addition to the above materials, the hole transport region may further include a charge generating material for improving conductivity. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0271] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiment is not limited thereto. Non-limiting examples of the p-dopant include quinone derivatives such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinodimethane (F4-TCNQ), 1,3,4,5,7,8-hexafluorotetracyanonaphthoquinodimethane (F6-TCNNQ), etc.; metal oxides such as tungsten oxide, molybdenum oxide, etc.; or compounds containing a cyano group such as compounds HT-D1 or F12, but the embodiment is not limited thereto:

[0272]

[0273] The hole transport region may further include a buffer layer.

[0274] The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, thereby increasing efficiency.

[0275] In some embodiments, when the hole transport region includes an electron blocking layer, the material used to form the electron blocking layer may be selected from, but not limited to, the materials described above that can be used in the hole transport region and the host material described below. For example, when the hole transport region includes an electron blocking layer, the material used for the electron blocking layer may be mCP described below.

[0276] An emission layer (EML) may be formed on the hole transport region by vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, deposition or coating conditions may generally be similar to those applied when forming the hole injection layer, although deposition or coating conditions may vary depending on the material used to form the emission layer.

[0277] The emission layer may include a host and a dopant, and the dopant may include at least one of the organic metal compounds represented by Formula 1.

[0278] The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN) (also referred to as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, or compound H51, but embodiments are not limited thereto:

[0279]

[0280] In one or more embodiments, the host may include a compound represented by Formula 301, but the embodiments are not limited thereto:

[0281] Formula 301

[0282]

[0283] Among them, Ar in formula 301 111 and Ar 112 Can be independently:

[0284] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0285] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0286] Ar in Formula 301 113 To Ar 116 Can be independently:

[0287] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0288] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0289] In Formula 301, g, h, i, and j may each independently be an integer of 0 to 4, and may be, for example, 0, 1, or 2.

[0290] Ar in Formula 301 113 To Ar 116 Can be independently:

[0291] C substituted with at least one of the following 1 -C 10 Alkyl: phenyl, naphthyl, anthracenyl, or a combination thereof;

[0292] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0293] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, fluorenyl, or a combination thereof; or

[0294] A group having the following structure:

[0295]

[0296] However, the implementation mode is not limited thereto.

[0297] In one or more embodiments, the host may include a compound represented by Formula 302:

[0298] Formula 302

[0299]

[0300] Ar in formula 302 122 To Ar 125 can be respectively combined with Ar in formula 301 113 Defined identically.

[0301] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, propyl, etc.).

[0302] In Formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may each independently be 0, 1, or 2.

[0303] 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 / or a blue emission layer. In one or more embodiments, the emission layer may have a structure in which a red emission layer, a green emission layer, and / or a blue emission layer are stacked, and therefore, various modifications such as emitting white light are possible.

[0304] When the emission layer includes a host and a dopant, an amount of the dopant in the emission layer may generally be about 0.01 parts by weight to about 15 parts by weight relative to 100 parts by weight of the host in the emission layer, but embodiments are not limited thereto.

[0305] The thickness of the emission layer may be about to about For example to about When the thickness of the emission layer is within these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0306] Next, an electron transport region may be located on the emission layer.

[0307] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0308] 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, and the structure of the electron transport region is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0309] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may refer to the description provided for the conditions for forming the hole injection layer.

[0310] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), or bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), but embodiments are not limited thereto:

[0311]

[0312] The thickness of the hole blocking layer may be about to about For example to about When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics may be obtained without a significant increase in driving voltage.

[0313] The electron transport layer may include at least one of the following: 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP), 4,7-diphenyl-1,10-phenanthroline (Bphen), tris(8-hydroxy-quinoline)aluminum (Alq 3 ), bis(2-methyl-8-hydroxyquinoline-N1,08)-(1,1′-biphenyl-4-hydroxy)aluminum (BAlq), 3-(4-biphenyl)-4-phenyl-5-tert-butylphenyl-1,2,4-triazole (TAZ), or 4-(naphthalene-1-yl)-3,5-diphenyl-4H-1,2,4-triazole (NTAZ), but the embodiments are not limited thereto:

[0314]

[0315] In one or more embodiments, the electron transport layer may include at least one of ET1 to ET25, but the embodiments are not limited thereto:

[0316]

[0317]

[0318]

[0319] The thickness of the electron transport layer may be about to about For example to about When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics may be obtained without a significant increase in driving voltage.

[0320] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0321] The metal-containing material may include a Li complex. The Li complex may include, for example, compound ET-D1 (8-hydroxyquinoline lithium, Liq) or ET-D2:

[0322]

[0323] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19 .

[0324] The electron injection layer may include compounds ET-D1, LiF, NaCl, CsF, Li 2 O, BaO, or a combination thereof.

[0325] The thickness of the electron injection layer may be about to about For example to about When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics may be obtained without a significant increase in driving voltage.

[0326] The second electrode 19 may be disposed on the organic layer 15. The second electrode 19 may be a cathode. The material for forming the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), 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, in order to manufacture a top-emitting light-emitting device, various modifications such as forming a transmissive second electrode using ITO or IZO are possible.

[0327] Already referred to Figure 1 The organic light emitting device is described, but embodiments are not limited thereto.

[0328] According to one or more embodiments, the diagnostic composition includes at least one organometallic compound represented by Formula 1.

[0329] The organometallic compound represented by Formula 1 may provide high luminescence efficiency, and thus, a diagnostic composition including at least one organometallic compound represented by Formula 1 may have high diagnostic efficiency.

[0330] The diagnostic composition can be used in various applications including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0331] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, and the like. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0332] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "C alkyl" as used herein is a monovalent group represented by an alkyl group, and non-limiting examples thereof include methoxy, ethoxy, isopropoxy, and the like. 1 -C 60 "Alkylthio" refers to -SA 101 (A 101 C 1 -C 60 A monovalent group represented by an alkyl group.

[0333] As used herein, the term "C 2 -C 60 "Alkenyl" refers to 2 -C 60 The alkyl group is a structure containing at least one carbon-carbon double bond in the middle or at the terminal, and non-limiting examples thereof include vinyl, propenyl, butenyl, and the like. As used herein, the term “C 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0334] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a C 2 -C 60 The term "C-alkyl" as used herein refers to a group containing at least one carbon-carbon triple bond in the middle or at the terminal of the alkyl group, and non-limiting examples thereof include ethynyl, propynyl, and the like. 2 -C 60 "Alkyne" refers to a group having a C 2 -C 60 Alkynyl is a divalent group of the same structure.

[0335] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0336] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent saturated ring group having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include tetrahydrofuranyl, tetrahydrothienyl, and the like. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0337] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent hydrocarbon ring group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and not having aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0338] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl group" refers to a monovalent ring group having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom, 1 to 10 carbon atoms as ring atoms, and at least one double bond in its ring and having no aromaticity. 1 -C 10 Non-limiting examples of heterocycloalkenyl include 2,3-dihydrofuranyl, 2,3-dihydrothienyl, and the like. As used herein, the term “C 1 -C 10 "Heterocycloalkenylene" refers to a 1 -C 10 Heterocycloalkenyl is a divalent group of the same structure.

[0339] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms as ring atoms, and the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms as ring atoms. 6 -C 60 Non-limiting examples of aryl groups include phenyl, naphthyl, anthracenyl, phenanthrenyl, pyrenyl, Ji et al. 6 -C 60 Aryl and C 6 -C 60 When the arylene groups each include two or more rings, the rings may be fused to each other.

[0340] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 54 Alkyl substituted C 6 -C 59 Aryl. As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a 6 -C 59 Aryl substituted C 1 -C 54 alkyl.

[0341] As used herein, the term "C 1 -C 60 "Heteroaryl" refers to a monovalent group having a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom and 1 to 60 carbon atoms as ring-forming atoms. As used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic ring system containing at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom and having 1 to 60 carbon atoms as ring atoms. 1 -C 60 Non-limiting examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like. 1 -C 60 Heteroaryl and C 1 -C 60When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0342] As used herein, the term "C 2 -C 60 "Alkylheteroaryl" refers to a 1 -C 59 Alkyl substituted C 1 -C 59 As used herein, the term "C 2 -C 60 "Heteroarylalkyl" refers to a 1 -C 59 Heteroaryl-substituted C 1 -C 59 alkyl.

[0343] As used herein, the term "C 6 -C 60 "Aryloxy" means -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" means -SA 103 (A 103 C 6 -C 60 aryl).

[0344] As used herein, the term "C 1 -C 60 "Heteroaryloxy" means -OA 104 (A 104 C 1 -C 60 Heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" means -SA 105 (A 105 C 1 -C 60 heteroaryl).

[0345] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) having two or more rings fused to each other, having only carbon atoms as ring-forming atoms, and not having aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused polycyclic groups include fluorenyl and the like. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic group.

[0346] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1 to 60 carbon atoms) having two or more rings fused to each other, having a heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring-forming atom in addition to carbon atoms, and having no aromaticity in terms of its entire molecular structure. Non-limiting examples of monovalent non-aromatic fused heteropolycyclic groups include carbazolyl and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0347] As used herein, the term "C 5 -C 30 The term "carbocyclic group" refers to a saturated or unsaturated ring group having only 5 to 30 carbon atoms as ring atoms. 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group.

[0348] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated ring group having 1 to 30 carbon atoms as ring atoms and at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as a ring atom. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0349] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C60 Aryl, substituted C 7 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0350] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0351] Each of the following C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof;

[0352] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6-C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0353] Each of the following C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1- C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or

[0354] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0355] Q 1 To Q 9 , Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0356] For example, Q 1 To Q 9 , Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 can be independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, or C each being unsubstituted or substituted by at least one of the following 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio group, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, C 1 -C 60 Alkyl, C 3 -C 10 Cycloalkyl, C 6 -C 60 aryl, or a combination thereof.

[0357] For example, Q 1 To Q 9 , Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 Can be independently:

[0358] -CH 3 、-CD 3 、-CD 2 H.-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H, -CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H, -CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H, or -CD 2 CDH 2 ;

[0359] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0360] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

[0361] Hereinafter, the organometallic compound represented by Formula 1 and the organic light-emitting device including the same according to one or more exemplary embodiments will be further described in detail with reference to Synthesis Examples and Examples. However, the following examples are not intended to limit the scope of the present disclosure. The phrase "using B instead of A" used in describing the Synthesis Examples means that the amount of A used is the same as the amount of B used in terms of molar equivalent.

[0362] Example

[0363] Synthesis Example 1: Synthesis of Compound 1

[0364]

[0365] Synthesis of compound 1A

[0366] 3.0 g (8.46 mmol) of 1-(2,6-diisopropylphenyl)-2-phenyl-1H-benzo[d]imidazole and 1.42 g (4.03 mmol) of iridium chloride trihydrate (IrCl 3 (H 2 O) n , n = 3) was mixed with 90 milliliters (mL) of 2-ethoxyethanol and 30 milliliters of deionized (DI) water, and then stirred for 24 hours while heating under reflux. The temperature was then lowered to room temperature. The resulting solid was separated by filtration and washed thoroughly with water, methanol and hexane in the stated order to obtain a solid. The obtained solid was dried in a vacuum oven to thereby obtain 3.1 g (82% yield) of compound 1A.

[0367] 1-(2,6-Diisopropylphenyl)-2-phenyl-1H-benzo[d]imidazole was synthesized according to the following reaction scheme.

[0368]

[0369] Synthesis of compound 1B

[0370] 3.1g (1.66mmol) compound 1A and 120mL dichloromethane are merged (DCM) to obtain a solution of compound 1A. 0.9g (3.50mmol) silver trifluoromethanesulfonate (AgOTf) is prepared with 40mL methanol (MeOH) as a separate solution, and the separate solution is added to the solution of compound 1A. Then, the resulting mixture is stirred at room temperature for 18 hours while blocking light with aluminum foil. The mixture is filtered through diatomite to remove the solid produced, and the solvent is removed under reduced pressure to obtain a solid (compound 1B), which is used in the next reaction without further purification.

[0371] Synthesis of compound 1

[0372] 2.7 g (2.43 mmol) of compound 1B and 1.31 g (2.43 mmol) of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole were mixed with 25 mL of 2-ethoxyethanol and 25 mL of dimethylformamide, followed by stirring at 120° C. for 24 hours. Then, the temperature was lowered to room temperature. The solvent was removed from the resulting mixture under reduced pressure to obtain a solid, which was purified by column chromatography (eluent: hexane and ethyl acetate) to thereby obtain 1.01 g (29% yield) of compound 1. The obtained compound was confirmed by high resolution mass spectrometry (HRMS (MALDI)) using matrix-assisted laser desorption ionization and high performance liquid chromatography (HPLC) analysis.

[0373] HRMS (MALDI): For C 88 H 80 D 3 Ir 6 Calculated value for O: m / z: 1435.6446; found: 1435.6443.

[0374] 1-(3,5-Diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme.

[0375]

[0376] Synthesis Example 2: Synthesis of Compound 5

[0377]

[0378] Synthesis of compound 5

[0379] 0.97 g (yield of 27%) of Compound 5 was obtained in a similar manner to that in Synthesis Example 1, except that 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(phenyl-d5)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was used instead of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0380] HRMS (MALDI): For C 93 H 80 D5 Ir 6 Calculated value for O: m / z: 1499.6728; found: 1499.6726.

[0381] 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(phenyl-d5)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme.

[0382]

[0383] Synthesis Example 3: Synthesis of Compound 11

[0384]

[0385] Synthesis of compound 11

[0386] 0.94 g (yield of 28%) of compound 11 was obtained in a similar manner to that in Synthesis Example 1, except that 1-(2,6-diisopropylphenyl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was used instead of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0387] HRMS (MALDI): For C 82 H 76 D 3 Ir 6 Calculated value for O: m / z: 1359.6133; found: 1359.6135.

[0388] 1-(2,6-Diisopropylphenyl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme.

[0389]

[0390] Synthesis Example 4: Synthesis of Compound 13

[0391]

[0392] Synthesis of compound 13

[0393] 0.89 g (yield of 27%) of compound 13 was obtained in a similar manner to that in Synthesis Example 1, except that 1-(2,6-diisopropylphenyl)-2-(6-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was used instead of 1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-2-(7-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0394] HRMS (MALDI): For C 82 H 76 D 3 Ir 6 Calculated value for O: m / z: 1359.6133; found: 1359.6131.

[0395] 1-(2,6-Diisopropylphenyl)-2-(6-(methyl-d3)dibenzo[b,d]furan-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme.

[0396]

[0397] Example 1

[0398] An ITO (as an anode) patterned glass substrate was cut into a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated in isopropyl alcohol and DI water for 5 minutes each, cleaned by irradiating ultraviolet light and exposing to ozone for 30 minutes, and then loaded on a vacuum deposition apparatus.

[0399] Compound HT3 and F12-P-dopant were vacuum co-deposited on the anode at a weight ratio of 98:2 to form a A hole injection layer having a thickness of , and compound HT3 is vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0400] Then, compound GH3 (host) and compound 1 (dopant) were vacuum co-deposited on the hole transport layer at a weight ratio of 92:8 to form a The thickness of the emission layer.

[0401] Next, compound ET3 and Liq-N-dopant were vacuum co-deposited on the emission layer at a volume ratio of 50:50 to form a An electron transport layer having a thickness of , Liq-N-dopant is vacuum deposited on the electron transport layer to form a An electron injection layer having a thickness of , and Al is vacuum deposited on the electron injection layer to form A cathode with a thickness of is provided, thereby completing the manufacture of the organic light-emitting device.

[0402]

[0403] Examples 2 to 4 and Comparative Examples 1 and 2

[0404] An organic light-emitting device was manufactured in a similar manner to that in Example 1, except that the compounds shown in Table 2 were used instead of Compound 1 when forming the emission layer.

[0405] Evaluation Example 1: Characterization of organic light-emitting devices

[0406] The driving voltage (volt, V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (nm), and lifetime (LT) of each of the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated. 97 , %), and the results are shown in Table 2. As evaluation equipment, a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A) were used. Lifespan (LT 97 ) (at 6,000 candela / m2 (cd / m 2 ) below) was evaluated as the time taken for the brightness to reach 97% relative to the initial brightness of 100%, and the life value was expressed as a relative value compared with Comparative Example 1.

[0407] Table 2

[0408]

[0409]

[0410] It is confirmed from Table 2 that the organic light emitting devices of Examples 1 to 4 each have a low driving voltage, a high maximum external quantum efficiency, and a long lifespan.

[0411] It is confirmed from Table 2 that, compared with the organic light emitting devices of Comparative Examples 1 and 2, the organic light emitting devices of Examples 1 to 4 have similar or lower driving voltage, similar or higher maximum external quantum efficiency, and improved lifespan.

[0412] According to one or more exemplary embodiments, the organometallic compound represented by Formula 1 has excellent electrical characteristics, and therefore, an electronic device such as an organic light-emitting device including at least one of the organometallic compounds represented by Formula 1 may have a low driving voltage, a high maximum external quantum efficiency, and a long lifespan. Therefore, by using the organometallic compound represented by Formula 1, a high-quality organic light-emitting device may be realized.

[0413] It should be understood that the exemplary embodiments described herein should be considered in a descriptive sense only and not for limiting purposes. The description of features or aspects in each exemplary embodiment should typically be considered to be applicable to other similar features or aspects in other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and detail may be made therein without departing from the spirit and scope as defined by the appended claims.

Claims

1. An organometallic compound represented by Formula 1: Formula 1 <h2 style=";text-align:left;direction:ltr">M1(L1)<h2 style=";text-align:left;direction:ltr"> n1 <h2 style=";text-align:left;direction:ltr"> (L2)<h2 style=";text-align:left;direction:ltr"> n2 in, In formula 1, M1 is a transition metal, L1 is a ligand represented by formula 1A, L2 is a ligand represented by Formula 1B, and n1 and n2 are each independently 1 or 2, Formula 1A Formula 1B Wherein, in Formula 1A and 1B, X1 is C or N, X2 is C or N, X3 is C or N, and X4 is C or N, Y1 is O, S or Se, Ring CY1 and ring CY3 are each independently a 5-membered heterocyclic group, 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a C1-C 30 a 5-membered heterocyclic group fused to a heterocyclic group, Ring CY2, ring CY4 and ring CY5 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, R1 to R4 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 heteroarylthio, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(═O)(Q8)(Q9), R5 is: hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, or substituted or unsubstituted C1-C 60 Alkylthio; cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, each unsubstituted or substituted by at least one of the following: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 )、-P(=O)(Q 38 )(Q 39 ), or a combination thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), T1 is: deuterium; C1-C 10 alkyl, cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl; or Each is deuterated and C1-C 10 alkyl-substituted cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, b1 to b5 and c1 are each independently an integer from 1 to 10, * and *' each represent the binding site with M1, Substituted C1-C 60 Alkyl, substituted C2-C 60 Alkenyl, substituted C2-C 60 Alkynyl, substituted C1-C 60 Alkoxy, substituted C1-C 60 Alkylthio, substituted C3-C 10 Cycloalkyl, substituted C1-C 10 Heterocycloalkyl, substituted C3-C 10 Cycloalkenyl, substituted C1-C 10 Heterocycloalkenyl, substituted C6-C 60 Aryl, substituted C7-C 60 Alkyl aryl, substituted C7-C 60 Arylalkyl, substituted C6-C 60 Aryloxy, substituted C6-C 60 Arylthio, substituted C1-C 60 Heteroaryl, substituted C2-C 60 Alkyl heteroaryl, substituted C2-C 60 Heteroarylalkyl, substituted C1-C 60 Heteroaryloxy, substituted C1-C 60 The substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are each independently: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(=O)(Q 18 )(Q 19 ), or a combination thereof; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group; C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic condensed heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, C1-C 60 Alkylthio, C3-C 10 Cycloalkyl, C1-C 10 Heterocycloalkyl, C3-C 10 Cycloalkenyl, C1-C 10 Heterocycloalkenyl, C6-C 60 Aryl, C7-C 60 Alkyl aryl, C7-C 60 Arylalkyl, C6-C 60 Aryloxy, C6-C 60 Arylthio, C1-C 60 Heteroaryl, C2-C 60 Alkyl heteroaryl, C2-C 60 Heteroarylalkyl, C1-C 60 Heteroaryloxy, C1-C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 )、 or -P(=O)(Q 38 )(Q 39 ), and Q1 to Q9, Q 11 To Q 19 , Q 21 To Q 29 , and Q 31 To Q 39 Each is independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C1-C 60 Alkyl, substituted or unsubstituted C2-C 60 Alkenyl, substituted or unsubstituted C2-C 60 Alkynyl, substituted or unsubstituted C1-C 60 Alkoxy, substituted or unsubstituted C1-C 60 Alkylthio, substituted or unsubstituted C3-C 10 Cycloalkyl, substituted or unsubstituted C1-C 10 Heterocycloalkyl, substituted or unsubstituted C3-C 10 Cycloalkenyl, substituted or unsubstituted C1-C 10 Heterocycloalkenyl, substituted or unsubstituted C6-C 60 Aryl, substituted or unsubstituted C7-C 60 Alkyl aryl, substituted or unsubstituted C7-C 60 Arylalkyl, substituted or unsubstituted C6-C 60 Aryloxy, substituted or unsubstituted C6-C 60 Arylthio, substituted or unsubstituted C1-C 60 Heteroaryl, substituted or unsubstituted C2-C 60 Alkyl heteroaryl, substituted or unsubstituted C2-C 60 Heteroarylalkyl, substituted or unsubstituted C1-C 60 Heteroaryloxy, substituted or unsubstituted C1-C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound according to claim 1, wherein M1 is iridium, and The sum of n1 and n2 is 3.

3. The organometallic compound according to claim 1, wherein ring CY1 and ring CY3 are each independently a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

4. The organometallic compound of claim 1 , wherein ring CY2, ring CY4 and ring CY5 are each independently a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound according to claim 1, wherein in Formula 1A The moiety represented by is a group represented by one of the formulae CY(1)-1 to CY(1)-3: in, In formulae CY(1)-1 to CY(1)-3, X 11 C(R 11a )、C(R 11a )(R 11b ), N, or N(R 11a ), X 12 C(R 12a )、C(R 12a )(R 12b ), N, or N(R 12a ), X 13 C(R 13a )、C(R 13a )(R 13b ), N, or N(R 13a ), Cyclo 10 C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, R 10 , R 11a , R 11b , R 12a , R 12b , R 13a , and R 13b Each independently as defined in claim 1 for R1, b10 is an integer from 1 to 10, represents a single bond or a double bond, * indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

6. The organometallic compound according to claim 1, wherein in Formula 1A The moiety represented by is a group represented by one of the formulae CY(2)-1 to CY(2)-16: in, In formulae CY(2)-1 to CY(2)-16, R 21 To R 24 Each independently as defined in claim 1 for R2, provided that R 21 To R 24 Not hydrogen, *' indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

7. The organometallic compound of claim 1, wherein L1 is a ligand represented by formula 1A-1 or 1A-2: in, In Formulas 1A-1 and 1A-2, R 10 To R 13 Each independently as defined in claim 1 for R1, R2 as described in claim 1, c2 and c10 are each independently an integer from 1 to 4, and * and *' each indicate a binding site to M1.

8. The organometallic compound as claimed in claim 1, wherein in Formula 1B The moiety represented by is a group represented by one of the formulae CY(3)-1 to CY(3)-3: in, In formulae CY(3)-1 to CY(3)-3, X 31 C(R 31a )、C(R 31a )(R 31b ), N, or N(R 31a ), X 32 C(R 32a )、C(R 32a )(R 32b ), N, or N(R 32a ), X 33 C(R 33a )、C(R 33a )(R 33b ), N, or N(R 33a ), Cyclo 30 C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, R 30 , R 31a , R 31b , R 32a , R 32b , R 33a , and R 33b Each independently as defined for R3 in claim 1, b30 is an integer from 1 to 10, represents a single bond or a double bond, * indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

9. The organometallic compound as claimed in claim 1, wherein in Formula 1B The moiety represented by is a group represented by one of the formulae CY(4)-1 to CY(4)-6: in, In formulae CY(4)-1 to CY(4)-6, X4, Y1, R4, and R5 are each independently as described in claim 1, T 11 To T 16 Each independently as defined in claim 1 for T1, R 41 and R 42 Each independently as defined in claim 1 for R4, b41 is 1 or 2, b51 is an integer from 1 to 4, b52 is an integer from 1 to 3, *' indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

10. The organometallic compound of claim 1, wherein L2 is a ligand represented by formula 1B-1 or 1B-2: in, In Formulas 1B-1 and 1B-2, X4, Y1, R4, R5, and T1 are each as described in claim 1, R 30 To R 33 Each independently as defined in claim 1 for R3, c4 is 1 or 2, c3 and c5 are each independently an integer from 1 to 4, c10 is an integer from 1 to 6, and * and *' each indicate a binding site to M1.

11. The organometallic compound of claim 1, wherein R1 to R4 are each independently: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio; C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof; Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl; cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl , oxadiazolyl, triazine, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridyl, or imidazopyrimidyl: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, C1-C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthrenyl, anthracenyl, fluoranthenyl, benzo[9,10]phenanthrenyl, pyrenyl, yl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, benzoquinolyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, benzisothiazolyl, benzoxazolyl, benzisoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazine, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and Q1 to Q9 are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof.

12. The organometallic compound of claim 1, wherein R5 is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio; C1-C 20 Alkyl, C1-C 20 Alkoxy, or C1-C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, C1-C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof; cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridinyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl; cyclopentyl, cyclohexyl, phenyl, naphthyl, pyrrolyl, thienyl, furanyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolyl, isoquinolyl, triazolyl, tetrazolyl, oxadiazolyl, or triazinyl, each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid group or salt thereof, C1-C 10 Alkyl, or a combination thereof; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), -N(Q4)(Q5), -B(Q6)(Q7), -P(Q8)(Q9), or -P(=O)(Q8)(Q9), and Q1 to Q9 are each independently: -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl, each substituted with at least one of: deuterium, C1-C 10 Alkyl, phenyl, or a combination thereof.

13. The organometallic compound according to claim 1, wherein T1 is: -CD3, -CD2H, or -CDH2; or A group represented by one of formulae 8-1 to 8-14: in, In formulas 8-1 to 8-14, *Indicates the binding site with the adjacent atom. The organometallic compound according to claim 1 , wherein c1 is 1 or 2. 14 .

15. The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 60:

16. Organic light-emitting device, comprising: a first electrode; a second electrode; as well as an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and The organic layer comprises at least one of the organic metal compounds as described in any one of claims 1 to 15.

17. The organic light emitting device of claim 16, wherein the emissive layer comprises the at least one of the organometallic compounds. 18 . The organic light emitting device of claim 16 , wherein the emission layer emits green light having a maximum emission wavelength of 490 nm to 550 nm.

19. The organic light emitting device according to claim 16, wherein The first electrode is an anode, The second electrode is a cathode, and The organic layer further comprises: 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, wherein the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

20. An electronic device comprising the organic light emitting device according to any one of claims 16 to 19.

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