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; x11 is C (R11) or N; x12 is C (R12) or N; x13 is C (R13) or N; ring CY1 and ring CY2 are each independently a C5-C30 carbocyclic group or a C1-C30 heterocyclic group; ring CY2 is a fused ring in which at least two rings are fused to each other; a2 is an integer from 1 to 10; b1 and b2 are each independently an integer from 1 to 10; * and * 'each represent a binding site to M1; and the remaining groups 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. 10-2023-0150289 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] An organic light emitting device (OLED) is a self-emitting device having excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, response speed, etc. In addition, an OLED can produce full-color images.

[0005] A typical organic light-emitting device 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. When the excitons transition from an excited state to a ground state, light is emitted. 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 is C or N, and X 2 is C or N,

[0022] X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, and X 13 C(R 13 ) or N,

[0023] Cyclo 1 and CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0024] Cyclo 2 is a fused ring in which at least two rings are fused to each other,

[0025] R 1 , R 2 , R 11 -R 13 , and R 31 -R 33 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 C1 -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] T 2 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 ),

[0027] Multiple R 1 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0028] Multiple R 2 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0029] R 1 and R 11 -R 13 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0030] a2 is an integer from 1 to 10,

[0031] b1 and b2 are each independently an integer of 1-10,

[0032] * and *' respectively represent 1 The binding site

[0033] 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 -C10 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 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are:

[0034] 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;

[0035] Each of the following C 1 -C 60 Alkyl, C 2 -C 60Alkenyl, 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;

[0036] C3 -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;

[0037] 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 , -CF2 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 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

[0038] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 28 )(Q 29 ), or -P(=O)(Q 38 )(Q 39 ),and

[0039] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -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 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C1 -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.

[0040] 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, wherein the organic layer includes at least one organic metal compound represented by Formula 1.

[0041] The organic metal compound represented by Formula 1 may be included in the 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

[0042] The above and other aspects, features, and advantages of some exemplary embodiments of the present disclosure will become more apparent from the following detailed description considered in conjunction with the accompanying drawings, in which:

[0043] Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0044] 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 this 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.

[0045] 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 "the (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.

[0046] 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.

[0047] 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, for example, caused by 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.

[0048] 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.

[0049] 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.

[0050] 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 ±5%, relative to the stated value.

[0051] 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".

[0052] The organometallic compound according to one aspect is represented by Formula 1:

[0053] Formula 1

[0054] M 1 (L 1 ) n1 (L 2 ) n2

[0055] Where M in Formula 1 1 For transition metals.

[0056] 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.

[0057] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0058] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).

[0059] In one or more embodiments, M 1 It may be iridium (Ir).

[0060] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0061] In one or more embodiments, the sum of n1 and n2 may be 2 or 3.

[0062] In one or more embodiments, M 1 It may be iridium (Ir), and the sum of n1 and n2 may be 3. For example, M 1 It may be iridium (Ir), n1 may be 2, and n2 may be 1.

[0063] In one or more embodiments, M 1 It may be platinum (Pt), and the sum of n1 and n2 may be 2.

[0064] L in Formula 1 1 is a ligand represented by Formula 1A:

[0065] Formula 1A

[0066]

[0067] Wherein, in Formula 1A, X 1 is C or N, and X 2 It is C or N.

[0068] In one or more embodiments, X 1 Can be N, and X 2 Can be C.

[0069] In Formula 1A, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, and X 13 C(R 13 ) or N.

[0070] In one or more embodiments, X 11 Can be C(R 11 ), X 12 Can be C(R 12 ), and X 13 Can be C(R 13 ).

[0071] Ring CY in Formula 1A 1 and CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0072] Ring CY in Formula 1A 2 is a fused ring in which at least two rings are fused to each other. For example, in some embodiments, ring CY 2 Can be C 8 -C 30 Carbocyclic group or C3 -C 30 Heterocyclic group.

[0073] In one or more embodiments, CY 1 It 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.

[0074] In one or more embodiments, CY 2 It may be a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene 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,

[0076] Cyclo 1 may be a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and

[0077] Cyclo 2 It may be a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group.

[0078] R 1 , R 2 , and R 11 -R 13 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 60Alkoxy, 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 ), where Q 1 -Q 9 As defined herein.

[0079] T in Formula 1A 2Deuterium, -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(Q4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ). In Formula 1A, T 2 The number a2 is an integer from 1 to 10.

[0080] 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)-3:

[0081]

[0082] Wherein, in formulas CY(2)-1 to CY(2)-3,

[0083] X 2 As described in this article,

[0084] X 21 Can be C(R 21 ) or N, X 22 Can be C(R 22 ) or N, X 23 Can be C(R 23 ) or N, and X 24 Can be C(R 24 ) or N,

[0085] X 25 Can be C(R 25 ) or N, X 26 Can be C(R 26 ) or N, X 27 Can be C(R 27 ) or N, and X 28 Can be C(R 28 ) or N,

[0086] R 21 -R 28 can be independently as described herein for R 2 As defined,

[0087] R 21 -R 28 At least one of them cannot be hydrogen,

[0088] R 21 -R 28 Two or more adjacent groups of 5 -C30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0089] Substituted C 5 -C 30 Carbocyclic groups and substituted C 1 -C 30 The substituents of the heterocyclic group may each be as described herein,

[0090] *' indicates that the 1 The binding site, and

[0091] *” indicates the binding site with the adjacent atoms.

[0092] In one or more embodiments, R in formula CY(2)-1 to CY(2)-3 21 -R 28 At least one of them can be independently deuterated, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, or substituted or unsubstituted C 1 -C 60 For example, the substituted or unsubstituted C 1 -C 60 The alkyl group may be unsubstituted or substituted by at least one of the following: 1 -C 20 Alkyl: deuterium, -F, -Cl, -Br, -I, -SF 5 , cyano, nitro, or a combination thereof. 1 -C 20 The alkyl group may be a straight chain C 1 -C 20 (For example, C 1 -C 10 ) alkyl or branched C 3 -C 20 (For example, C 3 -C 10 )alkyl.

[0093] For example, R 21 and R 22 At least one (i.e., R 21 , R 22 , or R 21 and R 22Both) may be each independently unsubstituted or substituted by at least one of the following C 1 -C 20 Alkyl: deuterium, -F, -Cl, -Br, -I, -SF 5 , cyano, nitro, or a combination thereof. 1 -C 20 The alkyl group may be a straight chain C 1 -C 20 (For example, C 1 -C 10 ) alkyl or branched C 3 -C 20 (For example, C 3 -C 10 )alkyl.

[0094] In one or more embodiments, L 1 It may be a ligand represented by Formula 1A-1:

[0095] Formula 1A-1

[0096]

[0097] Wherein, in Formula 1A-1,

[0098] X 1 , X 11 -X 13 , and R 2 may each be as described herein,

[0099] X 14 Can be C(R 14 ) or N, X 15 Can be C(R 15 ) or N, X 16 Can be C(R 16 ) or N, and X 17 Can be C(R 17 ) or N,

[0100] R 14 -R 17 can be independently as described herein for R 1 As defined,

[0101] T 21 and T 22 can be independently as described herein for T 2 As defined,

[0102] a21 can be 0, 1, or 2,

[0103] a22 can be an integer from 0 to 4.

[0104] The sum of a21 and a22 can be 1 or greater.

[0105] b20 may be an integer from 1 to 6 (e.g., an integer from 1 to 5),

[0106] The sum of a21, a22, and b20 is 6, and

[0107] * and *' respectively represent 1 binding site.

[0108] In one or more embodiments, a21 in Formula 1A-1 may be 1 or 2.

[0109] L in Formula 1 2 is a ligand represented by Formula 1B:

[0110] Formula 1B

[0111]

[0112] Where R 31 -R 33 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 60Aryloxy, 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 ), where Q 1 -Q 9 As defined herein.

[0113] In one or more embodiments, R in Formula 1A and 1B 1 , R 2 , R 11 -R 13 , and R 31 -R 33 Can be independently:

[0114] 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 C1 -C 20 Alkylthio;

[0115] 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;

[0116] 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;

[0117] 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 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

[0118] -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(Q8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ),and

[0119] Q 1 -Q 9 Can be independently:

[0120] -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 ;

[0121] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0122] 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.

[0123] In one or more embodiments, T 2 Can be independently:

[0124] 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 (e.g., straight chain C 1 -C 20 Alkyl or branched C 3 -C 20 Alkyl), C 1 -C 20 Alkoxy (e.g., straight chain C 1 -C 20 Alkoxy or branched C 3 -C 20 Alkoxy), or C 1 -C 20 Alkylthio (e.g., straight chain C 1 -C 20 Alkylthio or branched C 3 -C 20 alkylthio);

[0125] Each of the following C 1 -C 20 Alkyl (e.g., straight chain C 1 -C 20 Alkyl or branched C 3 -C 20 Alkyl), C 1 -C 20 Alkoxy (e.g., straight chain C 1 -C 20 Alkoxy or branched C 3 -C 20 Alkoxy), or C 1 -C 20 Alkylthio (e.g., straight chain C 1 -C 20 Alkylthio or branched C 3 -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 10Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or a combination thereof;

[0126] 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;

[0127] 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 -C20 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

[0128] -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

[0129] Q 1 -Q 9 Can be independently:

[0130] -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 ;

[0131] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0132] 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.

[0133] In one or more embodiments, R in Formula 1A and 1B 1 , R 2 , R 11 -R 13 , and R 31 -R 33 Can be independently:

[0134] 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;

[0135] 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 10-350; or

[0136] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5),and

[0137] T 2 Can be:

[0138] 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;

[0139] 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 10-350; or

[0140] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5 ),

[0141] Q 1 -Q 5 As defined in this article:

[0142]

[0143]

[0144]

[0145]

[0146]

[0147]

[0148]

[0149]

[0150]

[0151]

[0152] 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.

[0153] In one or more embodiments, the number of R is b1 1 At least one of may not be hydrogen. For example, the number of R 1 At least one of may be deuterium, -F, -Cl, -Br, -I, -SF 5 , cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 6 -C 60 Aryl, -Si(Q 1 )(Q 2 )(Q 3 ), or -Ge(Q 1 )(Q 2 )(Q 3 ).

[0154] In one or more embodiments, T 2 Can be deuterium, -F, -Cl, -Br, -I, -SF 5 , cyano, nitro, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 3 -C 10 Cycloalkyl, or substituted or unsubstituted C 6 -C 60 Aryl.

[0155] In one or more embodiments, R 31 and R 32 may be independently substituted or unsubstituted C 1 -C 60 alkyl.

[0156] In one or more embodiments, R 33 It can be hydrogen or deuterium.

[0157] The multiple R in Formula 1A 1 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0158] The multiple R in Formula 1A 2 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0159] R with quantity b1 1 and R 11 -R 13 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0160] a2 in Formula 1A is an integer of 1-10.

[0161] b1 and b2 in Formula 1A are each independently an integer of 1-10.

[0162] The * and *' in Formula 1A and 1B each represent the same 1 binding site.

[0163] In one or more embodiments, the organometallic compound may be represented by one of Formulas 5-1 to 5-3:

[0164]

[0165]

[0166] Among them, in formulas 5-1 to 5-3,

[0167] M 1 、n1、n2、X 1 , X 2 , R 11 -R 13 , and R 31 -R 33 may each be as described herein,

[0168] R 14 -R 17can be independently as described herein for R 1 As defined,

[0169] R 21 -R 28 can be independently as described herein for R 2 As defined,

[0170] R in Formula 5-1 21 , R 22 , and R 25 -R 28 At least one of them cannot be hydrogen,

[0171] R in Formula 5-2 21 and R 24 -R 28 At least one of cannot be hydrogen, and

[0172] R in Formula 5-3 23 -R 28 At least one of the may not be hydrogen.

[0173] In formulas 5-1 to 5-3, R 14 -R 17 At least one (e.g., R 17 ) may not be hydrogen.

[0174] In one or more embodiments, the organometallic compound may be represented by one of Compounds 1 to 83:

[0175]

[0176]

[0177]

[0178]

[0179]

[0180]

[0181] In one or more embodiments, the organometallic compound represented by Formula 1 may be electrically neutral.

[0182] The organometallic compound represented by Formula 1 includes ligands represented by Formulas 1A and 1B, wherein Formula 1A includes a ligand and a ring CY 1 A fused N-containing heterocycle, and further comprising a ring CY having a fused ring structure 2, and the condensed ring structure includes a substituent other than hydrogen. Due to this structure, the organometallic compound represented by Formula 1 may have excellent luminescent properties and may have properties suitable for use as a luminescent material with high color purity by controlling the emission wavelength range and half width (FWHM).

[0183] Therefore, an electronic device including the organometallic compound represented by Formula 1, for example, an organic light emitting device, may have a low driving voltage, a high maximum external quantum efficiency, and / or a low roll-off ratio.

[0184] 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 lowest excited singlet energy level (S) of some of the organometallic compounds represented by Formula 1 under the condition that the molecular structure was optimized at the B3LYP level. 1 ), and the lowest excited triplet state (T 1 ) energy levels, and the results are shown in Table 1. The energy levels are expressed in electron volts (eV).

[0185] Table 1

[0186]

[0187]

[0188] As confirmed by Table 1, the organometallic compound represented by Formula 1 has electrical characteristics suitable for use as a dopant for electronic devices such as an organic light emitting device (OLED).

[0189] In one or more embodiments, the maximum emission wavelength (peak emission peak 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 590 nanometers (nm) to about 680 nm, from about 600 nm to about 675 nm, or from about 610 nm to about 670 nm.

[0190] 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.

[0191] The organometallic compound represented by Formula 1 is 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 organometallic compound represented by Formula 1.

[0192] By including an organic layer 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 / or excellent lifespan characteristics.

[0193] The organic metal compound represented by Formula 1 may be used between an electrode pair of an organic light-emitting device. For example, at least one of the organic metal compounds represented by Formula 1 may be included in the emission layer. In this regard, the organic metal compound 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.

[0194] In one or more embodiments, the emitting layer may emit red light. For example, the emitting layer may emit red light having a maximum emission wavelength of about 590 nm to about 680 nm, about 600 nm to about 675 nm, or about 610 nm to about 670 nm.

[0195] 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 of Formula 1 or at least two different organometallic compounds of Formula 1”.

[0196] 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).

[0197] 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.

[0198] For example, in the organic light-emitting device, the first electrode may be an anode, and the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode, and 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.

[0199] The term "organic layer" as used herein refers to a single layer or a plurality of layers located between a first electrode and a 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.

[0200] 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.

[0201] A substrate may be further provided under the first electrode 11 or on the second electrode 19. The substrate may be a substrate generally used in an organic light-emitting device, for example, a glass substrate or a transparent plastic substrate having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and / or waterproofness.

[0202] 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).

[0203] The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more 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.

[0204] The organic layer 15 may be disposed on the first electrode 11 .

[0205] The organic layer 15 may include an emission layer, and may further include a hole transport region and an electron transport region.

[0206] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0207] 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.

[0208] 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 have 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.

[0209] 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.

[0210] 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.

[0211] When the hole injection layer is formed by spin coating, coating conditions may vary depending on 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.

[0212] 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.

[0213] 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′-cyclohexylidenebis[N,N-bis(4-methylphenyl)aniline] (TAPC), 4,4′-bis[N,N′-(3-tolyl)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:

[0214]

[0215]

[0216] Formula 201

[0217]

[0218] Formula 202

[0219]

[0220] Ar in Formula 201 101 and Ar 102 Can be independently:

[0221] 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

[0222] 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 -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 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or a combination thereof.

[0223] Xa and xb in Formula 201 may each independently be an integer of 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.

[0224] R in formula 201 and 202 101-R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0225] 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;

[0226] Each of the following C 1 -C 10 Alkyl or C 1 -C 10 Alkoxy: 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;

[0227] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0228] 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.

[0229] R in Formula 201 109 Can be:

[0230] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0231] 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.

[0232] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0233] Formula 201A

[0234]

[0235] R in Formula 201A 101 , R 111 , R 112 , and R 109 Each may be as described herein.

[0236] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include, but are not limited to, one or more of compounds HT1 to HT20:

[0237]

[0238]

[0239] The thickness of the hole transport region may be about 100 angstroms. to about For example, about 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, about to about The thickness of the hole transport layer may be about to about For example, about 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.

[0240] In addition to the materials described above, 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.

[0241] The charge generating material may be, for example, a p-dopant. The p-dopant may be, but is not limited to, a quinone derivative, a metal oxide, or one of a compound containing a cyano group. For example, 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 embodiments are not limited thereto:

[0242]

[0243] The hole transport region may include a buffer layer.

[0244] The buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer and thus improve efficiency.

[0245] 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 to form the electron blocking layer may be mCP described below.

[0246] The 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 be substantially 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.

[0247] 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.

[0248] 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, compound H51, or compound RH3, but embodiments are not limited thereto:

[0249]

[0250]

[0251] In one or more embodiments, the host may include a compound represented by Formula 301:

[0252] Formula 301

[0253]

[0254] Ar in formula 301 111 and Ar 112 Can be independently:

[0255] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0256] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0257] Ar in Formula 301 113 -Ar 116 Can be independently:

[0258] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0259] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0260] g, h, i, and j in Formula 301 may each independently be an integer of 0-4, and may be, for example, 0, 1, or 2.

[0261] Ar in Formula 301 113 -Ar 116 Can be independently:

[0262] C substituted with at least one of the following 1 -C 10 Alkyl: phenyl, naphthyl, anthracenyl, or a combination thereof;

[0263] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0264] 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

[0265] The following groups:

[0266]

[0267] However, the implementation mode is not limited thereto.

[0268] In one or more embodiments, the host may include a compound represented by Formula 302:

[0269] Formula 302

[0270]

[0271] Ar in formula 302 122 -Ar 125 and Ar in Formula 301 113 Defined similarly,

[0272] Ar in formula 302 126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, propyl, etc.).

[0273] In formula 302, k and l may each independently be an integer of 0 to 4. For example, k and l may each independently be 0, 1, or 2.

[0274] When the organic light emitting device 10 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 variations such as emission of white light are possible.

[0275] When the emission layer includes a host and a dopant, the 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.

[0276] The thickness of the emission layer may be about to about For example to about When the thickness of the emission layer 15 is within these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0277] Next, an electron transport region may be disposed on the emissive layer.

[0278] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0279] 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.

[0280] 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.

[0281] 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:

[0282]

[0283] The thickness of the hole blocking layer may be about to about For example, about 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.

[0284] 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:

[0285]

[0286] 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:

[0287]

[0288]

[0289]

[0290] The thickness of the electron transport layer may be about to about For example, about 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.

[0291] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0292] 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:

[0293]

[0294] The electron transport region may include an electron injection layer that facilitates injection of electrons from the second electrode 19 .

[0295] The electron injection layer may include LiQ, LiF, NaCl, CsF, Li 2O, BaO, or a combination thereof.

[0296] The thickness of the electron injection layer may be about to about For example, about 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.

[0297] 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.

[0298] Already referred to Figure 1 The organic light emitting device is described, but embodiments are not limited thereto.

[0299] According to one or more embodiments, the diagnostic composition includes at least one organometallic compound represented by Formula 1.

[0300] The organometallic compound represented by Formula 1 may provide high luminescence efficiency, and thus, a diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have high diagnostic efficiency.

[0301] The diagnostic composition can be used in various applications including diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0302] 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, etc. 1 -C 60 The alkyl group may be C 1 -C 20 Alkyl, C 1 -C 10 Alkyl, C 1 -C 6 Alkyl, C 1 -C 5 Alkyl, or C 1 -C3 Each of the alkyl groups may be straight chain or branched. In the case of a branched alkyl group, the lower limit of the carbon number range of each of the above alkyl groups is 3. 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.

[0303] 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.

[0304] 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.

[0305] 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.

[0306] As used herein, the term "C 3 -C 10"Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms as ring atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, etc. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0307] 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, and 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.

[0308] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms as ring atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, etc. 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.

[0309] As used herein, the term "C 1 -C 10 The term "heterocycloalkenyl" 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.

[0310] As used herein, the term "C6 -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 ring 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.

[0311] 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.

[0312] 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 atom and 1 to 60 carbon atoms as ring 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 60 When the heteroarylene groups each include two or more rings, the rings may be fused to each other.

[0313] 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.

[0314] 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).

[0315] 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).

[0316] The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8-60 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.

[0317] The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 1-60 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.

[0318] 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.

[0319] 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 and at least one heteroatom selected from B, N, O, P, Si, S, Se, and Ge as ring atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0320] 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 -C 60 Aryl, substituted C 7 -C60 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:

[0321] 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;

[0322] 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 、-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 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;

[0323] 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 -C60 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;

[0324] 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, C 2 -C 60 Alkynyl, C1 -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

[0325] -Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q37 )、-P(Q 38 )(Q 39 ), or -P(=O)(Q 38 )(Q 39 ),and

[0326] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -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 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 1 -C 60Heteroaryloxy, 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.

[0327] For example, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -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 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, C 1 -C 60 Heteroaryloxy, C 1 -C 60Heteroarylthio 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.

[0328] Hereinafter, the organometallic compound represented by Formula 1 and the organic light-emitting device according to one or more 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.

[0329] Example

[0330] Synthesis Example 1: Synthesis of Compound 2

[0331]

[0332] Synthesis of intermediate L2

[0333] 1.2 grams (g) (5.26 millimoles (mmol)) of 4-chloro-7-methylbenzo[c][2,7]naphthyridine was mixed with 80 milliliters (mL) of tetrahydrofuran (THF) and 20 mL of deionized (DI) water, and then 1.8 g (5.79 mmol) of 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane, 0.3 g (0.26 mmol) of tetrakis(triphenylphosphine)palladium(0)(Pd(PPh 3 ) 4 ), and 1.8 g (13.1 mmol) K 2 CO 3 The mixture was then heated under reflux overnight and subsequently cooled to room temperature. The organic layer obtained by extraction by adding ethyl acetate and water to the resulting solution was dried using magnesium sulfate. The solvent was then removed under reduced pressure and the product was purified by liquid chromatography (LC) to thereby obtain 1.5 g (76% yield) of intermediate L2.

[0334] Liquid chromatography-mass spectrometry (LC-MS): m / z=377 (M+H) + .

[0335] Synthesis of L2 Dimer

[0336] 1.0g (2.6mmol) intermediate L2 and 0.44g (1.3mmol) iridium chloride trihydrate are mixed with 60mL 2-ethoxyethanol and 15mL DI water, then heated under reflux for 24 hours.The temperature of the gained mixture is reduced to room temperature, and the solid produced is filtered, and then fully washed with water / methanol / hexane in the order stated.Described solid is dried in vacuum drying oven to obtain 0.9gL2 Dimer thus.L2 Dimer is used in the next reaction when there is no extra purification process.

[0337] Synthesis of compound 2

[0338] 0.9 g (0.46 mmol) of L2 Dimer, 0.24 g (2.3 mmol) of acetylacetone, and 0.24 g (2.3 mmol) of Na 2 CO 3 It was mixed with 50 mL of 2-ethoxyethanol, followed by stirring at 100° C. for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, and the resulting solid was filtered and purified by liquid chromatography to thereby obtain 0.4 g (40% yield) of Compound 1.

[0339] LC-MS: m / z=1043 (M+H) + .

[0340] Synthesis Example 2: Synthesis of Compound 9

[0341]

[0342] Synthesis of intermediate L9

[0343] 1.5 g (75% yield) of intermediate L9 was synthesized using a method similar to the method used to synthesize intermediate L2 in Synthesis Example 1, except that 4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)naphthalen-2-yl)-1,3,2-dioxaborolane was used instead of 2-(4-(tert-butyl)naphthalen-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane.

[0344] LC-MS: m / z=389 (M+H) + .

[0345] Synthesis of L9 Dimer

[0346] L9 Dimer was synthesized using a method similar to that used to synthesize L2 Dimer of Synthesis Example 1, except that Intermediate L9 was used instead of Intermediate L2.

[0347] Synthesis of compound 9

[0348] 0.3 g (35% yield) of Compound 9 was synthesized using a method similar to that used to synthesize Compound 2 of Synthesis Example 1, except that L9 Dimer was used instead of L2 Dimer.

[0349] LC-MS: m / z=1067 (M+H) + .

[0350] Synthesis Example 3: Synthesis of Compound 15

[0351]

[0352] Synthesis of intermediate L15

[0353] 1.0 g (4.29 mmol) of 4-chloro-7-fluorobenzo[c][2,7]naphthyridine was mixed with 60 mL of THF and 15 mL of DI water, and then 1.6 g (5.15 mmol) of 4,4,5,5-tetramethyl-2-(4-(trifluoromethyl)naphthalen-2-yl)-1,3,2-dioxaborolane, 0.07 g (0.3 mmol) of palladium(II) acetate (Pd(OAc)) were added thereto. 2 ), 0.25 g (0.6 mmol) 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos), and 1.5 g (10.7 mmol) K 2 CO 3 The reaction mixture was then heated under reflux overnight and subsequently cooled to room temperature. The organic layer obtained by extraction by adding ethyl acetate and water to the resulting solution was dried using magnesium sulfate. The solvent was then removed under reduced pressure and the product was subsequently purified by liquid chromatography to thereby obtain 1.1 g (70% yield) of intermediate L15.

[0354] LC-MS: m / z=393 (M+H) + .

[0355] Synthesis of L15 Dimer

[0356] L15 Dimer was synthesized using a method similar to that used to synthesize L2 Dimer of Synthesis Example 1, except that Intermediate L15 was used instead of Intermediate L2.

[0357] Synthesis of compound 15

[0358] 0.3 g (36% yield) of Compound 15 was synthesized using a method similar to that used to synthesize Compound 2 in Synthesis Example 1, except that L15 Dimer was used instead of L2 Dimer.

[0359] LC-MS: m / z=1075 (M+H) + .

[0360] Synthesis Example 4: Synthesis of Compound 23

[0361]

[0362] Synthesis of intermediate L23

[0363] 1.0 g (73% yield) of intermediate L23 was synthesized using a method similar to that used to synthesize intermediate L9 of Synthesis Example 2, except that 4-chloro-7-(4-fluorophenyl)benzo[c][2,7]naphthyridine was used instead of 4-chloro-7-methylbenzo[c][2,7]naphthyridine.

[0364] LC-MS: m / z=469 (M+H) + .

[0365] Synthesis of L23 Dimer

[0366] L23 Dimer was synthesized using a method similar to that used to synthesize L2 Dimer of Synthesis Example 1, except that Intermediate L23 was used instead of Intermediate L2.

[0367] Synthesis of compound 23

[0368] 0.2 g (30% yield) of Compound 23 was synthesized using a method similar to that used to synthesize Compound 2 of Synthesis Example 1, except that L23 Dimer was used instead of L2 Dimer.

[0369] LC-MS: m / z=1227 (M+H) + .

[0370] Example 1

[0371] 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 mounted on a vacuum deposition apparatus.

[0372] Compound HT3 and F12-P-dopant were co-deposited on the anode in a weight ratio of 98:2 by vacuum 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 .

[0373] Subsequently, compound RH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer at a weight ratio of 97:3 by vacuum deposition to form a The thickness of the emission layer.

[0374] Then, the compound ETL and the Liq-N-dopant were co-deposited on the emission layer in a volume ratio of 50:50 by vacuum deposition to form a An electron transport layer having a thickness of , and a 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.

[0375]

[0376] Examples 2 to 4 and Comparative Examples 1 and 2

[0377] 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.

[0378] Evaluation Example 1: Characterization of organic light-emitting devices

[0379] The driving voltage (V), maximum external quantum efficiency (Max EQE, %), maximum emission wavelength (λ) of the organic light-emitting devices of Examples 1 to 4 and Comparative Examples 1 and 2 were evaluated. max , nm), half width (FWHM, nm), and roll-off ratio (%), 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. The roll-off ratio was calculated according to Equation 20.

[0380] Equation 20

[0381] Roll-off ratio = {1-(emission efficiency (at 3500 nits) / maximum emission efficiency)}×100% Table 2

[0382]

[0383]

[0384]

[0385] As confirmed by Table 2, the organic light emitting devices of Examples 1 to 4 each have a low driving voltage, a high maximum external quantum efficiency, a narrow FWHM, and a low roll-off ratio.

[0386] It was also confirmed that, compared with the organic light emitting devices of Comparative Examples 1 and 2, the organic light emitting devices of Examples 1 to 4 had comparable or lower driving voltage, comparable or narrower FWHM, comparable or superior maximum external quantum efficiency, and lower roll-off ratio.

[0387] 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 using at least one of the organometallic compounds represented by Formula 1 may have a low driving voltage, a high maximum external quantum efficiency, a narrow FWHM, and a low roll-off ratio. Therefore, by using at least one of the organometallic compounds represented by Formula 1, a high-quality organic light-emitting device may be realized.

[0388] 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, and X2 is C or N, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, and X 13 C(R 13 ) or N, Ring CY1 and ring CY2 are each independently C5-C 30 Carbocyclic group or C1-C 30 Heterocyclic groups, Ring CY2 is a fused ring in which at least two rings are fused to each other, R1, R2, R 11 -R 13 , and R 31 -R 33 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 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), T2 is 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 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), Two or more adjacent R1 groups are optionally bonded to each other to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Two or more adjacent R2 groups are optionally bonded to each other to form a substituted or unsubstituted C5-C 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, R1 and R 11 -R 13 Two or more adjacent groups of 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, a2 is an integer from 1 to 10, b1 and b2 are each independently an integer of 1-10, * and *' each represent the binding site with M1, Substituted C5-C 30 Carbocyclic groups, substituted C1-C 30 Heterocyclic groups, 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 Substituents of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group are: 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-Q9, Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -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 as claimed in claim 1, wherein X1 is N, and X2 is C.

4. The organometallic compound of claim 1 , wherein the ring CY1 is 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 of claim 1 , wherein the ring CY2 is a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene 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.

6. The organometallic compound according to claim 1, wherein Ring CY1 is a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and Ring CY2 is a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, or a phenanthroline group.

7. 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)-3: in, In formulae CY(2)-1 to CY(2)-3, X2 As described in claim 1, X 21 C(R 21 ) or N, X 22 C(R 22 ) or N, X 23 C(R 23 ) or N, and X 24 C(R 24 ) or N, X 25 C(R 25 ) or N, X 26 C(R 26 ) or N, X 27 C(R 27 ) or N, and X 28 C(R 28 ) or N, R 21 -R 28 Each independently as defined in claim 1 for R2, R 21 -R 28 At least one of is not hydrogen, R 21 -R 28 Two or more adjacent groups of 30 Carbocyclic group or substituted or unsubstituted C1-C 30 Heterocyclic groups, Substituted C5-C 30 Carbocyclic groups and substituted C1-C 30 The substituents of the heterocyclic group are each as described in claim 1, *' indicates the binding site with M1, and *” indicates the binding site with the adjacent atoms.

8. The organometallic compound of claim 1, wherein L1 is a ligand represented by formula 1A-1: Formula 1A-1 in, In Formula 1A-1, X1, X 11 -X 13 , and R2 are each as described in claim 1, X 14 C(R 14 ) or N, X 15 C(R 15 ) or N, X 16 C(R 16 ) or N, and X 17 C(R 17 ) or N, R 14 -R 17 Each independently as defined in claim 1 for R1, T 21 and T 22 Each independently as defined in claim 1 for T2, a21 is 0, 1, or 2, a22 is an integer from 0 to 4. The sum of a21 and a22 is 1 or greater, b20 is an integer from 1 to 5, and * and *' each indicate a binding site to M1.

9. The organometallic compound according to claim 8, wherein a21 is 1 or 2.

10. The organometallic compound according to claim 1, wherein R1, R2, R 11 -R 13 , and R 31 -R 33 Each independently 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, 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-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.

11. The organometallic compound according to claim 1, wherein R1, R2, R 11 -R 13 , and R 31 -R 33 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; 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 10-350; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -N(Q4)(Q5), and T2 is: Deuterium, -F, -Cl, -Br, -I, -SF5, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C1-C 60 Alkyl, C2-C 60 Alkenyl, C2-C 60 Alkynyl, C1-C 60 Alkoxy, or C1-C 60 Alkylthio; 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 10-350; or -Si(Q1)(Q2)(Q3), -Ge(Q1)(Q2)(Q3), or -N(Q4)(Q5), Wherein Q1-Q5 are each as described in claim 1: in, 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, * indicates a bonding site with an adjacent atom, "Ph" is a phenyl group, "TMS" is a trimethylsilyl group, and "TMG" is a trimethylgermyl group.

12. The organometallic compound according to claim 1, wherein R 33 is hydrogen or deuterium.

13. The organometallic compound according to claim 1, wherein the organometallic compound is represented by one of Formulas 5-1 to 5-3: in, In formulas 5-1 to 5-3, M1, n1, n2, X1, X2, R 11 -R 13 , and R 31 -R 33 Each as described in claim 1, R 14 -R 17 Each independently as defined in claim 1 for R1, R 21 -R 28 Each independently as defined in claim 1 for R2, R in Formula 5-1 21 , R 22 , and R 25 -R 28 At least one of is not hydrogen, R in Formula 5-2 21 and R 24 -R 28 At least one of is not hydrogen, and R in Formula 5-3 23 -R 28 At least one of is not hydrogen.

14. The organometallic compound of claim 1, wherein the organometallic compound is represented by one of Compounds 1 to 83:

15. 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 organic metal compound as claimed in any one of claims 1 to 14.

16. The light emitting device of claim 15, wherein the emissive layer comprises the at least one organometallic compound.

17. The light emitting device of claim 16, wherein the emissive layer further comprises a host, wherein an amount of the host in the emissive layer is greater than an amount of the at least one organometallic compound in the emissive layer based on weight. The light emitting device of claim 15 , wherein the emission layer emits red light having a maximum emission wavelength of 590 nm to 670 nm.

19. The light emitting device according to claim 15, wherein The first electrode is an anode, The second electrode is a cathode, and The organic layer further includes a hole transport region between the first electrode and the emission layer, and an electron transport region between the emission layer and the second electrode, The hole transport region includes 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 15 to 19.

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