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, provided that i) X45 is C (R45), X46 is C (R46), and R45 and R46 are bonded to each other to form a group represented by Formula 2, ii) X46 is C (R46), X47 is C (R47), and R46 and R47 form a group represented by Formula 2, or iii) X47 is C (R47), X48 is C (R48), and R47 and R48 are bonded to each other to form a group represented by Formula 2, ring CY42 and ring CY5 are fused to each other, and the remaining groups and variables 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. 10-2023-0078354 filed in the Korean Intellectual Property Office on June 19, 2023, and all rights arising therefrom, the entire contents of which are incorporated herein by reference. Technical Field

[0003] The present subject matter relates to an organometallic compound, an organic light-emitting device including the same, and an electronic device including the organic light-emitting device. Background Art

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

[0005] In an example, an organic light emitting device includes an anode, a cathode, and an organic layer arranged between the anode and the cathode, wherein the organic layer includes an emission layer. A hole transport region may be arranged between the anode and the emission layer, and an electron transport region may be arranged between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emission layer to generate excitons. Excitons may transition from an excited state to a ground state, thereby generating light. Summary of the invention

[0006] Provided are an organic metal 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] Formula 2

[0021]

[0022] Wherein, in Formulas 1A, 1B, and 2, X 1 C or N, X 2 is C or N, and X 3 is C 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 3 is (i) a 5-membered carbocyclic group, (ii) a 5-membered heterocyclic group, (iii) 5 -C 30 A 5-membered carbocyclic group fused to a carbocyclic group, or a 1 -C 30 A 5-membered carbocyclic group fused to a heterocyclic group, or (iv) a 5-membered carbocyclic group fused to a heterocyclic group 5 -C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 a 5-membered heterocyclic group fused to a heterocyclic group,

[0025] Cyclo 41 is a 6-membered carbocyclic group or a 6-membered heterocyclic group,

[0026] X 43 C(R 43 ) or N, X 44 C(R 44 ) or N, X 45 C(R 45 ) or N, X 46 C(R46 ) or N, X 47 C(R 47 ) or N, and X 48 C(R 48 ) or N,

[0027] The condition is, i) X 45 C(R 45 ), X 46 C(R 46 ), and R 45 and R 46 bonded to each other to form a group represented by Formula 2, ii) X 46 C(R 46 ), X 47 C(R 47 ), and R 46 and R 47 bonded to each other to form a group represented by Formula 2, or iii) X 47 C(R 47 ), X 48 C(R 48 ), and R 47 and R 48 are bonded to each other to form a group represented by Formula 2,

[0028] Cyclo 42 and CY 5 In the ring CY 5 In where they are fused together,

[0029] represents a single bond or a double bond,

[0030] Y 1 for O, S, Se, C(R 61 )(R 62 ), or N(R 63 ),

[0031] Y 2 for O, S, Se, C(R 64 )(R 65 ), or N(R 66 ),

[0032] X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, and X 54 C(R 54 ) or N,

[0033] R 1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60heteroarylthio 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 ),

[0034] 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,

[0035] 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,

[0036] Multiple R 3 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0037] R 43 -R 48 Two or more adjacent (for example, R 43 and R 44 ) are optionally bonded to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0038] R 51 -R 54Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups,

[0039] b1 and b2 are each independently an integer of 1-10,

[0040] b3 is an integer from 1 to 6,

[0041] b4 is an integer from 1 to 4,

[0042] * and *' respectively represent 1 The binding site

[0043] 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 -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 C1 -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:

[0044] 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,

[0045] 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.-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, C6 -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,

[0046] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -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,

[0047] 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, 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 -C60 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

[0048] -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

[0049] Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0050] According to another aspect, an organic light emitting device includes a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one of the organometallic compounds.

[0051] At least one of the organometallic compounds may be included in an emission layer of the organic layer, and the at least one of the organometallic compounds included in the emission layer may serve as a dopant.

[0052] According to another aspect, an electronic device includes the organic light emitting device. BRIEF DESCRIPTION OF THE DRAWINGS

[0053] From the combination Figure 1 The above and other aspects, features, and advantages of some exemplary embodiments will become more apparent upon consideration of the following detailed description, Figure 1 is a schematic cross-sectional view of an organic light-emitting device according to one or more embodiments. DETAILED DESCRIPTION

[0054] Exemplary embodiments will now be described in further detail, examples of which are illustrated in the accompanying drawings. 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. As used herein, the term "and / or" includes any and all combinations of one or more of the related enumerated items. Expressions such as "at least one (kind) of" when before or after a list of elements modify the entire list of elements without modifying the individual elements of the list.

[0055] The terms used herein are only used for the purpose of describing one or more exemplary embodiments and are not intended to be limiting. As used herein, the singular forms "a (one) (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 the presence of 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.

[0056] 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.

[0057] Exemplary embodiments are described herein with reference to cross-sectional views as schematic diagrams of idealized embodiments. Thus, deviations from the shapes of the figures as a result of, for example, manufacturing techniques and / or tolerances are to be expected. Therefore, the embodiments described herein should not be construed as being limited to the specific shapes of the regions as illustrated herein, but rather include deviations in shape caused by, for example, manufacturing. For example, a region illustrated or described as flat may typically have rough and / or nonlinear features. Moreover, the illustrated sharp corners may be rounded. Therefore, the regions shown in the figures are schematic in nature and their shapes are not intended to illustrate the precise shapes of the regions and are not intended to limit the scope of the claims.

[0058] 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.

[0059] 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.

[0060] As used herein, "about" or "approximately" includes the stated value and means within an acceptable range of deviation for the particular value as determined by one of ordinary skill in the art taking into account the measurement in question and the errors associated with the measurement of the particular quantity (i.e., the limitations of the measurement system). For example, "about" can mean within one or more standard deviations, or within ±10% or 5% relative to the stated value.

[0061] 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".

[0062] One aspect provides an organometallic compound represented by Formula 1:

[0063] Formula 1

[0064] M 1 (L 1 ) n1 (L 2 ) n2 .

[0065] In formula 1, M 1 For transition metals.

[0066] 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.

[0067] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), palladium (Pd), gold (Au), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0068] In one or more embodiments, M 1 It may be iridium (Ir), platinum (Pt), osmium (Os), or rhodium (Rh).

[0069] In one or more embodiments, M 1 It may be iridium (Ir).

[0070] In Formula 1, n1 is 1 or 2, and n2 is 1 or 2.

[0071] In one or more embodiments, the sum of n1 and n2 may be 2 or 3.

[0072] In one or more embodiments, M 1 It may be iridium (Ir), and the sum of n1 and n2 may be 3.

[0073] In one or more embodiments, M 1 It may be platinum (Pt), and the sum of n1 and n2 may be 2.

[0074] In formula 1, L 1 is a ligand represented by Formula 1A:

[0075] Formula 1A

[0076]

[0077] In Formula 1A, X 1 is C or N, and X 2 It is C or N.

[0078] In one or more embodiments, X 1 Can be N, and X 2 Can be C.

[0079] In Formula 1A, ring CY 1 and CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group.

[0080] In one or more embodiments, CY 1 and CY 2 may each independently be i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring,

[0081] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0082] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0083] In one or more embodiments, CY 1 and CY 2Each of the above groups may independently be a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

[0084] In one or more embodiments,

[0085] Cyclo 1 may be a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, and

[0086] Cyclo 2 It may be a benzene group or a naphthyl group.

[0087] In one or more embodiments, in Formula 1A, The group represented may be a group represented by one of the formulae CY(1)-1 to CY(1)-16:

[0088]

[0089] In formulae CY(1)-1 to CY(1)-16,

[0090] R 11 -R 14 can be independently determined as R 1 As described, the condition is R 11 -R 14 Not hydrogen,

[0091] *Indicates the same as M 1 The binding site, and

[0092] *” indicates the binding site with the adjacent atoms.

[0093] In one or more embodiments, in Formula 1A, The group represented may be a group represented by one of the formulae CY(2)-1 to CY(2)-16:

[0094]

[0095] In formulae CY(2)-1 to CY(2)-16,

[0096] R 21 -R 24 can be independently determined as R 2 As described, the condition is R 21-R 24 Not hydrogen,

[0097] *' indicates that the 1 The binding site, and

[0098] *” indicates the binding site with the adjacent atoms.

[0099] In one or more embodiments, L 1 is a ligand represented by formula 1A-1:

[0100]

[0101] In Formula 1A-1,

[0102] X 1 Can be C or N, and X 2 Can be C or N,

[0103] X 11 Can be C(R 11 ) or N, X 12 Can be C(R 12 ) or N, X 13 Can be C(R 13 ) or N, and X 14 Can be C(R 14 ) or N,

[0104] 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,

[0105] R 11 -R 14 can be independently determined as R 1 As described,

[0106] R 21 -R 24 can be independently determined as R 2 described, and

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

[0108] In one or more embodiments, in Formula 1A-1, R 11 -R 14 and R 21 -R 24At least one of the C 1 -C 10 Alkyl (e.g., -CD 3 、-CD 2 H.-CDH 2 wait).

[0109] For example, i) R 11 -R 14 One or both (e.g., R 12 , R 13 , or R 12 and R 13 Both) can be each independently C unsubstituted or substituted with at least one deuterium 1 -C 10 Alkyl, ii) R 21 -R 24 One of the following (for example, R 22 ) may be C which is unsubstituted or substituted with at least one deuterium 1 -C 10 Alkyl, or iii) R 11 -R 14 One of the following (for example, R 12 ) and R 21 -R 24 One of the following (for example, R 22 ) may each be C unsubstituted or substituted with at least one deuterium 1 -C 10 alkyl.

[0110] In formula 1, L 2 is a ligand represented by Formula 1B:

[0111] Formula 1B

[0112]

[0113] In Formula 1B, X 3 It is C or N.

[0114] In one or more embodiments, X 3 Can be N.

[0115] In Formula 1B, ring CY 3 is (i) a 5-membered carbocyclic group, (ii) a 5-membered heterocyclic group, (iii) 5 -C 30 A 5-membered carbocyclic group fused to a carbocyclic group, or a 1 -C 30 A 5-membered carbocyclic group fused to a heterocyclic group, or (iv) a 5-membered carbocyclic group fused to a heterocyclic group 5 -C 30A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 The heterocyclic group is a condensed 5-membered heterocyclic group.

[0116] In one or more embodiments, CY 3 may be i) a first ring, ii) a fused ring group in which two or more first rings are fused to each other, or iii) a fused ring group in which at least one first ring is fused to at least one second ring, provided that ring CY 3 The 5-membered carbocyclic group or 5-membered heterocyclic group contained therein is bonded to M 1 and CY 41 ,

[0117] The first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a thiorrole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiorrole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothitriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azathiorrole group, a diazathiorrole group, or a triazathiorrole group, and

[0118] The second ring may be an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a phenyl group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0119] In one or more embodiments, CY 3 It may be a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

[0120] For example, CY 3 It may be an imidazole group or a benzimidazole group.

[0121] In one or more embodiments, in Formula 1B, The group represented may be a group represented by one of the formulae CY(3)-1 to CY(3)-3:

[0122]

[0123] In formulae CY(3)-1 to CY(3)-3,

[0124] X 31 Can be C(R 31a )、C(R 31a )(R 31b), N, or N(R 31a ),

[0125] X 32 Can be C(R 32a )、C(R 32a )(R 32b ), N, or N(R 32a ),

[0126] X 33 Can be C(R 33a ) or N,

[0127] Cyclo 34 Can be C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups,

[0128] R 31a , R 31b , R 32a , R 32b , R 33a , and R 34 can be independently determined as R 3 As described above, b34 can be an integer from 1 to 10.

[0129] represents a single bond or a double bond,

[0130] In formula CY(3)-1, one of them is a single bond and the other is a double bond,

[0131] *Indicates the same as M 1 The binding site, and

[0132] *” indicates the binding site with the adjacent atoms.

[0133] In one or more embodiments, in Formula 1B, The group represented may be a group represented by one of the formulae CY(3A)-1 to CY(3A)-16:

[0134]

[0135]

[0136] In formulae CY(3A)-1 to CY(3A)-16,

[0137] X 31 Can be C(R 31a )(R 31b ) or N(R 31a ),

[0138] R 31a , R 31b , and R 35 -R 38 can be independently determined as R 3 As described, the condition is that R 31a , R 31b , and R 35 -R 38 Not hydrogen,

[0139] *Indicates the same as M 1 The binding site, and

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

[0141] In one or more embodiments, in Formulas CY(3)-1 to CY(3)-3 and Formulas CY(3A)-1 to CY(3A)-16, X 31 Can be N(R 31a ), and R 31a may be each unsubstituted or substituted by at least one of the following C 6 -C 30 Aryl (e.g., C 6 -C 14 Aryl or C 6 -C 12 Aryl) or C 1 -C 30 Heteroaryl (e.g., C 3 -C 10 Heteroaryl or C 3 -C 8 Heteroaryl): deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or a combination thereof, and

[0142] Q 1 -Q 3 Can be independently:

[0143] -CH 3 、-CD3 、-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 ;

[0144] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0145] 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.

[0146] In Formula 1B, ring CY 41 It is a 6-membered carbocyclic group or a 6-membered heterocyclic group.

[0147] In one or more embodiments, CY 41 It may be a benzene group or a pyridine group.

[0148] In Formula 1B, X 43 C(R 43 ) or N, X 44 C(R 44 ) or N, X 45 C(R 45 ) or N, X 46 C(R 46 ) or N, X 47 C(R 47 ) or N, and X 48 C(R 48 ) or N, provided that, i) X 45 C(R 45 ), X 46 C(R 46), and R 45 and R 46 bonded to each other to form a group represented by Formula 2, ii) X 46 C(R 46 ), X 47 C(R 47 ), and R 46 and R 47 To form a group represented by Formula 2, or iii) X 47 C(R 47 ), X 48 C(R 48 ), and R 47 and R 48 are bonded to each other to form a group represented by Formula 2:

[0149] Formula 2

[0150]

[0151] Ring CY in Formula 1B 42 and the ring CY in formula 2 5 In the ring CY 5 In Converge with each other.

[0152] In formula 2, Indicates a single bond or a double bond.

[0153] It should be understood that, through the above conditions, The part represented by may correspond to: (i) X in Formula 1B 45 and X 46 (ii) the bond between X 46 and X 47 or (iii) X in Formula 1B 47 and X 48 The bond between the ring CY in Formula 1B 42 and the ring CY in formula 2 5 Condensed with each other.

[0154] In Formula 1B, Y 1 for O, S, Se, C(R 61 )(R 62 ), or N(R 63 ).

[0155] In formula 2, Y 2 for O, S, Se, C(R 64 )(R 65 ), or N(R 66 ).

[0156] In one or more embodiments, Y 1 and Y 2 Can be the same as each other.

[0157] In one or more embodiments, Y 1 and Y 2 Can be different from each other.

[0158] In formula 2, X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, and X 54 C(R 54 ) or N.

[0159] In one or more embodiments, L 2 It may be a ligand represented by formula 1B-1:

[0160]

[0161] In Formula 1B-1,

[0162] X 4 Can be C or N, and X 5 Can be C or N,

[0163] X 41 Can be C(R 41 ) or N, and X 42 Can be C(R 42 ) or N,

[0164] R 41 and R 42 can be independently determined as R 4 As described,

[0165] X 3 CY 3 , Y 1 , X 43 -X 48 CY 42 , R 3 , and b3 may each be as described herein, and

[0166] * and *' respectively represent 1 binding site.

[0167] In one or more embodiments, L 2 It may be a ligand represented by one of Formulas 1B(1)-1 to 1B(1)-6:

[0168]

[0169]

[0170] In Formulae 1B(1)-1 to 1B(1)-6,

[0171] X 41 Can be C(R 41 ) or N, and X 42 Can be C(R 42 ) or N,

[0172] R 41 and R 42 can be independently determined as R 4 As described,

[0173] X 3 CY 3 , Y 1 , X 43 -X 48 CY 42 , R 3 , and b3 may each be as described herein, and

[0174] * and *' respectively represent 1 binding site.

[0175] In one or more embodiments, L 2 It may be a ligand represented by one of formulae 1B(2)-1 to 1B(2)-6:

[0176]

[0177] In Formulae 1B(2)-1 to 1B(2)-6,

[0178] R 30 and R 31 can be independently determined as R 3 As described,

[0179] b30 can be an integer from 1 to 4.

[0180] X 41 Can be C(R 41 ) or N, and X 42 Can be C(R 42 ) or N,

[0181] R 41 and R 42 can be independently determined as R 4 As described,

[0182] Y 1 , Y2 , X 43 -X 48 , and X 51 -X 54 may each be as described herein, and

[0183] * and *' respectively represent 1 binding site.

[0184] In one or more embodiments, in Formulas 1B(2)-1 to 1B(2)-6, R 31 may be each unsubstituted or substituted by at least one of the following C 6 -C 30 Aryl (e.g., C 6 -C 14 Aryl or C 6 -C 12 Aryl) or C 1 -C 30 Heteroaryl (e.g., C 3 -C 10 Heteroaryl or C 3 -C 8 Heteroaryl): deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or a combination thereof, and

[0185] Q 1 -Q 3 Can be independently: -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 ;

[0186] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0187] 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.

[0188] In Formulas 1A, 1B, and 2, R 1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 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 2 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60Aryl, 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 ).

[0189] In one or more embodiments, R 1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 Can be independently:

[0190] Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2, hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;

[0191] 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;

[0192] 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;

[0193] 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, pyridyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3), or a combination thereof; or

[0194] -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

[0195] Q 1 -Q 9 Can be independently:

[0196] -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 ;

[0197] n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or

[0198] 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.

[0199] In one or more embodiments, R1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 Can be independently:

[0200] 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;

[0201] 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 10-134, or 10-201 to 10-350; or

[0202] -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or -N(Q 4 )(Q 5 ):

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211] In formulae 9-1 to 9-39, 9-44 to 9-61, 9-201 to 9-240, 10-1 to 10-134, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, "Ph" represents a phenyl group, "TMS" represents a trimethylsilyl group, and "TMG" represents a trimethylgermyl group.

[0212] In Formula 1A, 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 group.

[0213] In Formula 1A, 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 group.

[0214] In Formula 1B, multiple R 3 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0215] In Formula 1B, R 43 -R 48 Two or more adjacent (for example, R 43 and R 44 ) are optionally bonded to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0216] In formula 2, R 51 -R 54 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic group.

[0217] In Formula 1A, b1 and b2 are each independently an integer of 1-10.

[0218] In Formula 1B, b3 is an integer of 1-6, and b4 is an integer of 1-4, for example, an integer of 1-2.

[0219] In Formulae 1A and 1B, * and *' each represent 1 binding site.

[0220] In one or more embodiments, the organometallic compound may be represented by at least one of Compounds 1 to 30:

[0221]

[0222]

[0223] In one or more embodiments, the organometallic compound may be electrically neutral.

[0224] The organic metal compound represented by Formula 1 satisfies the structure of Formula 1 described above, and includes a ligand having a structure represented by Formula 1B. Due to the structure, the organic metal compound represented by Formula 1 may have excellent luminescent properties, and in particular, may have properties suitable for use as a luminescent material having high color purity by controlling an emission wavelength range.

[0225] In addition, the organometallic compound represented by Formula 1 may have excellent electrical mobility. Therefore, an electronic device such as an organic light emitting device including at least one of the organometallic compounds represented by Formula 1 may exhibit low driving voltage, high efficiency, and long lifespan.

[0226] The density functional theory (DFT) method of Gaussian 09 program was used to calculate the highest occupied molecular orbital (HOMO) energy level, the lowest unoccupied molecular orbital (LUMO) energy level, the singlet state (S) energy level and the molecular structure of the organometallic compound represented by Formula 1 under the condition of optimizing the molecular structure at the B3LYP level. 1 ) energy level, and triplet state (T 1 ) energy levels, and the results are shown in Table 1. The energy levels are expressed in electron volts (eV).

[0227] Table 1

[0228]

[0229]

[0230] As confirmed by Table 1, the organometallic compound represented by Formula 1 has such electrical characteristics as to be suitable for use as a dopant for electronic devices such as organic light emitting devices.

[0231] In one or more embodiments, the maximum emission wavelength (emission peak wavelength, or peak emission wavelength, λ) of the emission peak of the emission spectrum or electroluminescence (EL) spectrum of the organometallic compound is max ) can be from about 490 nanometers (nm) to about 550 nm.

[0232] 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.

[0233] Therefore, the organometallic compound represented by Formula 1 can be suitably used as a dopant in an organic layer, such as an emission layer, of an organic light-emitting device. Therefore, another aspect provides an organic light-emitting device comprising a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer comprises an emission layer, and wherein the organic layer comprises at least one of the organometallic compounds represented by Formula 1.

[0234] Due to including the organic layer including at least one of the organometallic compounds represented by Formula 1 as described herein, the organic light emitting device may have excellent driving voltage, excellent maximum external quantum efficiency, and excellent lifespan characteristics.

[0235] The organic metal compound represented by Formula 1 can be used between the electrode pairs of the organic light-emitting device. For example, at least one of the organic metal compounds represented by Formula 1 can be included in the emission layer. In this regard, the organic metal compound can act as a dopant, and the emission layer can further include a host. When the emission layer further includes a host, the amount of the host in the emission layer can be greater than the amount of the at least one organic metal compound represented by Formula 1 in the emission layer based on weight.

[0236] In one or more embodiments, the emission layer may emit green light. For example, the emission layer may emit green light having a maximum emission wavelength of about 490 nm to about 550 nm.

[0237] The expressions “(organic layer) includes at least one organometallic compound represented by Formula 1” or “(organic layer) includes at least one of the organometallic compounds represented by Formula 1” may be used interchangeably herein and may include the case where “(organic layer) includes the same organometallic compound represented by Formula 1” and the case where “(organic layer) includes two or more different organometallic compounds represented by Formula 1”.

[0238] 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 present 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).

[0239] 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.

[0240] In one or more embodiments, in the organic light-emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region arranged between the first electrode and the emission layer, and an electron transport region arranged between the emission layer and the second electrode, wherein 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, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0241] The term "organic layer" as used herein refers to a single layer or a plurality of layers disposed 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.

[0242] 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, but the embodiments are not limited thereto. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19, which are sequentially stacked in the stated order.

[0243] A substrate may be additionally disposed under the first electrode 11 or on the second electrode 19. For use as the substrate, any substrate for an organic light-emitting device available in the art may be used, and for example, a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, easy handling (processing), and / or water resistance may be used.

[0244] 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).

[0245] The first electrode 11 may have a single-layer structure or a multi-layer structure including a plurality of layers. For example, the first electrode 11 may have a three-layer structure of ITO / Ag / ITO, but the embodiment is not limited thereto.

[0246] The organic layer 15 may be disposed on the first electrode 11 .

[0247] The organic layer 15 may include an emission layer, and may further include a hole transport region, an electron transport region, or a combination thereof.

[0248] The hole transport region may be disposed between the first electrode 11 and the emission layer.

[0249] 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.

[0250] The hole transport region may include only a hole injection layer or only 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 constituent layers of each structure are sequentially stacked in the order stated starting from the first electrode 11.

[0251] When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods such as vacuum deposition, spin coating, casting, Langmuir-Blodgett (LB) deposition, etc., or a combination thereof.

[0252] When the hole injection layer is formed by vacuum deposition, the deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature of about 100° C. to about 500° C., a ... -8 Torr - about 10 -3Torr, and at about 0.01 angstrom / second ( / second)-approx. The deposition rate may be in the range of 100 Å / s, but the embodiment is not limited thereto.

[0253] When the hole injection layer is formed by spin coating, the coating conditions may vary according to the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the coating conditions 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 the solvent after coating, but the embodiment is not limited thereto.

[0254] Conditions for forming the hole transport layer and the electron blocking layer may be the same as or similar to conditions for forming the hole injection layer.

[0255] 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:

[0256]

[0257]

[0258] Formula 201

[0259]

[0260] Formula 202

[0261]

[0262] In formula 201, Ar 101 and Ar 102 Can be independently:

[0263] 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

[0264] 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, C2 -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.

[0265] In Formula 201, xa and xb may each independently be an integer of 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1, and xb may be 0, but the embodiment is not limited thereto.

[0266] In equations 201 and 202, R 101 -R 108 , R 111 -R 119 , and R 121 -R 124 Can be independently:

[0267] 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;

[0268] Each of the following C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, or a combination thereof;

[0269] Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl; or

[0270] 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.

[0271] In formula 201, R 109 Can be:

[0272] phenyl, naphthyl, anthracenyl, or pyridyl; or

[0273] 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.

[0274] In one or more embodiments, the compound represented by Formula 201 may be represented by Formula 201A, but the embodiments are not limited thereto:

[0275] Formula 201A

[0276]

[0277] In Formula 201A, R 101 , R 111 , R 112 , and R 109 Each may be as described herein.

[0278] For example, the compound represented by Formula 201 and the compound represented by Formula 202 may include one or more of compounds HT1 to HT20, but the embodiment is not limited thereto:

[0279]

[0280]

[0281] The thickness of the hole transport region may be about -about For example, about -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 -about For example, about -about The thickness of the hole transport layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0282] In addition to the materials described above, the hole transport region may further include a charge generating material for improving the conductive property. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.

[0283] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of the following: a quinone derivative, a metal oxide, or a compound containing a cyano group, but the embodiment is not limited thereto. 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 embodiment is not limited thereto:

[0284]

[0285] The hole transport region may further include a buffer layer.

[0286] The buffer layer may compensate for an optical resonance distance depending on a wavelength of light emitted from the emission layer to improve efficiency of an organic light emitting device.

[0287] Meanwhile, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be selected from the materials for the hole transport region described above and the materials for the host described below, but the embodiment is not limited thereto. For example, when the hole transport region includes an electron blocking layer, the material for the electron blocking layer may be mCP, which will be described in further detail below.

[0288] The emission layer may be formed on the hole transport region by using one or more suitable methods such as vacuum deposition, spin coating, casting, LB deposition, etc. When the emission layer is formed by vacuum deposition or spin coating, the deposition or coating conditions may be similar to those applied when forming the hole injection layer, although the deposition or coating conditions may vary depending on the material used.

[0289] 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.

[0290] The host may include at least one of 1,3,5-tri(1-phenyl-1H-benzo[d]imidazol-2-yl)benzene (TPBi), 3-tert-butyl-9,10-di(naphthalene-2-yl)anthracene (TBADN), 9,10-di(naphthalene-2-yl)anthracene (ADN) (also referred to as "DNA"), 4,4'-bis(N-carbazolyl)-1,1'-biphenyl (CBP), 4,4'-bis(9-carbazolyl)-2,2'-dimethyl-biphenyl (CDBP), 1,3,5-tri(carbazolyl-9-yl)benzene (TCP), 1,3-bis(N-carbazolyl)benzene (mCP), compound H50, or compound H51, but embodiments are not limited thereto:

[0291]

[0292] In one or more embodiments, the host may include a compound represented by Formula 301:

[0293] Formula 301

[0294]

[0295] In formula 301, Ar 111 and Ar 112 Can be independently:

[0296] Phenylene, naphthylene, phenanthrenyl, or pyrenylene; or

[0297] Phenylene, naphthylene, phenanthrenylene, or pyrenylene, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0298] In formula 301, Ar 113 -Ar 116 Can be independently:

[0299] C is unsubstituted or substituted with at least one of the following 1 -C 10 Alkyl: phenyl, naphthyl, anthracenyl, or a combination thereof;

[0300] Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl;

[0301] 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

[0302] A group represented by:

[0303]

[0304] However, the embodiment is not limited thereto.

[0305] In formula 301, Ar 113 -Ar 116 Can be independently:

[0306] C 1 -C 10 alkyl, phenyl, naphthyl, phenanthrenyl, or pyrenyl; or

[0307] Phenyl, naphthyl, phenanthrenyl, or pyrenyl, each substituted with at least one of phenyl, naphthyl, anthracenyl, or a combination thereof.

[0308] In Formula 301, g, h, i, and j may each independently be an integer of 0-4, and for example, may each independently be 0, 1, or 2.

[0309] In one or more embodiments, the host may include a compound represented by Formula 302:

[0310] Formula 302

[0311]

[0312] In formula 302, Ar 122 -Ar 125 The Ar in Formula 301 can be 113 as described.

[0313] In formula 302, Ar126 and Ar 127 Can be independently C 1 -C 10 Alkyl (eg, methyl, ethyl, propyl, etc.).

[0314] 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.

[0315] 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, due to the stacked structure including the red emission layer, the green emission layer, and / or the blue emission layer, the emission layer may emit white light, and various modifications are possible.

[0316] When the emission layer includes a host and a dopant, an amount of the dopant may be about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but the embodiment is not limited thereto.

[0317] The thickness of the emission layer may be about -about For example, about -about Without wishing to be bound by theory, when the thickness of the emission layer is within these ranges, excellent light emitting characteristics may be obtained without a significant increase in driving voltage.

[0318] Next, an electron transport region may be disposed on the emission layer.

[0319] The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.

[0320] For example, the electron transport region may have a hole blocking layer / electron transport layer / electron injection layer structure or an electron transport layer / electron injection layer structure, but the embodiment is not limited thereto. The electron transport layer may have a multilayer structure or a single layer structure including two or more different materials.

[0321] Conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer constituting the electron transport region may be the same as or similar to the conditions for forming the hole injection layer.

[0322] 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:

[0323]

[0324] The thickness of the hole blocking layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0325] 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:

[0326]

[0327] In one or more embodiments, the electron transport layer may include at least one of compounds ET1 to ET25, but embodiments are not limited thereto:

[0328]

[0329]

[0330] The thickness of the electron transport layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0331] The electron transport layer may further include a material containing a metal in addition to the materials described above.

[0332] The metal-containing material may include a Li complex. The Li complex may include, for example, a compound ET-D1 (8-hydroxyquinoline lithium, LiQ) or ET-D2, but the embodiment is not limited thereto:

[0333]

[0334] The electron transport region may include an electron injection layer that facilitates electron injection from the second electrode 19 .

[0335] The electron injection layer may include compounds ET-D1, LiF, NaCl, CsF, Li 2 O, BaO, or a combination thereof.

[0336] The thickness of the electron injection layer may be about -about For example, about -about Without wishing to be bound by theory, 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.

[0337] The second electrode 19 may be arranged on the organic layer 15. The second electrode 19 may be a cathode. The material used to form 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, the material used to form the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In one or more embodiments, in order to manufacture a top-emitting light-emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19, and various modifications are possible.

[0338] In the above, reference has been made to Figure 1 The organic light emitting device 10 is described, but the embodiment is not limited thereto.

[0339] On the other hand, an electronic device including the organic light-emitting device is provided. In addition to the organic light-emitting device as described herein, the electronic device may further include a thin film transistor (TFT). The thin film transistor may include a source electrode, a drain electrode, and an active layer, wherein any one of the source electrode and the drain electrode may be electrically connected to any one of the first electrode and the second electrode of the organic light-emitting device, but the embodiment is not limited thereto.

[0340] Another aspect provides a diagnostic composition comprising at least one organometallic compound represented by Formula 1.

[0341] Since the organometallic compound represented by Formula 1 provides high luminescence efficiency, the diagnostic composition including at least one of the organometallic compounds represented by Formula 1 may have high diagnostic efficiency.

[0342] The diagnostic composition can be used in various applications such as diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc., but the embodiments are not limited thereto.

[0343] As used herein, the term "C 1 -C 60 "Alkyl" refers to a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and non-limiting examples thereof include methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl, and the like. As used herein, the term "C 1 -C 60 "Alkylene" refers to a group having a C 1 -C 60 Alkyl is a divalent group of the same structure.

[0344] As used herein, the term "C 1 -C 60 "Alkoxy" refers to a 101 (A 101 C 1 -C 60 The term "alkyl" refers to a monovalent group represented by an alkyl group, and non-limiting examples thereof include methoxy, ethoxy, isopropoxy, and the like.

[0345] As used herein, the term "C 1 -C 60 "Alkylthio" refers to -SA 101 (A 101 C 1 -C 60 A monovalent group represented by an alkyl group.

[0346] As used herein, the term "C 2 -C 60 "Alkenyl" refers to a group consisting of 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon double bond in the middle or at the terminal of an alkyl group, and non-limiting examples thereof include vinyl, propenyl, butenyl, etc. 2 -C 60 "Alkenylene" refers to a 2 -C 60 Alkenyl is a divalent group of the same structure.

[0347] As used herein, the term "C 2 -C 60 "Alkynyl" refers to a 2 -C 60 The term "C" as used herein refers to a hydrocarbon group formed by inserting at least one carbon-carbon triple bond in the middle or at the terminal of an 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.

[0348] As used herein, the term "C 3 -C 10 "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like. As used herein, the term "Cycloalkyl" refers to a monovalent saturated hydrocarbon ring group having 3 to 10 carbon atoms, and non-limiting examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, adamantyl, norbornyl, and the like. 3 -C 10 "Cycloalkylene" refers to a cycloalkylene having a 3 -C 10 Cycloalkyl is a divalent group of the same structure.

[0349] As used herein, the term "C 1 -C 10 "Heterocycloalkyl" refers to a monovalent cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring-forming atom and 1 to 10 carbon atoms as ring-forming atoms, and non-limiting examples thereof include tetrahydrofuranyl, tetrahydrothienyl, and the like. As used herein, the term "C 1 -C 10 "Heterocycloalkylene" refers to a group having a C 1 -C 10 Heterocycloalkyl is a divalent group of the same structure.

[0350] As used herein, the term "C 3 -C 10 "Cycloalkenyl" refers to a monovalent cyclic group having 3 to 10 carbon atoms, at least one carbon-carbon double bond and no aromaticity in its ring, and non-limiting examples thereof include cyclopentenyl, cyclohexenyl, cycloheptenyl, norbornenyl, and the like. As used herein, the term "C 3 -C 10 "Cycloalkenylene" refers to a 3 -C 10 Cycloalkenyl is a divalent group of the same structure.

[0351] As used herein, the term "C1 -C 10 The term "heterocycloalkenyl" refers to a monovalent cyclic group having at least one heteroatom selected from B, N, O, P, Si, S, Se, or 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.

[0352] As used herein, the term "C 6 -C 60 "Aryl" refers to a monovalent group having a carbocyclic aromatic ring system having 6 to 60 carbon atoms, and as used herein, the term "C 6 -C 60 "Arylene" refers to a divalent group having a carbocyclic aromatic ring system having 6 to 60 carbon 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.

[0353] As used herein, the term "C 7 -C 60 "Alkylaryl" refers to a 1 -C 54 Alkyl substituted C 6 -C 59 Aryl.

[0354] As used herein, the term "C 7 -C 60 "Arylalkyl" refers to a 6 -C 59 Aryl substituted C 1 -C 54 alkyl.

[0355] As used herein, the term "C 1 -C 60The term "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, or Ge as a ring atom and 1 to 60 carbon atoms as ring atoms, and as used herein, the term "C 1 -C 60 The term "heteroarylene" refers to a divalent group having a heterocyclic aromatic ring system having at least one heteroatom selected from B, N, O, P, Si, S, Se, or Ge as a ring atom and 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.

[0356] 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.

[0357] As used herein, the term "C 6 -C 60 "Aryloxy" refers to -OA 102 (A 102 C 6 -C 60 aryl), and as used herein, the term "C 6 -C 60 "Arylthio" refers to -SA 103 (A 103 C 6 -C 60 aryl).

[0358] As used herein, the term "C 1 -C 60 "Heteroaryloxy" refers to -OA 104 (A 104 C 1 -C60 Heteroaryl), and as used herein, the term "C 1 -C 60 "Heteroarylthio" refers to -SA 105 (A 105 C 1 -C 60 heteroaryl).

[0359] 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.

[0360] 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, or 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.

[0361] 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.

[0362] As used herein, the term "C 1 -C 30 The term "heterocyclic group" refers to a saturated or unsaturated ring group having at least one heteroatom selected from B, N, O, Si, P, S, Se, or Ge as a ring atom in addition to 1 to 30 carbon atoms as ring atoms. 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.

[0363] Substituted C 5 -C 30 Carbocyclic groups, substituted C 1 -C 30 Heterocyclic groups, substituted C1 -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 -C 60 Alkyl aryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituted monovalent non-aromatic condensed heteropolycyclic group may be:

[0364] Deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;

[0365] 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.-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 )(Q13 )、-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;

[0366] C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 a heteroarylthio group, a monovalent non-aromatic condensed polycyclic group, or a monovalent non-aromatic condensed heteropolycyclic group;

[0367] 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, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q22 )(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

[0368] -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

[0369] 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 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10Cycloalkenyl, substituted or unsubstituted C 2 -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 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

[0370] For example, Q 1 -Q 9 , Q 11 -Q 19 , Q 21 -Q 29 , and Q 31 -Q 39 Can be independently:

[0371] 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, or C each of which is unsubstituted or substituted by at least one of the following 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10Heterocycloalkyl, 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 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.

[0372] Hereinafter, the organometallic compound represented by Formula 1 and the organic light-emitting device according to one or more embodiments will be described in further detail with reference to Synthesis Examples and Examples. However, the embodiment is not limited thereto. The phrase "using B instead of A" used in describing the Synthesis Examples means that, based on molar equivalents, the amount of B used is the same as the amount of A used.

[0373] Example

[0374] Synthesis Example 1: Synthesis of Compound 1

[0375]

[0376] Synthesis of Compound 1A(1)

[0377] 2-Phenyl-pyridine (5.2 g, 33.5 mmol) and iridium chloride trihydrate (IrCl 3 (H 2 O) n, n=3, the same below) (5.2 g, 14.8 mmol) was mixed with 120 milliliters (mL) of 2-ethoxyethanol and 25 mL of deionized (DI) water, and heated and stirred under reflux for 24 hours. Then, the temperature was lowered to room temperature. The resulting solid was separated by filtration, washed thoroughly with water, methanol, and hexane in the order stated, and then dried in a vacuum oven to obtain 7.2 g (91% yield) of compound 1A (1).

[0378] Synthesis of compound 1A

[0379] Compound 1A (1) (1.6 g, 1.5 mmol) was mixed with 45 mL of dichloromethane (MC), and then, silver trifluoromethanesulfonate (AgOTf) (0.6 g, 2.3 mmol) mixed with 15 mL of methanol (MeOH) was added thereto. Afterwards, the mixture was stirred at room temperature for 18 hours while shielding light with aluminum foil, and then filtered through diatomaceous earth to remove the resulting solid. The solvent was removed from the filtrate under reduced pressure to obtain a solid (Compound 1A), which was used in the next reaction without additional purification processes.

[0380] Synthesis of compound 1B

[0381] In a nitrogen atmosphere, 2-(Benzo[4',5']furo[2',3':5,6]naphtho[1,2-b]benzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.1 g, 2.54 mmol) and 2-bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole (1.0 g, 2.31 mmol) were dissolved in 45 mL of 1,4-dioxane. Then, potassium carbonate (K 2 CO 3 ) (0.73 g, 5.28 mmol) was dissolved in 15 mL of DI water and added to the reaction mixture, and a palladium catalyst (tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 ) (0.13 g, 0.11 mmol). After that, the reaction mixture was stirred and heated under reflux at 100° C. After an extraction process was performed thereon, the obtained solid was purified by column chromatography (eluent: MC and hexane) to obtain 1.25 g (82% yield) of compound 1B. The obtained compound was confirmed by high resolution mass spectrometry (HRMS (MALDI)) using matrix-assisted laser desorption ionization and high performance liquid chromatography (HPLC) analysis.

[0382] HRMS (MALDI): For C 47 H 36 N2 O 2 Calculated value: m / z: 660.82; found: 661.78.

[0383] 2-Bromo-1-(3,5-diisopropyl-[1,1'-biphenyl]-4-yl)-1H-benzo[d]imidazole was synthesized according to the following reaction scheme. The yield of the compound is as described in the scheme.

[0384]

[0385] 2-(Benzo[4',5']furo[2',3':5,6]naphtho[1,2-b]benzofuran-6-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was synthesized according to the following reaction scheme. The product yields of each step are as described in the scheme.

[0386]

[0387] Synthesis of compound 1

[0388] Compound 1A (1.1 g, 1.6 mmol) and compound 1B (1.2 g, 1.8 mmol) were mixed with 10 mL of 2-ethoxyethanol and 10 mL of N, N-dimethylformamide, and stirred and heated under reflux for 24 hours. Then, the temperature was lowered to room temperature. An extraction process was performed on it with MC and water, and the water layer was removed therefrom. The obtained organic layer was treated with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. After the extraction process was performed on it, the obtained solid was purified by column chromatography (eluent: MC and hexane) to obtain 0.90 g (50% yield) of compound 1. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0389] HRMS (MALDI): For C 69 H 51 Ir 4 O 2 Calculated value: m / z: 1160.41; found value: 1161.32.

[0390] Synthesis Example 2: Synthesis of Compound 7

[0391]

[0392] Synthesis of compound 7

[0393] 0.84 g (40% yield) of compound 7 was obtained in a similar manner to the synthesis of compound 1, except that 5-(methyl-d3)-2-phenylpyridine (5.7 g, 33.1 mmol) was used instead of 2-phenyl-pyridine in the synthesis of compound 1A (1) in the synthesis of compound 7A. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0394] HRMS (MALDI): For C 71 H 49 D 6 Ir 4 O 2 Calculated value: m / z: 1194.50; found: 1195.34.

[0395] Synthesis Example 3: Synthesis of Compound 13

[0396]

[0397] Synthesis of compound 13

[0398] 0.76 g (37% yield) of compound 13 was obtained in a similar manner to the synthesis of compound 1, except that 4,5-bis(methyl-d3)-2-phenylpyridine (6.04 g, 31.91 mmol) was used instead of 2-phenyl-pyridine in the synthesis of compound 1A (1) in the synthesis of compound 13A. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0399] HRMS (MALDI): For C 73 H 47 D 12 Ir 4 O 2 Calculated value: m / z: 1228.59; found: 1229.41.

[0400] Synthesis Example 4: Synthesis of Compound 19

[0401]

[0402] Synthesis of compound 19

[0403] 0.71 g (34% yield) of compound 19 was obtained in a similar manner to the synthesis of compound 1, except that 5-(methyl-d3)-2-(4-(methyl-d3)phenyl)pyridine (6.04 g, 31.91 mmol) was used in the synthesis of compound 19A instead of 2-phenyl-pyridine in the synthesis of compound 1A (1). The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.

[0404] HRMS (MALDI): For C 73 H 47 D 12 Ir 4 O 2 Calculated value: m / z: 1228.59; found: 1229.38.

[0405] Example 1

[0406] The ITO (as anode) patterned glass substrate was cut into a size of 50 millimeters (mm)×50 mm×0.5 mm, sonicated with isopropyl alcohol and DI water for 5 minutes each, and then cleaned by exposure to ultraviolet light and ozone for 30 minutes. The resulting glass substrate was loaded onto a vacuum deposition apparatus.

[0407] Compound HT3 and compound F12-P-dopant were co-deposited on the anode by vacuum at a weight ratio of 98:2 to form a A hole injection layer having a thickness of , and compound HT3 is vacuum deposited on the hole injection layer to form a The hole transport layer has a thickness of .

[0408] Then, compound GH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer by vacuum at a weight ratio of 92:8 to form a The thickness of the emission layer.

[0409] Afterwards, compound ET3 and 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.

[0410]

[0411] Examples 2-4 and Comparative Examples 1 and 2

[0412] Organic light-emitting devices were manufactured in a similar manner to that in Example 1, except that in forming the emission layer, the compounds shown in Table 2 were each used as a dopant instead of Compound 1.

[0413] Evaluation Example 1: Evaluation of Characteristics of Organic Light-Emitting Device

[0414] For the organic light emitting devices (OLEDs) of Examples 1 to 4 and Comparative Examples 1 and 2, the driving voltage (V), the maximum external quantum efficiency (Max EQE, %), the maximum emission wavelength (λ max , nm), and lifetime (LT 97 , relative %), and the results are shown in Table 2. As evaluation equipment, a current-voltage meter (Keithley 2400) and a brightness meter (Minolta Cs-1000A) were used. Lifespan (LT 97 ) (at 6,000 nits) is a measure of the time it takes for the luminance to drop to 97% of the initial luminance of 100%, and the lifetime value is expressed as a relative value relative to Comparative Example 1.

[0415] Table 2

[0416]

[0417]

[0418] As confirmed by Table 2, the organic light emitting devices of Examples 1 to 4 have low driving voltage, high maximum external quantum efficiency, and long life characteristics.

[0419] As confirmed by Table 2, compared with the organic light-emitting devices of Comparative Examples 1 and 2, the organic light-emitting devices of Examples 1 to 4 have lower driving voltage, higher maximum external quantum efficiency, and significantly improved lifespan.

[0420] As described above, the organometallic compound represented by Formula 1 may have excellent electrical properties. Therefore, an electronic device such as an organic light-emitting device including at least one of the organometallic compounds represented by Formula 1 may have low driving voltage, high external quantum efficiency, and long life characteristics. Therefore, by using the organometallic compound, a high-quality organic light-emitting device may be realized.

[0421] 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 organic metal compound represented by Formula 1: M 1 (L 1 ) n1 (L 2 ) n2 in, In formula 1, M 1 For transition metals, L 1 is a ligand represented by Formula 1A, L 2 is a ligand represented by formula 1B, and n1 and n2 are each independently 1 or 2, Formula 1A Formula 1B Formula 2 Wherein, in Formulas 1A, 1B, and 2, X 1 C or N, X 2 is C or N, and X 3 is C or N, Cyclo 1 and CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups, Cyclo 3 is (i) a 5-membered carbocyclic group, (ii) a 5-membered heterocyclic group, (iii) 5 -C 30 A 5-membered carbocyclic group fused to a carbocyclic group, or a 1 -C 30 A 5-membered carbocyclic group fused to a heterocyclic group, or (iv) a 5-membered carbocyclic group fused to a heterocyclic group 5 -C 30 A 5-membered heterocyclic group fused to a carbocyclic group, or a 1 -C 30 a 5-membered heterocyclic group fused to a heterocyclic group, Cyclo 41 is a 6-membered carbocyclic group or a 6-membered heterocyclic group, X 43 C(R 43 ) or N, X 44 C(R 44 ) or N, X 45 C(R 45 ) or N, X 46 C(R 46 ) or N, X 47 C(R 47 ) or N, and X 48 C(R 48 ) or N, The condition is, i) X 45 C(R 45 ), X 46 C(R 46 ), and R 45 and R 46 bonded to each other to form a group represented by Formula 2, ii) X 46 C(R 46 ), X 47 C(R 47 ), and R 46 and R 47 To form a group represented by Formula 2, or iii) X 47 C(R 47 ), X 48 C(R 48 ), and R 47 and R 48 are bonded to each other to form a group represented by Formula 2, Cyclo 42 and CY 5 In the ring CY 5 In where they are fused together, represents a single bond or a double bond, Y 1 O, S, Se, C(R 61 )(R 62 ), or N(R 63 ), Y 2 O, S, Se, C(R 64 )(R 65 ), or N(R 66 ), X 51 C(R 51 ) or N, X 52 C(R 52 ) or N, X 53 C(R 53 ) or N, and X 54 C(R 54 ) or N, R 1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 are independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , hydroxyl, cyano, nitro, amino, amidino, hydrazine, hydrazone, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid group or its salt, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkyl aryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ), or -P(=O)(Q 8 )(Q 9 ), 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, 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, Multiple R 3 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups, R 43 and R 44 are optionally bonded to each other to form a substituted or unsubstituted C 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups, R 51 -R 54 Two or more adjacent groups of 5 -C 30 A carbocyclic group or a substituted or unsubstituted C 1 -C 30 Heterocyclic groups, b1-b3 are each independently an integer of 1-10, b4 is an integer from 1 to 4, * and *' respectively represent 1 The binding site 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 -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: 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; 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.-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 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 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; C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 2 -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; 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, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkyl aryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 heteroarylthio group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -Si(Q 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(=O)(Q 28 )(Q 29 ), or a combination thereof; or -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 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 C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 a heteroarylthio group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group.

2. The organometallic compound according to claim 1, wherein M 1 is iridium, platinum, osmium, palladium, gold, titanium, zirconium, hafnium, europium, terbium, thulium, or rhodium.

3. The organometallic compound according to claim 1, wherein M 1 for Ir, and The sum of n1 and n2 is 3.

4. The organometallic compound according to claim 1, wherein the ring CY 1 and CY 2 Each is independently a benzene group, a naphthyl group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.

5. The organometallic compound according to claim 1, wherein the ring CY 3 is a pyrrole group, an imidazole group, a pyrazole group, an oxazole group, an indole group, an azaindole group, a benzopyrazole group, a benzimidazole group, or a benzoxazole group.

6. The organometallic compound according to claim 1, wherein in Formula 1A The group represented is a group represented by one of the formulae CY(1)-1 to CY(1)-16: in, In formulae CY(1)-1 to CY(1)-16, R 11 -R 14 Each independently as claimed in claim 1 regarding R 1 Defined, the condition is R 11 -R 14 Not hydrogen, *Indicates the same as M 1 The binding site, and *” indicates the binding site with the adjacent atoms.

7. The organometallic compound according to claim 1, wherein in Formula 1A The group represented is a group represented by one of the formulae CY(2)-1 to CY(2)-16: in, In formulae CY(2)-1 to CY(2)-16, R 21 -R 24 Each independently as claimed in claim 1 regarding R 2 Defined, the condition is R 21 -R 24 Not hydrogen, *' indicates that the 1 The binding site, and *” indicates the binding site with the adjacent atoms.

8. The organometallic compound as claimed in claim 1, wherein in Formula 1B The group represented is a group represented by one of the formulae CY(3)-1 to CY(3)-3: in, In formulae CY(3)-1 to CY(3)-3, X 31 C(R 31a )、C(R 31a )(R 31b ), N, or N(R 31a ), X 32 C(R 32a )、C(R 32a )(R 32b ), N, or N(R 32a ), X 33 C(R 33a ) or N, Cyclo 34 C 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic groups, R 31a , R 31b , R 32a , R 32b , R 33a , and R 34 Each independently as claimed in claim 1 regarding R 3 As defined, b34 is an integer from 1 to 10. represents a single bond or a double bond, In formula CY(3)-1, one of them is a single bond and the other is a double bond, *Indicates the same as M 1 The binding site, and *” indicates the binding site with the adjacent atoms.

9. The organometallic compound according to claim 1, wherein L 1 is a ligand represented by formula 1A-1: in, In Formula 1A-1, X 1 and X 2 As defined in claim 1, X 11 C(R 11 ) or N, X 12 C(R 12 ) or N, X 13 C(R 13 ) or N, and X 14 C(R 14 ) or N, 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, R 11 -R 14 Each independently as claimed in claim 1 regarding R 1 As defined, R 21 -R 24 Each independently as claimed in claim 1 regarding R 2 defined, and * and *' respectively represent 1 binding site.

10. The organometallic compound according to claim 1, wherein L 2 is a ligand represented by formula 1B-1: in, In Formula 1B-1, X 4 is C or N, and X 5 is C or N, X 41 C(R 41 ) or N, and X 42 C(R 42 ) or N, R 41 and R 42 Each independently as claimed in claim 1 regarding R 4 As defined, X 3 CY 3 , Y 1 , X 43 -X 48 CY 42 , R 3 , and b3 are each as defined in claim 1, and * and *' respectively represent 1 binding site.

11. The organometallic compound according to claim 1, wherein L 2 is a ligand represented by one of Formulae 1B(1)-1 to 1B(1)-6: in, In Formulae 1B(1)-1 to 1B(1)-6, X 41 C(R 41 ) or N, and X 42 C(R 42 ) or N, R 41 and R 42 Each independently as claimed in claim 1 regarding R 4 As defined, Cyclo 3 , Y 1 , Y 2 , X 43 -X 48 , X 51 -X 54 , R 3 , and b3 are each as defined in claim 1, and * and *' respectively represent 1 binding site.

12. The organometallic compound according to claim 1, wherein L 2 is a ligand represented by one of formulae 1B(2)-1 to 1B(2)-6: in, In Formulae 1B(2)-1 to 1B(2)-6, R 30 and R 31 Each independently as claimed in claim 1 regarding R 3 As defined, b30 is an integer from 1 to 4. X 41 C(R 41 ) or N, and X 42 C(R 42 ) or N, R 41 and R 42 Each independently as claimed in claim 1 regarding R 4 As defined, Y 1 , Y 2 , X 43 -X 48 , and X 51 -X 54 each as defined in claim 1, and * and *' respectively represent 1 binding site.

13. The organometallic compound according to claim 12, wherein R 31 is C which is unsubstituted or substituted by at least one of the following 6 -C 30 Aryl or C 1 -C 30 Heteroaryl: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , C 1 -C 20 Alkyl, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or a combination thereof, and Q 1 -Q 3 Each independently is: -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 ; 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, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

14. The organometallic compound according to claim 1, wherein R 1 -R 4 , R 43 -R 48 , R 51 -R 54 , and R 61 -R 66 Each independently is: Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H.-CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , hydroxyl, cyano, nitro, amino, amidine, hydrazine, hydrazone, carboxylic acid or its salt, sulfonic acid or its salt, phosphoric acid or its salt, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio; 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; 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, 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, pyridyl, 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, -Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ), or a combination thereof; or -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 Q 1 -Q 9 Each independently is: -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 ; 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, C 1 -C 10 Alkyl, phenyl, or a combination thereof.

15. The organometallic compound according to claim 1, wherein the organometallic compound is one of Compounds 1 to 30:

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

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

19. The organic light emitting device according to claim 16, wherein The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the emission layer, and an electron transport region disposed between the emission layer and the second electrode, The hole transport region 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 16 to 19.

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