Organometallic compound, organic light-emitting device containing the same, and electronic device containing the organic light-emitting device

A heteroleptic organometallic compound is introduced as a dopant in the light-emitting layer of organic light-emitting devices, addressing the need for enhanced electrical properties and heat resistance, thereby improving device efficiency and longevity.

JP7828727B2Active Publication Date: 2026-03-12SAMSUNG DISPLAY CO LTD
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Patent Information

Authority / Receiving Office
JP · JP
Patent Type
Patents
Current Assignee / Owner
Filing Date
2021-05-19
Publication Date
2026-03-12

AI Technical Summary

Technical Problem

Existing organic light-emitting devices lack a novel organometallic compound that enhances electrical properties and heat resistance, leading to suboptimal performance in external quantum efficiency and device longevity.

Method used

The development of a heteroleptic organometallic compound represented by Chemical Formula 1, comprising a transition metal (M) with specific ligands (L1 and L2) and substituents, which serves as a dopant in the light-emitting layer of the organic layer, improving electrical properties and heat resistance.

Benefits of technology

The organometallic compound enhances the external quantum efficiency and life characteristics of organic light-emitting devices, resulting in high-quality electronic devices with improved performance.

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Abstract

To provide an organometallic compound and an organic light-emitting element including the organometallic compound, and an electronic apparatus including the organic light-emitting element.SOLUTION: An organometallic compound is represented by chemical formula 1, M(L1)n1(L2)n2. In chemical formula 1, explanations related to M, L1, L2, n1, and n2 are to be referred to descriptions in the specification.SELECTED DRAWING: Figure 1
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Description

[Technical Field]

[0001] The present invention relates to an organometallic compound, an organic light-emitting device containing the same, and an electronic device containing the organic light-emitting device. [Background technology]

[0002] An organic light emitting device is a self-luminous device that has excellent characteristics in terms of viewing angle, response time, brightness, driving voltage, and response speed, and is capable of being made multicolor.

[0003] According to one example, an organic light-emitting device has an anode, a cathode, and an organic layer including an emitting layer disposed between the anode and the cathode. A hole transport region is disposed between the anode and the emitting layer, and an electron transport region is disposed between the emitting layer and the cathode. Holes injected from the anode travel to the emitting layer via the hole transport region, and electrons injected from the cathode travel to the emitting layer via the electron transport region. The holes and electrons recombine in the emitting layer region to generate excitons. Light is generated as the excitons change from their excited state to their ground state. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-39713 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention has been made in view of the above-mentioned conventional techniques, and an object of the present invention is to provide a novel organometallic compound, an organic light-emitting element employing the same, and an electronic device including the organic light-emitting element. [Means for solving the problem]

[0006] In order to achieve the above object, an organometallic compound according to one embodiment of the present invention is represented by the following chemical formula 1. [Cation 1] M(L1) n1 (L2) n2 In the above Chemical Formula 1, M is a transition metal; L1 is a ligand represented by the following chemical formula 2A: L2 is a ligand represented by the following chemical formula 2B: n1 and n2 are each independently 1 or 2, and when n1 is 2, the two L1s are the same or different from each other, and when n2 is 2, the two L2s are the same or different from each other; the sum of n1 and n2 is 2 or 3, L1 and L2 are different from each other, [ka] [ka] In the formula 2A and the formula 2B, Y4 is C or N; X1 is Si or Ge; X 21 are O, S, S(=O), N(Z 29 ), C(Z 29 )(Z 30 ), or Si(Z 29 )(Z 30 ) and T1 to T4 are each independently C, N, a carbon bonded to ring CY1, or a carbon bonded to M in Chemical Formula 1, provided that one of T1 to T4 is a carbon bonded to M in Chemical Formula 1, and the remaining one of T1 to T4 that is not bonded to M is a carbon bonded to ring CY1; T5 to T8 are each independently C or N; In T1 to T8, the number of N is 0 or 1, Ring CY1 and Ring CY 14 are independent of each other, C5-C30 Carbocyclic group or C1-C 30 is a heterocyclic group, Ar2 is a ring CY2 substituted or unsubstituted with at least one Z0, and said ring CY2 is an unsaturated C5-C 30 Carbocyclic or unsaturated C1-C 30 is a heterocyclic group, R 21 ~R 23 are each independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1-C 20 Alkyl groups, C3-C 10 C1-C substituted or unsubstituted with cycloalkyl groups, phenyl groups, or any combination thereof 60 Alkyl group or C6-C 60 is an aryl group, Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C1-C 60 Alkylthio groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)( Q4 )(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); d2 is an integer of 1 to 6, and when d2 is 2 or more, two or more Ar2 are the same or different from each other; a1 and b1 are each independently an integer of 0 to 20; when a1 is 2 or more, two or more Z1 are the same or different; when b1 is 2 or more, two or more R 14 are the same as or different from each other, a2 is an integer of 0 to 5, and when a2 is 2 or more, two or more Z2 are the same or different; Satisfy the following <Condition 1> or <Condition 2>, <Condition 1> In the formula 2B, X1 is Si; In Formula 2B, R 12 But it is neither hydrogen nor a methyl group. In T1 to T8 of the above Chemical Formula 2A, the number of N is 0. <Condition 2> In Formula 2B, R 12 is hydrogen or R 12 The number of carbon atoms contained in R 21 ~R 23 two or more of which are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, Two or more of the plurality of Z1 are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, Two or more of the plurality of Z2 are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, R 12 and R 13 are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, Multiple R 14 two or more of which are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14 two or more of which may optionally be linked to each other and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, R 10a For details on R 14 See the explanation for In Chemical Formula 2A and Chemical Formula 2B, * and *' are binding sites with M in Chemical Formula 1, respectively; The substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl groups, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C1-C 60 Alkylthio groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic heterocyclic group are Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group or C1-C 60 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -Ge(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group or C1-C 60 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C1-C 60 Alkylthio groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q22 ), -Si(Q23)(Q 24 )(Q 25 ), -Ge(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof, substituted or unsubstituted, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -Ge(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or any combination thereof; and The Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amino group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; deuterium, C1-C 60 Alkyl groups, C6-C 60 C1-C substituted or unsubstituted aryl groups or any combination thereof 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10 Cycloalkyl groups; C1-C 10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl groups, C6-C 60 C6-C substituted or unsubstituted aryl groups or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 a heteroaryl group; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused polycyclic heterocyclic group.

[0007] According to another aspect, there is provided 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 and including an emitting layer, wherein the organic layer contains one or more of the organometallic compounds.

[0008] The organometallic compound is contained in a light-emitting layer of the organic layer, and the organometallic compound contained in the light-emitting layer serves as a dopant.

[0009] In yet another aspect, an electronic device is provided that includes the organic light emitting device. [Effects of the Invention]

[0010] The organometallic compounds of the present invention have excellent electrical properties and heat resistance, and electronic devices employing the organometallic compounds, such as organic light-emitting devices, have excellent external quantum efficiency (EQE) and excellent life characteristics. Therefore, by using the organometallic compounds, high-quality organic light-emitting devices and electronic devices including the same can be realized. [Brief explanation of the drawings]

[0011] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic light emitting device according to an embodiment; DETAILED DESCRIPTION OF THE INVENTION

[0012] Specific examples of embodiments of the present invention will be described in detail below.

[0013] The organometallic compound of the present invention is represented by the following Chemical Formula 1:

[0014] [Cation 1] M(L1) n1 (L2) n2

[0015] In the above formula 1, M is a transition metal.

[0016] For example, M is a period 1 transition metal, a period 2 transition metal, or a period 3 transition metal.

[0017] As other examples, M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).

[0018] According to one embodiment, M is Ir, Pt, Os, or Rh.

[0019] In the above Chemical Formula 1, L1 is a ligand represented by the following Chemical Formula 2A, and in the above Chemical Formula 1, n1 represents the number of L1 in the above Chemical Formula 1, and is 1 or 2. When n1 is 2, the two L1s are the same or different.

[0020] In the above Chemical Formula 1, L2 is a ligand represented by the following Chemical Formula 2B, and in the above Chemical Formula 1, n2 represents the number of L2 in the above Chemical Formula 1, and is 1 or 2. When n2 is 2, the two L2 are the same or different.

[0021] [ka]

[0022] [ka]

[0023] For an explanation of Chemical Formula 2A and Chemical Formula 2B, please refer to the following sections.

[0024] In the above formula 1, L1 and L2 are different from each other. That is, the organometallic compound represented by the above formula 1 is a heteroleptic complex.

[0025] According to one embodiment, in Formula 1, M is Ir and n1+n2 is 3, or M is Pt and n1+n2 is 2.

[0026] In other embodiments, M is Ir and i) n1 is 1 and n2 is 2, or ii) n1 is 2 and n2 is 1.

[0027] In the above formula 2B, Y4 is C or N.

[0028] For example, in the above formula 2B, Y4 is C.

[0029] In the above formula 2B, X1 is Si or Ge.

[0030] In the above formula 2A, X 21 are O, S, S(=O), N(Z 29 ), C(Z 29 )(Z 30 ), or Si(Z 29 )(Z 30 ) Z 29 and Z 30 For the explanation of each of the above, please refer to the respective sections described in this specification.

[0031] For example, in the above formula 2A, X 21 is O or S.

[0032] In the above Chemical Formula 2A, T1 to T4 are each independently C, N, a carbon bonded to ring CY1, or a carbon bonded to M in the above Chemical Formula 1, but one of T1 to T4 is a carbon bonded to M in the above Chemical Formula 1, and one of the remaining T1 to T4 not bonded to M is a carbon bonded to ring CY1, and T5 to T8 are each independently C or N.

[0033] In T1 to T8 of the above Chemical Formula 2A, the number of N is 0 or 1.

[0034] In the above chemical formula 2A and the above chemical formula 2B, ring CY1 and ring CY 14 are independent of each other, C5-C 30 Carbocyclic group or C1-C 30 In the above formula 2A, Ar2 is a ring CY2 substituted or unsubstituted with at least one Z0, and the ring CY2 is an unsaturated C5-C 30 Carbocyclic or unsaturated C1-C 30 It is a heterocyclic group. For the explanation of Z0, please refer to the parts described in this specification.

[0035] According to one embodiment, in Formula 2A and Formula 2B, the ring CY1 and the ring CY 14are, independently of one another, a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, or a benzogermole group. , benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoline and xaline, quinazoline, phenanthroline, pyrrole, pyrazole, imidazole, triazole, oxazole, isoxazole, thiazole, isothiazole, oxadiazole, thiadiazole, benzopyrazole, benzimidazole, benzoxazole, benzothiazole, benzoxadiazole, benzothiadiazole, 5,6,7,8-tetrahydroisoquinoline, 5,6,7,8-tetrahydroquinoline, adamantane, norbornane, or norbornene.

[0036] According to another embodiment, ring CY1 and ring CY 14 are each independently a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine 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.

[0037] According to still another embodiment, in Formula 2A, ring CY1 is a pyridine group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0038] According to yet another embodiment, in Formula 2B, the ring CY 14 is a benzene group, a naphthalene group, a 1,2,3,4-tetrahydronaphthalene group, a phenanthrene group, a dibenzothiophene group, a dibenzofuran group, or a pyridine group.

[0039] According to still another embodiment, the ring CY2 may be a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a silole group, a germole group, a selenophene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, or a benzofuran group. group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group Nophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group a phosphorus group, a quinoxaline group, a quinazoline group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0040] In the above formula 2B, R 21 ~R 23are each independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1-C 20 Alkyl groups, C3-C 10 C1-C substituted or unsubstituted with cycloalkyl groups, phenyl groups, or any combination thereof 60 Alkyl group or C6-C 60 It is an aryl group.

[0041] For example, in Formula 2B above, R 21 ~R 23 are each independently deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1-C 20 Alkyl groups, C3-C 10 and cycloalkyl groups, phenyl groups, or any combination thereof, substituted or unsubstituted, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, tert-decyl, phenyl, biphenyl, or naphthyl groups.

[0042] According to one embodiment, in Formula 2B, R 21 ~R 23are each independently -CH3, -CH2CH3, -CD3, -CD2H, -CDH2, -CH2CD3, or -CD2CH3.

[0043] According to another embodiment, in Formula 2B, R 21 ~R 23 are identical to each other.

[0044] According to yet another embodiment, in Formula 2B, R 21 ~R 23 Two or more of them are different from each other.

[0045] In the above chemical formula 2A and the above chemical formula 2B, Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a substituted or unsubstituted C1-C 60 Alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl groups, substituted or unsubstituted C2-C 60 Alkynyl groups, substituted or unsubstituted C1-C 60 Alkoxy groups, substituted or unsubstituted C1-C 60 Alkylthio groups, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 Cycloalkenyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkenyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60Heteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -N(Q1)(Q2), -Si(Q3)( Q4 )(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9). For explanations of Q1 to Q9, please refer to the sections described in this specification.

[0046] In Formula 2A, d2 represents the number of Ar2 and is an integer from 1 to 6. When d2 is 2 or greater, the two or more Ar2s may be the same or different. For example, d2 is 1, 2, or 3. According to one embodiment, d2 is 1 or 2.

[0047] In the above Chemical Formula 2A and the above Chemical Formula 2B, a1 and b1 are Z1 and R 14 and each independently represents an integer of 0 to 20. When a1 is 2 or more, two or more Z1 are the same or different from each other. When b1 is 2 or more, two or more R 14 are the same as or different from each other. For example, a1 and b1 are each independently an integer of 0 to 10.

[0048] In the above Chemical Formula 2A, a2 represents the number of Z2 and is an integer of 0 to 5. When a2 is 2 or more, the two or more Z2 are the same or different. For example, a2 is 0, 1, 2, or 3.

[0049] According to one embodiment, Z1 in Formula 2A and R 11 ~R 13 are each independently Hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C3-C 10Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluorinated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C1-C alkyl)biphenyl groups, or any combination thereof, substituted or unsubstituted 20 an alkyl group; or Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl groups, fluorinated C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, deuterated C1-C 20 Alkoxy group, fluorinated C1-C 20 Alkoxy groups, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluorinated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C20 C3-C alkyl)biphenyl groups, substituted or unsubstituted with any combination thereof 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group;

[0050] According to another embodiment, Z1 in Formula 2A and R 11 ~R 13 are each independently hydrogen or deuterium; Deuterium, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, (C1-C 20 C1-C alkyl)biphenyl groups, or any combination thereof, substituted or unsubstituted 20 an alkyl group; or Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, deuterated C1-C 20 Alkoxy groups, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, (C1-C 20 C3-C alkyl)biphenyl groups, substituted or unsubstituted with any combination thereof 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group;

[0051] According to still another embodiment, Z0 and Z2 in Formula 2A and R 14 are each independently Hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluorinated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C1-C alkyl)biphenyl groups, or any combination thereof, substituted or unsubstituted 20 alkyl groups; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl groups, fluorinated C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, deuterated C1-C 20 Alkoxy group, fluorinated C1-C 20 Alkoxy groups, C3-C 10Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluorinated C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl Groups, Deuterated C1-C 10 Heterocycloalkyl groups, fluorinated C1-C 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C3-C alkyl)biphenyl groups, substituted or unsubstituted with any combination thereof 10 Cycloalkyl groups, C1-C 10 a heterocycloalkyl group, a phenyl group, or a biphenyl group; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5);

[0052] According to still another embodiment, in Formula 2A and Formula 2B, Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group or C1-C 20 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantanyl groups, norbornanyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, bicyclo[2.2.2]octyl groups, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 C1-C substituted with alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 20 Alkyl groups, C1-C 20 Alkoxy group or C1-C 20 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, (phenyl) C1-C 10 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzisothiazolyl group, benzo a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, (C1-C 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinox a salinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group; or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); Q1 to Q9 are each independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Deuterium, C1-C 10 an alkyl group, a phenyl group, or any combination thereof, substituted or unsubstituted, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl;

[0053] According to still another embodiment, in Formula 2A and Formula 2B, R 21 ~R 23 , Z1, Z2, and R 11 ~R 14 does not contain silicon (Si), thereby improving the out-coupling characteristics of an electronic device, such as an organic light-emitting device, including the organometallic compound represented by Chemical Formula 1.

[0054] According to still another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies at least one of the following <Condition A> to <Condition C>.

[0055] <Condition A> In the above formula 2A, Z1 is not hydrogen and a1 is not 0. <Condition B> In the above formula 2A, Z2 is not hydrogen and a2 is not 0. <Condition C> In the above formula 2B, R 14 is not hydrogen and b1 is not 0.

[0056] The organometallic compound represented by the above chemical formula 1 satisfies the following <Condition 1> or <Condition 2>.

[0057] <Condition 1> In the above formula 2B, X1 is Si; In the above formula 2B, R 12 But it is neither hydrogen nor a methyl group. In T1 to T8 of the above Chemical Formula 2A, the number of N is 0. <Condition 2> In the above formula 2B, R 12 is hydrogen or R 12 The number of carbon atoms contained in R 12 is hydrogen, a methyl group, or a deuterated methyl group (e.g., -CH2D, -CHD2, or -CD3).

[0058] According to one embodiment, the organometallic compound represented by Chemical Formula 1 satisfies the above <Condition 1>.

[0059] According to another embodiment, the organometallic compound represented by Formula 1 satisfies the above <Condition 1> and R 12 The number of carbon atoms contained in is two or more.

[0060] According to yet another embodiment, the organometallic compound represented by Formula 1 satisfies the above <Condition 1>, and in Formula 2B, R 12 teeth, C2-C 20 Alkyl group or C2-C 20 Alkoxy groups; C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 a methyl group or a methoxy group substituted with a heterocycloalkenyl group, a C6-C14 aryl group, a C1-C14 heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups, C1-C 10 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 14 Aryl groups, C1-C 14 C-C substituted with a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof 20 Alkyl group or C2-C 20 an alkoxy group; or Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, C1-C 20 Alkoxy groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 14 Aryl groups, C1-C 14 C3-C substituted or unsubstituted heteroaryl groups, monovalent non-aromatic fused polycyclic groups, monovalent non-aromatic fused heteropolycyclic groups, or any combination thereof 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 14 Aryl groups, C1-C 14 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused polycyclic heterocyclic group;

[0061] According to yet another embodiment, the organometallic compound represented by Formula 1 satisfies the above <Condition 1>, and in Formula 2B, R 12 teeth, Cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 alkyl) a methyl or methoxy group substituted with a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof; i) cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 alkyl) a phenyl group, a naphthyl group, a pyridinyl group, a pyrimidinyl group, or any combination thereof, and ii) a methyl group or a methoxy group substituted with at least one deuterium; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, cyclopentyl groups, cyclohexyl groups, cycloheptyl groups, cyclooctyl groups, adamantanyl groups, norbornanyl groups, norbornenyl groups, cyclopentenyl groups, cyclohexenyl groups, cycloheptenyl groups, bicyclo[1.1.1]pentyl groups, bicyclo[2.1.1]hexyl groups, bicyclo[2.2.2]octyl groups, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 C2-C alkyl) substituted or unsubstituted with phenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof 20 Alkyl group or C2-C 20an alkoxy group; or Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 alkyl)cyclopentyl group, (C1-C 20 alkyl)cyclohexyl group, (C1-C 20 alkyl)cycloheptyl group, (C1-C 20 alkyl)cyclooctyl group, (C1-C 20 alkyl)adamantanyl group, (C1-C 20 alkyl)norbornanyl group, (C1-C 20 alkyl)norbornenyl group, (C1-C 20 alkyl)cyclopentenyl group, (C1-C 20 alkyl)cyclohexenyl group, (C1-C 20 alkyl)cycloheptenyl group, (C1-C 20 alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, benzisothiazolyl group, benzo a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a cyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, a bicyclo[1.1.1]pentyl group, a bicyclo[2.1.1]hexyl group, a bicyclo[2.2.2]octyl group, a phenyl group, (C1-C 20alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, isoindolyl group, indolyl group, indazolyl group, purinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxa a cinnolinyl group, a quinazolinyl group, a cinnolinyl group, a carbazolyl group, a phenanthrolinyl group, a benzimidazolyl group, a benzofuranyl group, a benzothiophenyl group, a benzisothiazolyl group, a benzoxazolyl group, a benzisoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group;

[0062] According to yet another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies the above <Condition 2>.

[0063] According to yet another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies Condition 2, where X1 in Chemical Formula 2B is Si, and the number of N in T1 to T8 in Chemical Formula 2A is 0.

[0064] According to yet another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies Condition 2, where X1 in Chemical Formula 2B is Ge, and the number of N in T1 to T8 in Chemical Formula 2A is 0.

[0065] According to yet another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies Condition 2, where X1 in Chemical Formula 2B is Si, and the number of N in T1 to T8 in Chemical Formula 2A is 1.

[0066] According to yet another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies Condition 2, wherein X1 in Chemical Formula 2B is Ge, and the number of N in T1 to T8 in Chemical Formula 2A is 1.

[0067] According to yet another embodiment, the organometallic compound represented by Formula 1 satisfies the above <Condition 2> and R 12 contains at least one deuterium.

[0068] According to still another embodiment, the organometallic compound represented by Formula 1 includes at least one deuterium, at least one fluoro group (—F), at least one cyano group (—CN), or any combination thereof.

[0069] According to yet another embodiment, the organometallic compound represented by Formula 1 contains at least one deuterium atom.

[0070] According to still another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies at least one of the following <Condition (1)> to <Condition (6)>, or satisfies the following <Condition (7)>:

[0071] <Condition (1)> In the above chemical formula 2A, a1 is not 0, and at least one of the a1 Z1s contains deuterium. <Condition (2)> In the above chemical formula 2A, a2 is not 0, and at least one of the a2 Z2s contains a deuterium atom, a fluoro group (-F), a cyano group, or any combination thereof. <Condition (3)> In the above formula 2A, at least one of the d2 Ar2s contains a deuterium atom, a fluoro group (-F), a cyano group, or any combination thereof. <Condition (4)> R in the above chemical formula 2B 21 ~R 23 At least one of them contains deuterium <Condition (5)> In the above formula 2B, R 12 contains at least one deuterium <Condition (6)> In the above chemical formula 2B, b1 is not 0, and b1 R 14 At least one of the groups contains deuterium, a fluoro group (-F), a cyano group, or any combination thereof. <Condition (7)> In the above formula 2A, Z1, Z2, and Ar2, and in the above formula 2B, R 11 ~R 14 , and R 21 ~R 23 Each of these consists of only carbon and hydrogen.

[0072] According to still another embodiment, in Formula 2A and Formula 2B, Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14are each independently hydrogen, deuterium, -F, a cyano group, a nitro group, -SF5, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, -OCH3, -OCDH2, -OCD2H, -OCD3, -SCH3, -SCDH2, -SCD2H, -SCD3, a group represented by one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulas 9-201 to 9-230, a group in which at least one hydrogen of one of the following chemical formulas 9-201 to 9-230 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulas 10-1 to 10-145 has been substituted with deuterium; a group in which at least one hydrogen atom in one of the following chemical formulas 10-1 to 10-145 has been substituted with -F; a group in which at least one hydrogen atom in one of the following chemical formulas 10-1 to 10-145 has been substituted with -F; a group in which at least one hydrogen atom in one of the following chemical formulas 10-201 to 10-354 has been substituted with deuterium; a group in which at least one hydrogen atom in one of the following chemical formulas 10-201 to 10-354 has been substituted with -F; -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (for explanations of Q3 to Q5, please refer to the respective sections described in this specification).

[0073] According to still another embodiment, Z1 in Formula 2A and R 11 ~R 13are each independently hydrogen, deuterium, -CH3, -CD3, -CD2H, -CDH2, -OCH3, -OCDH2, -OCD2H, -OCD3, -SCH3, -SCDH2, -SCD2H, -SCD3, a group represented by one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen in one of the following chemical formulas 9-1 to 9-39 has been substituted with deuterium, a group represented by one of the following chemical formulas 9-201 to 9-230, a group in which at least one hydrogen in one of the following chemical formulas 9-201 to 9-230 has been substituted with deuterium, a group represented by one of the following chemical formulas 10-1 to 10-138 and 10-145, or a group in which at least one hydrogen in one of the following chemical formulas 10-1 to 10-138 and 10-145 has been substituted with deuterium.

[0074] According to still another embodiment, Ar2 in Chemical Formula 2A is a group represented by one of the following Chemical Formulas 10-12 to 10-145, a group in which at least one hydrogen in one of the following Chemical Formulas 10-12 to 10-145 is substituted with deuterium, a group in which at least one hydrogen in one of the following Chemical Formulas 10-12 to 10-145 is substituted with -F, a group represented by one of the following Chemical Formulas 10-201 to 10-354, a group in which at least one hydrogen in one of the following Chemical Formulas 10-201 to 10-354 is substituted with deuterium, or a group in which at least one hydrogen in one of the following Chemical Formulas 10-201 to 10-354 is substituted with -F.

[0075] According to yet another embodiment, in Formula 2B, R 12 is hydrogen, -CH3, -CH2D, -CHD2, or -CD3.

[0076] According to yet another embodiment, in Formula 2B, R 12 is a hydrogen or a methyl group (-CH3).

[0077] According to yet another embodiment, in Formula 2B, R 12 is -CH2D, -CHD2, or -CD3.

[0078] According to yet another embodiment, in Formula 2B, R 12 represents a group represented by one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulas 9-201 to 9-230, a group in which at least one hydrogen atom in one of the following chemical formulas 9-201 to 9-230 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulas 9-201 to 9-230 is substituted with -F ...10-1 a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen atom is substituted with deuterium; a group represented by one of the following chemical formulas 10-1 to 10-145 in which at least one hydrogen atom is substituted with —F; a group represented by one of the following chemical formulas 10-201 to 10-354 in which at least one hydrogen atom is substituted with deuterium; or a group represented by one of the following chemical formulas 10-201 to 10-354 in which at least one hydrogen atom is substituted with —F.

[0079] [ka]

[0080] [ka]

[0081] [ka] [ka] [ka]

[0082] [ka] [ka] [ka] [ka]

[0083] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-230, 10-1 to 10-145, and 10-201 to 10-354, * denotes a bonding site with an adjacent atom, Ph denotes a phenyl group, TMS denotes a trimethylsilyl group, TMG denotes a trimethylgermyl group, and OMe denotes a methoxy group.

[0084] The above "group in which at least one hydrogen atom in one of chemical formulas 9-1 to 9-39 has been substituted with deuterium" and "group in which at least one hydrogen atom in one of chemical formulas 9-201 to 9-230 has been substituted with deuterium" are, for example, groups represented by the following chemical formulas 9-501 to 9-514 and 9-601 to 9-637.

[0085] [ka]

[0086] [ka]

[0087] The above "group in which at least one hydrogen atom of one of chemical formulas 9-1 to 9-39 is substituted with -F" and "group in which at least one hydrogen atom of one of chemical formulas 9-201 to 9-230 is substituted with -F" are, for example, groups represented by the following chemical formulas 9-701 to 9-710.

[0088] [ka]

[0089] The above "group in which at least one hydrogen atom in one of chemical formulas 10-1 to 10-145 has been substituted with deuterium" and "group in which at least one hydrogen atom in one of chemical formulas 10-201 to 10-354 has been substituted with deuterium" are, for example, groups represented by the following chemical formulas 10-501 to 10-553.

[0090] [ka] [ka]

[0091] The above "group in which at least one hydrogen atom of one of chemical formulas 10-1 to 10-145 is substituted with -F" and "group in which at least one hydrogen atom of one of chemical formulas 10-201 to 10-354 is substituted with -F" are, for example, groups represented by the following chemical formulas 10-601 to 10-636.

[0092] [ka]

[0093] In the above Chemical Formula 2A and the above Chemical Formula 2B, i) R 21 ~R 23 two or more of which are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 ii) two or more of the plurality of Z1 are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10aSubstituted or unsubstituted C1-C 30 iii) two or more of the plurality of Z2 are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, and iv) R 12 and R 13 and optionally linked together, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, and v) a plurality of R 14 two or more of which are optionally linked to each other, and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 vi) Z0, Z1, Z2, Z 29 , Z 30 , and R 11 ~R 14 two or more of which may optionally be linked to each other and at least one R 10a Substituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 Forms a heterocyclic group.

[0094] As used herein, R 10a The description of R 14 See the explanation about.

[0095] In the above Chemical Formula 2A and Chemical Formula 2B, * and *' are binding sites with M in the above Chemical Formula 1, respectively.

[0096] According to one embodiment, in Formula 2A, [ka] The group represented by the formula is a group represented by one of the following chemical formulas CY1(1) to CY1(16).

[0097] [ka]

[0098] In the above chemical formulas CY1(1) to CY1(16), * is the bonding site with M in the above chemical formula 1, *" is a binding site for one of T1 to T4 in the above chemical formula 2A.

[0099] According to another embodiment, in Formula 2A, [ka] The group represented by the following formula CY1-1 to CY1-28 is a group represented by one of the following formulas CY1-1 to CY1-28.

[0100] [ka]

[0101] In the above chemical formulas CY1-1 to CY1-28, Z 11 ~Z 14 Although the description of each of Z1 and Z2 in this specification refers to the description of Z1, 11 ~Z 14 Each of these is not hydrogen, Ring CY 10a is C5-C 30 Carbocyclic group or C1-C 30 is a heterocyclic group, R 10a For a description of aa is an integer from 0 to 10, * is the bonding site with M in the above chemical formula 1, *" is a binding site for one of T1 to T4 in the above chemical formula 2A.

[0102] For example, the ring CY 10a is a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.

[0103] According to yet another embodiment, in Formula 2A, [ka] is a group represented by one of the above chemical formulas CY1-1, CY1-4, CY1-7, CY1-9, CY1-11, CY1-12, and CY1-14 to CY1-24.

[0104] According to yet another embodiment, in Formula 2A, [ka] The group represented by the formula: is a group represented by one of the following chemical formulas CY2-1 to CY2-6.

[0105] [ka]

[0106] In the above chemical formulas CY2-1 to CY2-6, T1 to T8 are each independently C or N, but in T3 to T8 of the above chemical formula CY2-1 and chemical formula CY2-6, the number of N is 0 or 1, in T1, T2, T5, T6, T7, and T8 of the above chemical formula CY2-2 and chemical formula CY2-5, the number of N is 0 or 1, and in T1, T4, T5, T6, T7, and T8 of the above chemical formula CY2-3 and chemical formula CY2-4, the number of N is 0 or 1, X 21 For a description of *" is the binding site with ring CY1 in the above chemical formula 2A, *' is the bonding site with M in the above chemical formula 1.

[0107] For example, in the organometallic compound represented by the above chemical formula 1, in the above chemical formula 2A, [ka] is a group represented by one of the above chemical formulas CY2-1 to CY2-6, a) X1 in the above chemical formula 2B is Si, and in the above chemical formula 2B, R 12 is neither hydrogen nor a methyl group, and in T1 to T8 of the above chemical formulas CY2-1 to CY2-6, the number of N is 0, or b) X1 in the above formula 2B is Si or Ge, and R 12 is hydrogen, a methyl group, or a deuterated methyl group, and in T1 to T8 of the above chemical formulas CY2-1 to CY2-6, the number of N is 0, or c) X1 in the above formula 2B is Si or Ge, and R 12 is hydrogen, a methyl group, or a deuterated methyl group, and in T3 to T8 of the above chemical formula CY2-1 and chemical formula CY2-6, the number of N is 1, or d) X1 in the above formula 2B is Si or Ge, and in the above formula 2B, R 12 is hydrogen, a methyl group, or a deuterated methyl group, and in T1, T2, T5, T6, T7, and T8 of the above chemical formula CY2-2 and chemical formula CY2-5, the number of N is 1, or e) X1 in the above formula 2B is Si or Ge, and in the above formula 2B, R 12 is hydrogen, a methyl group, or a deuterated methyl group, and the number of N is 1 in T1, T4, T5, T6, T7, and T8 of the above chemical formula CY2-3 and chemical formula CY2-4.

[0108] According to yet another embodiment, in Formula 2A, [ka] The group represented by the formula is a group represented by one of the following chemical formulas CY2(1) to CY2(6).

[0109] [ka]

[0110] In the above chemical formulas CY2(1) to CY2(6), T 21 is N, C(Z 21 ), or C(Ar 21 ) and T 22 is N, C(Z 22 ), or C(Ar 22 ) and T 23 is N, C(Z 23 ), or C(Ar 23 ) and T 24 is N, C(Z 24 ), or C(Ar 24 ) and T 25 is N, C(Z 25 ), or C(Ar 25 ) and T 26 is N, C(Z 26 ), or C(Ar 26 ) and T 27 is N, C(Z 27 ), or C(Ar 27 ) and T 28 is N, C(Z 28 ), or C(Ar 28 ) and In T3 to T8 of the above chemical formula CY2-1 and chemical formula CY2-6, the number of N is 0 or 1; in T1, T2, T5, T6, T7, and T8 of the above chemical formula CY2-2 and chemical formula CY2-5, the number of N is 0 or 1; and in T1, T4, T5, T6, T7, and T8 of the above chemical formula CY2-3 and chemical formula CY2-4, the number of N is 0 or 1; X 21 For a description of Z 21 ~Z 28For the explanation of each of the above, please refer to the explanation of Z2 in this specification. Ar 21 ~Ar 28 For the explanation of each of the above, please refer to the explanation of Ar2 in this specification. The above chemical formulas CY2-1 and CY2-6 are Ar 23 ~Ar 28 wherein the chemical formula CY2-2 and the chemical formula CY2-5 are each independently selected from the group consisting of Ar 21 , Ar 22 , Ar 25 , Ar 26 , Ar 27 , and Ar 28 wherein the chemical formula CY2-3 and the chemical formula CY2-4 are Ar 21 , Ar 24 , Ar 25 , Ar 26 , Ar 27 , and Ar 28 and *" is the binding site with ring CY1 in the above chemical formula 2A, *' is the bonding site with M in the above chemical formula 1.

[0111] According to yet another embodiment, in Formula 2A, [ka] is a group represented by one of the following chemical formulas CY2(1) to CY2(6), and satisfies at least one of the following <Condition 1-1> to <Condition 1-8>.

[0112] <Condition 1-1> In the above chemical formula CY2(1)~chemical formula CY2(6), T 28 is C(Ar 28 ) <Condition 1-2> In the above chemical formula CY2(1)~chemical formula CY2(6), T 27 is C(Ar 27 ) <Condition 1-3> In the above chemical formula CY2(1)~chemical formula CY2(6), T 26 is C(Ar 26 ) <Condition 1-4> In the above chemical formula CY2(1)~chemical formula CY2(6), T 25 is C(Ar 25 ) <Condition 1-5> In the above chemical formulas CY2(1), CY2(3), CY2(4), and CY2(6), T 24 is C(Ar 24 ) <Condition 1-6> In the above chemical formulas CY2(1) and CY2(6), T 23 is C(Ar 23 ) <Condition 1-7> In the above chemical formula CY2(2) and chemical formula CY2(5), T 22 is C(Ar 22 ) <Condition 1-8> In the above chemical formula CY2(2)~chemical formula CY2(5), T 21 is C(Ar 21 )

[0113] According to yet another embodiment, in Formula 2A, [ka] is a group represented by one of the following chemical formulas CY2(1) to CY2(6), and satisfies at least one of the following <Condition 2-1> to <Condition 2-8>.

[0114] <Condition 2-1> In the above chemical formula CY2(1)~chemical formula CY2(6), T 28 is C(Z 28 ) and Z 28 is not hydrogen <Condition 2-2> In the above chemical formula CY2(1)~chemical formula CY2(6), T 27 is C(Z 27 ) and Z 27 is not hydrogen <Condition 2-3> In the above chemical formula CY2(1)~chemical formula CY2(6), T 26 is C(Z 26 ) and Z 26 is not hydrogen <Condition 2-4> In the above chemical formula CY2(1)~chemical formula CY2(6), T 25 is C(Z 25 ) and Z 25 is not hydrogen <Condition 2-5> In the above chemical formulas CY2(1), CY2(3), CY2(4), and CY2(6), T 24 is C(Z 24 ) and Z 24 is not hydrogen <Condition 2-6> In the above chemical formulas CY2(1) and CY2(6), T 23 is C(Z 23 ) and Z 23 is not hydrogen <Condition 2-7> In the above chemical formula CY2(2) and chemical formula CY2(5), T 22 is C(Z 22 ) and Z 22 is not hydrogen <Condition 2-8> In the above chemical formula CY2(2)~chemical formula CY2(5), T 21 is C(Z 21 ) and Z 21 is not hydrogen.

[0115] According to yet another embodiment, in Formula 2A, [ka] is a group represented by one of the following chemical formulas CY2(1) to CY2(6), and satisfies one of the following <condition 3-1> to <condition 3-9>.

[0116] <Condition 3-1> T of the above chemical formulas CY2(1) to CY2(6) 21 ~T 28are not N <Condition 3-2> In the above chemical formula CY2(1)~chemical formula CY2(6), T 28 is N <Condition 3-3> In the above chemical formula CY2(1)~chemical formula CY2(6), T 27 is N <Condition 3-4> In the above chemical formula CY2(1)~chemical formula CY2(6), T 26 is N <Condition 3-5> In the above chemical formula CY2(1)~chemical formula CY2(6), T 25 is N <Condition 3-6> In the above chemical formulas CY2(1), CY2(3), CY2(4), and CY2(6), T 24 is N <Condition 3-7> In the above chemical formula CY2(1) and chemical formula CY2(6), T 23 is N <Condition 3-8> In the above chemical formula CY2(2) and chemical formula CY2(5), T 22 is N <Condition 3-9> In the above chemical formula CY2(2)~chemical formula CY2(5), T 21 is N.

[0117] According to still another embodiment, the group represented by the chemical formula CY2(1) is a group represented by one of the following chemical formulas CY2(1)-1 to CY2(1)-4, the group represented by the chemical formula CY2(2) is a group represented by one of the following chemical formulas CY2(2)-1 to CY2(2)-4, the group represented by the chemical formula CY2(3) is a group represented by one of the following chemical formulas CY2(3)-1 to CY2(3)-3, the group represented by the chemical formula CY2(4) is a group represented by one of the following chemical formulas CY2(4)-1 to CY2(4)-3, the group represented by the chemical formula CY2(5) is a group represented by one of the following chemical formulas CY2(5)-1 to CY2(5)-4, and the group represented by the chemical formula CY2(6) is a group represented by one of the following chemical formulas CY2(6)-1 to CY2(6)-4.

[0118] [ka]

[0119] [ka]

[0120] [ka]

[0121] In the above chemical formulas CY2(1)-1 to CY2(1)-4, the above chemical formulas CY2(2)-1 to CY2(2-4), the above chemical formulas CY2(3)-1 to CY2(3)-3, the above chemical formulas CY2(4)-1 to CY2(4-3), the above chemical formulas CY2(5)-1 to CY2(5)-4, and the above chemical formulas CY2(6)-1 to CY2(6-4, T 21 ~T 28 , X 21 For the explanation of *", *", and *', please refer to the explanation of the above chemical formulas CY2(1) to CY2(6) in this specification. Ring CY20a is C5-C 30 Carbocyclic group or C1-C 30 is a heterocyclic group, R 10a For a description of aa is an integer from 0 to 10.

[0122] For example, the ring CY 20a is a cyclohexane group, a norbornane group, a benzene group, or a naphthalene group.

[0123] According to yet another embodiment, in Formula 2A, [ka] is a group represented by one of the following chemical formulas CY2-1-1 to CY2-1-65, CY2-2-1 to CY2-2-65, CY2-3-1 to CY2-3-65, CY2-4-1 to CY2-4-65, CY2-5-1 to CY2-5-65, and CY2-6-1 to CY2-6-65.

[0124] [ka] [ka]

[0125] [ka] [ka]

[0126] [ka] [ka]

[0127] [ka] [ka]

[0128] [ka] [ka]

[0129] [ka] [ka]

[0130] In the above chemical formulas CY2-1-1 to CY2-1-65, the above chemical formulas CY2-2-1 to CY2-2-65, the above chemical formulas CY2-3-1 to CY2-3-65, the above chemical formulas CY2-4-1 to CY2-4-65, the above chemical formulas CY2-5-1 to CY2-5-65, and the above chemical formulas CY2-6-1 to CY2-6-65, X 21 For a description of Z 21 ~Z 28 Although the description of each of Z2 in this specification refers to the description of Z2, 21 ~Z 28 Each of these is not hydrogen, Ar 21 ~Ar 28 For the explanation of each of the above, please refer to the explanation of Ar2 in this specification. *" is the binding site with ring CY1 in the above chemical formula 2A, *' is the bonding site with M in the above chemical formula 1.

[0131] According to yet another embodiment, in Formula 2B, [ka] The group represented by the formula: is a group represented by one of the following chemical formulas CY14-1 to CY14-64.

[0132] [ka] [ka]

[0133] In the above chemical formulas CY14-1 to CY14-64, X 14a is O, S, N, C, or Si, *" is a bonding site with the carbon atom of the adjacent pyridine ring in the above chemical formula 2B, *' is the bonding site with M in the above chemical formula 1. In the above chemical formulas CY14-1 to CY14-64, Carbon and X 14a each of which is an R 14 is substituted or unsubstituted.

[0134] According to yet another embodiment, in Formula 2B, [ka] The group represented by the formula is a group represented by one of the following chemical formulas CY14(1) to CY14(63).

[0135] [ka] [ka]

[0136] In the above chemical formulas CY14(1) to CY14(63), R14a ~R 14d The explanations regarding R 14 Although the explanation of R 14a ~R 14d Each of these is not hydrogen, X 14 is C(R1)(R2), N(R1), O, S, or Si(R1)(R2), The explanations for R1 to R8 are as follows in this specification: 14 See the explanation for *" is a bonding site with the carbon atom of the adjacent pyridine ring in the above chemical formula 2B, *' is the bonding site with M in the above chemical formula 1.

[0137] According to still another embodiment, the organometallic compound represented by Formula 1 has one or two silicon (Si) atoms.

[0138] According to yet another embodiment, the organometallic compound is one of the following compounds 1 to 5140: [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0139] In the organometallic compound represented by Chemical Formula 1, L1 is a ligand represented by Chemical Formula 2A, where n1, the number of L1, is 1 or 2, and L2 is a ligand represented by Chemical Formula 2B, where n2, the number of L2, is 1 or 2, and L1 and L2 are different from each other. That is, the organometallic compound is a ligand bonded to a metal M, and is a heteroleptic complex that necessarily contains at least one ligand represented by Chemical Formula 2A and at least one ligand represented by Chemical Formula 2B.

[0140] In the above chemical formula 1, *-X1(R 21 )(R 22 )(R 23) is bonded to the 5-position of the pyridine ring in the ligand represented by Chemical Formula 2B (see Chemical Formula 2B). As a result, the organometallic compound containing the ligand represented by Chemical Formula 2B has excellent heat resistance and decomposition resistance, and electronic devices employing the same, such as organic light-emitting devices, have high stability and long life during fabrication, storage, and / or operation.

[0141] In the above formula 2A of formula 1, Ar2 is a ring CY2 substituted or unsubstituted with at least one Z0, and the ring CY2 is an unsaturated C5-C 30 Carbocyclic or unsaturated C1-C 30 d2, which is a heterocyclic group and is the number of Ar2, is an integer of 1 to 6. As a result, the photoalignment properties of the organometallic compound represented by Chemical Formula 1 are improved, the full width at half maximum (FWHM) of the emission spectrum or electroluminescence spectrum of the organometallic compound represented by Chemical Formula 1 becomes relatively small, and the luminous efficiency of an electronic device, such as an organic light-emitting device, employing the organometallic compound represented by Chemical Formula 1 is improved.

[0142] In addition, in T1 to T8 of Chemical Formula 2A of Chemical Formula 1, the number of N is 0 or 1. As a result, the organometallic compound represented by Chemical Formula 1 has stable HOMO (highest occupied molecular orbital) energy level and LUMO (lowest unoccupied molecular orbital) energy level, and the lifetime of an electronic device, such as an organic light-emitting device, employing this organometallic compound is improved.

[0143] The HOMO energy level, LUMO energy level, S1 energy level, and T1 energy level of some organometallic compounds represented by the above chemical formula 1 were evaluated using the Gaussian09 program with molecular structure optimization by density functional theory (DFT) based on B3LYP. The results are shown in Table 1 below.

[0144] [Table 1]

[0145] From Table 1 above, it can be seen that the organometallic compound represented by Chemical Formula 1 above has electrical properties suitable for use as a dopant in electronic devices, for example, organic light emitting devices.

[0146] Those skilled in the art will be able to recognize how to synthesize the organometallic compound represented by Chemical Formula 1 above by referring to the synthesis examples described below.

[0147] Therefore, the organometallic compound represented by Chemical Formula 1 is suitable for use as a dopant in an organic layer of an organic light-emitting device, for example, an emission layer in the organic layer. According to another aspect, there is provided an organic light-emitting device having a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer contains at least one organometallic compound represented by Chemical Formula 1.

[0148] The organic light emitting device has an organic layer containing the organometallic compound represented by Chemical Formula 1 as described above, and thus has high external quantum efficiency and long life characteristics.

[0149] The organometallic compound represented by Chemical Formula 1 is used between a pair of electrodes of an organic light-emitting device. For example, the organometallic compound represented by Chemical Formula 1 is included in an emission layer. Here, the organometallic compound acts as a dopant, and the emission layer further includes a host (i.e., the content of the organometallic compound represented by Chemical Formula 1 is less than the content of the host). The emission layer emits, for example, green light or blue light.

[0150] In this specification, the phrase "(the organic layer) contains one or more organometallic compounds" is interpreted as "(the organic layer) contains one organometallic compound belonging to the category of Chemical Formula 1 above, or two or more different organometallic compounds belonging to the category of Chemical Formula 1 above."

[0151] For example, the organic layer contains only Compound 1 as an organometallic compound. In this case, Compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer contains Compound 1 and Compound 2 as organometallic compounds. Here, Compound 1 and Compound 2 are present in the same layer (for example, Compound 1 and Compound 2 are both present in the light-emitting layer).

[0152] The first electrode is an anode that is a hole-injecting electrode and the second electrode is a cathode that is an electron-injecting electrode, or the first electrode is a cathode that is an electron-injecting electrode and the second electrode is an anode that is a hole-injecting electrode.

[0153] For example, in an organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer and an electron transport region disposed between the light-emitting layer and the second electrode, where the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0154] In this specification, the term "organic layer" refers to a single and / or multiple layers disposed between a first electrode and a second electrode in an organic light-emitting device. The term "organic layer" includes not only organic compounds but also organometallic complexes containing metals.

[0155] Figure 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment of the present invention. The structure and manufacturing method of the organic light emitting device according to an embodiment of the present invention will now be described with reference to Figure 1. The organic light emitting device 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked in this order.

[0156] A substrate is additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate that is generally used in organic light-emitting devices is used, but a glass substrate or a transparent plastic substrate that has excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is used.

[0157] The first electrode 11 is formed by depositing a first electrode material on the substrate using, for example, evaporation or sputtering. The first electrode 11 is an anode. The first electrode material includes a material with a high work function to facilitate hole injection. The first electrode 11 may be a reflective electrode, a semi-transparent electrode, or a transparent electrode. Examples of the first electrode material include indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), and zinc oxide (ZnO). Alternatively, the first electrode material may include 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).

[0158] The first electrode 11 has a single layer structure or a multi-layer structure including two or more layers, for example, a three-layer structure of ITO / Ag / ITO.

[0159] An organic layer 15 is disposed on top of the first electrode 11.

[0160] Organic layers 15 include a hole transport region, an emissive layer, and an electron transport region.

[0161] The hole transport region is disposed between the first electrode 11 and the light emitting layer.

[0162] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0163] The hole transport region may include only a hole injection layer or only a hole transport layer, or may have a structure of a hole injection layer / hole transport layer or a hole injection layer / hole transport layer / electron blocking layer stacked in this order from the first electrode 11.

[0164] When the hole transport region includes a hole injection layer, the hole injection layer is formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) method.

[0165] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the purpose and structure of the hole injection layer, and the thermal properties. For example, the deposition temperature is about 100 to about 500°C, the vacuum degree is about 10 -8 ~about 10 -3 Torr, and the deposition rate is selected from the range of about 0.01 to about 100 Å / sec.

[0166] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the structure of the intended hole injection layer, and the thermal properties. The coating is performed at a coating speed of about 2,000 rpm to about 5,000 rpm, and the heat treatment temperature for removing the solvent after coating is selected from the temperature range of about 80°C to 200°C.

[0167] The conditions for forming the hole transport layer and the electron blocking layer refer to the conditions for forming the hole injection layer.

[0168] The hole transport region may include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, Spiro-TPD, Spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(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 the following chemical formula 201, a compound represented by the following chemical formula 202, or any combination thereof.

[0169] [ka]

[0170] [ka]

[0171] [ka]

[0172] In the above formula 201, Ar 101 and Ar 102 are each independently deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, a C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkyl groups, C1-C 10Heterocycloalkenyl groups, C6-C 60 Aryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 A phenylene group, a pentalenylene group, an indenylene group, a naphthylene group, an azulenylene group, a heptalenylene group, an acenaphthylene group, a fluorenylene group, a phenalenylene group, a phenanthrenylene group, an anthracenylene group, a fluoranthenylene group, a triphenylenylene group, a pyrenylene group, a chrysenylenylene group, a naphthacenylene group, a picenylene group, a perylenylene group, or a pentacenylene group, which may be substituted or unsubstituted with a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic hetero-fused polycyclic group, or any combination thereof.

[0173] In the above chemical formula 201, xa and xb are each independently an integer of 0 to 5, or 0, 1, or 2. For example, xa is 1 and xb is 0.

[0174] In the above chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 are each independently Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), or C1-C 10 Alkoxy groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.); C1-C substituted or unsubstituted with deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, or any combination thereof 10Alkyl group or C1-C 10 an alkoxy group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups, C1-C 10 phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl groups, substituted or unsubstituted with alkoxy groups, or any combination thereof;

[0175] In the above chemical formula 201, R 109 represents deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, C1-C 20 The alkyl group may be a phenyl, naphthyl, anthracenyl, or pyridinyl group, substituted or unsubstituted with an alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group, or any combination thereof.

[0176] According to one embodiment, the compound represented by Formula 201 is represented by Formula 201A below.

[0177] [ka]

[0178] In the above formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed explanation, please refer to the above section.

[0179] For example, the hole transport region may include one of the following compounds: HT1 to HT20, or any combination thereof.

[0180] [ka] [ka]

[0181] The thickness of the hole transport region is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer is about 100 Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å, and the thickness of the hole transport layer is about 50 Å to about 2,000 Å, for example, about 100 Å to about 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above-mentioned ranges, satisfactory hole transport properties can be obtained without a substantial increase in driving voltage.

[0182] In addition to the materials described above, the hole transport region may further comprise a charge generating material to enhance conductivity. The charge generating material may be dispersed uniformly or non-uniformly within the hole transport region.

[0183] The charge-generating material may be, for example, a p-dopant. The p-dopant may be a quinone derivative, a metal oxide, a cyano group-containing compound, or any combination thereof. For example, the p-dopant may be a quinone derivative such as tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinone dimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide such as tungsten oxide or molybdenum oxide; a cyano group-containing compound such as the following compound HT-D1; or any combination thereof.

[0184] [ka]

[0185] The hole transport region further includes a buffer layer.

[0186] The buffer layer compensates for the optical resonance distance depending on the wavelength of light emitted from the light emitting layer, thereby increasing efficiency.

[0187] When the hole-transporting region includes an electron-blocking layer, the material for the electron-blocking layer can be a material used in the hole-transporting region, a host material described below, or any combination thereof. For example, when the hole-transporting region includes an electron-blocking layer, the material can be mCP, H-H1, or the like described below.

[0188] The light-emitting layer is formed on the hole transport region using a method such as vacuum deposition, spin coating, casting, or the LB method. When forming the light-emitting layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, and are generally selected from approximately the same range of conditions as those for forming the hole injection layer.

[0189] The light-emitting layer comprises a host and a dopant, and the dopant comprises the organometallic compound represented by Chemical Formula 1 above as described herein.

[0190] The host includes TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, Compound H-H1, Compound H-E43, or any combination thereof.

[0191] [ka]

[0192] When the organic light emitting device is a full-color organic light emitting device, the light emitting layer may be patterned into a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer, or may have a structure in which red light emitting layer, green light emitting layer, and / or blue light emitting layer are stacked to emit white light.

[0193] When the light-emitting layer contains a host and a dopant, the content of the dopant is generally selected from the range of about 0.01 to about 15 parts by weight based on about 100 parts by weight of the host.

[0194] The thickness of the light-emitting layer is about 100 Å to about 1,000 Å, for example, about 200 Å to about 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light-emitting characteristics can be exhibited without a substantial increase in driving voltage.

[0195] An electron transport region is then deposited on top of the light-emitting layer.

[0196] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0197] For example, the electron transport region may have a structure of hole blocking layer / electron transport layer / electron injection layer, or electron transport layer / electron injection layer. The electron transport layer may have a single layer structure or a multilayer structure containing two or more different materials.

[0198] The conditions for forming the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region refer to the conditions for forming the hole injection layer.

[0199] When the electron transport region includes a hole-blocking layer, the hole-blocking layer includes, for example, BCP (described below), Bphen (described below), BAlq (described below), or any combination thereof.

[0200] [ka]

[0201] The thickness of the hole-blocking layer is about 20 Å to about 1,000 Å, for example, about 30 Å to about 600 Å. When the thickness of the hole-blocking layer satisfies the above range, excellent hole-blocking properties can be obtained without a substantial increase in driving voltage.

[0202] The electron transport layer contains the above-mentioned BCP, Bphen, or TPBi, and the below-mentioned Alq3, BAlq, TAZ, or NTAZ, or any combination thereof.

[0203] [ka]

[0204] Alternatively, the electron transport layer includes one or any combination of the following compounds ET1 to ET25.

[0205] [ka] [ka]

[0206] The thickness of the electron transport layer is about 100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. When the thickness of the electron transport layer satisfies the above range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.

[0207] The electron transport layer further contains a metal-containing material in addition to the materials described above.

[0208] The metal-containing material includes a Li complex, such as the compound ET-D1 or the chemical formula ET-D2.

[0209] [ka]

[0210] The electron transport region also includes an electron injection layer that facilitates electron injection from the second electrode 19 .

[0211] The electron injection layer comprises LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0212] The thickness of the electron injection layer is about 1 Å to about 100 Å, for example, about 3 Å to about 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0213] A second electrode 19 is disposed on the organic layer 15. The second electrode 19 is a cathode. The second electrode 19 may be formed of a metal, alloy, or electrically conductive compound having a relatively low work function, or any combination thereof. Specific examples of materials that may be used to form the second electrode 19 include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag). Alternatively, various modifications are possible, such as forming a transmissive second electrode 19 using ITO or IZO to obtain a top-emitting device.

[0214] Although the organic light-emitting device has been described above with reference to FIG. 1, it is not limited thereto.

[0215] According to yet another aspect, the organic light-emitting device is included in an electronic device. Thus, an electronic device including the organic light-emitting device is provided. The electronic device includes, for example, a display, a lighting device, a sensor, and the like.

[0216] In yet another aspect, there is provided a diagnostic composition comprising one or more organometallic compounds represented by Formula 1 above.

[0217] The organometallic compound represented by Chemical Formula 1 provides high luminescence efficiency, and therefore a diagnostic composition containing the organometallic compound has high diagnostic efficiency.

[0218] Diagnostic compositions are widely used in various diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

[0219] As used herein, C1-C 60The alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, C1-C 60 The alkylene group is C1-C 60 It means a divalent group having the same structure as an alkyl group.

[0220] As used herein, C1-C 60 Alkyl groups, C1-C 20 Alkyl groups and / or C1-C 10 Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, an n-pentyl group, a tert-pentyl group, a neopentyl group, an isopentyl group, a sec-pentyl group, a 3-pentyl group, a sec-isopentyl group, an n-hexyl group, an isohexyl group, a sec-hexyl group, a tert-hexyl group, an n-heptyl group, an isoheptyl group, a sec-heptyl group, a tert-heptyl group, an n-octyl group, an isooctyl group, a sec-octyl group, a tert-octyl group, an n-nonyl group, an isononyl group, a sec-nonyl group, a tert-nonyl group, an n-decyl group, an isodecyl group, a sec-decyl group, a tert-decyl group, or any combination thereof. and the like, which may be substituted or unsubstituted, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, n-hexyl, isohexyl, sec-hexyl, tert-hexyl, n-heptyl, isoheptyl, sec-heptyl, tert-heptyl, n-octyl, isooctyl, sec-octyl, tert-octyl, n-nonyl, isononyl, sec-nonyl, tert-nonyl, n-decyl, isodecyl, sec-decyl, or tert-decyl. For example, the above formula 9-33 is a branched C6 alkyl group, which can be seen as a tert-butyl group substituted with two methyl groups.

[0221] As used herein, C1-C 60The alkoxy group is -OA. 101 (where A 101 is C1-C 60 Specific examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a pentoxy group.

[0222] As used herein, C2-C 60 Alkenyl groups are C2-C 60 It has a structure containing one or more carbon-carbon double bonds in the middle or at the end of the alkyl group, and specific examples thereof include ethenyl, propenyl, and butenyl groups. 60 The alkenylene group is C2-C 60 It means a divalent group having the same structure as an alkenyl group.

[0223] As used herein, C2-C 60 Alkynyl groups are C2-C 60 It has a structure containing one or more carbon-carbon triple bonds in the middle or at the end of the alkyl group, and specific examples thereof include an ethynyl group and a propynyl group. 60 The alkynylene group is C2-C 60 It means a divalent group having the same structure as an alkynyl group.

[0224] As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 means a monovalent saturated hydrocarbon cyclic group, C3-C 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0225] As used herein, C3-C 10Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (or bicyclo[2.2.1]heptyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.2]octyl, and the like.

[0226] As used herein, C1-C 10 The heterocycloalkyl group is a C1-C10 alkyl group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 10 means a monovalent cyclic group, C1-C 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0227] As used herein, C1-C 10 Examples of heterocycloalkyl groups include silolanyl, silnanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl groups.

[0228] As used herein, C3-C 10 The cycloalkenyl group is C3-C 10 It means a monovalent cyclic group that has at least one carbon-carbon double bond in the ring but does not have aromaticity, and specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 10 The cycloalkenylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkenyl group.

[0229] As used herein, C1-C 10 The heterocycloalkenyl group is a C1-C10 alkyl group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 10It is a monovalent cyclic group and has at least one double bond in the ring. 10 Specific examples of heterocycloalkenyl groups include a 2,3-dihydrofuranyl group, a 2,3-dihydrothiophenyl group, and the like. 10 The heterocycloalkenylene group is a C1-C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0230] As used herein, C6-C 60 The aryl group is C6-C 60 means a monovalent group having a carbocyclic aromatic system, C6-C 60 The arylene group is C6-C 60 means a divalent group having a carbocyclic aromatic system. C6-C 60 Specific examples of the aryl group include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, and a chrysenyl group. 60 Aryl groups and C6-C 60 When the arylene group contains more than one ring, the two or more rings are fused together.

[0231] As used herein, C7-C 60 The alkylaryl group has at least one C1-C 60 C6-C substituted with alkyl groups 60 It means an aryl group.

[0232] As used herein, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and is C-C 60 means a monovalent group having a cyclic aromatic system, C1-C 60 The heteroarylene group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and is C-C 60 means a divalent group having a carbocyclic aromatic system. C1-C 60Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 60 Heteroaryl groups and C1-C 60 When the heteroarylene group contains more than one ring, the two or more rings are fused together.

[0233] As used herein, C2-C 60 The alkylheteroaryl group has at least one C-C 60 C1-C substituted with alkyl groups 60 It means a heteroaryl group.

[0234] As used herein, C6-C 60 The aryloxy group is -OA. 102 (where A 102 is C6-C 60 aryl group), and C6-C 60 The arylthio group is -SA 103 (where A 103 is C6-C 60 aryl group), and C1-C 60 The alkylthio group is -SA 104 (where A 104 is C1-C 60 (an alkyl group).

[0235] As used herein, a monovalent non-aromatic fused polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are fused together, contain only carbon as ring-forming atoms, and the entire molecule has non-aromaticity. Specific examples of monovalent non-aromatic fused polycyclic groups include a fluorenyl group. As used herein, a divalent non-aromatic fused polycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused polycyclic group.

[0236] As used herein, a monovalent non-aromatic fused heteropolycyclic group refers to a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are fused together and which contain, in addition to carbon, heteroatoms selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms, and the entire molecule is non-aromatic. Examples of monovalent non-aromatic fused heteropolycyclic groups include a carbazolyl group. As used herein, a divalent non-aromatic fused heteropolycyclic group refers to a divalent group having the same structure as a monovalent non-aromatic fused heteropolycyclic group.

[0237] As used herein, C5-C 30 A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring atoms. 30 A carbocyclic group is a monocyclic group or a polycyclic group. 10a (or C5-C substituted or unsubstituted with at least one Z0) 30 A "carbocyclic group" is, for example, (at least one R 10a (or substituted or unsubstituted with at least one Z), adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[2.1.1]hexane group, bicyclo[2.2.1]heptane group (norbornane group), bicyclo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, cyclopentadiene group, fluorene group, and the like.

[0238] As used herein, C1-C 30 The heterocyclic group refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbon atoms as ring-forming atoms, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B. 30 The heterocyclic group is a monocyclic group or a polycyclic group. 10a (or C1-C substituted or unsubstituted with at least one Z0) 30 The "heterocyclic group" is, for example, (at least one R10a (or substituted or unsubstituted with at least one Z0) thiophene group, furan group, pyrrole group, silole group, borole group, phosphole group, selenophene group, germole group, benzothiophene group, benzofuran group, indole group, benzosilole group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermole group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborole group, dibenzyl group, dibenzophosphole group, dibenzoselenophene group, dibenzogermole group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzoborole group, azabenzophosphole group, azabenzoselenophene group, azabenzogermole group, azadibenzothiophene group, azadibenzofuran group azacarbazole group, azafluorene group, azadibenzosilole group, azadibenzoborole group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group Examples of such groups include a phosphorus group, a phenanthroline group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0239] As yet another example, the term "C5-C 30 Carbocyclic group" and "C1-C 30Examples of the "heterocyclic group" include i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused to each other, iv) a fused ring in which two or more second rings are fused to each other, or v) a fused ring in which one or more first rings and one or more second rings are fused to each other; the first ring is a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, a pyrrole group, a silole group, a borole group, a phosphole group, a germole group, a selenophene group, an oxazole group, an isoxazole group, an oxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilol group, or a triazasilol group; The second ring is an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group.

[0240] As used herein, "fluorinated C1-C 60 Alkyl group (or fluorinated C1-C 20 alkyl groups), fluorinated C3-C 10 Cycloalkyl group, fluorinated C1-C 10 "Heterocycloalkyl group" and "fluorinated phenyl group" are C1-C substituted with at least one fluoro group (-F), respectively. 60 Alkyl group (or C1-C 20 alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 It refers to heterocycloalkyl groups, and phenyl groups. For example, a "fluorinated C alkyl group (i.e., a fluorinated methyl group)" includes -CF, -CFH, and -CFH. 60 Alkyl group (or fluorinated C1-C 20 alkyl groups), fluorinated C3-C 10 Cycloalkyl group, fluorinated C1-C 10A "heterocycloalkyl group" or a "fluorinated phenyl group" refers to i) a fully fluorinated C-C heterocycloalkyl group in which all hydrogen atoms in the group have been replaced with fluoro groups. 60 Alkyl group (or fully fluorinated C1-C 20 alkyl groups, etc.), fully fluorinated C3-C 10 Cycloalkyl groups, fully fluorinated C1-C 10 ii) a partially fluorinated C1-C2 heterocycloalkyl group, or a fully fluorinated phenyl group, in which not all hydrogen atoms in the group are replaced with fluoro groups; 60 Alkyl group (or partially fluorinated C1-C 20 alkyl groups, etc.), partially fluorinated C3-C 10 Cycloalkyl groups, partially fluorinated C1-C 10 It is a heterocycloalkyl group or a partially fluorinated phenyl group.

[0241] As used herein, "deuterated C1-C 60 Alkyl groups (or deuterated C1-C 20 alkyl groups), deuterated C3-C 10 Cycloalkyl groups, deuterated C1-C 10 "Heterocycloalkyl group" and "deuterated phenyl group" refer to C1-C10 substituted with at least one deuterium. 60 Alkyl group (or C1-C 20 alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 For example, a "deuterated C alkyl group (i.e., a deuterated methyl group)" includes -CD, -CDH, and -CDH, and a "deuterated C-C 10 For examples of "cycloalkyl groups", see, for example, the above-mentioned Chemical Formula 10-501. 60 Alkyl groups (or deuterated C1-C 20 alkyl groups), deuterated C3-C 10 Cycloalkyl groups, deuterated C1-C 10A "heterocycloalkyl group" or a "deuterated phenyl group" refers to a fully deuterated C-C group in which all hydrogen atoms in the group have been replaced with deuterium atoms. 60 Alkyl group (or fully deuterated C1-C 20 alkyl groups, etc.), fully deuterated C3-C 10 Cycloalkyl groups, fully deuterated C1-C 10 a heterocycloalkyl group or a fully deuterated phenyl group, or ii) a partially deuterated C-C group in which not all hydrogen atoms in the group are replaced with deuterium. 60 Alkyl group (or partially deuterated C1-C 20 alkyl groups, etc.), partially deuterated C3-C 10 Cycloalkyl groups, partially deuterated C1-C 10 It is a heterocycloalkyl group or a partially deuterated phenyl group.

[0242] As used herein, "(C1-C 20 (Alkyl) "X" group means at least one C-C 20 It refers to an "X" group substituted with an alkyl group. For example, as used herein, "(C1-C 20 Alkyl)C3-C 10 "Cycloalkyl group" means a group having at least one C1-C 20 C3-C substituted with alkyl groups 10 It represents a cycloalkyl group, and "(C1-C 20 "(alkyl)phenyl group" means a group having at least one C1-C 20 This refers to a phenyl group substituted with an alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group.

[0243] In this specification, "azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosilole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" respectively mean or "indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene-5-oxide group, 9H-fluoren-9-one group, dibenzothiophene-5,5-dioxide group," but means a heterocycle in which at least one of the carbon atoms forming the ring is replaced with nitrogen.

[0244] The above-mentioned substituted C5-C 30 Carbocyclic groups, substituted C2-C 30 Heterocyclic groups, substituted C1-C 60 Alkyl groups, substituted C2-C 60 Alkenyl groups, substituted C2-C 60 Alkynyl groups, substituted C1-C 60 Alkoxy groups, substituted C1-C 60 Alkylthio groups, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C7-C 60Alkylaryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 Heteroaryl groups, substituted C2-C 60 The alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic heterocyclic group each independently represent: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups C1-C 60 Alkoxy group or C1-C 60 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C7-C 60 Alkylaryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q 17), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy group or C1-C 60 Alkylthio groups; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl groups, C2-C 60 Alkenyl groups, C2-C 60 Alkynyl groups, C1-C 60 Alkoxy groups, C1-C 60 Alkylthio groups, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C7-C 60 Alkylaryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, C2-C 60 Alkylheteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29 ), or any combination thereof, substituted or unsubstituted, C3-C10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl groups, C1-C 10 Heterocycloalkenyl groups, C6-C 60 Aryl groups, C7-C 60 Alkylaryl groups, C6-C 60 Aryloxy group, C6-C 60 Arylthio groups, C1-C 60 Heteroaryl groups, C2-C 60 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q38)(Q39); or Any combination thereof;

[0245] In this specification, Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39 are each independently hydrogen; deuterium; -F; -Cl; -Br; -I; a hydroxyl group; a cyano group; a nitro group; an amidino group; a hydrazine group; a hydrazone group; a carboxylic acid group or a salt thereof; a sulfonic acid group or a salt thereof; a phosphate group or a salt thereof; deuterium, C1-C 60 Alkyl groups, C6-C 60 aryl groups, or any combination thereof, substituted or unsubstituted C1-C 60 Alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C1-C 60 Alkylthio group; C3-C 10 Cycloalkyl groups; C1-C10 Heterocycloalkyl group; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl groups, C6-C 60 C6-C substituted or unsubstituted aryl groups or any combination thereof 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 a heteroaryl group; a monovalent non-aromatic fused polycyclic group; or a monovalent non-aromatic fused polycyclic heterocyclic group.

[0246] For example, in this specification, Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q 31 ~Q 39 are each independently -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Deuterium, C1-C 10 an alkyl group, a phenyl group, or any combination thereof, substituted or unsubstituted, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, tert-pentyl, neopentyl, isopentyl, sec-pentyl, 3-pentyl, sec-isopentyl, phenyl, biphenyl, or naphthyl;

[0247] The compound and organic light-emitting device according to an embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples, but the present invention is not limited to the synthesis examples and examples. In the synthesis examples below, when it is stated that "'B' was used instead of 'A'," the amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0248] [Example]

[0249] ≪Synthesis example 1 (compound 65)≫

[0250] [ka]

[0251] <Synthesis of Compound 65A>

[0252] 4-Isobutyl-2-phenyl-5-(trimethylsilyl)pyridine (7.9 g, 27.8 mmol) and iridium chloride (4.4 g, 12.6 mmol) were mixed with 120 mL of ethoxyethanol and 40 mL of distilled water, stirred under reflux for 24 hours, and then cooled to room temperature. The resulting solid was separated by filtration and washed thoroughly with water, methanol, and hexane in that order. The resulting solid was dried in a vacuum oven to give 7.6 g of compound 65A (76% yield).

[0253] <Synthesis of Compound 65B>

[0254] Compound 65A (3.3 g, 2.1 mmol) was mixed with 90 mL of methylene chloride, and then AgOTf (1.1 g, 4.1 mmol) was mixed with 30 mL of methanol and added. The mixture was then shielded from light with aluminum foil and stirred at room temperature for 18 hours. The resulting solid was removed by filtration through Celite, and the filtrate was decompressed to obtain a solid (compound 65B), which was used in the next reaction without further purification.

[0255] <Synthesis of Compound 65>

[0256] Compound 65B (4.0 g, 4.1 mmol) and 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine (1.7 g, 4.5 mmol) were mixed with 40 mL of ethanol and stirred under reflux for 18 hours, after which the temperature was lowered. The resulting mixture was then depressurized, and the resulting solid was subjected to column chromatography (eluent: methylene chloride (MC) and hexane) to obtain 1.8 g of compound 65 (39% yield). The substance was confirmed by mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C 63 H 70 IrN3OSi2:m / z 1133.4687 found:1133.4681

[0257] ≪Synthesis Example 2 (Compound 206)≫

[0258] [ka]

[0259] <Synthesis of Compound 206A>

[0260] Compound 206A (7.2 g, 72% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0261] <Synthesis of Compound 206B>

[0262] Compound 206B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 206A was used instead of compound 65A. The obtained compound 206B was used in the next reaction without further purification.

[0263] <Synthesis of Compound 206>

[0264] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 206B was used instead of compound 65B and 4-neopentyl-2-(8-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.4 g (33% yield) of compound 206. The material was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 66 H 76 IrN3OSi2:m / z 1175.5156 found:1175.5162

[0265] ≪Synthesis Example 3 (Compound 363)≫

[0266] [ka]

[0267] <Synthesis of Compound 363A>

[0268] Compound 363A (8.1 g, 81% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0269] <Synthesis of Compound 363B>

[0270] Compound 363B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 363A was used instead of compound 65A. The obtained compound 363B was used in the next reaction without further purification.

[0271] <Synthesis of Compound 363>

[0272] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 363B was used instead of compound 65B, and 2-(7-(4-fluorophenyl)dibenzo[b,d]furan-4-yl)-4-isopropylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.2 g (29% yield) of compound 363. The substance was identified through mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C 54 H 51 FIrN3OSi2:m / z 1025.3184 found:1025.3189

[0273] ≪Synthesis Example 4 (Compound 556)≫

[0274] [ka]

[0275] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 206B was used instead of compound 65B and 5-(methyl-d3)-4-neopentyl-2-(8-phenyldibenzo[b,d]furan-2-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.7 g (36% yield) of compound 556. The substance was identified through mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C 67 H 75 D3IrN3OSi2:m / z 1192.5501 found:1192.5496

[0276] ≪Synthesis Example 5 (Compound 749)≫

[0277] [ka]

[0278] The same synthesis method as for compound 65 in Synthesis Example 1 was used, except that 4-(cyclohexylmethyl)-2-(7-phenyldibenzo[b,d]thiophen-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.1 g (27% yield) of compound 749. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 66 H 74 IrN3SSi2:m / z 1189.4771 found:1189.4763

[0279] ≪Synthesis Example 6 (Compound 2350)≫

[0280] [ka]

[0281] <Synthesis of Compound 2350A>

[0282] Compound 2350A (8.8 g, 88% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 4-(methyl-d3)-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0283] <Synthesis of Compound 2350B>

[0284] Compound 2350B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2350A was used instead of compound 65A. The obtained compound 2350B was used in the next reaction without further purification.

[0285] <Synthesis of Compound 2350>

[0286] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2350B was used instead of compound 65B and 2-(7-phenyldibenzo[b,d]furan-4-yl)-4-(phenylmethyl-d2)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)-4-(phenylmethyl-d2)pyridine, to obtain 2.1 g (45% yield) of compound 2350. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 60 H 48D8IrN3OSi2:m / z 1091.4093 found:1091.4090

[0287] ≪Synthesis Example 7 (Compound 2508)≫

[0288] [ka]

[0289] <Synthesis of Compound 2508A>

[0290] Compound 2508A (6.7 g, 67% yield) was obtained using the same method as that for synthesizing compound 65A in Synthesis Example 1 above, except that 2-(2-fluoro-4-(methyl-d3)phenyl)-4-(phenylmethyl-d2)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0291] <Synthesis of Compound 2508B>

[0292] Compound 2508B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2508A was used instead of compound 65A. The obtained compound 2508B was used in the next reaction without further purification.

[0293] <Synthesis of Compound 2508>

[0294] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2508B was used instead of compound 65B and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-(methyl-d3)phenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.3 g (26% yield) of compound 2508. The substance was identified through mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C 73 H 57 D 15 F2IrN3OSi2:m / z 1308.5753 found:1308.5760

[0295] ≪Synthesis Example 8 (Compound 2566)≫

[0296] [ka]

[0297] <Synthesis of Compound 2566A>

[0298] Compound 2566A (8.3 g, 83% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 2-(4-(methyl-d3)phenyl)-4-(propan-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0299] <Synthesis of compound 2566B>

[0300] Compound 2566B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2566A was used instead of compound 65A. The obtained compound 2566B was used in the next reaction without further purification.

[0301] <Synthesis of Compound 2566>

[0302] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2566B was used instead of compound 65B, and 4-(2,2-dimethylpropyl-1,1-d2)-2-(7-(4-fluorophenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.5 g (34% yield) of compound 2566. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 64 H 61 D 10 FIrN3OSi2:m / z 1175.5377 found:1175.5383

[0303] ≪Synthesis Example 9 (Compound 2579)≫

[0304] [ka]

[0305] <Synthesis of Compound 2579A>

[0306] Compound 2579A (8.4 g, 84% yield) was obtained using the same method as that for synthesizing compound 65A in Synthesis Example 1 above, except that 2-([1,1'-biphenyl]-3-yl)-4-(propan-2-yl-2-d)-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0307] <Synthesis of compound 2579B>

[0308] Compound 2579B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2579A was used instead of compound 65A. The obtained compound 2579B was used in the next reaction without further purification.

[0309] <Synthesis of Compound 2579>

[0310] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2579B was used instead of compound 65B and 4-(cyclopentylmethyl-d2)-2-(7-(2,6-dimethylphenyl)dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.1 g (25% yield) of compound 2579. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 77 H 76 D4IrN3OSi2:m / z 1315.5720 found:1315.5711

[0311] ≪Synthesis Example 10 (Compound 2758)≫

[0312] [ka]

[0313] <Synthesis of Compound 2758A>

[0314] Compound 2758A (7.2 g, 72% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 4-(methyl-d3)-2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0315] <Synthesis of compound 2758B>

[0316] Compound 2758B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2758A was used instead of compound 65A. The obtained compound 2758B was used in the next reaction without further purification.

[0317] <Synthesis of Compound 2758>

[0318] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2758B was used instead of compound 65B and 5-(methyl-d3)-4-phenyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 1.6 g (37% yield) of compound 2758. The material was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 60 H 47D9Ge2IrN3O:m / z 1184.3041 found:1184.3033

[0319] ≪Synthesis Example 11 (Compound 485)≫

[0320] [ka]

[0321] 0.9 g (27% yield) of compound 485 was obtained using the same method as for compound 65 in Synthesis Example 1, except that 2-(1,7-diphenyldibenzo[b,d]furan-4-yl)-4-isobutylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 69 H 74 IrN3OSi2:m / z 1209.5000 found:1209.4992

[0322] ≪Synthesis Example 12 (Compound 487)≫

[0323] [ka]

[0324] Compound 487 (1.0 g, 32% yield) was obtained using the same method as for compound 65 in Synthesis Example 1, except that 2-(7-([1,1'-biphenyl]-4-yl)dibenzo[b,d]furan-4-yl)-4-isopropylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine. The substance was identified through mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C 68 H 72 IrN3OSi2:m / z 1195.4843 found:1195.4840

[0325] ≪Synthesis Example 13 (Compound 1703)≫

[0326] [ka]

[0327] <Synthesis of Compound 1703A>

[0328] Compound 1703A (6.5 g, 65% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 2-phenyl-5-(trimethylgermyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0329] <Synthesis of compound 1703B>

[0330] Compound 1703B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 1703A was used instead of compound 65A. The obtained compound 1703B was used in the next reaction without further purification.

[0331] <Synthesis of Compound 1703>

[0332] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 1703B was used instead of compound 65B and 4-isopropyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 2.1 g (45% yield) of compound 1703. The substance was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 54 H 52 Ge2IrN3O:m / z 1099.2163 found:1099.2156

[0333] ≪Synthesis Example 14 (Compound 2866)≫

[0334] [ka]

[0335] <Synthesis of Compound 2866A>

[0336] Compound 2866A (3.6 g, 72% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 4-neopentyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0337] <Synthesis of Compound 2866B>

[0338] Compound 2866B was obtained using the same method as for synthesizing compound 65B in Synthesis Example 1 above, except that compound 2866A was used instead of compound 65A. The obtained compound 2866B was used in the next reaction without further purification.

[0339] <Synthesis of Compound 2866>

[0340] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 2866B was used instead of compound 65B and 4-neopentyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 0.5 g (24% yield) of compound 2866. The substance was identified through mass and HPLC analyses. HRMS(MALDI) calculation for C 75 H 74 IrN3O2Si:m / z 1269.5180 found:1269.5188

[0341] Comparative Example 1 (Compound A1)

[0342] [ka]

[0343] The same synthesis method as for compound 65 in Synthesis Example 1 above was used, except that compound 363B was used instead of compound 65B and 2-(dibenzo[b,d]furan-4-yl)-4-methylpyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 0.5 g (42% yield) of compound A1. The substance was identified through mass spectrometry and HPLC analysis. HRMS(MALDI) calculation for C46 H 44 IrN3OSi2:m / z 903.2652 found:903.2645

[0344] ≪Comparative Example 2 (Compound A2)≫

[0345] [ka]

[0346] <Synthesis of Compound A2A>

[0347] Compound A2A (3.4 g, 86% yield) was obtained using the same method as that for compound 65A in Synthesis Example 1 above, except that 4-methyl-2-phenyl-5-(trimethylsilyl)pyridine was used instead of 4-isobutyl-2-phenyl-5-(trimethylsilyl)pyridine.

[0348] <Synthesis of Compound A2B>

[0349] Compound A2B was obtained using the same method as that for synthesizing compound 65B in Synthesis Example 1 above, except that compound A2A was used instead of compound 65A. The obtained compound A2B was used in the next reaction without further purification.

[0350] <Synthesis of Compound A2>

[0351] The same synthesis method as in Synthesis Example 1 for Compound 65 was used, except that Compound A2B was used instead of Compound 65B and 2-(dibenzo[b,d]furan-4-yl)pyridine was used instead of 4-isobutyl-2-(7-phenyldibenzo[b,d]furan-4-yl)pyridine, to obtain 20.3 g (41% yield) of Compound A. The material was identified through mass and HPLC analysis. HRMS(MALDI) calculation for C 47 H 46 IrN3OSi2:m / z 917.2809 found:917.2801

[0352] Example 1

[0353] As an anode, a glass substrate on which ITO had been patterned was cut to a size of 50 mm × 50 mm × 0.5 mm, and ultrasonically cleaned using isopropyl alcohol and pure water for 5 minutes each, then irradiated with ultraviolet light for 30 minutes and exposed to ozone for cleaning, and then placed in a vacuum deposition apparatus.

[0354] On top of the anode, the following compound HT3 and the following compound F6-TCNNQ were vacuum co-deposited in a weight ratio of 98:2 to form a 100 Å thick hole injection layer, and on top of the hole injection layer, the following compound HT3 was vacuum deposited to form a 1,350 Å thick hole transport layer, and then on top of the hole transport layer, the following compound H-H1 was vacuum deposited to form a 300 Å thick electron blocking layer.

[0355] Next, on the electron-blocking layer, Compound H-H1 below, Compound H-E43 below, and Compound 65 (dopant) above were co-deposited in a weight ratio of 57:38:5 to form a 400 Å-thick light-emitting layer.

[0356] Thereafter, the following compound ET3 and the following compound ET-D1 were co-deposited on top of the light-emitting layer in a volume ratio of 50:50 to form a 350 Å-thick electron transport layer, the following compound ET-D1 was vacuum-deposited on top of the electron transport layer to form a 10 Å-thick electron injection layer, and Al was vacuum-deposited on top of the electron injection layer to form a 1,000 Å-thick cathode, thereby producing an organic light-emitting element.

[0357] [ka]

[0358] Examples 2 to 14 and Comparative Examples A1 and A2

[0359] An organic light-emitting device was fabricated using the same method as in Example 1, except that when forming the light-emitting layer, the compounds listed in Table 2 below were used as the dopant instead of Compound 65.

[0360] <Evaluation Example 1: Characterization of organic light-emitting devices>

[0361] The maximum external quantum efficiency (Max EQE) (%) and lifetime (LT) of each of the organic light-emitting devices manufactured in Examples 1 to 14 and Comparative Examples A1 and A2 were measured. 97 The results are shown in Table 2. A current-voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment, and the lifespan (LT 97 )(@16,000 nit ) was evaluated as the time (hr) required for the brightness to decrease to 97% of the initial brightness of 100%, and was expressed as a relative value (%).

[0362] [Table 2]

[0363] [ka]

[0364] From Table 2 above, it can be seen that the organic light-emitting devices of Examples 1 to 14 have improved external quantum efficiency and improved life characteristics compared to the organic light-emitting devices of Comparative Examples A1 and A2.

[0365] Although the embodiments of the present invention have been described in detail above, the present invention is not limited to the above-described embodiments and can be modified in various ways without departing from the technical concept of the present invention. [Explanation of symbols]

[0366] 10 Organic light-emitting device 11 First Electrode 15 Organic Layer 19. Second electrode

Claims

1. An organometallic compound represented by the following chemical formula 1: [Chemical 1] M(L 1 ) n1 (L 2 ) n2 In the above Chemical Formula 1, M is Ir; L 1 is a ligand represented by the following chemical formula 2A: L 2 is a ligand represented by the following chemical formula 2B: n1 and n2 are each independently 1 or 2, and when n1 is 2, two L 1 are the same or different, and when n2 is 2, two L 2 are the same as or different from each other, The sum of n1 and n2 is 3, L 1 and L 2 are different from each other, 【Chemistry 2A】 【Chemistry 2B】 In Formula 2A and Formula 2B, Y 4 is C, X 1 is Si or Ge, X 21 is O or S, T 1 ~T 4 are each independently C, N, a ring CY 1 or the carbon bonded to M in Formula 1, but T 1 ~T 4 One of the carbon atoms is bonded to M in Formula 1, and the remaining T atoms are not bonded to M. 1 ~T 4 One of them is the ring CY 1 is a carbon bonded to T 5 ~T 8 are each independently C or N, T 1 ~T 8 In the above, the number of N is 0 or 1, Ring CY 1 is a pyridine group, Ring CY 14 is a benzene group, Ar 2 is at least one Z 0 a ring CY substituted or unsubstituted with 2 wherein the ring CY 2 is a benzene group, R 21 ~R 23 are each independently deuterium, -F, or -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 20 C substituted or unsubstituted with alkyl groups, phenyl groups, or any combination thereof 1 -C 60 Alkyl group or C 6 -C 60 is an aryl group, Z 0 , Z 1 , Z 2 , and R 11 ~R 14 are each independently hydrogen, deuterium, —F, a cyano group, a substituted or unsubstituted C 1 -C 60 alkyl group, substituted or unsubstituted C 2 -C 60 Alkenyl group, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 6 -C 60 aryl group, substituted or unsubstituted C 6 -C 60 aryloxy group, substituted or unsubstituted C 6 -C 60 arylthio group, substituted or unsubstituted C 1 -C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, d2 is an integer of 1 to 6, and when d2 is 2 or more, there are 2 or more Ar 2 are the same as or different from each other, a1 and b1 are each independently an integer of 0 to 4, and when a1 is 2 or more, two or more Z 1 are the same or different from each other, and when b1 is 2 or more, two or more R 14 are the same as or different from each other, a2 is an integer of 0 to 5, and when a2 is 2 or more, 2 or more Z 2 are the same as or different from each other, Satisfy the following <Condition 1> or <Condition 2>, <Condition 1> In the formula 2B, X 1 is Si, In Formula 2B, R 12 But it is neither hydrogen nor a methyl group. T of Formula 2A 1 ~T 8 In this case, the number of N is 0. <Condition 2> In Formula 2B, R 12 is hydrogen, or R 12 The number of carbon atoms contained in Multiple Zs 2 two or more of which are optionally linked to each other, and at least one R 10a substituted or unsubstituted C 5 -C 30 forming a carbocyclic group, The R 10a The explanation regarding R 14 is identical to the description of In Formula 2A and Formula 2B, * and *' are binding sites with M in Formula 1, respectively; The substituted C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 6 -C 60 Aryl groups, substituted C 6 -C 60 Aryloxy groups, substituted C 6 -C 60 Arylthio groups, substituted C 1 -C 60 The heteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic heterocyclic group are Deuterium, -F, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 60 Alkyl group, or C 2 -C 60 alkenyl group; Deuterium, -F, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 3 -C 10 Cycloalkyl group, C 6 -C 60 C substituted with an aryl group, or any combination thereof 1 -C 60 Alkyl group, or C 2 -C 60 alkenyl group; Deuterium, -F, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 3 -C 10 Cycloalkyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 C, substituted or unsubstituted with a heteroaryl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or any combination thereof; 3 -C 10 Cycloalkyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; or any combination thereof;

2. The organometallic compound of claim 1, wherein, in Formula 1, i) n1 is 1 and n2 is 2, or ii) n1 is 2 and n2 is 1.

3. The organometallic compound of claim 1 , wherein d2 in Formula 2A is 1 or 2.

4. In the chemical formula 2A, Z 1 and in formula 2B, R 11 ~R 13 are each independently hydrogen or deuterium; Deuterium-substituted or unsubstituted C 1 -C 20 an alkyl group; or Deuterium, -F, cyano group, C 1 -C 20 Alkyl group, deuterated C 1 -C 20 2. The organometallic compound according to claim 1, wherein the phenyl group is a phenyl group substituted or unsubstituted with an alkyl group, or any combination thereof.

5. In the chemical formula 2A, Z 0 and Z 2 and in Formula 2B, R 14 are each independently hydrogen, deuterium, -F, or a cyano group; Deuterium, -F, cyano group, C 3 -C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 cycloalkyl groups, (C 1 -C 20 alkyl) C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 C substituted or unsubstituted alkyl) biphenyl groups, or any combination thereof 1 -C 20 an alkyl group; or Deuterium, -F, cyano group, C 1 -C 20 Alkyl group, deuterated C 1 -C 20 Alkyl group, fluorinated C 1 -C 20 Alkyl groups, C3-C 10 Cycloalkyl groups, deuterated C 3 -C 10 Cycloalkyl groups, fluorinated C 3 -C 10 cycloalkyl groups, (C 1 -C 20 alkyl) C 3 -C 10 Cycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C 1 -C 20 alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C 1 -C 20 C substituted or unsubstituted with alkyl)biphenyl groups, or any combination thereof 3 -C 10 2. The organometallic compound according to claim 1, wherein the group is a cycloalkyl group, a phenyl group, or a biphenyl group.

6. 2. The organometallic compound according to claim 1, which satisfies at least one of the following conditions A to C: <Condition A> In the chemical formula 2A, Z 1 is not hydrogen and a1 is not 0 <Condition B> In the chemical formula 2A, Z 2 is not hydrogen and a2 is not 0 <Condition C> In Formula 2B, R 14 is not hydrogen and b1 is not 0.

7. The above <Condition 1> is satisfied, and R of the above Chemical Formula 2B 12 2. The organometallic compound according to claim 1, wherein the number of carbon atoms contained in the formula (I) is 2 or more.

8. 2. The organometallic compound according to claim 1, which satisfies the condition 2.

9. 2. The organometallic compound of claim 1, comprising at least one deuterium, at least one fluoro group (--F), at least one cyano group (--CN), or any combination thereof.

10. 2. The organometallic compound according to claim 1, characterized in that it satisfies at least one of the following <Condition (1)> to <Condition (6)>, or the following <Condition (7)>: <Condition (1)> In the formula 2A, a1 is not 0, and a1 Z 1 At least one of them contains deuterium <Condition (2)> In the formula 2A, a2 is not 0, and a2 Z 2 At least one of the groups contains deuterium, a fluoro group (—F), a cyano group, or any combination thereof. <Condition (3)> In the above Formula 2A, d2 Ar 2 At least one of the groups contains deuterium, a fluoro group (—F), a cyano group, or any combination thereof. <Condition (4)> R of Formula 2B 21 ~R 23 At least one of them contains deuterium <Condition (5)> In Formula 2B, R 12 contains at least one deuterium <Condition (6)> In Formula 2B, b1 is not 0, and b1 R 14 At least one of the groups contains deuterium, a fluoro group (—F), a cyano group, or any combination thereof. <Condition (7)> In the chemical formula 2A, Z 1 , Z 2 , and Ar 2 and in Formula 2B, R 11 ~R 14 , and R 21 ~R 23 Each of these consists of only carbon and hydrogen.

11. In the above Formula 2A, 【Chemical Engineering 2A-CY1】 2. The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas CY1-1 to CY1-16. 【Chemistry (CY1-1)-(CY1-28)】 In the chemical formulas CY1-1 to CY1-16, Z 11 ~Z 14 The explanation regarding Z is given in claim 1. 1 Although the explanation is the same as for Z 11 ~Z 14 Each of these is not hydrogen, * is a bonding site with M in Chemical Formula 1; *" is T in the above chemical formula 2A. 1 ~T 4 It is a binding site for one of the

12. In the above Formula 2A, 【Chemistry 2A-2】 2. The organometallic compound according to claim 1, wherein the group represented by the formula: is a group represented by one of the following chemical formulas CY2-1 to CY2-6. 【Chemistry (CY2-1)-(CY2-6)】 In the chemical formulas CY2-1 to CY2-6, T 1 ~T 8 are each independently C or N, but T in the formula CY2-1 and the formula CY2-6 3 ~T 8 In the formula CY2-2 and the formula CY2-5, the number of N is 0 or 1. 1 , T 2 , T 5 , T 6 , T 7 , and T 8 In the formula CY2-3 and the formula CY2-4, the number of N is 0 or 1. 1 , T 4 , T 5 , T 6 , T 7 , and T 8 In the above, the number of N is 0 or 1, X 21 The explanation regarding is the same as that described in claim 1, *" is a binding site to ring CY1 in Chemical Formula 2A, *' is a binding site with M in Chemical Formula 1.

13. An organometallic compound characterized by being any one of the following compounds 65, 206, 363, 485, 487, 556, 749, 1703, 2350, 2508, 2566, 2579, 2758 or 2866.

14. A first electrode; A second electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; 14. An organic light-emitting device, wherein the organic layer comprises one or more organometallic compounds according to claim 1.

15. 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 light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode; the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof; 15. The organic light-emitting device of claim 14, wherein the electron transport region comprises a hole-blocking layer, an electron-transporting layer, an electron-injecting layer, or any combination thereof.

16. The organic light-emitting device according to claim 14 , wherein the organometallic compound is contained in the light-emitting layer.

17. the light-emitting layer further comprises a host; The organic light emitting device of claim 16, wherein the content of the host is greater than the content of the organometallic compound.

18. An electronic device comprising the organic light-emitting element according to any one of claims 14 to 17.

Citation Information

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