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

Abstract

To provide an organometallic compound and an organic light-emitting device including the organometallic compound.SOLUTION: An organometallic compound herein is represented by chemical formula 1 shown below. For explanations of the chemical formula 1, the corresponding descriptions of the specifications are referred to.SELECTED DRAWING: Figure 1

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. According to one example, an organic light-emitting device includes an anode, a cathode, and an organic layer including an emitting layer interposed between the anode and the cathode. A hole transport region is provided between the anode and the emitting layer, and an electron transport region is provided 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 an excited state to a ground state. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] Japanese Patent Application Laid-Open No. 2017-39713 Summary of the Invention [Problem to be solved by the invention]

[0004] 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]

[0005] In order to achieve the above object, an organometallic compound according to one aspect of the present invention is represented by the following Chemical Formula 1. [ka] In the formula 1, M is a transition metal; In the above formula 1, X1 to X4 are each independently C or N; In the formula 1, two of the bonds between X1 and M, between X2 and M, between X3 and M, and between X4 and M are coordinate bonds, and the remaining two are covalent bonds; In the above Chemical Formula 1, Z1 to Z4 are each independently a group represented by the following Chemical Formula 2: [ka] In the above Chemical Formula 1, b1 to b4 are each independently an integer of 0 to 20, and the sum of b1 to b4 is 1 or more; In the above formula 1, rings CY1 to CY4 each independently represent a C5-C 30 Carbocyclic group or C1-C 30 is a heterocyclic group, In the formula 1, T1 is a single bond, a double bond, or -N(R 5a )-*', *-B(R 5a )-*', *-P(R 5a )-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*', *=C(R 5a )-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C-*', at least one R 10a Substituted or unsubstituted C5-C 30a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 is a heterocyclic group, In the formula 1, T2 is a single bond, a double bond, or *-N(R 6a )-*', *-B(R 6a )-*', *-P(R 6a )-*', *-C(R 6a )(R 6b )-*', *-Si(R 6a )(R 6b )-*', *-Ge(R 6a )(R 6b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 6a )=*', *=C(R 6a )-*', *-C(R 6a )=C(R 6b )-*', *-C(=S)-*', *-C≡C-*', 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 is a heterocyclic group, In the formula 1, T3 is a single bond, a double bond, or -N(R 7a )-*', *-B(R 7a )-*', *-P(R 7a )-*', *-C(R 7a )(R 7b )-*', *-Si(R 7a )(R 7b )-*', *-Ge(R 7a )(R 7b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 7a )=*', *=C(R 7a )-*', *-C(R 7a )=C(R 7b )-*', *-C(=S)-*', *-C≡C-*', at least one R 10a Substituted or unsubstituted C5-C30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 is a heterocyclic group, In the formula 1, T4 is a single bond, a double bond, or -N(R 8a )-*', *-B(R 8a )-*', *-P(R 8a )-*', *-C(R 8a )(R 8b )-*', *-Si(R 8a )(R 8b )-*', *-Ge(R 8a )(R 8b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 8a )=*', *=C(R 8a )-*', *-C(R 8a )=C(R 8b )-*', *-C(=S)-*', *-C≡C-*', 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 is a heterocyclic group, In the above Chemical Formula 1, n1 to n4 are each independently an integer of 0 to 5, and three or more of n1 to n4 are each independently an integer of 1 to 5; In the above Chemical Formula 1, when n1 is 0, T1 is absent, when n2 is 0, T2 is absent, when n3 is 0, T3 is absent, and when n4 is 0, T4 is absent; In the formula 1, when n1 is 2 or more, two or more T1 are the same or different from each other; when n2 is 2 or more, two or more T2 are the same or different from each other; when n3 is 2 or more, two or more T3 are the same or different from each other; when n4 is 2 or more, two or more T4 are the same or different from each other; In the above formulas 1 and 2, R1 to R4, R 5a , R 5b , R 6a , R6b , R 7a , R 7b , R 8a , R 8b , and Q 51 ~Q 53 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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, 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 C7-C 60 Alkylaryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C2-C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), where Q is 51 ~Q 53 Each of these is not hydrogen, Q of the above Chemical Formula 2 51 ~Q 53At least one of the groups is independently a substituted or unsubstituted C-C 60 Aryl groups, substituted or unsubstituted C1-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, In the above Chemical Formula 1, a1 to a4 each independently represent an integer of 0 to 20; In the formula 2, L is a single bond, 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 is a heterocyclic group, In the above Chemical Formula 2, c1 is an integer of 1 to 10; In the above Chemical Formula 2, c2 is an integer of 1 to 20; In the formula 1, two or more of the a1 R1 are optionally bonded 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, In the formula 1, two or more of the a2 R2 may be optionally bonded 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, In the formula 1, two or more of the a3 R3 may be optionally bonded 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, In the formula 1, two or more of the a4 R4 may be optionally bonded to each other, and at least one R 10aSubstituted or unsubstituted C5-C 30 a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 forming a heterocyclic group, R1 to R4, R 5a , R 5b , R 6a , R 6b , R 7a , R 7b , R 8a , and R 8b two or more of the groups may optionally be bonded 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 the explanation of R1, refer to the explanation of R1 above. * and *' are bonding sites with adjacent atoms, 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 C7-C 60 Alkylaryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 Heteroaryl groups, substituted C2-C 60 The substituents of the alkylheteroaryl 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 group, or C1-C 60 Alkoxy 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 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 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 group, or C1-C 60 Alkoxy 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, 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 )(Q 22 ), -Si(Q 23 )(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(Q31 )(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 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 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; C3-C 10 Cycloalkyl group; 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.

[0006] 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 a light-emitting layer, wherein the organic layer includes one or more of the organometallic compounds. The organometallic compound is contained in the light-emitting layer of the organic layer, and the organometallic compound contained in the light-emitting layer serves as a dopant.

[0007] In yet another aspect, an electronic device is provided that includes the organic light emitting device. [Effects of the Invention]

[0008] The organometallic compounds of the present invention have excellent thermal stability and electrical properties, and electronic devices employing the organometallic compounds, such as organic light-emitting devices, can emit light with a relatively small full width at half maximum (FWHM) while exhibiting improved driving voltage, improved external quantum efficiency, and improved lifetime characteristics. [Brief explanation of the drawings]

[0009] [Figure 1] 1 is a cross-sectional view schematically illustrating an organic light emitting device according to an embodiment; DETAILED DESCRIPTION OF THE INVENTION

[0010] Specific examples of embodiments for carrying out the present invention will be described in detail below.

[0011] The organometallic compound of the present invention is represented by the following Chemical Formula 1:

[0012] [ka]

[0013] In the above formula 1, M is a transition metal.

[0014] For example, M can be a first period transition metal, a second period transition metal, or a third period transition metal on the periodic table.

[0015] As another example, M is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), palladium (Pd), or gold (Au).

[0016] According to one embodiment, in Formula 1, M is Pt, Pd, or Au.

[0017] In the above formula 1, X1 to X4 are each independently C or N.

[0018] According to one embodiment, X2 and X3 are C, and X4 is N. In another embodiment, X1 to X3 are C and X4 is N.

[0019] In the above Chemical Formula 1, two of the bonds between X1 and M, between X2 and M, between X3 and M, and between X4 and M are coordinate bonds, and the remaining two are covalent bonds.

[0020] According to one embodiment, the bond between X1 and M in Formula 1 is a coordinate bond. For example, in Formula 1, the bond between X1 and M is a coordinate bond and X1 is C. As another example, in Formula 1, the bond between X1 and M is a coordinate bond and X1 is N.

[0021] According to another embodiment, in Formula 1, the bond between X1 and M and the bond between X4 and M are coordinate bonds, and the bond between X2 and M and the bond between X3 and M are covalent bonds.

[0022] According to yet another embodiment, in Formula 1, X2 and X3 are C; X4 is N, the bond between X2 and M and the bond between X3 and M are covalent bonds; The bond between X1 and M and the bond between X4 and M are coordinate bonds.

[0023] In the above Chemical Formula 1, Z1 to Z4 are each independently a group represented by the following Chemical Formula 2.

[0024] [ka]

[0025] For an explanation of the above chemical formula 2, please refer to the section described in this specification.

[0026] In the above Chemical Formula 1, b1 to b4 respectively represent the number of Z1 to Z4, and each is independently an integer of 0 to 20 (e.g., 0, 1, 2, or 3), but the sum of b1 to b4 is 1 or more (e.g., 1, 2, 3, 4, 5, or 6). That is, the organometallic compound represented by the above Chemical Formula 1 contains at least one group represented by the above Chemical Formula 2 (e.g., 1, 2, 3, 4, 5, or 6). When b1 is 2 or more, two or more Z1s are the same or different from each other; when b2 is 2 or more, two or more Z2s are the same or different from each other; when b3 is 2 or more, two or more Z3s are the same or different from each other; and when b4 is 2 or more, two or more Z4s are the same or different from each other. For example, in the above formula 1, b1 is 0, 1, 2, or 3, and b2 to b4 are 0 or 1. As another example, in the above formula 1, the sum of b1, b2, b3, and b4 is 1, 2, or 3.

[0027] According to one embodiment, in Formula 1, i) b1 is 1, 2, or 3, and b2, b3, and b4 are 0, or ii) b2 is 1 and b1, b3, and b4 are 0, or iii) b3 is 1 and b1, b2, and b4 are 0, or iv) b4 is 1 and b1, b2, and b3 are 0, or v) b1 is 1 or 2, b2 is 1, and b3 and b4 are 0, or vi) b1 is 1 or 2, b3 is 1, and b2 and b4 are 0, or vii) b1 is 1 or 2, b4 is 1, and b2 and b3 are 0, or viii) b1 is 0, b2 is 1, b3 is 1 and b4 is 0, or ix) b1 is 0, b2 is 1, b3 is 0, and b4 is 1; or x) b1 is 0, b2 is 0, b3 is 1, and b4 is 1.

[0028] In the above formula 1, rings CY1 to CY4 each independently represent a C5-C 30 Carbocyclic group or C1-C 30 It is a heterocyclic group.

[0029] For example, in the above Chemical Formula 1, rings CY1 to CY4 are each independently 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 cyclopentadiene 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 isoxadiazole group, an oxatriazole group, an isoxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, an isothiazole 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 cyclohexanonediene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, an oxazine group, a thiazine group, a dihydropyrazine group, a dihydropyridine group, or a dihydroazasirol group.

[0030] According to one embodiment, in Chemical Formula 1, ring CY1 is i) a first ring, ii) a fused ring in which two or more first rings are fused to each other, or iii) a fused ring in which one or more first rings are fused to one or more second rings, and C or N of the first ring included in ring CY1 is X1 in Chemical Formula 1. That is, the first ring (e.g., a 5-membered ring) included in ring CY1 is bonded to M in Chemical Formula 1. For descriptions of the first ring and the second ring, please refer to the respective sections described in this specification.

[0031] According to another embodiment, in Formula 1, rings CY1 to CY4 are each independently a cyclopentane group, a cyclopentene group, a cyclohexane group, a cyclohexene group, a cyclohexanonediene 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-tetrahydrophthalene group, a thiophene group, a furan group, a borole group, a phosphole group, a germole group, a selenophene group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosiloxane ... a benzoindole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluorene group, a dibenzosilole group, a dibenzogermole group, a dibenzothiophene group, a dibenzoselenophene group, a dibenzofuran group, a dibenzothiophene 5-oxide group, a 9H-fluoren-9-one group, a dibenzothiophene 5,5-dioxide group, an azaindole group, an azabenzoborole group, an azabenzophosphole group, an azaindene group, an azabenzosilole group, an 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, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, or norbornene group.

[0032] According to still another embodiment, in Formula 1, ring CY1 is 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 pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group.

[0033] According to still another embodiment, in Formula 1, rings CY2 and CY3 are each independently a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a 5,6,7,8-tetrahydroisoquinoline group, or a 5,6,7,8-tetrahydroquinoline group. According to still another embodiment, in Formula 1, ring CY4 is a benzene group, a naphthalene group, a carbazole group, a fluorene group, a dibenzosilole group, a dibenzothiophene group, a dibenzofuran group, an azacarbazole group, an azafluorene group, an azadibenzosilole group, an azadibenzothiophene group, an azadibenzofuran group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a 5,6,7,8-tetrahydroisoquinoline group, a 5,6,7,8-tetrahydroquinoline group, a benzimidazole group, a benzoxazole group, or a benzothiazole group.

[0034] In the above formula 1, T1 is a single bond, a double bond, or *-N(R 5a )-*', *-B(R 5a)-*', *-P(R 5a )-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*', *=C(R 5a )-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C-*', 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 T2 is a heterocyclic group, and T2 is a single bond, a double bond, or *-N(R 6a )-*', *-B(R 6a )-*', *-P(R 6a )-*', *-C(R 6a )(R 6b )-*', *-Si(R 6a )(R 6b )-*', *-Ge(R 6a )(R 6b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 6a )=*', *=C(R 6a )-*', *-C(R 6a )=C(R 6b )-*', *-C(=S)-*', *-C≡C-*', 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 T3 is a heterocyclic group, and T3 is a single bond, a double bond, *-N(R 7a )-*', *-B(R 7a )-*', *-P(R 7a )-*', *-C(R7a )(R 7b )-*', *-Si(R 7a )(R 7b )-*', *-Ge(R 7a )(R 7b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 7a )=*', *=C(R 7a )-*', *-C(R 7a )=C(R 7b )-*', *-C(=S)-*', *-C≡C-*', 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 T4 is a heterocyclic group, and T4 is a single bond, a double bond, *-N(R 8a )-*', *-B(R 8a )-*', *-P(R 8a )-*', *-C(R 8a )(R 8b )-*', *-Si(R 8a )(R 8b )-*', *-Ge(R 8a )(R 8b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 8a )=*', *=C(R 8a )-*', *-C(R 8a )=C(R 8b )-*', *-C(=S)-*', *-C≡C-*', 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 R is a heterocyclic group. 5a , R 5b , R 6a , R 6b , R 7a , R 7b , R 8a and R 8bFor an explanation of each of these, please refer to the sections described in this specification. According to one embodiment, in Formula 1, T1 is *-N(R 5a )-*', *-B(R 5a )-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-S-*', or *-O-*'. According to another embodiment, in Formula 1, T2 is a single bond and *-N(R 6a )-*', *-B(R 6a )-*', *-C(R 6a )(R 6b )-*', *-Si(R 6a )(R 6b )-*', *-S-*', or *-O-*'. According to another embodiment, in Formula 1, T3 is a single bond. According to another embodiment, in Formula 1, T4 is *-N(R 8a )-*', *-B(R 8a )-*', *-C(R 8a )(R 8b )-*', *-Si(R 8a )(R 8b )-*', *-S-*', *-O-*), 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 It is a heterocyclic group.

[0035] In the above chemical formula 1, n1 to n4 are each independently an integer of 0 to 5, but three or more of n1 to n4 are each independently an integer of 1 to 5. That is, the organometallic compound represented by the above chemical formula 1 has a tetradentate ligand.

[0036] For example, in the above chemical formula 1, i) n1 is 0, and n2, n3, and n4 are each independently an integer of 1 to 5; or ii) n2 is 0, and n1, n3, and n4 are each independently an integer of 1 to 5; or iii) n3 is 0, and n1, n2, and n4 are each independently an integer of 1 to 5; or iv) n4 is 0, and n1, n2, and n3 are each independently an integer from 1 to 5; or v) n1, n2, n3, and n4 each independently represent an integer of 1 to 5.

[0037] In the above chemical formula 1, when n1 is 0, T1 is not present, when n2 is 0, T2 is not present, when n3 is 0, T3 is not present, and when n4 is 0, T4 is not present.

[0038] In the above chemical formula 1, when n1 is 2 or more, two or more T1s are the same or different from each other; when n2 is 2 or more, two or more T2s are the same or different from each other; when n3 is 2 or more, two or more T3s are the same or different from each other; and when n4 is 2 or more, two or more T4s are the same or different from each other.

[0039] For example, in the above chemical formula 1, 1) n4 is 0 and n1, n2, and n3 are 1, or 2) n4 is 1, 2, 3, or 4, and n1, n2, and n3 are 1; or 3) n3 is 0, n1 and n2 are 1, and n4 is 1, 2, 3, or 4; 4) n2 is 0, n1 and n3 are 1, and n4 is 1, 2, 3, or 4; or 5) n1 is 0, n2 and n3 are 1, and n4 is 1, 2, 3, or 4.

[0040] As yet another example, in the above formula 1, n1 and n3 are not 0.

[0041] According to one embodiment, in Formula 1, n1 is not 0 (e.g., n1 is 1), and T1 is *-N(R 5a )-*', *-B(R 5a )-*', *-P(R 5a )-*', *-C(R 5a )(R 5b )-*', *-Si(R 5a )(R 5b )-*', *-Ge(R 5a )(R 5b )-*', *-S-*', or *-O-*'.

[0042] According to another embodiment, in Formula 1 above, n2 is not 0 (e.g., n2 is 1), and T2 is a single bond.

[0043] According to yet another embodiment, in Formula 1, n2 is not 0 (e.g., n2 is 1), and T2 is *-N(R 6a )-*', *-B(R 6a )-*', *-P(R 6a )-*', *-C(R 6a )(R 6b )-*', *-Si(R 6a )(R 6b )-*', *-Ge(R 6a )(R 6b )-*', *-S-*', or *-O-*'.

[0044] According to yet another embodiment, in Formula 1 above, n3 is not 0 (e.g., n3 is 1), and T3 is a single bond.

[0045] According to yet another embodiment, n4 in Formula 1 is 0.

[0046] According to yet another embodiment, in Formula 1, n4 is not 0 and T4 is *-N(R 8a )-*', *-B(R 8a )-*', *-P(R 8a )-*', *-C(R 8a )(R 8b )-*', *-Si(R8a )(R 8b )-*', *-Ge(R 8a )(R 8b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 8a )=*', *=C(R 8a )-*', *-C(R 8a )=C(R 8b )-*', *-C(=S)-*', *-C≡C-*', 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 It is a heterocyclic group.

[0047] According to still another embodiment, in Formula 1, n4 is 1, 2, 3, or 4, and T4 is *-C(R 8a )(R 8b )-*', *-S-*', *-O-*', or at least one R 10a Substituted or unsubstituted C5-C 30 It is a carbocyclic group.

[0048] In the above formulas 1 and 2, R1 to R4, R 5a , R 5b , R 6a , R 6b , R 7a , R 7b , R 8a , R 8b , and Q 51 ~Q 53 are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, 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, 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 60Alkoxy 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 C7-C 60 Alkylaryl groups, substituted or unsubstituted C6-C 60 Aryloxy groups, substituted or unsubstituted C6-C 60 Arylthio groups, substituted or unsubstituted C1-C 60 Heteroaryl groups, substituted or unsubstituted C2-C 60 an alkylheteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), and Q is 51 ~Q 53 Each of these is not hydrogen, Q in the above chemical formula 2 51 ~Q 53 At least one of (e.g., Q 51 ~Q 53 one or two of) are each independently a substituted or unsubstituted C-C 60 Aryl groups, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0049] For example, R1 to R4, R 5a , R 5b , R6a , R 6b , R 7a , R 7b , R 8a , R 8b , and Q 51 ~Q 53 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, C2-C 20 Alkenyl 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 20alkyl)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, C2-C 20 Alkenyl 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, deuterated C2-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 20alkyl)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)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, isobenzothiazolyl 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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, 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 deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, -CD2CDH2, -CF3, -CF2H, -CFH2, -CH2CF3, -CH2CF2H, -CH2CFH2, -CHFCH3, -CHFCF2H, -CHFCFH2, -CHFCF3, -CF2CF3, -CF2CF2H, or -CF2CFH2; or Deuterium, -F, C1-C 10an 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;

[0050] According to one embodiment, Q 51 ~Q 53 are each independently a substituted or unsubstituted C-C 60 Alkyl groups, substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, but Q 51 ~Q 53 At least one of (e.g., Q 51 ~Q 53 One or two of) are substituted or unsubstituted C6-C 60 Aryl groups, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or a substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.

[0051] According to another embodiment, Q 51 ~Q 53 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 10 Alkyl groups, phenyl groups, (C1-C 20 C1-C alkyl)phenyl, biphenyl, terphenyl, naphthyl, pyridinyl, pyrimidinyl, or any combination thereof, substituted or unsubstituted. 20Alkyl groups, phenyl groups, (C1-C 20 alkyl)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, an isobenzothiazolyl group, a benzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group, an oxadiazolyl group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolyl group, a dibenzocarbazolyl group, an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolyl group, an azadibenzofuranyl group, or an azadibenzothiophenyl group, Q 51 ~Q 53 At least one of (e.g., Q 51 ~Q 53 one or two of) 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 10 Alkyl groups, phenyl groups, (C1-C 20 phenyl group, (C1-C alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof, substituted or unsubstituted; 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 salinyl group, quinazolinyl group, cinnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group.

[0052] According to still another embodiment, in Formulas 1 and 2, R1 to R4, R 5a , R 5b , R 6a , R 6b , R 7a , R 7b , R 8a , R 8b , and Q 51 ~Q 53 are each independently hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C2-C 10 Alkenyl groups, C1-C 10 Alkoxy groups, C1-C 10an alkylthio group, 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 9-237, a group in which at least one hydrogen atom in one of the following chemical formulas 9-201 to 9-237 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulas 9-201 to 9-237 is substituted with -F, a group represented by one of the following chemical formulas 10-1 to 10-129, a group in which at least one hydrogen atom in one of the following chemical formulas 10-1 to 10- 129 in which at least one hydrogen atom is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulae 10-1 to 10-129 is substituted with -F, a group represented by one of the following chemical formulae 10-201 to 10-350, a group in which at least one hydrogen atom in one of the following chemical formulae 10-201 to 10-350 is substituted with deuterium, a group in which at least one hydrogen atom in one of the following chemical formulae 10-201 to 10-350 is substituted with -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (for explanations of Q3 to Q5, see the respective locations described in this specification), Q 51 ~Q 53 Each of the is not hydrogen, but Q 51 ~Q 53 At least one of the groups represented by one of the following chemical formulas 10-12 to 10-129 is a group in which at least one hydrogen of one of the following chemical formulas 10-12 to 10-129 is substituted with deuterium, a group in which at least one hydrogen of one of the following chemical formulas 10-12 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, or a group in which at least one hydrogen of one of the following chemical formulas 10-201 to 10-350 is substituted with -F.

[0053] [ka] [ka]

[0054] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

[0055] According to yet another embodiment, Q 51 ~Q 53 are each independently -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, a group represented by one of the above chemical formulae 9-1 to 9-39, a group in which at least one hydrogen atom in one of the above chemical formulae 9-1 to 9-39 has been substituted with deuterium, a group in which at least one hydrogen atom in one of the above chemical formulae 9-1 to 9-39 has been substituted with -F, a group represented by one of the above chemical formulae 10-12 to 10-129, a group in which at least one hydrogen atom in one of the above chemical formulae 10-1 to 10-129 has been substituted with deuterium, or a group in which at least one hydrogen atom in one of the above chemical formulae 10-1 to 10-129 has been substituted with -F.

[0056] According to yet another embodiment, Q 51 ~Q 53 At least one of (e.g., Q 51 ~Q 53(one of the above) is a group represented by one of the above chemical formulas 10-12 to 10-129, a group in which at least one hydrogen of one of the above chemical formulas 10-1 to 10-129 has been substituted with deuterium, or a group in which at least one hydrogen of one of the above chemical formulas 10-1 to 10-129 has been substituted with -F.

[0057] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0058] The above "groups in which at least one hydrogen atom of chemical formulas 9-1 to 9-39 has been substituted with deuterium" and "groups in which at least one hydrogen atom of chemical formulas 9-201 to 9-237 has been substituted with deuterium" are, for example, groups represented by the following chemical formulas 9-501 to 9-514 and 9-601 to 9-636.

[0059] [ka] [ka]

[0060] The above "groups of chemical formulae 9-1 to 9-39 in which at least one hydrogen atom is substituted with -F" and the above "groups of chemical formulae 9-201 to 9-236 in which at least one hydrogen atom is substituted with -F" are, for example, groups represented by the following chemical formulae 9-701 to 9-710.

[0061] [ka]

[0062] The above "groups in which at least one hydrogen atom of chemical formulas 10-1 to 10-129 has been substituted with deuterium" and the above "groups in which at least one hydrogen atom of chemical formulas 10-201 to 10-350 has been substituted with deuterium" are, for example, groups represented by the following chemical formulas 10-501 to 10-553.

[0063] [ka] [ka]

[0064] The above "groups of chemical formulas 10-1 to 10-129 in which at least one hydrogen atom has been substituted with -F" and the following "groups of chemical formulas 10-201 to 10-350 in which at least one hydrogen atom has been substituted with -F" are, for example, groups represented by the following chemical formulas 10-601 to 10-617.

[0065] [ka]

[0066] In the above Chemical Formula 1, a1 to a4 respectively represent the number of R1 to R4, and each independently represents an integer of 0 to 20 (for example, 0, 1, 2, or 3). When a1 is 2 or more, two or more R1s are the same or different from each other; when a2 is 2 or more, two or more R2s are the same or different from each other; when a3 is 2 or more, two or more R3s are the same or different from each other; and when a4 is 2 or more, two or more R4s are the same or different from each other.

[0067] According to one embodiment, in Formula 1, i) a1, a2, a3, and a4 are 0 or ii) a1 is 1, 2, or 3, and a2, a3, and a4 are 0; or iii) a2 is 1 or 2, and a1, a3, and a4 are 0, or iv) a3 is 1 or 2, and a1, a2, and a4 are 0, or v) a4 is 1 and a1, a2, and a3 are 0, or vi) a1 and a4 are 1, and a2 and a3 are 0.

[0068] In the above formula 2, L1 is a single bond, 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 It is a heterocyclic group.

[0069] For example, in the above formula 1, L1 is a single bond; or At least one R 10asubstituted or unsubstituted cyclopentene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydrophthalene group, thiophene group, furan group, indole group, benzoborole group, benzophosphole group, indene group, benzosilole group, benzogermole group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborane group, dibenzothiophene, dibenzoselenophene, dibenzofuran, dibenzothiophene 5-oxide, 9H-fluoren-9-one, dibenzothiophene 5,5-dioxide, azaindole, azabenzoborole, azabenzophosphole, azaindene, azabenzosilole, azabenzogermole, azabenzothiophene, azabenzoselenophene, azabenzofuran, azabenzo ... 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, quinoxaline group, quinazoline group, phenanthro ... an anthroline 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, a 5,6,7,8-tetrahydroquinoline group, an adamantane group, a norbornane group, or a norbornene group.

[0070] According to one embodiment, L1 is: a single bond; or At least one R 10a a substituted or unsubstituted benzene group;

[0071] In the above chemical formula 2, c1 represents the number of L1 and is an integer of 1 to 10 (for example, 1, 2, or 3). When c1 is 2 or more, the two or more L1s are the same or different from each other.

[0072] In the above chemical formula 2, c2 is *-C(Q 51 )(Q 52 )(Q 53 ) (where * is a bonding site with the adjacent L1) and is an integer of 1 to 20 (for example, 1, 2, or 3). When c2 is 2 or more, 2 or more *-C(Q 51 )(Q 52 )(Q 53 ) are the same or different.

[0073] In the above formula 1, 1) two or more of the a1 R1 may be optionally bonded 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 2) two or more of the a2 R2 may optionally be bonded 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 form a heterocyclic group, and 3) two or more of the a3 R3 may optionally be bonded 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 4) two or more of the a4 R4 may optionally be bonded to each other, and at least one R 10a Substituted or unsubstituted C5-C 30a carbocyclic group, or at least one R 10a Substituted or unsubstituted C1-C 30 5) R1 to R4, R 5a , R 5b , R 6a , R 6b , R 7a , R 7b , R 8a , and R 8b two or more of the groups may optionally be bonded 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.

[0074] As used herein, R 10a For the explanation of R1, refer to the explanation of R1 in this specification.

[0075] According to one embodiment, in the above formula 1, n3 is not 0, and ring CY1 is a group represented by one of the following formulas CY1(1) to CY1(56) and CY1(101) to CY1(108):

[0076] [ka] [ka] [ka]

[0077] In the above chemical formulas CY1(1) to CY1(56) and the above chemical formulas CY1(101) to CY1(108), X1 is C or N, but in the above chemical formulae CY1(27) to CY1(39) and the above chemical formulae CY1(101) to CY1(108), X1 is C; X 11 is O, S, N(R 18 ), C(R 18)(R 19 ), or Si(R 18 )(R 19 ) and R 18 and R 19 For the explanation of each of R1, refer to the explanation of R1 in this specification. * is the bonding site with M in the above chemical formula 1, *' is the binding site with T3 in the above chemical formula 1, *" is the binding site for T4 in the above chemical formula 1.

[0078] According to another embodiment, in the above Formula 1, n3 is not 0 and n4 is 0; [ka] is a group represented by one of the following chemical formulas CY1-1 to CY1-41 and CY1-Z1 to CY1-Z69.

[0079] [ka] [ka] [ka] [ka] [ka]

[0080] In the above chemical formulas CY1-1 to CY1-41 and the above chemical formulas CY1-Z1 to CY1-Z69, X1 is C or N, but in the above chemical formulas CY1-22 to CY1-41 and the above chemical formulas CY1-Z32 to CY1-Z69, X1 is C; R1 and R 11 ~R 15Although the description of each of R1 and R2 is given in this specification, 11 ~R 15 Each of these is not hydrogen, Z 11 ~Z 15 For the explanation of each of the above, please refer to the explanation of Z1 in this specification. * is the bonding site with M in the above chemical formula 1, *' is the binding site for T3 in the above chemical formula 1.

[0081] According to still another embodiment, in the above formula 1, n1 is not 0, n3 is not 0, and ring CY2 is a group represented by one of the following formulas CY2(1) to CY2(15):

[0082] [ka]

[0083] In the above chemical formulas CY2(1) to CY2(15), X2 is C or N; X 21 is O, S, N(R 28 ), C(R 28 )(R 29 ), or Si(R 28 )(R 29 ) and R 28 and R 29 For the explanation of each of R2, refer to the explanation of R2 in this specification. *' is the binding site with T3 in the above chemical formula 1, * is the bonding site with M in the above chemical formula 1, *" is the binding site with T1 in the above chemical formula 1.

[0084] According to yet another embodiment, in the above Formula 1, n1 is not 0, n3 is not 0, [ka] is a group represented by one of the following chemical formulas CY2-1 to CY2-8 and CY2-Z1 to CY2-Z6.

[0085] [ka] [ka]

[0086] In the above chemical formulas CY2-1 to CY2-8 and the above chemical formulas CY2-Z1 to CY2-Z6, X1 is C or N; R2 and R 21 ~R 23 Although the description of each of R2 in this specification refers to the description of R2, 21 ~R 23 Each of these is not hydrogen, Z 21 ~Z 23 For the explanation of each of the above, please refer to the explanation of Z2 in this specification. *' is the binding site with T3 in the above chemical formula 1, * is the bonding site with M in the above chemical formula 1, *" is the binding site with T1 in the above chemical formula 1.

[0087] According to still another embodiment, in Formula 1, n1 is not 0, n2 is not 0, and ring CY3 is a group represented by the following formula CY3-A or CY3-B:

[0088] [ka]

[0089] In the above chemical formulas CY3-A and CY3-B, For the explanation of X3 and ring CY3, please refer to the respective sections described in this specification. Y 31 and Y 33are, independently of each other, C or N, and Y 32 is O, S, N, C, or Si, In the above chemical formula CY3-A, X3 and Y 33 The bond between X3 and Y 32 Bond with Y 32 and Y 31 and Y are each a chemical bond (e.g., a single bond or a double bond), and in the above chemical formula CY3-B, X3 and Y 31 and the bond between X3 and Y 33 is a chemical bond (e.g., a single bond or a double bond), *" is the binding site with T1 in the above chemical formula 1, * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1.

[0090] For example, in the above chemical formula 1, n1 is not 0, n2 is not 0, and ring CY3 is a group represented by the above chemical formula CY3-A.

[0091] According to still another embodiment, in Formula 1, n2 is not 0, n4 is 0, and ring CY4 is a group represented by the following formula CY4-A or CY4-B:

[0092] [ka]

[0093] In the above chemical formulas CY4-A and CY4-B, For the explanation of X4 and ring CY4, please refer to the respective sections described in this specification. Y 41 is C or N, and Y 42 is O, S, N, C, or Si, In the above chemical formula CY4-A, X4 and Y 41 The bond between X and Y is a chemical bond (e.g., a single bond or a double bond), and in the above chemical formula CY4-B, 42 Bond with Y 42 and Y 41and each bond is a chemical bond (e.g., a single bond or a double bond), * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1.

[0094] For example, in the above chemical formula 1, n2 is not 0, n4 is 0, and ring CY4 is a group represented by the above chemical formula CY4-A. According to another embodiment, in the above formula 1, n2 is not 0, T1 is a single bond, n4 is 0, ring CY3 is a group represented by the above formula CY3-A, and ring CY4 is a group represented by the above formula CY4-A.

[0095] According to yet another embodiment, in the above formula 1, n2 is not 0, T1 is a single bond, n4 is 0, ring CY3 is a group represented by the above formula CY3-B, and ring CY4 is a group represented by the above formula CY4-B. According to yet another embodiment, in the above formula 1, n2 is not 0, T1 is not a single bond, n4 is 0, ring CY3 is a group represented by the above formula CY3-B, and ring CY4 is a group represented by the above formula CY4-A.

[0096] According to another embodiment, in the above formula 1, n1 is not 0, and ring CY3 is a group represented by one of the following formulas CY3(1) to CY3(12) and CY3(101) to CY3(122):

[0097] [ka] [ka]

[0098] In the above chemical formulas CY3(1) to CY3(12) and the above chemical formulas CY3(101) to CY3(122), X3 is C or N; X 31is a single bond, O, S, N(R 38 ), C(R 38 )(R 39 ), or Si(R 38 )(R 39 ) and X 32 is O, S, N(R 38 ), C(R 38 )(R 39 ), or Si(R 38 )(R 39 ) and R 38 and R 39 For the explanation of each of the above, refer to the explanation of R3 in this specification. *" is the binding site with T1 in the above chemical formula 1, * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1.

[0099] According to yet another embodiment, in the above Formula 1, n1 is not 0, n2 is not 0, [ka] is a group represented by one of the following chemical formulas CY3-1 to CY3-16 and CY3-Z1 to CY3-Z10.

[0100] [ka] [ka]

[0101] In the above chemical formulas CY3-1 to CY3-16 and the above chemical formulas CY3-Z1 to CY3-Z10, X3 is C or N; R3, and R 31 ~R 36 The description of each of R3 in this specification refers to the description of R3. 31 ~R 36 Each of these is not hydrogen, Z 31 ~Z 36 For the explanation of each of the above, please refer to the explanation of Z3 in this specification. *" is the binding site with T1 in the above chemical formula 1, * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1.

[0102] According to still another embodiment, in the above formula 1, n2 is not 0, and ring CY4 is a group represented by one of the following formulas CY4(1) to CY4(42) and CY4(101) to CY4(111):

[0103] [ka] [ka] [ka]

[0104] In the above chemical formulas CY4(1) to CY4(42) and the above chemical formulas CY4(101) to CY4(111), X4 is C or N; X 41 is O, S, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ) and X 42 is a single bond, and O, S, N(R 48 ), C(R 48 )(R 49 ), or Si(R 48 )(R 49 ) and R 48 and R 49 For the explanation of each of the above, refer to the explanation of R4 in this specification. * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1, *" is the binding site for T4 in the above chemical formula 1.

[0105] According to yet another embodiment, in Formula 1, n2 is not 0 and n4 is 0;

[0106] [ka] is a group represented by one of the following chemical formulas CY4-1 to CY4-24 and CY4-Z1 to CY4-Z8.

[0107] [ka] [ka]

[0108] In the above chemical formulas CY4-1 to CY4-24 and the above chemical formulas CY4-Z1 to CY4-Z8, X4 is C or N; X 42 For the description of R4, and R 41 ~R 47 The description of each of R4 in this specification refers to the description of R4. 41 ~R 47 Each of these is not hydrogen, Z 41 ~Z 44 For the explanation of each of the above, please refer to the explanation of Z4 in this specification. * is the bonding site with M in the above chemical formula 1, *' is the binding site with T2 in the above chemical formula 1.

[0109] According to still another embodiment, in Formula 2, *-C(Q 51 )(Q 52 )(Q 53) is a group represented by one of the following chemical formulas 2-1 to 2-20.

[0110] [ka]

[0111] In the above chemical formulas 2-1 to 2-20, Q 51 , Q 52 , and Q 61 to Q65 are each independently a substituted or unsubstituted C1-C 60 is an alkyl group or a substituted or unsubstituted phenyl group, and Q 51 , Q 52 , and Q 61 ~Q 65 are the same or different, and * is the binding site with L1 in Chemical Formula 2.

[0112] For example, in the above chemical formulas 2-1 to 2-20, Q 51 , Q 52 , and Q 61 ~Q 65 are independently deuterium, C1-C 20 C1-C substituted or unsubstituted alkyl groups, phenyl groups, biphenyl groups, or any combination thereof 20 It is an alkyl group or a phenyl group.

[0113] For example, the group represented by the above chemical formula 2 is a group represented by one of the above chemical formulas 2-1 to 2-20, in which L1 is a single bond.

[0114] As yet another example, Z1 to Z4, Z 11 ~Z 15 , Z 21 ~Z 23 , Z 31 ~Z 36 , and Z 41 ~Z 44 are each independently a group represented by one of the above chemical formulas 2-1 to 2-20.

[0115] According to still another embodiment, the group represented by the above formula 2 is a group represented by one of the following formulas 2(1) to 2(19), in which L1 is a benzene group and c1 is 1.

[0116] [ka]

[0117] In the above chemical formulas 2(1) to 2(19), T 11 ~T 15 is the above chemical formula 2, *-C(Q 51 )(Q 52 )(Q 53 ) is a group represented by T 11 ~T 15 are the same or different, and R 10a For the explanation of *, refer to the explanation of R1 in this specification, and * is a binding site to at least one of rings CY1 to CY4 in Chemical Formula 1 above.

[0118] For example, in this specification, Z1 to Z4, Z 11 ~Z 15 , Z 21 ~Z 23 , Z 31 ~Z 36 , and Z 41 ~Z 44 are each independently a group represented by one of the above chemical formulas 2(1) to 2(19).

[0119] According to still another embodiment, the organometallic compound represented by Chemical Formula 1 satisfies at least one of the following <Condition 1> to <Condition 4>.

[0120] <Condition 1> In the above formula 1, n3 is not 0 and n4 is 0; [ka] is a group represented by one of the above chemical formulae CY1-Z1 to CY1-Z69, <Condition 2> In the above chemical formula 1, n1 is not 0, n3 is not 0, [ka] is a group represented by one of the above chemical formulae CY2-Z1 to CY2-Z6, <Condition 3> In the above chemical formula 1, n1 is not 0, n2 is not 0, [ka] is a group represented by one of the above chemical formulas CY3-Z1 to CY3-Z10, <Condition 4> In the above formula 1, n2 is not 0 and n4 is 0; [ka] is a group represented by one of the above chemical formulas CY4-Z1 to CY4-Z8.

[0121] According to yet another embodiment, the organometallic compound represented by Formula 1 emits blue light.

[0122] According to still another embodiment, the organometallic compound represented by Formula 1 is one of the following compounds: Compounds Pt-2, Pt-3, Pt-13, Pt-17, Pt-18, and Pt-21 are identical to compounds 4, 2009, 2076, 2132, 2133, and 2187, respectively.

[0123] [ka]

[0124] [ka] [ka] [ka]

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[0125] In the organometallic compound represented by Chemical Formula 1, Z1 to Z4 are each independently a group represented by Chemical Formula 2, and the sum of b1 to b4, which are the numbers of Z1 to Z4, is 1 or more. That is, the organometallic compound represented by Chemical Formula 1 is a substituent and contains at least one group represented by Chemical Formula 2. As a result, the organometallic compound represented by Chemical Formula 1 has an improved orientation rate without changing the conjugation length. In addition, in the group represented by Chemical Formula 2, *-C(Q 51 )(Q 52 )(Q53 ) does not contain hydrogen at the benzyl site containing a weak chemical bond (i.e., Q 51 ~Q 53 is not hydrogen), an organometallic compound containing at least one group represented by Chemical Formula 2 has excellent chemical and / or electrical stability. Therefore, the luminous efficiency and / or life of an electronic device, such as an organic light-emitting device, employing the organometallic compound represented by Chemical Formula 1 is improved.

[0126] The HOMO (highest occupied molecular orbital) energy level, LUMO (lowest unoccupied molecular orbital) energy level, S1 energy level, and T1 energy level of some of the organometallic compounds represented by Chemical Formula 1 were evaluated using the Gaussian09 program with molecular structure optimization by DFT (density functional theory) based on B3LYP. The results are shown in Table 1 below.

[0127] [Table 1]

[0128] 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 an emitting layer material in electronic devices, for example, organic light emitting devices.

[0129] 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.

[0130] Therefore, the organometallic compound represented by Chemical Formula 1 is suitable for use as an emitting layer material in an organic layer of an organic light-emitting device, for example, in the organic layer. 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 comprises at least one organometallic compound represented by Chemical Formula 1.

[0131] The organic light emitting device may have an excellent driving voltage, an excellent external quantum efficiency, a relatively narrow full width at half maximum (FWHM) of an EL (electroluminescence) spectrum emission peak, and an excellent lifespan characteristic by including an organic layer containing the organometallic compound represented by Chemical Formula 1 as described above.

[0132] 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 emitting layer. In this case, the emitting layer further includes a host. The content of the host is greater than the content of the organometallic compound. The emitting layer emits red light, green light, or blue light. For example, the organometallic compound emits blue light.

[0133] For example, the configuration of the light emitting layer is the following first embodiment or the following second embodiment.

[0134] <First Example>

[0135] The light-emitting layer includes an organometallic compound represented by Chemical Formula 1, and the organometallic compound serves as a phosphorescent emitter. For example, the light-emitting component emitted from the organometallic compound accounts for 80% or more, 85% or more, 90% or more, or 95% or more of the total light-emitting components in the light-emitting layer. The light emitted from the organometallic compound is blue light.

[0136] <Second embodiment>

[0137] In addition to the organometallic compound represented by Chemical Formula 1, the light-emitting layer further includes a phosphorescent dopant, a fluorescent dopant, or any combination thereof, which is different from the organometallic compound. Here, the organometallic compound acts as a sensitizer or auxiliary dopant, rather than a phosphorescent emitter. For example, the light-emitting layer further includes a fluorescent dopant, which is different from the organometallic compound, and the light-emitting component emitted from the fluorescent dopant accounts for 80% or more, 85% or more, 90% or more, or 95% or more of the total light-emitting components of the light-emitting layer.

[0138] In the second embodiment, the content of the fluorescent dopant is 1 to 100 parts by weight, 5 to 50 parts by weight, or 10 to 20 parts by weight per 100 parts by weight of the organometallic compound represented by Formula 1 above.

[0139] In the second embodiment, the total amount of the organometallic compound represented by Chemical Formula 1 and the fluorescent dopant is 1 to 30 parts by weight, 3 to 20 parts by weight, or 5 to 15 parts by weight per 100 parts by weight of the light-emitting layer.

[0140] The fluorescent dopant used in the second embodiment does not contain a transition metal.

[0141] For example, the fluorescent dopant used in the second embodiment is a fluorescent emitting material that does not contain a cyano group (-CN) or a fluoro group (-F).

[0142] In another example, the fluorescent dopant used in the second embodiment may be a fused ring-containing compound, an amino group-containing compound, a styryl group-containing compound, or a boron group-containing compound.

[0143] For example, the fluorescent dopant used in the second embodiment includes an amino group-containing compound.

[0144] According to one embodiment, the fluorescent dopant used in the second embodiment may include a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group (tetracene group), a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a group represented by one of the following chemical formulas 501-1 to 501-21, or any combination thereof.

[0145] [ka]

[0146] According to another embodiment, the fluorescent dopant used in the second embodiment includes a compound represented by the following formula 501A or 501B:

[0147] [ka]

[0148] In the above chemical formulas 501A and 501B, Ar 501 is a naphthalene group, a fluorene group, a spiro-bifluorene group, a benzofluorene group, a dibenzofluorene group, a phenanthrene group, an anthracene group, a fluoranthene group, a triphenylene group, a pyrene group, a chrysene group, a naphthacene group, a picene group, a perylene group, a pentaphene group, an indenoanthracene group, a bisanthracene group, or a group represented by one of the above chemical formulas 501-1 to 501-21, R 511 represents hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl 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, C3-C 10Cycloalkyl 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 condensed polycyclic group, a monovalent non-aromatic condensed heteropolycyclic group, or -Si(Q 501 )(Q 502 )(Q 503 ) and xd5 is an integer between 0 and 10, L 501 ~L 503 are each independently single bond; and Deuterium, -F, -Cl, -Br, -I, hydroxyl 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, 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, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof, substituted or unsubstituted, C3-C 10 Cycloalkylene groups, C1-C 10 Heterocycloalkylene groups, C3-C 10 Cycloalkenylene group, C1-C 10Heterocycloalkenylene group, C6-C 60 Arylene groups, C1-C 60 a heteroarylene group, a divalent non-aromatic fused polycyclic group, or a divalent non-aromatic fused heteropolycyclic group; xd1 to xd3 are each independently 1, 2, or 3; R 501 and R 502 are each independently deuterium, -F, -Cl, -Br, -I, a hydroxyl 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, 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, -Si(Q 501 )(Q 502 )(Q 503 ), or a phenyl group, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, a pyrenyl group, a chrysenyl group, a pyridinyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a quinolinyl group, an isoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, a carbazole group, a triazinyl group, a dibenzofuranyl group, a dibenzothiophenyl group, or a dibenzosilolyl group, substituted or unsubstituted with any combination thereof; Z 11represents deuterium, -F, -Cl, -Br, -I, hydroxyl 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, 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, -Si(Q 501 )(Q 502 )(Q 503 ), or any combination thereof, substituted or unsubstituted, 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, 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, xd4 is 1, 2, 3, 4, 5, or 6; Q 501 ~Q 503 are each independently hydrogen, C1-C 60 Alkyl groups, C1-C 60 Alkoxy groups, C6-C 60Aryl groups, C1-C 60 It is a heteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused polycyclic heterocyclic group.

[0149] According to another embodiment, the fluorescent dopant includes a compound represented by the above formula 501A or 501B, wherein in the above formula 501A, xd4 is 1, 2, 3, 4, 5, or 6, and in the above formula 501B, xd4 is 2, 3, or 4.

[0150] According to still another embodiment, the fluorescent dopant includes one of the following compounds FD(1) to FD(16), one of FD1 to FD16, or any combination thereof:

[0151] [ka] [ka]

[0152] [ka] [ka]

[0153] 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."

[0154] 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. In this case, 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).

[0155] 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.

[0156] 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, wherein 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.

[0157] In this specification, the term "organic layer" refers to a single layer 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.

[0158] 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.

[0159] A substrate is further disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in a general organic light-emitting device can be 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.

[0160] The first electrode 11 is formed by depositing a first electrode material on the substrate using, for example, a deposition method or a sputtering method. 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, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) may be used.

[0161] 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.

[0162] On top of the first electrode 11, an organic layer 15 is disposed.

[0163] Organic layers 15 include a hole transport region, an emissive layer, and an electron transport region.

[0164] The hole transport region is disposed between the first electrode 11 and the light-emitting layer.

[0165] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0166] 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.

[0167] 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.

[0168] 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 structure of the intended 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 The pressure is selected from the range of about 0.01 to about 100 Å / sec, but is not limited thereto.

[0169] 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, but is not limited thereto.

[0170] The conditions for forming the hole transport layer and the electron blocking layer refer to the conditions for forming the hole injection layer.

[0171] The hole transport region includes, 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.

[0172] [ka]

[0173] [ka] [ka]

[0174] 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 10 Heterocycloalkenyl 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.

[0175] 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, but is not limited thereto.

[0176] 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, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or salt thereof, sulfonic acid group or salt thereof, and phosphate group or salt thereof, or any combination thereof 10 Alkyl 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 an alkoxy group, or any combination thereof;

[0177] 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 20The alkyl group may be an alkoxy group, a phenyl group, a naphthyl group, an anthracenyl group, a pyridinyl group, or any combination thereof, substituted or unsubstituted, such as a phenyl group, a naphthyl group, an anthracenyl group, or a pyridinyl group.

[0178] According to one embodiment, the compound represented by Formula 201 is represented by Formula 201A below.

[0179] [ka]

[0180] In the above formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed description of the above, please refer to the above section.

[0181] For example, the hole transport region may include one of the compounds represented by the following formulas HT1 to HT20, or any combination thereof.

[0182] [ka] [ka]

[0183] 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.

[0184] 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.

[0185] The charge-generating material may be, for example, a p-dopant. The p-dopant may be, but is not limited to, a quinone derivative, a metal oxide, a cyano-containing compound, or any combination thereof. For example, the p-dopant may be a quinone derivative such as tetracyanoquinodimethane (TCNQ), 2,3,5,6-tetrafluorotetracyano-1,4-benzoquinodimethane (F4-TCNQ), or F6-TCNNQ; a metal oxide such as tungsten oxide or molybdenum oxide; a cyano-containing compound such as the following compound HT-D1; or any combination thereof.

[0186] [ka]

[0187] The hole transport region further includes a buffer layer.

[0188] The buffer layer compensates for the optical resonance distance depending on the wavelength of light emitted from the light emitting layer, thereby increasing efficiency.

[0189] On the other hand, when the hole transport region includes an electron blocking layer, the material of the electron blocking layer can be a material used in the hole transport region as described above, a host material as described below, or any combination thereof. For example, when the hole transport region includes an electron blocking layer, mCP as described below can be used as the material of the electron blocking layer.

[0190] 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, but are generally selected from approximately the same range of conditions as those for forming the hole injection layer.

[0191] The light-emitting layer comprises a host and a dopant, and the dopant comprises an organometallic compound represented by Formula 1 as described herein.

[0192] The host includes TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, mCP, Compound H50, Compound H51, Compound H52, or any combination thereof.

[0193] [ka]

[0194] 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.

[0195] 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, but is not limited thereto.

[0196] 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 are exhibited without a substantial increase in driving voltage.

[0197] An electron transport region is then placed on top of the light emitting layer.

[0198] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0199] For example, the electron transport region may have a structure of, but is not limited to, a hole blocking layer / electron transport layer / electron injection layer or an 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.

[0200] 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.

[0201] When the electron transport region includes a hole-blocking layer, the hole-blocking layer includes, for example, at least one of BCP, Bphen, and Balq.

[0202] [ka]

[0203] Alternatively, the hole-blocking layer may comprise a host, an electron-transporting layer material described below, an electron-injecting layer material, or any combination thereof.

[0204] 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.

[0205] The electron transport layer contains the above-mentioned BCP, Bphen, TPBi, the below-mentioned Alq3, Balq, TAZ, NTAZ, or any combination thereof.

[0206] [ka]

[0207] Alternatively, the electron transport layer includes one of the following compounds ET1 to ET25, or any combination thereof.

[0208] [ka] [ka]

[0209] 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.

[0210] The electron transport layer further contains a metal-containing material in addition to the materials described above.

[0211] The metal-containing substance includes a Li complex, for example, the following compound ET-D1 or ET-D2.

[0212] [ka]

[0213] The electron transport region also includes an electron injection layer that facilitates the injection of electrons from the second electrode 19 .

[0214] The electron injection layer comprises LiF, NaCl, CsF, Li2O, BaO, or any combination thereof.

[0215] 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.

[0216] 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 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 light-emitting element. Although the organic light-emitting device has been described above with reference to FIG. 1, it is not limited thereto.

[0217] 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.

[0218] In yet another aspect, there is provided a diagnostic composition comprising one or more organometallic compounds represented by Formula 1 above.

[0219] 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.

[0220] Diagnostic compositions are widely used in various diagnostic kits, diagnostic reagents, biosensors, biomarkers, and the like.

[0221] As used herein, C1-C 60 The 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.

[0222] As used herein, C1-C 60 Alkyl groups, C1-C20 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, substituted or unsubstituted with 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.

[0223] As used herein, C1-C 60 The alkoxy group is -OA. 101 (where A 101 is C1-C 60 means a monovalent group having the formula:

[0224] As used herein, C1-C 60 Alkoxy groups, C1-C 20 Alkoxy group or C1-C10 Examples of the alkoxy group include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, or a pentoxy group.

[0225] 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.

[0226] 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.

[0227] As used herein, C3-C 10 Cycloalkyl groups are C3-C 10 means a monovalent saturated hydrocarbon ring group, C3-C 10 The cycloalkylene group is C3-C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0228] As used herein, C3-C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, bicyclo[2.2.1]heptyl (norbornanyl), bicyclo[2.2.2]octyl, and the like.

[0229] As used herein, C1-C 10Heterocycloalkyl groups are C1-C10 alkyl groups containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom. 10 means a monovalent monocyclic group, C1-C 10 The heterocycloalkylene group is C1-C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0230] As used herein, C1-C 10 Examples of heterocycloalkyl groups include silolanyl, silnanyl, tetrahydrofuranyl, tetrahydro-2H-pyranyl, and tetrahydrothiophenyl groups.

[0231] As used herein, C3-C 10 The cycloalkenyl group is C3-C 10 It means a monovalent monocyclic 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.

[0232] As used herein, C1-C 10 The heterocycloalkenyl group is a C1-C6 alkyl group containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom. 10 It is a monovalent monocyclic group having 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.

[0233] As used herein, C6-C 60 The aryl group is C6-C60 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.

[0234] As used herein, C7-C 60 The alkylaryl group has at least one C-C 60 C6-C substituted with alkyl groups 60 It means an aryl group.

[0235] As used herein, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, and S 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, and S as a ring-forming atom, and is C1-C 60 means a divalent group having a carbocyclic aromatic system. C1-C 60 Specific 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.

[0236] 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.

[0237] 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).

[0238] 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, the ring atoms are carbon, and the entire molecule is non-aromatic. 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.

[0239] 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 contains, in addition to carbon, a heteroatom selected from N, O, P, Si, and S 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.

[0240] 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-forming atoms. 30 A carbocyclic group is a monocyclic group or a polycyclic group. 10a (substituted or unsubstituted) C5-C 30 A "carbocyclic group" is, for example, a group consisting of at least one R10a adamantane group (substituted or unsubstituted), 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-tetrahydrophthalene group, cyclopentadiene group, silole group, fluorene group, and the like.

[0241] As used herein, C1-C 30 The heterocyclic group refers to a saturated or unsaturated cyclic group having, as ring-forming atoms, 1 to 30 carbon atoms and at least one heteroatom selected from N, O, P, Si, and S. 30 The heterocyclic group is a monocyclic group or a polycyclic group. R10a (substituted or unsubstituted) C1-C 30 The "heterocyclic group" is, for example, (at least one R 10a(substituted or unsubstituted) thiophene group, furan group, pyrrole group, silole group, borole group, phosphole group, selenophene group, germole group, benzothiophene group, benzofuran group, indole group, indene group, benzosilole group, benzoborole group, benzophosphole group, benzoselenophene group, benzogermole group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzoborole group, dibenzophosphole group 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, aza Carbazole 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 , phenanthroline group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, and the like.

[0242] As used herein, "fluorinated C-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 each a C1-C6 substituted with at least one fluoro group (-F). 60 Alkyl group (or C1-C 20 alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 It refers to a heterocycloalkyl group, a phenyl group, and a fluorinated C1 alkyl group. For example, a "fluorinated C1 alkyl group (i.e., a fluorinated methyl group)" includes -CF3, -CF2H, and -CFH2. The above "fluorinated C1-C 60 Alkyl group (or fluorinated C1-C 20 alkyl groups), fluorinated C3-C 10 Cycloalkyl group, fluorinated C1-C 10 A "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 each group are replaced by 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.

[0243] As used herein, "deuterated C-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 C-C heterocycloalkyl groups substituted with at least one deuterium. 60 Alkyl group (or C1-C20 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 is the same as the above "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 10 A "heterocycloalkyl group" or a "deuterated phenyl group" refers to a fully deuterated C1-C12 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 C1-C1C group in which not all hydrogen atoms in the group are replaced with deuterium atoms. 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.

[0244] 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 "C3-C10 cycloalkyl" 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 C-C20 This refers to a phenyl group substituted with an alkyl group. An example of a (C1 alkyl)phenyl group is a toluyl group.

[0245] 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 It means a heterocycle having the same backbone as "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 in which at least one of the carbon atoms forming the ring is replaced with nitrogen.

[0246] 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 10Cycloalkenyl groups, substituted C1-C 10 Heterocycloalkenyl groups, substituted C6-C 60 Aryl groups, substituted C7-C 60 Alkylaryl groups, substituted C6-C 60 Aryloxy groups, substituted C6-C 60 Arylthio groups, substituted C1-C 60 Heteroaryl groups, substituted C2-C 60 The substituents of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic heterocyclic group are each independently: 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 group, or C1-C 60 Alkoxy 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(Q13 )(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 group, or C1-C 60 Alkoxy 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 an alkylheteroaryl group, a monovalent non-aromatic fused polycyclic group, or a monovalent non-aromatic fused heteropolycyclic group; 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, 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 60Aryloxy 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 with 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 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(Q 38 )(Q 39 ); or Any combination thereof;

[0247] In this specification, Q1 to Q9, Q 11 ~Q 19 , Q 21 ~Q 29 , and Q31 ~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 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; C3-C 10 Cycloalkyl group; 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.

[0248] Hereinafter, the compound and organic light-emitting device according to an embodiment of the present invention will be described in more detail with reference to synthesis examples and examples, but the present invention is not limited to the following 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.

[0249] [Example]

[0250] ≪Synthesis example 1 (compound Pt-1)≫

[0251] [ka]

[0252] <(1) Synthesis of intermediate Pt-1-IM2>

[0253] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (9.08 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of dimethyl sulfoxide (DMSO) and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-1-IM2 (7.42 g, 13 mmol, yield=65%). LC-MS (calculated value: 570.24 g / mol, measured value M+1 = 571 g / mol)

[0254] <(2) Synthesis of intermediate Pt-1-IM1>

[0255] Intermediate Pt-1-IM2 (7.42 g, 13 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (11.40 g, 19.5 mmol), and copper(II) acetate (0.24 g, 1.3 mmol) were mixed with 130 mL of dimethylformamide (DMF) and stirred at 100°C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-1-IM1 (10.05 g, 11.05 mmol, yield = 85%). LC-MS (calculated value: 759.41 g / mol, measured value M+1 = 759 g / mol)

[0256] <(3) Synthesis of Compound Pt-1>

[0257] Intermediate Pt-1-IM1 (5.00 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-1 (2.88 g, 3.03 mmol, yield = 55%). LC-MS (calculated value: 951.35 g / mol, measured value M+1 = 952 g / mol)

[0258] ≪Synthesis example 2 (compound Pt-2)≫

[0259] [ka]

[0260] <(1) Synthesis of intermediate Pt-2-IM2>

[0261] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (7.59 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-2-IM2 (6.92 g, 13.60 mmol, yield=68%). LC-MS (calculated value: 508.23 g / mol, measured value M+1 = 509 g / mol)

[0262] <(2) Synthesis of intermediate Pt-2-IM1>

[0263] Intermediate Pt-2-IM2 (6.92 g, 13.60 mmol), (3,5-bis(2-phenylpropan-2-yl)phenyl)(mesityl)iodonium triflate (14.45 g, 20.40 mmol), and copper(II) acetate (0.25 g, 1.36 mmol) were mixed with 136 mL of DMF and stirred at 100 °C for 4 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-2-IM1 (11.09 g, 11.42 mmol, yield = 84%). LC-MS (calculated value: 821.42 g / mol, measured value M+1 = 821 g / mol)

[0264] <(3) Synthesis of Compound Pt-2>

[0265] Intermediate Pt-2-IM1 (5.34 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-2 (2.96 g, 2.92 mmol, yield = 53%). LC-MS (calculated value: 1,013.36 g / mol, measured value M+1 = 1,014 g / mol)

[0266] ≪Synthesis Example 3 (Compound Pt-3)≫

[0267] [ka]

[0268] <(1) Synthesis of intermediate Pt-3-IM2>

[0269] 1-(3-Bromo-5-(2-phenylpropan-2-yl)phenyl)-1H-benzo[d]imidazole (7.83 g, 20 mmol), 9-(4-(tert-butyl)pyridin-2-yl)-9H-carbazol-2-ol (7.59 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-3-IM2 (7.77 g, 12.40 mmol, yield=62%). LC-MS (calculated value: 626.31 g / mol, measured value M+1 = 627 g / mol)

[0270] <(2) Synthesis of intermediate Pt-3-IM1>

[0271] Intermediate Pt-3-IM2 (7.77 g, 12.40 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (10.87 g, 18.60 mmol), and copper(II) acetate (0.23 g, 1.24 mmol) were mixed with 124 mL of DMF and stirred at 100 °C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-3-IM1 (11.09 g, 11.42 mmol, yield = 84%). LC-MS (calculated value: 815.47 g / mol, measured value M+1 = 816 g / mol)

[0272] <(3) Synthesis of Compound Pt-3>

[0273] Intermediate Pt-3-IM1 (5.31 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-3 (2.94 g, 2.92 mmol, yield = 53%). LC-MS (calculated value: 1,007.41 g / mol, measured value M+1 = 1,008 g / mol)

[0274] ≪Synthesis example 4 (compound Pt-4)≫

[0275] [ka]

[0276] <(1) Synthesis of intermediate Pt-4-IM2>

[0277] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 6-(tert-butyl)-9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (10.43 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-4-IM2 (8.40 g, 13.40 mmol, yield=67%). LC-MS (calculated value: 626.31 g / mol, measured value M+1 = 627 g / mol)

[0278] <(2) Synthesis of intermediate Pt-4-IM1>

[0279] Intermediate Pt-4-IM2 (8.40 g, 13.40 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (11.75 g, 20.10 mmol), and copper(II) acetate (0.24 g, 1.34 mmol) were mixed with 124 mL of DMF and stirred at 100 °C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-4-IM1 (11.09 g, 11.42 mmol, yield = 84%). LC-MS (calculated value: 815.47 g / mol, measured value M+1 = 816 g / mol)

[0280] <(3) Synthesis of Compound Pt-4>

[0281] Intermediate Pt-4-IM1 (5.31 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-4 (2.94 g, 2.92 mmol, yield = 53%). LC-MS (calculated value: 1,007.41 g / mol, measured value M+1 = 1,008 g / mol)

[0282] ≪Synthesis Example 5 (Compound Pt-5)≫

[0283] [ka]

[0284] <(1) Synthesis of intermediate Pt-5-IM2>

[0285] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 6-phenyl-9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (10.91 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-5-IM2 (6.86 g, 10.60 mmol, yield=53%). LC-MS (calculated value: 646.27 g / mol, measured value M+1 = 647 g / mol)

[0286] <(2) Synthesis of intermediate Pt-5-IM1>

[0287] Intermediate Pt-5-IM2 (6.86 g, 10.60 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.29 g, 15.90 mmol), and copper(II) acetate (0.19 g, 1.06 mmol) were mixed with 106 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-5-IM1 (8.56 g, 8.69 mmol, yield = 82%). LC-MS (calculated value: 835.44 g / mol, measured value M+1 = 836 g / mol)

[0288] <(3) Synthesis of Compound Pt-5>

[0289] Intermediate Pt-5-IM1 (5.42 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-5 (3.11 g, 3.03 mmol, yield = 55%). LC-MS (calculated value: 1,027.38 g / mol, measured value M+1 = 1,028 g / mol)

[0290] ≪Synthesis Example 6 (Compound Pt-6)≫

[0291] [ka]

[0292] <(1) Synthesis of intermediate Pt-6-IM2>

[0293] 1-(3-Bromo-5-(tert-butyl)phenyl)-1H-benzo[d]imidazole (6.58 g, 20 mmol), 9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (9.08 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-6-IM2 (6.64 g, 10.60 mmol, yield=53%). LC-MS (calculated value: 626.31 g / mol, measured value M+1 = 627 g / mol)

[0294] <(2) Synthesis of intermediate Pt-6-IM1>

[0295] Intermediate Pt-6-IM2 (6.64 g, 10.60 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.29 g, 15.90 mmol), and copper(II) acetate (0.19 g, 1.06 mmol) were mixed with 106 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-6-IM1 (8.29 g, 8.59 mmol, yield = 81%). LC-MS (calculated value: 815.47 g / mol, measured value M+1 = 816 g / mol)

[0296] <(3) Synthesis of Compound Pt-6>

[0297] Intermediate Pt-6-IM1 (5.31 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-6 (3.33 g, 3.30 mmol, yield = 60%). LC-MS (calculated value: 1,007.41 g / mol, measured value M+1 = 1,008 g / mol)

[0298] ≪Synthesis Example 7 (Compound Pt-7)≫

[0299] [ka]

[0300] <(1) Synthesis of intermediate Pt-7-IM1>

[0301] 1-(3-Bromophenyl)-3,5-dimethyl-1H-pyrazole (5.02 g, 20 mmol), 9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (9.08 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-7-IM1 (6.04 g, 11.00 mmol, yield=55%). LC-MS (calculated value: 548.26 g / mol, measured value M+1 = 549 g / mol)

[0302] <(2) Synthesis of Compound Pt-7>

[0303] Intermediate Pt-7-IM1 (3.02 g, 5.50 mmol) and PtCl2(PhCN)2 (2.11 g, 6.05 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-7 (2.24 g, 3.03 mmol, yield = 55%). LC-MS (calculated value: 741.21 g / mol, measured value M+1 = 742 g / mol)

[0304] ≪Synthesis Example 8 (Compound Pt-8)≫

[0305] [ka]

[0306] <(1) Synthesis of intermediate Pt-8-IM1>

[0307] 2-(3-Bromophenyl)-1-phenyl-1H-imidazole (5.98 g, 20 mmol), 9-(4-(2-phenylpropan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (9.08 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-8-IM1 (5.85 g, 9.80 mmol, yield=49%). LC-MS (calculated value: 596.26 g / mol, measured value M+1 = 597 g / mol)

[0308] <(2) Synthesis of Compound Pt-8>

[0309] Intermediate Pt-8-IM1 (3.28 g, 5.50 mmol) and PtCl2(PhCN)2 (2.11 g, 6.05 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-8 (2.43 g, 3.08 mmol, yield = 56%). LC-MS (calculated value: 789.21 g / mol, measured value M+1 = 790 g / mol)

[0310] ≪Synthesis Example 9 (Compound Pt-9)≫

[0311] [ka]

[0312] <(1) Synthesis of intermediate Pt-9-IM2>

[0313] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(1,1-diphenylethyl)pyridin-2-yl)-9H-carbazol-2-ol (10.56 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-9-IM2 (6.70 g, 10.60 mmol, yield=53%). LC-MS (calculated value: 632.26 g / mol, measured value M+1 = 633 g / mol)

[0314] <(2) Synthesis of intermediate Pt-9-IM1>

[0315] Intermediate Pt-9-IM2 (6.86 g, 10.60 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.29 g, 15.90 mmol), and copper(II) acetate (0.19 g, 1.06 mmol) were mixed with 106 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-9-IM1 (8.43 g, 8.69 mmol, yield = 82%). LC-MS (calculated value: 821.44 g / mol, measured value M+1 = 821 g / mol)

[0316] <(3) Synthesis of Compound Pt-9>

[0317] Intermediate Pt-9-IM1 (5.34 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-9 (3.07 g, 3.03 mmol, yield = 55%). LC-MS (calculated value: 1,013.36 g / mol, measured value M+1 = 1,014 g / mol)

[0318] ≪Synthesis Example 10 (Compound Pt-10)≫

[0319] [ka]

[0320] <(1) Synthesis of intermediate Pt-10-IM2>

[0321] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(1,1-diphenylethyl)pyridin-2-yl)-6-phenyl-9H-carbazol-2-ol (12.39 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-10-IM2 (7.08 g, 10.00 mmol, yield=50%). LC-MS (calculated value: 708.29 g / mol, measured value M+1 = 709 g / mol)

[0322] <(2) Synthesis of intermediate Pt-10-IM1>

[0323] Intermediate Pt-10-IM2 (7.08 g, 10.00 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (8.76 g, 15.00 mmol), and copper(II) acetate (0.19 g, 1.00 mmol) were mixed with 100 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-10-IM1 (8.37 g, 8.00 mmol, yield = 80%). LC-MS (calculated value: 897.45 g / mol, measured value M+1 = 898 g / mol)

[0324] <(3) Synthesis of Compound Pt-10>

[0325] Intermediate Pt-10-IM1 (5.76 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-10 (3.06 g, 2.81 mmol, yield = 51%). LC-MS (calculated value: 1,089.40 g / mol, measured value M+1 = 1,090 g / mol)

[0326] ≪Synthesis Example 11 (Compound Pt-13)≫

[0327] [ka]

[0328] <(1) Synthesis of intermediate Pt-13-IM2>

[0329] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(tert-butyl)pyridin-2-yl)-6-(2-phenylpropan-2-yl)-9H-carbazol-2-ol (10.42 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-13-IM2 (6.89 g, 11.00 mmol, yield=55%). LC-MS (calculated value: 626.31 g / mol, measured value M+1 = 627 g / mol)

[0330] <(2) Synthesis of intermediate Pt-13-IM1>

[0331] Intermediate Pt-13-IM2 (6.89 g, 11.00 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.64 g, 16.50 mmol), and copper(II) acetate (0.20 g, 1.10 mmol) were mixed with 110 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-13-IM1 (8.49 g, 8.80 mmol, yield = 80%). LC-MS (calculated value: 815.47 g / mol, measured value M+1 = 816 g / mol)

[0332] <(3) Synthesis of Compound Pt-13>

[0333] Intermediate Pt-13-IM1 (5.30 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-13 (2.83 g, 2.81 mmol, yield = 51%). LC-MS (calculated value: 1,007.41 g / mol, measured value M+1 = 1,008 g / mol)

[0334] ≪Synthesis Example 12 (Compound Pt-17)≫

[0335] [ka]

[0336] <(1) Synthesis of intermediate Pt-17-IM2>

[0337] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(2-(4-(tert-butyl)phenyl)propan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (10.42 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-17-IM2 (6.89 g, 11.00 mmol, yield=55%). LC-MS (calculated value: 626.31 g / mol, measured value M+1 = 627 g / mol)

[0338] <(2) Synthesis of intermediate Pt-17-IM1>

[0339] Intermediate Pt-17-IM2 (6.89 g, 11.00 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.64 g, 16.50 mmol), and copper(II) acetate (0.20 g, 1.10 mmol) were mixed with 110 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-17-IM1 (8.49 g, 8.80 mmol, yield = 80%). LC-MS (calculated value: 815.47 g / mol, measured value M+1 = 816 g / mol)

[0340] <(3) Synthesis of Compound Pt-17>

[0341] Intermediate Pt-17-IM1 (5.30 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-17 (2.94 g, 2.92 mmol, yield = 53%). LC-MS (calculated value: 1,007.41 g / mol, measured value M+1 = 1,008 g / mol)

[0342] ≪Synthesis Example 13 (Compound Pt-18)≫

[0343] [ka]

[0344] <(1) Synthesis of intermediate Pt-18-IM2>

[0345] 1-(3-Bromophenyl)-1H-benzo[d]imidazole (5.46 g, 20 mmol), 9-(4-(2-(3,5-di-tert-butylphenyl)propan-2-yl)pyridin-2-yl)-9H-carbazol-2-ol (11.78 g, 24 mmol), copper(I) iodide (0.76 g, 4 mmol), picolinic acid (0.98 g, 8 mmol), and tripotassium phosphate (12.7 g, 60 mmol) were mixed with 133 mL of DMSO and stirred at 120°C for 12 hours. After the reaction was completed, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-18-IM2 (7.78 g, 11.40 mmol, yield=57%). LC-MS (calculated value: 682.37 g / mol, measured value M+1 = 683 g / mol)

[0346] <(2) Synthesis of intermediate Pt-18-IM1>

[0347] Intermediate Pt-18-IM2 (7.78 g, 11.40 mmol), (3,5-di-tert-butylphenyl)(mesityl)iodonium triflate (9.99 g, 17.10 mmol), and copper(II) acetate (0.21 g, 1.14 mmol) were mixed with 114 mL of DMF and stirred at 100°C for 4 hours. After the reaction was complete, the mixture was cooled to room temperature and extracted with saturated ammonium chloride (NH4Cl) and ethyl acetate (EA). The organic layer was dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain intermediate Pt-18-IM1 (9.66 g, 9.46 mmol, yield = 83%). LC-MS (calculated value: 871.53 g / mol, measured value M+1 = 872 g / mol)

[0348] <(3) Synthesis of Compound Pt-18>

[0349] Intermediate Pt-18-IM1 (5.62 g, 5.50 mmol), Pt(COD)Cl2 (2.26 g, 6.05 mmol), and sodium acetate (1.35 g, 16.50 mmol) were mixed with 275 mL of benzonitrile and stirred at 180 °C for 18 hours. After the reaction was completed, the mixture was cooled to room temperature and concentrated under reduced pressure. The resulting product was subjected to silica gel column chromatography to obtain compound Pt-18 (3.22 g, 3.03 mmol, yield = 55%). LC-MS (calculated value: 1,063.47 g / mol, measured value M+1 = 1,064 g / mol)

[0350] <Evaluation example 1: PL (photoluminescence) spectrum evaluation>

[0351] Compound Pt-1 was diluted in toluene to a concentration of 10 mM, and then its photoluminescence (PL) spectrum was measured at room temperature using an ISC PC1 spectrofluorometer equipped with a xenon lamp. This was repeated for compounds Pt-2 to Pt-6, Pt-9, Pt-10, Pt-13, Pt-17, and Pt-18. The maximum emission wavelength and full width at half maximum (FWHM) of each compound are shown in Table 2.

[0352] [Table 2]

[0353] [ka]

[0354] From Table 2 above, it can be seen that the compounds Pt-1 to Pt-6, Pt-9, Pt-10, Pt-13, Pt-17, and Pt-18 emit blue light with a narrow half-width.

[0355] Example 1

[0356] A glass substrate with a 1,500 Å thick ITO (indium tin oxide) electrode (first electrode, anode) was ultrasonically cleaned with distilled water. After the distilled water cleaning, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol in that order, and then dried. After that, the substrate was transferred to a plasma cleaner and cleaned using oxygen plasma for 5 minutes, and then transferred to a vacuum deposition machine.

[0357] Compound HT3 was vacuum-deposited on the ITO electrode of the glass substrate to form a first hole-injection layer 3,500 Å thick. Compound HT-D1 was vacuum-deposited on the first hole-injection layer to form a second hole-injection layer 300 Å thick. TAPC was vacuum-deposited on the second hole-injection layer to form an electron-blocking layer 100 Å thick, thereby forming a hole-transport region.

[0358] On the hole transport region, the compound H52 and the compound Pt-1 (10 wt %) were co-deposited to form a light emitting layer having a thickness of 300 Å.

[0359] Compound ET3 was vacuum-deposited on the light-emitting layer to form a 250 Å-thick electron-transporting layer. ET-D1(Liq) was then vacuum-deposited on the electron-transporting layer to form a 5 Å-thick electron-injecting layer. Finally, a 1,000 Å-thick Al second electrode (cathode) was formed on the electron-injecting layer to fabricate an organic light-emitting device.

[0360] [ka]

[0361] Examples 1 to 6 and Comparative Examples A and B

[0362] An organic light emitting device was fabricated using the same method as in Example 1, except that the compound listed in Table 3 was used as the dopant in place of Compound Pt-1 when forming the light emitting layer.

[0363] <Evaluation Example 2: Characterization of organic light-emitting devices>

[0364] For each of the organic light-emitting devices fabricated in Examples 1 to 6 and Comparative Examples A and B, the maximum emission wavelength of the EL spectrum, the driving voltage, the external quantum efficiency, and the lifetime (LT 95 The results are shown in Table 3. 95 The luminance was evaluated by measuring the time it took for the luminance to reach 95% of the initial luminance of 100%. The maximum emission wavelength of the EL spectrum was measured for each organic light-emitting device using a luminance meter (Minolta CS-1000A) at 1,000 cd / m 2 The driving voltage and external quantum luminous efficiency were evaluated using a current-voltage meter (Keithley 2400) and a luminance meter (Minolta CS-1000A). In Table 3, the driving voltage, external quantum luminous efficiency, and lifetime of the organic light-emitting devices of Examples 1 to 6 and Comparative Examples A and B are all shown as relative values ​​(%).

[0365] [Table 3]

[0366] [ka]

[0367] From Table 3 above, it can be seen that the organic light-emitting devices of Examples 1 to 6 have improved driving voltage, improved external quantum luminescence efficiency, and improved life characteristics compared to the organic light-emitting devices of Comparative Examples A and B.

[0368] Example 7

[0369] An organic light-emitting device was fabricated using the same method as in Example 1, except that when forming the light-emitting layer, CBP, Compound Pt-1, and Compound FD16 were co-deposited in a weight ratio of 88.5:10:1.5 instead of Compound H52 and Compound Pt-1.

[0370] Comparative Example C

[0371] An organic light emitting device was fabricated using the same method as in Example 1, except that, when forming the light emitting layer, CBP and compound FD16 were deposited in a weight ratio of 90:10 instead of compound H52 and compound Pt-1.

[0372] Evaluation Example 3: Characterization of organic light-emitting devices

[0373] For each of the organic light-emitting devices fabricated in Example 7 and Comparative Example C, the maximum emission wavelength of the EL spectrum, the driving voltage, the external quantum efficiency, and the lifetime (LT 95 ) were evaluated, and the results are shown in Table 4. In Table 4, the driving voltage, external quantum luminous efficiency, and lifetime of the organic light-emitting devices of Example 7 and Comparative Example C are all shown as relative values ​​(%).

[0374] [Table 4]

[0375] [ka]

[0376] From Table 4 above, it can be seen that the organic light emitting device of Example 7 has improved driving voltage, improved external quantum efficiency, and improved life characteristics compared to the organic light emitting device of Comparative Example C.

[0377] 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]

[0378] 10 Organic light-emitting device 11 1st electrode 15 Organic layer 19 Second electrode

Claims

1. An organometallic compound represented by the following chemical formula 1: 【Chemical 1】 In Formula 1, M is Pt; In the above formula 1, X １ ~X ３ is C and X ４ is N, In the above formula 1, X １ and M, X ２ and M, X ３ and M, and X ４ two of the bonds between M and M are coordinate bonds and the remaining two are covalent bonds; In the above formula 1, Z １ ~Z ４ are each independently a group represented by the following chemical formula 2: 【Chemistry 2】 In the formula 1, b1 to b4 are each independently an integer of 0 to 3, and the sum of b1 to b4 is 1 or more; In Formula 1, the ring CY １ is a group represented by the following chemical formula CY1(30), 【CY1(30)】 In the chemical formula CY1(30), X １ is C, * is a bonding site with M in Chemical Formula 1; *' represents T in Chemical Formula 1 ３ is the binding site for In Formula 1, the ring CY ２ is a group represented by the following chemical formula CY2(1), 【CY2(1)】 In the chemical formula CY2(1), X ２ is C, *' represents T in Chemical Formula 1. ３ is the binding site for * is a bonding site with M in Chemical Formula 1; *" represents T in Chemical Formula 1. １ is the binding site for In Formula 1, the ring CY ３ is a group represented by the following chemical formula CY3(1), 【CY3(1)】 In the chemical formula CY3(1), X ３ is C, X ３１ is a single bond, *" represents T in Chemical Formula 1. １ is the binding site for * is a bonding site with M in Chemical Formula 1; *' represents T in Chemical Formula 1. ２ is the binding site for In Formula 1, the ring CY ４ is a group represented by the following chemical formula CY4(1), 【CY4(1)】 In the chemical formula CY4(1), X ４ is N, * is a bonding site with M in Chemical Formula 1; *' represents T in Chemical Formula 1. ２ is the binding site for In the chemical formula 1, T １ is *-N(R ５ａ )-*', *-B(R ５ａ )-*', *-P(R ５ａ )-*', *-C(R ５ａ ) (R ５ｂ )-*', *-Si(R ５ａ ) (R ５ｂ )-*', *-Ge(R ５ａ ) (R ５ｂ )-*', *-S-*', *-Se-*', or *-O-*'; In the chemical formula 1, T ２ is a single bond, In the chemical formula 1, T ３ is a single bond, In Formula 1, n1 to n3 are 1, and n4 is 0; In Formula 1, when n4 is 0, T ４ does not exist, In Formula 1, R １ ~R ４ , R ５ａ and R 5b 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 １ -C ６０ Alkoxy group, substituted or unsubstituted C １ -C ６０ alkylthio group, substituted or unsubstituted C ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C ６ -C ６０ aryl group, substituted or unsubstituted C ７ -C ６０ alkylaryl groups, 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 Heteroaryl group, substituted or unsubstituted C ２ -C ６０ alkylheteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic group, —Si(Q ３ ) (Q ４ ) (Q ５ ), or -Ge(Q ３ ) (Q ４ ) (Q ５ ) and Q in Formula 2 ５１ and Q 52 are each independently a C 1 -C 60 alkyl group unsubstituted or substituted with at least one deuterium; In Formula 2, Q 53 represents a C substituted or unsubstituted with at least one deuterium. ６ -C ６０ is an aryl group, In Formula 1, a1 is an integer of 0 to 5, a2 is an integer of 0 to 3, a3 is an integer of 0 to 6, and a4 is an integer of 0 to 4; In the above formula 2, L １ is a single bond or a benzene group unsubstituted or substituted with at least one deuterium; In the above Chemical Formula 2, c1 is 1; In the above Chemical Formula 2, c2 is 1 or 2; * and *' are bonding sites with adjacent atoms, The substituted C １ -C ６０ Alkyl groups, substituted C ２ -C ６０ Alkenyl groups, substituted C １ -C ６０ Alkoxy groups, substituted C １ -C ６０ Alkylthio group, substituted C ３ -C １０ Cycloalkyl groups, substituted C ６ -C ６０ Aryl groups, substituted C ７ -C ６０ Alkylaryl groups, substituted C ６ -C ６０ Aryloxy groups, substituted C ６ -C ６０ Arylthio groups, substituted C １ -C ６０ Heteroaryl groups, substituted C ２ -C ６０ The substituents of the alkylheteroaryl 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, C ２ -C ６０ Alkenyl group, or C １ -C ６０ an alkoxy group; Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano groups, or any combination thereof; １ -C ６０ Alkyl group, C ２ -C ６０ Alkenyl group, or C １ -C ６０ an alkoxy 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 １ -C ６０ Alkoxy 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; -Si(Q ３３ ) (Q ３４ ) (Q ３５ ), or -Ge(Q ３３ ) (Q ３４ ) (Q ３５ ); or any combination thereof; Q ３ ~Q ５ and Q ３３ ~Q ３５ each independently represents a deuterium-substituted or unsubstituted C １ -C ６０ an alkyl group; or Deuterium, C １ -C ６０ Alkyl group, C ６ -C ６０ C substituted or unsubstituted with aryl groups, or any combination thereof ６ -C ６０ an aryl group;

2. In the above formula 1, X １ 2. The organometallic compound according to claim 1, wherein the bond between and M is a coordinate bond.

3. In the formula 2, *-C(Q ５１ ) (Q ５２ ) (Q ５３ 2. The organometallic compound according to claim 1, wherein the group represented by the formula: 【(2-1)-(2-20)】 In the chemical formulas 2-1 to 2-20, Q ５１ and Q 52 each independently represent a C substituted or unsubstituted with at least one deuterium. １ -C ６０ is an alkyl group, and Q 61 to Q ６５ is deuterium, * indicates chemical formula 2, L １ It is the binding site for

4. The organometallic compound according to claim 1, wherein the group represented by Chemical Formula 2 is a group represented by one of the following Chemical Formulas 2(1) to 2(10): 【Chemistry 2(1)-2(10)】 In the chemical formulas 2(1) to 2(10), T １１ ~T １５ is the formula 2, *-C(Q ５１ ) (Q ５２ ) (Q ５３ ) is a group represented by T １１ ~T １５ are the same or different from each other, R 10a is deuterium; * indicates ring CY1 to ring CY in Chemical Formula 1. ４ It is a binding site with at least one of the following:

5. A first electrode; A second electrode; an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer; 5. An organic light-emitting device, wherein the organic layer contains one or more organometallic compounds according to claim 1.

6. 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, or any combination thereof; The organic light-emitting device of claim 5 , wherein the electron transport region comprises a hole-blocking layer, an electron-transporting layer, an electron-injecting layer, or any combination thereof.

7. The organic light-emitting device according to claim 5 , wherein the organometallic compound is contained in the light-emitting layer.

8. The organic light emitting device according to claim 7 , wherein the light emitting layer further comprises a host.

9. The organic light emitting device according to claim 7, wherein the light emitting component released from the organometallic compound accounts for 80% or more of the total light emitting component of the light emitting layer.

10. The organic light-emitting device according to claim 9, wherein the light emitted from the organometallic compound is blue light.

11. the light-emitting layer further comprises a fluorescent dopant; The fluorescent dopant is different from the organometallic compound and is The organic light emitting device of claim 7, wherein the light emitting component emitted from the fluorescent dopant accounts for 80% or more of the total light emitting component of the light emitting layer.

12. The organic light-emitting device according to claim 11, wherein the fluorescent dopant comprises an amino group-containing compound.

13. An electronic device comprising the organic light-emitting device according to claim 5 .

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