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

Abstract

To provide an organometallic compound, and an organic light-emitting device and a diagnostic composition, each including the organometallic compound.SOLUTION: The present invention provides an organometallic compound, represented by e.g., formula 2, 3, 4, or 17 (formula A is a comparative example), and an organic light-emitting device and a diagnostic composition, each including the organometallic compound.SELECTED DRAWING: Figure 1

Description

[Technical field]

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

[0002] An organic light emitting device is a self-emitting device that has excellent viewing angle, response time, luminance, driving voltage, and response speed, and is capable of being made multicolored.

[0003] According to one example, an organic light emitting device has an organic layer including an anode, a cathode, and 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 move to the emitting layer via the hole transport region, and electrons injected from the cathode move 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.

[0004] Furthermore, luminescent compounds, for example phosphorescent compounds, are also used for monitoring, sensing, detection, and the like of biological substances such as various cells and proteins. Summary of the Invention [Problem to be solved by the invention]

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

[0006] The organometallic compound according to one embodiment of the present invention, which has been made to achieve the above object, is represented by the following chemical formula 1-2 or 1-2(1). [ka] [ka] In the above chemical formula 1-2 or 1-2(1), M is platinum (Pt); X 1 Or X 4 , Y 41 , and Y 42 are each independently C or N; Y 43 and Y 44 are, independently of each other, C or N, A 3 is a chemical bond, X 1 and M, X 2 and M, X 3 and M, and X 4 Two of the bonds between and M are coordinate bonds and the remaining two are covalent bonds; Z 11 is C(R 11 ), and Z 12 is C(R 12 ), and Z 13 is C(R 13 ) and R 11 Or R 13 The explanation for ,under Record R 1 Explanation of is the same as , A 11 is *-C(R 8a )(R 9a )-*', Z 21 is N or C(R 21 ), and Z 22 is N or C(R 22 ), and Z 23 is N or C(R 23 ), and Z 24 is N or C(R 24 ), and Z 25 is N or C(R 25 ), and Z 26 is N or C(R 26) and R 21 Or R 26 For details on each, see the following R 2 Explanation of is the same as , The moiety represented by TIFF0007630578000003.tif34128 is represented by the chemical formula A1-1(1): The moiety represented by TIFF0007630578000004.tif49128 is represented by the following chemical formula CY3-1, [ka] In the chemical formula A1-1(1) and the chemical formula CY3-1, a14 is selected from the group consisting of integers of 0 to 4; Z 31 is N or C(R 31 ) and Z 32 is N or C(R 32 ) and R 31 and R 32 is R 3 is equivalent to R 31 and R 32 For explanations of each, see below. 3 Explanation of is the same as , Z 51 is N or C(R 51 ) and Z 52 is N or C(R 52 ) and Z 53 is N or C(R 53 ) and Z 54 is N or C(R 54 ) and R 51 ~R 54 is R 5 is equivalent to R 51 ~R 54For explanations of each, see below. 5 Explanation of is the same as , In the above Chemical Formula A1-1(1), * is a bonding site to M in Chemical Formula 1, and *' is a bonding site to an adjacent atom in Chemical Formula 1, In the formula CY3-1, the two *'s are binding sites with M in the formula 1, and *' is T in the formula 1. 2 It is a binding site for T 2 is *-N(R 8 )-*', *-B(R 8 )-*', *-C(R 8 )(R 9 )-*',*-Si(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', or *-S(=O) 2 -*', R 1 ~R 5 , R 8 , R 9 , R 8a and R 9a are independent of each other, Hydrogen, deuterium, -F, cyano group C 1 -C 20 Alkyl groups; Deuterium, -F, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 10 C substituted with at least one of an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; 1 -C 20 Alkyl groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, C 1 -C 20 Alkylphenyl groups, naphthyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups and dibenzothiophenyl groups; Deuterium, -F, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , cyano group, C 1 -C 20 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, C 1 -C 20 A cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, C, which are substituted with at least one selected from the group consisting of an alkylphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group. 1 -C 20 Alkylphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and -Si(Q 3 )(Q 4 )(Q 5 ); Q 3 Or Q 5 are independent of each other, -CH 3 , -CD 3 , -CD 2 H, -CDH 2, -CH 2 CH 3 , -CH 2 CD 3 , -CH 2 CD 2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2 CH 3 , -CD 2 CD 3 , -CD 2 CD 2 H and -CD 2 CDH 2 ; n-Propyl group, isopropyl phenyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl and naphthyl; and Deuterium, C 1 -C 10 n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl and naphthyl groups, each of which is substituted with at least one selected from the group consisting of an alkyl group and a phenyl group; a1 and a5 are each independently selected from integers of 0 to 4; a3 is selected from integers of 0 to 2; a4 is 0 or 1.

[0007] The organic light-emitting element according to one embodiment of the present invention, which has been made to achieve the above-mentioned object, comprises a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode and including an emitting layer, wherein the organic layer includes one or more of the organometallic compounds. In the organic layer, the organometallic compound may act as a dopant.

[0008] In order to achieve the above object, a diagnostic composition according to one embodiment of the present invention includes one or more organometallic compounds represented by Chemical Formula 1. Effect of the Invention

[0009] The organometallic compound of the present invention has excellent electrical properties and / or thermal stability, and an organic light-emitting device using the organometallic compound has improved luminous efficiency, external quantum efficiency, roll-off ratio, and life characteristics. In addition, since the organometallic compound of the present invention has excellent phosphorescence emission properties, a diagnostic composition having high diagnostic efficiency can be provided by utilizing the organometallic compound. [Brief description of the drawings]

[0010] [Figure 1] 1 is a cross-sectional view illustrating an organic light emitting device according to an embodiment. [Diagram 2] 1 shows PL spectra of compounds 3 and 17. [Diagram 3] 1 shows EL spectra of the organic light-emitting devices of Example 1 and Comparative Example A. [Figure 4] 1 is a graph showing the driving voltage vs. current density of the organic light-emitting element of Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] Specific examples for carrying out the present invention will now be described in detail.

[0012] The organometallic compound is represented by the following chemical formula 1.

[0013] [ka]

[0014] In the above formula 1, M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au).

[0015] According to one embodiment, M is, but is not limited to, Pt, Pd, or Au.

[0016] In the above formula 1, X 1 Or X 4 , Y 41 , and Y 42 are each independently C or N; Y 43 and Y 44 are each independently C, N, O, S, or Si.

[0017] According to one embodiment, in Formula 1, i)X 1 and X 4 is N and X 2 and X 3 is C or ii) X 1 and X 3 is C and X 2 and X 4 is N, but is not limited thereto.

[0018] In the above chemical formula 1, A 1 Or A 3 are each independently a chemical bond (e.g., a coordinate bond, a covalent bond, etc.), O, S, B(R'), N(R'), P(R'), C(R')(R"), Si(R')(R"), Ge(R')(R"), C(=O), B(R')(R"), N(R')(R"), or P(R')(R"); A 1 If is a chemical bond, X 1 and M are directly bonded, and A 2 If is a chemical bond, X2 and M are directly bonded, and A 3 If is a chemical bond, X 3 and M are directly bonded to each other. For the explanation of R' and R", please refer to the portions described in this specification.

[0019] In the above formula 1, X 1 Or A 1 and bond with M, X 2 Or A 2 and bond with M, X 3 Or A 3 and the bond with M, and X 4 Two of the bonds between and M are coordinate bonds, and the remaining two are covalent bonds, so that the organometallic compound represented by the above chemical formula 1 is electrically neutral.

[0020] According to one embodiment, in Formula 1, A 1 Or A 3 is a chemical bond, i)X 1 and M, and X 4 The bond between X and M is a coordinate bond. 2 the bond between X and M and the bond between X and M are covalent bonds; or ii) X 1 and M, and X 3 The bond between and M is a covalent bond, and X 2 and M, and X 4 The bond between and M is, but is not limited to, a coordinate bond.

[0021] In the above formula 1, the ring CY 1 Or CY 3 , and ring CY 5 are each independently 5 -C 30 Carbocyclic group or C 1 -C 30 Heterocyclic group, ring CY 4 is a five-membered ring, and the ring CY 5a is a six-membered ring. Here, the ring CY 4 X 4 , Y41 , Y 42 , Y 43 , and Y 44 Three or more (eg, three or four) of are N.

[0022] According to one embodiment, the ring CY 1 Or CY 3 , and ring CY 5 are each independently selected from i) a first ring, ii) a second ring, iii) a fused ring in which two or more first rings are fused, iv) a fused ring in which two or more second rings are fused, and v) a fused ring in which one or more first rings are fused with one or more second rings, and the first ring is a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group, a silole group, an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilol group, and a triazasilol group, and the second ring is selected from an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, a cyclohexene group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, and a triazine group.

[0023] In another embodiment, the ring CY 1 Or CY 3 , and ring CY 5each independently represents a benzene group, a naphthalene group, an anthracene group, a phenanthrene group, a triphenylene group, a pyrene group, a chrysene group, a cyclopentadiene group, a 1,2,3,4-tetrahydronaphthalene group, a thiophene group, a furan group, an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole group, a benzogermole group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborole group, a dibenzophosphole group, a fluoro group, dibenzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzoborole group, azabenzophosphole group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothiophene group, azabenzoselenophene group, 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, quinazo The alkyl group is selected from the group consisting of a phosphorus group, a phenanthroline group, a pyrrole group, a pyrazole group, an imidazole group, a triazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, an oxadiazole group, a thiadiazole group, a benzopyrazole group, a benzimidazole group, a benzoxazole group, a benzothiazole group, a benzoxadiazole group, a benzothiadiazole group, a 5,6,7,8-tetrahydroisoquinoline group, and a 5,6,7,8-tetrahydroquinoline group.

[0024] According to yet another embodiment, in Formula 1, Ring CY 1is an oxazole group, an isoxazole group, an oxadiazole group, an isoxadiazole group, an oxatriazole group, a thiazole group, an isothiazole group, a thiadiazole group, an isothiadiazole group, a thiatriazole group, a pyrazole group, an imidazole group, a triazole group, a tetrazole group, an azasilole group, a diazasilol group, a triazasilol group, a benzimidazole group, a benzoxazole group, a benzthiazole group, a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a carbazole group, or an azacarbazole group; and / or Ring CY 2 is a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a carbazole group, or an azacarbazole group; and / or Ring CY 3 and CY 5 are each independently a benzene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, or a triazine group, but are not limited to these.

[0025] According to yet another embodiment, the ring CY 4 is a triazole or tetrazole group, but is not limited thereto.

[0026] According to still another embodiment, in Formula 1, Y 43 is N, but is not limited thereto.

[0027] In the above formula 1, T 1 is a single bond, a double bond, *-N(R 6 )-*', *-B(R 6 )-*', *-P(R 6 )-*', *-C(R 6 )(R 7 )-*', *-Si(R 6 )(R 7 )-*', *-Ge(R 6 )(R 7 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2-*', *-C(R 6 )=*', *=C(R 6 )-*', *-C(R 6 )=C(R 7 )-*', *-C(=S)-*', or *-C≡C-*', and T 2 is a single bond, a double bond, *-N(R 8 )-*', *-B(R 8 )-*', *-P(R 8 )-*', *-C(R 8 )(R 9 )-*', *-Si(R 8 )(R 9 )-*', *-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8 )=*', *=C(R 8 )-*', *-C(R 8 )=C(R 9 )-*', *-C(=S)-*', or *-C≡C-*'. R 6 Or R 9 For the explanation of R, please refer to the sections described in this specification. 6 and R 7 means optionally a single bond, a double bond, *-N(R 8c )-*', *-B(R 8c )-*', *-P(R 8c )-*', *-C(R 8c )(R 9c )-*', *-Si(R 8c )(R 9c )-*', *-S-*', *-Se-*', or *-O-*', and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Form a heterocyclic group, R 8 and R 9is, optionally, a single bond, a double bond, *-N(R 8c )-*', *-B(R 8c )-*', *-P(R 8c )-*', *-C(R 8c )(R 9c )-*', *-Si(R 8c )(R 9c )-*', *-S-*', *-Se-*', or *-O-*', and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Form a heterocyclic group. R 8c and R 9c The explanations for each are given in this specification under the heading R 8 and R 9 Please refer to the explanation of "C 5 -C 30 Carbocyclic group" and "C 1 -C 30 The explanation of "heterocyclic group" is as follows: 1 See the explanation for R 10a The explanation for R 1 Please refer to the explanation about.

[0028] According to one embodiment, in Formula 1, T 2 is *-N(R 8 )-*', *-B(R 8 )-*', *-P(R 8 )-*', *-C(R 8 )(R 9 )-*', *-Si(R 8 )(R 9 )-*', *-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8 )=*', *=C(R 8)-*', or *-C(=S)-*', and A 1 Or A 3 is a chemical bond, but is not limited to such.

[0029] R 1 Or R 9 R' and R" are each independently hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 , 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 phosphoric acid group or a salt thereof, a substituted or unsubstituted C 1 -C 60 Alkyl groups, substituted or unsubstituted C 2 -C 60 Alkenyl groups, substituted or unsubstituted C 2 -C 60 Alkynyl group, substituted or unsubstituted C 1 -C 60 Alkoxy groups, substituted or unsubstituted C 3 -C 10 Cycloalkyl groups, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl groups, substituted or unsubstituted C 3 -C 10 Cycloalkenyl group, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl group, substituted or unsubstituted C 6 -C 60 Aryl groups, substituted or unsubstituted C 7 -C 60 Alkylaryl groups, substituted or unsubstituted C 6 -C 60 Aryloxy groups, substituted or unsubstituted C 6 -C 60 Arylthio group, substituted or unsubstituted C 1 -C 60 Heteroaryl groups, substituted or unsubstituted C 2 -C 60alkylheteroaryl groups, substituted or unsubstituted monovalent non-aromatic condensed polycyclic groups, substituted or unsubstituted monovalent non-aromatic condensed heteropolycyclic groups, -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q 7 ), and -P(=O)(Q 8 )(Q 9 ) is selected.

[0030] According to one embodiment, R 1 Or R 9 , R' and R" 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, phosphoric acid group or its salt, -SF 5 , C 1 -C 20 Alkyl groups, and C1-C20 alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phosphoric acid group or its salt, C 1 -C 10 C substituted with at least one of an alkyl group, 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 phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group.1 -C 20 Alkyl group and C 1 -C 20 Alkoxy groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C 1 -C 20 Alkylphenyl 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, benzoyl group, quinolinyl group, quinoxalinyl 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, and imidazopyrimidinyl group; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phosphoric acid group or its salt, C 1 -C 20 Alkyl group, C 1 -C 20Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, phenyl group, biphenyl group, C 1 -C 20 Alkylphenyl 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, 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 phenyl group, a biphenyl group, a C substituted with at least one selected from the group consisting of 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, and an imidazopyrimidinyl group; 1 -C 20Alkylphenyl 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, benzo quinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothiophenyl, isobenzothiazolyl, benzoxazolyl, isobenzoxazolyl, triazolyl, tetrazolyl, oxadiazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, and imidazopyrimidinyl groups; and -N(Q 1 )(Q 2 ), -Si(Q 3 )(Q 4 )(Q 5 ), -B(Q 6 )(Q 7 ), and -P(=O)(Q 8 )(Q 9 ); Q 1 Or Q 9 are each independently -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CH 2 CH 3 , -CH 2 CD 3 , -CH 2 CD 2 H, -CH 2 CDH 2 , -CHDCH 3 , -CHDCD 2 H, -CHDCDH 2 , -CHDCD 3 , -CD 2CH 3 , -CD 2 CD 3 , -CD 2 CD 2 H, and -CD 2 CDH 2 ; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and Deuterium, C 1 -C 10 an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a sec-pentyl group, a tert-pentyl group, a phenyl group, and a naphthyl group, each of which is substituted with at least one selected from the group consisting of an alkyl group and a phenyl group.

[0031] In another embodiment, R 1 Or R 9 R' and R" are each independently hydrogen, deuterium, -F, a cyano group, a nitro group, -SF 5 , -CH 3 , -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , groups represented by the following chemical formulas 9-1 to 9-19, and groups represented by the following chemical formulas 10-1 to 10-227, but are not limited thereto.

[0032] [ka] [ka] TIFF0007630578000009.tif173141TIFF0007630578000010.tif189141TIFF0007630578000011.tif214140TIFF0007630578000012.tif173140

[0033] In the above Chemical Formulae 9-1 to 9-19 and Chemical Formulae 10-1 to 10-227, * is a bonding site with an adjacent atom, Ph is a phenyl group, and TMS is a trimethylsilyl group.

[0034] In the above formula 1, a1 to a3 and a5 are each R 1 Or R 3 , and R 5 a5 represents the number of R 4 and is selected from integers of 0 to 2. When a1 is 2 or more, R 1 are the same or different, and when a2 is 2 or more, R 2 are the same or different, and when a3 is 2 or more, R 3 are the same or different, and when a4 is 2 or more, 2 or more R 4 are the same or different, and when a5 is 2 or more, R 5 are either the same or different.

[0035] In the above formula 1, i) Multiple adjacent R 1 Two of the R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 Forming a heterocyclic group, ii) Multiple adjacent R2 Two of the R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 forming a heterocyclic group, iii) Multiple adjacent R 3 Two of the R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 forming a heterocyclic group, iv) Multiple adjacent R 4 Two of the R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 forming a heterocyclic group, v) Multiple adjacent R 5 Two of the R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30 forming a heterocyclic group, vi) R 1 Or R 9 Two of R' and R" are optionally bonded to each other, and at least one R 10a Substituted or unsubstituted C 5 -C 30 A carbocyclic group or at least one R 10a Substituted or unsubstituted C 1 -C 30Form a heterocyclic group. 5 -C 30 Carbocyclic group" and "C 1 -C 30 The explanation of "heterocyclic group" is as follows: 1 See the explanation for R 10a The explanation for R 1 Please refer to the explanation about.

[0036] * and *' are bonding sites with adjacent atoms.

[0037] According to one embodiment, the organometallic compound represented by Formula 1 is a) One of the following conditions is satisfied: b) One of the following conditions 4 and 5 is satisfied, or c) One of the following <Condition 1>, <Condition 2>, and <Condition 3> is satisfied, and one of the following <Condition 4> and <Condition 5> is satisfied.

[0038] <Condition 1>

[0039] A 1 and A 2 is a chemical bond, The moiety represented by TIFF0007630578000013.tif34128 is represented by the following chemical formula A1-1: T 1 is *-N(R 6 )-*', *-B(R 6 )-*', *-P(R 6 )-*', *-C(R 6 )(R 7 )-*', *-Si(R 6 )(R 7 )-*', *-Ge(R 6 )(R 7 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 6)=*', *=C(R 6 )-*', *-C(R 6 )=C(R 7 )-*', *-C(=S)-*', or *-C≡C-*', The moiety represented by TIFF0007630578000014.tif33128 is represented by the following chemical formula A2-1;

[0040] <Condition 2>

[0041] A 1 and A 2 is a chemical bond, The moiety represented by the formula A1-2 is represented by the following formula: T 1 is a single bond, The moiety represented by TIFF0007630578000015.tif34128TIFF0007630578000016.tif33128 is represented by the following chemical formula A2-1;

[0042] <Condition 3>

[0043] A 1 and A 2 is a chemical bond, The moiety represented by TIFF0007630578000017.tif34128 is represented by the following chemical formula A1-1: T 1 is a single bond, The moiety represented by TIFF0007630578000018.tif33128 is represented by the following chemical formula A2-3;

[0044] <Condition 4>

[0045] A 2 and A 3 is a chemical bond, The moiety represented by TIFF0007630578000019.tif33128 is represented by the following chemical formula A2-1: T 2 is *-N(R 8)-*', *-B(R 8 )-*', *-P(R 8 )-*', *-C(R 8 )(R 9 )-*', *-Si(R 8 )(R 9 )-*', *-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8 )=*', *=C(R 8 )-*', *-C(R 8 )=C(R 9 )-*', *-C(=S)-*', or *-C≡C-*';

[0046] <Condition 5>

[0047] A 2 and A 3 is a chemical bond, The moiety represented by TIFF0007630578000020.tif33128 is represented by the following chemical formula A2-2: T 2 is a single bind:

[0048] [ka]

[0049] In the above chemical formulas A1-1, A1-2, A2-1, A2-2, and A2-3, X 1 , X 2 , Tamaki CY 1 , Tamaki CY 2 , R 1 , R 2 For the explanation of a1, a2, please refer to the respective parts described in this specification. 1 Or Y 4 are each independently C or N; X 1 and Y 1 Bond with and X 1 and Y 2Bond with Y 1 and Y 2 Bond with X 2 and Y 4 Bond with X 2 and Y 3 and Y 3 and Y 4 and the bonds to are, independently of each other, single or double bonds; In the above chemical formulas A1-1 and A1-2, * represents chemical formula 1, A 1 or a bonding site with M, and *' is T in Chemical Formula 1. 1 It is a binding site for In the above chemical formulas A2-1, A2-2 and A2-3, * represents chemical formula 1, A 2 or a bonding site with M, and *' is T in Chemical Formula 1. 1 The *" is the bond site of T in Chemical Formula 1. 2 It is the binding site for

[0050] The organometallic compound represented by the above chemical formula 1 is a) Either <Condition 1>, <Condition 2>, or <Condition 3> is satisfied, b) Either <Condition 4> or <Condition 5> is satisfied, or c) One of <Condition 1>, <Condition 2>, and <Condition 3> is satisfied, and one of the following <Condition 4> and <Condition 5> is satisfied, whereby M in Chemical Formula 1, ring CY 1 and CY 2 and / or M, ring CY of formula 1. 2 and CY 3 The cyclometalated ring formed by X becomes a six-membered ring. 1 -MX 2 The corners between and / or X 2 -MX 3Since the angle between the two metals forms a metal complex structure in which steric hindrance is minimized and the structure of the material is maintained, the organometallic compound represented by Formula 1 has excellent structural stability, and thus electronic devices, such as organic light emitting devices, including the organometallic compound represented by Formula 1 have a long life.

[0051] According to another embodiment, in Formula 1, The moiety represented by TIFF0007630578000022.tif34128 is represented by one of the following chemical formulae A1-1(1) to A1-1(54) and A1-2(1) to A1-2(74).

[0052] [ka] TIFF0007630578000024.tif125144 [ka] TIFF0007630578000026.tif178146TIFF0007630578000027.tif218142

[0053] In the above chemical formulae A1-1(1) to A1-1(54) and A1-2(1) to A1-2(74), X 1 and R 1 The explanations for are the same as those described in this specification, X 11 is O, S, N(R 11 ), C(R 11 )(R 12 ), or Si(R 11 )(R 12 ) and X 13 is N or C(R 13 ) and X 14 is N or C(R 14 ) and R 11 Or R 18The explanations for each are given in this specification under the heading R 1 Please refer to the explanation of a17 is selected from integers of 0 to 7; a16 is selected from integers of 0 to 6; a15 is selected from the group consisting of integers of 0 to 5; a14 is selected from integers of 0 to 4; a13 is selected from integers of 0 to 3; a12 is selected from integers of 0 to 2; * is chemical formula 1, A 1 or a binding site for M, *' is chemical formula 1, T 1 It is the binding site for

[0054] According to yet another embodiment, in Formula 1, The moiety represented by TIFF0007630578000028.tif33128 is represented by one of the following chemical formulae A2-1(1) to A2-1(17), A2-2(1) to A2-2(58), and A2-3(1) to A2-3(62).

[0055] [ka] [ka] TIFF0007630578000031.tif172145TIFF0007630578000032.tif81142 [ka] TIFF0007630578000034.tif193148

[0056] In the above chemical formulas A2-1(1) to A2-1(17), chemical formulas A2-2(1) to A2-2(58), and chemical formulas A2-3(1) to A2-3(62), X 2 and R 2The explanations for are the same as those described in this specification, X 21 is O, S, N(R 21 ), C(R 21 )(R 22 ), or Si(R 21 )(R 22 ) and X 23 is N or C(R 23 ) and X 24 is N or C(R 24 ) and R 21 Or R 28 The explanations for each are given in this specification under the heading R 2 Please refer to the explanation of a26 is selected from integers of 0 to 6; a25 is selected from integers of 0 to 5; a24 is selected from integers of 0 to 4; a23 is selected from integers of 0 to 3; a22 is selected from integers of 0 to 2; * is chemical formula 1, A 2 or a binding site for M, *' is chemical formula 1, T 1 It is a binding site for *" is chemical formula 1, T 2 It is the binding site for

[0057] According to yet another embodiment, in Formula 1, The moiety represented by TIFF0007630578000035.tif35128 is represented by one of the following chemical formulas A3-1(1) to A3-1(12).

[0058] [ka]

[0059] In the above chemical formulas A3-1(1) to A3-1(12), X 3and R 3 The explanations for are the same as those described in this specification, X 31 is O, S, N(R 31 ), C(R 31 )(R 32 ), or Si(R 31 )(R 32 ) and R 31 Or R 38 The explanations for each are given in this specification under the heading R 3 Please refer to the explanation of a34 is selected from integers of 0 to 4; a33 is selected from integers of 0 to 3; a32 is selected from integers from 0 to 2, * is chemical formula 1, A 3 or a binding site for M, *" is chemical formula 1, T 2 It is a binding site for *' is chemical formula 1, Y 41 It is a binding site for TIFF0007630578000037.tif10128 is a compound represented by the chemical formula 1, which has the ring CY 5 It is the binding site for

[0060] According to yet another embodiment, in Formula 1, The moiety represented by TIFF0007630578000038.tif27128 is represented by one of the following chemical formulas A4-1(1) to A4-1(12).

[0061] [ka]

[0062] In the above chemical formulas A4-1(1) to A4-1(12), X 4 and R 4 The explanations for are the same as those described in this specification, * is a binding site with M in Chemical Formula 1; *' is the ring CY in chemical formula 1. 3 It is a binding site for *" is the ring CY in chemical formula 1. 5 It is the binding site for

[0063] According to yet another embodiment, in Formula 1, The moiety represented by TIFF0007630578000040.tif23128 is selected from among the following chemical formulas A5-1(1) to A5-1(8).

[0064] [ka]

[0065] In the above chemical formulas A5-1(1) to A5-1(8), R 5 The explanation for is the same as that described in this specification, a55 is selected from an integer from 0 to 5; a54 is selected from integers from 0 to 4; a53 is selected from integers from 0 to 3; TIFF0007630578000042.tif10128 is a compound represented by the chemical formula 1, which has the ring CY 3 It is a binding site for *" is chemical formula 1, Y 42 It is the binding site for

[0066] According to yet another embodiment, in Formula 1, The moiety represented by TIFF0007630578000043.tif34128 is (is) represented by one of the following chemical formulas CY1-1 to CY1-59, The moiety represented by TIFF0007630578000044.tif33128 is (is) represented by one of the following chemical formulas CY2-1 to CY2-34, The moiety represented by TIFF0007630578000045.tif49128 is represented by one of the following chemical formulas CY3-1 to CY3-6.

[0067] [ka] TIFF0007630578000047.tif220149 [ka] [ka]

[0068] In the above chemical formulas CY1-1 to CY1-59, CY2-1 to CY2-34, and CY3-1 to CY3-6, A 3 , X 1 Or X 3 , and R 1 Or R 4 For the explanation of each of the above, please refer to the respective sections described in this specification. X 11 is O, S, N(R 11 ), C(R 11 )(R 12 ), or Si(R 11 )(R 12 ) and R 1a Or R 1d , R 11 and R 12 For explanations of each, see R 1 Please refer to the explanation of R 2a Or R 2c For explanations of each, see R 2 Please refer to the explanation of Z 31 is N or C(R 31 ), and Z 32 is N or C(R 32 ) and R 31 and R 32 For explanations of each, see R 3 Please refer to the explanation of Z 51 is N or C(R 51 ), and Z52 is N or C(R 52 ), and Z 53 is N or C(R 53 ), and Z 54 is N or C(R 54 ) and R 51 Or R 54 For explanations of each, see R 5 Please refer to the explanation of However, R 1 , R 2 , R 1a Or R 1d , and R 2a Or R 2c is not hydrogen, In the above chemical formulas CY1-1 to CY1-59, * represents chemical formula 1, A 1 or a bonding site with M, and *' is T in Chemical Formula 1. 1 It is a binding site for In the above chemical formulas CY2-1 to CY2-34, * represents chemical formula 1, A 2 or a bonding site with M, and *' is T in Chemical Formula 1. 1 The *" is the bond site of T in Chemical Formula 1. 2 It is a binding site for In the above chemical formulas CY3-1 to CY3-6, the two * are binding sites with M in chemical formula 1, and *" is T in chemical formula 1. 2 It is the binding site for

[0069] According to yet another embodiment, the organometallic compound is represented by the following formula 1-1 or 1-2:

[0070] [ka] [ka]

[0071] In the above chemical formulas 1-1 and 1-2, M, X 1 Or X 4 , Y 41Or Y 44 , A 3 , Tamaki CY 1 Or CY 5 , Tamaki CY 5a , R 1 Or R 5 For the explanation of a1 to a5, please refer to the respective parts described in this specification. T 2 is *-N(R 8 )-*', *-B(R 8 )-*', *-P(R 8 )-*', *-C(R 8 )(R 9 )-*', *-Si(R 8 )(R 9 )-*', *-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8 )=*', *=C(R 8 )-*', or *-C(=S)-*', and R 8 and R 9 For the explanation of each of the above, please refer to the respective sections described in this specification. Y 2 Or Y 4 are each independently C or N; X 2 and Y 3 Bond with X 2 and Y 4 Bonds with and X 1 and Y 2 and the bonds to are, independently of each other, single or double bonds; Z 11 is N or C(R 11 ), and Z 12 is N or C(R 12 ), and Z 13 is N or C(R 13 ), and Z 14 is N or C(R 14 ), and Z 15 is N or C(R 15 ), and Z 16 is N or C(R16 ), and Z 17 is N or C(R 17 ), and Z 21 is N or C(R 21 ), and Z 22 is N or C(R 22 ), and Z 23 is N or C(R 23 ), and Z 24 is N or C(R 24 ), and Z 25 is N or C(R 25 ), and Z 26 is N or C(R 26 ) and R 11 Or R 17 The explanations for each are given in this specification under the heading R 1 Please refer to the explanation of R 21 Or R 26 The explanations for each are given in this specification under the heading R 2 Please refer to the explanation about.

[0072] According to yet another embodiment, the organometallic compound is represented by the following formula 1-1(1) or 1-2(1):

[0073] [ka] [ka]

[0074] In the above chemical formulas 1-1(1) and 1-2(1), M, X 1 Or X 4 , Y 41 Or Y 44 , A 3 , Tamaki CY 3 Or CY 5 , Tamaki CY 5a , R 3 Or R 5 For the explanation of a3 to a5, please refer to the respective parts described in this specification. T 2 is *-N(R 8 )-*', *-B(R 8 )-*', *-P(R 8 )-*', *-C(R 8 )(R 9 )-*', *-Si(R 8 )(R 9 )-*', *-Ge(R 8 )(R 9 )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 8 )=*', *=C(R 8 )-*', or *-C(=S)-*', and R 8 and R 9 For the explanation of each of the above, please refer to the respective sections described in this specification. Z 11 is N or C(R 11 ), and Z 12 is N or C(R 12 ), and Z 13 is N or C(R 13 ), and Z 14 is N or C(R 14 ), and Z 15 is N or C(R 15 ), and Z 16 is N or C(R 16 ), and Z 17 is N or C(R 17 ), and Z 21 is N or C(R 21 ), and Z 22 is N or C(R 22 ), and Z 23 is N or C(R 23 ), and Z 24 is N or C(R 24 ), and Z 25 is N or C(R 25 ), and Z 26 is N or C(R 26 ) and R 11 Or R 17 The explanations for each are given in this specification under the heading R1 Please refer to the explanation of R 21 Or R 26 The explanations for each are given in this specification under the heading R 2 Please refer to the explanation of A 11 is *-N(R 8a )-*', *-B(R 8a )-*', *-P(R 8a )-*', *-C(R 8a )(R 9a )-*', *-Si(R 8a )(R 9a )-*', *-Ge(R 8a )(R 9a )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8a )=*', *=C(R 8a )-*', *-C(R 8a )=C(R 9a )-*', *-C(=S)-*', or *-C≡C-*', and R 8a and R 9a The explanations for each are given in this specification under the heading R 8 and R 9 Please refer to the section stated in.

[0075] According to yet another embodiment, the organometallic compound is represented by Formula 1A:

[0076] [ka]

[0077] In the above formula 1A, M, X 1 Or X 4 , Y 41 Or Y 44 , A 1 Or A 3 , Tamaki CY 1 Or CY 5 , Tamaki CY 5a , T 2, R 1 Or R 5 For the explanation of a1 to a5, please refer to the respective parts described in this specification. T 3 is C, Si, or Ge, Ring CY 6 and C.Y. 7 The explanation of each of the rings CY 1 Please refer to the explanation of R 6a , R 6b , R 7a , and R 7b The explanations for each are given in this specification under the heading R 1 Please refer to the explanation of A 12 is a single bond, *-N(R 8b )-*', *-B(R 8b )-*', *-P(R 8b )-*', *-C(R 8b )(R 9b )-*', *-Si(R 8b )(R 9b )-*', *-Ge(R 8b )(R 9b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O) 2 -*', *-C(R 8b )=*', *=C(R 8b )-*', *-C(R 8b )=C(R 9b )-*', *-C(=S)-*', or *-C≡C-*', and R 8b and R 9b The explanations for each are given in this specification under the heading R 8 and R 9 Please refer to the section stated in.

[0078] 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, and azadibenzothiophene 5,5-dioxide group" respectively mean or "an indole group, a benzoborole group, a benzophosphole group, an indene group, a benzosilole 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, or a dibenzothiophene-5,5-dioxide group," but at least one of the carbons forming the ring is replaced with a nitrogen atom.

[0079] According to other embodiments, the organometallic compound is one of compounds 1 to 196 below.

[0080] [ka] TIFF0007630578000056.tif199148TIFF0007630578000057.tif197149TIFF0007630578000058.tif198148TIFF00076305780 00059.tif199147TIFF0007630578000060.tif187145TIFF0007630578000061.tif193149TIFF0007630578000062.tif233151

[0081] In a solution (e.g., toluene) of the organometallic compound, the peak of the emission spectrum has a maximum emission wavelength in the range of 420 nm to 500 nm, for example, in the range of 440 nm to 470 nm (another example, in the range of 455 nm to 465 nm), and a full width at half maximum (FWHM) in the range of 30 nm to 80 nm, for example, in the range of 30 nm to 60 nm (another example, in the range of 30 nm to 45 nm).Therefore, the organometallic compound can emit blue light with excellent color purity.

[0082] In the above formula 1, the ring CY 4 X 4 , Y 41 , Y 42 , Y 43 , and Y 44 And "three" or more is N. For example, the ring CY 4 is a triazole group or a tetrazole group, but is not limited thereto. As a result, the organometallic compound represented by Chemical Formula 1 has a minimized molecular structure shift in an excited state, and emits light having a peak with a relatively narrow half-width ratio, thereby minimizing non-radiative decay and having a high luminescence quantum efficiency (PLQY). In addition, the organometallic compound represented by Chemical Formula 1 has a relatively high T 1 Energy levels (e.g., T in the range of 2.69 eV to 2.80 eV) 1 Therefore, an electronic device using the organometallic compound represented by Chemical Formula 1, for example, an organic light-emitting device, can effectively emit light having high luminous efficiency and high color purity (for example, deep blue light).

[0083] Meanwhile, the above formula 1 is a ring CY as defined herein. 5a It has the ring CY 5a is a ring CY 3 Or CY 5 is a ring formed by connecting each of the rings, and the ring CY 5aBy virtue of this, the organometallic compound represented by Chemical Formula 1 has a robust molecular structure that is stable against various charges and heat. As a result, electronic devices using the organometallic compound represented by Chemical Formula 1, such as organic light-emitting devices, have a long life.

[0084] Further, in the above formula 1, M is beryllium (Be), magnesium (Mg), aluminum (Al), calcium (Ca), titanium (Ti), manganese (Mn), cobalt (Co), copper (Cu), zinc (Zn), gallium (Ga), germanium (Ge), zirconium (Zr), ruthenium (Ru), rhodium (Rh), palladium (Pd), silver (Ag), rhenium (Re), platinum (Pt), or gold (Au) (e.g., Pt, Pd, or Au), and the organometallic compound of the above formula 1 has a tetradentate ligand. As a result, the organometallic compound represented by the above formula 1 has a square-planar coordination structure and a high radiative decay rate, so that an electronic device using the organometallic compound, for example, an organic light emitting device, can effectively emit blue light with high luminous efficiency and high color purity.

[0085] For example, the HOMO (highest occupied molecular orbital), LUMO (lowest unoccupied molecular orbital), and T 1 The energy levels of were evaluated using the DFT method of the Gaussian program (structure optimization at B3LYP, 6-31G(d,p) level), and the results are shown in Table 1 below.

[0086] [Table 1]

[0087] [ka]

[0088] In Table 1, the organometallic compound represented by the formula 1 has a higher T 1 Since it has been confirmed that the organometallic compound represented by Formula 1 has the above-mentioned energy levels, it has suitable electrical properties for use as a dopant in electronic devices, such as organic light emitting devices.

[0089] A method for synthesizing the organometallic compound represented by the above Chemical Formula 1 can be recognized by those skilled in the art by referring to the synthesis examples described below.

[0090] Therefore, the organometallic compound represented by Chemical Formula 1 is suitable for use as a dopant in an organic layer of an organic light-emitting device, for example, in an organic layer, an emitting layer. According to another aspect, there is provided an organic light-emitting device having a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode, including an emitting layer, and including at least one organometallic compound represented by Chemical Formula 1.

[0091] The organic light emitting device has an organic layer including an organometallic compound represented by Chemical Formula 1 as described above, and thus has low driving voltage, high efficiency, high power, high quantum efficiency, long life and / or low roll-off ratio, and excellent color purity.

[0092] The organometallic compound represented by Chemical Formula 1 is used between a pair of electrodes of an organic light emitting device. For example, the organometallic compound represented by Chemical Formula 1 is included in an emission layer. In this case, the organometallic compound acts as a dopant, and the emission layer further includes a host (i.e., the content of the organometallic compound represented by Chemical Formula 1 is less than the content of the host).

[0093] According to an embodiment, light emitted from an emission layer of an organic light emitting device including an organometallic compound in the emission layer is blue light, and the CIE y coordinate of the blue light is in the range of 0.10 to 0.340, for example, 0.120 to 0.280, thereby realizing a high-quality organic light emitting device that emits blue light.

[0094] In this specification, "(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."

[0095] For example, the organic layer contains only the compound 1 as an organometallic compound. In this case, the compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer contains the compound 1 and the compound 2 as organometallic compounds. In this case, the compounds 1 and 2 are present in the same layer (for example, the compounds 1 and 2 are both present in the light-emitting layer).

[0096] The first electrode is an anode that is a hole-injection electrode and the second electrode is a cathode that is an electron-injection electrode, or the first electrode is a cathode that is an electron-injection electrode and the second electrode is an anode that is a hole-injection electrode.

[0097] 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 interposed between the first electrode and the light-emitting layer, and an electron transport region interposed between the light-emitting layer and the second electrode, the hole transport region including a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region including a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0098] In this specification, the term "organic layer" refers to a single layer and / or multiple layers interposed 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.

[0099] Fig. 1 is a schematic cross-sectional view of an organic light emitting device 10 according to an embodiment. Hereinafter, the structure and manufacturing method of an organic light emitting device according to an embodiment of the present invention will be described with reference to Fig. 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.

[0100] A substrate is additionally disposed below the first electrode 11 or above the second electrode 19. As the substrate, a substrate used in general organic light-emitting devices is used, and a glass substrate or a transparent plastic substrate that is excellent in mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and waterproofness is used.

[0101] The first electrode 11 is formed by providing 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 is selected from materials having a high work function so that holes can be easily injected. The first electrode 11 is a reflective electrode, a semi-transparent electrode, or a transparent electrode. The first electrode material may be indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO 2 ), zinc oxide (ZnO), etc., are used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), magnesium-silver (Mg-Ag), etc. are used.

[0102] The first electrode 11 has a single layer structure or a multi-layer structure including two or more layers, for example, the first electrode 11 has a three-layer structure of ITO / Ag / ITO, but is not limited thereto.

[0103] On top of the first electrode 11, an organic layer 15 is disposed.

[0104] The organic layer 15 includes a hole transport region, an emission layer, and an electron transport region.

[0105] The hole transport region is disposed between the first electrode 11 and the light emitting layer.

[0106] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0107] The hole transport region includes only a hole injection layer or only a hole transport layer, or has 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.

[0108] When the hole transport region includes a hole injection layer, the hole injection layer (HIL) is formed on the first electrode 11 using various methods such as vacuum deposition, spin coating, casting, and Langmuir-Blodgett (LB) method.

[0109] When the hole injection layer is formed by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the structure of the hole injection layer, and the thermal properties. For example, the deposition temperature is about 100 to about 500° C., the vacuum degree is about 10 -8 ~about 10 -3 The pressure, pressure and deposition rate are selected from the ranges of about 0.01 to about 100 Å / sec, but are not limited thereto.

[0110] When the hole injection layer is formed by a spin coating method, the coating conditions vary depending on the compound used as the hole injection layer material, the desired structure of the hole injection layer, and the thermal properties. The coating speed is about 2,000 rpm to about 5,000 rpm, and the heat treatment temperature for removing the solvent after coating is selected in the range of about 80°C to 200°C, but is not limited thereto.

[0111] The conditions for forming the hole transport layer and the electron blocking layer are the same as those for forming the hole injection layer.

[0112] The hole transport region includes at least one of, 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, and a compound represented by the following chemical formula 202.

[0113] [ka]

[0114] [ka] [ka]

[0115] In the above formula 201, Ar 101 and Ar 102 are independent of each other, phenylene groups, pentalenylene groups, indenylene groups, naphthylene groups, azulenylene groups, heptalenylene groups, acenaphthylene groups, fluorenylene groups, phenalenylene groups, phenanthrenylene groups, anthracenylene groups, fluoranthenylene groups, triphenylenylene groups, pyrenylene groups, chrysenylenylene groups, naphthacenylene groups, picenylene groups, perylenylene groups, and pentacenylene groups; and 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, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2-C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkyl groups, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 and selected from the group consisting of 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, and a pentacenylene group, each of which is substituted with at least one of a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, and a monovalent non-aromatic hetero-condensed polycyclic group.

[0116] In the above 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.

[0117] In the above chemical formulas 201 and 202, R 101 Or R 108 , R 111 Or R 119 , and R 121 Or 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, phosphoric acid group or its salt, C 1 -C 10 Alkyl groups (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.) and C 1 -C 10 Alkoxy groups (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.); C substituted with one or more of 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, and a phosphate group or a salt thereof. 1 -C 10 Alkyl group and C 1 -C 10 Alkoxy groups; Phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl groups; and 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, phosphoric acid group or its salt, C 1 -C 10 Alkyl groups, and C 1 -C 10 and aryl groups selected from the group consisting of, but not limited to, phenyl, naphthyl, anthracenyl, fluorenyl, and pyrenyl groups substituted with one or more of alkoxy groups.

[0118] In the above formula 201, R 109 teeth, Phenyl, naphthyl, anthracenyl, and pyridinyl groups; and 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, phosphoric acid group or its salt, C 1 -C20 Alkyl group, C 1 -C 20 phenyl, naphthyl, anthracenyl, and pyridinyl groups substituted with one or more of alkoxy, phenyl, naphthyl, anthracenyl, and pyridinyl groups.

[0119] According to an embodiment, the compound represented by Formula 201 is represented by, but is not limited to, Formula 201A below.

[0120] [ka]

[0121] In the above formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed description, see above.

[0122] For example, the compound represented by the above chemical formula 201 and the compound represented by the above chemical formula 202 include, but are not limited to, the following compounds HT1 to HT20.

[0123] [ka] TIFF0007630578000070.tif198153

[0124] 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 at least one layer of a hole injection layer and a hole transport layer, 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.

[0125] The hole transport region may further comprise a charge generating material to enhance electrical conductivity in addition to the materials described above. The charge generating material may be dispersed uniformly or non-uniformly within the hole transport region.

[0126] The charge generating material may be, for example, a p-dopant. The p-dopant may be one of, but is not limited to, quinone derivatives, metal oxides, and cyano group-containing compounds. For example, non-limiting examples of p-dopants include, but are not limited to, quinone derivatives such as tetracyanoquinone dimethane (TCNQ) and 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide and molybdenum oxide; and cyano group-containing compounds such as the following compound HT-D1.

[0127] [ka]

[0128] The hole transport region further comprises a buffer layer.

[0129] The buffer layer compensates for the optical resonance distance according to the wavelength of light emitted from the light emitting layer, thereby increasing efficiency.

[0130] An emitting layer (EML) is formed on the hole transport region using a method such as vacuum deposition, spin coating, casting, LB method, etc. When forming an emitting layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, but are generally selected from the same range of conditions as those for forming the hole injection layer.

[0131] On the other hand, when the hole transport region includes an electron blocking layer, the material of the electron blocking layer is selected from the materials used in the hole transport region as described above and the host materials described below, but is not limited thereto. For example, when the hole transport region includes an electron blocking layer, mCP described below is used as the material of the electron blocking layer.

[0132] The light-emitting layer includes a host and a dopant, and the dopant includes the organometallic compound represented by Chemical Formula 1 above.

[0133] The host includes at least one of TPBi, TBADN, ADN (also referred to as "DNA"), CBP, CDBP, TCP, Mcp, compound H50, compound H51, and compound 52 below.

[0134] [ka]

[0135] Alternatively, the host further comprises a compound represented by the following formula 301:

[0136] [ka]

[0137] In the above formula 301, Ar 111 and Ar 112 are independent of each other, Phenylene, naphthylene, phenanthrenylene, and pyrenylene groups; and phenylene groups, naphthylene groups, phenanthrenylene groups, and pyrenylene groups substituted with one or more of phenyl groups, naphthyl groups, and anthracenyl groups.

[0138] In the above formula 301, Ar 113 Or Ar 116 are each independently C 1 -C 10Alkyl groups, phenyl groups, naphthyl groups, phenanthrenyl groups, and pyrenyl groups; and a phenyl group, a naphthyl group, a phenanthrenyl group, and a pyrenyl group substituted with one or more of a phenyl group, a naphthyl group, and an anthracenyl group.

[0139] In the above formula 301, g, h, i, and j are each independently an integer of 0 to 4, for example, 0, 1, or 2.

[0140] In the above formula 301, Ar 113 Or Ar 116 are each independently C substituted with one or more of phenyl, naphthyl, and anthracenyl groups 1 -C 10 Alkyl groups; Phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl groups; 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, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl groups substituted with one or more of alkoxy, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, and fluorenyl groups; and TIFF0007630578000074.tif26128, but is not limited thereto.

[0141] Alternatively, the host includes a compound represented by formula 302:

[0142] [ka]

[0143] In the above formula 302, Ar 122 Or Ar 125 For a detailed description, see the above formula 301, Ar 113 Please refer to the explanation about.

[0144] In the above formula 302, Ar 126 and Ar 127 are independent of each other, C 1 -C 10 It is an alkyl group (for example, a methyl group, an ethyl group, or a propyl group).

[0145] In the above formula 302, k and l are each independently an integer from 0 to 4. For example, k and l are 0, 1, or 2.

[0146] When the organic light emitting device is a full-color organic light emitting device, the light emitting layer is patterned into a red light emitting layer, a green light emitting layer, and a blue light emitting layer, or the light emitting layer may have a structure in which a red light emitting layer, a green light emitting layer, and / or a blue light emitting layer are stacked to emit white light.

[0147] When the light emitting layer includes a host and a dopant, the content of the dopant is generally selected in 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.

[0148] 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.

[0149] An electron transport region is then placed on top of the light emitting layer.

[0150] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0151] For example, the electron transport region may have a structure of, but is not limited to, hole blocking layer / electron transport layer / electron injection layer, or electron transport layer / electron injection layer. The electron transport layer may have a single layer structure or a multilayer structure including two or more different materials.

[0152] The conditions for forming the hole blocking layer, the electron transport layer, and the electron injection layer in the electron transport region refer to the conditions for forming the hole injection layer.

[0153] When the electron transport region includes a hole blocking layer, the hole blocking layer may include, but is not limited to, at least one of the following: BCP, Bphen, and BAlq.

[0154] [ka]

[0155] The thickness of the hole blocking layer is about 20 Å to about 1,000 Å, for example, about 30 Å to about 300 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.

[0156] The electron transport layer further comprises at least one of BCP, Bphen, described above, and Alq3, Balq, TAZ, and NTAZ, described below.

[0157] [ka]

[0158] Alternatively, the electron transport layer includes at least one of the following compounds ET1 to ET25, but is not limited thereto.

[0159] [ka] TIFF0007630578000079.tif188147

[0160] 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-mentioned range, satisfactory electron transport properties can be obtained without a substantial increase in driving voltage.

[0161] The electron transport layer further comprises a metal-containing material in addition to the materials described above.

[0162] The metal-containing material includes a Li complex, for example the following compound ET-D1 (lithium 8-hydroxyquinolate (LiQ)) or ET-D2.

[0163] [ka]

[0164] The electron transport region also includes an electron injection layer (EIL) that facilitates electron injection from second electrode 19 .

[0165] The electron injection layer is LiF, NaCl, CsF, Li 2 At least one selected from the group consisting of O and BaO.

[0166] 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-mentioned range, satisfactory electron injection characteristics can be obtained without a substantial increase in driving voltage.

[0167] A second electrode 19 is provided on the organic layer 15. The second electrode 19 is a cathode. A metal, an alloy, an electrically conductive compound, or a combination thereof having a relatively low work function is used as the material for the second electrode 19. Specific examples of the material for 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 front light emitting element.

[0168] Although the organic light-emitting device has been described above with reference to FIG. 1, the present invention is not limited thereto.

[0169] In yet another aspect, there is provided a diagnostic composition comprising one or more organometallic compounds represented by Formula 1 above.

[0170] 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.

[0171] The diagnostic composition is used in a variety of applications, such as various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0172] In this specification, C 1 -C 60 The alkyl group means a linear or branched saturated aliphatic hydrocarbon monovalent group having 1 to 60 carbon atoms, and specific examples include a methyl group, an ethyl group, a propyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group. 1 -C 60 The alkylene group is C 1 -C 60 It means a divalent group having the same structure as an alkyl group.

[0173] In this specification, C1 -C 60 The alkoxy group is -OA. 101 (Here, A 101 is C 1 -C 60 Specific examples of the aryl group include methoxy, ethoxy, and isopropyloxy groups.

[0174] In this specification, C 2 -C 60 The alkenyl group is C 2 -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 an ethenyl group, a propenyl group, and a butenyl group. 2 -C 60 The alkenylene group is C 2 -C 60 It means a divalent group having the same structure as an alkenyl group.

[0175] In this specification, C 2 -C 60 The alkynyl group is C 2 -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. 2 -C 60 The alkynylene group is C 2 -C 60 It means a divalent group having the same structure as an alkynyl group.

[0176] In this specification, C 3 -C 10 The cycloalkyl group means a monovalent saturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, and specific examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group. 3 -C 10 The cycloalkylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkyl group.

[0177] In this specification, C 1 -C 10 The heterocycloalkyl group means a monovalent monocyclic group having 1 to 10 carbon atoms containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and specific examples thereof include a tetrahydrofuranyl group, a tetrahydrothiophenyl group, and the like. 1 -C 10 The heterocycloalkylene group is 1 -C 10 It means a divalent group having the same structure as a heterocycloalkyl group.

[0178] In this specification, C 3 -C 10 The cycloalkenyl group means a monovalent monocyclic group having 3 to 10 carbon atoms, which has at least one carbon-carbon double bond in the ring but does not have aromaticity. Specific examples thereof include a cyclopentenyl group, a cyclohexenyl group, and a cycloheptenyl group. 3 -C 10 The cycloalkenylene group is C 3 -C 10 It means a divalent group having the same structure as a cycloalkenyl group.

[0179] In this specification, C 1 -C 10 The heterocycloalkenyl group is a monovalent monocyclic group having 1 to 10 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and has at least one double bond in the ring. 1 -C 10 Specific examples of heterocycloalkenyl groups include 2,3-dihydrofuranyl groups, 2,3-dihydrothiophenyl groups, and the like. 1 -C 10 The heterocycloalkenylene group is C 1 -C 10 It means a divalent group having the same structure as a heterocycloalkenyl group.

[0180] In this specification, C 6 -C 60 An aryl group means a monovalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms, C 6 -C 60 The arylene group refers to a divalent group having a carbocyclic aromatic system having 6 to 60 carbon atoms. 6 -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. 6 -C 60 Aryl groups and C 6 -C 60 When the arylene group contains more than one ring, the two or more rings are each fused.

[0181] In this specification, C 1 -C 60 The heteroaryl group means a monovalent group having a cyclic aromatic system having 1 to 60 carbon atoms and containing at least one heteroatom selected from N, O, P, Si, and S as a ring-forming atom, and C 1 -C 60 The heteroarylene group refers to a divalent group having a carbocyclic aromatic system having 1 to 60 carbon atoms and containing at least one heteroatom selected from N, O, P, and S as a ring-forming atom. 1 -C 60 Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, and isoquinolinyl groups. 1 -C 60 Heteroaryl groups and C 1 -C 60 When a heteroarylene group contains more than one ring, the two or more rings are each fused.

[0182] In this specification, C 6 -C 60 The aryloxy group is -OA. 102 (Here, A 102 is C 6 -C 60aryl group), C 6 -C 60 The arylthio group is -SA 103 (Here, A 103 is C 6 -C 60 aryl group).

[0183] In the present specification, the monovalent non-aromatic condensed polycyclic group refers to a monovalent group (e.g., having 8 to 60 carbon atoms) in which two or more rings are condensed, each of which contains only carbon as a ring-forming atom, and the entire molecule has non-aromaticity. Specific examples of the monovalent non-aromatic condensed polycyclic group include a fluorenyl group. In the present specification, the divalent non-aromatic condensed polycyclic group refers to a divalent group having the same structure as the monovalent non-aromatic condensed polycyclic group.

[0184] In this specification, the monovalent non-aromatic hetero-condensed polycyclic group means a monovalent group (e.g., having 1 to 60 carbon atoms) in which two or more rings are condensed and the ring-forming atoms include heteroatoms selected from N, O, P, Si, and S, in addition to carbon, and the entire molecule has non-aromaticity. The monovalent non-aromatic hetero-condensed polycyclic group includes a carbazolyl group. In this specification, the divalent non-aromatic hetero-condensed polycyclic group means a divalent group having the same structure as the monovalent non-aromatic hetero-condensed polycyclic group.

[0185] In this specification, C 5 -C 30 A carbocyclic group refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. 5 -C 30 A carbocyclic group is a monocyclic or polycyclic group.

[0186] In this specification, C 1 -C 30 The heterocyclic group refers to a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbon atoms as ring-forming atoms, at least one heteroatom selected from N, O, P, Si, and S. 1 -C 30 The heterocyclic group may be a monocyclic or polycyclic group.

[0187] Replaced C 1 -C 60 Alkyl groups, substituted C 2 -C 60 Alkenyl groups, substituted C 2 -C 60 Alkynyl groups, substituted C 1 -C 60 Alkoxy groups, substituted C 3 -C 10 Cycloalkyl groups, substituted C 1 -C 10 Heterocycloalkyl groups, substituted C 3 -C 10 Cycloalkenyl groups, substituted C 1 -C 10 Heterocycloalkenyl 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 At least one of the substituents of the alkylheteroaryl group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused polycyclic group is Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C60 Alkynyl groups, and C 1 -C 60 Alkoxy groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phosphoric acid group or its salt, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -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 ), -B(Q 16 )(Q 17 ), and -P(=O)(Q 18 )(Q 19 ) C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl groups, and C 1 -C 60 Alkoxy groups; C 3 -C 10 Cycloalkyl groups, C 1-C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic fused polycyclic groups, and monovalent non-aromatic fused heteropolycyclic groups; Deuterium, -F, -Cl, -Br, -I, -CD 3 , -CD 2 H, -CDH 2 , -CF 3 , -CF 2 H, -CFH 2 , 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, phosphoric acid group or its salt, C 1 -C 60 Alkyl group, C 2 -C 60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic condensed heteropolycyclic group, -N(Q 21 )(Q22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), and -P(=O)(Q 28 )(Q 29 ) C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 Heteroaryl groups, monovalent non-aromatic condensed polycyclic groups, and monovalent non-aromatic condensed heteropolycyclic groups; and -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), and -P(=O)(Q 38 )(Q 39 ); Q 1 Or Q 9 , Q 11 Or Q 19 , Q 21 Or Q 29 , and Q 31 Or Q 39 each independently represents hydrogen, deuterium, -F, -Cl, -Br, -I, a hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphate group or a salt thereof, C 1 -C 60 Alkyl group, C 2 -C60 Alkenyl group, C 2 -C 60 Alkynyl group, C 1 -C 60 Alkoxy group, C 3 -C 10 Cycloalkyl groups, C 1 -C 10 Heterocycloalkyl groups, C 3 -C 10 Cycloalkenyl group, C 1 -C 10 Heterocycloalkenyl group, C 6 -C 60 Aryl group, C 1 -C 60 Alkyl groups and C 6 -C 60 C substituted with at least one of an aryl group 6 -C 60 Aryl group, C 6 -C 60 Aryloxy group, C 6 -C 60 Arylthio group, C 1 -C 60 It is selected from the group consisting of a heteroaryl group, a monovalent non-aromatic fused polycyclic group, and a monovalent non-aromatic fused polycyclic heterocyclic group.

[0188] The compound and the organic light-emitting device according to an embodiment of the present invention will be described in more detail below with reference to synthesis examples and examples, but the present invention is not limited to the following synthesis examples and examples. In the following synthesis examples, in the expression "'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.

[0189] [Example]

[0190] <Synthesis Example 1: Synthesis of Compound 2>

[0191] [ka]

[0192] <Synthesis of intermediate 2-2>

[0193] 2-Bromo-9H-carbazole 40.6mmol (10g), 2-Bromopyridine 61.0mmol (9.6g), CuI 20.3mmol (3.9g), K 3 PO 4 60.1 mmol (12.9 g) was mixed with 150 ml of 1,4-dioxane and refluxed at 120° C. for 12 hours. The reaction product obtained was cooled, and the organic layer extracted using a mixture of ethyl acetate and water was washed three times with water, dried over magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography (eluent: dichloromethane and hexane) to obtain intermediate 2-2 (yield: 83%). MALDI-TOF(m / z):323.02[M] +

[0194] <Synthesis of intermediate 2-1>

[0195] Intermediate 2-2 21.7 mmol (7 g), [1,2,4]triazolo[1,5-F]phenanthridin-11-ol 21.7 mmol, CuI 4.4 mmol (0.8 g), K 2 CO 3 43.4 mmol (6.0 g) of the amine compound and 21.7 mmol (1.8 g) of 1-methylimidazole were added to 110 ml of dimethylformamide and refluxed at 130° C. for 48 hours. The reaction mixture was cooled, and the organic layer extracted using a mixture of ethyl acetate and water was washed three times with water, dried over magnesium sulfate, and then subjected to silica gel column chromatography (eluent: dichloromethane and hexane) to obtain intermediate 2-1 (yield: 29%). MALDI-TOF(m / z):478.16[M] +

[0196] <Synthesis of compound 2>

[0197] PtCl 2 (NCPh) 22.1 mmol (1.0 g) of the intermediate 2-1 and 2.1 mmol (1.0 g) of the intermediate 2-1 were mixed with benzonitrile (100 mL) and refluxed under nitrogen for 24 hours. After the reaction was completed, the mixture was cooled to room temperature, and the solvent was removed to obtain a solid, which was then dried and subjected to silica gel column chromatography (eluent: dichloromethane and hexane) to obtain compound 2 (yield: 25%). MALDI-TOF(m / z):671.11[M] +

[0198] <Synthesis Example 2: Synthesis of Compound 3>

[0199] [ka]

[0200] <Synthesis of intermediate 3-2>

[0201] 61.0 mmol (15 g) of 2-bromo-9H-carbazole, 91.4 mmol (19.6 g) of 2-bromo-4-(tert-butyl)pyridine, 30.5 mmol (5.8 g) of CuI, and K 3 PO 4 91.4 mmol (19.4 g) of 1,2-diaminocyclohexane and 61.0 mmol (7.0 g) of 1,2-diaminocyclohexane were mixed with 225 ml of 1,4-dioxane and refluxed at 120° C. for 12 hours. The reaction mixture was cooled, and the organic layer extracted using a mixture of ethyl acetate and water was washed three times with water, dried over magnesium sulfate, and the solvent was removed under reduced pressure to obtain a crude product, which was subjected to silica gel column chromatography (eluent: dichloromethane and hexane) to obtain intermediate 3-2 (yield: 68%). MALDI-TOF(m / z):379.07[M] +

[0202] <Synthesis of intermediate 3-1>

[0203] Intermediate 3-1 (yield 28%) was synthesized using the same method as for synthesizing intermediate 2-1 in Synthesis Example 1, except that intermediate 3-2 was used instead of intermediate 2-2. MALDI-TOF(m / z):534.22[M] +

[0204] <Synthesis of compound 3>

[0205] Compound 3 (yield 34%) was synthesized using the same method as for synthesizing compound 2 in Synthesis Example 1, except that intermediate 3-1 was used instead of intermediate 2-1. MALDI-TOF(m / z):727.16[M] +

[0206] <Synthesis Example 3: Synthesis of Compound 4>

[0207] [ka]

[0208] <Synthesis of intermediate 4-2>

[0209] Intermediate 4-2 was synthesized using the same method as that for intermediate 2-2 in Synthesis Example 1 above, except that starting material 4-3 was used instead of 2-bromo-9H-carbazole.

[0210] <Synthesis of intermediate 4-1>

[0211] Intermediate 4-1 was synthesized in the same manner as in Synthesis Example 1 for intermediate 2-1, except that intermediate 4-2 was used instead of intermediate 2-2.

[0212] <Synthesis of compound 4>

[0213] Compound 4 (yield 34%) was synthesized using the same method as for synthesizing compound 2 in Synthesis Example 1, except that intermediate 4-1 was used instead of intermediate 2-1. MALDI-TOF(m / z):775.17[M] +

[0214] <Synthesis Example 4: Synthesis of Compound 17>

[0215] [ka]

[0216] <Synthesis of intermediate 17-1>

[0217] Intermediate 2-1 5.9mmol (2.8g), 1-iodotoluene 6.4mmol (1.4g), CuI 5.9mmol (1.1g), Na 2 CO 3 11.7 mmol (1.2 g) of the amine compound and 1.2 mmol (0.3 g) of triphenylphosphine were mixed with 30 ml of dimethyl sulfoxide and refluxed at 160° C. for 12 hours. The reaction mixture was cooled, and the organic layer extracted using a mixture of ethyl acetate and water was washed three times with water and dried over magnesium sulfate. The solvent was removed under reduced pressure to obtain a crude product, which was then subjected to silica gel column chromatography (eluent: ethyl acetate and hexane) to obtain intermediate 17-1 (yield: 30%). MALDI-TOF(m / z):568.20[M] +

[0218] <Synthesis of compound 17>

[0219] Compound 17 (yield 47%) was synthesized using the same method as for synthesizing compound 2 in Synthesis Example 1, except that intermediate 17-1 was used instead of intermediate 2-1. MALDI-TOF(m / z):761.16[M] +

[0220] <Evaluation example 1: T1 energy level evaluation>

[0221] The T of each compound was measured by the method shown in Table 2 below. 1Energy levels were assessed and the results are summarized in Table 3.

[0222] [Table 2]

[0223] [Table 3]

[0224] [ka]

[0225] From Table 3 above, compounds 2, 3, 4, and 17 had higher or similar levels of T compared to compound A. 1 It is confirmed that the energy level

[0226] <Evaluation example 2: PL spectrum evaluation>

[0227] Compound 2 was diluted in toluene to a concentration of 1.0 mM, and the PL (photoluminescence) spectrum was measured at room temperature using an ISC PC1 spectrofluorometer equipped with a xenon lamp. This was repeated for compounds 3, 4, and 17, and the results are shown in Table 4. The PL spectra of compounds 3 and 17 are shown in FIG. 2.

[0228] [Table 4]

[0229] From Table 4 above, it is confirmed that compounds 2, 3, 4, and 17 emit deep blue light with small half-width ratios.

[0230] <Evaluation Example 3: Evaluation of luminescence quantum efficiency (PLQY)>

[0231] Polymethylmethacrylate (PMMA) CH 2 Cl 2 The solution was mixed with a mixture of 8 wt% CBP and compound 3 (the content of compound 3 was 10 parts by weight per 100 parts by weight of the mixture), and the resultant was coated on a quartz substrate using a spin coater, heat-treated in an oven at 80°C, and then cooled to room temperature to prepare a film.

[0232] The photoluminescence quantum yields in film were evaluated using a Hamamatsu Photonics absolute PL quantum yield measurement system equipped with a xenon light source, a monochromator, a photonic multichannel analyzer, and an integrating sphere, and employing PLQY measurement software (Hamamatsu Photonics, Ltd., Shizuoka, Japan), to confirm the PLQY in film of the compound 3.

[0233] The above procedure was repeated for compound 17 to confirm the PLQY in film of compounds 3 and 17, and the results are summarized in Table 5 below.

[0234] [Table 5]

[0235] From Table 5 above, it is confirmed that compounds 3 and 17 have high PLQY values.

[0236] Example 1

[0237] 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 was completed, the substrate was ultrasonically cleaned using isopropyl alcohol, acetone, and methanol in that order, dried, and then transferred to a plasma cleaner. The substrate was then cleaned for 5 minutes using oxygen plasma, and then transferred to a vacuum deposition machine.

[0238] Compound HT3 was vacuum-deposited on the ITO electrode of the glass substrate to form a first hole injection layer with a thickness of 3,500 Å, compound HT-D1 was vacuum-deposited on the first hole injection layer to form a second hole injection layer with a thickness of 300 Å, and TAPC was vacuum-deposited on the second hole injection layer to form an electron blocking layer with a thickness of 100 Å, thereby forming a hole transport region.

[0239] On the hole transport region, compound H52 and compound 17 (dopant, 10%) were co-evaporated to form a 300 Å thick light emitting layer.

[0240] Compound ET3 was vacuum-deposited on the light-emitting layer to form a 250 Å-thick electron transport layer, and then ET-D1 (Liq) was deposited on the electron transport layer to form a 5 Å-thick electron injection layer. Finally, a 1,000 Å-thick Al second electrode (cathode) was formed on the electron injection layer to produce an organic light-emitting element.

[0241] [ka]

[0242] Comparative Example A

[0243] An organic light emitting device was prepared in the same manner as in Example 1, except that compound A was used instead of compound 17 as a dopant when forming the light emitting layer.

[0244] Evaluation Example 4: Evaluation of organic light-emitting device characteristics

[0245] The EL spectrum, CIE color coordinates, driving voltage, external quantum efficiency, efficiency, and converted efficiency were evaluated for each of the organic light-emitting devices fabricated in Example 1 and Comparative Example A. The specific evaluation methods are as follows, and the results are shown in Table 6. The EL spectra of Example 1 and Comparative Example A are shown in FIG. 3, and the driving voltage vs. current density graph of Example 1 is shown in FIG. 4.

[0246] (1) EL spectrum measurement The luminance of the manufactured organic light emitting device was measured using a luminance meter (Minolta Cs-1000A) to determine whether the luminance was 500 cd / m 2 After the EL spectrum was measured and the results were obtained, the maximum emission wavelength and the half-width ratio were evaluated.

[0247] (2) Measurement of current density change due to voltage The voltage of the fabricated organic light emitting device was increased from 0 V to 10 V, and the current flowing through the unit element was measured using a current-voltage meter (Keithley 2400). The measured current value was divided by the area to obtain the result.

[0248] (3) Measurement of luminance change due to voltage The voltage of the fabricated organic light emitting device was increased from 0V to 10V, and the luminance was measured using a luminance meter (Minolta Cs-1000A) to obtain the results.

[0249] (4) Equivalent efficiency measurement Using the luminance, current density, and voltage measured from (2) and (3) above, the same current density (10 mA / cm 2 The current efficiency (cd / A) was then calculated. The current efficiency was then divided by the y value of the CIE color coordinates measured in (6) to calculate the converted efficiency.

[0250] (5) External quantum efficiency measurement The evaluation was carried out using a current / voltage meter (Keithley 2400) and a luminance meter (Minolta Cs-1000A).

[0251] [Table 6]

[0252] [ka]

[0253] From Table 6, FIGS. 3 and 4, it can be seen that the organic light emitting device of Example 1 emits deep blue light having a narrow half-width and excellent color purity compared to Comparative Example A, while at the same time having a low driving voltage, high external quantum luminous efficiency, and high converted luminous efficiency.

[0254] 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 various modifications can be made without departing from the technical scope of the present invention. [Industrial Applicability]

[0255] The organometallic compound of the present invention and the organic light-emitting device and diagnostic composition containing the same can be effectively applied to, for example, technical fields related to biochemical diagnosis. [Explanation of symbols]

[0256] 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 1-2 or 1-2(1): 【Chemistry 1-2】 【Chemistry 1-2(1)】 In the above chemical formula 1-2 or 1-2(1), M is platinum (Pt); X １ Or X ４ , Y ４１ , and Y ４２ are each independently C or N; Y ４３ and Y ４４ are, independently of each other, C or N, A ３ is a chemical bond, X １ and M bond, X ２ and M bond, X ３ and M, and X ４ Two of the bonds between and M are coordinate bonds and the remaining two are covalent bonds; Z １１ is C(R １１ ) and Z １２ is C(R １２ ) and Z １３ is C(R １３ ) and R １１ Or R １３ For an explanation of R １ This is the same as the explanation for A １１ is *-C(R ８ａ ) (R ９ａ )-*', Z ２１ is N or C(R ２１ ) and Z ２２ is N or C(R ２２ ) and Z ２３ is N or C(R ２３ ) and Z ２４ is N or C(R ２４ ) and Z ２５ is N or C(R ２５ ) and Z ２６ is N or C(R ２６ ) and R ２１ Or R ２６ For explanations of each, see R below. ２ This is the same as the explanation for 【change】 The moiety represented by the formula A1-1(1) is 【change】 The moiety represented by the formula: 【Chemical A1-1(1)(CY3-1)】 In the formula A1-1(1) and the formula CY3-1, a14 is selected from the group consisting of integers from 0 to 4; Z ３１ is N or C(R ３１ ) and Z ３２ is N or C(R ３２ ) and R 31 and R 32 correspond to R 3 ; ３１ and R ３２ For explanations of each, see R below. ３ This is the same as the explanation for Z ５１ is N or C(R ５１ ) and Z ５２ is N or C(R ５２ ) and Z ５３ is N or C(R ５３ ) and Z ５４ is N or C(R ５４ ) and R 51 to R 54 correspond to R 5 ; ５１ ~R ５４ For explanations of each, see R below. ５ This is the same as the explanation for In the formula A1-1(1), * is a bonding site with M in the formula 1, *' is a bonding site with an adjacent atom in the formula 1, In the formula CY3-1, the two *'s are binding sites with M in formula 1, and *'' is T in formula 1. ２ It is a binding site for T ２ is *-N(R ８ )-*', *-B(R ８ )-*', *-C(R ８ ) (R ９ )- *', *-Si(R ８ ) (R ９ )-*', *-S-*', *-Se-*', *-O-*', or *-S(=O) ２ -*', R １ ~R ５ , R ８ , R ９ , R ８ａ and R ９ａ are independent of each other, Hydrogen, deuterium, -F, cyano group C １ -C ２０ Alkyl groups; Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano group, C １ -C １０ C substituted with at least one of an alkyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, a naphthyl group, a pyridinyl group, and a pyrimidinyl group; １ -C ２０ Alkyl groups; Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, C １ -C ２０ An alkylphenyl group, a naphthyl group, a fluorenyl group, a carbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group; Deuterium, -F, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ , cyano group, C １ -C ２０ Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, phenyl group, biphenyl group, C １ -C ２０ a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, an adamantanyl group, a norbornanyl group, a norbornenyl group, a phenyl group, a biphenyl group, C １ -C ２０ Alkylphenyl, naphthyl, fluorenyl, carbazolyl, dibenzofuranyl and dibenzothiophenyl groups; and -Si(Q ３ ) (Q ４ ) (Q ５ ); Q ３ Or Q ５ are independent of each other, -CH ３ 、-CD ３ 、-CD ２ H、-CDH ２ 、-CH ２ CH ３ 、-CH ２ CD ３ 、-CH ２ CD ２ H、-CH ２ CDH ２ 、-CHDCH ３ 、-CHDCD ２ H、-CHDCDH ２ 、-CHDCD ３ 、-CD ２ CH ３ 、-CD ２ CD ３ 、-CD ２ CD ２ H and -CD ２ CDH ２ ; n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, and naphthyl; and Deuterium, C １ -C １０ selected from the group consisting of n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl and naphthyl, each of which is substituted with at least one group selected from the group consisting of an alkyl group and a phenyl group; a1 and a5 are each independently selected from integers of 0 to 4; a3 is selected from the group consisting of integers from 0 to 2; a4 is 0 or 1.

2. In chemical formula 1-2, 【change】 The organometallic compound according to claim 1, wherein the moiety represented by the formula: is represented by one of the formulae CY1-1 to CY1-16: 【Chemistry (CY1-1)-(CY1-16)】 In the chemical formulas CY1-1 to CY1-16, X １ and R １ The explanations for are the same as those for X 1 and R 1 in claim 1 , R １ａ Or R １ｄ The explanation of each is given in R １ This is the same as the explanation for However, R １ , and R １ａ Or R １ｄ is not hydrogen, In the formulae CY1-1 to CY1-16, * is a bonding site with M in formula 1, *' is an adjacent atom T in formula 1, １ It is the binding site for

3. The organometallic compound according to claim 1, which is one of the following compounds 2 to 7, compounds 17 to 25, compounds 32, compounds 37 to 45, compounds 50, compounds 53 to 59, compounds 65, compounds 69 to 78, compounds 82, compounds 85 to 103, compounds 123, and compounds 124. 【Chemistry (2-7) (17-25) 32】 【Chemistry (37-45) 50 (53-59) 65 (69-72)】 【Chemistry (73-78) 82 (85-103) (123-124)】

4. 2. The organometallic compound according to claim 1, characterized in that in the emission spectrum, the peak has a maximum emission wavelength in the range of 420 nm to 500 nm and a full width at half maximum (FWHM) in the range of 30 nm to 80 nm.

5. A first electrode; A second electrode; an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer; The organic light-emitting device according to claim 1 , wherein the organic layer comprises at least one organometallic compound.

6. the first electrode is an anode; the second electrode is a cathode; the organic layer further includes a hole transport region interposed between the first electrode and the light emitting layer, and an electron transport region interposed between the light emitting layer and the second electrode; the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof; The organic light emitting device of claim 5 , wherein the electron transport region comprises a hole blocking layer, an electron transport layer, an electron injection 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 light emitted from the light-emitting layer is blue light; The organic light emitting device according to claim 7, wherein the CIE y coordinate of the blue light is in the range of 0.10 to 0.

340.

9. The light-emitting layer further comprises a host, The organic light emitting device according to claim 7, wherein the content of the host is greater than the content of the organometallic compound.

10. A diagnostic composition comprising one or more organometallic compounds according to any one of claims 1 to 4.

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