Organometallic compounds, organic light-emitting devices containing them, and electronic devices containing organic light-emitting devices

Abstract

To provide an organometallic compound, an organic light-emitting device including the same, and an electronic apparatus including the organic light-emitting device.SOLUTION: The inventive organometallic compound is represented by the formula 1. For details of the formula 1, refer to descriptions in the Specifications.SELECTED DRAWING: Figure 1

Description

[Technical Field]

[0001] The present invention relates to organometallic compounds, organic light-emitting devices containing the same, and electronic devices including organic light-emitting devices. [Background technology]

[0002] Organic light-emitting devices are self-emitting elements that excel in characteristics such as viewing angle, response time, brightness, driving voltage, and response speed, and can be made multi-colored.

[0003] For example, an organic light-emitting device comprises an anode, a cathode, and an organic layer interposed between the anode and the cathode, which includes a light-emitting layer. A hole transport region is provided between the anode and the light-emitting layer, and an electron transport region is provided between the light-emitting layer and the cathode. Holes injected from the anode move to the light-emitting layer via the hole transport region, and electrons injected from the cathode move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to generate an exciton. Light, such as visible light, is generated as the exciton changes from the excited state to the ground state. [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2017-39713 [Overview of the Initiative] [Problems that the invention aims to solve]

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

[0006] An organometallic compound according to one aspect of the present invention, which has been made to achieve the above object, is represented by the following Chemical Formula 1.

Chemical Formula

[0007] In other aspects, an organic light-emitting device is provided, comprising a first electrode, a second electrode, and an organic layer interposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer contains one or more organometallic compounds represented by the chemical formula 1.

[0008] Further, according to another aspect, an electronic device including the organic light-emitting element is provided.

[0009] The organometallic compound is included in the light-emitting layer of the organic layer, and the organometallic compound included in the light-emitting layer acts as a dopant. [Effects of the Invention]

[0010] The organometallic compounds of the present invention possess excellent thermal stability and electrical properties, and electronic devices employing these organometallic compounds, such as organic light-emitting devices, can emit light with a relatively narrow full width at half maximum (FWHM) while exhibiting improved external quantum efficiency and improved lifetime characteristics. [Brief explanation of the drawing]

[0011] [Figure 1] This is a schematic cross-sectional view showing an example of an organic light-emitting element. [Modes for carrying out the invention]

[0012] The following describes in detail specific examples of embodiments for carrying out the present invention.

[0013] The organometallic compound of the present invention is represented by the following chemical formula 1.

[0014] [ka]

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

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

[0017] Other examples include M being iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), rhodium (Rh), palladium (Pd), or gold (Au).

[0018] According to one example, in the above chemical formula 1, M is Pt, Pd, or Au.

[0019] In the above chemical formula 1, X1 to X4 are each independently either C or N.

[0020] For example, in the above chemical formula 1, X1 and X3 are C, and X2 and X4 are N.

[0021] In the above chemical formula 1, X5 is O, S, N(R'), C(R')(R”), or C(=O).

[0022] In the chemical formula 1 above, the bond between X5 and M is a covalent bond. Of the bonds between X2 and M, X3 and M, and X4 and M, one is a covalent bond, and the remaining two are coordinate bonds.

[0023] For example, in the chemical formula 1 above, the bond between X2 and M is a coordinate covalent bond.

[0024] According to one example, in the above chemical formula 1, the bond between X5 and M, and the bond between X3 and M are covalent bonds, while the bond between X2 and M, and the bond between X4 and M are coordinate bonds.

[0025] In the above chemical formula 1, rings CY1 to CY4 are each independently C5-C 30 Carbon ring group or C1-C 30 It is a heterocyclic group.

[0026] For example, in the above chemical formula 1, each of the rings CY1 to CY4 is independently i) a first ring, ii) a second ring, iii) a condensed ring formed by the fusion of two or more first rings, iv) a condensed ring formed by the fusion of two or more second rings, or v) a condensed ring formed by the fusion of one or more first rings and one or more second rings. The first ring is a cyclopentane group, cyclopentene group, furan group, thiophene group, pyrrole group, silole group, borol group, phosphole group, germole group, selenofen group, oxazole group, oxadiazole group, oxatriazole group, thiazole group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, or azasilol group. The second ring is an adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0027] As another example, in the above chemical formula 1, rings CY1 to CY4 are independently: cyclopentene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzobolol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzof Lan group, carbazole group, dibenzobolol group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzobolol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, A Zabenzofuran group, azacarbazole group, azadibenzobolol group, azadibenzophosphorus group, azafluorene group, azadibenzosilol group, azadibenzogermol 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 group is a phosphorus group, phenanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, or norbornene group.

[0028] According to one example, ring CY1 and ring CY3 are independent of each other. Benzene group, naphthalene group, fluorene group, carbazole group, dibenzothiophene group, or dibenzofuran group; or A benzene group, naphthalene group, fluorene group, carbazole group, dibenzothiophene group, or dibenzofuran group, which is formed by condensation of a cyclohexane group, a cyclohexene group, a norbornane group, or any combination thereof;

[0029] According to other examples, X2 is N, and the ring CY2 is benzimidazole group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group; or A benzimidazole group, pyridine group, pyrimidine group, pyridazine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group, which are condensed with a cyclohexane group, a cyclohexene group, a norbornane group, or any combination thereof.

[0030] Furthermore, according to other examples, the ring CY4 is, Pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group; or A pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group, which is formed by condensation of a cyclohexane group, a cyclohexene group, a norbornane group, or any combination thereof.

[0031] In the above chemical formula 1, T1 to T4 are each independently a single bond, a double bond, and *-N(R 5a )-*', *-B(R 5a )-*'、*-P(R 5a )-*', *-C(R 5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *-S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*', *=C(R 5a )-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C-*', at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 It is a heterocyclic group.

[0032] For example, in the above chemical formula 1, T1 and T2 are single bonds, and T3 is a single bond, *-N(R 5a )-*', *-B(R 5a )-*'、*-P(R 5a )-*', *-C(R 5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R 5a )(R 5b It is )-*', *-S-*', or *-O-*'.

[0033] In the above chemical formula 1, n1 to n4 represent the number of T1 to T4, and each is independently either 0 or 1, however, three or more of n1 to n4 are 1. That is, the organometallic compound represented by the above chemical formula 1 has a tetradentate ligand. For example, the sum of n1 to n4 is 3 or 4.

[0034] In the above chemical formula 1, if n1 is 0, T1 does not exist; if n2 is 0, T2 does not exist; if n3 is 0, T3 does not exist; and if n4 is 0, T4 does not exist.

[0035] According to one example, in the above chemical formula 1, n1 to n3 are 1, and n4 is 0.

[0036] In the above chemical formula 1, Z1 to Z4 are each independently groups represented by the following chemical formula 51.

[0037] [ka]

[0038] For a description of the above chemical formula 51, please refer to the relevant section of this specification.

[0039] In the above chemical formula 1, d1 to d4 represent the respective numbers of Z1 to Z4, and each is an independent integer between 0 and 20. When d1 is 2 or greater, 2 or greater Z1s are either identical or different from each other; when d2 is 2 or greater, 2 or greater Z2s are either identical or different from each other; when d3 is 2 or greater, 2 or greater Z3s are either identical or different from each other; and when d4 is 2 or greater, 2 or greater Z4s are either identical or different from each other. For example, d1 to d4 are each independently 0, 1, 2, or 3.

[0040] In the above chemical formulas 1 and 51, L1 to L4 and L 51 Each is independent, single-bonded, and has at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 It is a heterocyclic group.

[0041] For example, in the above chemical formulas 1 and 51, L1 to L4 and L 51 Each of them operates independently. Single bond; or At least one R 10aSubstituted or unsubstituted cyclopentene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopentadiene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, indole group, benzobolol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzobolol Azaindole group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azaindole group, azabenzobolol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azaca Luvazole group, azadibenzobolol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, fe The group is a nanthroline group, pyrrole group, pyrazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzoxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane group, or norbornene group.

[0042] According to one example, in the above chemical formulas 1 and 51, L1 to L4 and L 51Each of them operates independently. Single bond; or At least one R 10a A substituted or unsubstituted benzene group, naphthalene group, pyridine group, fluorene group, carbazole group, dibenzofuran group, or dibenzothiophene group;

[0043] In the above chemical formulas 1 and 51, b1 to b4 and b51 are L1 to L4 and L 51 These represent the number of each element, and each is an independent integer between 1 and 10. If b1 is 2 or greater, then L1 of 2 or greater is either the same or different from each other; if b2 is 2 or greater, then L2 of 2 or greater is either the same or different from each other; if b3 is 2 or greater, then L3 of 2 or greater is either the same or different from each other; if b4 is 2 or greater, then L4 of 2 or greater is either the same or different from each other; if b51 is 2 or greater, then L 51 These are either identical or different from one another. For example, b1 through b4 and b51 are independently 1, 2, or 3, respectively.

[0044] In the above chemical formulas 1 and 51, R1 to R4, R 5a , R 5b , R', R'', and Q 51 ~Q 53 Each of these is independently a group represented by the above chemical formula 51, hydrogen, deuterium, -F, -Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, substituted or unsubstituted C1-C 60 Alkyl alkyl groups, substituted or unsubstituted C2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substituted or unsubstituted C1-C 60 alkoxy group, substituted or unsubstituted C1-C 60 Alkylthio group, substituted or unsubstituted C3-C 10 Cycloalkyl groups, substituted or unsubstituted C1-C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C10 Cycloalkenyl group, substituted or unsubstituted C1-C 10 Heterocycloalkenyl group, substituted or unsubstituted C6-C 60 Aryl group, substituted or unsubstituted C7-C 60 Alkylaryl group, substituted or unsubstituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 Arylthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substituted or unsubstituted C2-C 60 Alkyl heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9), but the Q of the above chemical formula 51 51 ~Q 53 At least one of them is a substituted or non-substituted C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 It is a heteroaryl group, a substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group.

[0045] For explanations regarding each of Q1 through Q9, please refer to the relevant sections of this specification.

[0046] According to one example, Q 51 ~Q 53 This is not the group represented by the above chemical formula 51. According to other examples, R1 to R4, R', R'', and Q of the above chemical formula 1. 51 ~Q 53 This is not the group represented by the above chemical formula 51.

[0047] According to other concrete examples, in the above chemical formulas 1 and 51, R1 to R4, R5a , R 5b , R', R'', and Q 51 ~Q 53 Each of them operates independently. The group represented by the above chemical formula 51, hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, -SF5, C1-C 20 Alkyl alkyl group, C1-C 20 Alkenyl group, C1-C 20 Alkoxy group, or C1-C 20 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group (bicyclo[2.2.1]heptyl group), norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl) norbornanyl group ((C1-C 20 Alkyl)bicyclo[2.2.1]heptyl group), (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 C1-C substituted with alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, pyridinyl group, pyrimidinyl group, or any combination thereof 20 Alkyl alkyl group, C1-C 20 Alkenyl group, C1-C 20 Alkoxy group, or C1-C 20 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norborneyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclopentyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl)cycloheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl)adamantanyl group, (C1-C 20 Alkyl) norbornanyl group, (C1-C 20 Alkyl)norborneyl group, (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohexenyl group, (C1-C 20Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, deuterated phenyl group, fluorinated phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenanthrenyl group, anthracenyl group, fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, thiophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyridinyl group, pyrimidinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazolyl group, synnolinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothia Cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norbornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, fluorenyl group, phenantrenyl 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, pyridinyl group, pyrimidinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoki Salinyl group, quinazolinyl group, synnorinyl group, carbazolyl group, phenanthrolinyl group, benzimidazolyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzoxazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadiazolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocarbazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group, azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group; or -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9); Q1 through Q9 are each independent of each other. Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, -CD2CDH2, -CF3, -CF2H, -CFH2, -CH2CF3, -CH2CF2H, -CH2CFH2, -CHFCH3, -CHFCF2H, -CHFCFH2, -CHFCF3, -CF2CF3, -CF2CF2H, or -CF2CFH2; or Deuterium, -F, C1-C 10n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, substituted or unsubstituted with alkyl groups, phenyl groups, or any combination thereof;

[0048] Furthermore, according to other concrete examples, in the above chemical formula 1, R1 to R4, R 5a , R 5b R' and R'' are independent of each other. The group represented by the above chemical formula 51, hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 A heterocycloalkyl group, or any combination thereof, substituted or unsubstituted C1-C 20 alkyl group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl alkyl group, C1-C 20 Alkoxy group, deuterated C1-C 20 Alkoxy group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, biphenyl groups, naphthyl groups, pyridinyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; or -Si(Q3)(Q4)(Q5) or -Ge(Q3)(Q4)(Q5);

[0049] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 ~Q 53 Each of them operates independently. Hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 A heterocycloalkyl group, or any combination thereof, substituted or unsubstituted C1-C 20 alkyl group; or Deuterium, -F, cyano group, C1-C 20Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl alkyl group, C1-C 20 Alkoxy group, deuterated C1-C 20 Alkoxy group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, phenyl groups, biphenyl groups, naphthyl groups, pyridinyl groups, fluorenyl groups, carbazolyl groups, dibenzofuranyl groups, or dibenzothiophenyl groups; however, Q 51 ~Q 53 At least one of the following (for example, Q 53 ) is deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl, fluorinated, deuterated C1-C 20 Alkoxy group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, (C1-C 20 Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 The group is an alkyl)biphenyl group, or any combination thereof, which may be substituted or unsubstituted with a phenyl group, biphenyl group, naphthyl group, pyridinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, or dibenzothiophenyl group.

[0050] Furthermore, according to other concrete examples, in the above chemical formula 51, i) Q 51 and Q 52 ii) Q 51 Q is hydrogen or deuterium. 52 Is it not hydrogen and deuterium, or iii) Q 51 and Q 52 None of them are hydrogen or deuterium.

[0051] Furthermore, according to other concrete examples, in the above chemical formulas 1 and 51, R1 to R4, R 5a , R 5b , R', R'', and Q 51 ~Q 53 These are, independently, the group represented by the above chemical formula 51, hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, C2-C 10 Alkenyl group, C1-C 10 Alkoxy group, C1-C 10Alkylthio group, a group represented by one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with -F, a group represented by one of the following chemical formulas 9-201 to 9-227, a group in which at least one hydrogen atom of one of the following chemical formulas 9-201 to 9-227 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 9-201 to 9-227 is substituted with -F, a group represented by one of the following chemical formulas 10-1 to 10-129, a group in which 10-1 to 10- A group in which at least one hydrogen atom from 129 is substituted with deuterium, a group in which at least one hydrogen atom from one of the following chemical formulas 10-1 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen atom from one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, a group in which at least one hydrogen atom from one of the following chemical formulas 10-201 to 10-350 is substituted with -F, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (however, for explanations of Q3 to Q5, refer to the respective sections described herein).

[0052] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 and Q 52 Each is independently hydrogen or deuterium, and Q 53 This refers to a group represented by one of the following chemical formulas 10-12 to 10-129, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with -F.

[0053] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 Q is hydrogen or deuterium. 52 Q is a group represented by -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with -F. 53 This refers to a group represented by one of the following chemical formulas 10-12 to 10-129, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with -F.

[0054] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 and Q 52 Each of these is independently a group represented by -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, one of the following chemical formulas 9-1 to 9-39, a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 9-1 to 9-39 is substituted with -F, and Q 53This refers to a group represented by one of the following chemical formulas 10-12 to 10-129, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with -F.

[0055] Furthermore, according to other concrete examples, Q of the above chemical formula 51 51 ~Q 53 At least one of the following (for example, Q 51 ~Q 53 One of these is a group represented by one of the following chemical formulas 10-12 to 10-129, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with deuterium, a group in which at least one hydrogen atom of one of the following chemical formulas 10-12 to 10-129 is substituted with -F, a group represented by one of the following chemical formulas 10-201 to 10-350, a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with deuterium, or a group in which at least one hydrogen atom of one of the following chemical formulas 10-201 to 10-350 is substituted with -F.

[0056] [ka]

[0057] [ka]

[0058] [ka] [ka] [ka]

[0059] [ka] [ka] [ka] [ka]

[0060] In the above chemical formulas 9-1 to 9-39, 9-201 to 9-227, 10-1 to 10-129, and 10-201 to 10-350, * represents a bonding site with an adjacent atom, Ph represents a phenyl group, TMS represents a trimethylsilyl group, and TMG represents a trimethylgermyl group.

[0061] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 9-1 to 9-39 is substituted with deuterium" and "groups in which at least one hydrogen atom from chemical formulas 9-201 to 9-227 is substituted with deuterium" are, for example, the groups represented by the following chemical formulas 9-501 to 9-514 and 9-601 to 9-636.

[0062] [ka]

[0063] [ka]

[0064] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 9-1 to 9-39 is substituted with -F" and "groups in which at least one hydrogen atom from chemical formulas 9-201 to 9-227 is substituted with -F" are, for example, the groups represented by the following chemical formulas 9-701 to 9-710.

[0065] [ka]

[0066] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 10-1 to 10-129 is substituted with deuterium" and "groups in which at least one hydrogen atom from chemical formulas 10-201 to 10-350 is substituted with deuterium" are, for example, the groups represented by the following chemical formulas 10-501 to 10-553.

[0067] [ka] [ka]

[0068] The above-mentioned "groups in which at least one hydrogen atom from chemical formulas 10-1 to 10-129 is substituted with -F" and "groups in which at least one hydrogen atom from chemical formulas 10-201 to 10-350 is substituted with -F" are, for example, the groups represented by the following chemical formulas 10-601 to 10-617.

[0069] [ka]

[0070] c1 to c4 and a1 to a4 in the above chemical formula 1 are R1 to R4, *-[(L1) b1 -(R1) c1 The base represented by ], *-[(L2) b2 -(R2) c2 The base represented by ], *-[(L3) b3 -(R3) c3 The base represented by ], and *-[(L4)b4 -(R4)c4] represents the number of elements in each base, and each is an independent integer from 0 to 20. If c1 is 2 or greater, then 2 or greater R1 elements are either identical or different from each other; if c2 is 2 or greater, then 2 or greater R2 elements are either identical or different from each other; if c3 is 2 or greater, then 2 or greater R3 elements are either identical or different from each other; if c4 is 2 or greater, then 2 or greater R4 elements are either identical or different from each other; if a1 is 2 or greater, then 2 or greater *-[(L1) b1 -(R1) c1 The bases represented by ] are either identical or different from each other, and if a2 is 2 or more, then 2 or more *-[(L2) b2 -(R2) c2 The bases represented by ] are either identical or different from each other, and if a3 is 2 or more, then 2 or more *-[(L3) b3 -(R3) c3 The bases represented by ] are either identical or different from each other, and if a4 is 2 or more, then 2 or more *-[(L4) b4 -(R4) c4 The groups represented by ] are either identical or different from each other. For example, c1 to c4 and a1 to a4 of the above chemical formula 1 are each independently 0, 1, 2, or 3.

[0071] In the above chemical formula 51, c51 is *-C(Q 51 )(Q 52 )(Q 53 This represents the number of elements represented by ), and is an integer from 1 to 20. If c51 is 2 or greater, then *-C(Q) is 2 or greater. 51 )(Q 52 )(Q 53 The bases represented by () are either identical or different from each other. For example, c51 is either 1 or 2.

[0072] The organometallic compound represented by the above chemical formula 1 satisfies at least one of the following conditions 1 and 2.

[0073] <Condition 1> In the above chemical formula 1, the sum of d1 to d4 is 1 or greater. <Condition 2> At least one of T1 to T4 in the above chemical formula 1 is *-N(R 5a )-*', *-B(R 5a )-*'、*-P(R 5a )-*', *-C(R 5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R 5a )(R 5b )-*' and R 5a and R 5b At least one of them is a group represented by the above chemical formula 51. In other words, the organometallic compound represented by chemical formula 1 contains at least one group represented by chemical formula 51.

[0074] According to one example, the organometallic compound represented by the above chemical formula 1 satisfies at least one of the following conditions: <Condition 1A> and <Condition 2A>.

[0075] <Condition 1A> In the above chemical formula 1, i) d1 is 1, and each of d2, d3, and d4 is 0, ii) d2 is 1, and d1, d3, and d4 are each 0, iii) d3 is 1, and d1, d2, and d4 are each 0, iv) d4 is 1, and each of d1, d2, and d3 is 0, v) Each of d1 and d2 is 1, and each of d3 and d4 is 0, vi) Each of d2 and d3 is 1, and each of d1 and d4 is 0, or vii) d2 and d4 are each 1, and d1 and d3 are each 0. <Condition 2A> In the above chemical formula 1, n3 is 1. i)T3 is *-N(R 5a )-*', *-B(R 5a )-*'、*-P(R 5a)-*', *-C(R 5a )=*', or *=C(R 5a )-*' and R 5a This is either a group represented by the above chemical formula 51, or ii) T3 is *-C(R 5a )(R 5b )-*'、*-Si(R 5a )(R 5b )-*'、*-Ge(R 5a )(R 5b )-*', or *-C(R 5a )=C(R 5b )-*' and R 5a and R 5b At least one of these is a group represented by the above chemical formula 51.

[0076] In the above chemical formula 1, i) two or more of the multiple R2 atoms are selectively bonded to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 ii) Two or more of the multiple R3 groups are selectively bonded to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 iii) Two or more of the R4 groups are selectively bonded to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 It forms a heterocyclic group, iv) two or more of R1 to R4, one of R1 to R4, and R 5a , one of R1 to R4, and R 5b , or R 5a and R 5b Each of them selectively binds to each other, and at least one R 10a Substitute or non-substitute C5-C 30A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 It forms a heterocyclic group.

[0077] R 10a For further information, please refer to the explanation regarding R1.

[0078] * and *' represent bonding sites with adjacent atoms, respectively.

[0079] According to one example, in the above chemical formula 51, *-C(Q 51 )(Q 52 )(Q 53 The group represented by ) is one of the chemical formulas 51-1 to 51-25 below.

[0080] [ka]

[0081] In the above chemical formulas 51-1 to 51-25, Q 51 and Q 52 For explanations regarding each of these, please refer to the respective sections in this specification, Q 61 ~Q 66 The descriptions relating to each of these are as follows in this specification, R 10a Refer to the explanation regarding Q 61 ~Q 65 Each of them is not hydrogen, and * is in the above chemical formula 51, L 51 This is a linked site.

[0082] For example, with the above chemical formulas 51-1 to 51-20, i)Q 51 and Q 52 is hydrogen, and Q 61 ~Q 65 These are, independently, deuterium, -F, cyano group, and C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20Alkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, or (C1-C 20 Is it an alkyl)phenyl group? ii) Q 51 is hydrogen, and Q 52 , and Q 61 ~Q 65 These are, independently, deuterium, -F, cyano group, and C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, or (C1-C 20 It is an alkyl)phenyl group, or iii) Q 51 Q 52 , and Q 61 ~Q 65 These are, independently, deuterium, -F, cyano group, and C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1-C fluoride 20 Alkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, or (C1-C 20 It is an alkylphenyl group.

[0083] According to one example, in the above chemical formula 51, L 51 It is a single bond.

[0084] According to other concrete examples, the group represented by the above chemical formula 51 is L 51 This results in a single bond, which is a group represented by one of the chemical formulas 51-1 to 51-20 above.

[0085] Furthermore, according to other concrete examples, the group represented by the above chemical formula 51 is the same as the group represented by one of the following chemical formulas 51(1) to 51(19).

[0086] [ka]

[0087] In the above chemical formulas 51(1) to 51(19), T11 ~T 15 Each of them is represented by the above chemical formula 51, *-C(Q 51 )(Q 52 )(Q 53 It is a group represented by ), T 11 ~T 15 They are either identical or different from each other, R 10a For further explanation, please refer to the explanation for R1 in this specification, where * indicates a bonding site with an adjacent atom.

[0088] Furthermore, according to other concrete examples, in the above chemical formula 1, n1 is 1 and n4 is 0. [ka] The group represented by is one of the following chemical formulas CY1(1) to CY1(20).

[0089] [ka]

[0090] The above chemical formulas CY1(1) to CY1(20) For a description of X1, please refer to the relevant section in this specification. X 19 O, S, N(R) 19a ), C(R 19a )(R 19b ), or Si(R 19a )(R 19b ) and R 19a and R 19b For explanations regarding each of these, please refer to the explanation regarding R1 in this specification. * represents the bonding site with X5 in chemical formula 1. *' represents the bonding site with T1 in chemical formula 1.

[0091] Furthermore, according to other concrete examples, in the above chemical formula 1, n1 is 1 and n4 is 0. [ka] The group represented by is one of the following chemical formulas: CY1-1 to CY1-18, and ZCY1-1 to ZCY1-32.

[0092] [ka]

[0093] [ka]

[0094] The above chemical formulas CY1-1 to CY1-18 and ZCY1-1 to ZCY1-32, For a description of X1, please refer to the relevant section in this specification. R 11 ~R 14 For explanations of each of these, see the explanation for R1 in this specification, however R 11 ~R 14 Each of them is not hydrogen, Z 11 ~Z 14 For explanations of each of these, please refer to the explanation of Z1 in this specification. * represents the bonding site with X5 in chemical formula 1. *' represents the bonding site with T1 in chemical formula 1.

[0095] Furthermore, according to other concrete examples, in the above chemical formula 1, n1 and n2 are each 1, and the ring CY2 is a group represented by the following chemical formula CY2A or the following chemical formula CY2B.

[0096] [ka]

[0097] With the above chemical formulas CY2A and CY2B, For descriptions of X2 and ring CY2, please refer to the respective sections in this specification. Y 21Y 23 Each of these is independently O, S, N, C, or Si. X2 and Y 21 The combination of X2 and Y 22 The combination of X2 and Y 23 The combination with, and Y 22 and Y 23 The bonds between them are chemical bonds, *' represents the bonding site with T1 in chemical formula 1. * represents the bonding site with M in the above chemical formula 1. * represents the bonding site with T2 in the above chemical formula 1.

[0098] Furthermore, according to other concrete examples, in the above chemical formula 1, n1 and n2 are each 1. [ka] The group represented by is one of the following chemical formulas CY2(1) to CY2(16).

[0099] [ka]

[0100] In the above chemical formulas CY2(1) to CY2(16), For a description of X2, please refer to the relevant sections in this specification. X 29 O, S, N-[(L2) b2 -(R2) c2 ], N(Z 24 ), C(R 29a )(R 29b ), or Si(R 29a )(R 29b ) and For explanations of L2, b2, R2, and c2, please refer to the relevant sections in this specification. Z 24 For further explanation, please refer to the explanation for Z2 in this specification. R 29a and R 29bFor explanations regarding each of these, please refer to the explanation regarding R2 in this specification. *' represents the bonding site with T1 in chemical formula 1. * represents the bonding site with M in chemical formula 1. * represents the bonding site with T2 in chemical formula 1.

[0101] Furthermore, according to other concrete examples, in the above chemical formula 1, n1 and n2 are each 1. [ka] The group represented by is one of the following chemical formulas: CY2-1 to CY2-16, and ZCY2-1 to ZCY2-19.

[0102] [ka]

[0103] [ka]

[0104] The above chemical formulas CY2-1 to CY2-16 and ZCY2-1 to ZCY2-19, For a description of X2, please refer to the relevant sections in this specification. X 29 O, S, N-[(L2) b2 -(R2) c2 ], C(R 29a )(R 29b ), or Si(R 29a )(R 29b ) and For explanations of L2, b2, R2, and c2, please refer to the relevant sections in this specification. Z 21 ~Z 24 For explanations of each of these, please refer to the explanation of Z2 in this specification. R 21 ~R23, R 29a and R 29bFor explanations of each of these, see the explanation of R2 in this specification, however R 21 ~R 23 Each of them is not hydrogen, *' represents the bonding site with T1 in chemical formula 1. * represents the bonding site with M in chemical formula 1. * represents the bonding site with T2 in chemical formula 1.

[0105] Furthermore, according to other concrete examples, in the above chemical formula 1, n2 and n3 are each 1. [ka] The group represented by is one of the following chemical formulas CY3(1) to CY3(15).

[0106] [ka]

[0107] The above chemical formulas CY3(1) to CY3(15) For a description of X3, please refer to the relevant sections of this specification. X 39 O, S, N(Z 39a ), C(R 39a )(R 39b ), or Si(R 39a )(R 39b ) and R 39a and R 39b For explanations regarding each of these, please refer to the explanation regarding R3 in this specification. * represents the bonding site with T2 in chemical formula 1. * represents the bonding site with M in chemical formula 1. *' represents the bonding site with T3 in chemical formula 1.

[0108] Furthermore, according to other concrete examples, in the above chemical formula 1, n2 and n3 are each 1. [ka] The group represented by is one of the following chemical formulas: CY3-1 to CY3-13, and ZCY3-1 to ZCY3-12.

[0109] [ka]

[0110] [ka]

[0111] The above chemical formulas CY3-1 to CY3-13, and the above chemical formulas ZCY3-1 to ZCY3-12, For a description of X3, please refer to the relevant sections of this specification. X 39 O, S, N-[(L3) b3 -(R3)c3], C(R 39a )(R 39b ), or Si(R 39a )(R 39b ) and For explanations of L3, b3, R3, and c3, please refer to the relevant sections in this specification. R 31 ~R 33 , R 39a and R 39b For explanations of each of these, see the explanation for R3 in this specification, however R 31 ~R 33 Each of them is not hydrogen, Z 31 ~Z 33 For explanations of each of these, please refer to the explanation of Z3 in this specification. * represents the bonding site with T2 in chemical formula 1. * represents the bonding site with M in chemical formula 1. *' represents the bonding site with T3 in chemical formula 1.

[0112] Furthermore, according to other concrete examples, in the above chemical formula 1, n3 is 1 and n4 is 0. [ka] The group represented by is one of the following chemical formulas CY4(1) to CY4(20).

[0113] [ka]

[0114] The above chemical formulas CY4(1) to CY4(20) For a description of X4, please refer to the relevant sections in this specification. X 49 O, S, N(R) 49a ), C(R 49a )(R 49b ), or Si(R 49a )(R 49b ) and R 49a and R 49b For explanations regarding each of these, please refer to the explanation regarding R4 in this specification. *' represents the bonding site with T3 in chemical formula 1. * represents the bonding site with M in chemical formula 1.

[0115] Furthermore, according to other concrete examples, in the above chemical formula 1, n3 is 1 and n4 is 0. [ka] The group represented by is one of the following chemical formulas: CY4-1 to CY4-16, and ZCY4-1 to ZCY4-32.

[0116] [ka]

[0117] [ka]

[0118] The above chemical formulas CY4-1 to CY4-16, and the above chemical formulas ZCY4-1 to ZCY4-32, For a description of X4, please refer to the relevant sections in this specification. R 41 ~R 44 For explanations relating to each of these, see the explanation relating to R4 in this specification, however, 41 ~R 44 Each of them is not hydrogen, Z 41 ~Z 44 For explanations of each of these, please refer to the explanation of Z4 in this specification. *' represents the bonding site with T3 in chemical formula 1. * represents the bonding site with M in chemical formula 1.

[0119] Furthermore, according to other concrete examples, organometallic compounds are represented by one of the following chemical formulas 1-1 to 1-4.

[0120] [ka]

[0121] In the above chemical formulas 1-1 to 1-4, For descriptions of M, X1 to X5, T2 and T3, please refer to the relevant sections in this specification. X 11 N, C(R 11 ), or C(Z 11 ) and X 12 N, C(R 12 ), or C(Z 12 ) and X 13 N, C(R 13 ), or C(Z 13 ) and X 14 N, C(R 14 ), or C(Z 14 ) and R 11 ~R 14For explanations regarding each of these, please refer to the explanation regarding R1 in this specification. Z 11 ~Z 14 For explanations of each of these, please refer to the explanation of Z1 in this specification. R 11 ~R 14 Two or more of these are optionally coupled to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 Forming a heterocyclic group, X 21 N, C(R 21 ), or C(Z 21 ) and X 22 N, C(R 22 ), or C(Z 22 ) and X 23 N, C(R 23 ), or C(Z 23 ) and X 29 O, S, N-[(L2) b2 -(R2) c2 ], C(R 29a )(R 29b ), or Si(R 29a )(R 29b ) and For explanations of L2, b2, R2, and c2, please refer to the relevant sections in this specification. R 21 ~R 23 , R 29a , and R 29b For explanations regarding each of these, please refer to the explanation regarding R2 in this specification. Z 21 ~Z 24 For explanations of each of these, please refer to the explanation of Z2 in this specification. R 21 ~R 23 Two or more of these are selectively coupled to each other, and at least one R 10a Substitute or non-substitute C5-C 30A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 Forming a heterocyclic group, X 31 N, C(R 31 ), or C(Z 31 ) and X 32 N, C(R 32 ), or C(Z 32 ) and X 33 N, C(R 33 ), or C(Z 33 ) and R 31 ~R 33 For explanations regarding each of these, please refer to the explanation regarding R3 in this specification. Z 31 ~Z 33 For explanations of each of these, please refer to the explanation of Z3 in this specification. R 31 ~R 33 Two or more of these are selectively coupled to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 Forming a heterocyclic group, X 41 N, C(R 41 ), or C(Z 41 ) and X 42 N, C(R 42 ), or C(Z 42 ) and X 43 N, C(R 43 ), or C(Z 43 ) and X 44 N, C(R 44 ), or C(Z 44 ) and R 41 ~R 44 For explanations regarding each of these, please refer to the explanation regarding R4 in this specification. Z 41 ~Z 44 For explanations of each of these, please refer to the explanation of Z4 in this specification. R 41 ~R 44 Two or more of these are selectively coupled to each other, and at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Substitute or non-substitute C1-C 30 Forming a heterocyclic group, Chemical formulas 1-1 and 1-2 above are, respectively, Z 11 ~Z 14 One of them, Z 21 ~Z 24 One of them, Z 31 ~Z 33 One of them, Z 41 ~Z 44 This includes one of the following, or any combination thereof: In the above chemical formulas 1 and 4, R 5a This is the group represented by the above chemical formula 51.

[0122] For example, organometallic compounds, i) The substance represented by the above chemical formula 1-1 or 1-2, wherein the above chemical formulas 1-1 and 1-2 satisfy at least one of the following conditions (1) to (3), ii) Represented by the above chemical formulas 1-3 or 1-4, or iii) A substance represented by the above chemical formula 1-3 or 1-4, wherein the above chemical formulas 1-3 and 1-4 satisfy at least one of the following conditions (1) to (3).

[0123] <Condition (1)> X22 is C(Z22) <Condition (2)> X32 is C(Z32) <Condition (3)> X43 is C(Z43).

[0124] Furthermore, according to other examples, in this specification, Z1 to Z4, Z 11 ~Z 14 , Z 21 ~Z 24 , Z31 ~Z 33 , and Z 41 ~Z 44 Each of these groups is independently represented by one of the chemical formulas 51-1 to 51-25 shown above.

[0125] Furthermore, according to other examples, in this specification, Z1 to Z4, Z 11 ~Z 14 , Z 21 ~Z 24 , Z 31 ~Z 33 , and Z 41 ~Z 44 Each of these groups is independently represented by one of the chemical formulas 51(1) to 51(19) above.

[0126] Furthermore, according to other concrete examples, the organometallic compound represented by the above chemical formula 1 satisfies at least one of the following conditions A to E.

[0127] <Condition A> In the above chemical formula 1, n1 is 1 and n4 is 0. [ka] The group represented by is one of the chemical formulas ZCY1-1 to ZCY1-32 shown above. <Condition B> In the above chemical formula 1, n1 and n2 are each 1. [ka] The group represented by is one of the chemical formulas ZCY2-1 to ZCY2-19 shown above. <Condition C> In the above chemical formula 1, n2 and n3 are each 1. [ka] The group represented by is one of the chemical formulas ZCY3-1 to ZCY3-12 shown above. <Condition D> In the above chemical formula 1, n3 is 1 and n4 is 0. [ka] The group represented by is one of the chemical formulas ZCY4-1 to ZCY4-32 shown above. <Condition abnormal> In the above chemical formula 1, n3 is 1, and T3 is *-N(R 5a )-*' and R 5a This is the group represented by the above chemical formula 51.

[0128] Furthermore, other examples show that the organometallic compound represented by the above chemical formula 1 emits green light.

[0129] Furthermore, according to other concrete examples, the organometallic compound represented by the above chemical formula 1 is one of the following compounds 1 to 750.

[0130] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka] [ka]

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[0131] The organometallic compound represented by Chemical Formula 1 satisfies at least one of <Condition 1> and <Condition 2> as described herein. That is, the organometallic compound represented by Chemical Formula 1 contains at least one group represented by Chemical Formula 51 as a substituent. As a result, the organometallic compound represented by Chemical Formula 1 has improved planarity and orientation characteristics, and the luminous efficiency and / or lifetime of electronic devices employing the organometallic compound represented by Chemical Formula 1, such as organic light-emitting devices, are improved.

[0132] The HOMO (highest occupied molecular orbital) energy level, LUMO (lowest unoccupied molecular orbital) energy level, and T1 energy level of some organometallic compounds represented by the above chemical formula 1 were evaluated using the Gaussian09 program, which involves molecular structure optimization based on density functional theory (DFT) using B3LYP. The results are shown in Table 1 below.

[0133] [Table 1]

[0134] From Table 1 above, it can be confirmed that the organometallic compound represented by chemical formula 1 has electrical properties suitable for use as a dopant in electronic devices, such as organic light-emitting devices.

[0135] The method for synthesizing the organometallic compound represented by the above chemical formula 1 will be recognizable to those skilled in the art by referring to the synthesis examples described later.

[0136] Therefore, the organometallic compound represented by the above chemical formula 1 is suitable for use as a dopant for the light-emitting layer in the organic layer of an organic light-emitting device, for example, in the organic layer. In other aspects, an organic light-emitting device is provided having a first electrode, a second electrode, and an organic layer disposed between the first electrode and the second electrode and including a light-emitting layer, wherein the organic layer contains at least one organometallic compound represented by the above chemical formula 1.

[0137] By comprising an organic light-emitting element containing an organometallic compound represented by the above-described chemical formula 1, the organic light-emitting element can have high external quantum efficiency and high lifetime characteristics.

[0138] The organometallic compound represented by chemical formula 1 is used between a pair of electrodes in an organic light-emitting device. For example, the organometallic compound represented by chemical formula 1 is included in the light-emitting layer. Here, the organometallic compound acts as a dopant, and the light-emitting layer further contains a host (i.e., the content of the organometallic compound represented by chemical formula 1 is less than the content of the host). The light-emitting layer emits, for example, green light or blue light.

[0139] 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, or two or more different organometallic compounds belonging to the category of chemical formula 1."

[0140] For example, the organic layer contains only compound 1 as an organometallic compound. In this case, compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer contains both compound 1 and compound 2 as organometallic compounds. Here, compound 1 and compound 2 are present in the same layer (for example, both compound 1 and compound 2 are present in the light-emitting layer).

[0141] The first electrode is an anode, which is a hole injection electrode, and the second electrode is a cathode, which is an electron injection electrode, or the first electrode is a cathode, which is an electron injection electrode, and the second electrode is an anode, which is a hole injection electrode.

[0142] For example, in an organic light-emitting device, the first electrode is an anode, the second electrode is a cathode, and the organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode. The hole transport region includes a hole injection layer, an electron blocking layer, a buffer layer, or any combination thereof, and the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0143] In this specification, "organic layer" is a term that refers to one and / or more layers arranged between the first electrode and the second electrode in an organic light-emitting device. The "organic layer" includes not only organic compounds but also organometallic complexes containing metals.

[0144] Figure 1 schematically shows a cross-sectional view of an organic light-emitting element 10 according to one embodiment of the present invention. The structure and manufacturing method of an organic light-emitting element according to one embodiment of the present invention will be described below with reference to Figure 1. The organic light-emitting element 10 has a structure in which a first electrode 11, an organic layer 15, and a second electrode 19 are stacked in order.

[0145] A substrate is additionally placed below the first electrode 11 or above the second electrode 19. While a substrate commonly used in organic light-emitting devices can be used, a glass substrate or a transparent plastic substrate with superior mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and water resistance is preferred.

[0146] The first electrode 11 is formed, for example, by providing the material for the first electrode on the upper part of the substrate using a vapor deposition method or a sputtering method. The first electrode 11 is an anode. The material for the first electrode includes a material having a high work function so that hole injection is easy. The first electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the material for the first electrode, indium tin oxide (ITO), indium zinc oxide (IZO), tin oxide (SnO2), zinc oxide (ZnO), etc. can be used. Alternatively, metals such as magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mgn), and magnesium-silver (Mg-Ag) can be used.

[0147] The first electrode 11 has a single-layer structure or a multilayer structure containing two or more layers. For example, the first electrode 11 has a three-layer structure of ITO / Ag / ITO.

[0148] An organic layer 15 is placed on top of the first electrode 11.

[0149] The organic layer 15 includes a hole transport region, an emissive layer, and an electron transport region.

[0150] The hole transport region is located between the first electrode 11 and the light-emitting layer.

[0151] The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof.

[0152] The hole transport region may consist only of a hole injection layer or only of a hole transport layer. Alternatively, the hole transport region may have a structure of hole injection layer / hole transport layer or hole injection layer / hole transport layer / electron blocking layer stacked sequentially from the first electrode 11.

[0153] If the hole transport region includes a hole injection layer, the hole injection layer is formed on top of the first electrode 11 using a variety of methods such as vacuum deposition, spin coating, casting, and LB (Langmuir-Blodgett) method.

[0154] When forming a hole injection layer by vacuum deposition, the deposition conditions vary depending on the compound used as the hole injection layer material, the desired structure of the hole injection layer, and its thermal properties. For example, the deposition temperature is approximately 100 to 500°C, and the vacuum level is approximately 10°C. -8 ~about 10 -3 Torr is selected from a range of approximately 0.01 to 100 Å / sec.

[0155] When forming a hole injection layer by spin coating, the coating conditions vary depending on the compound used as the hole injection layer material, the desired structure of the hole injection layer, and its thermal properties. The coating is performed at a speed of approximately 2,000 rpm to 5,000 rpm, and the heat treatment temperature for solvent removal after coating is selected from a temperature range of approximately 80°C to 200°C.

[0156] The formation conditions for the hole transport layer and electron blocking layer refer to the formation conditions for the hole injection layer.

[0157] The hole transport region includes, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated-NPB, TAPC, HMTPD, 4,4',4”-tris(N-carbazolyl)triphenylamine) (TCTA), polyaniline / dodecylbenzenesulfonic acid) (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrenesulfonate) (PEDOT / PSS), polyaniline / camphorsulfonic acid (Pani / CSA), polyaniline / poly(4-styrenesulfonate) (PANI / PSS), compounds represented by the following chemical formula 201, compounds represented by the following chemical formula 202, or any combination thereof.

[0158] [ka]

[0159] [ka] [ka]

[0160] In the above chemical formula 201, Ar 101 and Ar 102 These are, independently of each other, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10 Heterocycloalkenyl group, C6-C 60Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 The group is a heteroaryl group, a monovalent non-aromatic condensed polycyclic group, a monovalent non-aromatic heterocondensed polycyclic group, or any combination thereof, and is substituted or unsubstituted with a phenylene group, pentarenylene group, indenylene group, naphthylene group, azurenylene group, heptarenylene group, acenaphthylene group, fluorenylene group, phenalenylene group, phenantrenylene group, anthracenylene group, fluoranthenylene group, triphenylenylene group, pyrenylene group, chrysenyrenylene group, naphthasenylene group, picenylene group, perillenylene group, or pentasenylene group.

[0161] In the above chemical formula 201, xa and xb are independent integers between 0 and 5, or 0, 1, or 2. For example, xa is 1 and xb is 0.

[0162] In the above chemical formulas 201 and 202, R 101 ~R 108 , R 111 ~R 119 , and R 121 ~R 124 Each of them operates independently. Hydrogen, deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl groups (e.g., methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, etc.), or C1-C 10 Alkoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group, etc.); Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, or any combination thereof, C1-C 10 Alkyl alkyl group, or C1-C 10Alkoxy group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 10 Alkyl alkyl group, C1-C 10 A phenyl group, naphthyl group, anthracenyl group, fluorenyl group, or pyrenyl group, substituted or unsubstituted with an alkoxy group or any combination thereof;

[0163] In the above chemical formula 201, R 109 This includes deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Alkyl alkyl group, C1-C 20 A phenyl group, naphthyl group, anthracenyl group, or pyridinyl group, which is substituted or unsubstituted with an alkoxy group, a phenyl group, anthracenyl group, or pyridinyl group, or any combination thereof.

[0164] According to one example, the compound represented by the above chemical formula 201 is represented by the following chemical formula 201A.

[0165] [ka]

[0166] In the above chemical formula 201A, R 101 , R 111 , R 112 , and R 109 For a detailed explanation, please refer to the section mentioned above.

[0167] For example, the hole transport region includes one of the following compounds HT1 to HT20, or any combination thereof.

[0168] [ka] [ka]

[0169] The thickness of the hole transport region is approximately 100 Å to 10,000 Å, for example, approximately 100 Å to 1,000 Å. If the hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof, the thickness of the hole injection layer is approximately 100 Å to 10,000 Å, for example, approximately 100 Å to 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to 2,000 Å, for example, approximately 100 Å to 1,500 Å. When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer satisfy the above ranges, satisfactory hole transport characteristics can be obtained without a substantial increase in the driving voltage.

[0170] The hole transport region further includes charge-generating materials in addition to the materials described above, for the purpose of improving conductivity. The charge-generating materials are uniformly or non-uniformly dispersed within the hole transport region.

[0171] Charge-generating substances are, for example, p-type dopants. P-type dopants are quinone derivatives, metal oxides, cyano group-containing compounds, or any combination thereof. For example, p-type dopants are quinone derivatives such as tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetrafluoro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), and F6-TCNNQ; metal oxides such as tungsten oxide and molybdenum oxide; cyano group-containing compounds such as the compound HT-D1 below; or any combination thereof.

[0172] [ka]

[0173] The hole transport region further includes a buffer layer.

[0174] The buffer layer compensates for the optical resonance distance caused by the wavelength of light emitted from the light-emitting layer, thereby increasing efficiency.

[0175] On the other hand, if the hole transport region includes an electron blocking layer, the electron blocking layer material includes the material used in the hole transport region as described above, the host material described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, the mCP described later, compound H-H1, or any combination thereof is used as the electron blocking layer material.

[0176] An emissive layer is formed above the hole transport region using methods such as vacuum deposition, spin coating, casting, or LB. When forming the emissive layer by vacuum deposition or spin coating, the deposition and coating conditions vary depending on the compound used, and are generally selected from a range of conditions that are approximately the same as those used for forming the hole injection layer.

[0177] The light-emitting layer comprises a host and a dopant, the dopant comprising an organometallic compound represented by chemical formula 1 as described herein.

[0178] The host contains the following TPBi, TBADN, ADN ("DNA"), CBP, CDBP, TCP, mCP, compound H50, compound H51, compound H52, compound H-H1, compound H-H2, or any combination thereof.

[0179] [ka]

[0180] When an organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer is patterned with a red light-emitting layer, a green light-emitting layer, and / or a blue light-emitting layer. Alternatively, the light-emitting layer can 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, and various other modifications are possible.

[0181] When the luminescent layer contains a host and a dopant, the dopant content is generally selected from a range of approximately 0.01 to approximately 20 parts by weight, based on approximately 100 parts by weight of the host.

[0182] The thickness of the light-emitting layer is approximately 100 Å to 1,000 Å, for example, approximately 200 Å to 600 Å. When the thickness of the light-emitting layer satisfies the above range, excellent light emission characteristics can be achieved without a substantial increase in the driving voltage.

[0183] Next, an electron transport region is placed above the light-emitting layer.

[0184] The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

[0185] For example, the electron transport region has a hole blocking layer / electron transport layer / electron injection layer structure, or an electron transport layer / electron injection layer structure. The electron transport layer has a single-layer structure or a multilayer structure containing two or more different materials.

[0186] The formation conditions for the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region refer to the formation conditions for the hole injection layer.

[0187] If the electron transport region includes a hole blocking layer, the hole blocking layer includes, for example, BCP, Bphen, BAlq, or any combination thereof.

[0188] [ka]

[0189] The thickness of the hole blocking layer is approximately 20 Å to 1,000 Å, for example, approximately 30 Å to 600 Å. When the thickness of the hole blocking layer satisfies the above range, excellent hole blocking characteristics can be obtained without a substantial increase in the driving voltage.

[0190] The electron transport layer includes the above-mentioned BCP, Bphen, TPBi, and the following Alq3, BAlq, TAZ, NTAZ, or any combination thereof.

[0191] [ka]

[0192] Alternatively, the electron transport layer may contain one of the following compounds ET1 to ET25, or any combination thereof.

[0193] [ka] [ka]

[0194] The thickness of the electron transport layer is approximately 100 Å to 1,000 Å, for example, approximately 150 Å to 500 Å. When the thickness of the electron transport layer satisfies the above range, satisfactory electron transport characteristics can be obtained without a substantial increase in the driving voltage.

[0195] The electron transport layer further contains metal-containing materials in addition to the materials mentioned above.

[0196] The metal-containing substance includes Li complexes. Li complexes include, for example, the following compounds ET-D1 or ET-D2.

[0197] [ka]

[0198] Furthermore, the electron transport region includes an electron injection layer that facilitates the injection of electrons from the second electrode 19.

[0199] The electron injection layer includes LiF, NaCl, CsF, Li2O, BaO, compound ET-D1, compound ET-D2, or any combination thereof.

[0200] The thickness of the electron injection layer is approximately 1 Å to 100 Å, for example, approximately 3 Å to 90 Å. When the thickness of the electron injection layer satisfies the above range, satisfactory electron injection characteristics can be obtained without a substantial increase in the driving voltage.

[0201] A second electrode 19 is placed on top of the organic layer 15. The second electrode 19 is the cathode. As the material for the second electrode 19, a metal, alloy, electrically conductive compound with a relatively low work function, or any combination thereof can be used. Specific examples include lithium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), and magnesium-silver (Mg-Ag) used as materials for forming the second electrode 19. Alternatively, various modifications are possible, such as using ITO or IZO to form a transmissive second electrode 19 in order to obtain a front-facing light-emitting element.

[0202] The above describes organic light-emitting devices with reference to Figure 1, but they are not limited to those described above.

[0203] Further, from another perspective, organic light-emitting elements are included in electronic devices. Therefore, electronic devices containing organic light-emitting elements are provided. Electronic devices include, for example, displays, lighting, sensors, and the like.

[0204] Furthermore, from another perspective, a diagnostic composition is provided that contains one or more organometallic compounds represented by the above chemical formula 1.

[0205] Since the organometallic compound represented by the above chemical formula 1 can provide high luminescence efficiency, a diagnostic composition containing the organometallic compound can have high diagnostic efficiency.

[0206] Diagnostic compositions are used in a wide variety of applications, including various diagnostic kits, diagnostic reagents, biosensors, and biomarkers.

[0207] In this specification, C1-C60 Alkyl groups refer to linear or branched saturated aliphatic hydrocarbon monovalent groups having 1 to 60 carbon atoms, C1-C 60 The alkylene group is C1-C 60 This refers to a divalent group that has the same structure as an alkyl group.

[0208] In this specification, C1-C 60 Alkyl alkyl group, C1-C 20 Alkyl alkyl groups, and / or C1-C 10 Examples of alkyl groups include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, n-hexyl group, isohexyl group, sec-hexyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, tert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or any combination thereof. This includes mixed-substituted or unsubstituted methyl groups, ethyl groups, n-propyl groups, isopropyl groups, n-butyl groups, sec-butyl groups, isobutyl groups, tert-butyl groups, n-pentyl groups, tert-pentyl groups, neopentyl groups, isopentyl groups, sec-pentyl groups, 3-pentyl groups, sec-isopentyl groups, n-hexyl groups, isohexyl groups, sec-hexyl groups, tert-hexyl groups, n-heptyl groups, isoheptyl groups, sec-heptyl groups, tert-heptyl groups, n-octyl groups, isooctyl groups, sec-octyl groups, tert-octyl groups, n-nonyl groups, isononyl groups, sec-nonyl groups, tert-nonyl groups, n-decyl groups, isodecyl groups, sec-decyl groups, or tert-decyl groups. For example, the above chemical formula 9-33 is a branched C6 alkyl group and can be seen as a tert-butyl group substituted with two methyl groups.

[0209] In this specification, C1-C60 The alkoxy group is -OA 101 (Here, A 101 C1-C 60 This refers to a monovalent group having the chemical formula of an alkyl group, and specific examples include the methoxy group, ethoxy group, propoxy group, butoxy group, or pentoxy group.

[0210] In this specification, C1-C 60 The alkylthio group is -SA 101 (Here, A 101 C1-C 60 This refers to a monovalent group having the chemical formula (which is an alkyl group).

[0211] In this specification, C2-C 60 The alkenyl group is C2-C 60 A C2-C group has a structure containing one or more carbon-carbon double bonds in the middle or terminal of an alkyl group, and specific examples include ethenyl, propenyl, and butenyl groups. In this specification, C2-C 60 The alkenylene group is C2-C 60 This refers to a divalent group that has the same structure as an alkenyl group.

[0212] In this specification, C2-C 60 The alkynyl group is C2-C 60 A C2-C alkyl group has a structure containing one or more carbon-carbon triple bonds in the middle or terminal, and specific examples include an ethynyl group, a propynyl group, and the like. In this specification, C2-C 60 The alkynylene group is C2-C 60 This refers to a divalent group that has the same structure as an alkynyl group.

[0213] In this specification, C3-C 10 Cycloalkyl groups are C3-C 10 This refers to a monovalent saturated hydrocarbon cyclic group, C3-C 10 The cycloalkylene group is C3-C 10 This refers to a divalent group having the same structure as a cycloalkyl group.

[0214] In this specification, C3-C 10 Examples of cycloalkyl groups include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantanyl, norbornanyl (or bicyclo[2.2.1]heptyl), bicyclo[1.1.1]pentyl, bicyclo[2.1.1]hexyl, and bicyclo[2.2.2]octyl.

[0215] In this specification, C1-C 10 A heterocycloalkyl group is a C1-C alkyl group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 10 This refers to a monovalent monocyclic group, C1-C 10 The heterocycloalkylene group is C1-C 10 This refers to a divalent group having the same structure as a heterocycloalkyl group.

[0216] In this specification, C1-C 10 Examples of heterocycloalkyl groups include siloranil, silinanil, tetrahydrofuranil, tetrahydro-2H-pyranil, and tetrahydrothiophenyl groups.

[0217] In this specification, C3-C 10 The cycloalkenyl group is C3-C 10 A monovalent cyclic group is a group that has at least one carbon-carbon double bond within the ring but does not possess aromaticity. Specific examples include the cyclopentenyl group, cyclohexenyl group, and cycloheptenyl group. In this specification, C3-C 10 The cycloalkenylene group is C3-C 10 This refers to a divalent group that has the same structure as a cycloalkenyl group.

[0218] In this specification, C1-C 10 A heterocycloalkenyl group is a C1-C group containing at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom. 10It is a monovalent monocyclic group and has at least one double bond within the ring. C1-C 10 Specific examples of heterocycloalkenyl groups include the 2,3-dihydrofuranyl group and the 2,3-dihydrothiophenyl group. In this specification, C1-C 10 The heterocycloalkenylene group is C1-C 10 This refers to a divalent group that has the same structure as a heterocycloalkenyl group.

[0219] In this specification, C6-C 60 The aryl group is C6-C 60 This refers to a monovalent group having a carbon-ring aromatic system, C6-C 60 The arylene group is C6-C 60 This refers to a divalent group having a carbon-ring aromatic system. C6-C 60 Specific examples of aryl groups include phenyl, naphthyl, anthracenyl, phenantrenyl, pyrenyl, and chrysenyl groups. C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings are fused to each other.

[0220] In this specification, C7-C 60 The alkylaryl group has at least one C1-C 60 C6-C substituted with alkyl group 60 It means an aryl group.

[0221] In this specification, C1-C 60 The heteroaryl group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and C1-C 60 This refers to a monovalent group having a cyclic aromatic system, C1-C 60 The heteroarylene group contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and C1-C 60 This refers to a divalent group having a cyclic aromatic system. C1-C 60Specific examples of heteroaryl groups include pyridinyl, pyrimidinyl, pyrazinyl, pyridadinyl, triazinyl, quinolinyl, and isoquinolinyl groups. C1-C 60 Heteroaryl group and C1-C 60 If a heteroarylene group contains two or more rings, the two or more rings are fused to each other.

[0222] In this specification, C2-C 60 The alkylheteroaryl group has at least one C1-C 60 C1-C substituted with alkyl group 60 It means a heteroaryl group.

[0223] In this specification, C6-C 60 The aryloxy group is -OA 102 (Here, A 102 C6-C 60 (It is an aryl group) and C6-C 60 The arylthio group is -SA 103 (Here, A 103 C6-C 60 (It is an aryl group) and C1-C 60 The alkylthio group is -SA 104 (Here, A 104 C1-C 60 It indicates that it is an alkyl group.

[0224] In this specification, a monovalent non-aromatic condensed polycyclic group means a monovalent group (for example, having 8 to 60 carbon atoms) in which two or more rings are fused together, containing only carbon as the ring-forming atom, and the entire molecule is non-aromatic. Specific examples of monovalent non-aromatic condensed polycyclic groups include the fluorenyl group. In this specification, a divalent non-aromatic condensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic condensed polycyclic group.

[0225] In this specification, a monovalent non-aromatic heterocondensed polycyclic group means a monovalent group (for example, having 1 to 60 carbon atoms) in which two or more rings are condensed together, and in addition to carbon, it contains at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as a ring-forming atom, and the entire molecule is non-aromatic. A monovalent non-aromatic heterocondensed polycyclic group includes a carbazolyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group means a divalent group having the same structure as a monovalent non-aromatic heterocondensed polycyclic group.

[0226] In this specification, C5-C 30 A carbocyclic group is a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. C5-C 30 A carbocyclic group is a monocyclic or polycyclic group. In this specification, "(at least one R 10a (Substituted or not substituted) C5-C 30 A "carbon ring group" is, for example, (at least one R 10a This includes adamantane groups (substituted or unsubstituted), norbornene groups, bicyclo[1.1.1]pentane groups, bicyclo[2.1.1]hexane groups, bicyclo[2.2.1]heptane groups (norbornane groups), bicyclo[2.2.2]octane groups, cyclopentane groups, cyclohexane groups, cyclohexene groups, benzene groups, naphthalene groups, anthracene groups, phenanthrene groups, triphenylene groups, pyrene groups, chrysene groups, 1,2,3,4-tetrahydronaphthalene groups, cyclopentadiene groups, fluorene groups, etc.

[0227] In this specification, C1-C 30 A heterocyclic group is a saturated or unsaturated cyclic group having, in addition to 1 to 30 carbon atoms, at least one heteroatom selected from N, O, P, Si, S, Se, Ge, and B as ring-forming atoms. C1-C 30 A heterocyclic group is either a monocyclic or polycyclic group. (At least one R 10a (Substituted or not substituted) C1-C 30 A heterocyclic group is, for example, (at least one R 10aThiophene group (substituted or unsubstituted), furan group, pyrrole group, silole group, borol group, phosphole group, selenofen group, gelmol group, benzothiophene group, benzofuran group, indole group, benzosilole group, benzobolol group, benzophosphole group, benzoselenophene group, benzogermol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilole group, dibenzobolol group, dibenzophosphole group, dibenzoselenophene group, dibenzogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilole group, azabenzobolol group, azabenzophosphole group, azabenzoselenophene group, azabenzogermol group, azadibenzothiophene group, azadibenzofuran group, azacarb Zole group, azafluorene group, azadibenzosilol group, azadibenzobolol group, azadibenzophosphole group, azadibenzoselenophene group, azadibenzogermole group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, This includes phenanthroline groups, pyrazole groups, imidazole groups, triazole groups, oxazole groups, isoxazole groups, thiazole groups, isothiazole groups, oxadiazole groups, thiadiazole groups, benzopyrazole groups, benzimidazole groups, benzoxazole groups, benzothiazole groups, benzoxadiazole groups, benzothiadiazole groups, 5,6,7,8-tetrahydroisoquinoline groups, 5,6,7,8-tetrahydroquinoline groups, and the like.

[0228] As another example, in this specification, "C5-C 30 "Carbon ring group" and "C1-C 30Examples of "heterocyclic groups" include i) a first ring, ii) a second ring, iii) a fused ring formed by the fusion of two or more first rings, iv) a fused ring formed by the fusion of two or more second rings, or v) a fused ring formed by the fusion of one or more first rings and one or more second rings. The first ring is a cyclopentane group, cyclopentene group, furan group, thiophene group, pyrrole group, silole group, borol group, phosphole group, germole group, selenofen group, oxazole group, oxadiazole group, oxatriazole group, thiazole group, thiadiazole group, thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazole group, or azasilol group. The second ring is an adamantane group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.

[0229] In this specification, "fluorinated C1-C 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 Cycloalkyl group, C1-C fluoride 10 The heterocycloalkyl group and the phenyl fluoride group are each substituted with at least one fluoro group (-F), C1-C 60 Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 This refers to heterocycloalkyl groups and phenyl groups. For example, "C1 alkyl fluoride (i.e., methyl fluoride group)" includes -CF3, -CF2H, and -CFH2. 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 Cycloalkyl group, C1-C fluoride 10 "Heterocycloalkyl group" or "fluorinated phenyl group" is i) a fully fluorinated C1-C group in which all hydrogen atoms in each group are replaced by fluoro groups. 60Alkyl alkyl groups (or fully fluorinated C1-C 20 Alkyl alkyl groups, etc.), fully fluorinated C3-C 10 Cycloalkyl groups, fully fluorinated C1-C 10 ii) a heterocycloalkyl group, or a fully fluorinated phenyl group, or ii) a partially fluorinated C1-C group in which not all hydrogen atoms in each group are substituted with fluoro groups. 60 Alkyl group (or partially fluorinated C1-C 20 (Alkyl alkyl groups, etc.), partially fluorinated C3-C 10 Cycloalkyl groups, partially fluorinated C1-C 10 It is a heterocycloalkyl group, or partly a phenyl fluoride group.

[0230] In this specification, "deuterated C1-C 60 Alkyl group (or deuterated C1-C 20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 The heterocycloalkyl group and the deuterated phenyl group are each C1-C groups substituted with at least one deuterium atom. 60 Alkyl group (or C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 This refers to heterocycloalkyl groups and phenyl groups. For example, "deuterated C1 alkyl group (i.e., deuterated methyl group)" includes -CD3, -CD2H, and -CDH2, and "deuterated C3-C 10 For an example of a "cycloalkyl group," see, for instance, chemical formula 10-501 above. 60 Alkyl group (or deuterated C1-C 20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 "Heterocycloalkyl group" or "deuterated phenyl group" is a fully deuterated C1-C group in which all hydrogen atoms in each group are replaced with deuterium. 60 Alkyl group (or fully deuterated C1-C20 alkyl group, etc.), fully deuterated C3-C 10 cycloalkyl group, fully deuterated C1-C 10 heterocycloalkyl group, or fully deuterated phenyl group, or ii) not all hydrogen atoms contained in each group are substituted with deuterium, but partially deuterated C1-C 60 alkyl group (or partially deuterated C1-C 20 alkyl group, etc.), partially deuterated C3-C 10 cycloalkyl group, partially deuterated C1-C 10 heterocycloalkyl group, or partially deuterated phenyl group.

[0231] As used herein, "((C1-C 20 alkyl) "X" group" refers to an "X" group substituted with at least one C1-C 20 alkyl group. For example, as used herein, "(C1-C 20 alkyl)C3-C 10 cycloalkyl group" refers to a C3-C 20 cycloalkyl group substituted with at least one C1-C 10 alkyl group, and "(C1-C 20 alkyl)phenyl group" refers to a phenyl group substituted with at least one C1-C 20 alkyl group. An example of the (C1 alkyl)phenyl group is a toluyl group.

[0232] In this specification, "azaindole group, azabenzoborol group, azabenzophosphole group, azaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, azadibenzoborol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group, azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxide group" are, respectively, This refers to heterocycles that share the same backbone as "indole group, benzoborol group, benzophosphole group, indene group, benzosilol group, benzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoborol group, dibenzophosphole group, fluorene group, dibenzosilol group, dibenzogermol group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, and dibenzothiophene 5,5-dioxide group," but in which at least one of the carbon atoms forming the ring is substituted with nitrogen.

[0233] Substituted C5-C 30 Carbocyclic group, substituted C2-C 30 Heterocyclic group, substituted C1-C 60 Alkyl alkyl group, substituted C2-C 60 Alkenyl group, substituted C2-C 60 Alkynyl group, substituted C1-C 60 Alkoxy group, substituted C1-C 60 Alkylthio group, substituted C1-C 60 Alkylthio group, substituted C3-C 10 Cycloalkyl groups, substituted C1-C 10 Heterocycloalkyl groups, substituted C3-C 10 Cycloalkenyl group, substituted C1-C 10 Heterocycloalkenyl group, substituted C6-C 60 Aryl group, substituted C7-C60 Alkylaryl group, substituted C6-C 60 Aryloxy group, substituted C6-C 60 Arylthio group, substituted C1-C 60 heteroaryl group, substituted C2-C 60 The alkyl heteroaryl group, the substituted monovalent non-aromatic condensed polycyclic group, and the substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group are each independently: Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkynyl group C1-C 60 Alkoxy group, or C1-C 60 Alkylthio group; Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group, -N(Q 11 )(Q 12 ), -Si(Q 13 )(Q 14 )(Q 15 ), -B(Q 16 )(Q17 ), -P(=O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof substituted, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, or C1-C 60 alkylthio group; deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydrazine group, hydrazone group, carboxylic acid group or a salt thereof, sulfonic acid group or a salt thereof, phosphoric acid group or a salt thereof, C1-C 60 alkyl group, C2-C 60 alkenyl group, C2-C 60 alkynyl group, C1-C 60 alkoxy group, C1-C 60 alkylthio group, C3-C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloalkenyl group, C1-C 10 heterocycloalkenyl group, C6-C 60 aryl group, C7-C 60 alkylaryl group, C6-C 60 aryloxy group, C6-C 60 arylthio group, C1-C 60 heteroaryl group, C2-C 60 alkylheteroaryl group, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic hetero-fused polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q 24 )(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P(Q 28 )(Q 29), or any combination thereof, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic heterocondensed polycyclic group; -N(Q 31 )(Q 32 ), -Si(Q 33 )(Q 34 )(Q 35 ), -B(Q 36 )(Q 37 ), -P(=O)(Q 38 )(Q 39 ), or -P(Q 38 )(Q 39 ); or Any combination of those;

[0234] In this specification, Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 , and Q 31 ~Q 39 These are, independently, hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; sulfonic acid group or its salt; phosphate group or its salt; deuterium, C1-C 60 Alkyl alkyl group, C6-C 60 A C1-C group substituted or unsubstituted with an aryl group, or any combination thereof. 60 Alkyl alkyl group; C2-C 60 Alkenyl group; C2-C 60 Alkynyl group; C1-C 60 Alkoxy group; C1-C60 Alkylthio group; C3-C 10 Cycloalkyl group; C1-C 10 Heterocycloalkyl groups; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl alkyl group, C6-C 60 C6-C substituted or unsubstituted with an aryl group, or any combination thereof. 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 It is a heteroaryl group; a monovalent non-aromatic condensed polycyclic group; or a monovalent non-aromatic heterocondensed polycyclic group.

[0235] For example, in this specification, Q1 to Q9, Q 11 ~Q 19 Q 21 ~Q 29 , and Q 31 ~Q 39 Each of them operates independently. -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or Deuterium, C1-C 10 n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl group, phenyl group, biphenyl group, or naphthyl group, substituted or unsubstituted with alkyl groups, phenyl groups, or any combination thereof;

[0236] The following describes a compound and an organic light-emitting element according to one embodiment of the present invention, with reference to synthesis examples and embodiments. However, the present invention is not limited to the following synthesis examples and embodiments. In the following synthesis examples, the expression "'B' was used instead of 'A'" means that the amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0237] [Examples]

[0238] ≪Synthesis Example 1 (Compound 317)≫

[0239] [ka]

[0240] Compound 317-1 (7.9 g, 11.0 mmol), K2PtCl4 (5.5 g, 13.2 mmol), and 100 mL of acetic acid were mixed and the reaction was carried out under reflux stirring for 18 hours, after which the temperature was lowered to room temperature. The resulting solid was filtered and column chromatography was performed using methylene chloride (MC) and hexane to obtain 4.2 g of compound 317 (42% yield). HRMS (MALDI) calcd for C 50 H 49 D2N3OPt:m / z 906.3805 found:906.3811

[0241] ≪Synthesis Example 2 (Compound 351)≫

[0242] [ka]

[0243] Compound 351-1 (7.9 g, 11.1 mmol), K2PtCl4 (5.5 g, 13.3 mmol), and 100 mL of acetic acid were mixed and the reaction was carried out under reflux stirring for 18 hours, after which the temperature was lowered to room temperature. The resulting solid was filtered, and column chromatography was performed using methylene chloride and hexane to obtain 3.8 g of compound 351 (38% yield). HRMS (MALDI) calcd for C 51 H 37 N3OPt:m / z 902.2584 found:902.2589

[0244] ≪Synthesis Example 3 (Compound 592)≫

[0245] [ka]

[0246] Compound 592-1 (7.9 g, 11.1 mmol), K2PtCl4 (5.5 g, 13.3 mmol), and 100 mL of acetic acid were mixed and the reaction was carried out under reflux stirring for 18 hours, after which the temperature was lowered to room temperature. The resulting solid was filtered, and column chromatography was performed using methylene chloride and hexane to obtain 3.1 g of compound 592 (31% yield). HRMS (MALDI) calcd for C 50 H 46 DN3OPt:m / z 901.3430 found:901.3420

[0247] ≪Synthesis Example 4 (Compound 741)≫

[0248] [ka]

[0249] Compound 741-1 (3.9 g, 5.9 mmol), K2PtCl4 (3.0 g, 7.1 mmol), and 50 mL of acetic acid were mixed and the reaction was carried out under reflux stirring for 18 hours, after which the temperature was lowered to room temperature. The resulting solid was filtered, and column chromatography was performed using methylene chloride and hexane to obtain 2.1 g of compound 741 (42% yield). HRMS (MALDI) calcd for C 47 H 40 N2OPt:m / z 843.2788 found:843.2795

[0250] ≪Synthesis example A (compound A)≫

[0251] [ka]

[0252] Except for using compound A-1 instead of compound 317-1, the same method as in Synthesis Example 1 was used to obtain 0.5 g of compound A (40% yield). HRMS (MALDI) calcd for C 43 H 45 N3OPt:m / z 814.3210 found:814.3205

[0253] ≪Synthesis example B (compound B)≫

[0254] [ka]

[0255] Except for using compound B-1 instead of compound 351-1, the same method as in Synthesis Example 2 was used to obtain 0.4 g of compound B (36% yield). HRMS (MALDI) calcd for C 42 H 27 N3OPt:m / z 784.1802 found:784.1796

[0256] ≪Synthesis example C (compound C)≫

[0257] [ka]

[0258] Except for using compound C-1 instead of compound 592-1, the same method as in Synthesis Example 3 was used to obtain 0.6 g of compound C (45% yield). HRMS (MALDI) calcd for C 42 H39 N3OPt:m / z 796.2741 found:796.2744

[0259] ≪Synthesis example D (compound D)≫

[0260] [ka]

[0261] Except for using compound D-1 instead of compound 741-1, the same method as in Synthesis Example 4 was used to obtain 0.2 g of compound D (22% yield). HRMS (MALDI) calcd for C 38 H30N2OPt:m / z 725.2006 found:725.2001

[0262] Example 1

[0263] As an anode, a glass substrate patterned with ITO was cut to a size of 50mm x 50mm x 0.5mm, ultrasonically cleaned for 5 minutes each using isopropyl alcohol and pure water, then cleaned by irradiating with ultraviolet light for 30 minutes to expose it to ozone, and finally placed in a vacuum deposition apparatus.

[0264] On the anode, the compounds HT3 and F6-TCNNQ were vacuum co-deposited in a weight ratio of 98:2 to form a 100 Å thick hole injection layer. On top of the hole injection layer, the compound HT3 was vacuum-deposited to form a 1,350 Å thick hole transport layer. On top of the hole transport layer, the compound H-H1 was vacuum-deposited to form a 300 Å thick electron blocking layer.

[0265] Next, the following compounds H-H1, H-H2, and compound 317 (dopant) were co-deposited onto the electron blocking layer in a weight ratio of 42.5:42.5:15 to form a 400 Å thick luminescent layer.

[0266] Subsequently, compounds ET3 and ET-D1 were co-deposited on the upper part of the light-emitting layer in a 50:50 volume ratio to form a 350 Å thick electron transport layer. Compound ET-D1 was then vacuum-deposited on the upper part of the electron transport layer to form a 10 Å thick electron injection layer. Finally, Al was vacuum-deposited on the upper part of the electron injection layer to form a 1,000 Å thick cathode, thereby fabricating an organic light-emitting device.

[0267] [ka]

[0268] Examples 2-4 and Comparative Examples A-D

[0269] An organic light-emitting element was fabricated using the same method as in Example 1, except that, when forming the light-emitting layer, the compounds listed in Table 2 below were used as dopants instead of compound 317.

[0270] ≪Evaluation Example 1: Characterization of Organic Light-Emitting Devices≫

[0271] For each organic light-emitting element manufactured in Examples 1-4 and Comparative Examples A-D described above, the driving voltage, the maximum external quantum efficiency (Max EQE) (%), and the lifetime (LT) were determined. 97 The lifespan (LT) was evaluated (time: hr), and the results are shown in Table 2 below. A current / voltmeter (Keithley 2400) and a luminance meter (Minolta Cs-1000A) were used as evaluation equipment. 97 The values ​​(at 18,000 nits) represent the time (hr) required to reach 97% brightness compared to the initial brightness of 100%, and are expressed as a relative value (%).

[0272] [Table 2]

[0273] [ka]

[0274] From Table 2 above, it can be confirmed that each of the organic light-emitting devices of Examples 1 to 4 has improved external quantum efficiency and improved lifetime characteristics compared to each of the organic light-emitting devices of Comparative Examples A to D.

[0275] Although embodiments of the present invention have been described in detail above, the present invention is not limited to the embodiments described above, and can be modified and implemented in various ways without departing from the technical spirit of the present invention. [Explanation of symbols]

[0276] 10 Organic light-emitting devices 11 1st electrode 15 Organic layer 19 2nd electrode

Claims

1. An organometallic compound characterized by being represented by one of the following chemical formulas 1-1 and 1-3. 【change】 In both of the above chemical formulas 1-1 and 1-3, M is Pt. X １ and X ３ C is X ２ and X ４ is N, X ５ It is O, X ５ The combination of M and X ３ The bond between and M is a covalent bond. X ２ the bond to M and X ４ the bond to M are coordinate bonds, X １１ C(R) １１ ) or C(Z １１ ) and X １２ C(R) １２ ) and X １３ C(R) １３ ) or C(Z １３ ) and X １４ C(R) １４ ) and X ２１ C(R) ２１ ) and X ２２ C(R) ２２ ) or C(Z ２２ ) and X ２３ C(R) ２３ ) or C(Z ２３ ) and X ２９ is N-[(L ２ ) ｂ２ - (R ２ ) ｃ２ ] and X ３１ C(R) ３１ ) or C(Z ３１ ) and X ３２ C(R) ３２ ) or C(Z ３２ ) and X ３３ C(R) ３３ ) or C(Z ３３ ) and X ４１ C(R) ４１ ) and X ４２ C(R) ４２ ) and X ４３ C(R) ４３ ) or C(Z ４３ ) and X ４４ C(R) ４４ ) and Z １１ and Z １３ Z ２２ Z ２３ Z 24, Z ３１ Or Z ３３ and Z ４３ These are, independently, groups represented by the following chemical formula 51, 【Chemistry 51】 X of the above chemical formula 1-1 ２９ And in chemical formula 51, L ２ , and L ５１ Each is independently a single bond, or at least one R １０ａ A substituted or unsubstituted benzene group, X of the above chemical formula 1-1 ２９ And in chemical formula 51, b2 and b51 are independently 1 or 2, and in the aforementioned chemical formulas 1-1 and 1-3, R ２ , R １０ａ , R １１ R １４ , R ２１ R ２３ , R ３１ R ３３ and R ４１ R ４４ They are independent of each other, The group represented by the aforementioned chemical formula 51, hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups and C fluoride ３ -C １０ A C molecule that is substituted or unsubstituted with at least one cycloalkyl group. １ -C ２０ alkyl group; deuterium, -F, cyano group, C １ -C ２０ alkyl group, deuterated C １ -C ２０ alkyl group, fluorinated C １ -C ２０ alkyl group, C ３ -C １０ cycloalkyl group, deuterated C ３ -C １０ cycloalkyl group, fluorinated C ３ -C １０ cycloalkyl group, (C １ -C ２０ alkyl)C ３ -C １０ cycloalkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C １ -C ２０ alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, and (C １ -C ２０ alkyl)biphenyl group, which is unsubstituted or substituted with at least one selected from the group consisting of, C ３ -C １０ cycloalkyl group, phenyl group, biphenyl group, or naphthyl group; or -Si(Q) ３ ) (Q ４ ) (Q ５ ) or -Ge(Q ３ ) (Q ４ ) (Q ５ ); And, Of the above chemical formula 51, Q ５１ Q ５３ Two of them are independent of each other, Deuterium, -F, or cyano group; or Deuterium, -F, cyano group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups and C fluoride ３ -C １０ A C molecule that is substituted or unsubstituted with at least one cycloalkyl group. １ -C ２０ alkyl group; However, Q ５１ Q ５３ One of them is deuterium, -F, cyano group, C １ -C ２０ Alkyl alkyl groups, deuterated C １ -C ２０ Alkyl alkyl groups, C fluoride １ -C ２０ Alkyl alkyl group, C ３ -C １０ Cycloalkyl groups, deuterated C ３ -C １０ Cycloalkyl groups, C fluoride ３ -C １０ Cycloalkyl groups, (C １ -C ２０ Alkyl) C ３ -C １０ Cycloalkyl group, phenyl group, deuterated phenyl group, fluorinated phenyl group, (C １ -C ２０ Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group and (C １ -C ２０ A phenyl group, biphenyl group, naphthyl group, or pyridinyl group that is substituted or unsubstituted with at least one alkyl)biphenyl group, Q ３ Q ５ They are independent of each other, C, which is substituted or unsubstituted with at least one deuterium １ -C ６０ It is an alkyl group, X of the above chemical formula 1-1 ２９ c2 is an integer between 0 and 10. In the aforementioned chemical formula 51, c51 is either 1 or 2. The aforementioned chemical formula 1-1 is Z ２２ and Z ２３ One of them, Z ３１ Or Z ３３ One of the above, or Z ４３ Includes.

2. In the aforementioned chemical formula 51, *-C(Q ５１ ) (Q ５２ ) (Q ５３ The organometallic compound according to claim 1, characterized in that the group represented by ) is a group represented by one of the following chemical formulas 51-1 to 51-25. 【Chemistry (51-1)-(51-25)】 In the aforementioned chemical formulas 51-1 to 51-25, Q ５１ and Q ５２ The descriptions relating to each of these are the same as those described in claim 1, and Q ６１ ~Q ６６ These are, independently of each other, deuterium, -F, cyano group, and C １ -C ２０ Alkyl alkyl groups, deuterated C １ -C ２０ Alkyl alkyl groups, or C fluoride １ -C ２０ It is an alkyl group, and * is in the above chemical formula 51, L ５１ This is a linked site.

3. In the aforementioned chemical formula 51, L ５１ The organometallic compound according to claim 1, characterized in that it has a single bond.

4. The organometallic compound according to claim 1, characterized in that the group represented by the chemical formula 51 is a group represented by one of the following chemical formulas 51(1) to 51(19). 【Chemistry 51(1)-51(19)】 In the chemical formulas 51(1) to 51(19), T １１ ~T １５ Each of them is represented by the chemical formula 51 above, *-C(Q ５１ ) (Q ５２ ) (Q ５３ It is a group represented by ), T １１ ~T １５ They are either identical or different from each other, R １０ａ The explanation regarding this is the same as that described in claim 1, where * indicates a bonding site with an adjacent atom.

5. i) Represented by the chemical formula 1-1 or 1-2, wherein the chemical formula 1-1 satisfies at least one of the following conditions (1) to (3), or ii) The organometallic compound according to claim 1, represented by the chemical formulas 1-3. <Condition (1)> X ２２ is C(Z ２２ ) <Condition (2)> X ３２ is C(Z ３２ ) <Condition (3)> X ４３ is C(Z ４３ )

6. First electrode and, The second electrode and It has an organic layer disposed between the first electrode and the second electrode, which includes a light-emitting layer, The organic light-emitting element is characterized in that the organic layer contains one or more organometallic compounds as described in any one of claims 1 to 5.

7. The first electrode is an anode, The second electrode is a cathode, The organic layer further includes a hole transport region disposed between the first electrode and the light-emitting layer, and an electron transport region disposed between the light-emitting layer and the second electrode, The hole transport region includes a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof. The organic light-emitting element according to claim 6, characterized in that the electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof.

8. The organic light-emitting element according to claim 6, characterized in that the organometallic compound is included in the light-emitting layer.

9. The light-emitting layer further includes a host, The organic light-emitting element according to claim 8, characterized in that the weight of the host is greater than the weight of the organometallic compound.

10. An electronic device characterized by including an organic light-emitting element according to any one of claims 6 to 9.

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