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

Abstract

The present invention provides organometallic compounds, organic light-emitting devices containing the same, and electronic devices including organic light-emitting devices. [Solution] The organometallic compound of the present invention is represented by the following chemical formula 1. TIFF2026139761000129.tif79146

Description

[Technical Field]

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

[0002] Organic light-emitting devices are It is a self-emissive element and excels in characteristics such as viewing angle, response time, brightness, driving voltage, and response speed. It is possible to use multiple colors.

[0003] For example, an organic light-emitting element consists of an anode, a cathode, and the space between the anode and the cathode. It has an organic layer interposed between the anode and the light-emitting layer, and a hole transport region between the anode and the light-emitting layer. It is provided with an electron transport region between the light-emitting layer and the cathode. Injection from the anode The holes are transported to the light-emitting layer via the hole transport region, and the electrons injected from the cathode are charged They move to the light-emitting layer via the electron transport region. The holes and electrons recombine in the light-emitting layer region to form excitons. It generates an exciton. The exciton changes from an excited state to a ground state, producing light, for example. Visible light is then generated. [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 a novel organic Provided are a metal compound, an organic light-emitting device employing the same, and an electronic device including the organic light-emitting device .

Means for Solving the Problems

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

Chemical Formula

[0007] In other respects, the first electrode, the second electrode, and an intervening between the first electrode and the second electrode. It comprises an organic layer including a light-emitting layer, and the organic layer is an organometallic material represented by the chemical formula 1. An organic light-emitting device containing one or more compounds is provided.

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

[0009] The organometallic compound is included in the light-emitting layer in the organic layer, and the organic contained in the light-emitting layer Metal compounds act as dopants. [Effects of the Invention]

[0010] The organometallic compounds of the present invention have excellent thermal stability and electrical properties, and the organometallic compounds The electronic elements used, such as organic light-emitting devices, exhibit improved external quantum efficiency and improved lifetime characteristics. It can emit light with a relatively narrow half-width (FWHM) while possessing certain properties. [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 for iridium (Ir), platinum (Pt), osmium (Os), and titanium. Ti (Ti), Zirconium (Zr), Hafnium (Hf), Europium (Eu), Tel Bium (Tb), thulium (Tm), rhodium (Rh), palladium (Pd), or gold ( It is 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). That is the case.

[0022] In the above chemical formula 1, the bond between X5 and M is a covalent bond. The bond between X2 and M, and the bond between X3 and M One of the bonds between X4 and M is a covalent bond, and the other two are coordination bonds. It is a combination.

[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 co The bonds are identifiable, and the bonds between X2 and M, and between X4 and M, are coordinate covalent bonds.

[0025] In the above chemical formula 1, rings CY1 to CY4 are each independently C5-C 30 Carbocyclic 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) the first ring, ii) a second ring, iii) a condensed ring formed by the condensation of two or more first rings, iv) two or more second rings A fused ring formed by the condensation of rings, or v) a first ring with 1 or more rings and a second ring with 1 or more rings condensed together It is a fused ring, The first ring consists of a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, and pyrrole. Group, silole group, borol group, phosphole group, germole group, selenofen group, oxazo ethyl group, oxadiazole group, oxatriazole group, thiazole group, thiaziazole group Thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazol It is a group, or an azasilol group, The second ring consists of an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, and a cyclohexane group. Chlohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, Alternatively, it is a triazine group.

[0027] As another example, in the above chemical formula 1, rings CY1 to CY4 are each independently cyclo Pentene group, cyclohexane group, cyclohexene group, benzene group, naphthalene group, ant Helical group, phenanthrene group, triphenylene group, pyrene group, chrysene group, cyclopenta Diene group, 1,2,3,4-tetrahydronaphthalene group, thiophene group, furan group, y dole group, benzobolol group, benzophosphole group, indene group, benzosilol group, benzo Nzogermol group, benzothiophene group, benzoselenophene group, benzofuran group, Bazole group, dibenzobolol group, dibenzophosphole group, fluorene group, dibenzosilo dol group, dibenzogelmol group, dibenzothiophene group, dibenzoselenophene group, dibe Dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, di Benzothiophene 5,5-dioxide group, azaindole group, azabenzoborol group, Zabenzophosphole 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, Zadibenzoselenophen group, azadibenzofuran group, azadibenzothiophene 5-oxy do group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxy do group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrrole group Pyrazole group, imidazole group, triazole group, oxazole group, isoxazole Group, thiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzo Pyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, Nzooxadiazole group, benzothiadiazole group, 5,6,7,8-tetrahydroiso Quinoline group, 5,6,7,8-tetrahydroquinoline group, adamantane group, norbornane It is a group, or a 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 Cyclohexane group, cyclohexene group, norbornane group, or any combination thereof The following groups are condensed: benzene group, naphthalene group, fluorene group, carbazole group, dibenzo It is a thiophene group or a dibenzofuran group.

[0029] According to other examples, X2 is N, and the ring CY2 is Benzimidazole group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, tri Adin group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group; or Cyclohexane group, cyclohexene group, norbornane group, or any combination thereof The following are condensed: benzimidazole group, pyridine group, pyrimidine group, pyridazine group, Radin group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazori It is a base; it is.

[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 Cyclohexane group, cyclohexene group, norbornane group, or any combination thereof A pyridine group, pyrimidine group, pyridazine group, pyrazine group, triazine group are condensed together. , quinoline group, isoquinoline group, quinoxaline group, or quinazoline group;

[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(R 5a )(R 5b )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *- S(=O)-*', *-S(=O)2-*', *-C(R 5a )=*', *=C(R 5a )-*', *-C(R 5a )=C(R 5b )-*', *-C(=S)-*', *-C≡C -*', at least one R 10a Substitute or non-substitute C5-C 30 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(R5 a )(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, respectively. Each is independently either 0 or 1, but at least 3 of n1 to n4 are 1. That is, the organometallic compound represented by the above chemical formula 1 is a tetradentate. It has ligands. 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, and if n2 is 0, T2 If n3 is 0, then T3 is not present, and if n4 is 0, then T4 is It does not exist.

[0035] In 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. be.

[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 number of Z1 to Z4, respectively. Each is an integer between 0 and 20, independently of the others. If d1 is 2 or greater, then Z1 is 2 or greater. If they are identical or different from each other, and d2 is 2 or more, then 2 or more Z2 are identical to each other. If there is one or different, and d3 is 2 or more, then 2 or more Z3 are either identical to each other or Or they are different, and if d4 is 2 or more, then 2 or more Z4 are either the same as 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 bond , at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least Both are 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 10a A cyclopentene group, cyclohexa, substituted or unsubstituted by benzene 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, benzo Thiophene group, benzoselenophene group, benzofuran group, carbazole group, dibenzoboro Fluorine group, dibenzophosphole group, fluorene group, dibenzosilole group, dibenzogelmol L group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzoth Offen 5-oxide group, 9H-fluoren-9-one group, dibenzothiophene 5,5- Dioxide group, azaindole group, azabenzoborol group, azabenzophosphole group, Zaindene group, azabenzosilol group, azabenzogermol group, azabenzothiophene group, azabenzoselenophen group, azabenzofuran group, azacarbazole group, azadiben Zobolol group, azadibenzophosphole group, azafluorene group, azadibenzosilol group azadibenzogermol group, azadibenzothiophene group, azadibenzoselenophene group azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H-fluorine Len-9-one group, azadibenzothiophene 5,5-dioxide group, pyridine group, pyrimi Zin group, pyrazine group, pyridazine group, triazine group, quinoline group, isoquinoline group, quino Xaline group, quinazoline group, phenanthroline group, pyrrole group, pyrazole group, imidazoline thiazole group, triazole group, oxazole group, isoxazole group, thiazole group, isothazole group Azole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimi Dazole 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 be.

[0042] According to one example, in the above chemical formulas 1 and 51, L1 to L4 and L 51 These are, Independent, Single bond; or At least one R10a substituted or unsubstituted benzene groups, naphthalene groups, pyri Zin 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 of These represent the number of each element, and each is an independent integer between 1 and 10. b1 is If there are 2 or more, then the 2 or more L1s are either identical or different from each other, and b2 is 2 or more. If there are two or more L2s, they are either the same or different from each other, and if there are two or more b3s, The above L3s are either identical or different from each other, and if b4 is 2 or more, then 2 or more L4s If they are identical or different from each other, and if b51 is 2 or more, then 2 or more L 51 is mutual They are either identical or different. For example, b1 to b4 and b51 are each independently It is 1, 2, or 3.

[0044] In the above chemical formulas 1 and 51, R1 to R4, R 5a , R 5b , R', R'', and Q 51 No To Q 53 These are, independently, the group represented by the above chemical formula 51, hydrogen, deuterium, -F, and - Cl, -Br, -I, -SF5, hydroxyl group, cyano group, nitro group, amidino group, hi Drazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid C1-C groups or their salts, substituted or unsubstituted C1-C groups 60 Alkyl, substituted or unsubstituted C 2-C 60 Alkenyl group, substituted or unsubstituted C2-C 60 Alkynyl group, substitution or is unsubstituted C1-C60 alkoxy group, substituted or unsubstituted C1-C 60 Alkylthio C3-C as base, substituted, or unsubstituted 10 Cycloalkyl groups, substituted or unsubstituted C1- C 10 Heterocycloalkyl groups, substituted or unsubstituted C3-C 10 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, substitution Alternatively, non-substituted C6-C 60 Aryloxy group, substituted or unsubstituted C6-C 60 a Reelthio group, substituted or unsubstituted C1-C 60 Heteroaryl group, substitution or non-substitution C2-C replacement 60 Alkyl heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensate poly cyclic group (non-aromatic condensed polycyclic group) (up), substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group (non-aromatic) c condensed heteropolycyclic group), -N(Q 1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)(Q5), - B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q9) However, Q in the above chemical formula 51 51 ~Q 53 At least one of these is a substitution or non Substitution of C6-C 60 Aryl group, substituted or unsubstituted C1-C 60 heteroaryl group, A substituted or unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic group. It is a 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 the concrete example, R1 to R4, R', R'', and Q of the above chemical formula 1. 51 ~Q 53 teeth, It 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, R 5a , 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, hydroxy Syl group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, ka Rubonic 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 Alkyl 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, norborneyl group, cyclopentenyl group, cyclohexenyl cyclo[1.1.1]pentyl group, cycloheptenyl group, bicyclo[2.1.1]pentyl group, bicyclo[2.1.1 ]Hexyl group, bicyclo[2.2.2]octyl group, (C1-C 20 Alkyl)cyclop ethyl group, (C1-C 20 Alkyl)cyclohexyl group, (C1-C 20 Alkyl) Sic Loheptyl group, (C1-C 20 Alkyl)cyclooctyl group, (C1-C 20 Alkyl) Adamantanyl group, (C1-C 20 Alkyl) norbornanyl group ((C1-C 20 Alki (L) Bicyclo[2.2.1]heptyl group), (C1-C 20 Alkyl)norborneyl group , (C1-C 20 Alkyl)cyclopentenyl group, (C1-C 20 Alkyl)cyclohex Cenyl group, (C1-C 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bi Cyclo[1.1.1]pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1] xyl group, (C1-C 20 Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1-C 20 Alkyl)phenyl group, biphenyl group, terphenyl group, naphthyl group, pi C1-C2 substituted with a lysinyl group, a pyrimidinyl group, or any combination thereof. 0 alkyl groups, C1-C 20 Alkenyl group, C1-C 20 Alkoxy group, or C1-C2 0 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, fluorine Chemical C1-C 20 Alkyl alkyl group, C1-C 20 Alkoxy group, cyclopentyl group, cyclohex Syl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, norborneyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, Cyclo[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 Al (C1-C)cyclohexyl group, 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 20 Alkyl)cycloheptenyl group, (C1-C 20 Alkyl)bicyclo[ 1.1.1] Pentyl group, (C1-C 20 Alkyl)bicyclo[2.1.1]hexyl group , (C1-C 20Alkyl)bicyclo[2.2.2]octyl group, phenyl group, (C1- C 20 Alkyl)phenyl group, deuterated phenyl group, fluorinated 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, isothia Zolyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyrim Dinyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, plinyl quinolinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, cina Zolinyl group, synnorinyl group, carbazolyl group, phenanthrolinyl group, benzimidazol Lyl group, benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzo xazolyl group, isobenzoxazolyl group, triazolyl group, tetrazolyl group, oxadi Azolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzoca Rubazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyridinyl group, azacarbazolyl group, azadibenzofuranyl group, azadibenzothiophenyl group, or cyclopentyl groups, cyclohexyl groups, substituted or unsubstituted in any combination thereof group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group, nor Bornenyl group, cyclopentenyl group, cyclohexenyl group, cycloheptenyl group, bicyclit [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, ta - Phenyl group, naphthyl group, fluorenyl group, phenantrenyl group, anthracenyl group, Fluoranthenyl group, triphenylenyl group, pyrenyl group, chrysenyl group, pyrrolyl group, Ophenyl group, furanyl group, imidazolyl group, pyrazolyl group, thiazolyl group, isothiazo Lyl group, oxazolyl group, isoxazolyl group, pyridinyl group, pyridinyl group, pyrimidi Nyl group, pyridadinyl group, isoindolyl group, indolyl group, indazolyl group, prinyl group, quinolinyl group, isoquinolinyl group, benzoquinolinyl group, quinoxalinyl group, quinazo Linyl group, synnorinyl group, carbazolyl group, phenanthrolinyl group, benzimidazoli benzofuranyl group, benzothiophenyl group, isobenzothiazolyl group, benzooxy group Sazolyl group, isobenzooxazolyl group, triazolyl group, tetrazolyl group, oxadia Zolyl group, triazinyl group, dibenzofuranyl group, dibenzothiophenyl group, benzocal bazolyl group, dibenzocarbazolyl group, imidazopyridinyl group, imidazopyrimidinyl group , azacarbazolyl group, azadibenzofuranyl group, or azadibenzothiophenyl group; or iha -N(Q1)(Q2), -Si(Q3)(Q4)(Q5), -Ge(Q3)(Q4)( Q5), -B(Q6)(Q7), -P(=O)(Q8)(Q9), or -P(Q8)(Q 9); and Q1 through Q9 are each independent of each other. Deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -C H2CD3, -CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H , -CHDCDH2, -CHDCD3, -CD2CD3, -CD2CD2H, -CD2C DH2, -CF3, -CF2H, -CFH2, -CH2CF3, -CH2CF2H, -C H2CFH2, -CHFCH3, -CHFCF2H, -CHFCFH2, -CHFCF3 -CF2CF3, -CF2CF2H, or -CF2CFH2; or Deuterium, -F, C1-C 10 Alkyl groups, phenyl groups, or any combination thereof Substituted or unsubstituted n-propyl group, isopropyl group, n-butyl group, sec-propyl Isobutyl group, isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neopentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-iso It is a pentyl group, a phenyl group, a biphenyl group, or a naphthyl group.

[0048] Furthermore, according to other concrete examples, in the above chemical formula 1, R1 to R4, R 5a , R 5b , R', and "R" is 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 Shik Roalkyl groups, C3-C fluoride 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 Substituted with heterocycloalkyl groups or any combination thereof. Alternatively, non-substituted C1-C 20 alkyl group; Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 alkyl group Fluoride C1-C 20 Alkyl alkyl group, C1-C 20 Alkoxy group, deuterated C1-C 20 a Lucoxyl group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl groups, deuterium Chemical C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C2 0 alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, heavy Hydrogenated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl Group, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl group, phenyl group, heavy water Phenyl fluoride group, phenyl fluoride group, (C1-C 20 Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 Alkyl)biphenyl Substituted or unsubstituted by the base, or any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl groups, phenyl groups, biphenyl groups, naphthyl groups, Pyridinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, or dibenzoth Ophenyl group; 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 ~Q53 Each is independent of the others. , Hydrogen, deuterium, -F, or cyano group; Deuterium, -F, cyano group, C3-C 10 Cycloalkyl groups, deuterated C3-C 10 Shik Roalkyl groups, C3-C fluoride 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 Substituted with heterocycloalkyl groups or any combination thereof. Alternatively, non-substituted C1-C 20 alkyl group; or Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 alkyl group Fluoride C1-C 20 Alkyl alkyl group, C1-C 20 Alkoxy group, deuterated C1-C 20 a Lucoxyl group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl groups, deuterium Chemical C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C2 0 alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, heavy Hydrogenated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterocycloalkyl Group, (C1-C 20 Alkyl)C1-C 10Heterocycloalkyl group, phenyl group, heavy water Phenyl fluoride group, phenyl fluoride group, (C1-C 20 Alkyl)phenyl group, biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 Alkyl)biphenyl Substituted or unsubstituted by the base, or any combination thereof, C3-C 10 Cycloalkyl group, C1-C 10 Heterocycloalkyl groups, phenyl groups, biphenyl groups, naphthyl groups, Pyridinyl group, fluorenyl group, carbazolyl group, dibenzofuranyl group, or dibenzoth It is an offhenyl group; however, Q 51 ~Q 53 At least one of the following (for example, Q 53 ) is deuterium, -F, shear group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl, fluorinated, deuterated C 1-C 20 Alkoxy group, fluoride C1-C 20 Alkoxy group, C3-C 10 Cycloalkyl Lu group, deuterated C3-C 10 Cycloalkyl groups, fluoride C3-C 10 Cycloalkyl groups, (C1-C 20 Alkyl)C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloa Lukyl group, deuterated C1-C 10 Heterocycloalkyl groups, C1-C fluoride 10 Heterozy Chloalkyl groups, (C1-C 20 Alkyl)C1-C 10 Heterocycloalkyl groups, phe Nyl group, deuterated phenyl group, fluorinated phenyl group, (C1-C 20 Alkyl)phenyl group , biphenyl group, deuterated biphenyl group, fluorinated biphenyl group, (C1-C 20 Alkyl ) Biphenyl groups, or phenyl groups substituted or unsubstituted with any combination thereof, Biphenyl group, naphthyl group, pyridinyl group, fluorenyl group, carbazolyl group, dibenzo It is a furanyl group or a dibenzothiophenyl group.

[0050] Furthermore, according to other concrete examples, in the above chemical formula 51, i) Q 51 and Q 52 Each is independent ii) Q 51 Q is hydrogen or deuterium. 52 is water Is it not an element or deuterium, or iii) Q 51 and Q 52 Both are hydrogen and deuterium There isn't one.

[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 Each of these is independently a group represented by the above chemical formula 51. Hydrogen, deuterium, -F, -CH3, -CD3, -CD2H, -CDH2, -CF3, -C F2H, -CFH2, C2-C 10 Alkenyl group, C1-C 10 Alkoxy group, C1-C 10 Alkylthio group, a group represented by one of the following chemical formulas 9-1 to 9-39, the following chemical In formulas 9-1 to 9-39, at least one hydrogen atom is substituted with deuterium, below A group in which at least one hydrogen atom from one of the 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, the following chemical formula 9-201 ~9-227, at least one hydrogen atom is substituted with deuterium in the following chemical In formulas 9-201 to 9-227, at least one hydrogen atom is substituted with -F. , a group represented by one of the following chemical formulas 10⁻¹ to 10¹²⁹, the following chemical formula 10⁻¹ to A group in which at least one of the 10⁻¹²⁹ hydrogen atoms is substituted with deuterium, as shown in the following chemical In formulas 10-1 to 10-129, at least one hydrogen atom is substituted with -F. , a group represented by one of the following chemical formulas 10-201 to 10-350, the following chemical formula 10- A group in which at least one hydrogen atom from 201 to 10-350 is substituted with deuterium, At least one hydrogen atom in one of the following chemical formulas 10⁻²⁰¹ to 10⁻³⁵⁰ is -F Substituted group, -Si(Q3)(Q4)(Q5), or -Ge(Q3)(Q4)(Q5) (However, for explanations regarding Q3 through Q5, please refer to the respective sections in this specification.) That is the case.

[0052] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 and Q 52 Each is independent of the others. , hydrogen or deuterium, Q 53 This is one of the following chemical formulas 10⁻¹² to 10⁻¹²⁹. A group represented by the following chemical formulas 10⁻¹² to 10⁻¹²⁹, and at least one water molecule. The element is a group substituted with deuterium, one of the following chemical formulas 10⁻¹² to 10⁻¹²⁹. A group in which at least one hydrogen atom is substituted with -F, as shown in the following chemical formulas 10⁻²⁰¹ to 10⁻³⁵⁰. A group represented by one of the following chemical formulas 10⁻²⁰¹ to 10⁻³⁵ The other hydrogen is a group substituted with deuterium, or the following chemical formulas 10-201 to 10-350 One of these groups has at least one hydrogen atom substituted with -F.

[0053] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 It is hydrogen or deuterium, Q5 2 is -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH 2. A group represented by one of the following chemical formulas 9-1 to 9-39, and the following chemical formulas 9-1 to 9-3 One of the 9 groups, at least one hydrogen atom, is substituted with deuterium, or the following chemical formula 9- Q5 3 is a group represented by one of the following chemical formulas 10⁻¹² to 10⁻¹²⁹, and the following chemical formula 10 A group in which at least one hydrogen atom from -12 to 10-129 is substituted with deuterium, At least one hydrogen atom in one of the following chemical formulas 10⁻¹² to 10⁻¹²⁹ is placed at -F The replaced group is a group represented by one of the following chemical formulas 10-201 to 10-350, as follows At least one hydrogen atom in one of the formulas 10⁻²⁰¹ to 10⁻³⁵⁰ is replaced by deuterium. The group that is formed, or at least one of the following chemical formulas 10-201 to 10-350 It is a group in which hydrogen is substituted with -F.

[0054] Furthermore, according to other concrete examples, in the above chemical formula 51, Q 51 and Q 52 Each is independent of the others. , -CH3, -CD3, -CD2H, -CDH2, -CF3, -CF2H, -CFH2, A group represented by one of the following chemical formulas 9-1 to 9-39, or the group represented by one of the following chemical formulas 9-1 to 9-39 One of the hydrogen atoms in the group is substituted with deuterium, or the group shown in chemical formula 9-1~ One of the groups 9-39 has at least one hydrogen atom that is substituted with -F, and Q 53teeth , a group represented by one of the following chemical formulas 10-12 to 10-129, the following chemical formula 10-1 A group in which at least one hydrogen atom from 2 to 10⁻¹²⁹ is substituted with deuterium, as follows: At least one hydrogen atom in one of the 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, the following chemical formula At least one hydrogen atom in one of the 10⁻²⁰ to 10⁻³⁵ atoms is replaced by deuterium. A group, or at least one hydrogen atom from one of the following chemical formulas 10-201 to 10-350. However, it is a group substituted with -F.

[0055] Furthermore, according to other concrete examples, Q of the above chemical formula 51 51 ~Q 53 at least one of (For example, Q 51 ~Q 53 One of them is the one with the following chemical formulas 10⁻¹² to 10⁻¹²⁹ One of the groups represented by these, at least one of the following chemical formulas 10⁻¹² to 10⁻¹²⁹ Another hydrogen atom is substituted with deuterium in the group, of the following chemical formulas 10-12 to 10-129. A group in which at least one hydrogen atom is substituted with -F, as shown in the chemical formula 10-201~10- A group represented by one of 350, one of the following chemical formulas 10⁻²⁰¹ to 10⁻³⁵. At least one hydrogen atom is substituted with deuterium in the group, or the following chemical formulas 10-201~10 One of the -350 groups is a group in which at least one hydrogen atom is substituted with -F.

[0056] [ka]

[0057] [ka]

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

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

[0060] The above chemical formulas 9-1 to 9-39, 9-201 to 9-227, and 10- In the chemical formulas 1 to 10⁻¹²⁹ and 10⁻²⁰¹ to 10⁻³⁵⁰ above, * indicates the relationship with neighboring atoms. The binding site is where Ph is a phenyl group and TMS is a trimethylsilyl group. TMG stands for trimethylgermyl group.

[0061] The above "At least one hydrogen atom among chemical formulas 9-1 to 9-39 is substituted with deuterium" The group, and at least one hydrogen atom from chemical formulas 9-201 to 9-227, is deuterium. The "substituted group" is, for example, chemical formulas 9-501 to 9-514 and chemical formula 9-6 below. This is a group represented by 01-9-636.

[0062] [ka]

[0063] [ka]

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

[0065] [ka]

[0066] The above statement "At least one hydrogen atom among chemical formulas 10⁻¹ to 10⁻¹²⁹ is substituted with deuterium" "a group that has been modified", and "at least one hydrogen from chemical formulas 10⁻²⁰¹ to 10⁻³⁵ The group substituted with deuterium is, for example, represented by the following chemical formulas 10-501 to 10-553. It is the basis.

[0067] [ka] [ka]

[0068] The above "at least one hydrogen atom among chemical formulas 10-1 to 10-129 is substituted with -F" "a group formed by" and "at least one hydrogen atom from chemical formulas 10-201 to 10-350, A group substituted with -F is, for example, a group represented by the following chemical formulas 10-601 to 10-617. That is the case.

[0069] [ka]

[0070] c1 to c4 and a1 to a4 in the above chemical formula 1 are R1 to R4, *-[(L1) b 1-(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) This indicates the number of each element represented by [c4], and each is independent of 0 to 20. It is an integer. If c1 is 2 or greater, then R1 values ​​of 2 or greater are either identical or different. If c2 is 2 or more, then the 2 or more R2s are either identical or different from each other, and c3 is If there are 2 or more, then the 2 or more R3s are either identical or different from each other, and c4 is 2 or more. If so, then two or more R4s are either the same or different from each other, and if a1 is two or more, The above *-[(L1) b1 -(R1) c1 The bases represented by ] are either identical or different from each other. If a2 is 2 or greater, then *-[(L2) b2 -(R2) c2 Represented by ] The bases are either identical or different to each other, and if a3 is 2 or more, then 2 or more *-[(L 3) b3 -(R3) c3 The bases represented by ] are either identical or different from each other, and a4 is 2 or less If the above is true, then 2 or more *-[(L4) b4 -(R4) c4 The bases represented by ] are the same as each other. They are either one or different. For example, c1 to c4 and a1 to a4 of the above chemical formula 1 are Each is independently 0, 1, 2, or 3.

[0071] In the above chemical formula 51, c51 is *-C(Q 51 )(Q 52 )(Q 53 The individual bases represented by ) This represents a number, an integer between 1 and 20. If c51 is 2 or greater, then * is 2 or greater. -C(Q 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 is one of the following <Condition 1> and <Condition 2>. It satisfies at least one of the following conditions.

[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. That is, the organometallic compound represented by the above chemical formula 1 is at least one of the above chemical formula 51 Includes the represented group.

[0074] According to one example, the organometallic compound represented by the above chemical formula 1 is subject to the following conditions <Condition 1A> and At least one of the following conditions <Condition 2A> must be satisfied.

[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) Are d2 and d3 each 1, and d1 and d4 each 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 The above Is it a base represented by 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 them is a group represented by the above chemical formula 51. be.

[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 Another 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) Multiple R3 groups Two or more of these are selectively coupled to each other, and at least one R 10a Replace or omit with Replacement 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 multiple R4 groups are selectively bonded to each other. In total, at least one R 10a Substitute or non-substitute C5-C 30 Carbon ring group, or a small Even without one R 10a Substitute or non-substitute C1-C 30 Forms a heterocyclic group, iv ) Two or more of R1 to R4, one of R1 to R4, and R 5a , R1 to R4 one of the following, and R 5b , or R 5a and R 5b Each of them selectively binds to the others. And at least one R 10a Substitute or non-substitute C5-C 30 Carbon ring group, or a small number Even if it's just 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 to be added is one represented by one of the following chemical formulas 51-1 to 51-25.

[0080] [ka]

[0081] In the above chemical formulas 51-1 to 51-25, Q 51 and Q 52 The explanations for each of them are as follows: Refer to the sections described in this specification, Q 61 ~Q 66 The explanations for each of them are In each of these specifications, R 10a Refer to the explanation regarding Q 61 ~Q6 Each of the 5 is not hydrogen, and * is in the above chemical formula 51, L 51 It 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 Each of them independently uses heavy water Element, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl, fluorine Chemical C1-C 20 Alkyl 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 Each of them operates independently. Deuterium, -F, cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 alkyl group, Fluoride C1-C 20 Alkyl groups, phenyl groups, deuterated phenyl groups, fluorinated phenyl groups, 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 and -F cyano group, C1-C 20 Alkyl groups, deuterated C1-C 20 Alkyl alkyl groups, C1- fluoride C 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 becomes a single bond, as described above. It is a group represented by one of the chemical formulas 51-1 to 51-20.

[0085] Furthermore, according to other concrete examples, the group represented by the above chemical formula 51 is represented by the following chemical formulas 51(1) to 5 It is a base represented by one of 1(19).

[0086] [ka]

[0087] In the above chemical formulas 51(1) to 51(19), T 11 ~T 15 Each of the above chemical formulas 51, *-C(Q51 )(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 as follows in this specification, R1 Refer to the explanation regarding this, 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). be.

[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 19 a )(R 19b ) and R 19a and R 19b The explanations for each of these are as follows in this specification: Refer to the explanation, * 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 groups represented by the following chemical formulas are CY1-1 to CY1-18, and ZCY1-1 to CY1-18. It is a group represented by one of the ZCY1-32 groups.

[0092] [ka]

[0093] [ka]

[0094] The above chemical formulas CY1-1 to CY1-18, and the above chemical formulas ZCY1-1 to ZCY1-32 in, For a description of X1, please refer to the relevant section in this specification. R 11 ~R 14 For explanations regarding each of these, see the explanation regarding R1 in this specification. The reference, R 11 ~R 14 Each of them is not hydrogen, Z 11 ~Z 14 For explanations of each of these, see the explanation of Z1 in this specification. Refer to, * 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 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 21 Y 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). be.

[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 29 a )(R 29b ), or Si(R 29a )(R 29b ) and For explanations regarding L2, b2, R2, and c2, please refer to the relevant sections in this specification. Refer to, Z 24 For further explanation, please refer to the explanation for Z2 in this specification. R 29a and R 29b The explanations for each of these are as follows in this specification: Refer to the explanation, *' 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 groups represented by the following chemical formulas are CY2-1 to CY2-16, and ZCY2-1 to CY2-16. It is a group represented by one of the ZCY2-19 groups.

[0102] [ka]

[0103] [ka]

[0104] The above chemical formulas CY2-1 to CY2-16, and the above chemical formulas ZCY2-1 to ZCY2-19 in, 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 )(R29b ) and For explanations regarding L2, b2, R2, and c2, please refer to the relevant sections in this specification. Refer to, Z 21 ~Z 24 For explanations of each of these, see the explanation for Z2 in this specification. Refer to, R 21 ~R23, R 29a and R 29b For further explanations regarding each of these, see the following in this specification. Although we refer to the explanation regarding R2, 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). be.

[0106] [ka]

[0107] The above chemical formulas CY3(1) to CY3(15) For a description of X3, please refer to the relevant sections in this specification. X 39 O, S, N(Z 39a ), C(R 39a )(R 39b ), or Si(R 39 a )(R 39b ) and R 39a and R 39b The explanations for each of these are as follows in this specification: Refer to the explanation, * 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 groups represented by the following chemical formulas are CY3-1 to CY3-13, and ZCY3-1 to CY3-13. It is a group represented by one of the ZCY3-12 groups.

[0109] [ka]

[0110] [ka]

[0111] The above chemical formulas CY3-1 to CY3-13, and the above chemical formulas ZCY3-1 to ZCY3-12 in, For a description of X3, please refer to the relevant sections in 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 regarding L3, b3, R3, and c3, please refer to the relevant sections in this specification. Refer to, R 31 ~R 33 , R39a and R 39b For further explanations regarding each of these, see the following in this specification. However, although we refer to the explanation regarding R3, 31 ~R 33 Each of them is not hydrogen , Z 31 ~Z 33 For explanations of each of these, see the explanation for Z3 in this specification. Refer to, * 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). be.

[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 49 a )(R 49b ) and R 49a and R 49b The explanations for each of these are as follows in this specification: Refer to the explanation, *' 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 groups represented by the following chemical formulas are CY4-1 to CY4-16, and ZCY4-1 to CY4-16. It is a group represented by one of the ZCY4-32 groups.

[0116] [ka]

[0117] [ka]

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

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

[0120] [ka]

[0121] In the above chemical formulas 1-1 to 1-4, The descriptions of M, X1 to X5, T2 and T3 are as described in the section specified herein. Refer to the source, 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 14 For explanations regarding each of these, see the explanation regarding R1 in this specification. Refer to, Z 11 ~Z 14 For explanations of each of these, see the explanation of Z1 in this specification. Refer to, R 11 ~R 14 Two or more of them are optionally bound to each other. , at least one R 10a Substitute or non-substitute C5-C 30 A carbon ring group, or at least Both are 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 regarding L2, b2, R2, and c2, please refer to the relevant sections in this specification. Refer to, R 21 ~R 23 , R 29a , and R 29b For explanations regarding each of these, see this specification. See the explanation regarding R2. Z 21 ~Z 24 For explanations of each of these, see the explanation for Z2 in this specification. Refer to, R 21 ~R 23 Two or more of these are selectively coupled to each other, and at least one R 10 a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Replace with Alternatively, non-substituted 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 33For explanations regarding each of these, see the explanation regarding R3 in this specification. Refer to, Z 31 ~Z 33 For explanations of each of these, see the explanation for Z3 in this specification. Refer to, R 31 ~R 33 Two or more of these are selectively coupled to each other, and at least one R 10 a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Replace with Alternatively, non-substituted 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, see the explanation regarding R4 in this specification. Refer to, Z 41 ~Z 44 For explanations of each of these, see the explanation of Z4 in this specification. Refer to, R 41 ~R 44 Two or more of these are selectively coupled to each other, and at least one R 10 a Substitute or non-substitute C5-C 30 A carbon ring group, or at least one R 10a Replace with Alternatively, non-substituted 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 No To Z 24 One of them, Z 31 ~Z 33 One of them, Z 41 ~Z 44 one of , 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 are, At least one of the following conditions (1) to (3) must be satisfied, ii) Represented by the above chemical formulas 1-3 or 1-4, or iii) The substance represented by the above chemical formula 1-3 or 1-4, but the above chemical formulas 1-3 and 1-4 It satisfies 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 Z2 1 to Z 24 , Z 31 ~Z 33 , and Z 41 ~Z 44 Each of these is independent of the above. It is a base represented by one of the formulas 51-1 to 51-25.

[0125] Furthermore, according to other examples, in this specification, Z1 to Z4, Z 11 ~Z 14 Z2 1 to Z 24 , Z 31 ~Z 33 , and Z 41 ~Z 44 Each of these is independent of the above. It is a base represented by one of the formulas 51(1) to 51(19).

[0126] Furthermore, according to other concrete examples, the organometallic compound represented by the above chemical formula 1 is subject to the following <Condition A> ~At least one of the conditions E is satisfied.

[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 above. be <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 above. be <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. be <Condition D> In the above chemical formula 1, n3 is 1 and n4 is 0. [ka] The group represented is one of the chemical formulas ZCY4-1 to ZCY4-32 above. be <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, according to other concrete examples, the organometallic compound represented by the above chemical formula 1 emits green light. ru.

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

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

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

change

[0131] The organometallic compound represented by the above chemical formula 1 is subject to the conditions described herein, such as <Condition 1> and It satisfies at least one of the following conditions: that is, the organic gold represented by the above chemical formula 1. The compound in this group contains at least one group represented by the above chemical formula 51 as a substituent. Therefore, the organometallic compound represented by the above chemical formula 1 has improved planarity and orientation characteristics. Electronic devices employing the organometallic compound represented by the above chemical formula 1, such as organic light-emitting devices. Light efficiency and / or lifespan are improved.

[0132] In organometallic compounds represented by the above chemical formula 1, the HOMO(high est occupied molecular orbital) energy level, LUMO(lowest unoccupied molecular orbital ) Energy levels and T1 energy levels are determined by density functional theory based on B3LYP Molecular structure optimization using (DFT: density functional theory) The results of the evaluation using the Gaussian09 program with modifications are shown in Table 1 below. It is.

[0133] [Table 1]

[0134] From Table 1 above, organometallic compounds represented by chemical formula 1 are used in electronic devices, such as organic light-emitting devices. To confirm that it has electrical characteristics suitable for use as a dopant in a device. It is possible.

[0135] The method for synthesizing the organometallic compound represented by the above chemical formula 1 is described in the synthesis examples below. It will be possible for them to recognize it.

[0136] Therefore, the organometallic compound represented by the above chemical formula 1 is used in the organic layer of an organic light-emitting device, for example, In the device layer, it is suitable for use as a dopant in the light-emitting layer, and according to other aspects, the first electric It comprises a electrode, a second electrode, and an organic layer containing a light-emitting layer, which is disposed between the first electrode and the second electrode. The organic layer contains at least one organometallic compound represented by the above chemical formula 1, and is an organic light-emitting compound. The element is provided.

[0137] The organic light-emitting device comprises an organic layer containing an organometallic compound represented by the chemical formula 1 as described above. This allows for high external quantum efficiency and long lifetime characteristics.

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

[0139] In this specification, "(the organic layer) contains one or more organometallic compounds" means "(the organic layer (i) an organometallic compound belonging to the category of chemical formula 1 above, or belonging to the category of chemical formula 1 above This is interpreted as "containing two or more organometallic compounds that are different from each other."

[0140] For example, the organic layer contains only compound 1 as an organometallic compound. Compound 1 is present in the light-emitting layer of the organic light-emitting device. Alternatively, the organic layer may be composed of organometallic compounds. , comprising compound 1 and compound 2 above. Here, compound 1 and compound 2 are present in the same layer. They are present (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. Either the first electrode is a cathode which is an electron injection electrode, and the second electrode is a hole injection electrode. This is the anode, which is an electrode.

[0142] For example, in an organic light-emitting element, the first electrode is the anode and the second electrode is the cathode. The organic layer is a hole transport region located between the first electrode and the light-emitting layer. (port region), and electron transport region (el) located between the light-emitting layer and the second electrode. The ectron transport region further includes the hole transport region. It includes an injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or any combination thereof. The electron transport region consists of a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. Includes.

[0143] In this specification, "organic layer" refers to the layer between the first electrode and the second electrode in an organic light-emitting device. This term refers to one and / or more layers arranged in a structure. The "organic layer" is composed solely of organic compounds. It does not contain metals, but also includes 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 following describes the structure and manufacturing method of an organic light-emitting element according to one embodiment of the present invention, with reference to Figure 1. The explanation is as follows: The organic light-emitting element 10 consists of a first electrode 11, an organic layer 15, The structure has the first electrode and the second electrode 19 stacked in that order.

[0145] A substrate is additionally placed below the first electrode 11 or above the second electrode 19. Therefore, while substrates commonly used in organic light-emitting devices can be used, mechanical strength, A glass substrate or transparent glass substrate that is excellent in thermal stability, transparency, surface smoothness, ease of handling, and water resistance. A bright plastic substrate will be used.

[0146] The first electrode 11 is formed, for example, by depositing the material for the first electrode onto the upper part of the substrate using a vapor deposition method or a sputtering method. It is formed by providing the following. The first electrode 11 is the anode. The electrode material includes a material with a high work function to facilitate hole injection. Electrode 11 is a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. As the material for the first electrode These are indium tin oxide (ITO), indium zinc oxide (IZO), and tin oxide (SnO 2) Zinc oxide (ZnO), etc. can be used. Alternatively, magnesium (Mg) Aluminum (Al), aluminum-lithium (Al-Li), calcium (Ca) Metals such as magnesium-indium (Mgn) and magnesium-silver (Mg-Ag). You can use it.

[0147] The first electrode 11 has a single-layer structure or a multilayer structure including two or more layers. Pole 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 is a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof. Includes combinations of meanings.

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

[0153] If the hole transport region includes a hole injection layer, the hole injection layer is located above the first electrode 11, under vacuum vapor Coating method, spin coating method, casting method, LB (Langmuir-Blodgett) It is formed using a variety of methods, such as the ) method.

[0154] When forming a hole injection layer by vacuum deposition, the deposition conditions are as follows: It varies depending on the compound used, the structure of the hole injection layer, the thermal properties, etc. , deposition temperature approximately 100 to approximately 500℃, vacuum degree approximately 10 -8 ~about 10 -3 Torr, deposition rate approximately The selection is made from a range of 0.01 to approximately 100 Å / sec.

[0155] When forming a hole injection layer by spin coating, the coating conditions are: Depending on the compound used as the injection layer material, the structure of the target hole injection layer, and its thermal properties Unlike other methods, the coating process is carried out at a coating speed of approximately 2,000 rpm to approximately 5,000 rpm. The heat treatment temperature for solvent removal after filling is selected from a temperature range of approximately 80°C to 200°C. It will be selected.

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

[0157] Hole transport regions include, for example, m-MTDATA, TDATA, 2-TNATA, NPB, β-NPB, TPD, spiro-TPD, spiro-NPB, methylated -NPB, TAPC, HMTPD, 4,4',4"-Tris(N-carbazolyl) Trif Phenylamine (TCTA), Polyaniline / Dodecylbenzenesulfonic acid (Pani / DBSA), poly(3,4-ethylenedioxythiophene) / poly(4-styrene sulfur (PEDOT / PSS), polyaniline / camphor sulfonic acid (Pani / CSA), polyaniline / poly(4-styrene sulfonate) (PANI / PSS), below Compounds represented by the chemical formula 201, compounds represented by the chemical formula 202 below, or any of the same Includes combinations of meanings.

[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 salt thereof, sulfonic acid group or salt thereof, phosphorus Acid group or its salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 a Lukinyl group, C1-C 60 Alkoxy group, C3-C 10 Cycloalkyl groups, C3-C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkyl groups, C1-C 10 Heterocyclo Alkenyl group, C6-C 60 Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic Phenyle heterocondensed polycyclic groups, or any combination thereof, substituted or unsubstituted. n group, pentarenylene group, indenylene group, naphthylene group, azurenylene group, heptarenium Len group, acenaphthylene group, fluorenylene group, phenalenylene group, phenantrenylene group, anthracenylene group, fluoranenylene group, triphenyleneylene group, pyrenylene group , chrysenylene group, naphthasenylene group, picenylene group, perylene group, or penta It is a senylene group.

[0161] In the above chemical formula 201, xa and xb are independent integers from 0 to 5, or 0, 1, Alternatively, it could be 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, sulfo 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 a Lucoxy groups (e.g., methoxy group, ethoxy group, propoxy group, butoxy group, pentoxy group) (e.g., base) Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino Groups, amidino groups, hydrazine groups, hydrazone groups, carboxylic acid groups or their salts, sulfonic acid groups Substituted or unsubstituted with its salt, a phosphate group or its salt, or any combination thereof. C1-C 10 Alkyl alkyl group, or C1-C 10 Alkoxy group; or Deuterium, -F, -Cl, -Br, -I, hydroxyl group, cyano group, nitro group, amino Groups, amidino groups, hydrazine groups, hydrazone groups, carboxylic acid groups or their salts, sulfonic acid groups or its salt, phosphate group or its salt, C1-C 10 Alkyl alkyl group, C1-C 10 Alkoxy group , or any combination thereof, substituted or unsubstituted phenyl group, naphthyl group, a It is an interthracenyl group, a fluorenyl group, or a pyrenyl group.

[0163] In the above chemical formula 201, R 109 These are deuterium, -F, -Cl, -Br, -I, and hydroxyl chloro group, cyano group, nitro group, amino group, amidino group, hydrazine group, hydrazone group, carboxyl group phosphate group or its salt, sulfonic acid group or its salt, phosphate group or its salt, C1-C 20 Al Kill group, C1-C 20 Alkoxy group, phenyl group, naphthyl group, anthracenyl group, pyri Phenyl groups, naphthium groups, and naphthium groups, substituted or unsubstituted with a dinyl group or any combination thereof. It is a yl group, anthracenyl group, or pyridinyl group.

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

[0165] [ka]

[0166] In the above chemical formula 201A, R 101 , R111 , R 112 , and R 109 Detailed information For details, please refer to the section mentioned above.

[0167] For example, the hole transport region is one of the following compounds HT1 to HT20, or any of them. Includes combinations of meanings.

[0168] [ka] [ka]

[0169] The thickness of the hole transport region is approximately 100 Å to approximately 10,000 Å, for example, approximately 100 Å to approximately 1,0 It is 00Å. The hole transport region is a hole injection layer, a hole transport layer, an electron blocking layer, or a combination of these. If the combination includes the intended elements, the thickness of the hole injection layer is approximately 100 Å to approximately 10,000 Å. The thickness is 0 Å, for example, approximately 100 Å to approximately 1,000 Å, and the thickness of the hole transport layer is approximately 50 Å to approximately 2 ,000 Å, for example, about 100 Å to about 1,500 Å. Hole transport region, hole injection layer, and If the thickness of the hole transport layer satisfies the above-mentioned range, then without a substantial increase in the driving voltage. This allows us to obtain satisfactory hole transport characteristics.

[0170] In addition to the materials mentioned above, the hole transport region can also be further enhanced by charge-generating materials to improve conductivity. Includes. The charge-generating material is 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, These are metal oxides, cyano group-containing compounds, or any combination thereof. For example, p-type The dopant is tetracyanoquinone dimethane (TCNQ), 2,3,5,6-tetraflu Oro-tetracyano-1,4-benzoquinone dimethane (F4-TCNQ), F6-TCN Quinone derivatives such as NQ; metal oxides such as tungsten oxide and molybdenum oxide. Substance; cyano group-containing compounds such as the following compound HT-D1; or any combination thereof That is so.

[0172] [ka]

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

[0174] The buffer layer compensates for the optical resonance distance due to the wavelength of light emitted from the light-emitting layer, thereby improving efficiency. It plays a role in increasing [something].

[0175] On the other hand, if the hole transport region includes an electron blocking layer, the electron blocking layer material will have the same hole transport region as described above. This includes a substance used in the transmission area, a host substance described later, or any combination thereof. For example, if the hole transport region includes an electron blocking layer, the electron blocking layer material can be the mCP described later. Use compound H-H1, or any combination thereof.

[0176] Above the hole transport region, methods such as vacuum deposition, spin coating, casting, and LB are used. The light-emitting layer is formed using the following methods: vacuum deposition and spin coating. When forming a light-emitting layer, the deposition conditions and coating conditions depend on the compound used. Unlike other methods, the conditions are generally selected from a range of conditions that are nearly identical to those for hole injection layer formation.

[0177] The light-emitting layer comprises a host and a dopant, the dopant being as described herein It contains organometallic compounds represented by formula 1.

[0178] The hosts are TPBi, TBADN, ADN ("DNA"), CBP, and CDB. P, TCP, mCP, compound H50, compound H51, compound H52, compound H-H1, compound Includes compound H-H2, or any combination thereof.

[0179] [ka]

[0180] If the organic light-emitting element is a full-color organic light-emitting element, the light-emitting layer consists of a red light-emitting layer and a green light-emitting layer. Patterned by a layer and / or a blue light-emitting layer. Alternatively, the light-emitting layer is a red light-emitting layer. By having a structure in which a green light-emitting layer and / or a blue light-emitting layer are laminated, it emits white light. Various modifications are possible, such as "extracting."

[0181] When the luminescent layer contains both a host and a dopant, the dopant content is generally about 1% of the host content. Based on 00 parts by weight, the amount is selected from a range of approximately 0.01 to approximately 20 parts by weight.

[0182] The thickness of the luminescent 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-mentioned range, excellent performance can be achieved without a substantial increase in the driving voltage. It can exhibit excellent luminescence characteristics.

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

[0184] The electron transport region consists of a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. Includes se.

[0185] For example, the electron transport region could be a hole blocking layer / electron transport layer / electron injection layer, or an electron transport layer / electron It has a electron injection layer structure. The electron transport layer has a single layer structure or contains two or more different materials. It has a multi-layered structure.

[0186] The formation conditions for the hole blocking layer, electron transport layer, and electron injection layer in the electron transport region are as follows: Refer to the formation conditions.

[0187] If the electron transport region includes a hole blocking layer, the hole blocking layer may be, for example, BCP, Bphen as described below. This includes 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. If the hole blocking layer thickness satisfies the above-mentioned range, there is no substantial increase in the drive voltage. This allows for the acquisition of excellent hole blocking characteristics.

[0190] The electron transport layer consists of the above BCP, Bphen, TPBi, and the following Alq3, BAlq, T Includes AZ, NTAZ, or any combination thereof.

[0191] [ka]

[0192] Alternatively, the electron transport layer may be one of the following compounds ET1 to ET25, or any of them. This includes combinations.

[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. Yes. If the thickness of the electron transport layer satisfies the above-mentioned range, the effective increase in drive voltage is... Therefore, satisfactory electron transport characteristics can be obtained.

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

[0196] Metal-containing substances include Li complexes. Li complexes include, for example, the following compound ET-D1 or compound Includes object 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 consists of LiF, NaCl, CsF, Li2O, BaO, and the above compound ET-D1. , comprising the above 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. If the layer thickness satisfies the range described above, the satisfaction can be achieved without any substantial increase in the driving voltage. Electron injection characteristics can be obtained.

[0201] A second electrode 19 is placed on top of the organic layer 15. The second electrode 19 is the cathode. The material for the second electrode 19 is a metal, alloy, or electrically conductive material with a relatively low work function. Compounds, or any combination thereof, can be used. Specific examples include: Thium (Li), magnesium (Mg), aluminum (Al), aluminum-lithium Al-Li, Calcium (Ca), Magnesium-Indium (Mg-In), Ma Magnesium-silver (Mg-Ag), etc., is used as the material for forming the second electrode 19. To obtain a front-facing light-emitting element, a transmissive second electrode 19 is formed using ITO and IZO. As such, a variety of transformations are possible.

[0202] The above explanation of organic light-emitting devices was given with reference to Figure 1, but the types of light-emitting devices are not limited to those described above. There isn't one.

[0203] Furthermore, from another perspective, organic light-emitting elements are included in electronic devices. Therefore, organic light-emitting elements Electronic devices are provided, including, for example, displays, lighting, sensors, etc. nothing.

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

[0205] Can the organometallic compound represented by the above chemical formula 1 provide high luminescence efficiency? Furthermore, diagnostic compositions containing organometallic compounds can have high diagnostic efficiency.

[0206] Diagnostic compositions are used in various diagnostic kits, diagnostic reagents, biosensors, biomarkers, etc. It has a wide range of applications.

[0207] In this specification, C1-C 60 Alkyl alkyl groups are linear or branched saturates with 1 to 60 carbon atoms. This refers to a monovalent group of aliphatic hydrocarbons, C1-C 60 The alkylene group is C1-C 60 Alkyl This refers to a divalent group that has the same structure as the base.

[0208] In this specification, C1-C 60 Alkyl alkyl group, C1-C 20 Alkyl alkyl groups, and / or C 1-C 10 Examples of alkyl groups include methyl group, ethyl group, n-propyl group, and 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 xyl group, tert-hexyl group, n-heptyl group, isoheptyl group, sec-heptyl group, tert-heptyl group, n-octyl group, isooctyl group, sec-octyl group, t ert-octyl group, n-nonyl group, isononyl group, sec-nonyl group, tert-nonyl n-decyl group, n-decyl group, isodecyl group, sec-decyl group, tert-decyl group, or the A methyl group, an ethyl group, an n-propyl group, substituted or unsubstituted in any combination thereof. 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, s ec-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, or tert- It includes decyl groups, etc. For example, the above chemical formula 9-33 is a branched C6 alkyl group. It can be seen as a tert-butyl group substituted with two methyl groups.

[0209] In this specification, C1-C 60 The alkoxy group is -OA 101 (Here, A 101 teeth , C1-C 60 It refers to a monovalent group having the chemical formula (which is an alkyl group), and a specific example is This includes methoxy groups, ethoxy groups, propoxy groups, butoxy groups, or pentoxy groups. It can be done.

[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 intermediate or It has a structure containing one or more carbon-carbon double bonds at its terminal, and a specific example of this is ethenyl. This includes groups such as propenyl groups and butenyl groups. In this specification, C2-C 60 Alke The nilen 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 intermediate or It has a structure containing one or more carbon-carbon triple bonds at its terminal, and a specific example of this is ethynyl This includes groups such as propynyl groups. 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 Monohydrated hydrocarbons It means a cyclic group, C3-C 10 The cycloalkylene group is C3-C 10 Cycloalkyl groups and This refers to divalent groups having the same structure.

[0214] In this specification, C3-C 10 Examples of cycloalkyl groups include cyclopropyl group, cyclo Robyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, adamantanyl group, norbornanyl group (or bicyclo[2.2.1]heptylgy) , bicyclo[1.1.1]pentyl group, bicyclo[2.1.1]hexyl group, bicyclo[ 2.2.2] Contains octyl groups, etc.

[0215] In this specification, C1-C 10 Heterocycloalkyl groups are N, O, P, Si, S, At least one heteroatom selected from Se, Ge, and B is used as a ring-forming atom. and include C1-C 10 This refers to a monovalent monocyclic group, C1-C 10 The heterocycloalkylene group is C 1-C 10 This refers to a divalent group having the same structure as a heterocycloalkyl group.

[0216] In this specification, C1-C 10Examples of heterocycloalkyl groups include siloranil group, siloranil group, siloranil group Linanyl group, tetrahydrofuranyl group, tetrahydro-2H-pyranyl group, tetrahydro It contains thiophenyl groups, etc.

[0217] In this specification, C3-C 10 The cycloalkenyl group is C3-C 10 monovalent cyclic group Furthermore, it has at least one carbon-carbon double bond within the ring, but is aromatic (aromat This refers to a group that does not have icity, and specific examples include the cyclopentenyl group and the cyclohexyl group. Includes a nyl group, a cycloheptenyl group, etc. In this specification, C3-C 10 Cycloalke The nilen 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 Heterocycloalkenyl groups are N, O, P, Si, S At least one heteroatom selected from Se, Ge, and B is used as a ring-forming atom. and include C1-C 10 It 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, 2, Contains a 3-dihydrothiophenyl group, etc. In this specification, C1-C 10 Heterocyclo The alkenylene group is C1-C 10 A divalent group having the same structure as a heterocycloalkenyl group It means.

[0219] In this specification, C6-C 60 The aryl group is C6-C 60 Having a carbon-ring aromatic system It means a monovalent group, C6-C 60The arylene group is C6-C 60 Two carbon-ring aromatic systems This refers to the valence group. C6-C 60 Specific examples of aryl groups include the phenyl group, naphthyl group, and ant group. Includes racenyl group, phenantrenyl group, pyrenyl group, chrysenyl group, etc. C6-C 60 Aryl group and C6-C 60 If the arylene group contains two or more rings, the two or more rings are relative to each other. It will be fused with.

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

[0221] In this specification, C1-C 60 Heteroaryl groups include N, O, P, Si, S, Se, It contains at least one heteroatom selected from Ge and B as a ring-forming atom. , C1-C 60 This refers to a monovalent group having a cyclic aromatic system, C1-C 60 heteroarylene group This is at least one selected from N, O, P, Si, S, Se, Ge, and B. It contains heteroatoms as ring-forming atoms, C1-C 60 This refers to a divalent group having a cyclic aromatic system. C1-C 60 Specific examples of heteroaryl groups include pyridinyl group, pyrimidinyl group, and pyrazi Includes yl groups, pyridadinyl groups, triazinyl groups, quinolinyl groups, isoquinolinyl groups, etc. C1-C 60 Heteroaryl group and C1-C 60 The heteroarylene group contains two or more rings In this case, two or more rings fuse together.

[0222] In this specification, C2-C 60 The alkyl heteroaryl 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 10 2 is 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 a The lukirthio group is -SA 104 (Here, A 104 C1-C 60 (It is an alkyl group.) This indicates.

[0224] In this specification, a monovalent non-aromatic condensed polycyclic group is defined as a ring-shaped group formed by the condensation of two or more rings with respect to each other. It contains only carbon as a constituent atom, and the entire molecule is non-aromatic. This refers to a monovalent group (for example, having 8 to 60 carbon atoms) that has ). Monovalent non-aromatic condensation Specific examples of polycyclic groups include fluorenyl groups. In this specification, divalent non-aromatic condensed polycyclic groups are used. A ring group refers to a divalent group that has the same structure as a monovalent non-aromatic condensed polycyclic group.

[0225] In this specification, a monovalent non-aromatic heterocondensed polycyclic group is defined as a group in which two or more rings are condensed together. In addition to carbon, the ring-forming atoms are selected from N, O, P, Si, S, Se, Ge, and B. A monovalent group containing at least one selected heteroatom, the entire molecule having non-aromatic properties. For example, it means having 1 to 60 carbon atoms. Monovalent non-aromatic heterocondensed polycyclic groups are Includes a rubazolyl group, etc. In this specification, a divalent non-aromatic heterocondensed polycyclic group is a monovalent non This refers to a divalent group that has the same structure as an aromatic heterocondensed polycyclic group.

[0226] In this specification, C5-C 30 A carbocyclic group consists of 5 to 30 carbon atoms as ring-forming atoms. This indicates a saturated cyclic group or an unsaturated cyclic group having C5-C 30 A carbon ring group can be a monocyclic or polycyclic group. It is a ring group. In this specification, "(at least one R 10a Substitute or non-substitute )C5-C 30 "Carbon ring group" is, for example, (at least one R 10a Replace or not replace adamantane group, norbornene group, bicyclo[1.1.1]pentane group, bicyclo[ 2.1.1] Hexane group, bicyclo[2.2.1]heptane group (norbornane group),) Chlo[2.2.2]octane group, cyclopentane group, cyclohexane group, cyclohexene Groups, benzene group, naphthalene group, anthracene group, phenanthrene group, triphenylene group , pyrene group, chrysene group, 1,2,3,4-tetrahydronaphthalene group, cyclopentad It contains groups such as ene groups and fluorene groups.

[0227] In this specification, C1-C 30 A heterocyclic group consists of 1 to 30 carbon atoms as ring-forming atoms. In addition, heteroatoms selected from N, O, P, Si, S, Se, Ge, and B It indicates having at least one saturated cyclic group or an unsaturated cyclic group. C1-C 30 The heterocyclic group is It is 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 10a (Substituted or not substituted) Thiophene group, furan group, pyrrole group, silole group, borol group, phosphole group, selenol Fen group, germol group, benzothiophene group, benzofuran group, indole group, benzo Silole group, benzoborol group, benzophosphole group, benzoselenophene group, benzogel Lumol group, dibenzothiophene group, dibenzofuran group, carbazole group, dibenzosilo dol group, dibenzobolol group, dibenzophosphole group, dibenzoselenophene group, diben Zogermol group, dibenzothiophene 5-oxide group, 9H-fluoren-9-one group, Dibenzothiophene 5,5-dioxide group, azabenzothiophene group, azabenzofuran group, azaindole group, azaindene group, azabenzosilol group, azabenzoborol group azabenzophosphorus group, azabenzoselenophene group, azabenzogermole group, aza Dibenzothiophene group, azadibenzofuran group, azacarbazole group, azafluorene group azadibenzosilol group, azadibenzoborol group, azadibenzophosphole group, aza Dibenzoselenophen group, azadibenzogermol group, azadibenzothiophene 5-oxy Side group, aza-9H-fluoren-9-one group, azadibenzothiophene 5,5-dioxy Side group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, triazine group, quinoli n group, isoquinoline group, quinoxaline group, quinazoline group, phenanthroline group, pyrazol Imidazole group, imidazole group, triazole group, oxazole group, isoxazole group, thiazo Isothiazole group, isothiazole group, oxadiazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzoxazole group, benzothiazole group, benzox Diazole group, benzothiadiazole group, 5,6,7,8-tetrahydroisoquinoline group It contains, for example, 5,6,7,8-tetrahydroquinoline groups.

[0228] As another example, in this specification, "C5-C 30 "Carbon ring group" and "C1-C 30 Hete Examples of "R-ring groups" include i) a first ring, ii) a second ring, and iii) two or more first rings fused together. iv) a condensed ring formed by the condensation of two or more second rings, or v) one or more first rings It includes fused rings in which a ring and one or more secondary rings are fused together. The first ring consists of a cyclopentane group, a cyclopentene group, a furan group, a thiophene group, and pyrrole. Group, silole group, borol group, phosphole group, germole group, selenofen group, oxazo ethyl group, oxadiazole group, oxatriazole group, thiazole group, thiaziazole group Thiatriazole group, pyrazole group, imidazole group, triazole group, tetrazol It is a group, or an azasilol group, The second ring consists of an adamantane group, a norbornane group, a norbornene group, a cyclohexane group, and a cyclohexane group. Chlohexene group, benzene group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, Alternatively, it is a triazine group.

[0229] In this specification, "fluorinated C1-C 60 Alkyl(Also Fluoride C1-C 20 (Alkyl alkyl groups, etc.), Fluoride C3-C 10 Cycloalkyl groups "Fluoride C1-C 10 "Heterocycloalkyl group" and "phenyl fluoride group" are Each is substituted with at least one fluoro group (-F), C1-C 60 Alkyl(or , C1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 hetero This refers to cycloalkyl groups and phenyl groups. For example, "C1 alkyl fluoride (i.e.) "(It is a methyl fluoride group)" includes -CF3, -CF2H, and -CFH2. C1-C 60 Alkyl group (or C1-C fluoride) 20 (Alkyl alkyl groups, etc.), fluoride C3-C 10 Cycloalkyl group, C1-C fluoride 10 "heterocycloalkyl group", also A "phenyl fluoride group" is defined as i) a group in which all hydrogen atoms are replaced by fluoro groups. Fully fluoride C1-C 60 Alkyl alkyl groups (or fully fluorinated C1-C 20 Al Kill groups, etc.), complete fluoride C3-C 10 Cycloalkyl groups, fully fluorinated C1-C 10 Hete ii) a rocycloalkyl group, or a fully fluorinated phenyl group, or contained in each group Not all hydrogen atoms are replaced by fluoro groups; it is partially fluorinated. C1-C 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 Heterocycloalkyl groups, or It is partially composed of phenyl fluoride groups.

[0230] In this specification, "deuterated C1-C 60 Alkyl(Also Deuterated C1-C20 (Alkyl groups, etc.), Deuterated C3-C 10 Cycloalkyl "Base", "Deuterated C1-C 10 "heterocycloalkyl group" and "deuterated phenyl group" Each is a C1-C atom substituted with at least one deuterium atom. 60 Alkyl alkyl group (or C 1-C 20 (Alkyl alkyl groups, etc.), C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycline This refers to C1 alkyl groups and phenyl groups. For example, "deuterated C1 alkyl group (i.e., "Deuterated methyl group)" includes -CD3, -CD2H, and -CDH2, and "he Hydrogenated C3-C 10 An example of a "cycloalkyl group" is, for example, the above chemical formula 10-501. See also: "Deuterated C1-C 60 Alkyl group (or deuterated C1-C 20 alkyl group etc.), Deuterated C3-C 10 Cycloalkyl group, Deuterated C1-C 10 hetero "Cycloalkyl group" or "deuterated phenyl group" i) all hydrogens contained in each group , deuterium-substituted, fully deuterated C1-C 60 Alkyl(or, complete) Fully deuterated C1-C 20 Alkyl groups, etc.), fully deuterated C3-C 10 Cycloalkyl groups , completely deuterated C1-C 10 Heterocycloalkyl groups, or fully deuterated phenyl groups ii) Not all hydrogen atoms in each group are replaced by deuterium. partially deuterated C1-C 60 Alkyl group (or partially deuterated C1 -C 20alkyl 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, the term "((C1-C 20 alkyl)"X" group" refers to a "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 at least one C1- C 20 C3-C substituted with an alkyl group 10 cycloalkyl group, and "(C1-C 20 alkyl)phenyl group" means at least one C1-C 20 phen substituted with an alkyl group yl group. An example of a (C1 alkyl)phenyl group is toluyl gr oup).

[0232] As used herein, "azaindole group, azabenzoborole group, azabenzophospho le group, azaindene group, azabenzosilole group, azabenzogermole group, azabenzothi ophene group, azabenzoselenophene group, azabenzofuran group, azacarbazole group, a zadibenzoborole group, azadibenzophosphole group, azafluorene group, azadibenzosi lole group, azadibenzogermole group, azadibenzothiophene group, azadibenzoseleno phene group, azadibenzofuran group, azadibenzothiophene 5-oxide group, aza-9H -fluorene-9-one group, azadibenzothiophene 5,5-dioxide group" are each respec , which has the same backbone as "indole group, benzoborole group, benzophosphole group, indene group, benzosilo le group, benzogermole group, benzothiophene group, benzoselenophene group, benzofura n group, carbazole group, dibenzoborole group, dibenzophosphole group, fluorene group, di benzosilole group, dibenzogermole group, dibenzothiophene group, dibenzoselenophe ne group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9- one group, dibenzothiophene 5,5-dioxide group", means a heterocycle in which at least one of the carbons forming these rings is substituted with nitrogen .

[0233] substituted C5-C 30 carbocyclic group, substituted C2-C 30 heterocyclic group, substituted C 1-C 60 alkyl group, substituted C2-C 60 alkenyl group, substituted C2-C 60 alkynyl group, substituted C1-C 60 alkoxy group, substituted C1-C 60 alkyl thio group, substituted C1-C 60 alkylthio group, substituted C3-C 10 cycloalkyl group, substituted C1-C 10 heterocycloalkyl group, substituted C3-C 10 cyclo alkenyl group, substituted C1-C 10 heterocycloalkenyl group, substituted C6-C 60 aryl group, substituted C7-C 60 alkylaryl group, substituted C6-C 60 aryloxy group, substituted C6-C 60 arylthio group, substituted C1-C​60 He Telolaryl group, substituted C2-C 60 Alkyl heteroaryl group, substituted monovalent non The substituents of the aromatic condensed polycyclic group and the substituted monovalent non-aromatic heterocondensed polycyclic group are, respectively Independent, Deuterium, -F, -Cl, -Br, -I, -CD3, -CD2H, -CDH2, -CF3 -CF2H, -CFH2, hydroxyl group, cyano group, nitro group, amidino group, hydra A din group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphate group or The salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkini 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, hydra A din group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphate group or The salt, C3-C 10 Cycloalkyl groups, C1-C 10 Heterocycloalkyl groups, C3 -C 10 Cycloalkenyl group, C1-C 10 Heterocycloalkenyl group, C6-C 60 a Reel base, C7-C 60 Alkylaryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C 60 Heteroaryl group, C2-C 60 Alkyl heteroant -N(Q) 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 )(Q 17 ), -P(= O)(Q 18 )(Q 19 ), -P(Q 18 )(Q 19 ), or any combination thereof C1-C, which was replaced by 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Al Quinyl 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, hydra A din group, a hydrazone group, a carboxylic acid group or its salt, a sulfonic acid group or its salt, a phosphate group or The salt, C1-C 60 Alkyl alkyl group, C2-C 60 Alkenyl group, C2-C 60 Alkini group, C1-C 60 Alkoxy group, C1-C 60 Alkylthio group, C3-C 10 Cycloa Lukyl group, C1-C 10 Heterocycloalkyl groups, C3-C 10 Cycloalkenyl group, C 1-C 10 Heterocycloalkenyl group, C6-C 60 Aryl group, C7-C 60 Alkyl Aryl group, C6-C 60 Aryloxy group, C6-C 60 Arylthio group, C1-C6 0 heteroaryl group, C2-C 60 Alkyl heteroaryl group, monovalent non-aromatic condensed polycyclic group , a monovalent non-aromatic hetero-fused polycyclic group, -N(Q 21 )(Q 22 ), -Si(Q 23 )(Q2 4)(Q 25 ), -B(Q 26 )(Q 27 ), -P(=O)(Q 28 )(Q 29 ), -P (Q 28 )(Q 29 ), or C3- which is substituted or unsubstituted with any combination thereof; C 10 cycloalkyl group, C1-C 10 heterocycloalkyl group, C3-C 10 cycloal kenyl 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-ar omatic fused polycyclic group, or a monovalent non-aromatic hetero-fused 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 is any combination thereof; that is.

[0234] In the present specification, Q1 to Q9, Q 11 to Q 19 , Q 21 to Q29 , and Q 31 ~Q 39 These are, independently, hydrogen; deuterium; -F; -Cl; -Br; -I; hydro Xyl group; cyano group; nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid Group or salt thereof; sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C1-C 60 a Lucyl group, C6-C 60 Substitution or absence of aryl groups, or any combination thereof. Replacement C1-C 60 Alkyl 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 groups; C3-C 10 Cycloalkenyl group; C1-C 10 Heterocycloalkenyl group; deuterium, C1-C 60 Alkyl alkyl group, C6-C 60 Ally C6-C groups, or any combination thereof, are substituted or unsubstituted. 60 Aryl group; C6-C 60 Aryloxy group; C6-C 60 Arylthio group; C1-C 60 Heterozygous ants It is a ring 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 BiQ 31 ~Q 39 Each of them operates independently. -CH3, -CD3, -CD2H, -CDH2, -CH2CH3, -CH2CD3, - CH2CD2H, -CH2CDH2, -CHDCH3, -CHDCD2H, -CHDCD H2, -CHDCD3, -CD2CD3, -CD2CD2H, or -CD2CDH2; or iha Deuterium, C1-C 10 Substituted with alkyl groups, phenyl groups, or any combination thereof. Or unsubstituted n-propyl group, isopropyl group, n-butyl group, sec-butyl group isobutyl group, tert-butyl group, n-pentyl group, tert-pentyl group, neo-pentyl group pentyl group, isopentyl group, sec-pentyl group, 3-pentyl group, sec-isopentyl It is a phenyl group, a biphenyl group, or a naphthyl group.

[0236] The following are examples of synthesis and embodiments, illustrating a compound and an organic light-emitting element according to one embodiment of the present invention. To explain in more detail, the present invention is not limited to the following synthesis examples and embodiments. i. In the following example of synthesis, in the expression "'B' was used instead of 'A'", The amount of "B" used and the amount of "A" used are the same on a molar equivalent basis.

[0237] [Examples]

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

[0239] [ka]

[0240] Compound 317-1 (7.9g, 11.0mmol), K2PtCl4 (5.5g, 13 Mix 0.2 mmol) and 100 mL of acetic acid, and stir under reflux for 18 hours to allow the reaction to proceed. The temperature was lowered to room temperature. The resulting solid was filtered, and methylene chloride (MC) and Column chromatography was performed using hexane, and compound 317 was analyzed at 4.2g (42%). The yield was obtained. 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 (7.9g, 11.1mmol), K2PtCl4 (5.5g, 13 Mix 0.3 mmol) and 100 mL of acetic acid, and allow the reaction to proceed by stirring under reflux for 18 hours. The temperature was lowered to room temperature. The resulting solid was filtered and then mixed with methylene chloride and hexane. Column chromatography was performed using [a specific method / tool], yielding 3.8g of compound 351 (38% yield). I obtained it. HRMS (MALDI) calcd for C 51 H 37 N3OPt:m / z 9 02.2584 found:902.2589

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

[0245] [ka]

[0246] Compound 592-1 (7.9g, 11.1mmol), K2PtCl4 (5.5g, 13 Mix 0.3 mmol) and 100 mL of acetic acid, and allow the reaction to proceed by stirring under reflux for 18 hours. The temperature was lowered to room temperature. The resulting solid was filtered and then mixed with methylene chloride and hexane. Column chromatography was performed using [a specific method / tool], yielding 3.1g of compound 592 (31% yield). I obtained it. 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 (3.9g, 5.9mmol), K2PtCl4 (3.0g, 7.1 The mmol) and 50 mL of acetic acid were mixed and stirred under reflux for 18 hours to allow the reaction to proceed, and then left at room temperature. The temperature was lowered. The resulting solid was filtered, and methylene chloride and hexane were used. Column chromatography was then performed, yielding 2.1 g of compound 741 (42% yield). . HRMS (MALDI) calcd for C 47 H 40 N2OPt:m / z 8 43.2788 found:843.2795

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

[0251] [ka]

[0252] Synthesis Example 1 is similar to Synthesis Example 1, except that compound A-1 was used instead of compound 317-1. Using the same method, 0.5 g of compound A (40% yield) was obtained. HRMS (MALDI) calcd for C 43 H 45 N3OPt:m / z 8 14.3210 found:814.3205

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

[0254] [ka]

[0255] Synthesis Example 2 is similar to Synthesis Example 2, except that compound B-1 was used instead of compound 351-1. Using the same method, 0.4 g of compound B (36% yield) was obtained. HRMS (MALDI) calcd for C 42 H 27 N3OPt:m / z 7 84.1802 found:784.1796

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

[0257] [ka]

[0258] Synthesis Example 3, except that compound C-1 was used instead of compound 592-1. Using the same method, 0.6 g of compound C (45% yield) was obtained. HRMS (MALDI) calcd for C 42 H 39 N3OPt:m / z 7 96.2741 found:796.2744

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

[0260] [ka]

[0261] Synthesis Example 4, except that compound D-1 was used instead of compound 741-1. Using the same method, 0.2 g of compound D (22% yield) was obtained. HRMS (MALDI) calcd for C 38 H30N2OPt:m / z 7 25.2006 found:725.2001

[0262] Example 1

[0263] As the anode, a glass substrate patterned with ITO is used, 50mm x 50mm x 0 Cut into 0.5mm pieces, and soak in isopropyl alcohol and pure water for over 5 minutes each. After ultrasonic cleaning, the material is exposed to ozone by irradiating it with ultraviolet light for 30 minutes for further cleaning, and then transferred to a vacuum deposition apparatus. It was established.

[0264] The following compounds HT3 and F6-TCNNQ were applied to the top of the anode in a weight ratio of 98:2. A 100 Å thick hole-injection layer is formed by co-deposition of the empty space, and the following compound HT3 is deposited on top of the hole-injection layer. A hole transport layer with a thickness of 1,350 Å was formed by vacuum deposition. The following compound was deposited on top of the hole transport layer. H-H1 was deposited using vacuum deposition to form an electron stoppage layer with a thickness of 300 Å.

[0265] Next, the following compounds H-H1, H-H2, and compound 317 (D) are placed on the electron blocking layer. Panto(s) was co-deposited in a weight ratio of 42.5:42.5:15 to form a 400 Å thick luminescent layer. did.

[0266] Subsequently, the compounds ET3 and ET-D1 are co-evaporated onto the upper part of the light-emitting layer in a 50:50 volume ratio. A 350 Å thick electron transport layer is formed, and the following compound ET-D1 is placed on top of the electron transport layer under vacuum. Deposition was performed to form an electron injection layer with a thickness of 10 Å, and Al was vacuum deposited on top of the electron injection layer, 1,00 An organic light-emitting device was fabricated by forming a cathode with a thickness of 0 Å.

[0267] [ka]

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

[0269] When forming the light-emitting layer, instead of compound 317 above, use the compound listed in Table 2 below as a dopant. Except for the fact that the compounds used were different, the same method as in Example 1 was used. We fabricated an organic light-emitting device.

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

[0271] For each of the organic light-emitting elements produced in Examples 1-4 and Comparative Examples A-D above, Dynamic voltage, external quantum efficiency Maximum value (Max EQE) (%), and lifetime (LT) 97 )(time:hr) evaluate and The results are shown in Table 2 below. The evaluation equipment used was a current / voltmeter (Keithley 2400). ) and a luminance meter (Minolta Cs-1000A) were used to determine the lifespan (LT 97 )(18 (At 0,000 nits) it takes time to reach 97% brightness compared to the initial brightness of 100%. Time (hr) was evaluated and recorded as a relative value (%).

[0272] [Table 2]

[0273] [ka]

[0274] From Table 2 above, each of the organic light-emitting elements of Examples 1 to 4 is the same as the organic light-emitting elements of Comparative Examples A to D. Compared to each of the children, it has improved external quantum efficiency and improved lifetime characteristics. This can be confirmed.

[0275] Although embodiments of the present invention have been described in detail above, the present invention is not limited to the embodiments described above. This invention is not intended to be modified in any way, and can be modified and implemented in various ways without departing from the technical concept of the present invention. This is possible. [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 the following chemical formula 1. 【Chemistry 1】 In the aforementioned chemical formula 1, M is a transition metal. In the aforementioned chemical formula 1, X １ ~X ４ Each of them is independently either C or N, In the aforementioned chemical formula 1, X ５ is O, S, N(R'), C(R')(R''), or C(=O) And, In the aforementioned chemical formula 1, X ５ The bond between and M is a covalent bond. X ２ The combination of X and M. ３ The combination of M and X ４ One of the bonds between and M is a covalent bond. It is a combination, and the remaining two are coordinate covalent bonds. In the above Chemical Formula 1, ring CY １ to ring CY ４ are each independently C ５ -C ３０ carbocyclic group or C １ -C ３０ It is a heterocyclic group, In the chemical formula 1, T １ ~T ４ These are, independently, single bonds, double bonds, and *-N( R ５ａ )-*’、*-B(R ５ａ )-*’、*-P(R ５ａ )-*’、*-C(R ５ａ ) (R ５ｂ )-*’、*-Si(R ５ａ )(R ５ｂ )-*’、*-Ge(R ５ａ )(R ５ｂ )-*', *-S-*', *-Se-*', *-O-*', *-C(=O)-*', *- S(=O)-*’、*-S(=O) ２ -*’、*-C(R ５ａ )=*’、*=C(R ５ａ )-*’、*-C(R ５ａ )=C(R ５ｂ )-*’、*-C(=S)-*’、*-C≡C - *', at least one R １０ａ Substitute or non-substitute C ５ -C ３０ Carbon ring group, or At least one R １０ａ Substitute or non-substitute C １ -C ３０ It is a heterocyclic group, In the aforementioned chemical formula 1, n1 to n4 are each independently 0 or 1, but n1 to n Three or more of the four are equal to one. In the above chemical formula 1, if n1 is 0, T １ If it does not exist and n2 is 0, then T ２ If it does not exist and n3 is 0, then T ３ If it does not exist and n4 is 0, then T ４ teeth, It does not exist, In the aforementioned chemical formula 1, Z １ ~Z ４ Each of these is an independent group represented by the following chemical formula 51. can be, 【Chemistry 51】 In the aforementioned chemical formula 1, d1 to d4 are each independent integers from 0 to 20. In the aforementioned chemical formulas 1 and 51, L １ ~L ４ , and L ５１ Each is independent, single bond , at least one R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least Both are R １０ａ Substitute or non-substitute C １ -C ３０ It is a heterocyclic group, In the aforementioned chemical formulas 1 and 51, b1 to b4 and b51 are each independently 1 to 10 It is an integer, In the aforementioned chemical formulas 1 and 51, R １ ~R ４ , R ５ａ , R ５ｂ , R', R'', and Q ５１ No To Q ５３ These are, independently, the group represented by the chemical formula 51, hydrogen, deuterium, -F, - Cl, -Br, -I, -SF ５ hydroxyl group, cyano group, nitro group, amidino group, hi Drazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, phosphoric acid C group or its salt, substituted or unsubstituted C １ -C ６０ Alkyl, substituted or unsubstituted C ２ -C ６０ Alkenyl group, substituted or unsubstituted C ２ -C ６０ Alkynyl group, substitution or is a non-substitutive C １ -C ６０ alkoxy group, substituted or unsubstituted C １ -C ６０ Alkylthio C as a base, substituted, or unsubstituted component ３ -C １０ Cycloalkyl groups, substituted or unsubstituted C １ - C １０ Heterocycloalkyl groups, substituted or unsubstituted C ３ -C １０ Cycloalkenyl group , substitution or non-substitution of C １ -C １０ Heterocycloalkenyl group, substituted or unsubstituted C ６ -C ６０ Aryl group, substituted or unsubstituted C ７ -C ６０ Alkylaryl group, substitution Or non-substituted C ６ -C ６０ Aryloxy group, substituted or unsubstituted C ６ -C ６０ a C with a reelthio group, substituted or unsubstituted １ -C ６０ Heteroaryl group, substitution or non-substitution Exchange C ２ -C ６０ Alkyl heteroaryl group, substituted or unsubstituted monovalent non-aromatic condensate poly Ring group, substituted or unsubstituted monovalent non-aromatic heterocondensed polycyclic group, -N(Q １ ) (Q ２ ), - Si(Q ３ )(Q ４ )(Q ５ )、-Ge(Q ３ )(Q ４ )(Q ５ )、-B(Q ６ )(Q ７ ), -P(=O)(Q ８ ) (Q ９ ), or -P(Q ８ ) (Q ９ ) However, Q ５１ ~Q ５３ Each of these is not a group represented by the chemical formula 51, Q of the aforementioned chemical formula 51 ５１ ~Q ５３ At least one of them is a substitution or non-substitution C ６ -C ６０ Aryl group, substituted or unsubstituted C １ -C ６０ Heteroaryl group, substitution Alternatively, an unsubstituted monovalent non-aromatic condensed polycyclic group, or a substituted or unsubstituted monovalent non-aromatic heterocyclic group. It is a condensed polycyclic group, c1 to c4 and a1 to a4 of the aforementioned chemical formula 1 are each independently of a range of 0 to 20. It is a number, In the aforementioned chemical formula 51, c51 is an integer between 1 and 20. The aforementioned chemical formula 1 satisfies at least one of the following conditions 1 and 2. 、 <Condition 1> In the aforementioned chemical formula 1, the sum of d1 to d4 is 1 or greater. <Condition 2> T of the above chemical formula 1 １ ~T ４ At least one of them 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 )-*’、*-C( R ５ａ ) = *', * = C (R ５ａ )-*', or *-C(R ５ａ ) = C(R ５ｂ ) - *' And the R ５ａ and R ５ｂ At least one of them is represented by the chemical formula 51. It is the basis In the aforementioned chemical formula 1, multiple R １ Two or more of them are selectively coupled to each other, and at least one Horn R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １ ０ａ Substitute or non-substitute C １ -C ３０ Forming a heterocyclic group, In the aforementioned chemical formula 1, multiple R ２ Two or more of them are selectively coupled to each other, and at least one Horn R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １ ０ａ Substitute or non-substitute C １ -C ３０ Forming a heterocyclic group, In the aforementioned chemical formula 1, multiple R ３ Two or more of them are selectively coupled to each other, and at least one Horn R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １ ０ａ Substitute or non-substitute C １ -C ３０ Forming a heterocyclic group, In the aforementioned chemical formula 1, multiple R ４ Two or more of them are selectively coupled to each other, and at least one Horn R １０ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １ ０ａ Substitute or non-substitute C １ -C ３０ Forming a heterocyclic group, R １ ~R ４ Two or more of R １ ~R ４ one of the following, and R ５ａ , R １ ~R ４ one of the following, and R ５ｂ , or R ５ａ and R ５ｂ Each of them selectively binds to the others. And at least one R １０ａ Substitute or non-substitute C ５ -C ３０ Carbon ring group, or a small number Even if it's just one R １０ａ Substitute or non-substitute C １ -C ３０ Forming a heterocyclic group, The aforementioned R １０ａ The explanation regarding the above R １ Refer to the explanation regarding this matter. * and *' are bonding sites with adjacent atoms, respectively. The substituted C １ -C ６０ Alkyl alkyl group, substituted C ２ -C ６０ Alkenyl group, substitution C ２ -C ６０ Alkynyl group, substituted C １ -C ６０ Alkoxy group, substituted C １ -C ６０ Alkylthio group, substituted C ３ -C １０ Cycloalkyl groups, substituted C １ -C １０ Heterocycloalkyl groups, substituted C ３ -C １０ Cycloalkenyl group, substituted C １ -C １０ heterocycloalkenyl group, substituted C ６ -C ６０ Aryl group, substitution C ７ -C ６０ Alkylaryl group, substituted C ６ -C ６０ Aryloxy group, Replaced C ６ -C ６０ Arylthio group, substituted C １ -C ６０ heteroaryl group, substitution C ２ -C ６０ Alkyl heteroaryl groups, substituted monovalent non-aromatic condensed polycyclic groups, and The substituents of the substituted monovalent non-aromatic heterocondensed polycyclic group are Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino Group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, Phosphate group or its salt, C １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６ ０ Alkynyl group, or C １ -C ６０ Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino Group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, Phosphate group or its salt, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non-aromatic heterocondensed polycyclic group 、-N(Q １１ )(Q １２ )、-Si(Q １３ )(Q １４ )(Q １５ )、-Ge(Q １３ )(Q １４ )(Q １５ )、-B(Q １６ )(Q １７ )、-P(=O)(Q １８ )(Q １９ ), -P(Q １８ ) (Q １９ C, replaced by any combination thereof. １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６０ Alkynyl group, or C １ -C ６０ Alkoxy group; Deuterium, -F, -Cl, -Br, -I, -CD ３ , -CD ２ H, -CDH ２ , -CF ３ , -CF ２ H, -CFH ２ hydroxyl group, cyano group, nitro group, amino group, amidino Group, hydrazine group, hydrazone group, carboxylic acid group or its salt, sulfonic acid group or its salt, Phosphate group or its salt, C １ -C ６０ alkyl group, C ２ -C ６０ Alkenyl group, C ２ -C ６ ０ Alkynyl group, C １ -C ６０ Alkoxy group, C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloalkyl groups, C ３ -C １０ Cycloalkenyl group, C １ -C １０ Heterozy Chloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group, C １ -C ６０ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, monovalent non Aromatic heterocondensed polycyclic group, -N(Q ２１ ) (Q ２２ ), -Si(Q ２３ ) (Q ２４ ) (Q ２５ )、-Ge(Q ２３ )(Q ２４ )(Q ２５ )、-B(Q ２６ )(Q ２７ )、-P(= O) (Q ２８ ) (Q ２９ ), -P(Q ２８ ) (Q ２９ ), or any combination thereof Substituted or not substituted by C ３ -C １０ Cycloalkyl groups, C １ -C １０ Heterocycloa Lukil group, C ３ -C １０ Cycloalkenyl group, C １ -C １０ heterocycloalkenyl group, C ６ -C ６０ Aryl group, C ６ -C ６０ Aryloxy group, C ６ -C ６０ Arylthio group , C １ -C ６０ Heteroaryl group, monovalent non-aromatic condensed polycyclic group, or monovalent non-aromatic heterocyclic group Combined polycyclic group; -N(Q ３１ )(Q ３２ ), - Yes (Q ３３ )(Q ３４ )(Q35), -Ge (Q ３３ )(Q ３４ )(Q ３５ )、-B(Q ３６ )(Q ３７ )、-P(=O)(Q ３８ )(Q ３９ ), or -P(Q ３８ ) (Q ３９ ); or Any combination of those; The aforementioned Q １ ~Q ９ Q １１ ~Q １９ Q ２１ ~Q ２９ , and Q ３１ ~Q ３９ teeth, Each independently represents: hydrogen; deuterium; -F; -Cl; -Br; -I; hydroxyl group; shea nitro group; amidino group; hydrazine group; hydrazone group; carboxylic acid group or its salt; Sulfonic acid group or salt thereof; phosphate group or salt thereof; deuterium, C １ -C ６０ alkyl group, C ６ -C ６０ A carbon atom substituted or unsubstituted with an aryl group, or any combination thereof. １ -C ６ ０ Alkyl alkyl group; C ２ -C ６０ Alkenyl group; C ２ -C ６０ Alkynyl group; C １ -C ６０ a Glucoxyl group; C ３ -C １０ Cycloalkyl group; C １ -C １０ Heterocycloalkyl group; C ３ -C １０ Cycloalkenyl group; C １ -C １０ Heterocycloalkenyl group; deuterium, C １ -C ６０ alkyl group, C ６ -C ６０ Substitution with an aryl group, or any combination thereof Or non-substituted C ６ -C ６０ Aryl group; C ６ -C ６０ Aryloxy group; C ６ -C ６０ Arylthio group; C １ -C ６０ Heteroaryl group; monovalent non-aromatic condensed polycyclic group; or monovalent It is a non-aromatic heterocondensed polycyclic group.

2. The claim according to the above chemical formula 1, wherein M is Pt, Pd, or Au. Organometallic compounds.

3. The aforementioned X ２ N is, The aforementioned ring CY ２ teeth, Benzimidazole group, pyridine group, pyrimidine group, pyridazine group, pyrazine group, tri Adin group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group; or Cyclohexane group, cyclohexene group, norbornane group, or any combination thereof The following are condensed: benzimidazole group, pyridine group, pyrimidine group, pyridazine group, Radin group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazori The organometallic compound according to claim 1, characterized by being an 'n' group.

4. In the chemical formula 1, T １ and T ２ It is a single bond, T ３ This is a single bond, *-N(R) ５ ａ )-*’、*-B(R ５ａ )-*’、*-P(R ５ａ )-*’、*-C(R ５ａ )(R ５ｂ )-*’、*-Si(R ５ａ )(R ５ｂ )-*’、*-Ge(R ５ａ )(R ５ｂ )- The organic gold according to claim 1, characterized in that it is *', *-S-*', or *-O-*'. genus compound.

5. The claim is characterized in that, in the aforementioned chemical formula 1, n1 to n3 are 1 and n4 is 0. Organometallic compounds as described in item 1.

6. It is characterized by satisfying at least one of the following conditions: <Condition 1A> and <Condition 2A>. The organometallic compound according to claim 1. <Condition 1A> In the aforementioned chemical formula 1, i) d1 is 1, and d2, d3, and d4 are each 0, ii) d2 is 1, and each of d1, d3, and d4 is 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) Are d2 and d3 each 1, and d1 and d4 each 0? , or vii) d2 and d4 are each 1, and d1 and d3 are each 0. <Condition 2A> In the aforementioned chemical formula 1, n3 is 1. i) T ３ is, *-N(R ５ａ )-*', *-B(R ５ａ )-*', *-P(R ５ａ ) - *', *-C(R ５ａ ) = *', or * = C (R ５ａ ) - *' and the above R ５ａ That is, It is a group represented by chemical formula 51, or ii)T ３ は、*-C(R ５ａ )(R ５ｂ )-*’、*-Si(R ５ａ )(R ５ｂ )- *', *-Ge(R ５ａ ) (Caution ５ｂ )-*', or *-C(R ５ａ ) = C(R ５ｂ ) - * ' and the R ５ａ and R ５ｂ At least one of them is represented by the chemical formula 51. It is a base.

7. In the aforementioned chemical formula 51, *-C(Q ５１ ) (Q ５２ ) (Q ５３ The group represented by ) is the following chemical The present invention is characterized in that it is a group represented by one of formulas 51-1 to 51-25. The organometallic compounds listed. 【Chemistry (51-1)-(51-25)】 In the aforementioned chemical formulas 51-1 to 51-25, Q ５１ and Q ５２ The explanations for each of them are as follows: Refer to the section described in Claim 1, Q ６１ ~Q ６６ The explanations for each of them are In each of the claims in claim 1, R １０ａ Refer to the explanation regarding Q ６１ ~Q ６５ of Each is not hydrogen, and * is in the aforementioned chemical formula 51, L ５１ This is a linked site.

8. In the aforementioned chemical formula 51, L ５１ The organic compound according to claim 1, characterized in that it is a single bond. metal compounds.

9. The group represented by the aforementioned chemical formula 51 is one of the following chemical formulas 51(1) to 51(19). The organometallic compound according to claim 1, characterized in that it is a represented group. 【Chemistry 51(1)-51(19)】 In the chemical formulas 51(1) to 51(19), T １１ ~T １５ Each of the above chemical formulas 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 The explanation regarding R is as follows in claim 1. １ Refer to the explanation regarding this, where * indicates a bonding site with an adjacent atom.

10. In the aforementioned chemical formula 1, n1 is 1, and n4 is 0. 【Chemical ZCY1】 The groups represented by the following chemical formulas are CY1-1 to CY1-18, and ZCY1-1 to The organic according to claim 1, characterized in that it is a group represented by one of ZCY1-32. metal compounds. 【Chemistry (CY1-1)-(CY1-18)】 [Chemical (ZCY1-1)-(ZCY1-32)] The aforementioned chemical formulas CY1-1 to CY1-18, and the aforementioned chemical formulas ZCY1-1 to ZCY1-32 in, X １ For further explanation, please refer to the section described in claim 1. R １１ ~R １４ The explanation for each of these is as follows in claim 1, R １ Explanation regarding Refer to R １１ ~R １４ Each of them is not hydrogen, Z １１ ~Z １４ The explanation for each of these is as follows in claim 1, Z １ Explanation regarding Refer to, * represents chemical formula 1, X ５ It is a combined site with, *' is in chemical formula 1, T １ This is a linked site.

11. In the aforementioned chemical formula 1, n1 and n2 are each 1, 【ZCY2】 The groups represented by the following chemical formulas are CY2-1 to CY2-16, and ZCY2-1 to The organic according to claim 1, characterized in that it is a group represented by one of ZCY2-19. metal compounds. 【Chemistry (CY2-1)-(CY2-16)】 【Chemistry (ZCY2-1)-(ZCY2-19)】 The aforementioned chemical formulas CY2-1 to CY2-16, and the aforementioned chemical formulas ZCY2-1 to ZCY2-19 in, X ２ For further explanation, please refer to the section described in claim 1. X ２９ is O, S, N-[(L ２ ) ｂ２ - (R ２ ) ｃ２ ], C (R ２９ａ ) (Caution ２９ｂ ), or Si (R ２９ａ ) (Caution ２９ｂ ) and L ２ , b2, R ２ The explanations for each of , and c2 are as described in claim 1. Refer to, Z ２１ ~Z ２４ The explanation for each of these is as follows in claim 1, Z ２ Explanation regarding Refer to, R ２１ ~R ２３ , R ２９ａ , and R ２９ｂ A description of each of these is provided in Claim 1. And, R ２ Refer to the explanation regarding R ２１ ~R ２３ Each of them is not hydrogen, *' is in chemical formula 1, T １ It is a combined site with, * represents the bonding site with M in chemical formula 1. * represents chemical formula 1, T ２ This is a linked site.

12. In the aforementioned chemical formula 1, n2 and n3 are each 1, 【ZCY3】 The groups represented by the following chemical formulas are CY3-1 to CY3-13, and ZCY3-1 to The organic according to claim 1, characterized in that it is a group represented by one of ZCY3-12. metal compounds. 【Chemistry (CY3-1)-(CY3-13)】 [Chemical (ZCY3-1)-(ZCY3-12)] The aforementioned chemical formulas CY3-1 to CY3-13, and the aforementioned chemical formulas ZCY3-1 to ZCY3-12 in, X ３ For further explanation, please refer to the section described in claim 1. X ３９ is O, S, N-[(L ３ ) ｂ３ - (R3) ｃ３ ], C (R ３９ａ ) (Caution ３９ｂ ), or Si (R ３９ａ ) (Caution ３９ｂ ) and L ３ b3, R ３ The explanations for each of , and c3 are as described in claim 1. Refer to, R ３１ ~R ３３ , R ３９ａ and R ３９ｂ The explanations for each of these are provided in Claim 1. R ３ Refer to the explanation regarding R ３１ ~R ３３ Each of them is not hydrogen, Z ３１ ~Z ３３ The explanation for each of these is as follows in claim 1, Z ３ Explanation regarding Refer to, * represents chemical formula 1, T ２ It is a combined site with, * represents the bonding site with M in chemical formula 1. *' is in chemical formula 1, T ３ This is a linked site.

13. In the aforementioned chemical formula 1, n3 is 1, and n4 is 0. 【Chemical ZCY4】 The groups represented by the following chemical formulas are CY4-1 to CY4-16, and ZCY4-1 to The organic according to claim 1, characterized in that it is a group represented by one of ZCY4-32. metal compounds. [Chemical Formula (CY4-1)-(CY4-16)] [Chemical Formula (ZCY4-1)-(ZCY4-32)] The aforementioned chemical formulas CY4-1 to CY4-16, and the aforementioned chemical formulas ZCY4-1 to ZCY4-32 in, X ４ For further explanation, please refer to the section described in claim 1. R ４１ ~R ４４ The explanation for each of these is as follows in claim 1, R ４ Explanation regarding Refer to R ４１ ~R ４４ Each of them is not hydrogen, Z ４１ ~Z ４４ The explanation for each of these is as follows in claim 1, Z ４ Explanation regarding Refer to, *' is in chemical formula 1, T ３ It is a combined site with, * represents the bonding site with M in chemical formula 1.

14. The product according to claim 1, characterized by being represented by one of the following chemical formulas 1-1 to 1-4. Organometallic compounds. 【Chemistry (1-1)-(1-4)】 In the aforementioned chemical formulas 1-1 to 1-4, M, X １ ~X ５ , T ２ and T ３ The explanations for each of these are as described in claim 1. Refer to the source, 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 １４ The explanation for each of these is as follows in claim 1, R １ Explanation regarding Refer to, Z １１ ~Z １４ The explanation for each of these is as follows in claim 1, Z １ Explanation regarding Refer to, R １１ ~R １４ Two or more of these are selectively coupled to each other, and at least one R １０ ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Replace with Or non-substituted C １ -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 is O, S, N-[(L ２ ) ｂ２ - (R ２ ) ｃ２ ], C (R ２９ａ ) (Caution ２９ｂ ), or Si (R ２９ａ ) (Caution ２９ｂ ) and L ２ , b2, R ２ The explanations for each of , and c2 are as described in claim 1. Refer to, R ２１ ~R ２３ , R ２９ａ , and R ２９ｂ A description of each of these is provided in Claim 1. And, R ２ Refer to the explanation regarding this matter. Z ２１ ~Z ２４ The explanation for each of these is as follows in claim 1, Z ２ Explanation regarding Refer to, R ２１ ~R ２３ Two or more of these are selectively coupled to each other, and at least one R １０ ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Replace with Or non-substituted C １ -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 The explanation for each of these is as follows in claim 1, R ３ Explanation regarding Refer to, Z ３１ ~Z ３３ The explanation for each of these is as follows in claim 1, Z ３ Explanation regarding Refer to, R ３１ ~R ３３ Two or more of these are selectively coupled to each other, and at least one R １０ ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Replace with Or non-substituted C １ -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 The explanation for each of these is as follows in claim 1, R ４ Explanation regarding Refer to, Z ４１ ~Z ４４ The explanation for each of these is as follows in claim 1, Z ４ Explanation regarding Refer to, R ４１ ~R ４４ Two or more of these are selectively coupled to each other, and at least one R １０ ａ Substitute or non-substitute C ５ -C ３０ A carbon ring group, or at least one R １０ａ Replace with Or non-substituted C １ -C ３０ Forming a heterocyclic group, Each of the above chemical formulas 1-1 and 1-2 is Z １１ ~Z １４ One of them, Z ２１ No To Z ２３ One of them, Z ３１ ~Z ３３ One of them, Z ４１ ~Z ４４ one of , or any combination thereof, In the above chemical formulas 1 and 4, R ５ａ This is the group represented by the chemical formula 51.

15. i) Represented by the chemical formula 1-1 or 1-2, where the chemical formulas 1-1 and 1-2 are as follows: Whether at least one of the following conditions (1) to (3) is satisfied, ii) Represented by the above chemical formula 1-3 or 1-4, or iii) Represented by the chemical formula 1-3 or 1-4, wherein the chemical formulas 1-3 and 1-4 are as follows: A contract that satisfies at least one of the following conditions (1) to (3) The organometallic compound described in item 14. <Condition (1)> X ２２ is C(Z ２２ ) <Condition (2)> X ３２ is C(Z ３２ ) <Condition (3)> X ４３ is C(Z ４３ )

16. 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 layer contains one or more organometallic compounds as described in any one of claims 1 to 15. An organic light-emitting element characterized by [something].

17. The first electrode is an anode, The second electrode is a cathode, The organic layer comprises a hole transport region disposed between the first electrode and the light-emitting layer, and the light-emitting layer The electron transport region is further located between the optical layer and the second electrode, The hole transport region is a hole injection layer, a hole transport layer, an electron blocking layer, or any combination thereof. Including the combination, The electron transport region is a hole blocking layer, an electron transport layer, an electron injection layer, or any combination thereof. The organic light-emitting element according to claim 16, characterized by including a combination.

18. The organometallic compound is characterized in that it is included in the light-emitting layer as described in 16. Light-emitting element.

19. The light-emitting layer further includes a host, The host content is greater than the organometallic compound content, characterized in that 1 The organic light-emitting device described in 8.

20. An electron light-emitting element characterized by comprising an organic light-emitting element according to any one of claims 16 to 19. Device.

Images