WO2022116733A1 - 一种金属络合物及其应用 - Google Patents
一种金属络合物及其应用 Download PDFInfo
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- WO2022116733A1 WO2022116733A1 PCT/CN2021/125928 CN2021125928W WO2022116733A1 WO 2022116733 A1 WO2022116733 A1 WO 2022116733A1 CN 2021125928 W CN2021125928 W CN 2021125928W WO 2022116733 A1 WO2022116733 A1 WO 2022116733A1
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- WIPO (PCT)
- Prior art keywords
- substituted
- unsubstituted
- alkyl
- metal complex
- compound
- Prior art date
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- 150000004696 coordination complex Chemical class 0.000 title claims abstract description 41
- 239000000463 material Substances 0.000 claims abstract description 28
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 36
- 229910052799 carbon Inorganic materials 0.000 claims description 32
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 29
- -1 phosphino group Chemical group 0.000 claims description 25
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 24
- 229910052805 deuterium Inorganic materials 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 125000004404 heteroalkyl group Chemical group 0.000 claims description 16
- 239000010410 layer Substances 0.000 claims description 16
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 15
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 239000003446 ligand Substances 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 150000002527 isonitriles Chemical class 0.000 claims description 9
- 150000002825 nitriles Chemical class 0.000 claims description 9
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 239000012044 organic layer Substances 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 6
- 238000002347 injection Methods 0.000 claims description 6
- 239000007924 injection Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- FVZVCSNXTFCBQU-UHFFFAOYSA-N phosphanyl Chemical group [PH2] FVZVCSNXTFCBQU-UHFFFAOYSA-N 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 150000001924 cycloalkanes Chemical class 0.000 claims description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000005104 aryl silyl group Chemical group 0.000 claims description 3
- 125000004104 aryloxy group Chemical group 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 229910052711 selenium Inorganic materials 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims 1
- 238000000859 sublimation Methods 0.000 abstract description 28
- 230000008022 sublimation Effects 0.000 abstract description 28
- 230000003287 optical effect Effects 0.000 abstract description 3
- 229920001621 AMOLED Polymers 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 121
- 230000015572 biosynthetic process Effects 0.000 description 79
- 238000003786 synthesis reaction Methods 0.000 description 78
- 238000000746 purification Methods 0.000 description 45
- 238000000034 method Methods 0.000 description 30
- 239000002994 raw material Substances 0.000 description 30
- 238000001819 mass spectrum Methods 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 15
- 239000007787 solid Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 229940126214 compound 3 Drugs 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- 238000005401 electroluminescence Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 229940125904 compound 1 Drugs 0.000 description 4
- 101100457453 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) MNL1 gene Proteins 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ATEPEOFRDZUVAG-UHFFFAOYSA-N ClP(C1(C(C=C(C=C1)N(C)C)C(C)(C)C)C(C)(C)C)Cl Chemical compound ClP(C1(C(C=C(C=C1)N(C)C)C(C)(C)C)C(C)(C)C)Cl ATEPEOFRDZUVAG-UHFFFAOYSA-N 0.000 description 2
- 229940126657 Compound 17 Drugs 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 2
- 239000008204 material by function Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004306 triazinyl group Chemical group 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical group CCC1CO1 RBACIKXCRWGCBB-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- 125000004134 1-norbornyl group Chemical group [H]C1([H])C([H])([H])C2(*)C([H])([H])C([H])([H])C1([H])C2([H])[H] 0.000 description 1
- MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
- BWGRDBSNKQABCB-UHFFFAOYSA-N 4,4-difluoro-N-[3-[3-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)-8-azabicyclo[3.2.1]octan-8-yl]-1-thiophen-2-ylpropyl]cyclohexane-1-carboxamide Chemical compound CC(C)C1=NN=C(C)N1C1CC2CCC(C1)N2CCC(NC(=O)C1CCC(F)(F)CC1)C1=CC=CS1 BWGRDBSNKQABCB-UHFFFAOYSA-N 0.000 description 1
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 1
- TXCDCPKCNAJMEE-UHFFFAOYSA-N Dibenzofuran Natural products C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical group COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical group CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical group COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- NUGPIZCTELGDOS-QHCPKHFHSA-N N-[(1S)-3-[4-(3-methyl-5-propan-2-yl-1,2,4-triazol-4-yl)piperidin-1-yl]-1-pyridin-3-ylpropyl]cyclopentanecarboxamide Chemical compound C(C)(C)C1=NN=C(N1C1CCN(CC1)CC[C@@H](C=1C=NC=CC=1)NC(=O)C1CCCC1)C NUGPIZCTELGDOS-QHCPKHFHSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- PBAYDYUZOSNJGU-UHFFFAOYSA-N chelidonic acid Natural products OC(=O)C1=CC(=O)C=C(C(O)=O)O1 PBAYDYUZOSNJGU-UHFFFAOYSA-N 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 239000008358 core component Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005299 dibenzofluorenyl group Chemical group C1(=CC=CC2=C3C(=C4C=5C=CC=CC5CC4=C21)C=CC=C3)* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical group CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
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- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 150000002504 iridium compounds Chemical class 0.000 description 1
- YJLPIKFDEXHCNQ-UHFFFAOYSA-N iridium;quinoline Chemical class [Ir].N1=CC=CC2=CC=CC=C21 YJLPIKFDEXHCNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000005968 oxazolinyl group Chemical group 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Definitions
- the present invention relates to the technical field of organic electroluminescence, in particular to organic luminescence materials, in particular to a metal complex and its application in organic electroluminescence devices.
- OLEDs organic electroluminescent devices
- the basic structure of OLED devices is that various organic functional material films with different functions are mixed between metal electrodes, like a sandwich structure. Driven by current, holes and electrons are injected from the cathode and anode, and holes and electrons are respectively injected. After moving a certain distance, the light-emitting layer is recombined and released in the form of light or heat, thereby producing the luminescence of the OLED.
- organic functional materials are the core components of organic electroluminescent devices, and the thermal stability, photochemical stability, electrochemical stability, quantum yield, film formation stability, crystallinity, color saturation, etc. A major factor in device performance.
- organic functional materials include fluorescent materials and phosphorescent materials.
- the fluorescent material is usually an organic small molecule material, and generally can only use 25% of the singlet state to emit light, so the luminous efficiency is relatively low.
- phosphorescent materials can utilize 75% of the energy of triplet excitons in addition to the 25% singlet state, so the luminous efficiency can be greatly improved.
- phosphorescent materials start late, and the thermal stability, life, and color saturation of the materials need to be improved, which is a challenging topic.
- organometallic compounds have been developed as such phosphorescent materials.
- the invention patent document CN107973823 discloses a class of quinoline iridium compounds, but the color saturation and device performance, especially the luminous efficiency and device life of such compounds need to be improved;
- the invention patent document CN106459114 discloses a class of ⁇ -diketones Ligand-coordinated iridium compounds, but such compounds have high sublimation temperature, poor color saturation, especially, device performance is not ideal, and needs to be further improved;
- invention patent CN109721628 discloses fluorenyl thienopyrimidine structure compounds and Organic electroluminescent devices and compounds containing the compound;
- invention patents CN111377969A and CN111620910A disclose complexes of dibenzofuran biisoquinoline structure and organic electroluminescent devices and compounds containing the complexes.
- the present invention has been made to solve the above-mentioned problems, and an object of the present invention is to provide a high-performance organic electroluminescence device and a novel material capable of realizing such an organic electroluminescence device.
- the present inventors have repeatedly conducted intensive studies to achieve the aforementioned object, and found that a high-performance organic electroluminescence device can be obtained by using a metal complex including a structure represented by the following formula (1) as a ligand.
- One of the objectives of the present invention is to provide a metal complex, which has the advantages of low sublimation temperature, high light and electrochemical stability, high color saturation, high luminous efficiency, long device life, etc. in organic electroluminescent devices.
- a red light-emitting dopant it has the possibility of being applied to the OLED industry.
- a metal complex having the general formula of Ir(La)(Lb)(Lc), and its structural formula is shown in formula (1),
- X is independently selected from O, S, Se;
- R 1 -R 5 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted main chain carbon atoms of 1-10 alkyl, substituted or unsubstituted ring-forming carbon atoms of 3-20 ring Alkyl, substituted or unsubstituted main chain carbon number of 1-10 heteroalkyl, substituted or unsubstituted ring carbon number of 3-20 heterocycloalkyl, substituted or unsubstituted C3- C30 alkylsilyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted
- R 1 -R 5 is F, and one is a substituted or unsubstituted main chain carbon number of 1-10 alkyl, substituted or unsubstituted ring carbon number of 3-20 cycloalkane base, substituted or unsubstituted main chain carbon atoms are 1-10 heteroalkyl, substituted or unsubstituted ring carbon atoms are 3-20 heterocycloalkyl;
- R 6 is a substituted or unsubstituted main chain carbon number of 1-10 alkyl, substituted or unsubstituted ring carbon number of 3-20 cycloalkyl, substituted or unsubstituted main chain carbon atoms
- the number of atoms is 1-10 heteroalkyl, the number of substituted or unsubstituted ring carbon atoms is 3-20 heterocycloalkyl;
- substitution is amino, cyano, nitrile, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted by deuterium, F, Cl, Br, C1-C4 alkyl, Isonitrile, phosphino group substituted;
- heteroatom in the heteroalkyl, heterocycloalkyl or heteroaryl is at least one of S, O, N;
- Lb and Lc are both monoanionic bidentate ligands, and La, Lb and Lc are arbitrarily connected to each other in pairs to form polydentate ligands, or the three are connected through a group;
- At least two of La, Lb, and Lc are the same.
- Lb is the structure shown in formula (2):
- the dotted line position represents the position connected to the metal Ir;
- R a -R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted main chain carbon atoms with 1-10 alkyl, substituted or unsubstituted ring carbon atoms with 3-20 Cycloalkyl, substituted or unsubstituted main chain carbon number of 1-10 heteroalkyl, substituted or unsubstituted ring-forming carbon number of 3-20 heterocycloalkyl or R a , R b , R C is connected in pairs to form an aliphatic ring structure, and Re , R f and R g are connected in pairs to form an aliphatic ring structure; wherein, the substitution is replaced by deuterium, F, Cl, Br, C1- C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted amino, cyano, nitrile, isonitrile, phosphino substituted.
- R a , R b , and R c are the same as Re , R f , and R g , respectively.
- R a , R b , R c , Re , R f , R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-10 carbon atoms in the main chain, substituted or unsubstituted
- the number of ring carbon atoms is 3-20 cycloalkyl or R a , R b , R c are connected in pairs to form an aliphatic ring structure, and R e , R f , R g are connected in pairs to form aliphatic Ring structure; wherein, the substitution is substituted by deuterium, F, Cl, Br, C1-C4 alkyl, C3-C6 cycloalkyl, R d is selected from hydrogen, deuterium, halogen, substituted or unsubstituted
- the number of carbon atoms in the main chain is 1-10 alkyl groups.
- R 6 is a substituted or unsubstituted alkyl group with no more than 4 carbon atoms in the main chain or a substituted or unsubstituted cycloalkyl group with no more than 6 ring carbon atoms.
- the F is not at the position of R 5 .
- one of R 1 -R 5 is F, and the other is a substituted or unsubstituted alkyl group with no more than 4 carbon atoms in the main chain or a substituted or unsubstituted ring-forming carbon Cycloalkyl with no more than 6 atoms, the other three being hydrogen.
- R 1 -R 5 when one of R 1 -R 5 is F, the other is an alkyl group having a branched main chain substituted with a C1-C4 alkyl group having no more than 4 carbon atoms.
- La is independently selected from one of the following structural formulas or their corresponding partially or fully deuterated compounds or their corresponding partially or fully fluorinated compounds:
- Lb is independently selected from one of the following structural formulas or their corresponding partial or complete deuterium or fluoride:
- the ligand La whose structure is shown below,
- R1-R6, X are as defined above.
- Another object of the present invention is to provide an electroluminescent device comprising: a cathode, an anode and an organic layer disposed between the cathode and the anode, at least one layer of the organic layer comprises the metal complex.
- the organic layer is a light-emitting layer
- the metal complex is used as a red light-emitting doping material of the light-emitting layer
- the organic layer is a hole injection layer
- the metal complex is used as a hole injection material in the hole injection layer.
- the material of the invention not only has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like.
- the material of the present invention can convert the triplet excited state into light, so the luminous efficiency of the organic electroluminescence device can be improved, thereby reducing the energy consumption.
- Fig. 1 is the 1HNMR spectrogram of compound La027 of the present invention in deuterated chloroform solution
- Fig. 2 is the 1HNMR spectrum of compound Ir(La027) 2 (Lb005) of the present invention in deuterated chloroform solution,
- Fig. 3 is the ultraviolet absorption spectrum and emission spectrum of the inventive compound Ir(La027) 2 (Lb005) in dichloromethane solution.
- a metal complex having the general formula of Ir(La)(Lb)(Lc), and its structural formula is shown in formula (1),
- X is independently selected from O, S, Se;
- R 1 -R 5 are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted main chain carbon atoms of 1-10 alkyl, substituted or unsubstituted ring-forming carbon atoms of 3-20 ring Alkyl, substituted or unsubstituted main chain carbon number of 1-10 heteroalkyl, substituted or unsubstituted ring carbon number of 3-20 heterocycloalkyl, substituted or unsubstituted C3- C30 alkylsilyl, substituted or unsubstituted C1-C10 alkoxy, substituted or unsubstituted C7-C30 aralkyl, substituted or unsubstituted C6-C30 aryloxy, substituted or unsubstituted C2-C20 alkenyl, substituted or unsubstituted C2-C20 alkynyl, substituted or unsubstituted C6-C30 aryl, substituted or unsubstituted
- R 1 -R 5 is F, and one is a substituted or unsubstituted main chain carbon number of 1-10 alkyl, substituted or unsubstituted ring carbon number of 3-20 cycloalkane base, substituted or unsubstituted main chain carbon atoms are 1-10 heteroalkyl, substituted or unsubstituted ring carbon atoms are 3-20 heterocycloalkyl;
- R 6 is a substituted or unsubstituted main chain carbon number of 1-10 alkyl, substituted or unsubstituted ring carbon number of 3-20 cycloalkyl, substituted or unsubstituted main chain carbon atoms
- the number of atoms is 1-10 heteroalkyl, the number of substituted or unsubstituted ring carbon atoms is 3-20 heterocycloalkyl;
- substitution is amino, cyano, nitrile, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted by deuterium, F, Cl, Br, C1-C4 alkyl, Isonitrile, phosphino group substituted;
- heteroatom in the heteroalkyl or heteroaryl is at least one of S, O, and N;
- Lb and Lc are both monoanionic bidentate ligands, and La, Lb and Lc are arbitrarily connected to each other in pairs to form polydentate ligands, or the three are connected through a group;
- At least two of La, Lb, and Lc are the same.
- Lb is the structure shown in formula (2):
- the dotted line position represents the position connected to the metal Ir;
- R a -R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted main chain carbon atoms with 1-10 alkyl, substituted or unsubstituted ring carbon atoms with 3-20 Cycloalkyl, substituted or unsubstituted main chain carbon number of 1-10 heteroalkyl, substituted or unsubstituted ring-forming carbon number of 3-20 heterocycloalkyl or R a , R b , R C is connected in pairs to form an aliphatic ring structure, and Re , R f and R g are connected in pairs to form an aliphatic ring structure; wherein, the substitution is replaced by deuterium, F, Cl, Br, C1- C4 alkyl, C1-C4 alkoxy, C3-C6 cycloalkyl, C1-C4 alkyl substituted amino, cyano, nitrile, isonitrile, phosphino substituted.
- R a , R b , and R c are the same as Re , R f , and R g , respectively.
- R a -R g are independently selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-10 main chain carbon atoms, substituted or unsubstituted cycloalkane with 3-20 ring carbon atoms
- R a , R b , R c are connected in pairs to form an aliphatic ring structure
- R e , R f , R g are connected in pairs to form an aliphatic ring structure; wherein, the substitution is deuterium , F, Cl, Br, C1-C4 alkyl, C3-C6 cycloalkyl substituted.
- R d is selected from hydrogen, deuterium, halogen, substituted or unsubstituted alkyl with 1-10 carbon atoms in the main chain.
- R 6 is a substituted or unsubstituted alkyl group with no more than 4 carbon atoms in the main chain or a substituted or unsubstituted cycloalkyl group with no more than 6 ring carbon atoms.
- the F is not at the position of R 5 .
- one of R 1 -R 5 is F, and the other is a substituted or unsubstituted alkyl group with no more than 4 carbon atoms in the main chain or a substituted or unsubstituted ring-forming carbon Cycloalkyl with no more than 6 atoms, the other three being hydrogen.
- R 1 -R 5 when one of R 1 -R 5 is F, the other is an alkyl group having a branched main chain substituted with a C1-C4 alkyl group having no more than 4 carbon atoms.
- carbon number a to b in the expression “substituted or unsubstituted X group with carbon numbers a to b" represents the number of carbons in the case where the X group is unsubstituted, The carbon number of the substituent when the X group is substituted is not included.
- the C1-C10 alkyl group is a linear or branched alkyl group, specifically, methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl , tert-butyl, n-pentyl and its isomers, n-hexyl and its isomers, n-heptyl and its isomers, n-octyl and its isomers, n-nonyl and its isomers, n- Decyl and its isomers, etc., preferably methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, more preferably propyl, isopropyl, Isobutyl, sec-butyl, tert-butyl.
- Examples of the C3-C20 cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-adamantyl, 2-adamantyl, 1-norbornyl, and 2-norbornyl Alkyl and the like are preferably cyclopentyl and cyclohexyl.
- Examples of the C2-C10 alkenyl group include vinyl, propenyl, allyl, 1-butadienyl, 2-butadienyl, 1-hexatrienyl, 2-hexatrienyl, 3 -Hexatrienyl and the like, preferably propenyl and allyl.
- the C1-C10 heteroalkyl group is a straight-chain or branched-chain alkyl group, cycloalkyl group, etc. containing atoms other than carbon and hydrogen, and examples thereof include mercaptomethylmethane group, methoxymethane group, ethyl Oxymethane group, tert-butoxymethane group, N,N-dimethylmethane group, epoxy butane group, epoxy pentyl group, epoxy hexane group, etc., preferably methoxy Oxypentyl.
- aryl group examples include a phenyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a naphthacyl group, a pyrenyl group, a drieryl group, a benzo[c]phenanthrenyl group, a benzo[g]drienyl group, a fluorenyl group, Benzofluorenyl, dibenzofluorenyl, biphenyl, terphenyl, tetraphenyl, fluoranthyl, etc., preferably phenyl and naphthyl.
- heteroaryl group examples include a pyrrolyl group, a pyrazinyl group, a pyridyl group, a pyrimidinyl group, a triazinyl group, an indolyl group, an isoindolyl group, an imidazolyl group, a furanyl group, a benzofuranyl group, and an isophenyl group.
- the glass substrate of the anode electrode was ultrasonically cleaned in ethanol for 10 minutes, dried at 150°C, and then treated with N 2 Plasma for 30 minutes.
- the washed glass substrate was installed on the substrate holder of the vacuum evaporation device, and the compounds HTM1 and P-dopant (the ratio of 97%: 3%), the formed film thickness is film, followed by evaporation of a layer of HTM1 to form a film thickness of The left and right films, and then evaporate a layer of HTM2 on the HTM1 film to form a film thickness of Then, on the HTM2 film layer, the host material 1 and the host material 2 and the doping compound (the ratio is: 48.5%: 48.5%: 3%, the comparative compound X, the compound of the present invention are evaporated in the co-evaporation mode ), the film thickness is The ratio of host material and doping material is 90%: 10%, and ETL: LiQ ( The ratio is 50%:50%), and then Y
- the metal iridium complex of the present invention has a larger red shift compared with the comparative compound, which can meet the industrialization requirements for deep red light, especially the BT2020 color gamut.
- the sublimation temperature is defined as the temperature corresponding to the evaporation rate of 1 Angstrom per second at a vacuum degree of 10-7 Torr.
- the test results are as follows:
- the metal iridium complex of the present invention has a lower sublimation temperature, which is beneficial to industrial application.
- the present invention unexpectedly provides better device luminous efficiency and improved lifetime, and provides lower sublimation temperature and more saturated red luminescence through special matching of substituents.
- the above results show that the compound of the present invention has the advantages of low sublimation temperature, high optical and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like, and can be used in organic electroluminescent devices.
- a red light-emitting dopant it has the potential to be used in the OLED industry, especially for displays, lighting and automotive taillights.
- the compound of the invention has the advantages of high light and electrochemical stability, high color saturation, high luminous efficiency, long device life and the like, and can be used in organic electroluminescence devices. Especially as a red light-emitting dopant, it has the possibility of being applied to the OLED industry.
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Abstract
Description
材料 | PL峰值波长/nm |
Ir(La001) 2Lb005 | 627 |
Ir(La002) 2Lb005 | 629 |
Ir(La027) 2Lb005 | 626 |
Ir(La027) 2Lb031 | 627 |
Ir(La028) 2Lb005 | 626 |
Ir(La037) 2Lb005 | 630 |
Ir(La080) 2Lb005 | 627 |
Ir(La106) 2Lb005 | 628 |
Ir(La171) 2Lb005 | 629 |
对比化合物1 | 610 |
对比化合物2 | 637 |
对比化合物3 | 611 |
对比化合物4 | 608 |
对比化合物5 | 616 |
材料 | 升华温度 |
Ir(La001) 2Lb005 | 255 |
Ir(La002) 2Lb005 | 257 |
Ir(La027) 2Lb005 | 260 |
Ir(La027) 2Lb031 | 262 |
Ir(La028) 2Lb005 | 263 |
Ir(La037) 2Lb005 | 259 |
Ir(La080) 2Lb005 | 263 |
Ir(La106) 2Lb005 | 264 |
Ir(La171) 2Lb005 | 265 |
对比化合物1 | 280 |
对比化合物2 | 288 |
对比化合物3 | 286 |
对比化合物4 | 276 |
对比化合物5 | 268 |
Claims (14)
- 一种金属络合物,其具有Ir(La)(Lb)(Lc)的通式,其结构如式(1)所示,其中X独立地选自O,S,Se;其中R 1-R 5独立地选自氢、氘、卤素、取代的或未取代的主链碳原子数为1-10烷基、取代的或未取代的成环碳原子数为3-20环烷基、取代的或未取代的主链碳原子数为1-10杂烷基、取代的或未取代的成环碳原子数为3-20杂环烷基、取代的或未取代的C3-C30烷基硅基、取代的或未取代的C1-C10烷氧基、取代的或未取代的C7-C30芳烷基、取代的或未取代的C6-C30芳氧基、取代或未取代的C2-C20的烯基、取代或未取代的C2-C20的炔基、取代的或未取代的C6-C30芳基、取代的或未取代的C3-C30杂芳基、取代的或未取代的C3-C30芳基硅基、取代或未取代的C0-C20的烷胺基、氰基、腈、异腈、膦基;且其中R 1-R 5中至少一个为F,一个为取代的或未取代的主链碳原子数为1-10烷基、取代的或未取代的成环碳原子数为3-20环烷基、取代的或未取代的主链碳原子数为1-10杂烷基、取代的或未取代的成环碳原子数为3-20杂环烷基;其中R 6为取代的或未取代的主链碳原子数为1-10烷基、取代的或未取代的成环碳原子数为3-20环烷基、取代的或未取代的主链碳原子数为1-10杂烷基、取代的或未取代的成环碳原子数为3-20杂环烷基;其中,所述取代为被氘、F、Cl、Br、C1-C4烷基、C1-C4烷氧基、C3-C6环烷基、C1-C4烷基取代的胺基、氰基、腈、异腈、膦基所取代;其中,所述杂烷基、杂环烷基或杂芳基中的杂原子为S、O、N中的至少一个;其中,Lb和Lc均为单阴离子型双齿配体,La、Lb和Lc三者任意的相互两两连接形成多齿配体,或三者通过一个基团连接;其中,La、Lb、Lc三者之间至少有两个相同。
- 根据权利要求2所述的金属络合物,其中,Lc和La为相同的结构,形成(La) 2Ir(Lb)结构。
- 根据权利要求3所述的金属络合物,其中,R a、R b、R c分别与R e、R f、R g相同。
- 根据权利要求4所述的金属络合物,其中,R a、R b、R c、R e、R f、R g独立地选自氢、氘、卤素、取代的或未取代的主链碳原子数为1-10烷基、取代的或未取代的成环碳原子数为3-20环烷基或者R a、R b、R c之间两两连接以形成脂肪环状结构,R e、R f、R g之间两两连接以形成脂肪环状结构;其中,所述取代为被氘、F、Cl、Br、C1-C4烷基、C3-C6环烷基所取代;R d选自氢、氘、卤素、取代的或未取代的主链碳原子数为1-10烷基。
- 根据权利要求1-6任一所述的金属络合物,其中R 6为取代的或未取代的主链碳原子数不超过4的烷基或取代的或未取代的成环碳原子不超过6的环烷基。
- 根据权利要求7所述的金属络合物,其中,所述F不在R 5的位置;其中X为氧原子O。
- 根据权利要求8所述的金属络合物,其中R 1-R 5中的一个为F,另一个为取代的或未取代的主链碳原子数不超过4的烷基或取代的或未取代的成环碳原子不超过6的环烷基,其它三个均为氢。
- 根据权利要求9所述的金属络合物,当R 1-R 5中一个为F,另一个为具有C1-C4烷基取代的支链化的主链碳原子数不超过4的烷基,其它三个均为氢。
- 一种电致发光器件,其包括:阴极,阳极以及设置在阴极与阳极之间的有机层,所述有机层至少一层包含权利要求1-11任一所述的金属络合物。
- 根据权利要求12所述的电致发光器件,其中所述有机层为发光层,所述权利要求1-11任一所述的金属络合物作为发光层的红色发光掺杂材料;或者其中所述有机层为空穴注入层,所述权利要求1-11任一所述的金属络合物作为空穴注入层中的空穴注入材料。
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