CN108892691A - One kind containing iridium metal complexes and its organic luminescent device - Google Patents
One kind containing iridium metal complexes and its organic luminescent device Download PDFInfo
- Publication number
- CN108892691A CN108892691A CN201810629453.9A CN201810629453A CN108892691A CN 108892691 A CN108892691 A CN 108892691A CN 201810629453 A CN201810629453 A CN 201810629453A CN 108892691 A CN108892691 A CN 108892691A
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- Prior art keywords
- metal complexes
- unsubstituted
- substituted
- compound
- iridium metal
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 title claims abstract description 30
- 239000002184 metal Substances 0.000 title claims abstract description 30
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 239000000463 material Substances 0.000 claims abstract description 19
- 239000002019 doping agent Substances 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 9
- -1 iridium metals Chemical class 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 229910052737 gold Inorganic materials 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 229910052703 rhodium Inorganic materials 0.000 claims description 3
- 229910052707 ruthenium Inorganic materials 0.000 claims description 3
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 claims description 3
- 230000000536 complexating effect Effects 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 37
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 18
- 239000003446 ligand Substances 0.000 abstract description 9
- 230000008901 benefit Effects 0.000 abstract description 6
- 239000000126 substance Substances 0.000 abstract description 6
- 229910001873 dinitrogen Inorganic materials 0.000 abstract description 4
- 150000001768 cations Chemical class 0.000 abstract description 2
- 125000001424 substituent group Chemical group 0.000 abstract description 2
- 239000010410 layer Substances 0.000 description 30
- 239000000047 product Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- 150000004696 coordination complex Chemical class 0.000 description 15
- 238000003756 stirring Methods 0.000 description 11
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- 238000003786 synthesis reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 238000005401 electroluminescence Methods 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000004440 column chromatography Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 5
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Substances ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 3
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- 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
- HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HAEQAUJYNHQVHV-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylbenzamide Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(C(=O)NC2=CC=CC=C2)C=CC=1 HAEQAUJYNHQVHV-UHFFFAOYSA-N 0.000 description 2
- DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 2
- GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- ISMDILRWKSYCOD-GNKBHMEESA-N C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O Chemical compound C(C1=CC=CC=C1)[C@@H]1NC(OCCCCCCCCCCCNC([C@@H](NC(C[C@@H]1O)=O)C(C)C)=O)=O ISMDILRWKSYCOD-GNKBHMEESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 229940126639 Compound 33 Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910006124 SOCl2 Inorganic materials 0.000 description 2
- REAYFGLASQTHKB-UHFFFAOYSA-N [2-[3-(1H-pyrazol-4-yl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound N1N=CC(=C1)C=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 REAYFGLASQTHKB-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- 229940125758 compound 15 Drugs 0.000 description 2
- JNGZXGGOCLZBFB-IVCQMTBJSA-N compound E Chemical compound N([C@@H](C)C(=O)N[C@@H]1C(N(C)C2=CC=CC=C2C(C=2C=CC=CC=2)=N1)=O)C(=O)CC1=CC(F)=CC(F)=C1 JNGZXGGOCLZBFB-IVCQMTBJSA-N 0.000 description 2
- 238000013461 design Methods 0.000 description 2
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
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- 125000005842 heteroatom Chemical group 0.000 description 2
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
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- 230000004048 modification Effects 0.000 description 2
- SJYNFBVQFBRSIB-UHFFFAOYSA-N norbornadiene Chemical compound C1=CC2C=CC1C2 SJYNFBVQFBRSIB-UHFFFAOYSA-N 0.000 description 2
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 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
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 1
- VFMUXPQZKOKPOF-UHFFFAOYSA-N 2,3,7,8,12,13,17,18-octaethyl-21,23-dihydroporphyrin platinum Chemical compound [Pt].CCc1c(CC)c2cc3[nH]c(cc4nc(cc5[nH]c(cc1n2)c(CC)c5CC)c(CC)c4CC)c(CC)c3CC VFMUXPQZKOKPOF-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- MZSAMHOCTRNOIZ-UHFFFAOYSA-N 3-[4-(aminomethyl)-6-(trifluoromethyl)pyridin-2-yl]oxy-N-phenylaniline Chemical compound NCC1=CC(=NC(=C1)C(F)(F)F)OC=1C=C(NC2=CC=CC=C2)C=CC=1 MZSAMHOCTRNOIZ-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 239000012327 Ruthenium complex Substances 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- ZEEBGORNQSEQBE-UHFFFAOYSA-N [2-(3-phenylphenoxy)-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound C1(=CC(=CC=C1)OC1=NC(=CC(=C1)CN)C(F)(F)F)C1=CC=CC=C1 ZEEBGORNQSEQBE-UHFFFAOYSA-N 0.000 description 1
- LXGQHDUCNDGTDB-PAMNCVQHSA-N [2-[(8s,9r,10s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;[2-[(8s,9r,10s,13s,14s,16s,17r)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11, Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COC(C)=O)(O)[C@@]1(C)CC2O.C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)COP(O)(O)=O)(O)[C@@]1(C)CC2O LXGQHDUCNDGTDB-PAMNCVQHSA-N 0.000 description 1
- SAHIZENKTPRYSN-UHFFFAOYSA-N [2-[3-(phenoxymethyl)phenoxy]-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound O(C1=CC=CC=C1)CC=1C=C(OC2=NC(=CC(=C2)CN)C(F)(F)F)C=CC=1 SAHIZENKTPRYSN-UHFFFAOYSA-N 0.000 description 1
- ABRVLXLNVJHDRQ-UHFFFAOYSA-N [2-pyridin-3-yl-6-(trifluoromethyl)pyridin-4-yl]methanamine Chemical compound FC(C1=CC(=CC(=N1)C=1C=NC=CC=1)CN)(F)F ABRVLXLNVJHDRQ-UHFFFAOYSA-N 0.000 description 1
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- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 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 1
- 230000007423 decrease Effects 0.000 description 1
- FFHWGQQFANVOHV-UHFFFAOYSA-N dimethyldioxirane Chemical compound CC1(C)OO1 FFHWGQQFANVOHV-UHFFFAOYSA-N 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 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
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
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- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000002356 single layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- PANBYUAFMMOFOV-UHFFFAOYSA-N sodium;sulfuric acid Chemical compound [Na].OS(O)(=O)=O PANBYUAFMMOFOV-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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Abstract
The present invention provides a kind of containing iridium metal complexes and its organic luminescent device, this contains iridium metal complexes with structure shown in formula (I), structure includes the first ligand and assistant ligand, wherein the dinitrogen coordination structure of the electron rich in assistant ligand structure is conducive to stablize center trivalent metal cation, simultaneously, also it will affect the Cloud Distribution on metal iridium, and then the photoelectric property of entire complex molecule is had a huge impact, and the four-membered ring that the ligand of dinitrogen coordination structure and metal are constituted has stronger rigidity, advantageously reduce unnecessary vibrational energy loss, realize efficient luminescent properties.By adjusting substituent group group, make complex compound that there is better thermal stability and chemical property.Iridium metal complexes are prepared into device, especially as dopant material, device shows the advantage that driving voltage is low, luminous efficiency is high, is better than existing common OLED device.
Description
Technical field
The present invention relates to organic photoelectrical material technical fields, and in particular to one kind contains iridium metal complexes and its organic light emission
Device.
Background technique
Organic compound is deposited the mode of Deng Qingyun of Kodak in 1987 et al. first passage vacuum evaporation
At unformed organic film, and different organic materials is selected to be prepared for double-deck OLED device as hole and electron transfer layer
Part, for device when voltage is 10V or so, device light emission luminance has reached 1000cd m-2, maximum external quantum efficiency EQE
(External Quantum Efficiency) is 1% or so, shows extraordinary electroluminescent properties, this is indicated
A possibility that organic electroluminescence device (OLED) has had been provided with practical application, from there on, each major company and scientific research machine
Structure has all put into a large amount of manpower and resource carries out the research in organic electroluminescent direction.Nineteen ninety univ cambridge uk
Friend et al. is prepared in such a way that solution is processed based on high molecular material poly (p-phenylene vinylene)
(PPV) single layer OLED devices, so that high molecular material is also gradually applied to field of organic electroluminescence.The general woods in the U.S. in 1998
The Forrest et al. of Si Dun university reports the doping phosphorescent devices with octaethylporphyrin platinum (PtOEP) for object.Be different from
Into fluorescent material, internal quantum efficiency is only 25% this limitation, and phosphor material realizes 100% internal quantum efficiency, phosphorescence electricity
An important breakthrough for being the discovery that electroluminescent organic material development for electroluminescent material.
In the latest 20 years, application of the phosphorescent light-emitting materials in organic electroluminescent receives academia and widely pays close attention to,
Relevant phosphorescent compound is contained with planar structure, the Pt (II) of d8 electron configuration, Pd (II), Au (III) complex compound, with
And with complex compounds such as octahedral structure, the Ru (II) of d6 electron configuration, Rh (III), Re (I), Ir (III), Os (II).Wherein
Study it is more be osmium, iridium, platinum and ruthenium complex compound, they have preferable luminous efficiency, and there is shorter phosphorescence partly to decline
Phase, to greatly reduce the probability that non-radiative mode fails.Iridium complex is due to having shorter phosphorescent lifetime, higher phosphorescence
Quantum yield, preferable thermal stability, regular octahedron coordination structure be also not easy to form more serious pi-pi accumulation etc. it is excellent
Property becomes an important research direction for designing new and effective feux rouges to near-infrared phosphor material.
Green light, the efficiency of yellow light organic phosphorescent material and service life can reach the requirement of industrialization substantially, but high property
The feux rouges phosphor material of energy still needs further to be developed.Metal iridium complex is due to, luminous efficiency shorter with phosphorescent lifetime
The advantages that high, simple, the photochromic easy adjusting of synthesis purification, good calorifics and electrochemical stability, it is new and effective to become design
One research hotspot of feux rouges phosphor material.
Currently, organic luminescent device is towards practical, commercialized development, but still Shortcomings, phosphor material are general
Store-through is thermal stability is poor, luminous efficiency is low, service life short problem, and determines the basic of organic electroluminescence device performance superiority and inferiority
Factor is the selection of material, it would therefore be highly desirable to design and develop a kind of organic metal low with higher luminous efficiency, driving voltage
Complex compound.
Summary of the invention
It is provided by the invention to contain iridium metals the object of the present invention is to provide a kind of metal complex and its organic luminescent device
Complex compound has the advantages that driving voltage is low, luminous efficiency is high, is the luminous organic material of function admirable.
Present invention firstly provides a kind of metal complex, structural formula (I) is：
Wherein M is selected from one of Ir, Rh, Re, Ru, Os, Pt, Au, Cu；
Wherein X is selected from CH or N；
Wherein R, R3Independently selected from substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C60 virtue
One of base, substituted or unsubstituted C3~C60 heteroaryl；
Wherein R1、R2It is independently selected from CF3, substituted or unsubstituted C1~C30 alkyl, C1~C30 alkoxy, replace or not
One of substituted C6~C60 aryl, substituted or unsubstituted C3~C60 heteroaryl.
Preferably, wherein R, R3Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~
One of C30 aryl, substituted or unsubstituted C3~C30 heteroaryl；
Wherein R1、R2Independently selected from CF3, substituted or unsubstituted C1~C10 alkyl, C1~C10 alkoxy, replace or
One of unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 heteroaryl.
Preferably, the metal complex, wherein M is selected from Ir.
Preferably, the metal complex, it is uncharged.
Preferably, the metal complex, R1、R2Same or different is selected from flowering structure：
Preferably, the metal complex, any one in structure as follows：
The present invention also provides a kind of above-mentioned applications containing iridium metal complexes in an organic light emitting device.
Preferably, the organic luminescent device includes that anode, cathode and several between anode and cathode have
Machine functional layer, the organic function layer contain described one kind containing iridium metal complexes.
Preferably, a kind of organic luminescent device, the organic function layer include hole injection layer, hole transport
Layer, electronic barrier layer, luminescent layer, hole blocking layer, electron transfer layer, at least one layer in electron injecting layer；Organic function
It is at least one layer of in ergosphere to contain iridium metal complexes containing described one kind.
Preferably, a kind of organic luminescent device contains iridium containing described one kind in luminescent layer object dopant material
Metal complex.
Beneficial effects of the present invention:
Present invention firstly provides a kind of complex compound, which has a structure shown in formula (I), structure include the first ligand and
Assistant ligand, wherein the first ligand reduces the collision between triplet excitons by the big pi-conjugated structure of introducing and steric group, gram
Device the problem of roll-offing of efficiency under high current density is taken, the dinitrogen coordination structure of the electron rich in assistant ligand structure is advantageous
In stablizing center trivalent metal cation, meanwhile, it also will affect the Cloud Distribution on metal iridium, and then for entire complex compound
The photoelectric property of molecule has a huge impact, and the four-membered ring that the ligand of dinitrogen coordination structure is constituted with metal is with stronger
Rigidity, advantageously reduce the loss of unnecessary vibrational energy, realize efficient luminescent properties.By adjusting substituent group group,
Make complex compound that there is better thermal stability and chemical property.Iridium complex is prepared into device, especially as dopant material,
Device shows the advantage that driving voltage is low, luminous efficiency is high, is better than existing common OLED device.
Specific embodiment
For a further understanding of the present invention, the preferred embodiment of the invention is described below with reference to embodiment, still
It should be appreciated that these descriptions are only further explanation the features and advantages of the present invention, rather than to the claims in the present invention
Limitation.
Alkyl of the present invention refers to alkyl made of minusing a hydrogen atom in alkane molecule, can be straight chain alkane
Base, branched alkyl, naphthenic base, example may include methyl, ethyl, propyl, 1- Methylethyl, isopropyl, 1- methyl-propyl, positive fourth
Base, isobutyl group, sec-butyl, tert-butyl, 1- methyl butyl, 2- methyl butyl, 3- methyl butyl, amyl, isopentyl, cyclopenta,
Cyclohexyl etc., but not limited to this.
Alkoxy of the present invention refers to the total of the group for referring to that a hydrogen atom is substituted by oxygen atom in alkane molecule
Claim, example may include-OCH3、—O(CH3)2Deng, but not limited to this.
Aryl of the present invention refers to remove a hydrogen atom on the aromatic core carbon of phenyl molecule after, be left the total of univalent perssad
Claim, example may include phenyl, 4- aminomethyl phenyl, 4- tert-butyl-phenyl, 2- ethylphenyl, xenyl or terphenyl etc., but not
It is limited to this.
Heteroaryl of the present invention refers to the base that one or more aromatic core carbon in phenyl molecule are substituted by hetero atom
The general name of group, the hetero atom include but is not limited to oxygen, sulphur or nitrogen-atoms, example may include pyridyl group, pyrrole radicals, thienyl,
Furyl, oxazolyl or triazine radical etc., but not limited to this.
Present invention firstly provides one kind to contain iridium metal complexes, and structural formula (I) is：
Wherein M is selected from one of Ir, Rh, Re, Ru, Os, Pt, Au, Cu；
Wherein X is selected from CH or N；
Wherein R, R3Independently selected from substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C60 virtue
One of base, substituted or unsubstituted C3~C60 heteroaryl；
Wherein R1、R2Independently selected from CF3, substituted or unsubstituted C1~C30 alkyl, C1~C30 alkoxy, replace or
One of unsubstituted C6~C60 aryl, substituted or unsubstituted C3~C60 heteroaryl.
Preferably, wherein R, R3Independently selected from substituted or unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~
One of C30 aryl, substituted or unsubstituted C3~C30 heteroaryl；
Wherein R1、R2Independently selected from CF3, substituted or unsubstituted C1~C10 alkyl, C1~C10 alkoxy, replace or
One of unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 heteroaryl.
Preferably, the metal complex, wherein M is selected from Ir.
Preferably, the metal complex, it is uncharged.
Preferably, the metal complex, R1、R2Same or different is selected from flowering structure：
Preferably, the metal complex, any one in structure as follows：
It is enumerated above some specific structure types of the present invention containing iridium metal complexes, but the present invention not office
It is limited to these listed chemical structures, all based on structure shown in formula (I), R1-R5All should for group as defined above
It is included.
Metal complex of the present invention, preparation method are as follows：
The preparation of intermediate A
Compound A and SOCl2It is mixed in three-neck flask, flows back, cooling, vacuum distillation removes SOCl2, add diethylamine
Processing is stirred, and washing is dried to obtain compound B.Compound B and the reflux of dioxane and wet chemical are cooled down, acutely stirred
It mixes, it is cooling, it dilutes, washing is dried to obtain compound D.Compound D is mixed with tetrahydrofuran, and stirring is added LDA, reacted
Night, methylene chloride extraction, column chromatography for separation obtain compound E.Compound E reacts to obtain compound F by DMDO.Compound F
It with anhydrous hydrazine and anhydrous methanol, stirs, washing obtains solid powder G.Compound G mixes reflux with norbornadiene, heating,
It is cooling, it dilutes, washs, dry, chromatographic isolation obtains compound H.Compound H is dissolved in 3:1 cellosolvo/water
In (40ml), it is bubbled 15min with nitrogen, then adds chloride hydrate iridium.It is bubbled 15min with nitrogen again, is then stirred under reflux
It mixes mixture to stay overnight, compound is cooled to room temperature, with methanol dilution, and filters, subsequent solid is washed with methanol, obtains intermediate
A。
The preparation of compound L
The hexane solution (100mL) of compound g is added in 100mL four-hole boiling flask, is cooled to -80 DEG C, nitrogen atmosphere
Under be added dropwise compound i, after stirring 1.5 hours, intermediate A is added dropwise into mixed liquor, after being added dropwise, it is small to continue stirring 2
When, yellow solution is obtained, this solution is added dropwise in tetrahydrofuran (100mL) solution of intermediate A, after being added dropwise, is risen
Temperature stirs 12 hours to 60 DEG C, and reaction solution is cooled to room temperature, and has a solid appearance, filter and with washed with ether filter cake three times, then
It is dissolved with methylene chloride, evaporating column chromatography obtains compound L.
The present invention limitation not special to above-mentioned reaction be using popular response well-known to those skilled in the art
It can.
The present invention also provides a kind of organic electroluminescence device, the organic electroluminescence device is those skilled in the art
Known organic electroluminescence device, organic electroluminescence device of the present invention include anode, cathode and are located at
Several organic function layers between the anode and cathode include that the metal complex is any in the organic function layer
It is a kind of or at least two combination.The organic function layer may include hole injection layer, hole transmission layer, electronic barrier layer,
At least one layer in luminescent layer, hole blocking layer, electron transfer layer and electron injecting layer, the preferably described organic function layer include hair
Photosphere, the luminescent layer include the metal complex any one or at least two combination.It is more preferably described to contain iridium metals
Complex compound is used as guest materials in luminescent layer.
The present invention is not particularly limited the source of raw material employed in following embodiment, can for commercial product or
It is prepared using preparation method well-known to those skilled in the art.
Embodiment 1：The preparation of compound 1
The preparation of intermediate A
By the SOCl of compound 1-1 27.4g and 100ml2It is added in three-neck flask, mixture is flowed back 2 hours, and
Red-orange solution is cooled to environment temperature.Excess SOCl is removed by vacuum distillation2, then rinsed 3 times with dry toluene,
Obtained solid acyl chlorides is suspended in 300ml anhydrous methylene chloride, it is cooling through ice-water bath, and add at the diethylamine of 40ml
Solution, is then stirred at room temperature overnight by reason, and sodium bicarbonate and aqueous ammonium chloride solution washing is added, and organic phase is dry with sodium sulphate
It is dry, and be evaporated in vacuo, obtain yellow solid 1-2 29.2g, yield 84%.
Under nitrogen protection, by compound 1-2 8.5g and 2,6- dimethylphenylboronic acid 5.3g, 100ml dioxane and
The 2M wet chemical of 50ml, which is fitted into 250ml round-bottomed flask, to flow back, and stirs 10min, adds the Pd (PPh of 1.4g3)4, 90
Degree Celsius when react 20 hours, then cool down, diluted with 200ml ethyl acetate, organic phase is washed with water, then washed with salt
It washs, then dry with sodium sulphate, column chromatography for separation obtains compound 1-3 3.6g, yield 38%.
The anhydrous tetrahydro furan of 1-3 2.2g and 100ml is put into dry Schlenk bottle, by the sub- nitrogen atmosphere of solution
Lower stirring is cooled to -78 degrees Celsius.LDA solution 5ml is added dropwise, reactant is made to be warming up to ambient temperature overnight.Addition saturation chlorination
Aqueous ammonium reduces volume under reduced pressure, and add methylene chloride extraction, and organic phase is washed with water, then is washed with brine, and uses sulfuric acid
Sodium is dry, and column chromatography for separation obtains compound 1-41.29g, yield 79%.
By the saturated sodium bicarbonate aqueous solution of compound 1-4 1.29g and 100ml methylene chloride, 200ml acetone and 300ml
It is added in beaker.It is vigorously stirred mixture, and adds the KHSO of 10g5.0.5KHSO4.K2HSO4, excessive blistering is avoided, 1 is small
When after, be washed with brine organic phase, obtain yellow solid 1-5 835mg, yield 61%.
Under nitrogen protection, 250ml Schlenk bottle, addition 240 is added in compound 1-5 756mg and 200ml anhydrous methanol
Microlitre anhydrous hydrazine is into 15ml anhydrous methanol.It stirs 16 hours at room temperature, precipitating is collected by filtration, with 20ml ethanol washing, obtains
Compound 1-6 516mg, yield 62% (not separating can use).
Under nitrogen protection, the triethylene glycol condensation by mixing of compound 1-6 and 2ml norbornadiene, 25ml are flowed back, heating
To 170 degrees Celsius, 16 hours, reactant is cooled to room temperature, methylene chloride dilution is washed with water, and sodium sulphate is dry, column chromatography
Separation, evaporative crystallization obtain compound 1-7 150mg, and 49%.
Compound 1-7 150mg is dissolved in 3:In 1 cellosolvo/water (40ml), it is bubbled 15min with nitrogen, is connect
Addition chloride hydrate iridium (80mg, 0.25mmol).It is bubbled 15min with nitrogen again, then stirring mixture is stayed overnight under reflux,
Compound is cooled to room temperature, with methanol dilution, and filters, subsequent solid is washed with methanol, obtains intermediate A 880mg, yield
98%.
The preparation of compound 1
The hexane solution (100mL) of bromobenzene (3.1g, 20mmol) is added in 100mL four-hole boiling flask, is cooled to -80
DEG C, be added dropwise under nitrogen atmosphere n-BuLi (20mmol), stirring 1.5 hours after, into mixed liquor be added dropwise 1-9 (2.5g,
20mmol), after being added dropwise, continue stirring 2 hours, obtain yellow solution, this solution is added dropwise to intermediate A (tetrahydro
In furans (100mL) solution, after being added dropwise, 60 DEG C are warming up to, is stirred 12 hours, reaction solution is cooled to room temperature, and has solid to go out
It is existing, filter and with washed with ether filter cake three times, then dissolved with methylene chloride, column chromatography is concentrated, obtain compound 1 (393mg,
75%).
Mass spectrum m/z：855.06 (calculated values：855.07).Theoretical elemental content (%) C45H38IrN6：C,63.21；H,
4.48；Ir,22.48；N, 9.84 actual measurements constituent content (%)：C,63.22；H,4.47；Ir,22.47；N,9.83.The above results
Confirm that obtaining product is target product.
Embodiment 2：The preparation of compound 15
Change the 1-3 in embodiment 1 into equimolar 15-3, other steps are identical as the synthesis of embodiment 1, obtain mesh
Mark product Compound 15.
Mass spectrum m/z：993.03 (calculated values：993.04).Theoretical elemental content (%) C45H34F6IrN8：C,54.43；H,
3.45；F,11.48；Ir,19.36；N, 11.28 actual measurements constituent content (%)：C,54.42；H,3.46；F,11.47；Ir,
19.35；N,11.27.The above results confirm that obtaining product is target product.
Embodiment 3：The preparation of compound 33
Change the 1-3 in embodiment 1 into equimolar 33-3,1-8 changes equimolar 33-8 into, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 33.
Mass spectrum m/z：1105.44 (calculated value：1105.46).Theoretical elemental content (%) C64H60IrN6：C,69.54；H,
5.47；Ir,17.39；N, 7.60 actual measurements constituent content (%)：C,69.53；H,5.46；Ir,17.38；N,7.61.The above results
Confirm that obtaining product is target product.
Embodiment 4：The preparation of compound 40
Change the 1-3 in embodiment 1 into equimolar 40-3,1-8 changes equimolar 40-8 into, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 40.
Mass spectrum m/z：931.11 (calculated values：931.12).Theoretical elemental content (%) C46H42IrN8O2：C,59.34；H,
4.55；Ir,20.64；N,12.03；O, 3.44 actual measurements constituent content (%)：C,59.35；H,4.56；Ir,20.63；N,12.04；
O,3.45.The above results confirm that obtaining product is target product.
Embodiment 5：The preparation of compound 68
Change the 1-3 in embodiment 1 into equimolar 68-3,1-8 changes equimolar 68-8 into, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 68.
Mass spectrum m/z：973.19 (calculated values：973.18).Theoretical elemental content (%) C49H48IrN8O2：C,60.47；H,
4.97；Ir,19.76；N,11.51；O, 3.29 actual measurements constituent content (%)：C,60.48；H,4.96；Ir,19.75；N,11.52；
O,3.28.The above results confirm that obtaining product is target product.
Embodiment 6：The preparation of compound 83
Change the 1-3 in embodiment 1 into equimolar 83-3,1-8 changes equimolar 83-8 into, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 83.
Mass spectrum m/z：1001.29 (calculated value：1001.28).Theoretical elemental content (%) C56H52IrN6：C,67.17；H,
5.23；Ir,19.20；N, 8.38 actual measurements constituent content (%)：C,67.16；H,5.24；Ir,19.21；N,8.39.The above results
Confirm that obtaining product is target product.
Embodiment 7：The preparation of compound 96
Change the 1-3 in embodiment 1 into equimolar 96-3,1-8 changes equimolar 96-8 into, other steps with implementation
The synthesis of example 1 is identical, obtains target product compound 96.
Mass spectrum m/z：1087.43 (calculated value：1087.44).Theoretical elemental content (%) C60H62IrN8：C,66.27；H,
5.75；Ir,17.68；N, 10.30 actual measurements constituent content (%)：C,66.28；H,5.74；Ir,17.67；N,10.31.Above-mentioned knot
Fruit confirms that obtaining product is target product.
Embodiment 8：The preparation of compound 100
Change the 1-3 in embodiment 1 into equimolar 100-3,1-8 changes equimolar 100-8 into, and 1-9 changes equimolar into
100-9, other steps are identical as the synthesis of embodiment 1, obtain target product compound 100.
Mass spectrum m/z：961.22 (calculated values：961.23).Theoretical elemental content (%) C50H52IrN6O2：C,62.48；H,
5.45；Ir,20.00；N,8.74；O, 3.33 actual measurements constituent content (%)：C,62.47；H,5.46；Ir,20.01；N,8.75；O,
3.32.The above results confirm that obtaining product is target product.
Embodiment 9：The preparation of compound 110
Change the 1-1 in embodiment 1 into equimolar 110-1,1-3 changes equimolar 110-3 into, and 1-8 changes equimolar into
110-8,1-9 changes equimolar 110-9 into, other steps are identical as the synthesis of embodiment 1, obtain target product compound
110。
Mass spectrum m/z：879.13 (calculated values：879.14).Theoretical elemental content (%) C44H46IrN8：C,60.11；H,
5.27；Ir,21.86；N, 12.75 actual measurements constituent content (%)：C,60.12；H,5.28；Ir,21.87；N,12.74.Above-mentioned knot
Fruit confirms that obtaining product is target product.
Embodiment 10：The preparation of compound 120
Change the 1-3 in embodiment 1 into equimolar 120-1,1-3 changes equimolar 120-3 into, and 1-8 changes equimolar into
120-8,1-9 changes equimolar 120-9 into, other steps are identical as the synthesis of embodiment 1,
Obtain target product compound 120.
Mass spectrum m/z：1059.38 (calculated value：1059.39).Theoretical elemental content (%) C58H58IrN8：C,65.76；H,
5.52；Ir,18.14；N, 10.58 actual measurements constituent content (%)：C,65.75；H,5.53；Ir,18.13；N,10.57.Above-mentioned knot
Fruit confirms that obtaining product is target product.
Compare Application Example 1
Ito glass substrate is placed in distilled water and is cleaned 2 times, it is ultrasonic washing 15 minutes, different after distilled water cleans
Ultrasonic washing is later dry in order for propyl alcohol, acetone, methanol equal solvent, is transferred in plasma washing machine, by above-mentioned base
Plate washs 5 minutes, is sent in evaporator.
Hole injection layer 2-TNATA/50nm is successively deposited on the ito transparent electrode having had been prepared for, vapor deposition hole passes
(main body CBP is adulterated Ir (piq) for defeated layer NPB/30nm, vapor deposition2(acac) 10% mixing)/30nm, then vapor deposition electron transfer layer
TPBi/30nm, cathode LiF/0.5nm, Al/200nm.
[Application Example 1-10]
The Ir (piq) in Application Example 1 will be compared2(acac) change into shown compound 1 in embodiment 1-10,15,
33、40、68、83、96、100、110、120。
Table 1 is the compound of preparation of the embodiment of the present invention and the characteristics of luminescence test for comparing luminescent device prepared by substance
As a result.
The characteristics of luminescence of [table 1] luminescent device is tested
The above result shows that a kind of metal complex of the invention is applied in organic luminescent device, especially as hair
Photosphere guest materials shows the low advantage of high-luminous-efficiency, driving voltage, is luminous organic material of good performance.
Obviously, the above description of the embodiment is only used to help understand the method for the present invention and its core ideas.It should refer to
It out, without departing from the principle of the present invention, can also be to this hair for the those of ordinary skill of the technical field
Bright some improvement and modification can also be carried out, and these improvements and modifications also fall within the scope of protection of the claims of the present invention.
Claims (8)
1. one kind contains iridium metal complexes, which is characterized in that shown in structural formula such as formula (I)：
Wherein M is selected from one of Ir, Rh, Re, Ru, Os, Pt, Au, Cu；
Wherein X is selected from CH or N；
Wherein R, R3Independently selected from substituted or unsubstituted C1~C30 alkyl, substituted or unsubstituted C6~C60 aryl, replace
Or one of unsubstituted C3~C60 heteroaryl；
Wherein R1、R2It is independent to be selected from CF3, substituted or unsubstituted C1~C30 alkyl, C1~C30 alkoxy, replace or do not take
One of C6~C60 aryl in generation, substituted or unsubstituted C3~C60 heteroaryl.
2. according to claim 1 a kind of containing iridium metal complexes, which is characterized in that wherein R, R3Independently selected from substitution
Or in unsubstituted C1~C10 alkyl, substituted or unsubstituted C6~C30 aryl, substituted or unsubstituted C3~C30 heteroaryl
One kind；
Wherein R1、R2It is independent to be selected from CF3, substituted or unsubstituted C1~C10 alkyl, C1~C10 alkoxy, replace or do not take
One of C6~C30 aryl in generation, substituted or unsubstituted C3~C30 heteroaryl.
3. according to claim 1 a kind of containing iridium metal complexes, which is characterized in that M is selected from Ir.
4. according to claim 1 a kind of containing iridium metal complexes, which is characterized in that it is uncharged.
5. according to claim 1 a kind of containing iridium metal complexes, which is characterized in that R1、R2Same or different is selected from
With flowering structure：
6. according to claim 1 a kind of containing iridium metal complexes, which is characterized in that described to be selected from containing iridium metal complexes
Any one in structure as follows：
7. a kind of organic luminescent device, including anode, cathode and several organic function layers between anode and cathode,
It is characterized in that, at least described in any item a kind of containing iridium metals complexing containing claim 1~6 in the organic function layer
Object.
8. a kind of organic luminescent device according to claim 7, which is characterized in that claim 1~6 is described in any item
One kind being used as luminescent layer object dopant material containing iridium metal complexes in an organic light emitting device.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI762029B (en) * | 2020-11-12 | 2022-04-21 | 國立清華大學 | Platinum complex, nitrogen-containing didentate ligand and apparatus for providing visible emission or near-infrared emission |
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2018
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI762029B (en) * | 2020-11-12 | 2022-04-21 | 國立清華大學 | Platinum complex, nitrogen-containing didentate ligand and apparatus for providing visible emission or near-infrared emission |
| US11414447B2 (en) | 2020-11-12 | 2022-08-16 | National Tsing Hua University | Platinum complex, nitrogen-containing bidentate chelate, and apparatus for providing visible emission or near-infrared emission |
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