CN106317123A - Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof - Google Patents
Multi-substituted phenylpyridine iridium (III) complex and preparation method and application thereof Download PDFInfo
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- CN106317123A CN106317123A CN201610678047.2A CN201610678047A CN106317123A CN 106317123 A CN106317123 A CN 106317123A CN 201610678047 A CN201610678047 A CN 201610678047A CN 106317123 A CN106317123 A CN 106317123A
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- iii
- iridium
- pyridines
- coordination compound
- substituted benzenes
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- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- ZKYQRJXGGLVQML-UHFFFAOYSA-N iridium(3+);2-phenylpyridine Chemical class [Ir+3].C1=CC=CC=C1C1=CC=CC=N1 ZKYQRJXGGLVQML-UHFFFAOYSA-N 0.000 title abstract 4
- 238000010668 complexation reaction Methods 0.000 title 1
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000000463 material Substances 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000011737 fluorine Substances 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 13
- 239000000539 dimer Substances 0.000 claims abstract description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 9
- SIOXPEMLGUPBBT-UHFFFAOYSA-N Picolinic acid Natural products OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims abstract description 4
- VXKWYPOMXBVZSJ-UHFFFAOYSA-N tetramethyltin Chemical compound C[Sn](C)(C)C VXKWYPOMXBVZSJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 46
- 150000001555 benzenes Chemical class 0.000 claims description 34
- 150000003222 pyridines Chemical class 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 238000005401 electroluminescence Methods 0.000 claims description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 10
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002019 doping agent Substances 0.000 claims description 6
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000036571 hydration Effects 0.000 claims description 3
- 238000006703 hydration reaction Methods 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 239000012046 mixed solvent Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- GJWFUDMQGSFIHE-UHFFFAOYSA-N 2-[1-(trifluoromethyl)triazol-4-yl]pyridine Chemical compound N1=NN(C(F)(F)F)C=C1C1=CC=CC=N1 GJWFUDMQGSFIHE-UHFFFAOYSA-N 0.000 abstract 1
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 abstract 1
- 230000009977 dual effect Effects 0.000 abstract 1
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 abstract 1
- 150000005359 phenylpyridines Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 33
- 229910052757 nitrogen Inorganic materials 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000007787 solid Substances 0.000 description 9
- 238000003786 synthesis reaction Methods 0.000 description 9
- 230000005540 biological transmission Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- TVSJHBPBNBAEGV-UHFFFAOYSA-N 2-[4-fluoro-3-(trifluoromethyl)phenyl]pyridine Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1C1=CC=CC=N1 TVSJHBPBNBAEGV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- -1 polysubstituted phenyl pyrazoline Pyridine iridium (III) Polymers 0.000 description 6
- 208000035126 Facies Diseases 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- GEQBRULPNIVQPP-UHFFFAOYSA-N 2-[3,5-bis(1-phenylbenzimidazol-2-yl)phenyl]-1-phenylbenzimidazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2N=C1C1=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=CC(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=C1 GEQBRULPNIVQPP-UHFFFAOYSA-N 0.000 description 2
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- FFNVQNRYTPFDDP-UHFFFAOYSA-N 2-cyanopyridine Chemical compound N#CC1=CC=CC=N1 FFNVQNRYTPFDDP-UHFFFAOYSA-N 0.000 description 2
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 description 2
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- STSCVKRWJPWALQ-UHFFFAOYSA-N TRIFLUOROACETIC ACID ETHYL ESTER Chemical compound CCOC(=O)C(F)(F)F STSCVKRWJPWALQ-UHFFFAOYSA-N 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- FDTUVFSBEYKVAP-UHFFFAOYSA-N formic acid;pyridine Chemical compound OC=O.C1=CC=NC=C1 FDTUVFSBEYKVAP-UHFFFAOYSA-N 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229920002521 macromolecule Polymers 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229920002098 polyfluorene Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 1,1'-biphenyl;9h-carbazole Chemical group C1=CC=CC=C1C1=CC=CC=C1.C1=CC=C2C3=CC=CC=C3NC2=C1 ZSYMVHGRKPBJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000007445 Chromatographic isolation Methods 0.000 description 1
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 241001597008 Nomeidae Species 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000001808 coupling effect Effects 0.000 description 1
- 238000002242 deionisation method Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000004773 frontier orbital Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- YAHRDLICUYEDAU-UHFFFAOYSA-N methylhexaneamine Chemical compound CCC(C)CC(C)N YAHRDLICUYEDAU-UHFFFAOYSA-N 0.000 description 1
- 239000002052 molecular layer Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- JVNIAJRGELYGEG-UHFFFAOYSA-N pyridine;2h-triazole Chemical compound C1=CNN=N1.C1=CC=NC=C1 JVNIAJRGELYGEG-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000027756 respiratory electron transport chain Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
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
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- 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
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The invention provides a multi-substituted phenylpyridine iridium (III) complex and a preparation method and application thereof. The structural formula of the complex is as shown in the formula I or II. Please see the formula in the description. R1, R2, R3, R4 and R5 are independently hydrogen, fluorine, methyl or trifluoromethyl. The preparation method includes the steps that multi-substituted phenylpyridine reacts with iridium chloride trihydrate to obtain iridium (III) chloro-bridged dimer; then the iridium (III) chloro-bridged dimmer reacts with 2-pyridinecarboxylic acid or 3-trifluoromethyl-5-pyridyl triazole, and the multi-substituted phenylpyridine iridium (III) complex can be obtained. The multi-substituted phenylpyridine iridium (III) complex has the advantages of blue light dual emission, extremely high quantum efficiency and the like, can serve as an electroluminescent phosphorescent material and a phosphorescent doping material to be used in an organic electroluminescent device, can achieve blue light emission, and can be doped with yellow-orange light to achieve white light emission.
Description
Technical field
The invention belongs to electroluminescent organic material technical field, be specifically related to a kind of Multi substituted benzenes yl pyridines iridium (III)
Coordination compound and its preparation method and application.
Background technology
Since C.W.Tang in 1987 finds 8-hydroxyquinoline aluminum (Alq first3) electroluminescent since, organic compound
Light electroluminescent of making peace receive the extensive concern of people.These organic luminescent compounds are widely used in organic light emission
The fields such as diode (OLEDs), organic sensing and bio-imaging.According to quantum theory, the machine luminescence of common are is divided into fluorescence
Luminous luminous with phosphorescence.But, for most pure organic molecule and light metal coordination compound, due to the long-life of its triplet state
And spin forbidden, thus show nonradiative transition, so only with its singletstate, significantly reducing sending out of this type of material
Photo-quantum efficiency.And transition metal is due to the heavy atoms effect of heavy atom, cause the strongest SO coupling effect so that
Singletstate is remarkably reinforced to the intersystem crossing of triplet state, thus the luminous quantum efficiency of phosphor material significantly improves, and i.e. utilizes
Cross metal and can make full use of the form of energy of singletstate and triplet state as electroluminescent material, increase substantially luminous effect
Rate, can make luminous quantum efficiency reach 100% in theory.
Transient metal complex currently used as luminescent material mainly has iridium (III), platinum (II), osmium (II), rhenium (I), copper
(I) heavy metal complex such as, is wherein hexa-coordinate ion due to iridium (III), can form neutral compound molecule, and iridium (III) is joined
The triplet lifetime of compound is shorter, has preferable luminescent properties, be the most most studied be also most to there is application prospect
One class phosphor material.
The glow color of iridium (III) coordination compound is strongly dependent on the structure of part, it is possible to select suitable master to join
Body and assistant ligand, and be chemically modified by electronegativity different to its introducing and the atom of volume or functional group, with regulation
The frontier molecular orbitals of iridium (III) complex molecule, thus the blue emitting phosphor realizing iridium (III) coordination compound is launched.
Summary of the invention
Solve the technical problem that: it is an object of the invention to provide a kind of Multi substituted benzenes yl pyridines iridium (III) coordination compound and
Preparation method and the application as phosphorescent light-emitting materials, this coordination compound has the characteristic that blue light pair is launched, quantum efficiency is high.
Technical scheme: a kind of Multi substituted benzenes yl pyridines iridium (III) coordination compound, its structural formula is as shown in formula I or II:
Wherein, R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
Further, R1、R4For hydrogen, R2、R3It is respectively trifluoromethyl or fluorine, R respectively5For hydrogen or methyl.
Further, R1For hydrogen, R2、R3、R4For fluorine, R5For hydrogen or methyl.
Further, R1、R2、R3、R4For fluorine, R5For hydrogen or methyl.
The preparation method of described Multi substituted benzenes yl pyridines iridium (III) coordination compound, comprises the following steps:
Step 1, under inert gas conditions, in alkoxyethanol dicyandiamide solution, by Multi substituted benzenes yl pyridines and three hydrations
Iridous chloride, in molar ratio 2～2.5:1 110 DEG C of reactions, obtains iridium (III) chlorine bridge dimer；
Step 2, in dichloromethane solvent system, in the presence of Anhydrous potassium carbonate, by iridium (III) chlorine bridge dimer and 2-pyrrole
Pyridine formic acid or 3-trifluoromethyl-5-pyridine triazole press 1:1.1～1.5 mol ratios 25 DEG C of reactions, obtain polysubstituted phenyl pyrazoline
Pyridine iridium (III) coordination compound,
Wherein, Multi substituted benzenes yl pyridines structural formula is as shown in formula III:
R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
Further, the mole of described Anhydrous potassium carbonate is 2-pyridine carboxylic acid or 3-trifluoromethyl-5-pyridine triazole
5-10 times of mole.
Further, described alkoxyethanol dicyandiamide solution is 2-methyl cellosolve or cellosolvo and water composition
Mixed solvent, wherein the volume ratio of 2-methyl cellosolve or cellosolvo and water is 3:1.
Above-mentioned Multi substituted benzenes yl pyridines iridium (III) coordination compound is as the application of organic electroluminescent phosphorescence luminescent material.
Above-mentioned Multi substituted benzenes yl pyridines iridium (III) coordination compound is having as the dopant material of organic electrophosphorescenpolymer material of main part
Application in organic electroluminescence devices.
A kind of organic electroluminescence device, including the first electrode, the second electrode, and the first electrode and the second electrode it
Between formed one or more layers organic function layer, one layer of organic function layer of at least a part of which includes described in Claims 1-4
Multi substituted benzenes yl pyridines iridium (III) coordination compound.
Beneficial effect: Multi substituted benzenes yl pyridines iridium (III) coordination compound of the present invention have blue light double launch, quantum efficiency high
Etc. characteristic, can serve as electroluminescent phosphorescence material and phosphorescence dopant material is applied in organic electroluminescence device, it is achieved be blue
Light emission, realizes white light emission with yellow orange light co-doped.
Accompanying drawing explanation
Fig. 1 is the coordination compound [3-CF of embodiment 13-4-Fppy]2Ir (pic) is in dichloromethane medium ultraviolet visible absorption spectra
And photoluminescence spectra；
Fig. 2 is the blue organic light-emitting devices of application examples 1 manufacture electroluminescent spectrum under different voltages；
Fig. 3 is the brightness of blue organic light-emitting devices that manufactures of application examples 1 and the electric current density change curve with voltage；
Fig. 4 is that the current efficiency of blue organic light-emitting devices that manufactures of application examples 1 and luminous efficiency are along with under electric current density
Change curve；
Fig. 5 is the organic electroluminescent white light device of application examples 2 manufacture electroluminescent spectrum under different voltages；
Fig. 6 is the brightness of organic electroluminescent white light device that manufactures of application examples 2 and the electric current density change curve with voltage；
Fig. 7 is that the current efficiency of organic electroluminescent white light device that manufactures of application examples 2 and luminous efficiency are along with under electric current density
Change curve.
Detailed description of the invention
The invention provides a kind of Multi substituted benzenes yl pyridines iridium (III) coordination compound, its structural formula is as shown in formula I or II:
Wherein, R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
The preparation method of described Multi substituted benzenes yl pyridines iridium (III) coordination compound, comprises the following steps:
Step 1, under inert gas conditions, in alkoxyethanol dicyandiamide solution, by Multi substituted benzenes yl pyridines and three hydrations
Iridous chloride, in molar ratio 2～2.5:1 110 DEG C of reactions, obtains iridium (III) chlorine bridge dimer；
Step 2, in dichloromethane solvent system, in the presence of Anhydrous potassium carbonate, by iridium (III) chlorine bridge dimer and 2-pyrrole
Pyridine formic acid or 3-trifluoromethyl-5-pyridine triazole press 1:1.1～1.5 mol ratios 25 DEG C of reactions, obtain polysubstituted phenyl pyrazoline
Pyridine iridium (III) coordination compound,
Wherein, Multi substituted benzenes yl pyridines structural formula is as shown in formula III:
R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
Multi substituted benzenes yl pyridines iridium (III) coordination compound of the present invention can be as organic electroluminescent phosphor material or organic
The phosphorescence dopant material of electro-phosphorescent main body material, is applied in organic electroluminescence device.
Multi substituted benzenes yl pyridines iridium (III) coordination compound of the present invention is used, by rationally in organic electroluminescence device
Ground selects suitable main part and assistant ligand, and by main part being introduced different electronegativity and the atom of volume or functional group
It is chemically modified, it is achieved the efficient blue light of target iridium (III) coordination compound is double to be launched, as electroluminescent phosphorescence material and phosphorescence
Dopant material, it is achieved the blue emission of organic electroluminescence device, realizes white light emission with yellow orange light co-doped.
The invention also discloses a kind of organic electroluminescence device, described organic electroluminescence device have the first electrode,
Second electrode, and one or more layers organic function layer formed between the first electrode and the second electrode, at least a part of which one layer
Organic function layer includes Multi substituted benzenes yl pyridines iridium (III) coordination compound of the present invention.
Preferably, Multi substituted benzenes yl pyridines iridium (III) coordination compound in organic electroluminescence device as phosphorescence host material
The dopant material of material, with the luminescent layer that phosphorescent light body material collectively forms organic electroluminescence device.Wherein, polysubstituted phenyl pyrazoline
Pyridine iridium (III) coordination compound is 1-9:100 with the weight ratio of phosphorescent light body material.
Described luminescent layer can use vacuum vapour deposition to prepare.Concrete technology is for join Multi substituted benzenes yl pyridines iridium (III)
Compound is deposited with small molecule host material the most simultaneously, is controlled each by two independent quartz oscillators
Evaporation rate, thus control both content.Little molecule as material of main part includes 9,9'-(1,3-phenyl) two-9H-click
Azoles (mCP), 4,4 '-N, N '-two carbazole biphenyl (CBP), 2-(4-diphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-diazole
(PBD), 1,3,5-tri-(2-N-phenyl benzimidazole groups) benzene (TPBI), 3-(4-diphenyl)-5-(4-tert-butyl-phenyl)-4-
(4-ethylphenyl)-, 1,2,4-triazole (TAZ) etc..Between anode ITO and luminescent layer, introduce sky by vacuum vapour deposition simultaneously
Cave transport layer, introduces one to two layer between metallic cathode and luminescent layer and has the organic little of hole barrier or electric transmission function
Molecular layer, to construct multilayer device.
The luminescent layer of organic electroluminescence device can also use solution spin-coating method to prepare.Concrete technology is by Multi substituted benzenes
Yl pyridines iridium (III) coordination compound is blended with macromolecule material of main part, is dissolved in chloroform, is spin-coated on through polythiofuran derivative
(PEDOT) modify or without the ito glass surface that it is modified, be prepared as luminescent layer.Macromolecule as material of main part includes gathering
Styrene support, polyhenylene, Polyvinyl carbazole, polycarbazole, polyfluorene or the derivant of polyfluorene.Additionally, it is all right in luminescent layer
It is further incorporated into little molecule carrier transmission material such as 2-(4-diphenyl)-5-(4-tert-butyl-phenyl)-1,3,4-diazole
(PBD), 1,3,5-tri-(2-N-phenyl benzimidazole groups) benzene (TPBI), 3-(4-diphenyl)-5-(4-tert-butyl-phenyl)-4-
(4-ethylphenyl)-, 1,2,4-triazole (TAZ), N, N '-bis-(3-aminomethyl phenyl)-N, N '-diphenyl-1,1 '-diphenyl-4,
4 '-diamidogen (TPD) or N, N '-two (1-naphthyl)-N, N '-diphenyl-1,1 '-diphenyl-4,4 '-diamidogen (NPB) etc..At device
In assembling, after the complete luminescent layer of spin coating, directly can make single layer device by evaporation metal electrode, it is also possible to vacuum vapour deposition is at metal electricity
It is further introduced into one to two-layer between pole and luminescent layer and there is the organic molecule layer structure of hole barrier or electric transmission function
Multilayer device.
Further describe the present invention below in conjunction with specific embodiment, but following embodiment is not used to limit this
The practical range of invention, every equivalence change done according to the technology of the present invention content and retouching, should be included in the present invention's
Within technology category.
Embodiment 1
Coordination compound [3-CF3-4-Fppy]2The synthesis of Ir (pic)
(1) synthesis of 2-(3-trifluoromethyl-4-fluorophenyl) pyridine
Take 2-bromopyridine 1.58g, 3-trifluoromethyl-4-fluorobenzoic boric acid 2.08g, tetrakis triphenylphosphine palladium (Pd (PPh3)4)
380mg, 8mL unsaturated carbonate aqueous solutions of potassium, 8mL absolute methanol, 25mL toluene, be added sequentially to the there-necked flask of band stirrer
In, logical nitrogen, back flow reaction 15h at 85 DEG C.Reaction terminates, and is cooled to room temperature, uses a large amount of dchloromethane, washes three times,
Natrium carbonicum calcinatum is dried organic facies, and decompression is spin-dried for, petroleum ether: ethyl acetate (70:1) column chromatography obtains colourless oil liquid, productivity
91%.1H NMR (400MHz, CDCl3) δ (ppm): 8.70 (ddd, J=4.8,1.6,0.9Hz, 1H), 8.28 (dd, J=6.9,
2.2Hz, 1H), 8.17 (ddd, J=8.1,4.7,2.3Hz, 1H), 7.81 7.75 (m, 1H), 7.70 (d, J=8.0Hz, 1H),
7.32–7.26(m,2H)。
(2) chlorine bridging Cyclometalated iridium (III) dimeric synthesis
Take 2-(3-trifluoromethyl-4-fluorophenyl) pyridine 301mg, three hydrated iridium trichloride 200mg, cellosolvo
9mL, deionized water 3mL, be sequentially added in two mouthfuls of flasks of band stirrer, logical nitrogen, is heated to 110 DEG C of return stirring reactions
24h, naturally cools to room temperature, pours 80mL deionized water in reactant liquor into, separates out a large amount of yellow green fluffy solid, filters, water
Wash rear 45 DEG C of vacuum drying, obtain greenish yellow solid.
(3) coordination compound [3-CF3-4-Fppy]2The synthesis of Ir (pic)
Take 2-(3-trifluoromethyl-4-fluorophenyl) pyridine close iridium (III) chlorine bridge dimer 402mg, 2-pyridine carboxylic acid 84mg,
Dichloromethane 40mL, Anhydrous potassium carbonate (grind into powder) 5g, be sequentially added in two mouthfuls of flasks of band stirrer, stirs under room temperature
Reaction 12h, filters, and repeatedly washs solid filter residue, merges organic facies, and decompression is spin-dried for, and dichloromethane column chromatography obtains light yellow solid.
1H NMR(400MHz,CDCl3) δ (ppm): 8.75 (d, J=5.5Hz, 1H), 8.35 (d, J=7.7Hz, 1H),
7.90 (m, J=37.5,28.3,14.3,3.1Hz, 9H), 7.48 7.43 (m, 1H), 7.41 (d, J=5.4Hz, 1H), 7.31
7.26 (m, 1H), 7.09 7.03 (m, 1H), 6.13 (d, J=11.0Hz, 1H), 5.89 (d, J=11.1Hz, 1H).19F NMR
(377MHz,CDCl3) δ (ppm) :-60.92 (dd, J=29.9,12.0Hz) ,-112.59 (q, J=11.9Hz) ,-113.50
(q, J=12.0Hz).
As it is shown in figure 1, coordination compound [3-CF3-4-Fppy]2The a length of 259nm of maximum absorption wave of Ir (pic), maximum emission peak
It is positioned at 466nm.
Embodiment 2
Coordination compound [3-CF3-4-Fppy]2The synthesis of Ir (fptz)
(1) synthesis of 3-trifluoromethyl-5-pyridine triazole (fptz)
I () joins 2-cyanopyridine full with Feldalat NM by mol ratio (5g:259mg) and the 50mL methanol of 10:1
In two mouthfuls of flasks of nitrogen, after 12h being stirred at room temperature under nitrogen protection, add the ammonium chloride with 2-cyanopyridine equivalent
(2.57g), stir 16h under room temperature, then, under reflux conditions (65 DEG C), react 4h, return to room temperature and filter unreacted chlorine
Changing ammonium, remove solvent in ambient temperature in vacuum, ether repeatedly washs to remove unreacted ammonium chloride further, filters, obtains white
Color acicular crystal 2-miaow ylpyridine hydrochloride.
(ii) Trifluoroacetic Acid Ethyl Ester and hydrazine hydrate press the mol ratio (7g:2.96g) of 1:1.2 with 30mL except the THF of water is molten
Liquid joins in two mouthfuls of flasks of full nitrogen, nitrogen protection under 12h is stirred at room temperature after, by with Trifluoroacetic Acid Ethyl Ester equivalent
NaOH Yu 2-miaow ylpyridine hydrochloride joins in above-mentioned reaction solution by the mol ratio of 1:1, vacuum nitrogen filling gas again, so
Rear 66 DEG C of back flow reaction 12h, obtain the solution of yellow, return to room temperature, remove solvent THF and be added thereto to deionization under vacuum
Water, then utilizes in saturated sodium bicarbonate solution and pH value, extracts by ethyl acetate from water, be dried with anhydrous magnesium sulfate simultaneously
Organic facies, removes ethyl acetate in vacuum, in vacuum drying oven, 50 DEG C of dry 12h, obtain white-yellowish solid, by ethyl acetate:
Normal hexane (1:3) carries out column chromatographic isolation and purification as eluent, and re-crystallizing in ethyl acetate obtains white needle-like crystals.
(2) synthesis of 2-(3-trifluoromethyl-4-fluorophenyl) pyridine
Take 2-bromopyridine 1.58g, 3-trifluoromethyl-4-fluorobenzoic boric acid 2.08g, tetrakis triphenylphosphine palladium (Pd (PPh3) 4)
380mg, 8mL unsaturated carbonate aqueous solutions of potassium, 8mL absolute methanol, 25mL toluene, be added sequentially to the there-necked flask of band stirrer
In, logical nitrogen, back flow reaction 15h at 85 DEG C.Reaction terminates, and is cooled to room temperature, uses a large amount of dchloromethane, washes three times,
Natrium carbonicum calcinatum is dried organic facies, and decompression is spin-dried for, petroleum ether: ethyl acetate (70:1) column chromatography obtains colourless oil liquid, productivity
91%.1H NMR(600MHz,CDCl3)δ(ppm):8.17-8.14(m；3H)；8.00(dd；J=1.20Hz；J=8.40Hz；
1H)；7.73(ddd；J=1.20Hz；J=7.20Hz；J=8.40Hz；1H)；7.67(q；J=0.60Hz；1H)；7.55(ddd；
J=1.20Hz；J=6.60Hz；J=8.40Hz；1H)；7.22-7.19(m；2H)；2.77(d；J=0.60Hz；3H).
(3) chlorine bridging Cyclometalated iridium (III) dimeric synthesis
Take 2-(3-trifluoromethyl-4-fluorophenyl) pyridine 301mg, three hydrated iridium trichloride 200mg, cellosolvo
9mL, deionized water 3mL, be sequentially added in two mouthfuls of flasks of band stirrer, logical nitrogen, is heated to 110 DEG C of return stirring reactions
24h, naturally cools to room temperature, pours 80mL deionized water in reactant liquor into, separates out a large amount of yellow green fluffy solid, filters, water
Wash rear 45 DEG C of vacuum drying, obtain greenish yellow solid.
(4) coordination compound [3-CF3-4-Fppy]2The synthesis of Ir (fptz)
Take 2-(3-trifluoromethyl-4-fluorophenyl) pyridine and close iridium (III) chlorine bridge dimer 402mg, 3-trifluoromethyl-5-pyrrole
Pyridine triazole 146mg, dichloromethane 40mL, Anhydrous potassium carbonate (grind into powder) 5g, be sequentially added into two mouthfuls of burnings of band stirrer
In Ping, under room temperature, stirring reaction 12h, filters, and repeatedly washs solid filter residue, merges organic facies, and decompression is spin-dried for, dichloromethane post layer
Analyse to obtain light yellow solid.1H NMR(400MHz,CDCl3) δ (ppm): 8.32 (d, J=7.9Hz, 1H), 7.98-7.86 (m, 4H),
7.86-7.76 (m, 3H), 7.74 (t, J=5.0Hz, 2H), 7.42 (d, J=5.8Hz, 1H), 7.28 (s, 1H), 7.25 (s,
1H), 7.10 (t, J=6.5Hz, 1H), 7.00 (t, J=6.7Hz, 1H), 6.08 (d, J=10.8Hz, 1H), 5.98 (d, J=
11.0Hz,1H)。19F NMR(377MHz,CDCl3) δ (ppm) :-60.91 (d, J=11.9Hz) ,-63.36 (s) ,-112.22
(q, J=12.0Hz) ,-112.67 (q, J=11.8Hz).
Application examples 1
Use embodiment 1 coordination compound [3-CF3-4-Fppy]2Ir (pic) is entrained in mCP material of main part manufacture organic electroluminescence
Luminescent device.First, it is deposited with the 4 of 45nm, 4'-cyclohexyl two [N, N-bis-(4-aminomethyl phenyl) on the surface being coated with ito glass
Aniline] (TAPC) as hole transmission layer.Then, hole transmission layer deposits doped with 10% [3-CF3-4-Fppy]2Ir
(pic) mCP forms the luminescent layer of 15nm, finally, is sequentially depositing hole blocking layer TmPyPB (35nm), electron transfer layer
Cs2CO3(2nm), boundary layer (LiF:1nm) and negative electrode (Al:150nm).
The electroluminescent spectrum of test device is as in figure 2 it is shown, maximum emission peak is positioned at 465nm, chromaticity coordinates CIE value X=
0.16, Y=0.30.Playing bright voltage is 3.7V.Current density-voltage-the brightness curve of device is as it is shown on figure 3, have preferably
Rectification characteristic, high-high brightness is 35000cd/m2, electric current density is 100mA/cm2Under brightness 16530cd/m2, in brightness it is
100cd/m2And electric current density is 100mA/cm2Under voltage be respectively 5.1V and 9.5V.Current efficiency-the brightness of device, power
As shown in Figure 4, maximum current efficiency and power efficiency are respectively 31.05cd/A and 17.41lm/W, brightness to ciency-luminance curve
100cd/m2Under current efficiency and power efficiency be respectively 30.96cd/A and 18.69lm/W, brightness 1000cd/m2Under electric current
Efficiency and power efficiency are respectively 26.37cd/A and 12.93lm/W, brightness 5000cd/m2Under current efficiency and power efficiency
It is respectively 22.20cd/A and 8.94lm/W.
Application examples 2
Use embodiment 1 coordination compound [3-CF3-4-Fppy]2Ir (pic) is complex doped in CBP material of main part with orange light
Manufacture organic electroluminescent white light device.First, it is deposited with N, N '-two (1-the naphthyl)-N of 60nm on the surface being coated with ito glass,
N '-diphenyl-1,1 '-diphenyl-4,4 '-diamidogen (NPB) and the 4,4' of 5nm, 4 "-three (carbazole-9-base) triphenylamine (TCTA)
As hole transmission layer.Then, hole transmission layer deposits doped with 4.5% [3-CF3-4-Fppy]2Ir (pic) and 0.5%
The CBP of orange light material forms the luminescent layer of 15nm, finally, is sequentially depositing hole blocking layer TmPyPB (35nm), electric transmission
Layer Cs2CO3(2nm), boundary layer (LiF:1nm) and negative electrode (Al:150nm).
Test device electroluminescent spectrum as it is shown in figure 5, spectrum is all warm white, chromaticity coordinates CIE value X=0.33, Y=
0.41.Playing bright voltage is 2.9V.Current density-voltage-the brightness curve of device as shown in Figure 6, has preferable rectification characteristic,
High-high brightness is 25000cd/m2, electric current density is 100mA/cm2Under brightness 10630cd/m2, it is 100cd/m in brightness2And
Electric current density is 100mA/cm2Under voltage be respectively 3.9V and 8.1V.Current efficiency-the brightness of device, power efficiency-brightness
Curve is as it is shown in fig. 7, maximum current efficiency and power efficiency are respectively 34.29cd/A and 26.07lm/W, brightness 100cd/m2Under
Current efficiency and power efficiency be respectively 31.55cd/A and 26.07lm/W, brightness 1000cd/m2Under current efficiency and merit
Rate efficiency is respectively 28.43cd/A and 17.85lm/W, brightness 5000cd/m2Under current efficiency and power efficiency be respectively
19.61cd/A and 9.62lm/W.
Claims (10)
1. Multi substituted benzenes yl pyridines iridium (III) coordination compound, it is characterised in that: its structural formula is as shown in formula I or II:
Wherein, R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
Multi substituted benzenes yl pyridines iridium (III) coordination compound the most according to claim 1, it is characterised in that: R1、R4For hydrogen, R2、R3
It is respectively trifluoromethyl or fluorine, R respectively5For hydrogen or methyl.
Multi substituted benzenes yl pyridines iridium (III) coordination compound the most according to claim 1, it is characterised in that: R1For hydrogen, R2、R3、R4
For fluorine, R5For hydrogen or methyl.
Multi substituted benzenes yl pyridines iridium (III) coordination compound the most according to claim 1, it is characterised in that: R1、R2、R3、R4For
Fluorine, R5For hydrogen or methyl.
5. the preparation method of Multi substituted benzenes yl pyridines iridium (III) coordination compound described in Claims 1-4, it is characterised in that: include
Following steps:
Step 1, under inert gas conditions, in alkoxyethanol dicyandiamide solution, by Multi substituted benzenes yl pyridines and three hydration trichlorines
Change iridium in molar ratio 2～2.5:1 110 DEG C of reactions, obtain iridium (III) chlorine bridge dimer；
Step 2, in dichloromethane solvent system, in the presence of Anhydrous potassium carbonate, by iridium (III) chlorine bridge dimer and 2-pyridine first
Acid or 3-trifluoromethyl-5-pyridine triazole press 1:1.1～1.5 mol ratios 25 DEG C of reactions, obtain Multi substituted benzenes yl pyridines iridium
(III) coordination compound,
Wherein, Multi substituted benzenes yl pyridines structural formula is as shown in formula III:
R1、R2、R3、R4、R5It is each independently hydrogen, fluorine, methyl or trifluoromethyl.
The preparation method of Multi substituted benzenes yl pyridines iridium (III) coordination compound the most according to claim 5, it is characterised in that: institute
Stating the mole of Anhydrous potassium carbonate is 2-pyridine carboxylic acid or 5-10 times of 3-trifluoromethyl-5-pyridine triazole mole.
The preparation method of Multi substituted benzenes yl pyridines iridium (III) coordination compound the most according to claim 5, it is characterised in that: institute
State the mixed solvent that alkoxyethanol dicyandiamide solution is 2-methyl cellosolve or cellosolvo and water composition, wherein 2-methoxy
The volume ratio of base ethanol or cellosolvo and water is 3:1.
8. Multi substituted benzenes yl pyridines iridium (III) coordination compound described in Claims 1-4 is as organic electroluminescent phosphorescence luminescent material
Application.
9. Multi substituted benzenes yl pyridines iridium (III) coordination compound described in Claims 1-4 is as organic electrophosphorescenpolymer material of main part
Dopant material application in organic electroluminescence device.
10. an organic electroluminescence device, including the first electrode, the second electrode, and the first electrode and the second electrode it
Between formed one or more layers organic function layer, it is characterised in that: at least one of which organic function layer includes claim 1 to
Multi substituted benzenes yl pyridines iridium (III) coordination compound described in 4.
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| CN108467412A (en) * | 2018-03-16 | 2018-08-31 | 南京邮电大学 | A kind of green-yellow light phenylpyridine complex of iridium and its preparation method and application |
| CN114163379A (en) * | 2021-04-19 | 2022-03-11 | 闽都创新实验室 | Fluorocarbazolyl diphenylethylene biphenyl compound and preparation method and application thereof |
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