CN1520702A - 含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件 - Google Patents
含有氟化苯基吡啶、苯基嘧啶和苯基喹啉的电致发光铱化合物及用该化合物制备的器件 Download PDFInfo
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- CN1520702A CN1520702A CNA018232167A CN01823216A CN1520702A CN 1520702 A CN1520702 A CN 1520702A CN A018232167 A CNA018232167 A CN A018232167A CN 01823216 A CN01823216 A CN 01823216A CN 1520702 A CN1520702 A CN 1520702A
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- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical class C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 150000001875 compounds Chemical class 0.000 title claims description 147
- 150000005359 phenylpyridines Chemical class 0.000 title description 6
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003446 ligand Substances 0.000 claims description 57
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 43
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 16
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 11
- 150000002527 isonitriles Chemical class 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- XUDAGRPFMIKMQK-UHFFFAOYSA-N 1-isocyano-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC([N+]#[C-])=C1 XUDAGRPFMIKMQK-UHFFFAOYSA-N 0.000 claims description 2
- DNJLFZHMJDSJFN-UHFFFAOYSA-N 2-isocyano-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1[N+]#[C-] DNJLFZHMJDSJFN-UHFFFAOYSA-N 0.000 claims description 2
- QSACPWSIIRFHHR-UHFFFAOYSA-N dimethylphenyl isocyanide Natural products CC1=CC=CC(C)=C1C#N QSACPWSIIRFHHR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- ITJHLZVYLDBFOJ-UHFFFAOYSA-N tris[3,5-bis(trifluoromethyl)phenyl]phosphane Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(P(C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)C=2C=C(C=C(C=2)C(F)(F)F)C(F)(F)F)=C1 ITJHLZVYLDBFOJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000005360 2-phenylpyridines Chemical class 0.000 abstract description 7
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 abstract description 5
- 239000010410 layer Substances 0.000 description 106
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 61
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 49
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- 239000000203 mixture Substances 0.000 description 42
- 239000000463 material Substances 0.000 description 31
- 229910052741 iridium Inorganic materials 0.000 description 30
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 238000004293 19F NMR spectroscopy Methods 0.000 description 24
- 238000005160 1H NMR spectroscopy Methods 0.000 description 22
- 239000007787 solid Substances 0.000 description 22
- -1 8-hydroxyquinolinate (quinolate) Chemical compound 0.000 description 21
- 150000002504 iridium compounds Chemical class 0.000 description 21
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000000034 method Methods 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 150000002503 iridium Chemical class 0.000 description 15
- YMWUJEATGCHHMB-DICFDUPASA-N deuterated dichloromethane Substances [2H]C([2H])(Cl)Cl YMWUJEATGCHHMB-DICFDUPASA-N 0.000 description 14
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 13
- 239000002184 metal Substances 0.000 description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- 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 12
- 238000002360 preparation method Methods 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 238000005401 electroluminescence Methods 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- 230000005525 hole transport Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- 229940093475 2-ethoxyethanol Drugs 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- KBXXZTIBAVBLPP-UHFFFAOYSA-N 4-[[4-(diethylamino)-2-methylphenyl]-(4-methylphenyl)methyl]-n,n-diethyl-3-methylaniline Chemical compound CC1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)N(CC)CC)C)C1=CC=C(C)C=C1 KBXXZTIBAVBLPP-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000004364 calculation method Methods 0.000 description 5
- 238000000151 deposition Methods 0.000 description 5
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- AAOXLOHKUSXMGM-UHFFFAOYSA-N 1-(2,4-difluorophenyl)isoquinoline Chemical compound FC1=CC(F)=CC=C1C1=NC=CC2=CC=CC=C12 AAOXLOHKUSXMGM-UHFFFAOYSA-N 0.000 description 4
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
- DHDHJYNTEFLIHY-UHFFFAOYSA-N 4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=CN=C21 DHDHJYNTEFLIHY-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 238000010791 quenching Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- HXFVJCBIRYKDRY-UHFFFAOYSA-N 1,2-dichloroethane;hexane Chemical compound ClCCCl.CCCCCC HXFVJCBIRYKDRY-UHFFFAOYSA-N 0.000 description 3
- UDGYLQTZGJGKPC-UHFFFAOYSA-N 2-(4-fluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(F)(F)F)C=N1 UDGYLQTZGJGKPC-UHFFFAOYSA-N 0.000 description 3
- BCJVBDBJSMFBRW-UHFFFAOYSA-N 4-diphenylphosphanylbutyl(diphenyl)phosphane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCCP(C=1C=CC=CC=1)C1=CC=CC=C1 BCJVBDBJSMFBRW-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 239000007983 Tris buffer Substances 0.000 description 3
- 125000000129 anionic group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 230000008021 deposition Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 3
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 2
- STTGYIUESPWXOW-UHFFFAOYSA-N 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline Chemical compound C=12C=CC3=C(C=4C=CC=CC=4)C=C(C)N=C3C2=NC(C)=CC=1C1=CC=CC=C1 STTGYIUESPWXOW-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 2
- 229920001774 Perfluoroether Polymers 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- OFZPMMOCGPTHPA-UHFFFAOYSA-M [OH-].[Ir+] Chemical group [OH-].[Ir+] OFZPMMOCGPTHPA-UHFFFAOYSA-M 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 229910052788 barium Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000001194 electroluminescence spectrum Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 2
- YOLNUNVVUJULQZ-UHFFFAOYSA-J iridium;tetrachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Ir] YOLNUNVVUJULQZ-UHFFFAOYSA-J 0.000 description 2
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- DOWVMJFBDGWVML-UHFFFAOYSA-N n-cyclohexyl-n-methyl-4-(1-oxidopyridin-1-ium-3-yl)imidazole-1-carboxamide Chemical compound C1=NC(C=2C=[N+]([O-])C=CC=2)=CN1C(=O)N(C)C1CCCCC1 DOWVMJFBDGWVML-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000011241 protective layer Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000003595 spectral effect Effects 0.000 description 2
- 238000004611 spectroscopical analysis Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 0.000 description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- 238000001429 visible spectrum Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- QQLRSCZSKQTFGY-UHFFFAOYSA-N (2,4-difluorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(F)C=C1F QQLRSCZSKQTFGY-UHFFFAOYSA-N 0.000 description 1
- MSQCQINLJMEVNJ-UHFFFAOYSA-N 1-chloroisoquinoline Chemical compound C1=CC=C2C(Cl)=NC=CC2=C1 MSQCQINLJMEVNJ-UHFFFAOYSA-N 0.000 description 1
- UJKZZDIDXPYBID-UHFFFAOYSA-N 1-diphenylphosphanylpropan-1-ol Chemical compound C=1C=CC=CC=1P(C(O)CC)C1=CC=CC=C1 UJKZZDIDXPYBID-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- PPUIIGZBBURFML-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=CC=C1C1=CC=C(C(F)(F)F)C=N1 PPUIIGZBBURFML-UHFFFAOYSA-N 0.000 description 1
- SEWNWACDICHTTP-UHFFFAOYSA-N 2-(3,5-difluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound FC1=CC(F)=CC(C=2N=CC(=CC=2)C(F)(F)F)=C1 SEWNWACDICHTTP-UHFFFAOYSA-N 0.000 description 1
- WNCPHYQOEBGTSR-UHFFFAOYSA-N 2-(3-methoxyphenyl)-5-(trifluoromethyl)pyridine Chemical compound COC1=CC=CC(C=2N=CC(=CC=2)C(F)(F)F)=C1 WNCPHYQOEBGTSR-UHFFFAOYSA-N 0.000 description 1
- QIYHCQVVYSSDTI-UHFFFAOYSA-N 2-(phenyliminomethyl)phenol Chemical compound OC1=CC=CC=C1C=NC1=CC=CC=C1 QIYHCQVVYSSDTI-UHFFFAOYSA-N 0.000 description 1
- JFZJMSDDOOAOIV-UHFFFAOYSA-N 2-chloro-5-(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=C(Cl)N=C1 JFZJMSDDOOAOIV-UHFFFAOYSA-N 0.000 description 1
- 150000005759 2-chloropyridine Chemical class 0.000 description 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
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Images
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/26—Radicals substituted by halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/26—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- 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
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
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Abstract
Description
表1 | ||||||||||
化合物 | A | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | 分子式 |
1-a | C | H | H | CF3 | H | H | H | H | H | 第四 |
1-b | C | H | H | CF3 | H | H | H | F | H | 第四 |
1-c | C | H | H | CF3 | H | F | H | H | H | 第四 |
1-d | C | H | H | H | H | F | H | H | H | 第四 |
1-e | C | H | H | CF3 | H | H | CF3 | H | H | 第四 |
1-f | C | H | H | H | H | H | CF3 | H | H | 第四 |
1-g | C | H | H | H | H | H | H | F | H | 第四 |
表1 | ||||||||||
化合物 | A | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | 分子式 |
1-h | C | Cl | H | CF3 | H | H | H | H | H | 第四 |
1-i | C | H | H | CF3 | H | H | H | OCH3 | H | 第四 |
1-j | C | H | H | CF3 | H | H | F | H | H | 第四 |
1-k | C | H | H | NO2 | H | H | CF3 | H | H | 第四 |
1-l | C | H | H | CF3 | H | H | H | OCF3 | H | 第四 |
1-m | N | -- | CF3 | H | H | H | H | F | H | 第四 |
1-q | C | H | H | CF3 | H | H | OCH3 | H | H | 第四 |
1-r | C | H | OCH3 | H | H | H | H | CF3 | H | 第四 |
1-s | C | H | H | H | H | F | H | F | H | 第四和第五 |
1-t | C | H | H | CF3 | H | H | F | H | F | 第五 |
1-u | C | H | H | CF3 | H | F | H | F | H | 第五 |
1-v | C | H | H | CF3 | H | H | H | F | H | 第五 |
表2 | ||||||||||
化合物 | A | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 |
2-a | C | H | H | CF3 | H | F | H | H | H | H |
2-b | C | H | H | CF3 | H | H | CF3 | H | H | H |
2-c | C | H | H | NO2 | H | H | CF3 | H | H | H |
2-d | C | H | H | CF3 | H | H | F | H | H | H |
2-e | C | H | H | CF3 | H | H | H | CH3O | H | H |
2-f | C | Cl | H | CF3 | H | H | H | H | H | H |
2-g | C | H | H | H | CH3 | H | H | F | H | H |
2-h | N | -- | H | H | H | H | H | F | H | H |
2-i | C | H | H | CF3 | H | H | H | CF3O | H | H |
2-j | N | -- | CF3 | H | H | F | H | H | H | H |
2-k | C | H | H | CF3 | H | H | H | F | H | H |
2-l | C | CF3 | H | H | H | H | H | H | H | H |
2-m | C | Cl | H | CF3 | H | H | H | F | H | H |
2-n | C | CF3 | H | H | H | H | H | F | H | H |
2-o | C | CF3 | H | H | H | H | H | CH3O | H | H |
2-p | C | Cl | H | CF3 | H | H | H | CH3O | H | H |
2-q | N | -- | CF3 | H | H | H | H | F | H | H |
2-r | C | Cl | H | CF3 | H | H | H | H | H | F |
2-s | C | H | H | CF3 | H | H | H | H | H | H |
2-t | C | Cl | H | H | H | F | H | H | H | H |
2-v | C | H | H | CF3 | H | H | CH3O | H | H | H |
2-w | C | H | CH3O | H | H | H | H | CF3 | H | H |
2-x | C | H | H | H | H | H | F | F | H | H |
2-y | C | H | H | CF3 | H | H | F | H | F | H |
2-z | C | H | H | CF3 | H | F | H | F | H | H |
2-aa | C | H | H | Br | H | H | H | Br | H | H |
化合物 | 配合物分子式 | 配体结构 | R取代基 | L′ |
8-a | 第二 | I | R3=CF3R7=F | Me-8hq |
8-b | 第二 | I | R3=CF3R7=F | 8hq |
8-c | 第二 | XI | R18=CF3 | acac |
8-d | 第二 | XII | R29=CF3 | acac |
8-e | 第二 | XII | R28=CF3 | acac |
8-f | 第二 | XII | R29=F | acac |
8-g | 第二 | XII | R27=FR29=F | acac |
8-h | 第二 | XII | R27=FR29=FR30=F | acac |
8-i | 第二 | XII | R28=FR29=FR30=F | acac |
8-j | 第二 | XII | R28=FR30=F | acac |
8-k | 第二 | XII | R29=C8F17 | acac |
8-l | 第三 | XII | R29=CF3 | - |
8-m | 第三 | XII | R28=FR29=FR30=F | - |
8-n | 第三 | XII | R27=FR29=FR30=F | - |
8-o | 第三 | XII | R27=FR29=F | - |
8-p | 第三 | XII | R28=CF3 | - |
8-q | 第三 | XII | R28=FR30=F | - |
8-r | 第二 | XII | R27=FR29=F | acac |
8-s | 第二 | XII | R29=OCF3 | acac |
化合物 | L’ | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
9-a | NC-1 | H | CH3 | H | H | F | H | F | H |
9-b | NC-1 | H | H | CH3 | H | F | H | F | H |
9-c | NC-1 | H | H | H | H | F | H | F | H |
9-d | NC-1 | H | H | H | H | H | CF3 | H | H |
9-e | NC-1 | H | CH3 | H | H | H | CF3 | H | H |
9-f | NC-1 | H | H | CF3 | H | H | H | F | H |
9-g | NC-1 | H | H | CF3 | H | H | CF3 | H | H |
9-h | NC-2 | H | H | H | H | H | CF3 | H | H |
9-i | NC-3 | H | H | CF3 | H | H | H | F | H |
9-j | PPh3 | H | H | CF3 | H | H | H | F | H |
化合物 | L’ | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 |
9-k | PtmPh3 | H | H | CF3 | H | H | H | F | H |
9-l | CO | H | H | CF3 | H | H | H | F | H |
表5 | ||
化合物 | 分析(计算(实测)) | NMR(CD2Cl2,25℃) |
1-a | C:50.3(50.1)H:2.5(2.7)N:4.9(4.9)Cl:0.0(0.2) | 1H:6.8(1H),6.9(1H),7.0(1H),7.8(2H),7.95(1H),8.1(1H)19F:-63.4 |
1-b | C:47.4(47.3)H:2.0(2.1)N:4.6(4.4) | 1H:6.4(1H),6.75(1H),7.7(1H),7.8(1H),7.95(1H),8.05(1H)19F:-63.4(s);-109.5(ddd) |
1-c | C:47.4(47.2)H:2.0(2.0)N:4.6(4.5) | 1H:6.6(1H),6.7(1H),6.9(1H),7.8(1H),8.0(1H),8.6(1H)19F:-63.5(s);-112.8(ddd) |
1-d | C:55.9(56.1)H:3.0(3.2)N:5.9(5.8) | 1H:6.6(2H),6.8(1H),7.0(1H),7.6(1H),7.7(1H),8.4(1H)19F:-115.0(ddd) |
1-e | C:44.1(43.3)H:1.7(2.1)N:3.9(3.6) | 1H:6.9(1H),7.1(1H),7.8(1H),8.0(2H),8.2(1H)19F:-63.0(1F),-63.4(1F) |
1-f | C:50.4(50.5)H:2.5(2.7)N:4.9(4.9) | 1H:6.9(1H),7.1(2H),7.6(1H),7.8(1H),7.9(1H),8.1(1H)19F:-62.4 |
1-g | C:55.9(56.3)H:3.0(3.2)N:5.9(6.0) | 1H;6.4(1H),6.7(1H),7.0(1H),7.6(1H),7.7(2H),7.9(1H)19F:-112.6(ddd) |
表5(续) | ||
化合物 | 分析(计算(实测)) | NMR(CD2Cl2,25℃) |
1-h | C:51.0(45.2)H:2.1(2.3)N:4.9(4.2) | 1H:6.8(1H),6.95(1H),7.05(1H),7.7(1H),8.0(1H),8.9(1H)19F:-63.3 |
1-i | C:49.4(49.3)H:2.9(2.8)N:4.4(4.4) | 1H:3.6(3H),6.3(1H),6.6(1H),7.7(2H),7.85(1H),7.95(1H)19F:-63.2 |
1-j | C:47.4(47.4)H:2.0(2.3)N:4.6(4.7) | 1H:6.7(m),7.1(m),7.5(m),7.6(m),7.7(m),8.0(m),8.2(m)19F:8s resonances(-63.0--63.6)and 8 ddd resonances (-92.2--125.5) |
1-k | C:43.5(44.0)H:1.8(2.1)N:8.5(8.4) | 1H:6.9(1H),7.15(1H),8.1(1H),8.3(1H),8.45(1H),8.6(1H)19F:-62.9 |
1-l | C:42.2(42.1)H:16.(1.8)N:3.8(3.7) | 1H:6.5(1H),6.7(1H),7.75(1H),7.85(1H),8.0(1H),8.1(1H)19F:-58.1(1F),-63.4(1F) |
表6Alq3=三(8-羟基喹啉合)铝DDPA=2,9-二甲基-4,7-二苯基-1,10-菲咯啉Ir(ppy)3=面式-三(2-苯基吡啶)铱MPMP=二[4-(N,N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷 | |||
样品 | HT层(厚度,_) | EL层(厚度,_) | ET层(厚度,_) |
对比 | MPMP(528) | Ir(ppy)3(408) | DDPA(106)+Alq3(320) |
1 | MPMP(520) | 化合物 1-b(499) | DDPA(125)+Alq3(365) |
2 | MPMP(541) | 化合物 1-b(580) | DDPA(407) |
3 | MPMP(540) | 化合物 1-e(499) | DDPA(112)+Alq3(340) |
4 | MPMP(525) | 化合物 1-k(406) | DDPA(106)Alq3(341) |
样品 | HT层(厚度,_) | EL层(厚度,_) | ET层(厚度,_) |
5 | MPMP(570) | 化合物 1-i(441) | DDPA(107)+Alq3(339 |
6 | MPMP(545) | 化合物 1-i(462) | DDPA(111)+Alq3(319) |
7 | MPMP(643) | 化合物 1-g(409) | DDPA(112)+Alq3(361) |
8 | MPMP(539) | 化合物 1-f(430) | DDPA(109)+Alq3(318) |
9 | MPMP(547) | 化合物 1-a(412) | DDPA(105)+Alq3(300) |
10 | MPMP(532) | 化合物 1-h(457) | DDPA(108)+Alq3(306) |
11 | MPMP(603) | 化合物 1-d | DDPA(111)+Alq3(303) |
(415) | |||
12 | MPMP(551) | 化合物 1-c(465) | DDPA(106)+Alq3(313) |
13 | MPMP(520) | 化合物 1-l(405) | DDPA(410) |
14 | MPMP(504) | 化合物 1-b(400) | DDPA(393) |
15 | MPMP(518) | 化合物 1-b(153) | DDPA(418) |
16 | MPMP(556) | 化合物 1-m(416) | DDPA(430) |
17 | MPMP(520) | 化合物 1-n(419) | DDPA(420) |
18 | MPMP(511) | 化合物 1-o(412) | DDPA(413) |
19 | MPMP(527) | 化合物 1-p(425) | DDPA(412) |
20 | MPMP(504) | 化合物1-q(417) | DPA(407) |
21 | MPMP(525) | 化合物1-t(419) | DPA(416) |
22 | MPMP(520) | 化合物1-u(421) | DPA(405) |
表7铱化合物的电致发光性能 | ||||
样品 | 峰值辐射率,Cd/m2 | 峰值辐射处的效率,Cd/A | 峰值效率,Cd/A | 近似峰值波长,nm |
对比 | 540在22V | 0.39 | 0.48 | 522 |
1 | 1400在21V | 3.4 | 11 | 525 |
2 | 1900在25V | 5.9 | 13 | 525 |
3 | 830在18V | 1.7 | 13.5 | 525 |
4 | 7.6在27V | 0.005 | 0.13 | 521 |
5 | 175在25V | 0.27 | 1.8 | 530,563 |
6 | 514在20V | 1.5 | 2.2 | 560 |
7 | 800在26V | 0.57 | 1.9 | 514 |
8 | 1200在28V | 0.61 | 2 | 517 |
9 | 400在18V | 1.1 | 4 | 545 |
10 | 190在16V | 2.3 | 3.3 | 575 |
11 | 1150在25V | 1.2 | 3.8 | 506,526 |
12 | 340在20V | 0.49 | 2.1 | 525 |
13 | 400在21V | 3 | 5 | 520 |
14 | 1900 | 5 | 9 | 525 |
15 | 2500 | 6 | 11 | 525 |
16 | 100在27V | 0.17 | 0.2 | 560 |
17 | 3.5在28V | 0.005 | 0.014 | 575 |
18 | 30在26V | 0.08 | 0.16 | 590 |
表7(续) | ||||
样品 | 峰值辐射率,Cd/m2 | 峰值辐射处的效率,Cd/A | 峰值效率,Cd/A | 近似峰值波长,nm |
19 | 2000在21V | 6 | 8 | 532 |
20 | 350在26V | 0.60 | 1.6 | 595 |
21 | 1200在22V | 5 | 545 | |
22 | 80在19V | 1 | 540 |
表10MPMP=二[4-(N,N-二乙基氨基)-2-甲基苯基](4-甲基苯基)-甲烷DPA=4,7-二苯基-1,10-菲咯啉 | |||
样品 | HT层(厚度,_) | EL层(厚度,_) | ET层(厚度,_) |
11-1 | MPMP(572) | 化合物 8-a(419) | DPA(400) |
11-2 | MPMP(512) | 化合物 8-b(407) | DPA(394) |
11-3 | MPMP(548) | 化合物 8-c(441) | DPA(408) |
11-4 | MPMP(508) | 化合物8-d(410) | DPA(408) |
11-5 | MPMP(560) | 化合物8-e(421) | DPA(407) |
11-6 | MPMP(526) | 化合物8-f(409) | DPA(405) |
表10MPMP=二[4-(N,N-二乙基氨基)-2-甲基苯基](4-甲基苯基)-甲烷DPA=4,7-二苯基-1,10-菲咯啉 | |||
样品 | HT层(厚度,_) | EL层(厚度,_) | ET层(厚度,_) |
11-7 | MPMP(890) | 化合物8-g(408) | DPA(402) |
11-8 | MPMP(514) | 化合物8-h(465) | DPA(403) |
11-9 | MPMP(564) | 化合物8-i(418) | DPA(413) |
11-10 | MPMP(564) | 化合物8-j(405) | DPA(407) |
11-11 | MPMP(522) | 化合物8-k(400) | DPA(408) |
11-12 | MPMP(529) | 化合物8-l(421) | DPA(408) |
11-13 | MPMP(530) | 化合物8-m(411) | DPA(411) |
11-14 | MPMP(537) | 化合物8-o(412) | DPA(409) |
11-15 | MPMP(509) | 化合物8-p(405) | DPA(405) |
11-16 | MPMP(512) | 化合物8-q(414) | DPA(402) |
11-17 | MPMP(529) | 化合物8-r(442) | DPA(412) |
11-18102961-31 | MPMP(524) | 化合物8-s(407) | DPA(408) |
表11铱化合物的电致发光性质 | ||||
样品 | 峰值辐射率,Cd/m2 | 峰值效率Cd/A | 近似峰值波长,nm | |
11-1 | 45在22V | 0.13 | 628 | |
11-2 | 32在20V | 0.12 | >600 | |
11-3 | 340在24 | 2.5 | 590 | |
11-4 | 350在22V | 1.7 | 625 | |
11-5 | 300在21V | 1.5 | >600 | |
11-6 | 200在20V | 1.1 | 605,650 | |
11-7 | 300在23V | 5 | 605 | |
11-8 | 280在21V | 2.9 | 590 | |
11-9 | 1000在20V | 3.5 | 592 | |
11-10 | 380在21V | 2.3 | 610,650 | |
11-11 | 8在23V | 0.25 | 624 | |
11-12 | 800在20V | 2.3 | 610,650 | |
11-13 | 360在22V | 1.5 | 590 | |
11-14 | 160在24V | 1.2 | 590 | |
11-15 | 80在21V | 1.1 | 597 | |
11-16 | 170在21V | 0.8 | 615 | |
11-17 | 1300在22V | 4 | 600 | |
11-18 | 540在20V | 1.6 | 622 |
表12 | ||||||||||
化合物 | A | R1 | R2 | R3 | R4 | R5 | R6 | R7 | R8 | R9 |
12-a | C | H | CH3 | H | H | F | H | F | H | H |
12-b | C | H | CH3 | H | H | H | CF3 | H | CF3 | H |
12-c | C | H | H | CH3 | H | F | H | F | H | H |
12-d | C | H | CH3 | H | H | H | CF3 | H | H | H |
12-e | C | H | H | CH3 | H | H | CF3 | H | CF3 | H |
12-f | C | H | H | H | H | H | CF3 | H | H | H |
12-g | C | H | H | H | H | F | H | F | H | H |
12-h | C | H | t-Bu | H | H | H | H | F | H | H |
12-i | C | H | t-Bu | H | H | H | CF3 | H | CF3 | H |
12-j | C | H | CH3 | H | H | H | H | CF3 | H | H |
化合物 | 产率(%) | B.p./mmHg(m.p.)℃ | NBNo | 1HNMR | 19FNMR |
12-a | 61.5 | 70-72/0.03 | 101394-104 | 2.39(3H),6.99(2H),7.02(1H),7.57(1H),7.99(1H)8.56(1H) | -102.96(1F,m),-113.18(1F,m) |
化合物 | 产率(%) | B.p./mm Hg(m.p.)℃ | NBNo | 1HNMR | 19F NMR |
12-b | 39 | 66-68/0.01 | 101394-115 | 2.47(3H),7.17(1H),7.63(1H),7.91(1H),8.48(2H),8.60(1H),9.00(1H) | -63.23(s) |
12-c | 76 | 75-76/0.01(54-56) | 101394-121 | 2.25(3H),6.90(2H),7.55(2H)8.50(1H),8.85(1H), | -110.37(1F,m)-113.50(1F,m) |
12-d | 76 | 69-70/0.06(44-46) | 101394-129 | 2.35(3H),7.05(1H),7.55(2H),8.01(1H),8.18(1H),8.50(1H) | -63.03(s) |
12-e | 84 | (83-85) | 102960-48 | 2.43(3H)7.66(1H),7.87(1H),8.47(2H),8.59(1H) | -63.18(s) |
12-f | 72 | 64-65/0.026 | 99344-13 | 7.20(1H),7.65(3H),8.10(1H),8.17(1H),8.65(1H),9.43(1H) | -63.05(s) |
化合物 | 产率(%) | B.p./mmHg(m.p.)℃ | NBNo | 1HNMR | 19FNMR |
12-g | 36 | 62/0.01 | 101394-93 | 6.90(1H),7.18(2H),7.68(2H),7.95(1H),8.65(1H), | -109.70(1F, m)-113.35(1F,m) |
12-h | 49 | 99-101/0.26 | 102960-117 | - | - |
12-i | 58 | 108-109/0.1 | 103555-3 | 1.35(9H)7.34(1H)7.72(1H)7.88(1H)8.44(2H)8.61(1H) | -63.19 |
12-j | 46 | 76-77/01(52-54) | 102960-143 | 2.46(3H)7.15(1H)7.60(1H)7.73(2H)8.11(2H)8.59(1H) | -62.86 |
表14MPMP=二[4-(N,N-二乙基氨基)-2-甲基苯基](4-甲基苯基)甲烷DPA=4,7-二苯基-1,10-菲咯啉 | |||
样品 | HT层(厚度,A) | EL层(厚度,A) | ET层(厚度,A) |
15-1 | MPMP(516) | 化合物9-a(408) | DPA(413) |
15-2 | MPMP(518) | 化合物9-c(404) | DPA(402) |
15-3 | MPMP(508) | 化合物9-d(354) | DPA(421) |
15-4 | MPMP(504) | 化合物9-e(403) | DPA(410) |
15-5102924-5 | MPMP(501) | 化合物9-f(407) | DPA(415) |
15-6102924-40 | MPMP(518) | 化合物9-g(404) | DPA(405) |
表15铱化合物的电致发光性质 | |||
样品 | 峰值辐射率Cd/m2 | 峰值效率Cd/=A | 近似峰值波长nm |
15-1 | 6在16V | 0.7 | 450+500 |
15-2 | 1在21V | 0.25 | 510 |
15-3 | 60在22V | 0.8 | 464+493 |
表15铱化合物的电致发光性质 | |||
样品 | 峰值辐射率Cd/m2 | 峰值效率Cd/A | 近似峰值波长nm |
15-4 | 25在23V | 1.2 | 460+512 |
15-5 | 320在22V | 2.4 | 538 |
15-6 | 350在23V | 1.5 | 484+509 |
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- 2001-12-26 EP EP10011546A patent/EP2299785A1/en not_active Withdrawn
- 2001-12-26 IL IL15831401A patent/IL158314A0/xx unknown
- 2001-12-26 EP EP10012651A patent/EP2306788A1/en not_active Withdrawn
- 2001-12-26 EP EP01991428A patent/EP1466506A4/en not_active Withdrawn
- 2001-12-26 CN CN018232167A patent/CN1520702B/zh not_active Expired - Lifetime
- 2001-12-26 JP JP2003563272A patent/JP4299144B2/ja not_active Expired - Lifetime
- 2001-12-26 EP EP10012691A patent/EP2306789A1/en not_active Withdrawn
- 2001-12-26 WO PCT/US2001/049522 patent/WO2003063555A1/en active Application Filing
- 2001-12-26 CA CA002455844A patent/CA2455844A1/en not_active Abandoned
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CN103224534A (zh) * | 2008-01-29 | 2013-07-31 | 葛来西雅帝史派有限公司 | 新颖的有机电致发光化合物和使用该化合物的有机电致发光器件 |
CN110818742A (zh) * | 2009-04-28 | 2020-02-21 | 通用显示公司 | 具有甲基-d3取代的铱配合物 |
CN102484215A (zh) * | 2009-08-24 | 2012-05-30 | E.I.内穆尔杜邦公司 | 有机发光二极管灯具 |
CN103044490A (zh) * | 2012-10-16 | 2013-04-17 | 中科院广州化学有限公司 | 一种新型苯基噌啉类铱配合物及其制备方法与应用 |
CN103044490B (zh) * | 2012-10-16 | 2015-10-28 | 中科院广州化学有限公司 | 一种新型苯基噌啉类铱配合物及其制备方法与应用 |
CN103145763A (zh) * | 2013-03-02 | 2013-06-12 | 大连理工大学 | 新型环金属配体-铂配合物及其制备方法与应用 |
CN103145763B (zh) * | 2013-03-02 | 2016-06-15 | 大连理工大学 | 基于吡啶的环金属配体-铂配合物及其制备方法与应用 |
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CN1520702B (zh) | 2010-05-26 |
EP1466506A4 (en) | 2007-03-07 |
WO2003063555A1 (en) | 2003-07-31 |
JP4299144B2 (ja) | 2009-07-22 |
CA2455844A1 (en) | 2003-07-31 |
EP2306789A1 (en) | 2011-04-06 |
KR100879695B1 (ko) | 2009-01-21 |
EP1466506A1 (en) | 2004-10-13 |
EP2306788A1 (en) | 2011-04-06 |
KR20040069972A (ko) | 2004-08-06 |
JP2005516040A (ja) | 2005-06-02 |
EP2299785A1 (en) | 2011-03-23 |
IL158314A0 (en) | 2004-05-12 |
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