KR20040069972A - 불소화 페닐피리딘, 페닐피리미딘 및 페닐퀴놀린과이리듐의 전기발광 화합물 및 이 화합물로 제조된 장치 - Google Patents
불소화 페닐피리딘, 페닐피리미딘 및 페닐퀴놀린과이리듐의 전기발광 화합물 및 이 화합물로 제조된 장치 Download PDFInfo
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- KR20040069972A KR20040069972A KR10-2003-7013148A KR20037013148A KR20040069972A KR 20040069972 A KR20040069972 A KR 20040069972A KR 20037013148 A KR20037013148 A KR 20037013148A KR 20040069972 A KR20040069972 A KR 20040069972A
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 99
- 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 32
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical class C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 150000002504 iridium compounds Chemical class 0.000 title description 21
- 150000005359 phenylpyridines Chemical class 0.000 title description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims abstract description 52
- 239000003446 ligand Substances 0.000 claims description 52
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 48
- 229910052801 chlorine Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 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
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 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 8
- 150000002527 isonitriles Chemical class 0.000 claims description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 7
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 6
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 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
- 125000004093 cyano group Chemical group *C#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
- 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 4
- 239000010410 layer Substances 0.000 description 94
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000000203 mixture Substances 0.000 description 44
- 239000000463 material Substances 0.000 description 31
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 229910052741 iridium Inorganic materials 0.000 description 25
- 239000007787 solid Substances 0.000 description 23
- 239000000243 solution Substances 0.000 description 19
- 239000000460 chlorine Substances 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 230000005525 hole transport Effects 0.000 description 14
- 238000000034 method Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- -1 fully hydrogenated Chemical compound 0.000 description 13
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 13
- 229910052751 metal Inorganic materials 0.000 description 12
- 239000002184 metal Substances 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 150000002503 iridium Chemical class 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 125000001424 substituent group Chemical group 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 238000005401 electroluminescence Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000002347 injection Methods 0.000 description 6
- 239000007924 injection Substances 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 229920000728 polyester Polymers 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- 229940093475 2-ethoxyethanol Drugs 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000002244 precipitate Substances 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
- 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
- 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 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 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
- 239000003054 catalyst Substances 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 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 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
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 4
- HXFVJCBIRYKDRY-UHFFFAOYSA-N 1,2-dichloroethane;hexane Chemical class 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 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
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000002619 bicyclic group Chemical group 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000003963 dichloro group Chemical group Cl* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910021645 metal ion Inorganic materials 0.000 description 3
- 238000001465 metallisation Methods 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000005424 photoluminescence Methods 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 230000000171 quenching effect Effects 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000004611 spectroscopical analysis Methods 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
- 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 2
- KGWDRUMNLRKFSV-UHFFFAOYSA-N 2-[4-(trifluoromethoxy)phenyl]-5-(trifluoromethyl)pyridine Chemical compound C1=CC(OC(F)(F)F)=CC=C1C1=CC=C(C(F)(F)F)C=N1 KGWDRUMNLRKFSV-UHFFFAOYSA-N 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical group ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 2
- RTEQSCVHPJOKJG-UHFFFAOYSA-N 5-(trifluoromethyl)-2-[3-(trifluoromethyl)phenyl]pyridine Chemical compound N1=CC(C(F)(F)F)=CC=C1C1=CC=CC(C(F)(F)F)=C1 RTEQSCVHPJOKJG-UHFFFAOYSA-N 0.000 description 2
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical compound C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 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 class [OH-].[Ir+] OFZPMMOCGPTHPA-UHFFFAOYSA-M 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 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
- XZCJVWCMJYNSQO-UHFFFAOYSA-N butyl pbd Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=C(C=2C=CC(=CC=2)C=2C=CC=CC=2)O1 XZCJVWCMJYNSQO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002800 charge carrier Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000008021 deposition 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
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 2
- ODNHQUQWHMGWGT-UHFFFAOYSA-N iridium;oxotin Chemical class [Ir].[Sn]=O ODNHQUQWHMGWGT-UHFFFAOYSA-N 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 238000004776 molecular orbital Methods 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
- 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
- 239000002243 precursor Substances 0.000 description 2
- 239000011241 protective layer Substances 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
- 230000027756 respiratory electron transport chain Effects 0.000 description 2
- KZJPVUDYAMEDRM-UHFFFAOYSA-M silver;2,2,2-trifluoroacetate Chemical compound [Ag+].[O-]C(=O)C(F)(F)F KZJPVUDYAMEDRM-UHFFFAOYSA-M 0.000 description 2
- 239000012265 solid product Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 238000002207 thermal evaporation Methods 0.000 description 2
- 229910052723 transition metal Inorganic materials 0.000 description 2
- 150000003624 transition metals Chemical class 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
- 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
- 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
- GUXDFSIDCAFBCQ-UHFFFAOYSA-N 2-(2,4-dimethoxyphenyl)-5-(trifluoromethyl)pyridine Chemical compound COC1=CC(OC)=CC=C1C1=CC=C(C(F)(F)F)C=N1 GUXDFSIDCAFBCQ-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
- RIKNNBBGYSDYAX-UHFFFAOYSA-N 2-[1-[2-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]-n,n-bis(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 RIKNNBBGYSDYAX-UHFFFAOYSA-N 0.000 description 1
- HHYIUGQFXUVOPD-UHFFFAOYSA-N 2-[3-(trifluoromethyl)phenyl]quinoline Chemical compound FC(F)(F)C1=CC=CC(C=2N=C3C=CC=CC3=CC=2)=C1 HHYIUGQFXUVOPD-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical group ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical group C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- ZVFQEOPUXVPSLB-UHFFFAOYSA-N 3-(4-tert-butylphenyl)-4-phenyl-5-(4-phenylphenyl)-1,2,4-triazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C(N1C=2C=CC=CC=2)=NN=C1C1=CC=C(C=2C=CC=CC=2)C=C1 ZVFQEOPUXVPSLB-UHFFFAOYSA-N 0.000 description 1
- XSKLNXHHATVCSA-UHFFFAOYSA-N 3-chloro-2-(2-fluorophenyl)-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=CC=C1C1=NC=C(C(F)(F)F)C=C1Cl XSKLNXHHATVCSA-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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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
- C07D213/28—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
- C07—ORGANIC CHEMISTRY
- 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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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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Abstract
Description
Claims (11)
- 표 8에 기재된 화합물 8-a 내지 8-s로부터 선택된 화합물.
- 표 8에 기재된 화합물 8-a 내지 8-s로부터 선택된 하나 이상의 화합물을 포함하는 하나 이상의 활성층을 두 개의 전기 접촉층 사이에 포함하는 유기 전기 장치.
- 제2항에 있어서, 활성층이 발광층인 장치.
- 제2항에 있어서, 활성층이 전하 운반층인 장치.
- 570 내지 700 nm의 범위에서 방출 최대치를 갖는 방출층을 포함하며, 방출층의 20 중량% 이상이 하기 화학식 2를 갖는 화합물을 하나 이상 포함하는 것인 유기 전기 장치.<화학식 2>IrLaLbL'yL"z상기 식에서,y는 1이고;z는 0이고;L'는 두자리 리간드이고, 페닐피리딘, 페닐피리미딘 또는 페닐퀴놀린이 아니고;La및 Lb는 서로 같거나 다르며 각각의 La및 Lb는 하기 화학식 XI 및 화학식 XII로부터 선택된 구조를 갖고:<화학식 XI>상기 식에서,R10내지 R19중 하나 이상은 F, CnF2n+1, OCnF2n+1, 및 OCF2X로부터 선택되고, 여기서 n은 1 내지 6의 정수이고, X는 H, Cl 또는 Br이고,<화학식 XII>상기 식에서,R21내지 R30중 하나 이상은 F, CnF2n+1, OCnF2n+1, 및 OCF2X로부터 선택되고,여기서 n은 1 내지 6의 정수이고, X는 H, Cl 또는 Br이다.
- 570 내지 700 nm의 범위에서 방출 최대치를 갖는 방출층을 포함하며, 방출층의 20 중량% 이상이 하기 화학식 3을 갖는 화합물을 하나 이상 포함하는 것인 유기 전기 장치.<화학식 3>IrLaLbLc상기 식에서,La, Lb및 Lc는 서로 같거나 다르고 각각의 La, Lb및 Lc는 하기 화학식 XI 및 화학식 XII로부터 선택되는 구조를 갖고:<화학식 XI>상기 식에서,R10내지 R19중 하나 이상은 F, CnF2n+1, OCnF2n+1, 및 OCF2X로부터 선택되고, 여기서 n은 1 내지 6의 정수이고, X는 H, Cl 또는 Br이고,<화학식 XII>상기 식에서,R21내지 R30중 하나 이상은 F, CnF2n+1, OCnF2n+1, 및 OCF2X로부터 선택되고, 여기서 n은 1 내지 6의 정수이고, X는 H, Cl 또는 Br이다.
- 표 9에 기재된 화합물 9-a 내지 9-l로부터 선택된 화합물.
- 450 내지 500 nm의 범위에서 방출 최대치를 갖는 방출층을 포함하며, 방출층의 20 중량% 이상이 하기 화학식 6을 갖는 화합물을 하나 이상 포함하는 것인 유기 전기 장치.<화학식 6>IrLaLbL'L"상기 식에서,L'는 포스핀, 이소니트릴 및 일산화탄소 중에서 선택되고;L"는 F, Cl, Br 및 I 중에서 선택되고;La및 Lb는 하기 화학식 I의 구조를 갖고,<화학식 I>상기 식에서,R1내지 R8은 알킬, 알콕시, 할로겐, 니트로, 시아노, 플루오로, 불소화 알킬 및 불소화 알콕시기 중에서 독립적으로 선택되고, R1내지 R8중 하나 이상은 F, CnF2n+1, OCnF2n+1, 및 OCF2X로부터 선택되고, 여기서 n은 1 내지 6의 정수이고 X는 H, Cl 또는 Br이고,A는 C이다.
- 제8항에 있어서, L"가 Cl이고, L'가 트리페닐포스핀, 트리스[3,5-비스(트리플루오로메틸)페닐]포스핀, 2,6-디메틸페닐 이소시아니드, 3-트리플루오로메틸페닐 이소시아니드, 및 4-톨루엔설포닐메틸 이소시아니드로부터 선택되는 장치.
- 제8항에 있어서, 화합물이 표 9에 기재된 화합물 9-a 내지 9-l로부터 선택되는 장치.
- 표 12에 기재된 화합물 12-a 내지 12-j로부터 선택된 화합물.
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PCT/US2001/049522 WO2003063555A1 (en) | 2001-12-26 | 2001-12-26 | Electroluminescent iridium compounds wiht fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
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KR1020087021008A Division KR100871275B1 (ko) | 2008-08-27 | 2001-12-26 | 불소화 페닐피리딘과 이리듐의 전기발광 화합물 및 이 화합물로 제조된 장치 |
KR1020087021012A Division KR20080081209A (ko) | 2008-08-27 | 2001-12-26 | 불소화 페닐피리딘 화합물 |
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Publication number | Priority date | Publication date | Assignee | Title |
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US7476452B2 (en) * | 2000-06-30 | 2009-01-13 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridine ligands, and devices made with such compounds |
KR100865096B1 (ko) | 2000-11-30 | 2008-10-24 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
US7166368B2 (en) | 2001-11-07 | 2007-01-23 | E. I. Du Pont De Nemours And Company | Electroluminescent platinum compounds and devices made with such compounds |
US7250512B2 (en) | 2001-11-07 | 2007-07-31 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds having red-orange or red emission and devices made with such compounds |
EP1546237B2 (en) | 2002-09-24 | 2019-04-24 | E. I. du Pont de Nemours and Company | Water dispersible polythiophenes made with polymeric acid colloids |
US7317047B2 (en) | 2002-09-24 | 2008-01-08 | E.I. Du Pont De Nemours And Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
EP1549696A1 (en) | 2002-09-24 | 2005-07-06 | E.I. Du Pont De Nemours And Company | Water dispersible polyanilines made with polymeric acid colloids for electronics applications |
EP2341118A1 (en) | 2002-09-24 | 2011-07-06 | E. I. du Pont de Nemours and Company | Electrically conducting organic polymer/nanoparticle composites and methods for use thereof |
US7816016B1 (en) | 2003-02-13 | 2010-10-19 | E. I. Du Pont De Nemours And Company | Electroluminescent iridium compounds and devices made therefrom |
US7390438B2 (en) | 2003-04-22 | 2008-06-24 | E.I. Du Pont De Nemours And Company | Water dispersible substituted polydioxythiophenes made with fluorinated polymeric sulfonic acid colloids |
KR100718100B1 (ko) * | 2003-09-06 | 2007-05-14 | 삼성에스디아이 주식회사 | 이핵 유기금속 착물 및 이를 이용한 유기 전계 발광 소자 |
KR100560790B1 (ko) | 2003-11-25 | 2006-03-13 | 삼성에스디아이 주식회사 | 고온 특성이 우수한 유기 전계 발광 표시 장치 |
US7351358B2 (en) | 2004-03-17 | 2008-04-01 | E.I. Du Pont De Nemours And Company | Water dispersible polypyrroles made with polymeric acid colloids for electronics applications |
US8147962B2 (en) | 2004-04-13 | 2012-04-03 | E. I. Du Pont De Nemours And Company | Conductive polymer composites |
KR100574450B1 (ko) | 2004-06-03 | 2006-04-26 | 동우 화인켐 주식회사 | 불소계 가지체를 포함하는 유기 전기발광 소자용 발광화합물 |
CN1305883C (zh) * | 2004-06-17 | 2007-03-21 | 复旦大学 | 含芳香胺的铱配合物及其制备方法和应用 |
KR101030011B1 (ko) * | 2004-08-28 | 2011-04-20 | 삼성모바일디스플레이주식회사 | 시클로메탈화 전이금속 착물 및 이를 이용한 유기 전계발광 소자 |
US7449601B2 (en) | 2004-12-16 | 2008-11-11 | E. I. Du Pont De Nemours And Company | Catalysts useful for catalyzing the coupling of arylhalides with arylboronic acids |
US7504769B2 (en) | 2004-12-16 | 2009-03-17 | E. I. Du Pont De Nemours + Company | Aromatic chalcogen compounds and their use |
US8063551B1 (en) | 2004-12-29 | 2011-11-22 | E.I. Du Pont De Nemours And Company | Pixel intensity homogeneity in organic electronic devices |
US8950328B1 (en) | 2004-12-29 | 2015-02-10 | E I Du Pont De Nemours And Company | Methods of fabricating organic electronic devices |
JP5130606B2 (ja) * | 2005-02-25 | 2013-01-30 | コニカミノルタホールディングス株式会社 | 有機エレクトロルミネッセンス素子、その製造方法、表示装置及び照明装置 |
KR100676965B1 (ko) * | 2005-03-05 | 2007-02-02 | 주식회사 두산 | 신규 이리듐 착화합물 및 이를 이용한 유기 전계 발광 소자 |
US7554112B1 (en) | 2005-03-10 | 2009-06-30 | E. I. Du Pont De Nemours And Company | Organic electronic device and processes for forming and using the same |
WO2007002681A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
EP1899993B1 (en) | 2005-06-27 | 2012-06-27 | E.I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
US7727421B2 (en) | 2005-06-27 | 2010-06-01 | E. I. Du Pont De Nemours And Company Dupont Displays Inc | Electrically conductive polymer compositions |
WO2007002682A2 (en) | 2005-06-27 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Electrically conductive polymer compositions |
WO2007002737A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | High work function transparent conductors |
WO2007002740A2 (en) | 2005-06-28 | 2007-01-04 | E. I. Du Pont De Nemours And Company | Buffer compositions |
JP5505382B2 (ja) * | 2005-08-01 | 2014-05-28 | 三菱化学株式会社 | 遷移金属錯体の製造方法 |
US20070170401A1 (en) | 2005-12-28 | 2007-07-26 | Che-Hsiung Hsu | Cationic compositions of electrically conducting polymers doped with fully-fluorinated acid polymers |
US8216680B2 (en) | 2006-02-03 | 2012-07-10 | E I Du Pont De Nemours And Company | Transparent composite conductors having high work function |
US8124172B2 (en) | 2006-03-02 | 2012-02-28 | E.I. Du Pont De Nemours And Company | Process for making contained layers and devices made with same |
US20070278936A1 (en) * | 2006-06-02 | 2007-12-06 | Norman Herron | Red emitter complexes of IR(III) and devices made with such compounds |
JP5061184B2 (ja) | 2006-06-05 | 2012-10-31 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 有機発光ダイオードの形成方法、およびその方法によって製造されたデバイス |
US8057708B2 (en) | 2006-06-30 | 2011-11-15 | E. I. Du Pont De Nemours And Company | Stabilized compositions of conductive polymers and partially fluorinated acid polymers |
US7582757B2 (en) | 2006-09-06 | 2009-09-01 | E. I. Du Pont De Nemours And Company | Electroluminescent complexes of Ir(III) and devices |
KR20090092801A (ko) | 2006-11-13 | 2009-09-01 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 유기 전자 소자 |
US8153029B2 (en) | 2006-12-28 | 2012-04-10 | E.I. Du Pont De Nemours And Company | Laser (230NM) ablatable compositions of electrically conducting polymers made with a perfluoropolymeric acid applications thereof |
US8115378B2 (en) | 2006-12-28 | 2012-02-14 | E. I. Du Pont De Nemours And Company | Tetra-substituted chrysenes for luminescent applications |
US20080191172A1 (en) | 2006-12-29 | 2008-08-14 | Che-Hsiung Hsu | High work-function and high conductivity compositions of electrically conducting polymers |
US20080251768A1 (en) | 2007-04-13 | 2008-10-16 | Che-Hsiung Hsu | Electrically conductive polymer compositions |
US8241526B2 (en) | 2007-05-18 | 2012-08-14 | E I Du Pont De Nemours And Company | Aqueous dispersions of electrically conducting polymers containing high boiling solvent and additives |
EP2147006B1 (en) | 2007-05-18 | 2015-10-28 | Semiconductor Energy Laboratory Co, Ltd. | Organometallic complex, composition and light emitting element including the organometallic complex |
KR101554751B1 (ko) | 2007-06-01 | 2015-09-22 | 이 아이 듀폰 디 네모아 앤드 캄파니 | 녹색 발광 재료 |
EP2150524B1 (en) | 2007-06-01 | 2016-02-10 | E. I. du Pont de Nemours and Company | Chrysenes for deep blue luminescent applications |
CN102603459A (zh) | 2007-06-01 | 2012-07-25 | E.I.内穆尔杜邦公司 | 电荷传输化合物和含该化合物的材料 |
EP2188858A1 (en) * | 2007-10-23 | 2010-05-26 | E. I. du Pont de Nemours and Company | Ternary emissive layers for luminescent applications |
US8309376B2 (en) | 2007-10-26 | 2012-11-13 | E I Du Pont De Nemours And Company | Process and materials for making contained layers and devices made with same |
US8063399B2 (en) | 2007-11-19 | 2011-11-22 | E. I. Du Pont De Nemours And Company | Electroactive materials |
TW200936391A (en) | 2007-12-10 | 2009-09-01 | Du Pont | Multicolor electronic devices and processes of forming the same by printing |
US8040048B2 (en) | 2007-12-12 | 2011-10-18 | Lang Charles D | Process for forming an organic electronic device including an organic device layer |
US8308988B2 (en) | 2007-12-17 | 2012-11-13 | E I Du Pont De Nemours And Company | Electroactive materials |
US8174185B2 (en) | 2007-12-21 | 2012-05-08 | E I Du Pont De Nemours And Company | Charge transport materials for luminescent applications |
KR100966886B1 (ko) * | 2008-01-29 | 2010-06-30 | 다우어드밴스드디스플레이머티리얼 유한회사 | 신규한 유기 발광 화합물 및 이를 발광재료로서 채용하고있는 유기발광소자 |
EP2086034A1 (en) | 2008-02-01 | 2009-08-05 | Nederlandse Centrale Organisatie Voor Toegepast Natuurwetenschappelijk Onderzoek TNO | Electronic device and method of manufacturing thereof |
TW201005813A (en) | 2008-05-15 | 2010-02-01 | Du Pont | Process for forming an electroactive layer |
US8216685B2 (en) | 2008-05-16 | 2012-07-10 | E I Du Pont De Nemours And Company | Buffer bilayers for electronic devices |
US8242487B2 (en) | 2008-05-16 | 2012-08-14 | E I Du Pont De Nemours And Company | Anode for an organic electronic device |
US8343381B1 (en) | 2008-05-16 | 2013-01-01 | E I Du Pont De Nemours And Company | Hole transport composition |
JP5876292B2 (ja) | 2008-05-19 | 2016-03-02 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーE.I.Du Pont De Nemours And Company | 薄層を溶液コーティングするための装置および方法 |
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WO2017122516A1 (ja) | 2016-01-14 | 2017-07-20 | 国立研究開発法人産業技術総合研究所 | シクロメタル化イリジウム錯体の製造方法 |
US11121324B2 (en) | 2016-05-27 | 2021-09-14 | Lg Chem, Ltd. | Dihetero amines in electrically conductive polymer compositions |
US9966542B2 (en) | 2016-06-02 | 2018-05-08 | E I Du Pont De Nemours And Company | Electroactive materials |
Family Cites Families (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH647508A5 (en) * | 1981-05-07 | 1985-01-31 | Lonza Ag | Process for the preparation of 2-arylpyridines |
GB8909011D0 (en) | 1989-04-20 | 1989-06-07 | Friend Richard H | Electroluminescent devices |
DE69110922T2 (de) | 1990-02-23 | 1995-12-07 | Sumitomo Chemical Co | Organisch elektrolumineszente Vorrichtung. |
US5408109A (en) | 1991-02-27 | 1995-04-18 | The Regents Of The University Of California | Visible light emitting diodes fabricated from soluble semiconducting polymers |
US5552678A (en) | 1994-09-23 | 1996-09-03 | Eastman Kodak Company | AC drive scheme for organic led |
JP3691101B2 (ja) * | 1995-01-24 | 2005-08-31 | 三洋電機株式会社 | 有機エレクトロルミネッセンス素子 |
US5627193A (en) * | 1995-02-09 | 1997-05-06 | Mitsui Toatsu Chemicals, Inc. | Quinoline-4-carbonylguanidine derivatives, process for producing the same and pharmaceutical preparations containing the compounds |
JP3929690B2 (ja) * | 1999-12-27 | 2007-06-13 | 富士フイルム株式会社 | オルトメタル化イリジウム錯体からなる発光素子材料、発光素子および新規イリジウム錯体 |
US6821645B2 (en) * | 1999-12-27 | 2004-11-23 | Fuji Photo Film Co., Ltd. | Light-emitting material comprising orthometalated iridium complex, light-emitting device, high efficiency red light-emitting device, and novel iridium complex |
JP4048521B2 (ja) * | 2000-05-02 | 2008-02-20 | 富士フイルム株式会社 | 発光素子 |
US20020121638A1 (en) * | 2000-06-30 | 2002-09-05 | Vladimir Grushin | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
JP4712232B2 (ja) * | 2000-07-17 | 2011-06-29 | 富士フイルム株式会社 | 発光素子及びアゾール化合物 |
ATE482476T1 (de) * | 2000-07-17 | 2010-10-15 | Fujifilm Corp | Lichtemittierendes element und azolverbindung |
CN101924190B (zh) * | 2000-08-11 | 2012-07-04 | 普林斯顿大学理事会 | 有机金属化合物和发射转换有机电致磷光 |
JP4154138B2 (ja) * | 2000-09-26 | 2008-09-24 | キヤノン株式会社 | 発光素子、表示装置及び金属配位化合物 |
KR100865096B1 (ko) * | 2000-11-30 | 2008-10-24 | 캐논 가부시끼가이샤 | 발광 소자 및 표시 장치 |
WO2002066462A1 (en) * | 2001-02-02 | 2002-08-29 | Glaxo Group Limited | Pyrazole derivatives against tgf overexpression |
WO2002104080A1 (fr) * | 2001-06-15 | 2002-12-27 | Canon Kabushiki Kaisha | Dispositif a electroluminescence organique |
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CA2455844A1 (en) | 2003-07-31 |
JP2005516040A (ja) | 2005-06-02 |
WO2003063555A1 (en) | 2003-07-31 |
EP1466506A4 (en) | 2007-03-07 |
KR100879695B1 (ko) | 2009-01-21 |
EP2306789A1 (en) | 2011-04-06 |
CN1520702A (zh) | 2004-08-11 |
EP2306788A1 (en) | 2011-04-06 |
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