JP2012176981A - フッ素化フェニルピリジン、フェニルピリミジン及びフェニルキノリンを伴うエレクトロルミネセントイリジウム化合物及びかかる化合物で作られたデバイス - Google Patents
フッ素化フェニルピリジン、フェニルピリミジン及びフェニルキノリンを伴うエレクトロルミネセントイリジウム化合物及びかかる化合物で作られたデバイス Download PDFInfo
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- JP2012176981A JP2012176981A JP2012130171A JP2012130171A JP2012176981A JP 2012176981 A JP2012176981 A JP 2012176981A JP 2012130171 A JP2012130171 A JP 2012130171A JP 2012130171 A JP2012130171 A JP 2012130171A JP 2012176981 A JP2012176981 A JP 2012176981A
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- compound
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- iridium
- complex
- compounds
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 69
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 title abstract description 19
- OXPDQFOKSZYEMJ-UHFFFAOYSA-N 2-phenylpyrimidine Chemical compound C1=CC=CC=C1C1=NC=CC=N1 OXPDQFOKSZYEMJ-UHFFFAOYSA-N 0.000 title abstract description 12
- 150000002504 iridium compounds Chemical class 0.000 title description 15
- 150000005359 phenylpyridines Chemical class 0.000 title description 2
- 150000005360 2-phenylpyridines Chemical class 0.000 abstract description 4
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical class [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 abstract 3
- 239000010410 layer Substances 0.000 description 86
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000000203 mixture Substances 0.000 description 30
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000000463 material Substances 0.000 description 29
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 28
- 239000000126 substance Substances 0.000 description 28
- 229910052741 iridium Inorganic materials 0.000 description 27
- 239000003446 ligand Substances 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 23
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 239000000377 silicon dioxide Substances 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000000758 substrate Substances 0.000 description 10
- 150000002503 iridium Chemical class 0.000 description 9
- 239000000284 extract Substances 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 7
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000005401 electroluminescence Methods 0.000 description 6
- 150000002739 metals Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000000539 dimer Substances 0.000 description 5
- 230000001815 facial effect Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- -1 nitrate ions Chemical class 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229920001940 conductive polymer Polymers 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 238000010791 quenching 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
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000002800 charge carrier Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000000151 deposition Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 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 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 238000010992 reflux Methods 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
- 238000004467 single crystal X-ray diffraction Methods 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000002207 thermal evaporation Methods 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 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
- 125000004429 atom Chemical group 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
- 230000015572 biosynthetic process Effects 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
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000003054 catalyst 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
- 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
- 238000000921 elemental analysis Methods 0.000 description 2
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000004770 highest occupied molecular orbital Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 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
- 238000005259 measurement Methods 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 229910021645 metal ion Inorganic materials 0.000 description 2
- 229910003455 mixed metal oxide Inorganic materials 0.000 description 2
- 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 2
- 230000007935 neutral effect Effects 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 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
- 229920000548 poly(silane) polymer Polymers 0.000 description 2
- 229920000767 polyaniline Polymers 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000000171 quenching effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- 230000007704 transition Effects 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
- SJQBHNHASPQACB-ONEGZZNKSA-N (e)-1,2-dimethoxyethene Chemical group CO\C=C\OC SJQBHNHASPQACB-ONEGZZNKSA-N 0.000 description 1
- 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 1
- 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 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
- UJJMLGJZQGGQAZ-UHFFFAOYSA-N 2-(fluoromethyl)pyridine Chemical compound FCC1=CC=CC=N1 UJJMLGJZQGGQAZ-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
- 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 1
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical class ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 1
- JWFZJKPLLNMPKZ-UHFFFAOYSA-N 2-chloropyridine;quinoline Chemical class ClC1=CC=CC=N1.N1=CC=CC2=CC=CC=C21 JWFZJKPLLNMPKZ-UHFFFAOYSA-N 0.000 description 1
- UNCQVRBWJWWJBF-UHFFFAOYSA-N 2-chloropyrimidine Chemical class ClC1=NC=CC=N1 UNCQVRBWJWWJBF-UHFFFAOYSA-N 0.000 description 1
- OFUFXTHGZWIDDB-UHFFFAOYSA-N 2-chloroquinoline Chemical class C1=CC=CC2=NC(Cl)=CC=C21 OFUFXTHGZWIDDB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 229940093475 2-ethoxyethanol Drugs 0.000 description 1
- LIPRUDRQZVPYCL-UHFFFAOYSA-N 2-prop-2-enylpyridine Chemical compound C=CCC1=CC=CC=N1 LIPRUDRQZVPYCL-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
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
- OGGKVJMNFFSDEV-UHFFFAOYSA-N 3-methyl-n-[4-[4-(n-(3-methylphenyl)anilino)phenyl]phenyl]-n-phenylaniline Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 OGGKVJMNFFSDEV-UHFFFAOYSA-N 0.000 description 1
- YGBCLRRWZQSURU-UHFFFAOYSA-N 4-[(diphenylhydrazinylidene)methyl]-n,n-diethylaniline Chemical compound C1=CC(N(CC)CC)=CC=C1C=NN(C=1C=CC=CC=1)C1=CC=CC=C1 YGBCLRRWZQSURU-UHFFFAOYSA-N 0.000 description 1
- 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 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
- MVIXNQZIMMIGEL-UHFFFAOYSA-N 4-methyl-n-[4-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 MVIXNQZIMMIGEL-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 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 1
- YDCKPVSNPLMYRB-UHFFFAOYSA-N 5-bromo-2-(4-bromophenyl)pyridine Chemical compound C1=CC(Br)=CC=C1C1=CC=C(Br)C=N1 YDCKPVSNPLMYRB-UHFFFAOYSA-N 0.000 description 1
- UHBIKXOBLZWFKM-UHFFFAOYSA-N 8-hydroxy-2-quinolinecarboxylic acid Chemical class C1=CC=C(O)C2=NC(C(=O)O)=CC=C21 UHBIKXOBLZWFKM-UHFFFAOYSA-N 0.000 description 1
- SFBHJDZYFDQEEY-UHFFFAOYSA-N 9-cyclobutylcarbazole Chemical compound C1CCC1N1C2=CC=CC=C2C2=CC=CC=C21 SFBHJDZYFDQEEY-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 0 CC1=NC=C(*)CC=C1 Chemical compound CC1=NC=C(*)CC=C1 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 229910052772 Samarium Inorganic materials 0.000 description 1
- 238000000944 Soxhlet extraction Methods 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 229910052768 actinide Inorganic materials 0.000 description 1
- 150000001255 actinides Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
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- 239000004411 aluminium Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000010406 cathode material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- 229920000547 conjugated polymer Polymers 0.000 description 1
- 150000001893 coumarin derivatives Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 150000002472 indium compounds Chemical class 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Inorganic materials [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- JGOAZQAXRONCCI-SDNWHVSQSA-N n-[(e)-benzylideneamino]aniline Chemical compound C=1C=CC=CC=1N\N=C\C1=CC=CC=C1 JGOAZQAXRONCCI-SDNWHVSQSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000005824 oxyalkoxy group Chemical group 0.000 description 1
- CBHCDHNUZWWAPP-UHFFFAOYSA-N pecazine Chemical compound C1N(C)CCCC1CN1C2=CC=CC=C2SC2=CC=CC=C21 CBHCDHNUZWWAPP-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical class OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- QGLVEAGMVUQOJP-UHFFFAOYSA-N prop-2-enylboronic acid Chemical compound OB(O)CC=C QGLVEAGMVUQOJP-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 229910052761 rare earth metal Inorganic materials 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 238000002230 thermal chemical vapour deposition Methods 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 238000000427 thin-film deposition Methods 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
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Abstract
【解決手段】本発明は一般に、エレクトロルミネセントIr(III)化合物、Ir(III)化合物を作るために使用される置換2−フェニルピリジン、フェニルピリミジン及びフェニルキノリン、ならびにIr(III)化合物で作られるデバイスに向けられている。
【選択図】図1
Description
IrLaLbLc xL’yL’’z (第1化学式)
なお式中、
x=0又はy+z=0であり、y=2であるときz=0であることを条件として、x=0又は1、y=0、1又は2、及びz=0又は1であり;
L’が単座配位子であるときy+z=2であり、L’が二座配位子であるときz=0であることを条件として、L’=二座配位子又は単座配位子でありかつフェニルピリジン、フェニルピリミジン又はフェニルキノリンではなく;
L’’は、単座配位子であり、かつフェニルピリジン及びフェニルピリミジン又はフェニルキノリンではなく;
La、Lb及びLcは互いに同様であるか又は異なり、La、Lb及びLcの各々は
R1−R4及びR5−R8の隣接対を接合させて5員環又は6員環を形成することができ、
R1−R8の少なくとも1つはF、CnF2n+1、OCnF2n+1及びOCF2Xから選択され、式中、n=1−6、X=H、Cl又はBrであり、
A=NであるときR1は存在しないことを条件として、A=C又はNである。
IrLaLbL’yL’’z(第2化学式)
(なお式中、y、z、La、Lb、L’及びL’’は、上述の第1化学式で定義された通りである。
IrLaLbLc (第3化学式)
なお式中、
La、Lb及びLcは、上述の第1化学式に定義された通りである。
Fac−Ir(La)3 (第4化学式)
(式中、Laは、上述の構造(I)を有する)。
mer−Ir(La)3 (第5化学式)
(式中、Laは上述の構造(I)を有する)。
イリジウム二量体は一般に、まず最初に、2−フェニルピリジン、フェニルピリミジン又はフェニルキノリンと3塩化イリジウム水和物を反応させ、NaOBを添加することによって調製可能である。
本発明は同様に、その少なくとも1つの層が本発明のイリジウム錯体を内含する、2つの電気接点層の間に位置づけされた少なくとも1つの光活性層を含む電子デバイスにも関する。デバイスは、付加的なホール輸送及び電子輸送層を有することが多い。標準的構造は図1に示されている。デバイス100は、陽極層110及び陰極層150を有する。陽極に隣接しているのは、ホール輸送材料を含む層120である。陰極に隣接しているのは、電子輸送材料を含む層140である。ホール輸送層と電子輸送層の間には、光活性層130がある。
この実施例は、イリジウム化合物を形成するために使用される2−フェニルピリジン及び2−フェニルピリミジンの調製を例示している。
この実施例は、上述の第4化学式fac−Ir(La)3のイリジウム化合物の調製について例示している。
温度をゆっくりと(30分)185℃(油浴)まで上昇させながら、IrCl3・nH2O(54%Ir:508mg)、2−(4−フルオロフェニル)−5−トリフルオロメチルピリジン、化合物kk(2.20g)、AgOCOCF3(1.01g)及び水(1mL)の混合物をN2流の下で勢いよくかき混ぜた。185〜190℃で2時間後に、混合物は凝固した。混合物を室温まで冷却した。固体を、抽出物が脱色するまでジクロロメタンで抽出した。短かいシリカカラムを通して組合さったジクロロメタン溶液を濾過し蒸発させた。メタノール(50mL)を残渣に添加し、フラスコを−10℃に保ち一晩放置した。トリス−シクロメタレート化錯体の黄色沈殿物、化合物bを分離し、メタノールで洗浄し、真空下で乾燥させた。収量:1.07g(82%)。1,2−ジクロロエメタン中のその温かい溶液をゆっくり冷却することで錯体のX線品質の結晶を得た。
温度をゆっくりと(15分)192℃(油浴)まで上昇させながら、IrCl3・nH2O(54%Ir:504mg)、2−(3−トリフルオロメチルフェニル)−5−トリフルオロメチルピリジン、化合物bb(1.60g)及びAgOCOCF3(1.01g)の混合物をN2流の下で勢いよくかき混ぜた。190〜195℃で6時間後に、混合物は凝固した。混合物を室温まで冷却した。固体を、シリカカラム上に置き、これを、次に大量のジクロロメタンで洗浄した。濾過物の蒸発後の残渣をメタノールで処理して、黄色固体を生成した。固体を収集し、25−mLのマイクロ−ソックスレー抽出装置内でジクロロメタンでの抽出により精製した。トリス−シクロメタレート化 錯体の黄色沈殿物、化合物eを分離し、メタノールで洗浄し、真空下で乾燥させた。収量:0.59g(39%)。高温の1,2−ジクロロエタンから錯体のX線品質の結晶が得られた。
190〜195℃(油浴)で6時間15分の間、IrCl3・nH2O(54%Ir:508mg)、2−(2−フルオロフェニル)−5−トリフルオロメチルピリジン、化合物aa(1.53g)及びAgOCOCF3(1.01g)の混合物をN2流の下で勢いよくかき混ぜた。混合物を室温まで冷却し、次に、高温1,2−ジクロロエタンで抽出した。抽出物を短かいシリカカラムを通して濾過し、蒸発させた。メタノール(20mL)での残渣の処理は、望ましい生成物、化合物dの沈殿を結果としてもたらし、これを濾過により分離し、メタノールで洗浄し、真空下で乾燥させた。収量:0.63g(49%)。ジクロロメタン/メタノールから錯体のX線品質の結晶を得た。
190〜195℃(油浴)で2時間45分の間、IrCl3・nH2O(54%Ir:503mg)、2−(4−トリフルオロメトキシフェニル)−5−トリフルオロメチルピリジン、化合物ee(2.00g)及びAgOCOCF3(1.10g)の混合物をN2流の下で勢いよくかき混ぜた。混合物を室温まで冷却し、次に、ジクロロメタンで抽出した。抽出物を短かいシリカカラムを通して濾過し、蒸発させた。メタノール(20mL)での残渣の処理は、望ましい生成物、化合物iの沈殿を結果としてもたらし、これを濾過により分離し、メタノールで洗浄し、真空下で乾燥させた。収量は0.86gであった。さらに、母液を蒸発させ、残渣に石油エーテルを添加することにより0.27gの錯体を得た。全体的収量:1.13g(72%)。
温度をゆっくりと(30分)185℃(油浴)まで上昇させながら、IrCl3・nH2O(54%Ir:530mg)、2−(3−メトキシフェニル)−5−トリフルオロスメチルピリジン(2.50g)、AgOCOCF3(1.12g)及び水(1mL)の混合物をN2流の下で勢いよくかき混ぜた。185℃で1時間後に、混合物は凝固した。混合物を室温まで冷却した。固体を、抽出物が脱色するまでジクロロメタンで抽出した。短かいシリカカラムを通して組合さったジクロロメタン溶液を濾過し蒸発させた。残渣をヘキサンで洗浄し、次に1,2ジクロロエタン−ヘキサンから再結晶させた。収量:0.30g。19F NMR(CD2Cl2、20℃)、δ:−63(s)、1H NMR(CD2Cl2、20℃)、δ:8.1(1H)、7.9(1H)、7.8(1H)、7.4(1H)、6.6(2H)、4.8(3H)。1,2−ジクロロエタン−ヘキサンから、錯体(1,2−ジクロロエタン、ヘキサン溶媒和物)のX線品質の結晶を得た。このフェーシャル錯体は、オレンジ色光ルミネセントであった。
この実施例は、上述の第2化学式 IrLaLbLc xL’yL’’zのイリジウム錯体の調製を例示するものである。
4時間190−195℃で、IrCl3・nH2O(54%Ir:510mg)、2−(3−トリフルオロメチルフェニル)−キノリン(1.80g)及びトリフルオロ酢酸銀(1.10g)の混合物を勢いよくかき混ぜた。結果として得た固体をジクロロメタンでシリカ上クロマトグラフィに付し、ジシクロメタレート化錯体と未反応配位子の混合物を生成した。温かいヘキサンでの抽出により、混合物から未反応配位子を除去した。抽出物が無色となった後、ヘキサン不溶性固体を収集し真空下で乾燥した。収量は、0.29gであった。19F NMR:−63.5(s.6F)、−76.5(s.3F)。この錯体の構造を、単結晶X線回折研究により立証した。
1.5時間190℃で、IrCl3・nH2O(54%Ir:500mg)、2−(2−フルオロフェニル)−3−クロロ−5−トリフルオロメチルピリジン(2.22g)、水(0.3mL)及びトリフルオロ酢酸銀(1.00g)の混合物を1.5時間190℃で撹拌した。固体生成物を、ジクロロメタンでシリカ上クロマトグラフィに付して、ジシクロメタレート化アクアトリフルオロアセタト錯体、化合物l−p及び未反応配位子の2:1の同時結晶化アダクツ0.33gを生成した。19F NMR:−63.0(9F)、−76.5(3F)、−87.7(2F)、−114.4(1F)。ジクロロメタン−ヘキサンから再結晶化により、同時結晶化されたフェニルピリジン配位子を除去した。アダクツと錯体の構造を単結晶X線回折研究により立証した。
この実施例は、上述の構造(VIII)を有するヒドロキソイリジウム二量体の調製を例示している。
この実施例は、イリジウム二量体からのビス−シクロメタレート化錯体の調製を例示している。
実施例4からのイリジウムヒドロキソ二量体(100mg)アセト酢酸エチル(0.075mL;4倍余剰)及びジクロロメタン(4mL)の混合物を室温で一晩撹拌した。溶液を短かいシリカプラグを通して濾過し、蒸発させてオレンジ−黄色固体を得、これをヘキサンで洗浄して乾燥させた。錯体の収量は109mg(94%)であった。1H NMR(CD2Cl2):1.1(t、CH3)、3.9(dm、CH2)、4.8(s、CH3COCH)、5.9(m)、6.7(m)、7.7(m)、8.0(m)、8.8(d).19F NMR(CD2Cl2):−63.1(s、3F)、−63.2(s、3F)、−109.1(ddd、1F)、−109.5(ddd).分析:計算値:C、44.9;H、2.6;N、3.5.実際値C、44.4;H、2.6;N、3.3.
実施例4(0.20g)からのヒドロキソイリジウム二量体のTHF(6mL)溶液を、50mgのトリフルオロ酢酸で処理し、短かいシリカプラグを通して濾過し、計算上0.5mLまで蒸発させ、ヘキサン(8mL)で処理し、一晩放置した。黄色結晶固体を分離し、ヘキサンで洗浄し、真空下で乾燥させた。収量(1:1THF溶媒和物):0.24g(96%)。19F NMR(CD2Cl2、20℃)、δ:−63.2(s、3F)、−76.4(s、3F)、−107.3(ddd、1F).1H NMR(CD2Cl2、20℃)、δ:9.2(br s、1H)、8.2(dd、1H)、8.1(d、1H)、7.7(m、1H)、6.7(m、1H)、5.8(dd、1H)、3.7(m、2H、THF)、1.8(m、2H、THF).
トリフルオロ酢酸中間物、化合物1−w(75mg)及び2−(4−ブロモフェニル)−5−ブロモピリジン(130mg)をN2下で150〜155℃で30分間撹拌した。結果として得られた固体を室温まで冷却し、CH2Cl2中で溶解させた。結果として得た溶液をシリカゲルを通して濾過し蒸発させた。残渣を数回温かいヘキサンで洗浄し、真空下で乾燥させて、黄色、黄色光ルミネセントの固体を残した。収量:74mg(86%)。19F NMR(CD2Cl2、20℃)、δ:−63.1(s、3F)、−63.3(s、3F)、−108.8(ddd、1F)、−109.1(ddd、1F).1H NMR(CD2Cl2、20℃)、δ:8.2(s)、7.9(m)、7.7(m)、7.0(d)、6.7(m)、6.2(dd)、6.0(dd).錯体は、メリディオナル錯体であり、フッ素化配位子の窒素は、X線分析によって確認された通りトランスであった。
この実施例は、上述の第5化学式mer−Ir(La)3のイリジウム化合物の調製を例示するものである。
この錯体は、化合物1−nと類似の要領で合成された。NMR、TLC及びTGAデータによると、結果は、フェイシャル及びメリディオナル異性体のほぼ1:1の混合物であった。
温度をゆっくりと(30〜40分)165℃(油浴)まで上昇させながら、IrCl3・nH2O(54% Ir:0.40g)、2−(3,5−ジクロロフェニル)−5−トリフルオロメチルピリジン(1.40g)、AgOCOCF3(0.81g)及び水(0.5mL)の混合物をN2流の下で勢いよくかき混ぜた。165℃で40分後に、混合物は凝固した。混合物を室温まで冷却した。固体を、抽出物が脱色するまでジクロロメタンで抽出した。短かいシリカカラムを通して組合さったジクロロメタン溶液を濾過し蒸発させた。残渣をヘキサンで徹底的に洗浄し、真空下で乾燥させた。収量:0.53g(49%)。19F NMR(CD2Cl2、20℃)、δ:−63.55(s、3F)、−63.57(s、3F)、−63.67(s、3F)、−89.1(t、1F)、−100.6(t、1F)、102.8(dd、1F)、−118.6(ddd、1F)、−119.3(ddd、1F)、−123.3(ddd、1F).1H NMR(CD2Cl2、20℃)、δ:8.4(s)、8.1(m)、7.9(m)、7.6(s)、7.5(m)、6.6(m)、6.4(m).錯体は、X線分析によっても確認された通り、メリディオナル錯体であった。
この錯体を、化合物1−qと類似の形で調製及び単離させ、次に1,2ジクロロエタン−ヘキサンから結晶化により精製した。精製された生成物は53%であった。錯体は、NMRデータから以下の通りmerである。19F NMR(CD2Cl2、20℃)、δ:−63.48(s、3F)、−63.52(s、6F)、−105.5(ddd、1F)、−105.9(ddd、1F)、−106.1(ddd、1F)、−107.4(t、1F)、−107.9(t、1F)、−109.3(t、1F).1H NMR(CD2Cl2、20℃)、δ:8.6(m)、8.3(s)、8.2(s)、8.1(m)、7.9(m)、7.6(m)、6.6(m)、6.4(m)、6.0(m)、5.8(m).
このmer−錯体を、トリフルオロアセテートジシクロメタレート化中間体、化合物1−x及び2−(4−フルオロフェニル)−5−トリフルオロメチルピリジンを用いて、化合物1−wと類似の要領で調製した。19F NMR(CD2Cl2、20℃)、δ:−63.30(s、3F)、−63.34(s、3F)、−63.37(s、3F)、−108.9(ddd、1F)、−109.0(ddd、1F)、−109.7(ddd、1F).1H NMR(CD2Cl2、20℃)、δ:8.3−7.6(m)、6.7(m)、6.6(dd)、6.3(dd)、6.0(dd)。この黄色−ルミネセントメリディオナル錯体は、1気圧での昇華の時点で、緑色ルミネセントフェイシャル異性体つまり化合物1−bへと異性体化した。
この実施例は、本発明のイリジウム錯体を用いたOLEDの形成を例示している。
110 陽極層
120 ホール輸送材料を含む層
130 光活性層
140 電子輸送材料を含む層
150 陰極層
200 器具
210 ルミネセンス計
230 レンズ
240 電子シャッタ
250 スペクトログラフ
260 ダイオードアレイ検出器
270 コンピュータ
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EXPY | Cancellation because of completion of term |