JP4984642B2 - スピロビ(ヘテロフルオレン)誘導体、その用途、及びその製造方法 - Google Patents
スピロビ(ヘテロフルオレン)誘導体、その用途、及びその製造方法 Download PDFInfo
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- JP4984642B2 JP4984642B2 JP2006139464A JP2006139464A JP4984642B2 JP 4984642 B2 JP4984642 B2 JP 4984642B2 JP 2006139464 A JP2006139464 A JP 2006139464A JP 2006139464 A JP2006139464 A JP 2006139464A JP 4984642 B2 JP4984642 B2 JP 4984642B2
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- 238000004519 manufacturing process Methods 0.000 title claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 85
- -1 p- (trifluoromethyl) phenyl group Chemical group 0.000 claims description 67
- 125000004432 carbon atom Chemical group C* 0.000 claims description 43
- 239000002904 solvent Substances 0.000 claims description 42
- 239000004065 semiconductor Substances 0.000 claims description 38
- 230000003647 oxidation Effects 0.000 claims description 31
- 238000007254 oxidation reaction Methods 0.000 claims description 31
- 239000000463 material Substances 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 21
- 239000010409 thin film Substances 0.000 claims description 19
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 9
- 229910000077 silane Inorganic materials 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- USALXEPYWCSANW-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=2[Si]3(C4=CC(=C(C=C4C2C=C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=C(C=C1C=1C=C(C(=CC13)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 Chemical group C1(=CC=CC=C1)C1=CC=2[Si]3(C4=CC(=C(C=C4C2C=C1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC(=C(C=C1C=1C=C(C(=CC13)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 USALXEPYWCSANW-UHFFFAOYSA-N 0.000 claims description 8
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 claims description 6
- 150000004756 silanes Chemical class 0.000 claims description 6
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical group Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 claims description 5
- 150000001983 dialkylethers Chemical class 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- AIFMYMZGQVTROK-UHFFFAOYSA-N silicon tetrabromide Chemical compound Br[Si](Br)(Br)Br AIFMYMZGQVTROK-UHFFFAOYSA-N 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 32
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 238000006243 chemical reaction Methods 0.000 description 29
- 239000000243 solution Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 20
- 238000000576 coating method Methods 0.000 description 18
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 17
- 229910052763 palladium Inorganic materials 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000003153 chemical reaction reagent Substances 0.000 description 15
- 229910052751 metal Inorganic materials 0.000 description 15
- 239000002184 metal Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 238000003786 synthesis reaction Methods 0.000 description 15
- 125000000217 alkyl group Chemical group 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 239000000758 substrate Substances 0.000 description 14
- 238000001819 mass spectrum Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 229910052736 halogen Inorganic materials 0.000 description 12
- 150000002367 halogens Chemical class 0.000 description 12
- 229910052744 lithium Inorganic materials 0.000 description 12
- 239000011777 magnesium Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 239000000376 reactant Substances 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 125000000304 alkynyl group Chemical group 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 239000007789 gas Substances 0.000 description 7
- 238000004817 gas chromatography Methods 0.000 description 7
- 150000002291 germanium compounds Chemical class 0.000 description 7
- 230000035484 reaction time Effects 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 150000003606 tin compounds Chemical class 0.000 description 7
- 239000005749 Copper compound Substances 0.000 description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 150000004703 alkoxides Chemical class 0.000 description 6
- 150000001880 copper compounds Chemical class 0.000 description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000003444 phase transfer catalyst Substances 0.000 description 6
- 229910052718 tin Inorganic materials 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000010949 copper Substances 0.000 description 5
- 229910052802 copper Inorganic materials 0.000 description 5
- 238000005859 coupling reaction Methods 0.000 description 5
- 238000006255 dilithiation reaction Methods 0.000 description 5
- 229910052749 magnesium Inorganic materials 0.000 description 5
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 5
- GGTSNVFGCBCDCG-UHFFFAOYSA-N 1,2-dibromo-4,5-diiodobenzene Chemical compound BrC1=CC(I)=C(I)C=C1Br GGTSNVFGCBCDCG-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 229910052786 argon Inorganic materials 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- ZJHMRPBTRSQNPI-UHFFFAOYSA-N benzo[b][1]benzosilole Chemical compound C1=CC=C2[Si]C3=CC=CC=C3C2=C1 ZJHMRPBTRSQNPI-UHFFFAOYSA-N 0.000 description 4
- UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 description 4
- 229910052796 boron Inorganic materials 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 4
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 238000009815 homocoupling reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
- LVKCSZQWLOVUGB-UHFFFAOYSA-M magnesium;propane;bromide Chemical compound [Mg+2].[Br-].C[CH-]C LVKCSZQWLOVUGB-UHFFFAOYSA-M 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
- 125000005580 triphenylene group Chemical group 0.000 description 4
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- MSBNELVKHUKSPY-UHFFFAOYSA-N 1,2-dibromo-4,5-diphenylbenzene Chemical compound C=1C=CC=CC=1C=1C=C(Br)C(Br)=CC=1C1=CC=CC=C1 MSBNELVKHUKSPY-UHFFFAOYSA-N 0.000 description 3
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 3
- ZQUVDVTYZAXUAL-UHFFFAOYSA-N 2-bromo-3-(3-bromonaphthalen-2-yl)naphthalene Chemical group C1=CC=C2C=C(Br)C(C3=CC4=CC=CC=C4C=C3Br)=CC2=C1 ZQUVDVTYZAXUAL-UHFFFAOYSA-N 0.000 description 3
- XQQBUAPQHNYYRS-UHFFFAOYSA-N 2-methylthiophene Chemical group CC1=CC=CS1 XQQBUAPQHNYYRS-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000006880 cross-coupling reaction Methods 0.000 description 3
- 229940043279 diisopropylamine Drugs 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 230000008014 freezing Effects 0.000 description 3
- 238000007710 freezing Methods 0.000 description 3
- 150000002290 germanium Chemical class 0.000 description 3
- 239000011630 iodine Chemical group 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 238000006138 lithiation reaction Methods 0.000 description 3
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 3
- 229910052759 nickel Inorganic materials 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 150000002941 palladium compounds Chemical class 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 238000005191 phase separation Methods 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 230000009257 reactivity Effects 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 238000000859 sublimation Methods 0.000 description 3
- 230000008022 sublimation Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- 238000010257 thawing Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- XINXXEPJKIRVNV-UHFFFAOYSA-N 1,2-dichloro-N,N,N',N'-tetramethylethane-1,2-diamine Chemical compound ClC(C(N(C)C)Cl)N(C)C XINXXEPJKIRVNV-UHFFFAOYSA-N 0.000 description 2
- OIAQMFOKAXHPNH-UHFFFAOYSA-N 1,2-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 OIAQMFOKAXHPNH-UHFFFAOYSA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 2
- HYTMAANQHXGQMR-UHFFFAOYSA-N 1-bromo-2-(2-bromo-4,5-diphenylphenyl)-4,5-diphenylbenzene Chemical group C=1C=CC=CC=1C=1C=C(C=2C(=CC(=C(C=3C=CC=CC=3)C=2)C=2C=CC=CC=2)Br)C(Br)=CC=1C1=CC=CC=C1 HYTMAANQHXGQMR-UHFFFAOYSA-N 0.000 description 2
- GTILXPRQNNYDHT-UHFFFAOYSA-N 2,3-dibromonaphthalene Chemical compound C1=CC=C2C=C(Br)C(Br)=CC2=C1 GTILXPRQNNYDHT-UHFFFAOYSA-N 0.000 description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- 229920003026 Acene Polymers 0.000 description 2
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 2
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 2
- 238000003747 Grignard reaction Methods 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000006267 biphenyl group Chemical group 0.000 description 2
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- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
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- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- ABTOQLMXBSRXSM-UHFFFAOYSA-N silicon tetrafluoride Chemical compound F[Si](F)(F)F ABTOQLMXBSRXSM-UHFFFAOYSA-N 0.000 description 1
- CFTHARXEQHJSEH-UHFFFAOYSA-N silicon tetraiodide Chemical compound I[Si](I)(I)I CFTHARXEQHJSEH-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PBCFLUZVCVVTBY-UHFFFAOYSA-N tantalum pentoxide Inorganic materials O=[Ta](=O)O[Ta](=O)=O PBCFLUZVCVVTBY-UHFFFAOYSA-N 0.000 description 1
- WXYNMTGBLWPTNQ-UHFFFAOYSA-N tetrabutoxygermane Chemical compound CCCCO[Ge](OCCCC)(OCCCC)OCCCC WXYNMTGBLWPTNQ-UHFFFAOYSA-N 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- GXMNGLIMQIPFEB-UHFFFAOYSA-N tetraethoxygermane Chemical compound CCO[Ge](OCC)(OCC)OCC GXMNGLIMQIPFEB-UHFFFAOYSA-N 0.000 description 1
- ACOVYJCRYLWRLR-UHFFFAOYSA-N tetramethoxygermane Chemical compound CO[Ge](OC)(OC)OC ACOVYJCRYLWRLR-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- LTSUHJWLSNQKIP-UHFFFAOYSA-J tin(iv) bromide Chemical compound Br[Sn](Br)(Br)Br LTSUHJWLSNQKIP-UHFFFAOYSA-J 0.000 description 1
- QPBYLOWPSRZOFX-UHFFFAOYSA-J tin(iv) iodide Chemical compound I[Sn](I)(I)I QPBYLOWPSRZOFX-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
Description
(スピロビ(ヘテロフルオレン)誘導体)
本発明のスピロビ(ヘテロフルオレン)誘導体は、下記一般式(1)で示されるスピロビ(ヘテロフルオレン)誘導体である。
本発明の一般式(1)の置換基について、さらに述べる。
次に、本発明の下記一般式(2)で示されるスピロビ(ヘテロフルオレン)誘導体を含む耐酸化性有機半導体材料について述べる。該耐酸化性有機半導体材料は溶剤への溶解性、耐酸化性に優れ、好適な塗布性を有する。
本発明の一般式(2)の置換基について、さらに述べる。
(有機薄膜)
次に本発明の一般式(2)等で示されるスピロビ(ヘテロフルオレン)誘導体を含む耐酸化性有機半導体材料を用いた有機薄膜について述べる。係る有機薄膜は上記の耐酸化性有機半導体材料溶液の基板への塗布により製造することができる。
(スピロビ(ヘテロフルオレン)誘導体製造方法)
次に、一般式(2)で示されるスピロビ(ヘテロフルオレン)誘導体の製造方法について述べる。なお、一般式(1)で示されるスピロビ(ヘテロフルオレン)誘導体も同様な方法で製造できる。
なお、一般式(1)及び/又は(2)で示されるスピロビ(ヘテロフルオレン)誘導体を以下「一般式(2)等」と標記する。
(ジハロビフェニル誘導体製造方法)
一般式(2)等で表されるスピロビ(ヘテロフルオレン)誘導体の前駆体である一般式(3)で示されるジハロビフェニル誘導体は、下記一般式(4)で示されるジハロベンゼン誘導体から誘導できる。
即ち、一般式(3)で示されるジハロビフェニル誘導体は、一般式(4)で示されるジハロベンゼン誘導体をリチオ化剤又はグリニャール化剤を用いてホモカップリングすることで製造することができる。
一般式(5)の置換基MはMg、B、Zn、Sn又はSiのハロゲン化物、ハイドロオキサイド、アルコキサイド又はアルキル化物であり、上記のパラジウム及び/又はニッケル触媒と反応し、パラジウム及び/又はニッケルと置換できる基である限り特に限定はなく、例えば、MgCl、MgBr、B(OH)2、B(OMe)2、テトラメチルジオキサボロラニル基、ZnCl、ZnBr、ZnI、Sn(Bu−n)3又はSi(Bu−n)3を挙げることができ、好ましくはB(OH)2又はZnClである。
(ジハロベンゼン誘導体製造方法)
一般式(4)で示されるジハロベンゼン誘導体の製造方法について述べる。
なお、置換基X3及びX4は、好ましくはヨウ素原子である。
(ここで、Aは水素原子、フッ素原子、炭素数5〜20のアルキル基、炭素数1〜20のハロゲン化アルキル基、炭素数4〜30のアリール基、炭素数2〜20のアルキニル基、又は炭素数2〜30のアルケニル基を示す。Nは水素原子、Li、Na又はKのアルカリ金属、Mg、B、Zn、Sn又はSiのハロゲン化物、ハイドロオキサイド、アルコキサイド又はアルキル化物を示す。)
なお、一般式(7)のAを選択することにより、一般式(6)で示されるテトラハロベンゼンの置換基X3及びX4に所望の置換基を導入し、所望の置換基を有する一般式(4)で示されるジハロベンゼン誘導体を得ることができる。
装置 島津GC14B
カラム J&Wサイエンティフィック社製、DB−1,30m
ガスクロマトグラフィー−マススペクトル分析
装置 パーキンエルマーオートシステムXL(MS部;ターボマスゴールド)
カラム J&Wサイエンティフィック社製、DB−1,30m
X線回折測定は、以下の条件で行った。
X線 CuKα線(グラファイトモノクロメーター使用)、50kV,200mA
条件 θ−2θスキャン、3≦2θ≦70°、スキャンスピード=4.8°/分、
連続スキャン 0.04°毎計測
反応用の溶媒は市販の脱水溶媒をそのまま用いた。
原料である2,3−ジブロモナフタレンの合成は、ジャーナル オブ オルガニック ケミストリー、1983年、48巻、2364−2366頁に記載されている方法を用いて行った。
MS m/z: 412(M+,26%),332(M+−Br,5),252(M+−2Br,100),126((M+−2Br)/2,54).
実施例1 (テトラベンゾ−9,9’−スピロビ(9−シラフルオレン)の合成)
窒素雰囲気下、100mlシュレンク反応容器に合成例1で合成した3,3’−ジブロモ−2,2’−ビナフチル350mg(0.849mmol)及びジエチルエーテル25mlを加えた。0℃に冷却し、n−ブチルリチウム(関東化学製、1.59M)のヘキサン溶液1.16ml(1.84mmol)を滴下した。0℃で15分間撹拌した後、テトラクロロシラン(和光純薬工業製)72.4mg(0.426mmol)を添加した。一晩かけて室温まで昇温した後、さらに40℃で2時間攪拌した。3N塩酸水溶液及びトルエンを添加し、分相後、有機相をさらに水で洗浄し、無水硫酸ナトリウムで乾燥した。有機相を濾過し、減圧濃縮し、得られた粗固体をさらに60℃で減圧乾燥し、揮発分を除去した。得られた残渣をトルエンから再結晶化し、目的物の黄色結晶を得た(138mg、収率61%)。
得られたテトラベンゾ−9,9’−スピロビ(9−シラフルオレン)の構造式を下記に示す。
窒素雰囲気下、20mlシュレンク容器にo−ジクロロベンゼン3.5gを添加し、凍結(液体窒素)−減圧−窒素置換−融解から成るサイクルを3回繰り返すことで溶存酸素を除去した。そこへ実施例1で得られたテトラベンゾ−9,9’−スピロビ(9−シラフルオレン)の固体6.2mgを添加し、120℃に加熱し溶解させると黄色溶液となった。次にこのシュレンク容器の上部の栓を開け、1時間、外気に接触させることで空気を導入し、さらに120℃で撹拌した。しかし、ガスクロマトグラフィー及びガスクロマトグラフィー−マススペクトル(GCMS)分析で酸化に由来する新たなピークの出現はなかった。従って、実施例1で得られたテトラベンゾ−9,9’−スピロビ(9−シラフルオレン)は耐酸化性を有していることが確認された。
1,2−ジブロモ−4,5−ジヨードベンゼンは「シンレット」、2003年、29−34頁に記載されている方法に従い合成した。
合成例3 (1,2−ジブロモ−4,5−ジフェニルベンゼンの合成)
窒素雰囲気下、200mlシュレンク反応容器に合成例2で合成した1,2−ジブロモ−4,5−ジヨードベンゼン3.074g(6.30mmol)、テトラキス(トリフェニルホスフィン)パラジウム(東京化成工業製)600mg(0.519mmol)、及びフェニルボロン酸(和光純薬工業製)1.920g(15.7mmol)を添加した。さらにトルエン50ml、エタノール13ml、及び炭酸ナトリウム4.007g(37.8mmol)と水16mlからなる水溶液を添加した。82℃に加熱し、24時間撹拌した。室温まで冷却後、トルエン及び水を添加し分相した。有機相を濃縮し、得られた残渣をトルエン26mlに溶解後、70%tert−ブチルハイドロパーオキサイド溶液(和光純薬工業製)1.0mlを添加し、室温で2時間撹拌した。このトルエン溶液を水で2回洗浄後、有機相を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製後(溶媒、ヘキサン)、1,2−ジブロモ−4,5−ジフェニルベンゼンの白色固体を得た(1.953g、収率80%)。
MS m/z: 388(M+,100%),308(M+−Br,23),228(M+−2Br,53).
合成例4 (4,5,4’,5’−テトラフェニル−2,2’−ジブロモ−1,1’−ビフェニルの合成)
窒素雰囲気下、100mlシュレンク反応容器に合成例3で合成した1,2−ジブロモ−4,5−ジフェニルベンゼン1.08g(2.78mmol)及びTHF20mlを添加した。この溶液を−78℃に冷却し、n−ブチルリチウム(関東化学製、1.59M)のヘキサン溶液0.87ml(1.38mmol)を滴下した。一晩かけて室温まで昇温した後、生成した固体を濾過して取り出し、水で洗浄した。この得られた粗固体をトルエンから再結晶化し、目的物の白色固体を得た(722mg、収率84%)。
MS m/z: 616(M+,100%),536(M+−Br,8),456(M+−2Br,38).
実施例3 (2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)の合成)
窒素雰囲気下、100mlシュレンク反応容器に合成例4で合成した4,5,4’,5’−テトラフェニル−2,2’−ジブロモ−1,1’−ビフェニル108mg(0.175 mmol)及びジエチルエーテル5mlを添加した。この溶液を0℃に冷却後、n−ブチルリチウム(関東化学製、1.59M)のヘキサン溶液0.24ml(0.38mmol)を滴下した。0℃で20分間撹拌後、テトラクロロシラン(和光純薬工業製)15.0mg(0.088mmol)を添加し、40℃で4時間攪拌した。3N塩酸水溶液及びトルエンを添加し、分相後、有機相をさらに水で洗浄し、無水硫酸ナトリウムで乾燥した。有機相を濾過し、減圧濃縮し、得られた粗固体をさらに60℃で減圧乾燥し、揮発分を除去した。得られた残渣をトルエン/ヘキサン(=5:1、容積比)から再結晶化し、目的物の白色結晶を得た(48mg、収率58%)。
FABMS m/z: 941(M++1).
得られた目的物の構造式を下記に示す。
窒素雰囲気下、20mlシュレンク容器にo−ジクロロベンゼン2.9gを添加し、凍結(液体窒素)−減圧−窒素置換−融解から成るサイクルを3回繰り返すことで溶存酸素を除去した。そこへ実施例3で得られた2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)の固体5.2mgを添加し、120℃に加熱し溶解させると無色溶液となった。次にこのシュレンク容器の上部の栓を開け、1時間、外気に接触させることで空気を導入し、さらに120℃で撹拌した。しかし、ガスクロマトグラフィー及びガスクロマトグラフィー−マススペクトル(GCMS)分析で酸化に由来する新たなピークの出現はなかった。従って、実施例3で得られた2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)は耐酸化性を有していることが確認された。
窒素雰囲気下、20mlシュレンク容器にo−ジクロロベンゼン2.7gを添加し、凍結(液体窒素)−減圧−窒素置換−融解から成るサイクルを3回繰り返すことで溶存酸素を除去した。そこへペンタセン(東京化成工業製)2.1mgを添加し、120℃に加熱し溶解させると赤紫色溶液となった。次にこのシュレンク容器の上部の栓を開け、1時間、空気を導入すると溶液の色がピンクに変化していた。さらに120℃で撹拌した。ガスクロマトグラフィー及びガスクロマトグラフィー−マススペクトル(GCMS)分析から、6,13−ペンタセンキノンが生成していることがわかった。
窒素雰囲気下、実施例3で得られた2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)9.2mgをトルエン15.5gと混合し、110℃で1時間撹拌し、2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)の溶液を調製した。
Claims (8)
- 2,2’,3,3’,6,6’,7,7’−オクタフェニル−9,9’−スピロビ(9−シラフルオレン)であることを特徴とする請求項1に記載のスピロビ(ヘテロフルオレン)誘導体。
- 請求項3に記載の耐酸化性有機半導体材料を用いた有機薄膜。
- 下記一般式(3)で示されるジハロビフェニル誘導体をジリチオ化及び/又はジグリニャール化した後、シラン化合物と反応させることを特徴とする下記一般式(2)で示されるスピロビ(ヘテロフルオレン)誘導体の製造方法。
- ジアルキルエーテル溶媒中で製造することを特徴とする請求項5に記載の製造方法。
- シラン化合物が、テトラハロゲン化シラン、テトラアルコキシシラン、又はジハロゲン化ジアルコキシシランであることを特徴とする請求項5又は6に記載の製造方法。
- テトラハロゲン化シランがテトラクロロシラン又はテトラブロモシランであることを特徴とする請求項7に記載の製造方法。
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