JP4912364B2 - 可溶性セクシチオフェン誘導体を含む組成物 - Google Patents
可溶性セクシチオフェン誘導体を含む組成物 Download PDFInfo
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- JP4912364B2 JP4912364B2 JP2008189903A JP2008189903A JP4912364B2 JP 4912364 B2 JP4912364 B2 JP 4912364B2 JP 2008189903 A JP2008189903 A JP 2008189903A JP 2008189903 A JP2008189903 A JP 2008189903A JP 4912364 B2 JP4912364 B2 JP 4912364B2
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- solution
- sexithiophene
- added
- organic
- diethyl
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims description 15
- 230000001568 sexual effect Effects 0.000 title claims description 10
- 150000003577 thiophenes Chemical class 0.000 title description 5
- 239000003960 organic solvent Substances 0.000 claims description 8
- 239000000243 solution Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 19
- KUJYDIFFRDAYDH-UHFFFAOYSA-N 2-thiophen-2-yl-5-[5-[5-(5-thiophen-2-ylthiophen-2-yl)thiophen-2-yl]thiophen-2-yl]thiophene Chemical class C1=CSC(C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC(=CC=2)C=2SC=CC=2)=C1 KUJYDIFFRDAYDH-UHFFFAOYSA-N 0.000 description 16
- 239000004065 semiconductor Substances 0.000 description 15
- 125000000524 functional group Chemical group 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- KXSFECAJUBPPFE-UHFFFAOYSA-N 2,2':5',2''-terthiophene Chemical class C1=CSC(C=2SC(=CC=2)C=2SC=CC=2)=C1 KXSFECAJUBPPFE-UHFFFAOYSA-N 0.000 description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 12
- 230000005669 field effect Effects 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 10
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 229910021417 amorphous silicon Inorganic materials 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- UOKRBSXOBUKDGE-UHFFFAOYSA-N butylphosphonic acid Chemical compound CCCCP(O)(O)=O UOKRBSXOBUKDGE-UHFFFAOYSA-N 0.000 description 7
- 239000011368 organic material Substances 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- -1 lithium aluminum hydride Chemical compound 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- UUIQMZJEGPQKFD-UHFFFAOYSA-N n-butyric acid methyl ester Natural products CCCC(=O)OC UUIQMZJEGPQKFD-UHFFFAOYSA-N 0.000 description 6
- 239000010409 thin film Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000031709 bromination Effects 0.000 description 5
- 238000005893 bromination reaction Methods 0.000 description 5
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 229930192474 thiophene Natural products 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- JGFBQFKZKSSODQ-UHFFFAOYSA-N Isothiocyanatocyclopropane Chemical compound S=C=NC1CC1 JGFBQFKZKSSODQ-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001733 carboxylic acid esters Chemical class 0.000 description 4
- 239000012230 colorless oil Substances 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000008878 coupling Effects 0.000 description 4
- 238000010168 coupling process Methods 0.000 description 4
- 238000005859 coupling reaction Methods 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- HEWZVZIVELJPQZ-UHFFFAOYSA-N 2,2-dimethoxypropane Chemical compound COC(C)(C)OC HEWZVZIVELJPQZ-UHFFFAOYSA-N 0.000 description 3
- GHTCEOPJYODOQF-UHFFFAOYSA-N 2-(4-bromobutyl)thiophene Chemical compound BrCCCCC1=CC=CS1 GHTCEOPJYODOQF-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical group OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 239000008186 active pharmaceutical agent Substances 0.000 description 3
- 150000001408 amides Chemical group 0.000 description 3
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- 238000006243 chemical reaction Methods 0.000 description 3
- 229910021419 crystalline silicon Inorganic materials 0.000 description 3
- 238000003618 dip coating Methods 0.000 description 3
- 230000026045 iodination Effects 0.000 description 3
- 238000006192 iodination reaction Methods 0.000 description 3
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 3
- 239000004033 plastic Substances 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- VIMMECPCYZXUCI-MIMFYIINSA-N (4s,6r)-6-[(1e)-4,4-bis(4-fluorophenyl)-3-(1-methyltetrazol-5-yl)buta-1,3-dienyl]-4-hydroxyoxan-2-one Chemical compound CN1N=NN=C1C(\C=C\[C@@H]1OC(=O)C[C@@H](O)C1)=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 VIMMECPCYZXUCI-MIMFYIINSA-N 0.000 description 2
- IGVKWAAPMVVTFX-BUHFOSPRSA-N (e)-octadec-5-en-7,9-diynoic acid Chemical compound CCCCCCCCC#CC#C\C=C\CCCC(O)=O IGVKWAAPMVVTFX-BUHFOSPRSA-N 0.000 description 2
- OHZAHWOAMVVGEL-UHFFFAOYSA-N 2,2'-bithiophene Chemical compound C1=CSC(C=2SC=CC=2)=C1 OHZAHWOAMVVGEL-UHFFFAOYSA-N 0.000 description 2
- WPLJSNYMHYZSHG-UHFFFAOYSA-N 2-(4-diethoxyphosphorylbutyl)thiophene Chemical compound CCOP(=O)(OCC)CCCCC1=CC=CS1 WPLJSNYMHYZSHG-UHFFFAOYSA-N 0.000 description 2
- UZQDKBMPXQPOHL-UHFFFAOYSA-N 2-bromo-3-(4-diethoxyphosphorylbutyl)thiophene Chemical compound CCOP(=O)(OCC)CCCCC=1C=CSC=1Br UZQDKBMPXQPOHL-UHFFFAOYSA-N 0.000 description 2
- VYTXLSQVYGNWLV-UHFFFAOYSA-N 4-(2-thienyl)butyric acid Chemical compound OC(=O)CCCC1=CC=CS1 VYTXLSQVYGNWLV-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 238000006619 Stille reaction Methods 0.000 description 2
- 150000001412 amines Chemical group 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 229910000024 caesium carbonate Inorganic materials 0.000 description 2
- 150000001735 carboxylic acids Chemical group 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- BRMYZIKAHFEUFJ-UHFFFAOYSA-L mercury diacetate Chemical compound CC(=O)O[Hg]OC(C)=O BRMYZIKAHFEUFJ-UHFFFAOYSA-L 0.000 description 2
- 238000000813 microcontact printing Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
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- 239000010703 silicon Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 2
- 238000001771 vacuum deposition Methods 0.000 description 2
- KAFZOLYKKCWUBI-HPMAGDRPSA-N (2s)-2-[[(2s)-2-[[(2s)-1-[(2s)-3-amino-2-[[(2s)-2-[[(2s)-2-(3-cyclohexylpropanoylamino)-4-methylpentanoyl]amino]-5-methylhexanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]-5-(diaminomethylideneamino)pentanoyl]amino]butanediamide Chemical compound N([C@@H](CC(C)C)C(=O)N[C@@H](CCC(C)C)C(=O)N[C@@H](CN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCN=C(N)N)C(=O)N[C@@H](CC(N)=O)C(N)=O)C(=O)CCC1CCCCC1 KAFZOLYKKCWUBI-HPMAGDRPSA-N 0.000 description 1
- JFPNUDMVNKFIOQ-UHFFFAOYSA-N 2-bromo-5-(3-thiophen-2-ylthiophen-2-yl)thiophene Chemical compound S1C(Br)=CC=C1C1=C(C=2SC=CC=2)C=CS1 JFPNUDMVNKFIOQ-UHFFFAOYSA-N 0.000 description 1
- TUCRZHGAIRVWTI-UHFFFAOYSA-N 2-bromothiophene Chemical class BrC1=CC=CS1 TUCRZHGAIRVWTI-UHFFFAOYSA-N 0.000 description 1
- QUGOBTBFBNXICO-UHFFFAOYSA-N 2-thiophen-2-ylbutanoic acid Chemical compound CCC(C(O)=O)C1=CC=CS1 QUGOBTBFBNXICO-UHFFFAOYSA-N 0.000 description 1
- FYYLSCWWCHQDFX-UHFFFAOYSA-N 4-thiophen-2-ylbutan-1-ol Chemical compound OCCCCC1=CC=CS1 FYYLSCWWCHQDFX-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- ADWMECREYSMHCJ-UHFFFAOYSA-N C(CCC)P(O)(O)=O.IC1=C(SC=C1)C=1SC=CC1C=1SC=CC1 Chemical compound C(CCC)P(O)(O)=O.IC1=C(SC=C1)C=1SC=CC1C=1SC=CC1 ADWMECREYSMHCJ-UHFFFAOYSA-N 0.000 description 1
- CXGOMVZVKUUSTA-UHFFFAOYSA-N CCCCP(=O)(O)OC1=C(SC=C1)Br Chemical compound CCCCP(=O)(O)OC1=C(SC=C1)Br CXGOMVZVKUUSTA-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OBNLOEVHATYKMN-UHFFFAOYSA-N IC1=C(SC=C1)C=1SC=CC=1C=1SC=CC=1 Chemical compound IC1=C(SC=C1)C=1SC=CC=1C=1SC=CC=1 OBNLOEVHATYKMN-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- TZYWCYJVHRLUCT-VABKMULXSA-N N-benzyloxycarbonyl-L-leucyl-L-leucyl-L-leucinal Chemical compound CC(C)C[C@@H](C=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)OCC1=CC=CC=C1 TZYWCYJVHRLUCT-VABKMULXSA-N 0.000 description 1
- QUOYUMSLDZVTQS-UHFFFAOYSA-N P(OCCCC)(O)=O.IC1=C(SC=C1)C=1SC=CC1C=1SC=CC1 Chemical compound P(OCCCC)(O)=O.IC1=C(SC=C1)C=1SC=CC1C=1SC=CC1 QUOYUMSLDZVTQS-UHFFFAOYSA-N 0.000 description 1
- OXKSXNRCRIKSSK-UHFFFAOYSA-N P(OCCCC)(OCCCC)=O.S1C=CC=C1 Chemical compound P(OCCCC)(OCCCC)=O.S1C=CC=C1 OXKSXNRCRIKSSK-UHFFFAOYSA-N 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical group 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- SRVFFFJZQVENJC-IHRRRGAJSA-N aloxistatin Chemical compound CCOC(=O)[C@H]1O[C@@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCCC(C)C SRVFFFJZQVENJC-IHRRRGAJSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-L bis(triphenylphosphine)palladium(ii) dichloride Chemical compound [Cl-].[Cl-].[Pd+2].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 YNHIGQDRGKUECZ-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- MTNYZGOCZSKARY-UHFFFAOYSA-N butyl(thiophen-2-yloxy)phosphinic acid Chemical compound CCCCP(=O)(O)OC1=CC=CS1 MTNYZGOCZSKARY-UHFFFAOYSA-N 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- OSPSWZSRKYCQPF-UHFFFAOYSA-N dibutoxy(oxo)phosphanium Chemical compound CCCCO[P+](=O)OCCCC OSPSWZSRKYCQPF-UHFFFAOYSA-N 0.000 description 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-L diphosphonate(2-) Chemical compound [O-]P(=O)OP([O-])=O XQRLCLUYWUNEEH-UHFFFAOYSA-L 0.000 description 1
- 239000002019 doping agent Substances 0.000 description 1
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- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
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- 229910044991 metal oxide Inorganic materials 0.000 description 1
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- YDAYBTWNAFWLIX-UHFFFAOYSA-N methyl 4-(5-bromothiophen-2-yl)butanoate Chemical compound COC(=O)CCCC1=CC=C(Br)S1 YDAYBTWNAFWLIX-UHFFFAOYSA-N 0.000 description 1
- FUTXOYOSYBCRBT-UHFFFAOYSA-N methyl 4-thiophen-2-ylbutanoate Chemical compound COC(=O)CCCC1=CC=CS1 FUTXOYOSYBCRBT-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
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- 239000007800 oxidant agent Substances 0.000 description 1
- 150000003009 phosphonic acids Chemical group 0.000 description 1
- 238000000623 plasma-assisted chemical vapour deposition Methods 0.000 description 1
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- 238000006116 polymerization reaction Methods 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
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- 150000003384 small molecules Chemical class 0.000 description 1
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- 125000006850 spacer group Chemical group 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000010257 thawing Methods 0.000 description 1
- SIDQVCAARIJUNV-UHFFFAOYSA-N tributyl-(2-thiophen-2-ylthiophen-3-yl)stannane Chemical compound C1=CSC(C=2SC=CC=2)=C1[Sn](CCCC)(CCCC)CCCC SIDQVCAARIJUNV-UHFFFAOYSA-N 0.000 description 1
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 description 1
- BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Description
本発明は、室温で一般的な有機溶媒に可溶な、様々なセクシチオフェン(構造6において、R=H、n=0)の誘導体の合成について述べる。本発明では、TFTデバイスの半導体構成要素としてのこれらの化合物の用途についても述べている。
4−(2−チエニル)酪酸メチル1b
2,2−ジメトキシプロパン100mlに4−(2−チエニル酪酸)(10.0g、0.058モル)を溶かした溶液に、濃塩酸(0.5ml)を添加し、得られた溶液を室温で48時間撹拌した。過剰なジメトキシプロパンを蒸発させ、油状の残渣を真空中で蒸留すると(105℃、0.15mmHg)、メチルエステル1bが無色の油として得られた(10.2g、95%)。IR:1732cm-1(エステルカルボニル) 1H NMR(250MHz、25℃、CDCl3):δ 7.11(m,1H,Ar−H)、6.91(m,1H,Ar−H)、6.78(m,1H,Ar−H)、3.66(s,3H,OCH3)、2.87(t,2H,CH2CO2Me)、2.36(t,2H,Ar−CH2)、2.00(tt,2H,CH2CH2CH2)。
無水THF 100mlにメチルエステル1b(7.30g、0.04モル)を溶かした溶液に、水素化アルミニウムリチウムの2.5M THF溶液(10ml)をゆっくり添加した。添加終了後、この溶液を4時間還流し、次いで室温に冷却した。次いで塩酸(10%、25ml)をゆっくり添加し、得られた混合物をさらに30分間加熱した。室温に冷却した後、ジエチルエーテル(100ml)を添加し、有機層を分離してブライン(brain:塩類溶液または塩水)で洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を蒸発させると、アルコール1cが無色の油として得られた(5.4g、90%)。1H NMR(250MHz、25℃、CDCl3):δ 7.12(m,1H,Ar−H)、6.92(m,1H,Ar−H)、6.79(m,1H,Ar−H)、3.62(t,2H,CH2OH)、2.86(t,2H,Ar−CH2)、2.30(s,1H,OH)、2.00(m,4H,CH2CH2CH2CH2)。
無水アセトニトリル100mlに臭化リチウム(1.75g、0.02モル)を溶かした溶液に、クロロトリメチルシラン(2.60g、0.025モル)を添加し、その混合物を窒素中で30分間撹拌した。この溶液に、アルコール1c(1.56g、0.01モル)をアセトニトリル10mlに溶かした溶液をシリンジで添加し、得られた溶液を一晩還流した。この溶液を室温に冷却し、溶媒を減圧下で蒸発させ、残渣をジエチルエーテルに溶解した。固体を濾過によって除去して濾液を蒸発させると油状の褐色残渣が得られ、これを、溶離剤としてヘキサンを使用するシリカゲルのカラムを通したフラッシュクロマトグラフィにより精製した結果、ブロモブチルチオフェン1dが無色の油として得られた(1.9%、88%)。1H NMR(250MHz、25℃、CDCl3):δ 7.10(m,1H,Ar−H)、6.91(m,1H,Ar−H)、6.78(m,1H,Ar−H)、3.41(t,2H,CH2Br)、2.85(t,2H,Ar−CH2)、1.85(m,4H,CH2CH2CH2CH2)。
亜リン酸トリエチル20mlにブロモブチルチオフェン1d(4.58g、0.02モル)を溶かした溶液を20時間160℃に加熱し、この溶液に窒素を直接バブリングした。溶液を室温に冷却し、水50mlを添加して、得られた混合物を4時間撹拌した。生成物を塩化メチレンで抽出し、有機層を分離し、ブラインで洗浄し、次いで無水硫酸マグネシウム上で乾燥した。溶媒を蒸発させることにより油状の残渣が得られ、これを真空中で蒸留すると(0.12mmHg、135℃)、4−(2−チエニル)ブチルホスホン酸ジエチル1eが無色の油として得られた(6.0g、82%)。1H NMR(250MHz、25℃、CDCl3):δ 7.06(m,1H,Ar−H)、6.85(m,1H,Ar−H)、6.72(m,1H,Ar−H)、4.03(m,4H,POCH2CH3)、2.79(t,2H,Ar−CH2)、1.72(m,6H,CH2CH2CH2P)、1.26(t,6H,POCH2CH3)。
ジメチルホルムアミド(20ml)に4−(2−チエニル)ブチルホスホン酸ジエチル1e(2.78g、0.01モル)を溶かした溶液に、N−ブロモスクシンイミド(1.78g、0.01モル)を少量ずつ添加し、溶液を室温で一晩撹拌した。この反応混合物にジエチルエーテル(50ml)を添加し、次いで水で2回洗浄し(それぞれ50ml)、ブラインで1回洗浄し、無水硫酸マグネシウム上で乾燥した。溶媒を蒸発させることにより、4−(2−ブロモチエニル)ブチルホスホン酸ジエチル2aが薄黄色の油として得られた(3.2g、87%)。1H NMR(250MHz、25℃、CDCl3):δ 6.80(d,1H,Ar−H)、6.49(d,1H,Ar−H)、4.03(m,4H,POCH2CH3)、2.72(t,2H,Ar−CH2)、1.67(m,6H,CH2CH2CH2P)、1.27(t,6H,POCH2CH3)。
無水DMF(ジメチルホルムアミド)(30ml)に4−(2−ブロモチエニル)ブチルホスホン酸ジエチル2a(3.55g、0.01モル)を溶かした溶液に、窒素雰囲気中で5−トリブチルすず−(2,2’)ビチオフェン(4.54g、0.01モル)を添加した。この溶液に、塩化ビス(トリフェニルホスフィン)パラジウム(II)500mgを添加し、その混合物を3時間60℃に加熱し、次いで室温で20時間撹拌した。ジエチルエーテル(100ml)を添加し、混合物を水で数回洗浄し、次いでブラインで洗浄し、無水硫酸マグネシウム上で乾燥した。溶媒を蒸発させることにより、黄橙色の固体状残渣が得られ、これをシリカゲルのカラムでクロマトグラフィにかけた。酢酸エチルで溶離すると、溶媒を蒸発させた後、橙色の固体が得られた(3.0g、83%)。ヘキサンから結晶化することにより、分析上純粋な4−[5−(2,2’:5’,2’’)ターチエニル]ブチルホスホン酸ジエチル4aが得られた(3.0g、83%)。融点:92℃、1H NMR(250MHz、25℃、CDCl3):δ 7.16−6.94(m,6H,Ar−H)、6.66(m,1H,Ar−H)、4.08(m,4H,POCH2CH3)、2.79(t,2H,Ar−CH2)、1.75(m,6H,CH2CH2CH2P)、1.29(t,6H,POCH2CH3)。
無水DMF(20ml)に上記化合物4a(2.28g、5ミリモル)を溶かした溶液に、酢酸第二水銀(0.954g、3ミリモル)を添加し、その混合物を、窒素中、室温で1時間撹拌した。次いでこの溶液に、ヨウ素(1.27g、5ミリモル)を30分間にわたり少量ずつ添加し、その混合物を室温で20時間撹拌した。ジエチルエーテル(50ml)を添加し、その溶液を水で数回洗浄し、次いでブラインで洗浄し、無水硫酸マグネシウム上で乾燥した。溶媒を蒸発させることによって橙色の固体状残渣が得られ、これをトルエンとヘキサンの混合物(体積比50:50)から結晶化して、4−[5’’−ヨード−5−(2,2’:5’,2”−ターチエニル)]ブチルホスホン酸ジエチル5aが橙色の微結晶性化合物として得られた(2.5g、91%)。融点:115℃、1H NMR(250MHz、25℃、CDCl3):δ 7.12(m,1H,Ar−H)、6.94(m,3H,Ar−H)、6.78(m,1H,Ar−H)、6.66(m,1H,Ar−H)、4.05(m,4H,POCH2CH3)、2.79(t,2H,Ar−CH2)、1.70(m,6H,CH2CH2CH2P)、1.29(t,6H,POCH2CH3)。
5−ヨード−2,2’:5’,2’’−ターチエニルブチルホスホネート5a(950mg、1.67ミルモル)と、ヒドロキノン(160mg、1.4ミリモル)と、炭酸セシウム(700mg、2.1ミリモル)との混合物に、酢酸パラジウム(20mg、0.09ミリモル)とトリ−p−トリルホスフィン(30mg、0.1ミリモル)を無水DMF(10ml)に溶かした溶液を添加し、その混合物の凍結融解を3サイクル行うことによって脱気し、窒素を充填した。次いでこの混合物を70℃で4時間加熱し、室温に冷却し、次いでさらに20時間撹拌した。濃い橙色の固体を濾過によって分離し、ジエチルエーテルで数回洗浄し、真空中で乾燥した。1,2−ジクロロベンゼンから結晶化することにより、4−[5,2’’’’’−(2,2’:5’,2’’:5’’,2’’’:5’’’,2’’’’:5’’’’,2’’’’’−セクシチオフェンジイル)]−ブチルホスホン酸ビスジエチル6aが明るい赤橙色の微結晶性生成物として得られた(900mg、62%)。融点(DSC(示差走査熱量計)で測定):245℃
4−(5−ブロモ−2−チエニル)酪酸メチル2b
4−(2−ブロモチエニル)ブチルホスホン酸ジエチル2aを調製するために概略的に述べた手順に従って、4−(2−チエニル)酪酸メチル1bのNBS臭素化を行うことにより、4−(5−ブロモ−2−チエニル)酪酸メチル2bが無色の油として、90%を超える収率で得られた。沸点:0.15mmHgで138℃、1H NMR(250MHz、25℃、CDCl3):δ 6.82(d,1H,Ar−H)、6.52(d,1H,Ar−H)、3.64(s,3H,OCH3)、2.79(t,2H,CH2CO2Me)、2.33(t,2H,Ar−CH2)、1.93(tt,2H,CH2CH2CH2)。
4−[5−(2,2’:5’,2’’)ターチエニル]ブチルホスホン酸ジエチル4aを調製するために概略的に述べた手順に従い、5−トリブチルすず−2,2’−ビチオフェン3を用いて4−(5−ブロモ−2−チエニル)酪酸メチル2bのStilleカップリング反応を行った結果、ターチオフェン誘導体4bが、黄色の蛍光色をした固体として80%の収率で得られた。融点:81℃、1H NMR(250MHz、25℃、CDCl3):δ 7.20−7.13(m,2H,Ar−H)、7.04−6.95(m,4H,Ar−H)、6.68(m,1H,Ar−H)、3.66(s,3H,OCH3)、2.84(t,2H,CH2CO2Me)、2.38(t,2H,Ar−CH2)、1.99(tt,2H,CH2CH2CH2)。
上記化合物4aに関して概略的に述べた手順に従って、ターチオフェン誘導体4bのNBS臭素化を行った結果、4−[5−ブロモ−5’’−(2,2’:5’,2’’−ターチエニル)]酪酸メチル5bが黄緑色の固体として80%を超える収率で得られた。融点:134℃、1H NMR(250MHz、25℃、CDCl3):δ 7.14(m,1H,Ar−H)、6.98(m,3H,Ar−H)、6.81(m,1H,Ar−H)、6.99(m,1H,Ar−H)、3.68(s,3H,OCH3)、2.85(t,2H,CH2CO2Me)、2.39(t,2H,Ar−CH2)、2.01(tt,2H,CH2CH2CH2)。
4−[5−ブロモ−5’’−(2,2’:5’,2’’−ターチエニル)]酪酸メチル5b(600mg、1.25ミリモル)と、ヒドロキノン(200mg、1.8ミリモル)と、炭酸セシウム(400mg、1.25ミリモル)との混合物に、トリ−p−トリルホスフィン(100mg、0.3ミリモル)と酢酸パラジウム(100mg、0.45ミリモル)とを無水ジメチルホルムアミド10mlに溶かした溶液を添加した。この混合物を、凍結融解を3サイクル行うことによって脱気し、窒素を充填し、80℃で20時間加熱した。得られた黒色混合物を室温に冷却し、沈殿物を濾過してエタノールおよびジエチルエーテルで十分に洗浄し、真空中で乾燥した。1,2−ジクロロベンゼンから結晶化することによって、セクシチオフェン6bが赤橙色の結晶性化合物として得られた。
セクシチオフェン6aを薄膜トランジスタ(TFT)の半導体チャネルとして使用する方法を、以下に例示する。
(2)両端のアルキル基が1〜10個の炭素を有し、好ましくは2〜6個の炭素を有する上記(1)に記載の構造。
(3)前記末端環のアルキル基は、その末端炭素原子が極性官能基で置換されている上記(2)に記載の構造。
(4)前記極性官能基がジアルキルホスホネート基である上記(3)に記載の構造。
(5)前記極性官能基がホスホン酸基である上記(3)に記載の構造。
(6)前記極性官能基がカルボン酸基である上記(3)に記載の構造。
(7)前記極性官能基がカルボン酸エステル基である上記(3)に記載の構造。
(8)前記極性官能基がアミノ基である上記(3)に記載の構造。
(9)前記極性官能基がアミド基である上記(3)に記載の構造。
(10)前記極性官能基が水酸基である上記(3)に記載の構造。
(11)ソース領域およびドレイン領域と、前記ソース領域と前記ドレイン領域の間に延在して半導体有機材料を含むチャネル層と、前記チャネル層と隣り合うように間隔を空けて配置されたゲート領域と、前記ゲート領域と、前記ソース領域、前記ドレイン領域、および前記チャネル層との間の電気絶縁層とを含む電界効果トランジスタ。
(12)前記ソース領域、前記チャネル層、および前記ドレイン領域が基板表面上に配置され、前記電気絶縁層が前記チャネル層上に配置されて前記ソース領域から前記ドレイン領域まで延在し、前記ゲート領域が前記電気絶縁層上に配置されている上記(11)に記載の電界効果トランジスタ。
(13)前記ゲート領域が、基板表面上にゲート層として配置され、前記電気絶縁層が前記ゲート層上に配置され、前記ソース領域、前記チャネル層、および前記ドレイン領域が前記電気絶縁層上に配置されている上記(11)に記載の電界効果トランジスタ。
(14)前記有機材料が上記(1)のセクシチオフェン誘導体である上記(11)に記載の電界効果トランジスタ。
(15)前記セクシチオフェンが、前記セクシチオフェンを有機溶媒に溶かした溶液から塗布される上記(14)に記載の電界効果トランジスタ。
(16)有機材料が、高真空蒸着技法によって塗布される上記(14)に記載の電界効果トランジスタ。
(17)前記基板がフレキシブルな材料である上記(11)に記載の電界効果トランジスタ。
(18)前記基板がプラスチック材料からなる上記(11)に記載の電界効果トランジスタ。
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JP2001209836A Expired - Fee Related JP4218746B2 (ja) | 2000-07-12 | 2001-07-10 | 電界効果トランジスタ |
JP2008189903A Expired - Fee Related JP4912364B2 (ja) | 2000-07-12 | 2008-07-23 | 可溶性セクシチオフェン誘導体を含む組成物 |
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US (2) | US6414164B1 (ja) |
JP (2) | JP4218746B2 (ja) |
KR (1) | KR100478763B1 (ja) |
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EP0439627B1 (en) * | 1989-08-18 | 1996-07-10 | Idemitsu Kosan Company Limited | Organic electroluminescent element |
JP3006718B2 (ja) * | 1990-09-25 | 2000-02-07 | 科学技術振興事業団 | オリゴチオフェンを用いた電子素子 |
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JP3246189B2 (ja) * | 1994-06-28 | 2002-01-15 | 株式会社日立製作所 | 半導体表示装置 |
JP3132630B2 (ja) * | 1994-08-25 | 2001-02-05 | 科学技術振興事業団 | チオフェン誘導体の重合体とその製造法 |
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DE19633311A1 (de) * | 1996-08-19 | 1998-02-26 | Bayer Ag | Kratzfeste leitfähige Beschichtungen |
US6107117A (en) * | 1996-12-20 | 2000-08-22 | Lucent Technologies Inc. | Method of making an organic thin film transistor |
WO1999012989A1 (en) * | 1997-09-05 | 1999-03-18 | Cambridge Display Technology Ltd. | Compounds for electronic devices |
US6215130B1 (en) * | 1998-08-20 | 2001-04-10 | Lucent Technologies Inc. | Thin film transistors |
US6265243B1 (en) * | 1999-03-29 | 2001-07-24 | Lucent Technologies Inc. | Process for fabricating organic circuits |
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US6825358B2 (en) | 2004-11-30 |
US6414164B1 (en) | 2002-07-02 |
KR20020006444A (ko) | 2002-01-19 |
JP4218746B2 (ja) | 2009-02-04 |
KR100478763B1 (ko) | 2005-03-24 |
US20020072618A1 (en) | 2002-06-13 |
JP2009076868A (ja) | 2009-04-09 |
JP2002100782A (ja) | 2002-04-05 |
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