TW201726643A - 有機化合物、其製造方法、含有其之有機半導體材料及含有其之有機電晶體 - Google Patents
有機化合物、其製造方法、含有其之有機半導體材料及含有其之有機電晶體 Download PDFInfo
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- TW201726643A TW201726643A TW105126371A TW105126371A TW201726643A TW 201726643 A TW201726643 A TW 201726643A TW 105126371 A TW105126371 A TW 105126371A TW 105126371 A TW105126371 A TW 105126371A TW 201726643 A TW201726643 A TW 201726643A
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 107
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 54
- 239000000463 material Substances 0.000 title claims abstract description 49
- 238000000034 method Methods 0.000 title abstract description 87
- 150000002894 organic compounds Chemical class 0.000 title 1
- -1 transition metal salt Chemical class 0.000 claims abstract description 173
- 150000001875 compounds Chemical class 0.000 claims abstract description 124
- 239000002253 acid Substances 0.000 claims abstract description 32
- SYXXZXWLYNODHL-UHFFFAOYSA-N dinaphthothiophene Chemical class C1=CC=CC2=C(C3=C(C4=CC=CC=C4C=C3)S3)C3=CC=C21 SYXXZXWLYNODHL-UHFFFAOYSA-N 0.000 claims abstract description 28
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 22
- 150000003568 thioethers Chemical class 0.000 claims abstract description 18
- 150000003624 transition metals Chemical class 0.000 claims abstract description 16
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 9
- 150000004780 naphthols Chemical class 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- 230000018044 dehydration Effects 0.000 claims abstract description 5
- 238000006297 dehydration reaction Methods 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 87
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001424 substituent group Chemical group 0.000 claims description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 33
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 31
- 125000002015 acyclic group Chemical group 0.000 claims description 29
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000002560 nitrile group Chemical group 0.000 claims description 27
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 239000002904 solvent Substances 0.000 abstract description 41
- 230000008569 process Effects 0.000 abstract description 8
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical class C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 abstract 1
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- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 46
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- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000011156 evaluation Methods 0.000 description 19
- 239000000243 solution Substances 0.000 description 18
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- 239000012300 argon atmosphere Substances 0.000 description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 9
- 229910052732 germanium Inorganic materials 0.000 description 9
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 9
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
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- 125000000304 alkynyl group Chemical group 0.000 description 8
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- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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- 239000001301 oxygen Substances 0.000 description 8
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- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 8
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- 229910052782 aluminium Inorganic materials 0.000 description 7
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- 239000012043 crude product Substances 0.000 description 6
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- 239000003446 ligand Substances 0.000 description 6
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 6
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- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical group CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
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- 239000003054 catalyst Substances 0.000 description 2
- YTVGYERVQUDDIF-UHFFFAOYSA-K cerium(3+) 4-methylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.[Ce+3].C1(=CC=C(C=C1)S(=O)(=O)[O-])C.C1(=CC=C(C=C1)S(=O)(=O)[O-])C YTVGYERVQUDDIF-UHFFFAOYSA-K 0.000 description 2
- TZIBOXWEBBRIBM-UHFFFAOYSA-N cerium(3+) oxygen(2-) titanium(4+) Chemical compound [O--].[O--].[Ti+4].[Ce+3] TZIBOXWEBBRIBM-UHFFFAOYSA-N 0.000 description 2
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- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 description 2
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
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- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
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- PHWISQNXPLXQRU-UHFFFAOYSA-N n,n-dimethylcarbamothioyl chloride Chemical compound CN(C)C(Cl)=S PHWISQNXPLXQRU-UHFFFAOYSA-N 0.000 description 1
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- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
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- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QUMITRDILMWWBC-UHFFFAOYSA-N nitroterephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C([N+]([O-])=O)=C1 QUMITRDILMWWBC-UHFFFAOYSA-N 0.000 description 1
- 239000001272 nitrous oxide Substances 0.000 description 1
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- WLGDAKIJYPIYLR-UHFFFAOYSA-N octane-1-sulfonic acid Chemical compound CCCCCCCCS(O)(=O)=O WLGDAKIJYPIYLR-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
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- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
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- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- QJPQVXSHYBGQGM-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 QJPQVXSHYBGQGM-UHFFFAOYSA-N 0.000 description 1
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- YVBBRRALBYAZBM-UHFFFAOYSA-N perfluorooctane Chemical compound FC(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F YVBBRRALBYAZBM-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
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- 239000010452 phosphate Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 150000003057 platinum Chemical class 0.000 description 1
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- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- SYKXNRFLNZUGAJ-UHFFFAOYSA-N platinum;triphenylphosphane Chemical compound [Pt].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 SYKXNRFLNZUGAJ-UHFFFAOYSA-N 0.000 description 1
- RJQWVEJVXWLMRE-UHFFFAOYSA-N platinum;tritert-butylphosphane Chemical compound [Pt].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C RJQWVEJVXWLMRE-UHFFFAOYSA-N 0.000 description 1
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- BITYAPCSNKJESK-UHFFFAOYSA-N potassiosodium Chemical compound [Na].[K] BITYAPCSNKJESK-UHFFFAOYSA-N 0.000 description 1
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- 235000019396 potassium bromate Nutrition 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical group [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- SSOLNOMRVKKSON-UHFFFAOYSA-N proguanil Chemical compound CC(C)\N=C(/N)N=C(N)NC1=CC=C(Cl)C=C1 SSOLNOMRVKKSON-UHFFFAOYSA-N 0.000 description 1
- 229960005385 proguanil Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- KZVLNAGYSAKYMG-UHFFFAOYSA-N pyridine-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=N1 KZVLNAGYSAKYMG-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- ZCOSUVZGFDGWFV-UHFFFAOYSA-N pyrrolo[2,3-e]indole Chemical compound C1=CC2=NC=CC2=C2N=CC=C21 ZCOSUVZGFDGWFV-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 210000001525 retina Anatomy 0.000 description 1
- 229910001925 ruthenium oxide Inorganic materials 0.000 description 1
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- UREFKUKELTYZEO-UHFFFAOYSA-N ruthenium;triphenylphosphane Chemical compound [Ru].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 UREFKUKELTYZEO-UHFFFAOYSA-N 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 229960002218 sodium chlorite Drugs 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 1
- 229960005076 sodium hypochlorite Drugs 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229940045872 sodium percarbonate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- KGYLMXMMQNTWEM-UHFFFAOYSA-J tetrachloropalladium Chemical compound Cl[Pd](Cl)(Cl)Cl KGYLMXMMQNTWEM-UHFFFAOYSA-J 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- YCGAZNXXGKTASZ-UHFFFAOYSA-N thiophene-2,5-dicarboxylic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)S1 YCGAZNXXGKTASZ-UHFFFAOYSA-N 0.000 description 1
- BSXLLFUSNQCWJP-UHFFFAOYSA-N thiophene-2-sulfonic acid Chemical compound OS(=O)(=O)C1=CC=CS1 BSXLLFUSNQCWJP-UHFFFAOYSA-N 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
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 description 1
- YRQNNUGOBNRKKW-UHFFFAOYSA-K trifluororuthenium Chemical compound F[Ru](F)F YRQNNUGOBNRKKW-UHFFFAOYSA-K 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- JTJFQBNJBPPZRI-UHFFFAOYSA-J vanadium tetrachloride Chemical compound Cl[V](Cl)(Cl)Cl JTJFQBNJBPPZRI-UHFFFAOYSA-J 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- DCRSYTGOGMAXIA-UHFFFAOYSA-N zinc;oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[Ti+4].[Zn+2] DCRSYTGOGMAXIA-UHFFFAOYSA-N 0.000 description 1
- DUNKXUFBGCUVQW-UHFFFAOYSA-J zirconium tetrachloride Chemical compound Cl[Zr](Cl)(Cl)Cl DUNKXUFBGCUVQW-UHFFFAOYSA-J 0.000 description 1
- OMQSJNWFFJOIMO-UHFFFAOYSA-J zirconium tetrafluoride Chemical compound F[Zr](F)(F)F OMQSJNWFFJOIMO-UHFFFAOYSA-J 0.000 description 1
- GBNDTYKAOXLLID-UHFFFAOYSA-N zirconium(4+) ion Chemical compound [Zr+4] GBNDTYKAOXLLID-UHFFFAOYSA-N 0.000 description 1
- MQGNWZLWQBTZJR-UHFFFAOYSA-J zirconium(4+) tetraperchlorate Chemical compound [Zr+4].[O-][Cl](=O)(=O)=O.[O-][Cl](=O)(=O)=O.[O-][Cl](=O)(=O)=O.[O-][Cl](=O)(=O)=O MQGNWZLWQBTZJR-UHFFFAOYSA-J 0.000 description 1
- ZXAUZSQITFJWPS-UHFFFAOYSA-J zirconium(4+);disulfate Chemical compound [Zr+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZXAUZSQITFJWPS-UHFFFAOYSA-J 0.000 description 1
- MFFVROSEPLMJAP-UHFFFAOYSA-J zirconium(4+);tetraacetate Chemical compound [Zr+4].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O MFFVROSEPLMJAP-UHFFFAOYSA-J 0.000 description 1
- 229910000350 zirconium(IV) sulfate Inorganic materials 0.000 description 1
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B61/00—Other general methods
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- C09D11/00—Inks
- C09D11/52—Electrically conductive inks
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D201/00—Coating compositions based on unspecified macromolecular compounds
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/24—Electrically-conducting paints
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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
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices specially adapted for rectifying, amplifying, oscillating or switching and having potential barriers; Capacitors or resistors having potential barriers, e.g. a PN-junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
- H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
- H01L29/76—Unipolar devices, e.g. field effect transistors
- H01L29/772—Field effect transistors
- H01L29/78—Field effect transistors with field effect produced by an insulated gate
- H01L29/786—Thin film transistors, i.e. transistors with a channel being at least partly a thin film
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K10/00—Organic devices specially adapted for rectifying, amplifying, oscillating or switching; Organic capacitors or resistors having potential barriers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
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Abstract
提供一種對溶劑之溶解性優異且即便不經由複雜之製程亦容易地提供呈現高遷移率之膜之化合物、及使用其之有機半導體材料,進一步提供一種可簡便地製作實用性構成之有機電晶體之有機半導體墨水。一種二萘并噻吩衍生物之製造方法,藉由具有以下之(I)及(II)之步驟之二萘并噻吩衍生物之製造方法而解決課題。((I)第一步驟:使通式(A)表示之萘酚衍生物與通式(B)表示之萘硫醇衍生物於酸存在下進行脫水縮合而製造通式(C)表示之硫醚衍生物;(II)第二步驟:藉由使上述硫醚衍生物(C)於過渡金屬之鹽或過渡金屬之錯合物存在下進行脫氫反應而製造二萘并噻吩衍生物(D)。)
Description
本發明係關於一種二萘并噻吩衍生物、其製造方法、含有其之有機半導體材料、含有其之有機半導體墨水及含有其之有機電晶體。
以往,使用非晶矽或多晶矽作為材料而成之薄膜電晶體(TFT)被廣泛用作液晶顯示裝置或有機EL顯示裝置等之開關元件。然而,該等使用有矽材料之電晶體之製作所使用之CVD裝置之價格高,因此大型電晶體積體電路之製造會導致製造成本增大。又,由於矽材料在高溫下成膜,故而使用塑膠基板之第二代型可撓性顯示裝置因耐熱性之問題而無法開展。為了解決該問題,提出有代替矽半導體材料而將有機半導體材料用於通道(半導體層)之有機電晶體。
藉由使有機半導體材料墨水化,可於低溫下進行印刷成膜,因此無需大規模之製造設備,又,亦可應用於缺乏耐熱性之塑膠基板,期待對可撓性電子裝置之應用。
進一步,該等有機半導體材料先前存在「與矽半導體材料相比,半導體特性(遷移率)較低,因此電晶體之應答速度變慢,難以實用化」之課
題,近年來開始開發超過非晶矽之遷移率之材料。
例如,於專利文獻1中揭示有具有二萘并[2,3-b:2',3'-f]噻吩并[3,2-b]噻吩骨架之化合物於真空蒸鍍膜中顯示4.0cm2/Vs之遷移率,於專利文獻2~3中揭示有二萘并[2,3-b:2',3'-d]噻吩(以下簡稱為二萘并噻吩)衍生物於利用邊緣澆鑄(edge cast)法成膜之單晶薄膜中顯示11cm2/Vs之高遷移率,於非專利文獻1中揭示有2,7-二辛基[1]苯并噻吩并[3,2-b][1]苯并噻吩於利用雙噴墨法製作之單晶膜中雖然特性之偏差大,但最大顯示30cm2/Vs之高遷移率,於專利文獻4中揭示有經苯基取代之萘二硫屬化合物顯示0.7cm2/Vs之遷移率,於專利文獻5~6中揭示有表現高次液晶相之化合物於經由高次液晶相之薄膜中顯示5.7cm2/Vs之遷移率。如此,相繼報告了顯示出超過非晶矽之遷移率(0.5cm2/Vs)之半導體特性之有機半導體材料。
如此,雖然有機半導體之遷移率提高,但尚未達到實用化。其原因在於,所揭示之該等之遷移率係將利用邊緣澆鑄法或雙噴墨法所得之單晶膜、利用真空蒸鍍法所得之薄膜、利用旋轉塗布法所得之薄膜等利用提供均質之整體(bulk)之成膜法所製作之膜用於半導體層而進行評價者,於由與噴墨法或噴嘴印刷法等實用之印刷法相關之藉由墨水液滴之滴加(滴注(drop cast))及其乾燥而製作之多晶膜所構成之半導體層中,產生特性之降低。
專利文獻1:國際公開第2012/115236號
專利文獻2:國際公開第2013/125599號
專利文獻3:日本特開2007-197400號
專利文獻4:國際公開第2010/058692號
專利文獻5:國際公開第2012/121393號
專利文獻6:國際公開第2014/038708號
非專利文獻1:Nature,2011年,475卷,364頁
習知之有機半導體材料對溶劑之溶解性不足,因此難以調整墨水,因此與印刷相關之濕式成膜存在課題。又,關於具有溶劑溶解性之材料,亦會於濕式成膜時產生分子排列之散亂,或局部地結晶化等均質膜之製作存在課題,為了獲得高遷移率,需要實用化存在難度之成膜方法或繁雜之後成膜製程(退火處理等)。
因此,本發明之課題在於提供一種對溶劑之溶解性優異且即便不經由複雜之製程亦容易地(即,僅滴加墨水液滴並將其本身乾燥)提供呈現高遷移率之膜之化合物、及使用其之有機半導體材料,進一步提供一種可簡便地製作實用性構成之有機電晶體之有機半導體墨水。
本發明人為了達成上述目的而反覆努力研究,發現具有特定之取代基位置結構之二萘并噻吩由於溶劑溶解性優異,故而具有作為有機半導體墨水之適應性,進一步,即便為無需繁雜之處理、簡便且實用之濕
式成膜法(即,僅「滴加墨水液滴並將其本身乾燥」之方法),亦提供具有高遷移率之有機半導體膜,從而完成本發明。
即,本發明由以下項目構成。
1.一種二萘并噻吩衍生物之製造方法,其係通式(D)表示之二萘并噻吩衍生物之製造方法,具有以下之(I)及(II)之步驟:((I)第一步驟:使通式(A)表示之萘酚衍生物與通式(B)表示之萘硫醇衍生物於酸存在下進行脫水縮合而製造通式(C)表示之硫醚衍生物;(II)第二步驟:藉由使上述硫醚衍生物(C)於過渡金屬之鹽或過渡金屬之錯合物存在下進行脫氫反應而製造二萘并噻吩衍生物(D))。
(各式中,R1~R12表示氫原子或任意之取代基)
2.如1.所記載之製造方法,其中,上述R1~R12為氫原子、非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基(halogeno group)或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳
香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基。
3.如1.或2.所記載之製造方法,其中,關於上述R1~R12,R1與R12相互相同或不同,R2與R11相互相同或不同,R3與R10相互相同或不同,R4與R9相互相同或不同,R5與R8相互相同或不同,R6與R7相互相同或不同,但R1與R12、R2與R11、R3與R10、R4與R9、R5與R8、R6與R7此6組組合中之至少一個組合互不相同。
4.一種二萘并噻吩衍生物,其係以通式(E)表示(其中,化合物(E-a)、化合物(E-b)、化合物(E-c)、化合物(E-d)、化合物(E-e)、化合物(E-f)、化合物(E-g)、化合物(E-h)、化合物(E-i)、化合物(E-j)、化合物(E-k)及化合物(E-L)除外)。
(式中,R21~R32為氫原子或任意之取代基,R21與R32相互相同或不同,R22與R31相互相同或不同,R23與R30相互相同或不同,R24與R29相互相同或不同,R25與R28相互相同或不同,R26與R27相互相同或不同,但
R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27此6組組合中之至少一個組合互不相同)
(Alk1及Alk2表示碳原子數1~30之直鏈烷基)
(Ac表示乙醯基,T表示任意之取代基)
5.如4.所記載之二萘并噻吩衍生物,其中,上述R21~R32為氫原子、非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基
取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基。
6.如4.或5.所記載之二萘并噻吩衍生物,其中,上述R21~R32為氫原子、氟原子(氟基)、非環式或環式之碳原子數1~20之烷基、Ph-C≡C*(Ph表示亦可經取代之苯基,*表示鍵結位置)或Th-C≡C*(Th表示亦可經取代之噻吩基,*表示鍵結位置)。
7.如4.至6.所記載之二萘并噻吩衍生物,其中,上述取代基之6組組合(R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27)中之至少一個組合互不相同,且其以外之組合相互相同且為氫原子。
8.如4.至6.所記載之二萘并噻吩衍生物,其中,上述取代基之6組組合(R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27)中,R21與R32、R22與R31、R25與R28、R26與R27均相同且為氫原子,R23與R30相互相同或不同,R24與R29相互相同或不同,但R23與R30、R24與R29此2組組合中之至少一個組合互不相同。
9.一種有機半導體材料,其含有4.至8.中任一項所記載之二萘并噻吩衍生物。
10.一種有機半導體墨水,其含有9.所記載之有機半導體材料。
11.一種有機半導體膜,其含有9.所記載之有機半導體材料。
12.一種有機半導體元件,其含有9.所記載之有機半導體材料。
13.一種有機電晶體,其含有9.所記載之有機半導體材料。
根據本發明,可提供一種對溶劑之溶解性優異且以簡便且實用之濕式成膜法(即,僅「滴加墨水液滴並將其本身乾燥」之方法)提供高遷移率之有機半導體膜之具有特定之取代基位置結構的二萘并噻吩化合物、該二萘并噻吩化合物之製造方法、含有該化合物之有機半導體材料、含有該化合物之有機半導體墨水、及含有該化合物之有機電晶體。
1‧‧‧基板
2‧‧‧閘極電極
3‧‧‧閘極絕緣層
4‧‧‧有機半導體層
5‧‧‧源極電極
6‧‧‧汲極電極
圖1係底閘極(bottom gate)底部接觸(bottom contact)型(BC型)電晶體之概念圖。
圖2係底閘極頂部接觸(top contact)型(TC型)電晶體之概念圖。
(二萘并噻吩衍生物之製造方法)
對本發明之二萘并噻吩衍生物之製造方法進行說明。
本發明之製造方法之流程如以下所述。
(各式中,R1~R12表示氫原子或任意之取代基)
此處,本發明之製造方法之通式(A)、(B)、(C)、(D)表示之化合物之取代基R1~R12可相同,亦可不同,作為芳香族化合物之取代基,可使用公知慣用之任意之取代基(但為下述製造步驟(I)或(II)中不成為反應活性部之取代基)。
作為其具體例,可列舉:氫原子(包含氕、氘及氚)、非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子
亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基等,但並不限定於該等。再者,作為上述烷基、鹵基、芳香族基之具體例,可列舉與下述本發明之化合物(二萘并噻吩衍生物)之取代基相同者。
關於取代基之位置結構,利用下述本製造方法之特徵,於「R1與R12相同或不同,R2與R11相同或不同,R3與R10相同或不同,R4與R9相同或不同,R5與R8相同或不同,R6與R7相同或不同,R1與R12、R2與R11、R3與R10、R4與R9、R5與R8、R6與R7此6組組合中之至少一個組合互不相同」之情形時較佳。
本發明之二萘并噻吩衍生物之製造方法之特徵在於由如下步驟構成:(I)第一步驟:使通式(A)表示之萘酚衍生物與通式(B)表示之萘硫醇衍生物於酸存在下進行脫水縮合而製造通式(C)表示之硫醚衍生物;(II)第二步驟:藉由使上述硫醚衍生物(C)於過渡金屬之鹽或過渡金屬之錯合物存在下進行脫氫反應而製造二萘并噻吩衍生物(D)。
公知慣用之二萘并噻吩衍生物之製造方法(專利文獻2)由於使用300℃之反應等過激之條件,故而可導入之取代基種類有限,又,由於需要多階段之合成,故而產率亦低。進一步,於該方法中,於該方法之性質上,關於取代基之位置結構,僅能製造出R1與R12相同、R2與R11相同、R3與R10相同、R4與R9相同、R5與R8相同且R6與R7相同之衍生物。相對於此,於本製造方法中,由於反應條件溫和,又,步驟數少,故而可使用之取代基種類之範圍擴大,產率亦高。進一步,於本製造方法中,可製造如
「R1與R12相同或不同,R2與R11相同或不同,R3與R10相同或不同,R4與R9相同或不同,R5與R8相同或不同,R6與R7相同或不同,R1與R12、R2與R11、R3與R10、R4與R9、R5與R8、R6與R7此6組組合中之至少一個組合互不相同」之二萘并噻吩衍生物。此種衍生物如下所述,由於溶劑溶解性優異,故而具有作為有機半導體墨水之適應性,進一步凝聚性得以控制,因此可以簡便且實用之濕式成膜法(即,僅「滴加墨水液滴並將其本身乾燥」之方法)提供高半導體特性(遷移率)之有機半導體膜。
首先,對第一步驟進行說明。
於第一步驟中,使萘酚衍生物(A)與萘硫醇衍生物(B)於酸存在下進行脫水縮合而製成硫醚衍生物(C)。
萘酚衍生物(A)之市售者亦多,亦容易獲取。又,亦可依照日本特開昭61-115039等所記載之於使萘磺化後使萘磺酸與氫氧化鹼溶解之方法進行合成。
萘硫醇衍生物(B)之市售者亦多,亦容易獲取。又,亦可依照European Journal of Organic Chemistry 833-845(2010)等所記載之使萘酚與二甲基胺硫甲醯基氯化物(dimethylthiocarbamoyl chloride)進行縮合而製成O-硫胺甲酸酯(O-thiocarbamate)後,熱錯位成S-硫胺甲酸酯,最後水解之方法進行合成。
萘硫醇衍生物(B)相對於萘酚衍生物(A)之使用量莫耳比通常為0.1~10,較佳為0.2~5,更佳為0.4~2.5。
作為該反應中所使用之酸,只要為顯示酸性者,則無特別限制,可列舉無機酸、磺酸、金屬(或半金屬)之鹽、金屬(或半金屬)之
錯合物、固體酸等。
作為具體之無機酸,可列舉:鹽酸、氫溴酸、氫碘酸、過氯酸、硝酸、硫酸、磷酸、硼酸、聚磷酸、氟硫酸、氯硫酸、磷鎢酸等雜多酸等。
上述無機酸中,較佳為鹽酸、硝酸、硫酸、磷酸、聚磷酸、氟硫酸、氯硫酸,為了進一步提高反應性,進一步較佳為硫酸、磷酸、聚磷酸、氟硫酸。
作為具體之磺酸,可列舉:甲磺酸、乙磺酸、丙磺酸、丁磺酸、戊磺酸、己磺酸、庚磺酸、辛磺酸、壬磺酸、癸磺酸等烷基磺酸;三氟甲磺酸、全氟乙磺酸、全氟丙磺酸、全氟丁磺酸、全氟戊磺酸、全氟己磺酸、全氟庚磺酸、全氟辛磺酸、全氟壬磺酸、全氟癸磺酸等氟化烷基磺酸;苯磺酸、萘磺酸、吡啶磺酸、噻吩磺酸、對甲苯磺酸、對苯乙烯磺酸、二甲苯磺酸等亦可經烷基取代之芳基磺酸等。
上述磺酸中,較佳為甲磺酸、乙磺酸、丙磺酸、丁磺酸、戊磺酸、己磺酸、三氟甲磺酸、全氟乙磺酸、全氟丙磺酸、全氟丁磺酸、全氟戊磺酸、全氟己磺酸、苯磺酸、萘磺酸、對甲苯磺酸、對苯乙烯磺酸、二甲苯磺酸,
為了進一步提高反應性,進一步較佳為甲磺酸、乙磺酸、三氟甲磺酸、全氟乙磺酸、全氟丙磺酸、全氟丁磺酸。
所謂金屬(或半金屬)之鹽、金屬(或半金屬)之錯合物,
係指Be、B、Al、Si、P、S、Ti、V、Fe、Zn、Ga、Ge、As、Se、Zr、Nb、Mo、Cd、In、Sn、Sb、Te、Yb、Hf、Ta、W、Hg、Tl、Pb、Bi、U等元素或PO、SeO、VO等氧-元素鍵結體、與氟化氫、氯化氫、氫溴酸、碘化氫、過氯酸、硝酸、硫酸、磷酸、氟硫酸、氯硫酸、四氟硼酸、六氟磷酸等無機酸、烷基磺酸、亦可被鹵化之烷基磺酸、芳基磺酸、亦可具有烷基側鏈之芳基磺酸、膦酸、羧酸、亦可被鹵化之羧酸等酸性化合物之鹽或錯合物。
具體而言,可列舉:三氟化硼、三氯化硼、三氟化硼二乙醚錯合物、三氟化硼二甲硫醚錯合物;氟化鋁、氯化鋁、溴化鋁、過氯酸鋁、硝酸鋁、硫酸鋁、甲磺酸鋁、三氟甲磺酸鋁、對甲苯磺酸鋁、乙酸鋁、三氟乙酸鋁等鋁之鹽或錯合物;氟化鈧(III)、氯化鈧(III)、溴化鈧(III)、過氯酸鈧(III)、硝酸鈧(III)、硫酸鈧(III)、甲磺酸鈧(III)、三氟甲磺酸鈧(III)、對甲苯磺酸鈧(III)、乙酸鈧(III)、三氟乙酸鈧(III)等鈧(III)之鹽或錯合物;氟化鐵(III)、氯化鐵(III)、溴化鐵(III)、過氯酸鐵(III)、硝酸鐵(III)、硫酸鐵(III)、甲磺酸鐵(III)、三氟甲磺酸鐵(III)、對甲苯磺酸鐵(III)、乙酸鐵(III)、三氟乙酸鐵(III)等鐵(III)之鹽或錯合物;氟化鋅、氯化鋅、溴化鋅、過氯酸鋅、硝酸鋅、硫酸鋅、甲磺酸鋅、三氟甲磺酸鋅、對甲苯磺酸鋅、乙酸鋅、三氟乙酸鋅等鋅(II)之鹽或錯合物;
氟化鋯(IV)、氯化鋯(IV)、溴化鋯(IV)、過氯酸鋯(IV)、硝酸鋯(IV)、硫酸鋯(IV)、甲磺酸鋯(IV)、三氟甲磺酸鋯(IV)、對甲苯磺酸鋯(IV)、乙酸鋯(IV)、三氟乙酸鋯(IV)等鋯(IV)之鹽或錯合物;氟化銦(III)、氯化銦(III)、溴化銦(III)、過氯酸銦(III)、硝酸銦(III)、硫酸銦(III)、甲磺酸銦(III)、三氟甲磺酸銦(III)、對甲苯磺酸銦(III)、乙酸銦(III)、三氟乙酸銦(III)等銦(III)之鹽或錯合物;氟化鉍(III)、氯化鉍(III)、溴化鉍(III)、過氯酸鉍(III)、硝酸鉍(III)、硫酸鉍(III)、甲磺酸鉍(III)、三氟甲磺酸鉍(III)、對甲苯磺酸鉍(III)、乙酸鉍(III)、三氟乙酸鉍(III)等鉍(III)之鹽或錯合物;氯化錫(IV)、氯化銻(V)、氯化碲(IV)、溴化碲(IV)、氯化鉬(VI)、四氯化鈦(IV)、四氯化釩(IV)等。
於上述中,較佳為三氟化硼、三氯化硼、三氟化硼二乙醚錯合物、三氟化硼二甲硫醚錯合物、氟化鋁、氯化鋁、溴化鋁、過氯酸鋁、硝酸鋁、硫酸鋁、甲磺酸鋁、三氟甲磺酸鋁、對甲苯磺酸鋁、乙酸鋁、三氟乙酸鋁、氟化鐵(III)、氯化鐵(III)、溴化鐵(III)、過氯酸鐵(III)、硝酸鐵(III)、硫酸鐵(III)、甲磺酸鐵(III)、三氟甲磺酸鐵(III)、對甲苯磺酸鐵(III)、乙酸鐵(III)、三氟乙酸鐵(III)、氟化鋅、氯化鋅、溴化鋅、過氯酸鋅、硝酸鋅、硫酸鋅、甲磺酸鋅、三氟甲磺酸鋅、對甲苯磺酸鋅、乙酸鋅、三氟乙酸鋅、氟化銦(III)、氯化銦(III)、溴化銦(III)、過氯酸銦(III)、硝酸銦(III)、硫酸銦(III)、甲磺酸銦(III)、三氟甲磺酸銦(III)、對甲苯磺酸銦(III)、乙酸銦(III)、三氟乙酸銦(III)、氟化鉍(III)、氯化鉍(III)、溴化鉍(III)、
過氯酸鉍(III)、硝酸鉍(III)、硫酸鉍(III)、甲磺酸鉍(III)、三氟甲磺酸鉍(III)、對甲苯磺酸鉍(III)、乙酸鉍(III)、三氟乙酸鉍(III)、氯化錫(IV)、氯化鉬(VI)。
為了進一步提高反應性,進一步較佳為三氟甲磺酸鋁、三氟乙酸鋁、三氟甲磺酸鐵(III)、三氟乙酸鐵(III)、甲磺酸鋅、三氟甲磺酸鋅、甲磺酸銦(III)、三氟甲磺酸銦(III)、甲磺酸鉍(III)、三氟甲磺酸鉍(III)。
為了進一步提高反應性,尤佳為三氟甲磺酸鋁、三氟甲磺酸鐵(III)、三氟甲磺酸銦(III)、三氟甲磺酸鉍(III)。
作為具體之固體酸,為二氧化矽、α-氧化鋁等氧化物;二氧化矽氧化鋁、二氧化矽氧化鈦、沸石、氧化鋁氧化鈦、氧化鈦氧化鋅、二氧化矽氧化鋅、氧化鈦氧化鋯、二氧化矽鉬等非晶質或結晶質複合系金屬氧化物;將液體磷酸觸媒等液體酸吸附固定化於無機質載體之固定化酸等。
上述固體酸中,較佳為二氧化矽氧化鋁、二氧化矽氧化鈦、沸石。
該等固體酸觸媒之大小、形狀等並無特別限定,通常使用粉粒狀者,其粒徑較佳為10μm~10mm。
尤其,為了提高反應效率,較佳為多孔質且實質表面積(反應液接觸面積)大者。
該等酸觸媒可單獨使用或組合2種以上而使用,其使用量相對於萘酚衍生物(A)為0.001~10當量,較佳為0.005~5當量,更佳為0.01~2.5當
量。
作為反應溫度,只要為可獲得硫醚衍生物(C)之條件,則無特別限制,為0~250℃,較佳為25~200℃,更佳為40~150℃。
作為反應時間,只要為可獲得硫醚衍生物(C)之條件,則無特別限制,為10分鐘~72小時,較佳為30分鐘~48小時,更佳為1~24小時。
作為溶劑,只要對反應為非活性,則無特別限制,例如可列舉:二乙醚、四氫呋喃、1,4-二烷、二甲氧基乙烷、二丁醚等醚溶劑;乙酸乙酯、乙酸異丙酯、乙酸戊酯等酯溶劑;正己烷、庚烷、辛烷、環己烷、環戊烷等脂肪族烴溶劑;二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷等鹵素系溶劑;甲苯、苯、二甲苯等芳香族烴溶劑;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶劑;二甲基亞碸、環丁碸等含硫溶劑;乙腈、戊腈、苯甲腈等腈溶劑;乙酸、丙酸、丁酸等羧酸溶劑等,該等溶劑可單獨使用或組合2種以上而使用。
於本發明之第一步驟中,伴隨著反應進行而產生之水亦可不去除,可使用迪安-斯塔克(Dean-Stark)之裝置或蒸餾塔等連續地去除至系統外,亦可添加硫酸鈉、硫酸鎂、沸石等脫水劑而去除。
作為反應環境,亦可於空氣中進行,較佳為於氮或氬環境中
實施。
第一步驟中獲得之硫醚衍生物(C)亦可適當進行純化。作為純化方法,並無特別限定,例如可列舉管柱層析法、再結晶、昇華純化等。
其次,對第二步驟進行說明。
於第二步驟中,藉由使硫醚衍生物(C)於過渡金屬之鹽或過渡金屬之錯合物存在下進行脫氫反應而獲得作為目標化合物之二萘并噻吩衍生物(D)。
該反應中使用之過渡金屬係指作為第一過渡元素之Sc至Zn、作為第二過渡元素之Y至Cd、及作為第三過渡元素之La至Hg之金屬。
上述過渡金屬中,較佳為鐵、鈷、鎳、銅、鉬、釕、銠、鈀、鋨、銥、鉑、金,為了進一步提高反應性,進一步較佳為鎳、鉬、釕、銠、鈀、銥、鉑、金,為了更進一步提高反應性,尤佳為釕、鈀、鉑。
作為過渡金屬之鹽或過渡金屬之錯合物,可列舉:上述過渡金屬、與水、氟化氫、氯化氫、氫溴酸、碘化氫、過氯酸、硝酸、硫酸、磷酸、氟硫酸、氯硫酸、四氟硼酸、六氟磷酸、磷鎢酸等雜多酸、烷基磺酸、亦可被鹵化之烷基磺酸、芳基磺酸、亦可具有烷基側鏈之芳基磺酸、膦酸、羧酸、亦可被鹵化之羧酸等酸性化合物、烯烴、炔烴、胺、膦、胂、N-雜環碳烯、二亞苄基丙酮、乙醯丙酮、
一氧化碳、腈、salen等配位基之鹽或錯合物。
若具體地例示上述進一步更佳之過渡金屬之鹽或過渡金屬之錯合物,則可列舉:四(三苯基膦)鈀(0)、三(二亞苄基丙酮)二鈀(0)、雙(二亞苄基丙酮)鈀(0)、雙[1,2-雙(二苯基膦基)乙烷]鈀(0)、雙(三三級丁基膦)鈀(0)、雙(三環己基膦)鈀(0)、雙[二三級丁基(4-二甲基胺基苯基)膦]鈀(0)、氫氧化鈀(II)、硝酸鈀(II)、二氯苄基雙(三苯基膦)鈀(II)、二氯雙(三苯基膦)鈀(II)、氯烯丙基鈀(II)二聚物、二氯雙(乙腈)鈀(II)、二氯雙(苯甲腈)鈀(II)、乙酸雙(三苯基膦)鈀(II)、三氟乙酸雙(三苯基膦)鈀(II)、二氯(順,順-1,5-環辛烷二烯)鈀(II)、乙酸鈀(II)、三氟乙酸鈀(II)、三甲基乙酸鈀(II)、雙(三氟甲磺酸)四(乙腈)鈀(II)、乙醯丙酮鈀(II)、氯化鈀(II)、溴化鈀(II)、四氯鈀(II)酸鈉、二氯2,5-降莰二烯鈀(II)、硝酸(乙二胺)鈀(II)、二氯[9,9-二甲基-4,5-雙(二苯基膦基)二苯并哌喃]鈀(II)、二氯(1,5-環辛二烯)鈀(II)、二-μ-氯雙[5-羥基-2-[1-(羥基亞胺基)乙基]苯基]鈀(II)二聚物、二氯[二三級丁基(氯)膦]鈀(II)二聚物、氯[(三三級丁基膦)-2-(2-胺基聯苯)]鈀(II)、二氯雙(三鄰甲苯基膦)鈀(II)、二氯雙(甲基二苯基膦)鈀(II)、鈀/碳、鈀/氧化鋁、鈀/碳酸鋇、鈀/硫酸鋇等鈀鹽或錯合物;順-雙(2,2'-聯吡啶)二氯釕(II)二水合物、[(R)-2,2'-雙(二苯基膦基)-1,1'-聯萘]釕(II)二氯化物、羰基(二氫化)三(三苯基膦)釕(II)、氯亞硝基[N,N'-雙(3,5-二三級丁基亞柳基)-1,1,2,2
-四甲基乙二胺]釕(IV)、氯(五甲基環戊二烯基)釕(II)四聚物、二氯(對異丙基甲苯)釕(II)二聚物、1-羥基四苯基環戊二烯基(四苯基-2,4-環戊二烯-1-酮)-μ-氫四羰基二釕(II)、氯化釕(III)、氯(對異丙基甲苯)釕(II)、氯亞硝基釕(II)一水合物、三釕(0)十二羰基、三(2,4-戊二酮酸(2,4-pentandionato))釕(III)、二氯三(三苯基膦)釕(II)、釕/碳等釕鹽或錯合物;四(三苯基膦)鉑(0)、雙(三三級丁基膦)鉑(0)、氯化鉑(II)、乙醯丙酮鉑(II)、順-二胺(1,1-環丁烷二羧酸)鉑(II)、二氯順-二氨鉑(II)、二氯(1,5-環辛二烯)鉑(II)、(反-1,2-環己二胺)草酸鉑(II)等鉑鹽或錯合物。
上述過渡金屬之鹽或過渡金屬之錯合物可單獨使用或組合2種以上而使用,其使用量只要為可獲得二萘并噻吩(D)之範圍,則無特別限制,相對於硫醚(C)為0.001~10當量,較佳為0.005~5當量,更佳為0.01~2.5當量。
進一步,為了促進脫氫反應,亦可併用配位基。
作為配位基,例如可列舉:三甲基膦、三乙基膦、三正丁基膦、三三級丁基膦、三環己基膦、三苯基膦、三(鄰甲苯基)膦等單牙膦系配位基;雙(二苯基膦基)甲烷、1,2-雙(二苯基膦基)乙烷、2,2'-雙(二苯基膦基)-1,1'-聯萘、1,1'-雙(二苯基膦基)二茂鐵等雙牙膦系配位基等。
上述配位基可單獨使用或組合2種以上而使用,其使用量只要為可獲得二萘并噻吩(D)之範圍,則無特別限制,例如相對於上述過渡金屬之鹽或過渡金屬之錯合物為1~20當量,較佳為1~10當量,更佳為1
~5當量。
為了促進脫氫反應,亦可併用氧化劑。
作為氧化劑,例如可列舉:過乙酸、過氧化氫、雙氧水、脲-過氧化氫、Oxone、過碳酸鈉、過硼酸鈉、過硼酸鉀、過氧二硫酸二鉀、過硫酸四丁基銨、3-氯過苯甲酸、二甲基二環氧乙烷、三級丁基過氧化氫、過氧化苯甲醯等過氧化物;次氯酸鈉、亞氯酸鈉、溴酸鉀、過碘酸鈉、次氯酸三級丁基等高氧化度鹵化物;氧、臭氧、氟、氯、溴、一氧化氮、一氧化二氮等氧化性氣體;三氧化鉻、二氧化錳、乙酸錳(III)、過錳酸鉀、二鉻酸鉀、五氧化二釩(V)、三異丙氧基釩(V)氧化物、硝酸鈰(IV)銨、乙酸鉛(IV)、氧化鋨(VIII)等高氧化度金屬化合物;氟化銀、氯化銀、溴化銀、碘化銀、氧化銀、碳酸銀、氰化銀、硫酸銀、硝酸銀、乙酸銀、三氟乙酸銀、三甲基乙酸銀、乳酸銀、環己烷丁酸銀、甲磺酸銀、三氟甲磺酸銀、四氟硼酸銀等銀(I)化合物;氟化銅(II)、氯化銅(II)、溴化銅(II)、碘化銅(II)、氧化銅(II)、碳酸銅(II)、氰化銅(II)、硫酸銅(II)、硝酸銅(II)、乙酸銅(II)、三氟乙酸銅(II)、三甲基乙酸銅(II)、乳酸銅(II)、環己烷丁酸銅(II)、甲磺酸銅(II)、三氟甲磺酸銅(II)、四氟硼酸銅(II)等銅(II)化合物;氟化鐵(II)、氯化鐵(II)、溴化鐵(II)、碘化鐵(II)、氧化鐵(II)、碳酸鐵(II)、氰化鐵(II)、硫酸鐵(II)、硝酸鐵(II)、乙酸鐵(II)、三氟
乙酸鐵(II)、三甲基乙酸鐵(II)、乳酸鐵(II)、環己烷丁酸鐵(II)、甲磺酸鐵(II)、三氟甲磺酸鐵(II)、四氟硼酸鐵(II)等鐵(II)化合物;氟化鐵(III)、氯化鐵(III)、溴化鐵(III)、碘化鐵(III)、氧化鐵(III)、碳酸鐵(III)、氰化鐵(III)、硫酸鐵(III)、硝酸鐵(III)、乙酸鐵(III)、三氟乙酸鐵(III)、三甲基乙酸鐵(III)、乳酸鐵(III)、環己烷丁酸鐵(III)、甲磺酸鐵(III)、三氟甲磺酸鐵(III)、四氟硼酸鐵(III)等鐵(III)化合物;苯醌、蒽醌、2-(環己基亞磺醯基)-苯醌、2-(苯基亞磺醯基)-苯醌、2,3-二氯-5,6-二氰基-1,4-苯醌、四氯醌、鄰四氯醌等醌衍生物等。
較佳為過乙酸、過氧化氫、雙氧水、脲-過氧化氫、過氧二硫酸二鉀、Oxone、過硫酸四丁基銨、三氧化鉻、二氧化錳、乙酸錳(III)、硝酸鈰(IV)銨、3-氯過苯甲酸、氧、氟化銀、氯化銀、溴化銀、碘化銀、氧化銀、碳酸銀、氰化銀、硫酸銀、硝酸銀、乙酸銀、三氟乙酸銀、三甲基乙酸銀、乳酸銀、環己烷丁酸銀、甲磺酸銀、三氟甲磺酸銀、四氟硼酸銀、氟化銅(II)、氯化銅(II)、溴化銅(II)、碘化銅(II)、氧化銅(II)、碳酸銅(II)、氰化銅(II)、硫酸銅(II)、硝酸銅(II)、乙酸銅(II)、三氟乙酸銅(II)、三甲基乙酸銅(II)、乳酸銅(II)、環己烷丁酸銅(II)、甲磺酸銅(II)、三氟甲磺酸銅(II)、四氟硼酸銅(II)、氟化鐵(II)、氯化鐵(II)、溴化鐵(II)、碘化鐵(II)、氧化鐵(II)、碳酸鐵(II)、氰化鐵(II)、硫酸鐵(II)、硝酸鐵(II)、乙酸鐵(II)、三氟乙酸鐵(II)、三甲基乙酸鐵(II)、乳酸鐵(II)、環己烷丁酸鐵(II)、甲磺酸鐵(II)、三氟甲磺酸鐵(II)、四
氟硼酸鐵(II)。
更佳為氧、氟化銀、氯化銀、溴化銀、碘化銀、氧化銀、碳酸銀、氰化銀、硫酸銀、硝酸銀、乙酸銀、三氟乙酸銀、三甲基乙酸銀、乳酸銀、環己烷丁酸銀、甲磺酸銀、三氟甲磺酸銀、四氟硼酸銀。
進一步更佳為氧、硝酸銀、乙酸銀、三氟乙酸銀、三甲基乙酸銀、乳酸銀、環己烷丁酸銀、甲磺酸銀、三氟甲磺酸銀、四氟硼酸銀。
尤佳為氧、乙酸銀、三氟乙酸銀、三甲基乙酸銀、乳酸銀、甲磺酸銀、三氟甲磺酸銀。
上述氧化劑可單獨使用或組合2種以上而使用,其使用量只要為可獲得二萘并噻吩(D)之範圍,則無特別限制,相對於硫醚(C)為1~100當量,較佳為1~20當量,更佳為1~10當量。
為了促進脫氫反應,亦可併用羧酸。
作為羧酸,例如可列舉:甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、月桂酸、肉豆蔻酸、棕櫚酸、珠光子酸、硬脂酸、三甲基乙酸、2,2-二甲基丁酸、1-甲基-1-環己烷羧酸、2-苯基異丁酸等飽和脂肪族羧酸;油酸、亞麻油酸、次亞麻油酸、花生油酸、二十碳五烯酸等不飽和脂肪族羧酸;氟乙酸、三氟乙酸、氯乙酸、二氯乙酸、三氯乙酸等經鹵化之飽和脂肪族羧酸;苯甲酸、苯二甲酸、間苯二甲酸、對苯二甲酸、水楊酸、沒食子酸、苯六甲酸、肉桂酸等芳香族羧酸;
草酸、順丁烯二酸、反丁烯二酸、琥珀酸、戊二酸、黏康酸、己二酸、壬二酸、2,5-噻吩二羧酸、對苯二甲酸、2,5-吡二羧酸、萘-2,6-二羧酸、聯苯-4,4'-二羧酸、偶氮苯二羧酸、苯-1,2,4-三羧酸、苯-1,3,5-三苯甲酸、苯-1,2,4,5-四羧酸、萘-2,3,6,7-四羧酸、萘-1,4,5,8-四羧酸、聯苯-3,5,3',5'-四羧酸、及2-胺基對苯二甲酸、2-硝基對苯二甲酸、2-甲基對苯二甲酸、2-氯對苯二甲酸、2-溴對苯二甲酸、2,5-二羥對苯二甲酸、四氟對苯二甲酸、2,5-二羧基對苯二甲酸、二甲基-4,4'-聯苯二羧酸、四甲基-4,4'-聯苯二羧酸、二羧基-4,4'-聯苯二羧酸、2,5-吡二羧酸、2,5-二全氟對苯二甲酸、偶氮苯-4,4'-二羧酸、3,3'-二氯偶氮苯-4,4'-二羧酸、3,3'-二羥偶氮苯-4,4'-二羧酸、3,3'-二全氟偶氮苯-4,4'-二羧酸、3,5,3',5'-偶氮苯四羧酸、2,5-二甲基對苯二甲酸等多元羧酸。
較佳為甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、月桂酸、肉豆蔻酸、棕櫚酸、珠光子酸、硬脂酸、三甲基乙酸、2,2-二甲基丁酸、1-甲基-1-環己烷羧酸、2-苯基異丁酸、油酸、亞麻油酸、次亞麻油酸、花生油酸、二十碳五烯酸、氟乙酸、三氟乙酸、氯乙酸、二氯乙酸、三氯乙酸、苯甲酸、苯二甲酸、間苯二甲酸、對苯二甲酸、水楊酸、沒食子酸、苯六甲酸、肉桂酸。
更佳為甲酸、乙酸、丙酸、丁酸、戊酸、己酸、庚酸、辛酸、壬酸、癸酸、月桂酸、肉豆蔻酸、棕櫚酸、珠光子酸、硬脂酸、三甲基乙酸、2,2-二甲基丁酸、1-甲基-1-環己烷羧酸、2-苯基異丁酸、氟乙酸、三氟乙酸、氯乙酸、二氯乙酸、三氯乙酸,進一步更佳為乙酸、丙酸、三甲基乙酸、2,2-二甲基丁酸、1-甲基-
1-環己烷羧酸、三氟乙酸、三氯乙酸。
上述羧酸可單獨使用或組合2種以上而使用,其使用量只要為可獲得二萘并噻吩(D)之範圍,則無特別限制,相對於過渡金屬之鹽或錯合物為1~1000當量,較佳為1~500當量,更佳為1~100當量。
為了促進脫氫反應,亦可併用鹼。
作為鹼,例如可列舉:碳酸鈉、碳酸鉀、碳酸銫等碳酸鹽;磷酸鈉、磷酸二鈉、磷酸三鈉、磷酸鉀、磷酸鈣、磷酸二銨等磷酸鹽;氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫等氫氧化物、氟化鉀、氟化銫、氟化四丁基銨等氟化物;甲氧化鈉、乙氧化鈉、三級丁氧化鉀等烷氧化物;三甲胺、三乙胺、三丁胺、二異丙基乙胺、N-甲基嗎福啉、N-甲基吡咯啶、N-甲基哌啶、1,8-二氮雜雙環[5.4.0]十一-7-烯、1,4-二氮雜雙環[2.2.2]辛烷等三級胺;如吡啶、甲基吡啶、乙基吡啶、丙基吡啶、丁基吡啶、三級丁基吡啶之2,3-二甲基吡啶、2,4-二甲基吡啶、2,5-二甲基吡啶、2,6-二甲基吡啶、3,5-二甲基吡啶、2-甲基-5-乙基-吡啶、2,6-二異丙基吡啶、2,6-二三級丁基吡啶等吡啶衍生物。
較佳為碳酸鈉、碳酸鉀、碳酸銫、磷酸鈉、磷酸二鈉、磷酸三鈉、磷酸鉀、磷酸鈣、磷酸二銨、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫、氟化鉀、氟化銫、氟化四丁基銨、甲氧化鈉、乙氧化鈉、三級丁氧化鉀、三甲胺、三乙胺、三丁胺、二異丙基乙胺、N-甲基嗎福啉、N-甲基吡咯啶、N-甲基哌啶、1,8-二氮雜雙環[5.4.0]十一-7-烯、1,4-二
氮雜-雙環[2.2.2]辛烷。
更佳為碳酸鈉、碳酸鉀、碳酸銫、磷酸鈉、磷酸二鈉、磷酸三鈉、磷酸鉀、磷酸鈣、磷酸二銨、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫、氟化鉀、氟化銫、氟化四丁基銨等氟化物、甲氧化鈉、乙氧化鈉、三級丁氧化鉀,尤佳為碳酸鈉、碳酸鉀、碳酸銫、磷酸鈉、磷酸二鈉、磷酸三鈉、磷酸鉀、磷酸鈣、磷酸二銨、氫氧化鋰、氫氧化鈉、氫氧化鉀、氫氧化銫。
上述鹼可單獨使用或組合2種以上而使用,其使用量只要為可獲得二萘并噻吩(D)之範圍,則無特別限制,相對於硫醚(C)為1~100當量,較佳為1~20當量,更佳為1~10當量。
作為反應溫度,只要為可獲得二萘并噻吩衍生物(D)之條件,則無特別限制,為0~250℃,較佳為10~200℃,更佳為25~160℃。
作為反應時間,只要為可獲得二萘并噻吩衍生物(D)之條件,則無特別限制,為10分鐘~72小時,較佳為30分鐘~48小時,更佳為1~24小時。
亦可不使用溶劑。於使用溶劑之情形時,只要對反應為非活性,則無特別限制,例如可列舉:二乙醚、四氫呋喃、1,4-二烷、二甲氧基乙烷、二丁醚等醚溶劑;乙酸乙酯、乙酸異丙酯、乙酸戊酯等酯溶劑;正己烷、庚烷、辛烷、環己烷、環戊烷等脂肪族烴溶劑;
二氯甲烷、氯仿、四氯化碳、1,2-二氯乙烷等鹵化溶劑;甲苯、苯、二甲苯等芳香族烴溶劑;N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯啶酮等醯胺溶劑;二甲基亞碸、環丁碸等含硫溶劑;乙腈、戊腈、苯甲腈等腈溶劑;乙酸、丙酸、丁酸等羧酸溶劑等;該等溶劑可單獨使用或組合2種以上而使用。
作為反應環境,為空氣、氧、氮、氬、二氧化碳等,並不受特別限制,於使用氧作為氧化劑之情形時,可於空氣或氧下進行。
第二步驟中獲得之二萘并噻吩衍生物(D)亦可適當進行純化。作為純化方法,並無特別限定,例如可列舉管柱層析法、再結晶、昇華純化之方法。
(二萘并噻吩衍生物)
以下,對本發明之二萘并噻吩衍生物進行說明。
本發明之二萘并噻吩衍生物係通式(E)表示之化合物。其中,化合物(E-a)、化合物(E-b)、化合物(E-c)、化合物(E-d)、化合物(E-e)、化合物(E-f)、化合物(E-g)、化合物(E-h)、化合物(E-i)、化合物(E-j)、化合物(E-k)及化合物(E-L)除外。
(式中,R21~R32為氫原子或任意之取代基,R21與R32相同或不同,R22與R31相同或不同,R23與R30相同或不同,R24與R29相同或不同,R25與R28相同或不同,R26與R27相同或不同,但R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27此6組組合中之至少一個組合互不相同)
(Alk1及Alk2表示碳原子數1~30之直鏈烷基)
本發明之化合物之特徵在於,上述取代基之6組組合中之至少一個組合不同。於上述6組組合分別相同之情形時(即,R21與R32相同,R22與R31相同,R23與R30相同,R24與R29相同,R25與R28相同,且R26與R27相同),分子之對稱性成為C2v,對稱性變高,結晶性提高。因此,凝聚能過度地上升,藉由溶液(墨水)滴加(滴注)及其乾燥而製作之多晶膜之膜質降低(一般而言,大結晶粒析出,膜之均質性降低),半導體特性降低。
另一方面,由於本發明之化合物之對稱性低,故而凝聚能得到適度地控制,藉由溶液(墨水)滴加(滴注)及其乾燥而製作之多晶膜之膜質高,
因此半導體特性高。
就此種觀點而言,作為取代基之位置結構,較佳為R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27此6組組合中之至少一個組合互不相同,且其以外之組合相互相同且為氫原子。
為了獲得更高之遷移率之化合物,尤佳為R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27之6組組合中,R21與R32、R22與R31、R25與R28、R26與R27均相同且為氫原子,R23與R30相同或不同,R24與R29相同或不同,但R23與R30、R24與R29此2組組合中之至少一個組合互不相同。
接下來,對本發明之化合物之取代基進行說明。
作為本發明之通式(E)表示之化合物之取代基R21~R32,只要為作為芳香族化合物之取代基公知慣用者,則可無限制地使用,例如,可列舉選自如下基中之基:非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子
亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基。
具體而言,非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))為(A-1)碳原子數1~20之直鏈或支鏈烷基、(A-2)碳數3~20之脂環式烷基、(A-3)碳原子數1~19之烷氧基、(A-4)碳原子數2~19之烷氧基烷基、(A-5)碳原子數2~20之烯基、(A-6)碳原子數2~20之烷醯基(alkanoyl group)、(A-7)碳原子數3~20之烷醯基烷基、(A-8)碳原子數2~20之烷氧基羰基、(A-9)碳原子數2~20之烷醯氧基(alkanoyloxy group)、(A-10)碳原子數1~19之烷基氫硫基、(A-11)碳原子數2~19之烷基氫硫基烷基、(A-12)碳原子數1~19之烷基磺醯基、(A-13)碳原子數2~19之烷基磺醯基烷基、(A-14)碳原子數1~19之烷基亞磺醯基、(A-15)碳原子數2~19之烷基亞磺醯基烷基、(A-16)碳原子數1~19之烷基胺基、(A-17)碳原子數2~19之烷基胺基烷基、(A-18)碳原子數2~20之炔基、(A-19)亦可具有取代基之經芳香族烴基取代之炔基或亦可具有取代基之經雜芳香族基取代之炔基。
於上述(A-1)~(A-19)中,就提高本發明之化合物之成膜性與遷移率之觀點而言,較佳為(A-1)碳原子數1~20之直鏈或支鏈烷基、(A-2)碳數3~20之脂環式烷基、(A-3)碳原子數1~19之烷
氧基、(A-4)碳原子數2~19之烷氧基烷基、(A-5)碳原子數2~20之烯基、(A-10)碳原子數1~19之烷基氫硫基、(A-11)碳原子數2~19之烷基氫硫基烷基、(A-18)碳原子數2~20之炔基、或(A-19)亦可具有取代基之經芳香族烴基取代之炔基或亦可具有取代基之經雜芳香族基取代之炔基,為了獲得更高之遷移率之化合物,尤佳為(A-1)碳原子數1~20之直鏈或支鏈烷基、(A-4)碳原子數2~19之烷氧基烷基、或(A-19)亦可具有取代基之經芳香族烴基取代之炔基或亦可具有取代基之經雜芳香族基取代之炔基。
作為(A-1)之具體例,可列舉:甲基、乙基、正丙基、正丁基、正戊基、正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正二十烷基等直鏈烷基;異丙基、異丁基、異戊基、新戊基、1-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、1-甲基己基、環己基甲基、三級辛基、1-甲基庚基、2-乙基己基、3-乙基庚基、2-丙基戊基、2,2-二甲基庚基、2,6-二甲基-4-庚基、3,5,5-三甲基己基、1-甲基癸基、1-己基庚基等支鏈烷基;環戊基、環己基、4-甲基環己基、環庚基、環辛基等環狀烷基等。
作為(A-4)之具體例,可列舉:2-甲氧基乙基、2-乙氧基乙基、2-正丙氧基乙基、2-異丙氧基乙基、2-正丁氧基乙基、2-正己氧基乙基、2-(2'-乙基丁氧基)乙基、2-正庚氧基乙基、2-正辛氧基乙基、2-(2'-乙基己氧基)乙基、2-正癸氧基乙基、2-正十二烷氧
基乙基、2-正十四烷氧基乙基、2-環己氧基乙基、2-甲氧基丙基、3-甲氧基丙基、3-乙氧基丙基、3-正丙氧基丙基、3-異丙氧基丙基、3-正丁氧基丙基、3-正戊氧基丙基、3-正己氧基丙基、3-(2'-乙基丁氧基)丙基、3-正辛氧基丙基、3-(2'-乙基己氧基)丙基、3-正癸氧基丙基、3-正十二烷氧基丙基、3-正十四烷氧基丙基、3-環己氧基丙基、4-甲氧基丁基、4-乙氧基丁基、4-正丙氧基丁基、4-異丙氧基丁基、4-正丁氧基丁基、4-正己氧基丁基、4-正辛氧基丁基、4-正癸氧基丁基、4-正十二烷氧基丁基、5-甲氧基戊基、5-乙氧基戊基、5-正丙氧基戊基、5-正戊氧基戊基、6-甲氧基己基、6-乙氧基己基、6-異丙氧基己基、6-正丁氧基己基、6-正己氧基己基、6-正癸氧基己基、4-甲氧基環己基、7-甲氧基庚基、7-乙氧基庚基、7-異丙氧基庚基、8-甲氧基辛基、8-乙氧基辛基、9-甲氧基壬基、9-乙氧基壬基、10-甲氧基癸基、10-乙氧基癸基、10-正丁氧基癸基、11-甲氧基十一烷基、12-甲氧基十二烷基、12-乙氧基十二烷基、12-異丙氧基十二烷基、14-甲氧基十四烷基、環己氧基乙基、環己氧基丙基等。
作為(A-19)之具體例,可列舉:通式(A-19-1)表示之亦可具有取代基之經苯基取代之乙炔基、或通式(A-19-2)表示之亦可具有取代基之經噻吩基取代之乙炔基。作為上述取代基之具體例,可列舉碳原子數1~20之直鏈或支鏈烷基。
(Ra19表示任意之取代基)
具體而言,上述鹵基為氟基(氟原子)、氯基(氯原子)、溴基(溴原子)、碘基(碘原子)。
於上述鹵基中,就提高本發明之化合物之成膜性與遷移率之觀點而言,較佳為氟基及氯基,為了獲得更高之遷移率之化合物,尤佳為氟基。
具體而言,上述芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))為(B-1)未經取代之芳香族烴基或雜芳香族基、(B-2)鹵化芳香族烴基或雜芳香族基、(B-3)芳香族烴基或雜芳香族基以單鍵連結之芳香族烴基或雜芳香族基、(B-4)腈化芳香族烴基或雜芳香族基、(B-5)經碳原子數1~20之直鏈或支鏈烷基取代之芳香族烴基或雜芳香族基、(B-6)經碳數3~20之脂環式烷基取代之芳香族烴基或雜芳香族基、(B-7)經碳原子數1~19之烷氧基取代之芳香族烴基或雜芳香族基、(B-8)經碳原子數2~19之烷氧
基烷基取代之芳香族烴基或雜芳香族基、(B-9)經碳原子數2~20之烯基取代之芳香族烴基或雜芳香族基、(B-10)經碳原子數2~20之烷醯基取代之芳香族烴基或雜芳香族基、(B-11)經碳原子數3~20之烷醯基烷基取代之芳香族烴基或雜芳香族基、(B-12)經碳原子數2~20之烷氧基羰基取代之芳香族烴基或雜芳香族基、(B-13)經碳原子數2~20之烷醯氧基取代之芳香族烴基或雜芳香族基、(B-14)經碳原子數1~19之烷基氫硫基取代之芳香族烴基或雜芳香族基、(B-15)經碳原子數2~19之烷基氫硫基烷基取代之芳香族烴基或雜芳香族基、(B-16)經碳原子數1~19之烷基磺醯基取代之芳香族烴基或雜芳香族基、(B-17)經碳原子數2~19之烷基磺醯基烷基取代之芳香族烴基或雜芳香族基、(B-18)經碳原子數1~19之烷基亞磺醯基取代之芳香族烴基或雜芳香族基、(B-19)經碳原子數2~19之烷基亞磺醯基烷基取代之芳香族烴基或雜芳香族基、(B-20)經碳原子數1~19之烷基胺基取代之芳香族烴基或雜芳香族基、(B-21)經碳原子數2~19之烷基胺基烷基取代之芳香族烴基或雜芳香族基、(B-22)經碳原子數2~20之炔基取代之芳香族烴基或雜芳香族基。
於上述(B-1)~(B-22)中,就提高本發明之化合物之成膜性與遷移率之觀點而言,較佳為(B-1)未經取代之芳香族烴基或雜芳香族基、(B-2)鹵化芳香族烴基或雜芳香族基、(B-3)芳香族烴基或雜芳香族基以單鍵連結之芳香族烴基或雜芳香族基、(B-5)經碳原子數1~20之直鏈或支鏈烷基取代之芳香族烴基或雜芳香族基、(B-6)經碳數1~20之脂環式烷基取代之芳香族烴基或雜芳香族基、(B-7)經碳原子數1~19之烷氧基取代之芳香族烴基或雜芳香族基、(B-8)經碳原子數2~19
之烷氧基烷基取代之芳香族烴基或雜芳香族基、(B-9)經碳原子數2~20之烯基取代之芳香族烴基或雜芳香族基、(B-14)經碳原子數1~19之烷基氫硫基取代之芳香族烴基或雜芳香族基、(B-15)經碳原子數2~19之烷基氫硫基烷基取代之芳香族烴基或雜芳香族基、(B-20)經碳原子數1~19之烷基胺基取代之芳香族烴基或雜芳香族基、(B-21)經碳原子數2~19之烷基胺基烷基取代之芳香族烴基或雜芳香族基、(B-22)經碳原子數2~20之炔基取代之芳香族烴基或雜芳香族基,為了獲得更高之遷移率之化合物,尤佳為(B-1)未經取代之芳香族烴基或雜芳香族基、(B-2)鹵化芳香族烴基或雜芳香族基、(B-3)芳香族烴基或雜芳香族基以單鍵連結之芳香族烴基或雜芳香族基、(B-5)經碳原子數1~20之直鏈或支鏈烷基取代之芳香族烴基或雜芳香族基、(B-6)經碳數1~20之脂環式烷基取代之芳香族烴基或雜芳香族基、(B-7)經碳原子數1~19之烷氧基取代之芳香族烴基或雜芳香族基、(B-8)經碳原子數2~19之烷氧基烷基取代之芳香族烴基或雜芳香族基。
作為(B-1)之具體例,可列舉:苯基、萘基、薁基、二氫苊基、蒽基、菲基、稠四苯基、茀基、芘基、基(chrysenyl group)、苝基等未經取代之碳數6~24之單環或多環式芳香族烴基;吡咯基、吲哚基、呋喃基、噻吩基、咪唑基、苯并呋喃基、三唑基、苯并三唑基、苯并噻吩基、吡唑基、吲哚基、喹啉基、異喹啉基、咔唑基、二苯并呋喃基、二苯并噻吩基、吲哚啉基、噻唑基、吡啶基、嘧啶基、吡基、嗒基、噻二基、二唑基、苯并喹啉基、噻二唑基、吡咯并噻唑基、吡咯并嗒基、四唑基、唑基等未經取代之5員環或6員環
之雜芳香族基、或於該雜芳香族基縮合其他芳香族基而成之多環式雜芳香族基等。
作為(B-2)之具體例,可列舉:4-氟苯基、2,6-氟苯基、4-氯苯基、2,3,4,5,6-全氟苯基、氟吡啶基、氟吲哚基等上述芳香族烴基或雜芳香族基經氟基、氯基、溴基、碘基等鹵基取代者等。
作為(B-3)之具體例,可列舉:聯苯基、聯三苯基、聯萘基、聯吡啶基、聯噻吩基(bithienyl group)、三聯噻吩基(terthienyl group)、四聯噻吩基(quaterthienyl group)、五聯噻吩基(quinquethienyl group)、六聯噻吩基(sexithienyl group)、呋喃基苯基、噻吩基苯基等。
作為(B-5)之具體例,可列舉:甲苯基、二甲苯基、乙基苯基、正丙基苯基、異丙基苯基、正丁基苯基、三級丁基苯基、正戊基苯基、正己基苯基、正庚基苯基、正辛基苯基、2-乙基己基苯基、正十苯基、硬脂基苯基、5-甲基噻吩基、5-己基噻吩基、5-十噻吩基、5-硬脂基噻吩基等。
作為(B-6)之具體例,可列舉:環己基苯基、4-甲基環己基苯基、4-乙基環己基苯基等。
作為(B-7)之具體例,可列舉:甲氧基苯基、乙氧基苯基、丙氧基苯基、異丙氧基苯基、丁氧基苯基、戊氧基苯基、己氧基苯基、庚氧基苯基、辛氧基苯基、2-乙基己氧基苯基、癸氧基苯基、十二烷氧基苯基、硬脂氧基苯基等。
作為(B-8)之具體例,可列舉:4-(2-乙氧基乙基)苯基、4-(2-正己氧基乙基)苯基、4-(2-正庚氧基乙基)苯基、4-(2-正十四烷
氧基乙基)苯基、4-(2-環己氧基乙基)苯基、4-(12-乙氧基十二烷基)苯基、4-(環己氧基乙基)苯基、5-(2-乙氧基乙基)噻吩基、5-(2-正十四烷氧基乙基)噻吩基、5-(2-環己氧基乙基)噻吩基、5-(12-乙氧基十二烷基)噻吩基等。
以下,例示本發明之化合物之具體例,但本發明所使用之化合物並不限定於該等。
(有機半導體材料.墨水)
本發明之化合物可用作以有機半導體元件作為用途之有機半導體材
料。為了將本發明之化合物用作有機半導體,通常以膜形態(有機半導體膜或有機半導體層)使用。於膜之形成時,亦可藉由真空蒸鍍等公知慣用之乾式成膜法而形成,較佳為藉由能夠低溫成膜且生產性優異之濕式成膜法(塗布法或印刷法)而形成,因此,本發明之化合物、即有機半導體材料較佳為以墨水之形式使用。為了製備墨水,將本發明之化合物溶解於溶劑。又,於無損半導體特性之範圍,為了賦予墨水特性(印刷適應性),亦可添加氟系或矽系等之調平劑、及聚苯乙烯或丙烯酸樹脂或高分子系有機半導體化合物等高分子化合物作為黏度調整劑。
所使用之溶劑可為任意者,又,亦可混合2種以上之溶劑而使用。具體而言,可列舉:正己烷、正辛烷、正癸烷、正十二烷等脂肪族系溶劑;環己烷等脂環式系溶劑;苯、甲苯、異丙苯、鄰二甲苯、間二甲苯、對二甲苯、對異丙基甲苯、1,3,5-三甲苯、大茴香醚、2-甲基大茴香醚、3-甲基大茴香醚、4-甲基大茴香醚、2,5-二甲基大茴香醚、3,5-二甲氧基甲苯、2,4-二甲基大茴香醚、苯乙醚、苯甲酸甲酯、苯甲酸乙酯、苯甲酸丙酯、苯甲酸丁酯、1,5-二甲基四氫萘、正丙基苯、正丁基苯、正戊基苯、1,3,5-三乙基苯、1,3-二甲氧基苯、2,5-二乙基二苯、氯苯、鄰二氯苯、三氯苯等芳香族系溶劑;四氫呋喃、二烷、乙二醇二乙醚、大茴香醚、苄基乙醚、乙基苯醚、二苯醚、甲基三級丁醚等醚系溶劑;乙酸甲酯、乙酸乙酯、乙基賽路蘇、丙二醇甲醚乙酸酯等酯系溶劑;甲醇、乙醇、異丙醇等醇系溶劑;丙酮、甲基乙基酮、環己酮、2-己酮、2-庚酮、3-庚酮等酮系溶劑;
此外,可列舉二甲基甲醯胺、二甲基亞碸、二乙基甲醯胺等,但並不限定於該等。
作為所製備之液體組成物中之本發明之化合物之濃度,較佳為0.01~20重量%,進一步較佳為0.1~10重量%。
又,本發明之有機半導體墨水視用途,除包含本發明之化合物以外,亦可包含其他有機半導體材料,即電子供應性材料、電子接受性材料、電子傳輸性材料、電洞傳輸性材料、發光材料、光吸收材料等。作為此種材料,例如可列舉顯示半導體性質之π共軛系高分子、顯示半導體性質之非π共軛系高分子、低分子系有機半導體化合物等。
本發明之有機半導體墨水提供分子配置之秩序性高且均質之有機半導體膜。因此,所獲得之有機半導體膜可表現出高遷移率。又,為了獲得分子配置之秩序性高之膜,無需進行特殊之印刷成膜、或熱退火等特別之處理,僅滴加該墨水並將其乾燥亦可獲得高遷移率之有機半導體膜。
(有機半導體元件)
接下來,對本發明之有機半導體元件進行說明。本發明之有機半導體元件係將本發明之化合物含有於活性層部(半導體層)之有機半導體元件。
作為有機半導體元件之具體例,可列舉:二極體;記憶體;光電二極體、太陽電池、受光元件等光電轉換元件;場效型電晶體、靜電感應型電晶體、雙極電晶體等電晶體;有機EL或發光電晶體等發光元件;溫度感測器、化學感測器、氣體感測器、濕度感測器、放射線感測器、生物感測器、血液感測器、免疫感測器、人造視網膜、味覺感測器、壓力感
測器等感測器類;RFID等邏輯電路單元等,但並不限定於該等。
其中,本發明之化合物作為有機半導體材料具有1cm2/Vs以上之高遷移率,因此對有機電晶體或發光元件之應用尤其有用。
(有機電晶體)
接下來,對含有本發明之化合物之有機電晶體進行說明。
有機電晶體通常係具有源極電極、汲極電極、閘極電極、閘極絕緣層、及有機半導體層而成者,根據各電極或各層之配置而存在各種類型之有機電晶體,但本發明之化合物及有機半導體材料並不限定於有機電晶體之種類,可使用於任意之有機電晶體。關於有機電晶體之種類,可參照Aldrich公司之材料科學之基礎第6號「有機電晶體之基礎」等。
若以圖1所示之底閘極底部接觸型為一例進行詳細說明,則1為基板,2為閘極電極,3為閘極絕緣層,4為有機半導體層,5為源極電極,6為汲極電極。
此處,底閘極底部接觸型(以下稱為BC型)由於在元件製作製程中最後處理關於耐熱性、耐候性或耐溶劑性較其他元件形成用材料(電極材料用金屬或閘極絕緣材料用樹脂)差之有機半導體材料,故而其為更實用之構造。另一方面,BC型與底閘極頂部接觸型(以下稱為TC型)相比,有元件特性較差之傾向(Aldrich公司之材料科學之基礎第6號「有機電晶體之基礎」2.2節)。
本發明之化合物之特徵在於,公知慣用之有機半導體材料用化合物雖然於TC型中顯示高特性,但於BC型中無法再現該特性,相對於此,如下所述,本發明之化合物即便於BC型中亦具有1cm2/Vs以上之高遷移率。
其原因在於,本發明之化合物僅滴加墨水液滴並將其乾燥便以適當之凝聚力形成賦予高遷移率之多晶膜。
基板可使用玻璃或樹脂,為了獲得可撓性之TFT,可使用玻璃製片材、樹脂製片材、塑膠膜等。其中,若使用樹脂製片材或塑膠膜,則除可撓性以外,可實現輕量化,可提高可攜性,並且可提高對於衝擊之耐受性,因此較佳。作為材料,例如可列舉:聚對苯二甲酸乙二酯(PET)、聚萘二甲酸乙二酯(PEN)、聚醚碸(PES)、聚醚醯亞胺、聚醚醚酮、聚苯硫醚、聚芳酯(polyarylate)、聚醯亞胺、聚碳酸酯(PC)、三乙酸纖維素(TAC)、乙酸丙酸纖維素(CAP)等。
閘極電極、源極電極及汲極電極之電極材料只要為導電性材料,則無特別限定,可使用鉑、金、銀、鎳、鉻、銅、鐵、錫、氧化錫、銻、氧化銦錫(ITO)、摻氟氧化鋅、碳、石墨、玻璃石墨、銀漿、碳漿、鋰、鈹、鈉、鎂、鉀、鈣、鈧、鈦、錳、鋯、鎵、鈮、鈉、鈉-鉀合金、鎂、鋰、鋁、鎂/銅混合物、鎂/銀混合物、鎂/鋁混合物、鎂/銦混合物、鋁/氧化鋁混合物、鋰/鋁混合物等。進一步,亦可較佳地使用藉由摻雜等提高導電率之公知慣用之導電性高分子,例如導電性聚苯胺、導電性聚吡咯、導電性聚噻吩、聚伸乙二氧基噻吩與聚苯乙烯磺酸之錯合物(PEDOT/PSS)等。
作為電極之形成方法,有如下方法:使用公知慣用之光刻法或舉離(lift-off)法,將以上述材料作為原料並使用蒸鍍或濺鍍等方法而形成之導電性薄膜於電極進行圖案形成;或於上述導電性薄膜上藉由熱轉印或噴墨等將抗蝕劑進行圖案成膜,然後進行蝕刻。又,可直接藉由噴墨
使導電性高分子之溶液或分散液、或導電性微粒子之分散液圖案化,亦可塗布導電性高分子之溶液或分散液、或導電性微粒子之分散液或漿料,藉由微影法或雷射剝蝕等使如此獲得之塗布膜圖案化。進一步,亦可使用藉由網版印刷法、膠版(off-set)印刷法、凹版膠版印刷法、凸版印刷法、凸版反轉印刷法、微觸印刷法等各種印刷法使導電性高分子之溶液或分散液、或導電性微粒子之分散液或漿料圖案化之方法。
閘極絕緣層可較佳地使用由聚對二甲苯、聚苯乙烯、丙烯酸樹脂、聚酯樹脂等熱塑性樹脂,環氧樹脂、胺酯(urethane)樹脂、酚樹脂、不飽和聚酯樹脂、醇酸樹脂、三聚氰胺樹脂等熱硬化性樹脂,UV硬化性樹脂等所構成之有機薄膜,進一步亦可使用由氧化矽膜等所構成之無機薄膜。
閘極絕緣層例如可藉由旋轉塗布法、滴注法、鑄塗法、浸漬法、模嘴塗布法、刮刀法、線棒塗布法、棒式塗布法、反向塗布法、空氣刀塗法、刮刀塗布法、氣刀塗布法、輥塗法、擠壓式塗布法、含浸塗布法、傳料輥塗布法、接觸塗布法、狹縫式塗布法、噴霧塗布法、靜電塗布法、超音波噴霧塗布法、分注法、噴墨法、網版印刷法、凹版印刷法、膠版印刷法、凹版膠版印刷法、凸版印刷法、凸版反轉印刷法、微觸印刷法等公知慣用之濕式成膜方法而製作,亦可視需要藉由光刻法圖案化成所需之形狀。
有機半導體層可使用本發明之化合物藉由真空蒸鍍法等公知慣用之乾式成膜法而進行成膜,較佳為使用上述本發明之墨水藉由印刷等濕式成膜法而進行成膜。有機半導體層之膜厚並無特別限制,通常為0.5nm~1μm,較佳為2nm~250nm。
又,以提高結晶性且實現半導體特性之提高等為目的,有機半導體層亦可視需要於成膜後實施退火。退火溫度較佳為50~200℃,進一步較佳為70~200℃,時間較佳為10分鐘~12小時,更佳為1小時~10小時,進一步較佳為30分鐘~10小時。
作為成膜方法,例如可列舉:旋轉塗布法、滴注法、鑄塗法、浸漬法、模嘴塗布法、刮刀法、線棒塗布法、棒式塗布法、反向塗布法、空氣刀塗法、刮刀塗布法、氣刀塗布法、輥塗法、擠壓式塗布法、含浸塗布法、傳料輥塗布法、接觸塗布法、狹縫式塗布法、噴霧塗布法、靜電塗布法、超音波噴霧塗布法、分注法、噴墨法、網版印刷法、凹版印刷法、膠版印刷法、凹版膠版印刷法、凸版印刷法、凸版反轉印刷法、微觸印刷法等公知慣用之濕式成膜方法。
本發明之有機電晶體可較佳地用作構成顯示裝置之像素之開關用電晶體、訊號驅動電路元件、記憶體電路元件、訊號處理電路元件等。作為顯示裝置之例,可列舉:液晶顯示裝置、分散型液晶顯示裝置、電泳型顯示裝置、粒子旋轉型顯示元件、電致變色顯示裝置、有機EL顯示裝置、電子紙等。
以下,藉由實施例進一步詳細地說明本發明,但本發明並不限定於該等。
(實施例1)<化合物(1)之製造>
於氬環境下,於2-溴-7-羥基萘80.0g(359mmol)、碳酸鉀149g(1.08mol)中添加乾燥丙酮500mL,並於室溫下進行攪拌。於滴加碘甲烷44.9mL(720mmol)後,回流2小時。將反應混合物冷卻至室溫,添加水250mL。於減壓下將丙酮蒸餾去除,進一步添加水750mL並攪拌10分鐘。過濾所產生之白色沈澱,利用水1.5L將濾集物洗淨。藉由將所獲得之白色固體乾燥而獲得2-溴-7-甲氧基萘71.8g(產率,84.4%)。
1H NMR(300MHz,CDCl3);δ 7.89(d,J=Hz,1H),δ 7.69(d,J=9.3Hz,1H),δ 7.62(s,J=9.0Hz,6H),δ 7.40(d,J=1.8Hz,8.4Hz,1H),δ 7.14(d,J=2.4Hz,9.0Hz,1H),δ 7.02(s,J=2.4Hz,1H).
於氬環境下,於2-溴-7-甲氧基萘5.42g(21.1mmol)、二氯[1,3-雙(二苯基膦基)丙烷]鎳(II)0.259g(1.05mmol)中添加乾燥四氫呋喃20mL,並於-78℃進行攪拌。於對反應液滴加溴化正己基鎂之2M醚溶液11.6mL(23.2mmol)後,慢慢地升溫至室溫。於回流1小時後,冷卻至室溫。對反應液慢慢地滴加水5mL後,以矽藻土過濾將固形物成分
去除。利用硫酸鎂將濾液乾燥,將溶劑蒸餾去除。藉由二氧化矽凝膠管柱層析法(己烷/氯仿=7/3)對所獲得之粗製物進行分離純化,獲得2-己基-7-甲氧基萘4.55g(產率82.1%)。
1H NMR(300MHz,CDCl3);δ 87.70-7.67(m,2H),δ 7.51(s,1H),δ 7.20-7.17(m,1H),δ 7.08-7.06(m,2H),δ 3.91(s,3H),δ 2.74(t,J=7.5Hz,3H),δ 1.75-1.64(m,2H),δ 1.42-1.24(m,6H),δ 0.93-0.86(m,3H).
於氬環境下,於2-己基-7-甲氧基萘4.00g(16.5mmol)中添加乾燥二氯甲烷20mL,並於-78℃進行攪拌。對反應液滴加三溴化硼之1M二氯甲烷溶液28mL(28mmol)後,升溫至室溫並攪拌1小時。於再次冷卻至-78℃之反應液中添加水,使反應停止。添加CH2Cl250mL,進行水洗後,利用硫酸鎂乾燥有機相並將溶劑蒸餾去除,藉此獲得2-己基-7-羥基萘3.53g(產率91.8%)。
1H NMR(300MHz,CDCl3);δ 7.71-7.66(m,2H),δ 7.44(s,1H),δ 7.17(d,J=1.5Hz,8.4Hz,1H),δ 7.08(d,J=2.7Hz,1H),δ 7.02(d,J=2.7Hz,8.7Hz,1H),δ 4.20-4.00(br,1H),δ 3.80(s,3H),δ 2.73(s,J=7.5Hz,2H),δ 1.68-1.62(m,2H),δ 1.41-1.22(m,6H),δ 0.90-0.86(m,3H).
於氬環境下,於2-己基-7-羥基萘1.00g(4.38mmol)、2-萘硫醇0.701g(4.38mmol)、三氟甲磺酸鉍(III)0.144g(0.219mmol)中添加1,2-二氯乙烷8.8mL,並於80℃攪拌16小時。將反應液濃縮,藉由二氧化矽凝膠管柱層析法(環己烷)將所獲得之粗製物分離純化,獲得7-己基-2,2'-聯萘硫醚1.36g(產率83.8%)。
1H NMR(300MHz,CDCl3);δ 7.85-7.72(m,7H),δ 7.47-7.23(m,6H),δ 2.74(t,J=7.4Hz,2H),δ 1.70-1.63(m,2H),δ 1.38-1.28(m,6H),δ 0.88(t,J=6.9Hz,3H).
於7-己基-2,2'-聯萘硫醚0.500g(1.35mmol)、三氟乙酸鈀(II)0.0449g(0.135mmol)、乙酸銀0.901g(5.40mmol)、碳酸鉀0.187g(1.35mmol)中添加三甲基乙酸2.7mL,並於110℃攪拌16小時。利用氯仿稀釋反應液,以矽藻土進行過濾。將濾液濃縮,藉由二氧化矽凝膠管柱層析法(己烷)將所獲得之粗製物分離純化,藉此獲得作為化合物(1)之3-己基二萘并[2,3-b:2',3'-d]噻吩0.280mg(產率55.9%)。
1H NMR(300MHz,CDCl3);δ 8.70(s,1H),δ 8.68(s,1H),δ 8.22(s,1H),δ 8.15(s,1H),δ 8.06-8.03(m,1H),δ 7.98-7.96(m,1H),δ 7.92-7.89(m,1H),δ 7.67(s,1H),δ 7.54-7.51(m,2H),δ
7.38(d,J=1.5Hz,8.4Hz,1H),δ 2.82(t,J=7.2Hz,2H),δ 1.76-1.70(m,2H),δ 1.36-1.24(m,6H),δ 0.90(t,J=6.6Hz,3H).
<有機電晶體之製造>
於玻璃基板(相當於圖1之1)上,使用金屬遮罩藉由真空蒸鍍法將鋁以約30nm之厚度成膜,形成閘極電極(相當於圖1之2)。此處,使用Parylene蒸鍍裝置(laboratory coater PDS2010,日本Parylene製造),以二氯二對二甲苯(DPX-C,日本Parylene製造)為原料,藉由化學氣相沈積(CVD)法製作聚對氯二甲苯(Parylene C)薄膜(厚度500nm)(相當於圖1之3),進一步藉由真空蒸鍍法,將由金薄膜(厚度40nm)所構成之源極、汲極電極進行圖案形成(相當於圖1之5與6,將通道長L(源極電極-汲極電極間隔)設為75μm,將通道寬度W設為5.0mm)。其次,於將如此獲得之基板浸漬於五氟苯硫酚之0.1%乙醇溶液中1小時後,以氮吹送進行乾燥,將上述化合物(1)之0.4%對二甲苯溶液(有機半導體墨水)之液滴0.1μL滴注(滴加)於上述源極、汲極電極之間後,藉由自然濃縮使其乾固,藉此形成由上述化合物(1)所構成之有機半導體層(相當於圖1之4)(藉由有機半導體溶液(墨水)液滴之滴加(滴注)及其乾燥而形成有機半導體層)。
<半導體特性(遷移率)之評價>
針對如此獲得之有機電晶體評價半導體特性(遷移率)。半導體特性(遷移率)係於將源極電極接地、對汲極電極施加-80V之狀態下使用數位萬用表(SMU237,Keithley製造)一面對閘極電極掃描(sweep)施加0至-80V電壓(Vg)一面測定流過汲極電極之電流(Id),根據√Id-Vg之斜率使
用(式1)而求出。單位為cm2/V‧s。
Id=(W/2L).C.μ.(Vg-VT)2 (式1)
(式中,W表示通道寬度,L表示通道長,μ表示遷移率,C表示閘極絕緣層之每單位面積之電容,VT表示閾值電壓)
將評價結果示於表1。
(實施例2)
<化合物(2)之製造>
於實施例1中,將溴化正己基鎂變更為溴化正辛基鎂,除此以外,依據實施例1,獲得化合物(2)(產率64.3%)。
1H NMR(300MHz,CDCl3);δ 8.69(s,1H),δ 8.67(s,1H),δ 8.21(s,1H),δ 8.14(s,1H),δ 8.09-8.04(m,1H),δ 8.03-7.98(m,1H),δ 7.91-7.89(m,1H),δ 7.66(s,1H),δ 7.56-7.48(m,2H),δ 7.38(d,J=1.5Hz,8.4Hz,1H),δ 2.82(t,J=7.2Hz,2H),δ 1.77-1.69(m,2H),δ 1.36-1.24(m,10H),δ 0.88(t,J=6.6Hz,3H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(2)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(實施例3)
<化合物(3)之製造>
於實施例1中,將溴化正己基鎂變更為溴化正癸基鎂,除此以外,依據實施例1,獲得標題化合物(3)(產率53.2%)。
1H NMR(300MHz,CDCl3);δ 8.69(s,1H),δ 8.67(s,1H),δ 8.21(s,1H),δ 8.15(s,1H),δ 8.06-8.03(m,1H),δ 7.99-7.96(m,1H),δ 7.92-7.90(m,1H),δ 7.66(s,1H),δ 7.54-7.49(m,2H),δ 7.38(d,J=1.5Hz,7.8Hz,1H),δ 2.82(t,J=7.8Hz,2H),δ 1.77-1.69(m,2H),δ 1.42-1.18(m,14H),δ 0.88(t,J=6.6Hz,3H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(3)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(實施例4)
<化合物(4)之製造>
於實施例1中,將2-溴-7-羥基萘變更為2-溴-6-羥基萘,除此以外,依據實施例1,獲得化合物(4)(產率44.6%)。
1H NMR(300MHz,CDCl3);δ 8.70(s,1H),δ 8.66(s,1H),δ 8.22(s,1H),δ 8.18(s,1H),δ 8.07-8.04(m,1H),δ 7.92-7.90(m,1H),δ 7.84-7.81(m,2H),δ 7.56-7.49(m,2H),δ 7.40(d,J=1.7Hz,8.3Hz,1H),δ 2.83(t,J=7.2Hz,2H),δ 1.78-1.70(m,2H),δ 1.42-1.28(m,6H),δ 0.90(t,J=6.6Hz,3H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(4)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(實施例5)
<化合物(5)之製造>
於氬環境下,於2-溴-7-羥基萘15.0g(67.2mmol)中添加乾燥DMF60mL,並於0℃進行攪拌。對反應液添加50%氫化鈉9.68g(202mmol)後,於室溫下進行30分鐘攪拌。對反應液添加二甲基胺硫甲醯基氯化物24.9g(202mmol)後,於80℃進行30分鐘攪拌。於反應液中添加甲醇直至發泡停止後,藉由二氧化矽凝膠管柱層析法(己烷/乙酸乙酯=90
/10)進行分離純化,獲得O-(7-溴萘-2-基)N,N-二甲基硫胺甲酸酯7.36g(產率35.3%)。
1H NMR(300MHz,CDCl3);δ 7.96(s,1H),δ 7.82(d,J=8.7Hz,1H),δ 7.71(d,J=8.4Hz,1H),δ 7.53(d,J=1.8Hz,8.7Hz,1H),δ 7.41(d,J=2.4Hz,1H),7.26(d,J=2.4Hz,9.0Hz,1H),δ 3.48(s,3H),δ 3.40(s,3H).
於氬環境下,於O-(7-溴萘-2-基)N,N-二甲基硫胺甲酸酯7.30g(23.5mmol)中添加二苯醚30mL,並於260℃加熱1.5小時。藉由二氧化矽凝膠管柱層析法(己烷/乙酸乙酯=80/20)將反應混合物進行分離而獲得粗製物7.4g。於氬環境下,於粗製物7.4g、氫氧化鉀11.0g(195mmol)中添加甲醇300mL,回流3小時。將溶劑蒸餾去除,於所獲得之油狀液體中添加水300mL並冷卻至0℃後,添加濃鹽酸,對所產生之白色固體進行過濾,並以水500mL洗淨。藉由將所獲得之白色固體乾燥而獲得7-溴-2-萘硫醇5.22g(產率92.8%)。
1H NMR(300MHz,CDCl3);δ 7.84(m,1H),δ 7.73-7.61(m,3H),δ 7.45(d,J=1.8Hz,8.7Hz,1H),δ 7.33(d,J=1.8Hz,8.7Hz,1H),δ 3.62(s,1H).
於氬環境下,於2-己基-7-羥基萘0.202g(0.876mmol)、7-溴-2-萘硫醇0.215g(0.897mmol)、三氟甲磺酸鉍(III)0.0290g(0.044mmol)中添加1,2-二氯乙烷1.7mL,並於80℃攪拌16小時。將反應液進行濃縮,藉由二氧化矽凝膠管柱層析法(環己烷)將所獲得之粗製物進行分離純化,獲得7-溴-7'-己基-2,2'-聯萘硫醚0.306g(產率77.7%)。
1H NMR(300MHz,CDCl3);δ 7.86(s,1H),δ 7.82(d,J=1.8Hz,1H),δ 7.76-7.61(m,5H),δ 7.52-7.46(m,2H),δ 7.40-7.32(m,3H),δ 2.74(t,J=7.5Hz,2H),δ 1.73-1.62(m,2H),δ 1.41-1.25(m,6H),δ 0.88(t,J=6.9Hz,3H).
於7-溴-7'-己基-2,2'-聯萘硫醚2.40g(5.34mmol)、三氟乙酸鈀(II)0.178g(0.534mmol)、乙酸銀(I)3.57g(21.4mmol)、碳酸鉀0.738g(5.34mmol)中添加三甲基乙酸11mL,並於110℃攪拌16小時。利用氯仿稀釋反應液,以矽藻土(Celite)進行過濾。將濾液濃縮,藉由二氧化矽凝膠管柱層析法(己烷)將所獲得之粗製物進行分離純化,獲得3-溴-9-己基二萘并[2,3-b:2',3'-d]噻吩0.603mg(產率25.2%)。
1H NMR(300MHz,CDCl3);δ 8.64(s,1H),δ 8.61(s,1H),δ 8.13(s,1H),δ 8.09(s,1H),δ 8.04(d,J=1.5Hz,1H),δ 7.95(d,J=8.4Hz,1H),δ 7.89(d,J=8.7Hz,1H),δ 7.65(s,1H),δ 7.56(d,J=1.8Hz,9.0Hz,1H),δ 7.38(d,J=1.8Hz,8.4Hz,1H),δ 2.81(t,J=7.5Hz,2H),δ 1.49
-1.68(m,2H),δ 1.38-1.26(m,6H),δ 0.90(t,J=6.9Hz,3H).
於氬環境下,於3-溴-9-己基二萘并[2,3-b:2',3'-d]噻吩0.097g(0.22mmol)、二氯雙(苯甲腈)鈀(II)0.0051g(0.013mmol)、碘化銅(I)0.0017g(0.0089mmol)中添加乾燥THF0.22mL、二異丙基胺0.037mL、三級丁基膦之1.5M甲苯溶液0.019mL(0.029mmol),並於室溫下進行攪拌。對反應液滴加1-乙炔基-4-戊基苯0.046mL(0.27mmol)後,於60℃攪拌8小時。
於反應液中添加CHCl350mL並進行水洗後,利用硫酸鎂對有機相進行乾燥,並將溶劑蒸餾去除。藉由二氧化矽凝膠管柱層析法(環己烷)將所獲得之粗製物分離純化,獲得作為化合物(5)之3-己基-9-((4-戊基苯基)乙炔基)二萘并[2,3-b:2',3'-d]噻吩0.043mg(產率37%)。
1H NMR(300MHz,CDCl3);δ 8.68(s,1H),δ 8.65(s,1H),δ 8.18(s,1H),δ 8.15(s,1H),δ 8.09(s,1H),δ 8.02-7.96(m,2H),δ 7.67(s,1H),δ 7.60(d,J=1.5Hz,8.4Hz,1H),δ 7.51(d,J=8.1Hz,2H),δ 7.39(d,J=1.8Hz,8.4Hz,1H),δ 7.20(d,J=8.1Hz,2H),δ 2.82(t,J=7.2Hz,2H),δ 2.64(t,J=7.8Hz,2H),δ 1.77-1.61(m,4H),δ 1.43-1.27(m,10H),δ 0.93-0.87(m,6H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(5)代替化合物(1),除此以外,以與實施例1同樣之方
式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(實施例6)
<化合物(6)之製造方法>
於實施例5中,將1-乙炔基-4-戊基苯變更為1-乙炔基-4-辛基苯,除此以外,依據實施例5,獲得化合物(6)(產率33%)。
1H NMR(300MHz,CDCl3);δ 8.66(s,1H),δ 8.65(s,1H),δ 8.17(s,1H),δ 8.14(s,1H),δ 8.09(s,1H),δ 8.01-7.95(m,2H),δ 7.66(s,1H),δ 7.61(d,J=1.5Hz,8.5Hz,1H),δ 7.51(d,J=8.1Hz,2H),δ 7.40(d,J=1.8Hz,8.5Hz,1H),δ 7.20(d,J=8.1Hz,2H),δ 2.82(t,J=7.2Hz,2H),δ 2.64(t,J=7.8Hz,2H),δ 1.79-1.58(m,4H),δ 1.43-1.28(m,16H),δ 0.92-0.87(m,6H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(6)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(實施例7)
<化合物(7)之製造方法>
於實施例5中,將1-乙炔基-4-戊基苯變更為2-乙炔基-5-甲基噻吩,除此以外,依據實施例5,獲得化合物(7)(產率36.8%)。
1H NMR(300MHz,CDCl3);δ 8.66(s,1H),δ 8.65(s,1H),δ 8.17(s,1H),δ 8.14(s,1H),δ 8.07(s,1H),δ 8.01-7.96(m,2H),δ 7.67(s,1H),δ 7.57(d,8.4Hz,1H),δ 7.39(d,J=8.4Hz,1H),δ 7.15(d,J=2.4Hz,1H),δ 6.70(d,J=2.4Hz,1H),δ 2.82(t,J=7.5Hz,2H),δ 2.52(s,3H),δ 1.76-1.70(m,2H),δ 1.44-1.28(m,6H),δ 0.93-0.87(m,3H).
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(7)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(比較例1)
<化合物(179)之製造方法>
依照國際公開第2013/125599號說明書所記載之合成方法,獲得通式(179)表示之化合物。
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(179)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
(比較例2)
<化合物(180)之製造方法>
於比較例1中,將2-己基-7-甲氧基萘變更為2-癸基-7-甲氧基萘,除此以外,依據比較例1,獲得通式(180)表示之化合物。
<有機電晶體之製造及半導體特性(遷移率)之評價>
使用化合物(180)代替化合物(1),除此以外,以與實施例1同樣之方式實施有機電晶體之製造、半導體特性(遷移率)之評價。將結果示於表1。
由表1可知,本發明之化合物之溶劑溶解性優異,即便不經由複雜之製程,亦可以簡便之濕式成膜法(即,滴加溶液(墨水)液滴並將其乾燥)形成半導體特性(遷移率)高電晶體。另一方面,比較例1、2所示之公知慣用之化合物無法於此種簡便之成膜法中顯示高遷移率。根據以上可知,本發明之化合物如上所述於實用上具有較佳之性能,優於公知慣用之化合物。因此,可知能夠提供本發明之化合物的本發明之製造方法優於公知慣用之製造方法。
本發明之化合物可用作有機半導體材料,可將本發明之化合物用於用作有機半導體層之有機電晶體。
Claims (13)
- 一種二萘并噻吩衍生物之製造方法,其係通式(D)表示之二萘并噻吩衍生物之製造方法,具有以下之(I)及(II)之步驟:(I)第一步驟:使通式(A)表示之萘酚衍生物與通式(B)表示之萘硫醇衍生物於酸存在下進行脫水縮合而製造通式(C)表示之硫醚衍生物;(II)第二步驟:藉由使該硫醚衍生物(C)於過渡金屬之鹽或過渡金屬之錯合物存在下進行脫氫反應而製造二萘并噻吩衍生物(D);
- 如申請專利範圍第1項之製造方法,其中,該R1~R12為氫原子、非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基(halogeno group)或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基。
- 如申請專利範圍第1或2項之製造方法,其中,關於該R1~R12,R1與R12相互相同或不同,R2與R11相互相同或不同,R3與R10相互相同或不同,R4與R9相互相同或不同,R5與R8相互相同或不同,R6與R7相互相同或不同,但R1與R12、R2與R11、R3與R10、R4與R9、R5與R8、R6與R7此6組組合中之至少一個組合互不相同。
- 一種二萘并噻吩衍生物,其係以通式(E)表示,其中,化合物(E-a)、化合物(E-b)、化合物(E-c)、化合物(E-d)、化合物(E-e)、化合物(E-f)、化合物(E-g)、化合物(E-h)、化合物(E-i)、化合物(E-j)、化合物(E-k)及化合物(E-L)除外,
- 如申請專利範圍第4項之二萘并噻吩衍生物,其中,該R21~R32為氫原子、非環式或環式之碳原子數1~20之烷基(該烷基中之-CH2-可以氧原子、硫原子及氮原子各自不直接鍵結之方式被-O-、-R'C=CR'-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR'-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R'表示碳原子數1~20之非環式或環式烷基))、鹵基、芳香族基(該芳香族基亦可經非環式或環式之碳原子數1~20之烷基、鹵基、芳香族基或腈基取代,該烷基中之-CH2-可以氧原子、 硫原子及氮原子各自不直接鍵結之方式被-O-、-CR"=CR"-、-CO-、-OCO-、-COO-、-S-、-SO2-、-SO-、-NH-、-NR"-或-C≡C-取代,該烷基中之氫原子亦可經芳香族基、鹵基或腈基取代(其中,R"表示碳原子數1~20之非環式或環式烷基))、硝基或腈基。
- 如申請專利範圍第4或5項之二萘并噻吩衍生物,其中,該R21~R32為氫原子、氟原子(氟基)、非環式或環式之碳原子數1~20之烷基、Ph-C≡C*(Ph表示亦可經取代之苯基,*表示鍵結位置)或Th-C≡C*(Th表示亦可經取代之噻吩基,*表示鍵結位置)。
- 如申請專利範圍第4或5項之二萘并噻吩衍生物,其中,該取代基之6組組合(R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27)中之至少一個組合互不相同,且其以外之組合相互相同且為氫原子。
- 如申請專利範圍第4或5項之二萘并噻吩衍生物,其中,該取代基之6組組合(R21與R32、R22與R31、R23與R30、R24與R29、R25與R28、R26與R27)中,R21與R32、R22與R31、R25與R28、R26與R27均相同且為氫原子,R23與R30相互相同或不同,R24與R29相互相同或不同,但R23與R30、R24與R29此2組組合中之至少一個組合互不相同。
- 一種有機半導體材料,其含有申請專利範圍第4至8項中任一項之二萘并噻吩衍生物。
- 一種有機半導體墨水,其含有申請專利範圍第9項之有機半導體材料。
- 一種有機半導體膜,其含有申請專利範圍第9項之有機半導體材料。
- 一種有機半導體元件,其含有申請專利範圍第9項之有機半導體材料。
- 一種有機電晶體,其含有申請專利範圍第9項之有機半導體材料。
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