JP6112269B1 - 有機化合物、その製造法、それを含有する有機半導体材料及びそれを含有する有機トランジスタ - Google Patents
有機化合物、その製造法、それを含有する有機半導体材料及びそれを含有する有機トランジスタ Download PDFInfo
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- JP6112269B1 JP6112269B1 JP2016562033A JP2016562033A JP6112269B1 JP 6112269 B1 JP6112269 B1 JP 6112269B1 JP 2016562033 A JP2016562033 A JP 2016562033A JP 2016562033 A JP2016562033 A JP 2016562033A JP 6112269 B1 JP6112269 B1 JP 6112269B1
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- 239000004065 semiconductor Substances 0.000 title claims abstract description 105
- 238000000034 method Methods 0.000 title claims abstract description 76
- 239000000463 material Substances 0.000 title claims abstract description 43
- 230000008569 process Effects 0.000 title claims abstract description 7
- 150000002894 organic compounds Chemical class 0.000 title 1
- -1 transition metal salt Chemical class 0.000 claims abstract description 192
- 150000001875 compounds Chemical class 0.000 claims abstract description 120
- 238000004519 manufacturing process Methods 0.000 claims abstract description 45
- 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 40
- 239000002253 acid Substances 0.000 claims abstract description 29
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 22
- 150000003568 thioethers Chemical class 0.000 claims abstract description 13
- 150000003624 transition metals Chemical class 0.000 claims abstract description 12
- 238000006356 dehydrogenation reaction Methods 0.000 claims abstract description 9
- 150000004780 naphthols Chemical class 0.000 claims abstract description 8
- SEXOVMIIVBKGGM-UHFFFAOYSA-N naphthalene-1-thiol Chemical class C1=CC=C2C(S)=CC=CC2=C1 SEXOVMIIVBKGGM-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 31
- 125000003118 aryl group Chemical group 0.000 claims description 31
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 23
- 125000002560 nitrile group Chemical group 0.000 claims description 21
- 125000002015 acyclic group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 125000004434 sulfur atom Chemical group 0.000 claims description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 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
- 101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
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- 230000018044 dehydration Effects 0.000 claims 1
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- 239000001488 sodium phosphate Substances 0.000 description 12
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- 239000010409 thin film Substances 0.000 description 11
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 10
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 238000007639 printing Methods 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 239000012043 crude product Substances 0.000 description 8
- 229910052760 oxygen Inorganic materials 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- 229910052709 silver Inorganic materials 0.000 description 8
- 239000004332 silver Substances 0.000 description 8
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 8
- XTHPWXDJESJLNJ-UHFFFAOYSA-N sulfurochloridic acid Chemical compound OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 8
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 8
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 8
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 229910052782 aluminium Inorganic materials 0.000 description 7
- 150000001721 carbon Chemical group 0.000 description 7
- 238000005266 casting Methods 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical class [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- CQLFBEKRDQMJLZ-UHFFFAOYSA-M silver acetate Chemical compound [Ag+].CC([O-])=O CQLFBEKRDQMJLZ-UHFFFAOYSA-M 0.000 description 7
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- 239000000758 substrate Substances 0.000 description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 6
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
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- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 6
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
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- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 6
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- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 6
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 6
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- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
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- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 6
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- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 6
- 235000019260 propionic acid Nutrition 0.000 description 6
- 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
- 230000009257 reactivity Effects 0.000 description 6
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- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
- 238000001771 vacuum deposition Methods 0.000 description 6
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 6
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- AKEXVWKYUAMNKL-UHFFFAOYSA-N 2,2-dimethylpropanoic acid;silver Chemical compound [Ag].CC(C)(C)C(O)=O AKEXVWKYUAMNKL-UHFFFAOYSA-N 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 239000003570 air Substances 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000004414 alkyl thio group Chemical group 0.000 description 5
- NYENCOMLZDQKNH-UHFFFAOYSA-K bis(trifluoromethylsulfonyloxy)bismuthanyl trifluoromethanesulfonate Chemical compound [Bi+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F NYENCOMLZDQKNH-UHFFFAOYSA-K 0.000 description 5
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 125000004122 cyclic group Chemical group 0.000 description 5
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- SHXXPRJOPFJRHA-UHFFFAOYSA-K iron(iii) fluoride Chemical compound F[Fe](F)F SHXXPRJOPFJRHA-UHFFFAOYSA-K 0.000 description 5
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- LMEWRZSPCQHBOB-UHFFFAOYSA-M silver;2-hydroxypropanoate Chemical compound [Ag+].CC(O)C([O-])=O LMEWRZSPCQHBOB-UHFFFAOYSA-M 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- REHQLKUNRPCYEW-UHFFFAOYSA-N 1-methylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1(C)CCCCC1 REHQLKUNRPCYEW-UHFFFAOYSA-N 0.000 description 4
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- RILOPSTZZRJOQI-UHFFFAOYSA-N 4-cyclohexylbutanoic acid;silver Chemical compound [Ag].OC(=O)CCCC1CCCCC1 RILOPSTZZRJOQI-UHFFFAOYSA-N 0.000 description 4
- CMWINYFJZCARON-UHFFFAOYSA-N 6-chloro-2-(4-iodophenyl)imidazo[1,2-b]pyridazine Chemical compound C=1N2N=C(Cl)C=CC2=NC=1C1=CC=C(I)C=C1 CMWINYFJZCARON-UHFFFAOYSA-N 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 239000005696 Diammonium phosphate Substances 0.000 description 4
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical compound [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
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- GUBFQUUXGNHDPZ-UHFFFAOYSA-K scandium(3+);2,2,2-trifluoroacetate Chemical compound [Sc+3].[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F.[O-]C(=O)C(F)(F)F GUBFQUUXGNHDPZ-UHFFFAOYSA-K 0.000 description 1
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- 125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 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
- 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
- 125000001425 triazolyl group Chemical group 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 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
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- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
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- 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 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
- LSWWNKUULMMMIL-UHFFFAOYSA-J zirconium(iv) bromide Chemical compound Br[Zr](Br)(Br)Br LSWWNKUULMMMIL-UHFFFAOYSA-J 0.000 description 1
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Classifications
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- 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
-
- 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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Abstract
Description
更に、これら有機半導体材料には、当初「シリコン半導体材料に比べて、半導体特性(移動度)が低く、そのため、トランジスタの応答速度が遅くなり、実用化は難しい」といった課題があったが、近年、アモルファスシリコンの移動度を凌駕する材料が開発され始めている。
1.一般式(D)で表されるジナフトチオフェン誘導体の製造方法であって、以下の(I)及び(II)の工程を有するジナフトチオフェン誘導体の製造方法、
((I)一般式(A)で表されるナフトール誘導体と一般式(B)で表されるナフタレンチオール誘導体を、酸存在下、脱水縮合させて一般式(C)で表されるスルフィド誘導体を製造する第一工程、
(II)前記スルフィド誘導体(C)を、遷移金属の塩又は遷移金属の錯体存在下、脱水素化反応によりジナフトチオフェン誘導体(D)を製造する第二工程。)
2.前記R1〜R12が、水素原子、非環式又は環式の炭素原子数1〜20のアルキル基(当該アルキル基中の−CH2−が、酸素原子、硫黄原子および窒素原子が各々直接結合しないように、−O−、−R’C=CR’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’は炭素原子数1〜20の非環式又は環式アルキル基を表す。)。)、ハロゲノ基、芳香族基(当該芳香族基は、非環式又は環式の炭素原子数1〜20のアルキル基、ハロゲノ基、芳香族基、又はニトリル基で置換されていてもよく、当該アルキル基中の−CH2−が、酸素原子、硫黄原子および窒素原子が各々直接結合しないように、−O−、−CR’’=CR’’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’’は炭素原子数1〜20の非環式又は環式アルキル基を表す。)。)、ニトロ基、又はニトリル基である、1.に記載の製造方法、
3.前記R1〜R12について、R1とR12は互いに同じであるか異なり、R2とR11は互いに同じであるか異なり、R3とR10は互いに同じであるか異なり、R4とR9は互いに同じであるか異なり、R5とR8は互いに同じであるか異なり、R6とR7は互いに同じであるか異なるが、R1とR12、R2とR11、R3とR10、R4とR9、R5とR8、R6とR7、の6組の組み合わせのうち、少なくとも一つの組み合わせは互いに異なる、1.又は2.に記載の製造方法、
4.一般式(E)で表されるジナフトチオフェン誘導体(ただし、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)、および化合物(E−L)を除く。)、
5.前記R21〜R32が、水素原子、非環式又は環式の炭素原子数1〜20のアルキル基(当該アルキル基中の−CH2−が、酸素原子、硫黄原子および窒素原子が各々直接結合しないように、−O−、−R’C=CR’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’は炭素原子数1〜20の非環式又は環式アルキル基を表す。)。)、ハロゲノ基、芳香族基(当該芳香族基は、非環式又は環式の炭素原子数1〜20のアルキル基、ハロゲノ基、芳香族基、又はニトリル基で置換されていてもよく、当該アルキル基中の−CH2−が、酸素原子、硫黄原子および窒素原子が各々直接結合しないように、−O−、−CR’’=CR’’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’’は炭素原子数1〜20の非環式又は環式アルキル基を表す。)。)、ニトロ基、又はニトリル基である4.に記載のジナフトチオフェン誘導体、
6.前記R21〜R32が、水素原子、フッ素原子(フルオロ基)、非環式又は環式の炭素原子数1〜20のアルキル基、Ph−C≡C*(Phは置換されていてもよいフェニル基、*は結合位置を表す。)、またはTh−C≡C*(Thは置換されていてもよいチエニル基、*は結合位置を表す。)である、4.または5.に記載のジナフトチオフェン誘導体、
7.前記した置換基に係わる6組の組み合わせ(R21とR32、R22とR31、R23とR30、R24とR29、R25とR28、R26とR27)のうち、少なくとも一つの組み合わせは互いに異なり、且つ、それ以外の組み合わせは互いに同一で水素原子である、4.〜6.に記載のジナフトチオフェン誘導体、
8.前記した置換基に係わる6組の組み合わせ(R21とR32、R22とR31、R23とR30、R24とR29、R25とR28、R26とR27)のうち、R21とR32、R22とR31、R25とR28、R26とR27、はいずれも同一で水素原子であり、R23とR30は互いに同じであるか異なり、R24とR29は互いに同じであるか異なるが、R23とR30、R24とR29、の2組の組み合わせのうち、少なくとも一つの組み合わせは互いに異なる、4.〜6.に記載のジナフトチオフェン誘導体、
9.4.〜8.のいずれかに記載のジナフトチオフェン誘導体を含有する有機半導体材料、
10.9.に記載の有機半導体材料を含有する有機半導体インク、
11.9.に記載の有機半導体材料を含有する有機半導体膜、
12.9.に記載の有機半導体材料を含有する有機半導体素子、
13.9.に記載の有機半導体材料を含有する有機トランジスタ。
本発明のジナフトチオフェン誘導体の製造方法について説明する。
本発明の製造法のスキームは次の通りである。
ここで、本発明の製造法に係わる一般式(A)、(B)、(C)、(D)で表せる化合物の置換基R1〜R12は、同一でも異なっていてもよく、芳香族化合物の置換基として公知慣用の任意の置換基(但し、後記する製造工程(I)又は(II)において反応活性部とならない置換基)を用いることが出来る。その具体例としては、
水素原子(軽水素、重水素及び三重水素を含む)、
非環式又は環式の炭素原子数1〜20のアルキル基(該アルキル基中の−CH2−が、酸素原子、硫黄原子及び窒素原子が各々直接結合しないように、−O−、−R’C=CR’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’は炭素原子数1〜20の非環式又は環式アルキル基を表す。))、
ハロゲノ基、芳香族基(該芳香族基は、非環式又は環式の炭素原子数1〜20のアルキル基、ハロゲノ基、芳香族基、又はニトリル基で置換されていてもよく、該アルキル基中の−CH2−が、酸素原子、硫黄原子及び窒素原子が各々直接結合しないように、−O−、−CR’’=CR’’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’’は炭素原子数1〜20の非環式又は環式アルキル基を表す。))、
ニトロ基、又はニトリル基、等を挙げることが出来るが、これらに限定されるものではない。なお、前記アルキル基、ハロゲノ基、芳香族基の具体例としては、後記する本発明の化合物(ジナフトチオフェン誘導体)の置換基と同様のものを挙げることが出来る。
(I)一般式(A)で表せるナフトール誘導体と一般式(B)で表せるナフタレンチオール誘導体を、酸存在下、脱水縮合させて一般式(C)で表せるスルフィド誘導体を製造する第一工程と、
(II)前記スルフィド誘導体(C)を、遷移金属の塩又は遷移金属の錯体存在下、脱水素化反応によりジナフトチオフェン誘導体(D)を製造する第二工程、
よりなることを特徴とする。
ナフタレンチオール誘導体(B)は、市販されているものも多く入手も容易である。またEuropean Journal of Organic Chemistry 833-845 (2010)などに記載されている、ナフトールをジメチルチオカルバモイルクロリドと縮合させてO−チオカルバマートとした後、S−チオカルバマートに熱転位させ、最後に加水分解する方法に従って、合成することも可能である。
塩酸、臭化水素酸、ヨウ化水素酸、過塩素酸、硝酸、硫酸、燐酸、ホウ酸、ポリ燐酸、フルオロ硫酸、クロロ硫酸、リンタングステン酸等のヘテロポリ酸等が挙げられる。
前記鉱酸中、塩酸、硝酸、硫酸、燐酸、ポリ燐酸、フルオロ硫酸、クロロ硫酸が好ましく、より反応性を向上させるためには、硫酸、リン酸、ポリリン酸、フルオロ硫酸が更に好ましい。
メタンスルホン酸、エタンスルホン酸、プロパンスルホン酸、ブタンスルホン酸、ペンタンスルホン酸、ヘキサンスルホン酸、ヘプタンスルホン酸、オクタンスルホン酸、ノナンスルホン酸、デカンスルホン酸等のアルキルスルホン酸;
トリフルオロメタンスルホン酸、ペルフルオロエタンスルホン酸、ペルフルオロプロパンスルホン酸、ペルフルオロブタンスルホン酸、ペルフルオロペンタンスルホン酸、ペルフルオロヘキサンスルホン酸、ペルフルオロヘプタンスルホン酸、ペルフルオロオクタンスルホン酸、ペルフルオロノナンスルホン酸、ペルフルオロデカンスルホン酸等のフッ素化アルキルスルホン酸;
ベンゼンスルホン酸、ナフタレンスルホン酸、ピリジンスルホン酸、チオフェンスルホン酸、p−トルエンスルホン酸、p−スチレンスルホン酸、キシレンスルホン酸等のアルキル置換でされていても良いアリールスルホン酸;
等が挙げられる。
より反応性を向上させるためには、メタンスルホン酸、エタンスルホン酸、トリフルオロメタンスルホン酸、ペルフルオロエタンスルホン酸、ペルフルオロプロパンスルホン酸、ペルフルオロブタンスルホン酸が更に好ましい。
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等の元素又はPO、SeO、VO等の酸素−元素結合体と、
フッ化水素、塩化水素、臭化水素酸、ヨウ化水素、過塩素酸、硝酸、硫酸、リン酸、フルオロ硫酸、クロロ硫酸、テトラフルオロホウ酸、ヘキサフルオロリン酸等の鉱酸、アルキルスルホン酸、ハロゲン化されていてもよいアルキルスルホン酸、アリールスルホン酸、アルキル側鎖を有していてもよいアリールスルホン酸、ホスホン酸、カルボン酸、ハロゲン化されていてもよいカルボン酸等の酸性化合物との塩又は錯体であり、
三フッ化ホウ素、三塩化ホウ素、三フッ化ホウ素ジエチルエーテル錯体、三フッ化ホウ素ジメチルスルフィド錯体、
フッ化アルミニウム、塩化アルミニウム、臭化アルミニウム、過塩素酸アルミニウム、硝酸アルミニウム、硫酸アルミニウム、メタンスルホン酸アルミニウム、トリフルオロメタンスルホン酸アルミニウム、p−トルエンスルホン酸アルミニウム、酢酸アルミニウム、トリフルオロ酢酸アルミニウム等のアルミニウムの塩又は錯体;
フッ化スカンジウム(III)、塩化スカンジウム(III)、臭化スカンジウム(III)、過塩素酸スカンジウム(III)、硝酸スカンジウム(III)、硫酸スカンジウム(III)、メタンスルホン酸スカンジウム(III)、トリフルオロメタンスルホン酸スカンジウム(III)、p−トルエンスルホン酸スカンジウム(III)、酢酸スカンジウム(III)、トリフルオロ酢酸スカンジウム(III)等のスカンジウム(III)の塩又は錯体;
フッ化鉄(III)、塩化鉄(III)、臭化鉄(III)、過塩素酸鉄(III)、硝酸鉄(III)、硫酸鉄(III)、メタンスルホン酸鉄(III)、トリフルオロメタンスルホン酸鉄(III)、p−トルエンスルホン酸鉄(III)、酢酸鉄(III)、トリフルオロ酢酸鉄(III)等の鉄(III)の塩又は錯体;
フッ化亜鉛、塩化亜鉛、臭化亜鉛、過塩素酸亜鉛、硝酸亜鉛、硫酸亜鉛、メタンスルホン酸亜鉛、トリフルオロメタンスルホン酸亜鉛、p−トルエンスルホン酸亜鉛、酢酸亜鉛、トリフルオロ酢酸亜鉛等の亜鉛(II)の塩又は錯体;
フッ化ジルコニウム(IV)、塩化ジルコニウム(IV)、臭化ジルコニウム(IV)、過塩素酸ジルコニウム(IV)、硝酸ジルコニウム(IV)、硫酸ジルコニウム(IV)、メタンスルホン酸ジルコニウム(IV)、トリフルオロメタンスルホン酸ジルコニウム(IV)、p−トルエンスルホン酸ジルコニウム(IV)、酢酸ジルコニウム(IV)、トリフルオロ酢酸ジルコニウム(IV)等のジルコニウム(IV)の塩又は錯体;
フッ化ビスマス(III)、塩化ビスマス(III)、臭化ビスマス(III)、過塩素酸ビスマス(III)、硝酸ビスマス(III)、硫酸ビスマス(III)、メタンスルホン酸ビスマス(III)、トリフルオロメタンスルホン酸ビスマス(III)、p−トルエンスルホン酸ビスマス(III)、酢酸ビスマス(III)、トリフルオロ酢酸ビスマス(III)等のビスマス(III)の塩又は錯体;
塩化スズ(IV)、塩化アンチモン(V)、塩化テルル(IV)、臭化テルル(IV)、塩化モリブデン(VI)、四塩化チタン(IV)、四塩化バナジウム(IV)等が挙げられる。
三フッ化ホウ素、三塩化ホウ素、三フッ化ホウ素ジエチルエーテル錯体、三フッ化ホウ素ジメチルスルフィド錯体、フッ化アルミニウム、塩化アルミニウム、臭化アルミニウム、過塩素酸アルミニウム、硝酸アルミニウム、硫酸アルミニウム、メタンスルホン酸アルミニウム、トリフルオロメタンスルホン酸アルミニウム、p−トルエンスルホン酸アルミニウム、酢酸アルミニウム、トリフルオロ酢酸アルミニウム、フッ化鉄(III)、塩化鉄(III)、臭化鉄(III)、過塩素酸鉄(III)、硝酸鉄(III)、硫酸鉄(III)、メタンスルホン酸鉄(III)、トリフルオロメタンスルホン酸鉄(III)、p−トルエンスルホン酸鉄(III)、酢酸鉄(III)、トリフルオロ酢酸鉄(III)、フッ化亜鉛、塩化亜鉛、臭化亜鉛、過塩素酸亜鉛、硝酸亜鉛、硫酸亜鉛、メタンスルホン酸亜鉛、トリフルオロメタンスルホン酸亜鉛、p−トルエンスルホン酸亜鉛、酢酸亜鉛、トリフルオロ酢酸亜鉛、フッ化インジウム(III)、塩化インジウム(III)、臭化インジウム(III)、過塩素酸インジウム(III)、硝酸インジウム(III)、硫酸インジウム(III)、メタンスルホン酸インジウム(III)、トリフルオロメタンスルホン酸インジウム(III)、p−トルエンスルホン酸インジウム(III)、酢酸インジウム(III)、トリフルオロ酢酸インジウム(III)、フッ化ビスマス(III)、塩化ビスマス(III)、臭化ビスマス(III)、過塩素酸ビスマス(III)、硝酸ビスマス(III)、硫酸ビスマス(III)、メタンスルホン酸ビスマス(III)、トリフルオロメタンスルホン酸ビスマス(III)、p−トルエンスルホン酸ビスマス(III)、酢酸ビスマス(III)、トリフルオロ酢酸ビスマス(III)、塩化スズ(IV)、塩化モリブデン(VI)が好ましい。
シリカ、α−アルミナ等の酸化物;
シリカアルミナ、シリカチタニア、ゼオライト、アルミナチタニア、チタニア酸化亜鉛、シリカ酸化亜鉛、チタニアジルコニア 、シリカモリブデン等の非晶質又は結晶質複合系金属酸化物;
液体リン酸触媒等の液体酸を無機質担体に吸着固定化した固定化酸;
等である。
シリカアルミナ、シリカチタニア、ゼオライトが好ましい。
これらの固体酸触媒の大きさ、形状等は特に限定するものではないが、通常、粉粒状のものが使用され、その粒径は好ましくは10μm〜10mmである。特に反応効率を上げるため、多孔質で実質表面積(反応液接触面積)の大きなものが好ましい。
これらの酸触媒は単独で又は2種以上組み合わせて使用出来、その使用量はナフトール誘導体(A)に対し0.001〜10当量、好ましくは0.005〜5当量、より好ましくは0.01〜2.5当量である。
酢酸エチル、酢酸イソプロピル、酢酸アミル等のエステル溶媒;
n−ヘキサン、ヘプタン、オクタン、シクロヘキサン、シクロペンタン等の脂肪族炭化水素溶媒;
ジクロロメタン、クロロホルム、四塩化炭素、1,2−ジクロロエタン等のハロゲン系溶媒;
トルエン、ベンゼン、キシレン等の芳香族炭化水素溶媒;
N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロジノン等のアミド溶媒;
ジメチルスルホキシド、スルホラン等の含硫黄溶媒;
アセトニトリル、バレロニトリル、ベンゾニトリル等のニトリル溶媒;
酢酸、プロピオン酸、酪酸等のカルボン酸溶媒;
等を挙げることが出来、これらの溶媒は、単独で又は2種以上組み合わせて使用出来る。
該反応で用いられる遷移金属とは、第一遷移元素であるScからZnまで、第二遷移元素であるYからCdまで、及び第三遷移元素であるLaからHgまでの金属である。
前記の遷移金属中、
鉄、コバルト、ニッケル、銅、モリブデン、ルテニウム、ロジウム、パラジウム、オスミウム、イリジウム、白金、金が好ましく、
より反応性を向上させるためには、
ニッケル、モリブデン、ルテニウム、ロジウム、パラジウム、イリジウム、白金、金であることが更に好ましく、
より一層反応性を向上させるためには、ルテニウム、パラジウム、白金であることが特に好ましい。
水、フッ化水素、塩化水素、臭化水素酸、ヨウ化水素、過塩素酸、硝酸、硫酸、リン酸、フルオロ硫酸、クロロ硫酸、テトラフルオロホウ酸、ヘキサフルオロリン酸、リンタングステン酸等のヘテロポリ酸、アルキルスルホン酸、ハロゲン化されていてもよいアルキルスルホン酸、アリールスルホン酸、アルキル側鎖を有していてもよいアリールスルホン酸、ホスホン酸、カルボン酸、ハロゲン化されていてもよいカルボン酸等の酸性化合物;
アルケン、アルキン、アミン、ホスフィン、アルシン、N−ヘテロサイクリックカルベン、ジベンジリデンアセトン、アセチルアセトン、一酸化炭素、ニトリル、サレン等の配位子;
との塩又は錯体が挙げられる。
テトラキス(トリフェニルホスフィン)パラジウム(0)、トリス(ジベンジリデンアセトン)ジパラジウム(0)、ビス(ジベンジリデンアセトン)パラジウム(0)、ビス[1,2−ビス(ジフェニルホスフィノ)エタン]パラジウム(0)、ビス(トリ−t−ブチルホスフィン)パラジウム(0)、ビス(トリシクロヘキシルホスフィン)パラジウム(0)、ビス[ジ−tert−ブチル(4−ジメチルアミノフェニル)ホスフィン]パラジウム(0)、水酸化パラジウム(II)、硝酸パラジウム(II)、ジクロロベンジルビス(トリフェニルホスフィン)パラジウム(II)、ジクロロビス(トリフェニルホスフィン)パラジウム(II)、クロロアリルパラジウム(II)ダイマー、ジクロロビス(アセトニトリル)パラジウム(II)、ジクロロビス(ベンゾニトリル)パラジウム(II)、酢酸ビス(トリフェニルホスフィン)パラジウム(II)、トリフルオロ酢酸ビス(トリフェニルホスフィン)パラジウム(II)、ジクロロ(cis,cis−1,5−シクロオクタンジエン)パラジウム(II)、酢酸パラジウム(II)、トリフルオロ酢酸パラジウム(II)、ピバル酸パラジウム(II)、ビス(トリフルオロメタンスルホン酸)テトラキス(アセトニトリル)パラジウム(II)、アセチルアセトンパラジウム(II)、塩化パラジウム(II)、臭化パラジウム(II)、テトラクロロパラジウム(II)酸ナトリウム、ジクロロ2,5−ノルボルナジエンパラジウム(II)、硝酸(エチレンジアミン)パラジウム(II)、ジクロロ[9,9−ジメチル−4,5−ビス(ジフェニルホスフィノ)キサンテン]パラジウム(II)、ジクロロ(1,5−シクロオクタジエン)パラジウム(II)、ジ−μ−クロロビス[5−ヒドロキシ−2−[1−(ヒドロキシイミノ)エチル]フェニル]パラジウム(II)ダイマー、ジクロロ[ジ−tert−ブチル(クロロ)ホスフィン]パラジウム(II)ダイマー、クロロ[(トリ−tert−ブチルホスフィン)−2−(2−アミノビフェニル)]パラジウム(II)、ジクロロビス(トリ−o−トリルホスフィン)パラジウム(II)、ジクロロビス(メチルジフェニルホスフィン)パラジウム(II)、パラジウム/炭素、パラジウム/アルミナ、パラジウム/炭酸バリウム、パラジウム/硫酸バリウム等のパラジウム塩又は錯体;
テトラキス(トリフェニルホスフィン)白金(0)、ビス(トリ−tert−ブチルホスフィン)白金(0)、塩化白金(II)、アセチルアセトン白金(II)、cis−ジアミン(1,1−シクロブタンジカルボキシラト)白金(II)、ジクロロcis−ジアンミン白金(II)、ジクロロ(1,5−シクロオクタジエン)白金(II)、(trans−1,2−シクロヘキサンジアミン)オキサラト白金(II)等の白金塩又は錯体が挙げられる。
配位子としては例えば、トリメチルホスフィン、トリエチルホスフィン、トリ−n−ブチル)ホスフィン、トリ−tert−ブチルホスフィン、トリシクロヘキシルホスフィン、トリフェニルホスフィン、トリ(o−トリル)ホスフィン等の単座ホスフィン系配位子;ビス(ジフェニルホスフィノ)メタン、1,2−ビス(ジフェニルホスフィノ)エタン、2,2’−ビス(ジフェニルホスフィノ)−1,1’−ビナフタレン、1,1’−ビス(ジフェニルホスフィノ)フェロセン等の二座ホスフィン系配位子;
等が挙げられる。
酸化剤としては例えば、過酢酸、過酸化水素、過酸化水素水、尿素・過酸化水素、Oxone、過炭酸ナトリウム、過ホウ酸ナトリウム、過ホウ酸カリウム、ぺルオキソ二硫酸ジカリウム、過硫酸テトラブチルアンモニウム、3−クロロ過安息香酸、ジメチルジオキシラン、tert−ブチルヒドロペルオキシド、過酸化ベンゾイル等の過酸化物;
酸素、オゾン、フッ素、塩素、臭素、一酸化窒素、一酸化二窒素等の酸化性ガス;
三酸化クロム、二酸化マンガン、酢酸マンガン(III)、過マンガン酸カリウム、二クロム酸カリウム、五酸化二バナジウム(V)、トリイソプロポキシバナジウム(V)オキシド、硝酸セリウム(IV)アンモニウム、酢酸鉛(IV)、酸化オスミニウム(VIII)等の高酸化度金属化合物;、
フッ化銀、塩化銀、臭化銀、ヨウ化銀、酸化銀、炭酸銀、シアン化銀、硫酸銀、硝酸銀、酢酸銀、トリフルオロ酢酸銀、ピバル酸銀、乳酸銀、シクロヘキサン酪酸銀、メタンスルホン銀、トリフルオロメタンスルホン酸銀、テトラフルオロほう酸銀等の銀(I)化合物、
フッ化鉄(II)、塩化鉄(II)、臭化鉄(II)、ヨウ化鉄(II)、酸化鉄(II)、炭酸鉄(II)、シアン化鉄(II)、硫酸鉄(II)、硝酸鉄(II)、酢酸鉄(II)、トリフルオロ酢酸鉄(II)、ピバル酸鉄(II)、乳酸鉄(II)、シクロヘキサン酪酸鉄(II)、メタンスルホン鉄(II)、トリフルオロメタンスルホン酸鉄(II)、テトラフルオロほう酸鉄(II)等の鉄(II)化合物;
ベンゾキノン、アントラキノン、2−(シクロヘキシルスルフィニル)−ベンゾキノン、2−(フェニルスルフィニル)−ベンゾキノン、2,3−ジクロロ−5,6−ジシアノ−1,4−ベンゾキノン、クロラニル、o−クロラニル等のキノン誘導体;
等が挙げられ、
更により好ましくは、酸素、硝酸銀、酢酸銀、トリフルオロ酢酸銀、ピバル酸銀、乳酸銀、シクロヘキサン酪酸銀、メタンスルホン銀、トリフルオロメタンスルホン酸銀、テトラフルオロほう酸銀、
カルボン酸としては例えば、ギ酸、酢酸、プロピオン酸、酪酸、吉草酸、カプロン酸、エナント酸、カプリル酸、ペラルゴン酸、カプリン酸、ラウリン酸、ミリスチン酸、パルミチン酸、マルガリン酸、ステアリン酸、ピバル酸、2,2-ジメチル酪酸、1-メチル-1-シクロヘキサンカルボン酸、2-フェニルイソ酪酸等の飽和脂肪族カルボン酸;
オレイン酸、リノール酸、リノレン酸、アラキドン酸、エイコサペンタエン酸等の不飽和脂肪族カルボン酸;
安息香酸、フタル酸、イソフタル酸、テレフタル酸、サリチル酸、没食子酸、メリト酸、ケイ皮酸等の芳香族カルボン酸;
シュウ酸、マレイン酸、フマル酸、コハク酸、グルタル酸、ムコン酸、アジピン酸、アゼライン酸、2,5−チオフェンジカルボン酸、テレフタル酸、2,5−ピラジンジカルボン酸、ナフタレン−2,6−ジカルボン酸、ビフェニル−4,4’−ジカルボン酸、アゾベンゼンジカルボン酸、ベンゼン−1,2,4−トリカルボン酸、ベンゼン−1,3,5−トリ安息香酸)、ベンゼン−1,2,4,5−テトラカルボン酸、ナフタレン−2,3,6,7−テトラカルボン酸、ナフタレン−1,4,5,8−テトラカルボン酸、ビフェニル−3,5,3’,5’−テトラカルボン酸、及び2−アミノテレフタル酸、2−ニトロテレフタル酸、2−メチルテレフタル酸、2−クロロテレフタル酸、2−ブロモテレフタル酸、2,5−ジヒドロオキソテレフタル酸、テトラフルオロテレフタル酸、2,5−ジカルボキシテレフタル酸、ジメチル−4,4’−ビフェニルジカルボン酸、テトラメチル−4,4’−ビフェニルジカルボン酸、ジカルボキシ−4,4’−ビフェニルジカルボン酸、2,5−ピラジンジカルボン酸、2,5−ジペルフルオロテレフタル酸、アゾベンゼン−4,4’−ジカルボン酸、3,3’−ジクロロアゾベンゼン−4,4’−ジカルボン酸、3,3’−ジヒドロオキソアゾベンゼン−4,4’−ジカルボン酸、3,3’−ジペルフルオロアゾベンゼン−4,4’−ジカルボン酸、3,5,3’,5’−アゾベンゼンテトラカルボン酸、2,5−ジメチルテレフタル酸等の多価カルボン酸;
が挙げられ、
更により一層好ましくは、酢酸、プロピオン酸、ピバル酸、2,2−ジメチル酪酸、1−メチル-1-シクロヘキサンカルボン酸、トリフルオロ酢酸、トリクロロ酢酸、
である。
塩基としては例えば、炭酸ナトリウム、炭酸カリウム、炭酸セシウム等の炭酸塩;
リン酸ナトリウム、リン酸二ナトリウム、リン酸三ナトリウム、リン酸カリウム、リン酸カルシウム、リン酸二アンモニウム等のリン酸塩;
水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム等の水酸化物、フッ化カリウム、フッ化セシウム、テトラブチルアンモニウムフルオリド等のフッ化物;
ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert−ブトキシド等のアルコキシド;
トリメチルアミン、トリエチルアミン、トリブチルアミン、ジイソプロピルエチルアミン、N−メチルモルホリン、N−メチルピロリジン、N−メチルピペリジン、1,8−ジアザ−ビシクロ[5.4.0]ウンデカ−7−エン、1,4−ジアザ−ビシクロ[2.2.2]オクタン等の第3級アミン;
ピリジン、ピコリン、エチルピリジン、プロピルピリジン、ブチルピリジン、t−ブチルピリジンのような2,3−ジメチルピリジン、2,4−ジメチルピリジン、2,5−ジメチルピリジン、2,6−ジメチルピリジン、3,5−ジメチルピリジン、2−メチル−5−エチル−ピリジン、2,6−ジイソプロピルピリジン、2,6−ジtーブチルピリジン等のピリジン誘導体;
が挙げられ、
フッ化カリウム、フッ化セシウム、テトラブチルアンモニウムフルオリド等のフッ化物、ナトリウムメトキシド、ナトリウムエトキシド、カリウムtert−ブトキシド、
特に好ましくは、炭酸ナトリウム、炭酸カリウム、炭酸セシウム、
リン酸ナトリウム、リン酸二ナトリウム、リン酸三ナトリウム、リン酸カリウム、リン酸カルシウム、リン酸二アンモニウム、水酸化リチウム、水酸化ナトリウム、水酸化カリウム、水酸化セシウム、
である。
酢酸エチル、酢酸イソプロピル、酢酸アミル等のエステル溶媒;
n−ヘキサン、ヘプタン、オクタン、シクロヘキサン、シクロペンタン等の脂肪族炭化水素溶媒;
ジクロロメタン、クロロホルム、四塩化炭素、1,2−ジクロロエタン等のハロゲン化溶媒;
トルエン、ベンゼン、キシレン等の芳香族炭化水素溶媒;
N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N−メチルピロジノン等のアミド溶媒;
ジメチルスルホキシド、スルホラン等の含硫黄溶媒;
アセトニトリル、バレロニトリル、ベンゾニトリル等のニトリル溶媒;
酢酸、プロピオン酸、酪酸等のカルボン酸溶媒;
等を挙げることが出来、これらの溶媒は、単独で又は2種以上組み合わせて使用出来る。
以下、本発明のジナフトチオフェン誘導体について説明する。
本発明の一般式(E)で表せる化合物の置換基R21〜R32としては、芳香族化合物の置換基として公知慣用のものであれば制限無く用いることが出来るが、例えば、
非環式又は環式の炭素原子数1〜20のアルキル基(該アルキル基中の−CH2−が、酸素原子、硫黄原子及び窒素原子が各々直接結合しないように、−O−、−R’C=CR’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’は炭素原子数1〜20の非環式又は環式アルキル基を表す。))、ハロゲノ基、芳香族基(該芳香族基は、非環式又は環式の炭素原子数1〜20のアルキル基、ハロゲノ基、芳香族基、又はニトリル基で置換されていてもよく、該アルキル基中の−CH2−が、酸素原子、硫黄原子及び窒素原子が各々直接結合しないように、−O−、−CR’’=CR’’−、−CO−、−OCO−、−COO−、−S−、−SO2−、−SO−、−NH−、−NR’’−又は−C≡C−で置換されてよく、該アルキル基中の水素原子は、芳香族基、ハロゲノ基、又はニトリル基によって置換されていてもよい(但し、R’’は炭素原子数1〜20の非環式又は環式アルキル基を表す。))、ニトロ基、又はニトリル基から選ばれる基を挙げることが出来る。
イソプロピル基、イソブチル基、イソペンチル基、ネオペンチル基、1−メチルペンチル基、4−メチル−2−ペンチル基、3,3−ジメチルブチル基、2−エチルブチル基、1−メチルヘキシル基、シクロヘキシルメチル基、tert−オクチル基、1−メチルヘプチル基、2−エチルヘキシル基、3−エチルヘプチル基、2−プロピルペンチル基、2,2−ジメチルヘプチル基、2,6−ジメチル−4−ヘプチル基、3,5,5−トリメチルヘキシル基、1−メチルデシル基、1−ヘキシルヘプチル基等の分岐アルキル基;
シクロペンチル基、シクロヘキシル基、4−メチルシクロヘキシル基、シクロヘプチル基、シクロオクチル基等の環状アルキル基;
等を挙げることが出来る。
等を挙げることが出来る。
(A−19)の具体例としては、一般式(A−19−1)で表される、置換基を有してもよいフェニル基で置換されたエチニル基、または一般式(A−19−2)で表される、置換基を有してもよいチエニル基で置換されたエチニル基を挙げることができる。前記置換基の具体例としては、炭素原子数1〜20の直鎖又は分岐アルキル基を挙げることができる。
更に高い移動度の化合物を得るためには、(B−1)無置換の芳香族炭化水素基又は複素芳香族基、(B−2)ハロゲン化芳香族炭化水素基又は複素芳香族基、(B−3)芳香族炭化水素基又は複素芳香族基が単結合で連結した芳香族炭化水素基又は複素芳香族基、(B−5)炭素原子数1〜20の直鎖又は分岐アルキル基置換の芳香族炭化水素基又は複素芳香族基、(B−6)炭素数1〜20の脂環式アルキル基置換の芳香族炭化水素基又は複素芳香族基、(B−7)炭素原子数1〜19のアルコキシ基置換の芳香族炭化水素基又は複素芳香族基、(B−8)炭素原子数2〜19のアルコキシアルキル基置換の芳香族炭化水素基又は複素芳香族基が特に好ましい。
ピロリル基、インドリル基、フリル基、チエニル基、イミダゾリル基、ベンゾフリル基、トリアゾリル基、ベンゾトリアゾリル基、ベンゾチエニル基、ピラゾリル基、インドリジニル基、キノリニル基、イソキノリニル基、カルバゾリル基、ジベンゾフラニル基、ジベンゾチオフェニル基、インドリニル基、チアゾリル基、ピリジル基、ピリミジル基、ピラジニル基、ピリダジニル基、チアジアジニル基、オキサジアゾリル基、ベンゾキノリニル基、チアジアゾリル基、ピロロチアゾリル基、ピロロピリダジニル基、テトラゾリル基、オキサゾリル基等、無置換の5員環又は6員環の複素芳香族基や、該複素芳香族基に他の芳香族基が縮合した多環式複素芳香族基;
等を挙げることが出来る。
(B−7)の具体例としては、メトキシフェニル基、エトキシフェニル基、プロポキシフェニル基、イソプロポキシフェニル基、ブトキシフェニル基、ペンチルオキシフェニル基、ヘキシルオキシフェニル基、ヘプチルオキシフェニル基、オクチルオキシフェニル基、2−エチルヘキシルオキシフェニル基、デシルオキシフェニル基、ドデシルオキシフェニル基、ステアリルオキシフェニル基等を挙げることが出来る。
(B−8)の具体例としては、4−(2−エトキシエチル)フェニル基、4−(2−n−ヘキシルオキシエチル)フェニル基、4−(2−n−ヘプチルオキシエチル)フェニル基、4−(2−n−テトラデシルオキシエチル)フェニル基、4−(2−シクロヘキシルオキシエチル)フェニル基、4−(12−エトキシドデシル)フェニル基、4−(シクロヘキシルオキシエチル)フェニル基、5−(2−エトキシエチル)チエニル基、5−(2−n−テトラデシルオキシエチル)チエニル基、5−(2−シクロヘキシルオキシエチル)チエニル基、5−(12−エトキシドデシル)チエニル基等を挙げることが出来る。
本発明の化合物は、有機半導体素子を用途とした、有機半導体材料として使用することが出来る。本発明の化合物を、有機半導体として使用するためには、通常、膜形態(有機半導体膜又は有機半導体層)にて使用される。膜の形成にあたっては、真空蒸着等公知慣用の乾式成膜法により形成しても構わないが、低温成膜が可能で、生産性に優れる湿式成膜法(塗工法又は印刷法)にて形成することが好ましく、そのために、本発明の化合物、即ち有機半導体材料は、インクとして使用することが好ましい。インクを調製するためには、本発明の化合物を溶媒に溶解する。また、半導体特性を損なわない範囲で、インク特性(印刷適性)を付与するために、フッ素系やシリコン系等のレベリング剤、及び、ポリスチレンやアクリル樹脂や高分子系有機半導体化合物等の高分子化合物を粘度調整剤として添加することも出来る。
使用する溶媒は何を用いても構わず、また2種以上の溶媒を混合して用いても良い。具体的には、n−ヘキサン、n−オクタン、n−デカン、n−ドデカン等の脂肪族系溶媒;
ベンゼン、トルエン、クメン、o−キシレン、m−キシレン、p−キシレン、p−シメン、メシチレン、アニソール、2−メチルアニソール、3−メチルアニソール、4−メチルアニソール、2,5−ジメチルアニソール、3,5−ジメトキシトルエン、2,4−ジメチルアニソール、フェネトール、安息香酸メチル、安息香酸エチル、安息香酸プロピル、安息香酸ブチル、1,5−ジメチルテトラリン、n−プロピルベンゼン、n−ブチルベンゼン、n−ペンチルベンゼン、1,3,5−トリエチルベンゼン、1,3−ジメトキシベンゼン、2,5−ジエチルシベンゼン、クロロベンゼン、o−ジクロロベンゼン、トリクロロベンゼン等の芳香族系溶媒;
テトラヒドロフラン、ジオキサン、エチレングリコールジエチルエーテル、アニソール、ベンジルエチルエーテル、エチルフェニルエーテル、ジフェニルエーテル、メチル−t−ブチルエーテル等のエーテル系溶媒;
酢酸メチル、酢酸エチル、エチルセロソルブ、プロピレングリコールメチルエーテルアセテート等のエステル系溶媒;
メタノール、エタノール、イソプロパノール等のアルコール系溶媒;
アセトン、メチルエチルケトン、シクロヘキサノン、2−ヘキサノン、2−ヘプタノン、3−ヘプタノン等のケトン系溶媒;
その他ジメチルホルムアミド、ジメチルスルホキシド、ジエチルホルムアミド等が挙げられるが、これらに限定されることはない。
調製された液体組成物における本発明の化合物の濃度としては、0.01〜20重量%であることが好ましく、更には0.1〜10重量%であることが好ましい。
次に、本発明の有機半導体素子について説明する。本発明の有機半導体素子は、本発明の化合物を、活性層部(半導体層)に含有する有機半導体素子である。
次に本発明の化合物を含有する有機トランジスタについて説明する。
有機トランジスタは、通常、ソース電極、ドレイン電極、ゲート電極、ゲート絶縁層、及び有機半導体層を有してなるものであり、各電極や各層の配置によって種々のタイプの有機トランジスタがあるが、本発明の化合物及び有機半導体材料は有機トランジスタの種類に限定されることなく、何れの有機トランジスタにも使用することが出来る。有機トランジスタの種類については、アルドリッチ社の材料科学の基礎第6号「有機トランジスタの基礎」等を参照することが出来る。
本発明の化合物の特徴は、公知慣用の有機半導体材料用化合物が、TC型で高特性を示しても、BC型でその特性が再現されないのに対し、後記の如く、BC型においても、1cm2/Vs以上の高い移動度を有する。これは、本発明の化合物が、インク液滴を滴下し、そのものを乾燥するだけで、適正な凝集力で、高移動度を与える多結晶膜を形成するためである。
又、有機半導体層は、結晶性を高め半導体特性の向上等を図ることを目的に、必要に応じて、成膜後にアニーリングを実施してもよい。アニーリングの温度は50〜200℃が好ましく、70〜200℃であると更に好ましく、時間は10分〜12時間が好ましく、1時間〜10時間がより好ましく、30分〜10時間であると更に好ましい。
(実施例1)<化合物(1)の製造>
1H NMR(300MHz,CDCl3):δ7.89(d,J=Hz,1H),δ7.69(d,J=9.3Hz,1H),δ7.62(s,J=9.0Hz,6H),δ7.40(dd,J=1.8Hz,8.4Hz,1H),δ7.14(dd,J=2.4Hz,9.0Hz,1H),δ7.02(s,J=2.4Hz,1H).
1H NMR(300MHz,CDCl3):δ87.70−7.67(m,2H),δ7.51(s,1H),δ7.20−7.17(m,1H),δ7.08−7.06(m,2H),δ3.91(s,3H),δ2.74(t,J=7.5Hz,3H),δ1.75−1.64(m,2H),δ1.42−1.24(m,6H),δ0.93−0.86(m,3H).
1H NMR(300MHz,CDCl3):δ7.71−7.66(m,2H),δ7.44(s,1H),δ7.17(dd,J=1.5Hz,8.4Hz,1H),δ7.08(d,J=2.7Hz,1H),δ7.02(dd,J=2.7Hz,8.7Hz,1H),δ4.20−4.00(br,1H),δ3.80(s,3H),δ2.73(s,J=7.5Hz,2H),δ1.68−1.62(m,2H),δ1.41−1.22(m,6H),δ0.90−0.86(m,3H).
1H NMR(300MHz,CDCl3):δ7.85−7.72(m,7H),δ7.47−7.23(m,6H),δ2.74(t,J=7.4Hz,2H),δ1.70−1.63(m,2H),δ1.38−1.28(m,6H),δ0.88(t,J=6.9Hz,3H).
1H NMR(300MHz,CDCl3):δ8.70(s,1H),δ8.68(s,1H),δ8.22(s,1H),δ8.15(s,1H),δ8.06−8.03(m,1H),δ7.98−7.96(m,1H),δ7.92−7.89(m,1H),δ7.67(s,1H),δ7.54−7.51(m,2H),δ7.38(dd,J=1.5Hz,8.4Hz,1H),δ2.82(t,J=7.2Hz,2H),δ1.76−1.70(m,2H),δ1.36−1.24(m,6H),δ0.90(t,J=6.6Hz,3H).
ガラス基板(図1の1に相当)上に金属マスクを用いてアルミニウムを真空蒸着法にて約30nmの厚さで成膜して、ゲート電極を形成した(図1の2に相当)。ここに、パリレン蒸着装置(ラボコーターPDS2010、日本パリレン製)を用いて、ジクロロ−ジパラキシリレン(DPX−C、日本パリレン製)を原料にして、ポリパラクロロキシリレン(パリレンC)薄膜(厚さ500nm)をケミカルベーパーデポジション(CVD)法にて作製し(図1の3に相当)、更に、真空蒸着法によって、金薄膜(厚さ40nm)からなるソース・ドレイン電極をパターン形成した(図1の5と6に相当。チャネル長L(ソース電極−ドレイン電極間隔)を75μm、チャネル幅Wを5.0mmとした)。次に、このようにして得られた基板を、ペンタフルオロチオフェノールの0.1%エタノール溶液に1時間浸漬したのち、窒素ブローで乾燥し、前記化合物(1)の0.4%p−キシレン溶液(有機半導体インク)の液滴0.1μLを、前記ソース・ドレイン電極の間にドロップキャスト(滴下)した後、自然濃縮により乾固させることで、前記化合物(1)よりなる有機半導体層(図1の4に相当)を形成した(有機半導体溶液(インク)液滴の滴下(ドロップキャスト)とその乾燥によって有機半導体層を形成)。
このようにして得られた有機トランジスタについて、半導体特性(移動度)を評価した。半導体特性(移動度)は、ソース電極を接地し、ドレイン電極に−80Vを印加した状態で、デジタルマルチメーター(SMU237、ケースレー製)を用いて、ゲート電極に0から−80V、電圧(Vg)をスイープ印加しながら、ドレイン電極に流れる電流(Id)を測定し、√Id−Vgの傾きから、(式1)を用いて求めた。単位はcm2/V・sである。
評価結果を表1に示した。
<化合物(2)の製造>
1H NMR(300MHz,CDCl3):δ8.69(s,1H),δ8.67(s,1H),δ8.21(s,1H),δ8.14(s,1H),δ8.09−8.04(m,1H),δ8.03−7.98(m,1H),δ7.91−7.89(m,1H),δ7.66(s,1H),δ7.56−7.48(m,2H),δ7.38(dd,J=1.5Hz,8.4Hz,1H),δ2.82(t,J=7.2Hz,2H),δ1.77−1.69(m,2H),δ1.36−1.24(m,10H),δ0.88(t,J=6.6Hz,3H).
化合物(1)のかわりに、化合物(2)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
(実施例3)
<化合物(3)の製造>
1H NMR(300MHz,CDCl3):δ8.69(s,1H),δ8.67(s,1H),δ8.21(s,1H),δ8.15(s,1H),δ8.06−8.03(m,1H),δ7.99−7.96(m,1H),δ7.92−7.90(m,1H),δ7.66(s,1H),δ7.54−7.49(m,2H),δ7.38(dd,J=1.5Hz,7.8Hz,1H),δ2.82(t,J=7.8Hz,2H),δ1.77−1.69(m,2H),δ1.42−1.18(m,14H),δ0.88(t,J=6.6Hz,3H).
化合物(1)のかわりに、化合物(3)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
<化合物(4)の製造>
1H NMR(300MHz,CDCl3):δ8.70(s,1H),δ8.66(s,1H),δ8.22(s,1H),δ8.18(s,1H),δ8.07−8.04(m,1H),δ7.92−7.90(m,1H),δ7.84−7.81(m,2H),δ7.56−7.49(m,2H),δ7.40(dd,J=1.7Hz,8.3Hz,1H),δ2.83(t,J=7.2Hz,2H),δ1.78−1.70(m,2H),δ1.42−1.28(m,6H),δ0.90(t,J=6.6Hz,3H).
化合物(1)のかわりに、化合物(4)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
(実施例5)
<化合物(5)の製造>
1H NMR(300MHz,CDCl3):δ7.96(s,1H),δ7.82(d,J=8.7Hz,1H),δ7.71(d,J=8.4Hz,1H),δ7.53(dd,J=1.8Hz,8.7Hz,1H),δ7.41(d,J=2.4Hz,1H),7.26(dd,J=2.4Hz,9.0Hz,1H),δ3.48(s,3H),δ3.40(s,3H).
1H NMR(300MHz,CDCl3):δ7.84(m,1H),δ7.73−7.61(m,3H),δ7.45(dd,J=1.8Hz,8.7Hz,1H),δ7.33(dd,J=1.8Hz,8.7Hz,1H),δ3.62(s,1H).
1H NMR(300MHz,CDCl3):δ7.86(s,1H),δ7.82(d,J=1.8Hz,1H),δ7.76−7.61(m,5H),δ7.52−7.46(m,2H),δ7.40−7.32(m,3H),δ2.74(t,J=7.5Hz,2H),δ1.73−1.62(m,2H),δ1.41−1.25(m,6H),δ0.88(t,J=6.9Hz,3H).
1H NMR(300MHz,CDCl3):δ8.64(s,1H),δ8.61(s,1H),δ8.13(s,1H),δ8.09(s,1H),δ8.04(d,J=1.5Hz,1H),δ7.95(d,J=8.4Hz,1H),δ7.89(d,J=8.7Hz,1H),δ7.65(s,1H),δ7.56(dd,J=1.8Hz,9.0Hz,1H),δ7.38(dd,J=1.8Hz,8.4Hz,1H),δ2.81(t,J=7.5Hz,2H),δ1.49−1.68(m,2H),δ1.38−1.26(m,6H),δ0.90(t,J=6.9Hz,3H).
反応液にCHCl350mLを加え、水洗した後、硫酸マグネシウムで有機相を乾燥、溶媒を留去した。得られた粗製物をシリカゲルカラムクロマトグラフィー(シクロヘキサン)で分離精製することで、化合物(5)たる3−ヘキシル−9−((4−ペンチルフェニル)エチニル)ジナフト[2,3−b:2’,3’−d]チオフェン0.043mg(収率、37%)を得た。
1H NMR(300MHz,CDCl3):δ8.68(s,1H),δ8.65(s,1H),δ8.18(s,1H),δ8.15(s,1H),δ8.09(s,1H),δ8.02−7.96(m,2H),δ7.67(s,1H),δ7.60(dd,J=1.5Hz,8.4Hz,1H),δ7.51(d,J=8.1Hz,2H),δ7.39(dd,J=1.8Hz,8.4Hz,1H),δ7.20(d,J=8.1Hz,2H),δ2.82(t,J=7.2Hz,2H),δ2.64(t,J=7.8Hz,2H),δ1.77−1.61(m,4H),δ1.43−1.27(m,10H),δ0.93−0.87(m,6H).
化合物(1)のかわりに、化合物(5)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
<化合物(6)の製造法>
1H NMR(300MHz,CDCl3):δ8.66(s,1H),δ8.65(s,1H),δ8.17(s,1H),δ8.14(s,1H),δ8.09(s,1H),δ8.01−7.95(m,2H),δ7.66(s,1H),δ7.61(dd,J=1.5Hz,8.5Hz,1H),δ7.51(d,J=8.1Hz,2H),δ7.40(dd,J=1.8Hz,8.5Hz,1H),δ7.20(d,J=8.1Hz,2H),δ2.82(t,J=7.2Hz,2H),δ2.64(t,J=7.8Hz,2H),δ1.79−1.58(m,4H),δ1.43−1.28(m,16H),δ0.92−0.87(m,6H).
化合物(1)のかわりに、化合物(6)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
<化合物(7)の製造法>
1H NMR(300MHz,CDCl3):δ8.66(s,1H),δ8.65(s,1H),δ8.17(s,1H),δ8.14(s,1H),δ8.07(s,1H),δ8.01−7.96(m,2H),δ7.67(s,1H),δ7.57(d,8.4Hz,1H),δ7.39(d,J=8.4Hz,1H),δ7.15(d,J=2.4Hz,1H),δ6.70(d,J=2.4Hz,1H),δ2.82(t,J=7.5Hz,2H),δ2.52(s,3H),δ1.76−1.70(m,2H),δ1.44−1.28(m,6H),δ0.93−0.87(m,3H).
化合物(1)のかわりに、化合物(7)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
<化合物(179)の製造法>
国際公開第2013/125599号パンフレットに記載の合成方法に従って、一般式(179)で表される化合物を得た。
化合物(1)のかわりに、化合物(179)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
<化合物(180)の製造法>
比較例1において、2−ヘキシル−7−メトキシナフタレンを、2−デシル−7−メトキシナフタレンに変更した以外は比較例1に準拠して、一般式(180)で表される化合物を得た。
化合物(1)のかわりに、化合物(180)を用いた以外は、実施例1と同様にして、有機トランジスタの製造、半導体特性(移動度)の評価を実施した。結果を表1に示す。
Claims (10)
- 一般式(E)で表されるジナフトチオフェン誘導体。ただし、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)、および化合物(E−L)を除く。
R21とR32は互いに同じであるか異なり、R22とR31は互いに同じであるか異なり、R23とR30は互いに同じであるか異なり、R24とR29は互いに同じであるか異なり、R25とR28は互いに同じであるか異なり、R26とR27は互いに同じであるか異なるが、R21とR32、R22とR31、R23とR30、R24とR29、R25とR28、R26とR27、の6組の組み合わせのうち、少なくとも一つの組み合わせは互いに異なる。)
- 前記R21〜R32が、水素原子、フッ素原子(フルオロ基)、非環式又は環式の炭素原子数1〜20のアルキル基、Ph−C≡C*(Phは置換されていてもよいフェニル基を表し、*は結合位置を表す。)、またはTh−C≡C*(Thは置換されていてもよいチエニル基を表し、*は結合位置を表す。)である、請求項1に記載のジナフトチオフェン誘導体。
- 前記した置換基に係わる6組の組み合わせ(R21とR32、R22とR31、R23とR30、R24とR29、R25とR28、R26とR27)のうち、少なくとも一つの組み合わせは互いに異なり、且つ、それ以外の組み合わせは互いに同一で水素原子である、請求項1または2に記載のジナフトチオフェン誘導体。
- 前記した置換基に係わる6組の組み合わせ(R21とR32、R22とR31、R23とR30、R24とR29、R25とR28、R26とR27)のうち、R21とR32、R22とR31、R25とR28、R26とR27、はいずれも同一で水素原子であり、R23とR30は互いに同じであるか異なり、R24とR29は互いに同じであるか異なるが、R23とR30、R24とR29、の2組の組み合わせのうち、少なくとも一つの組み合わせは互いに異なる、請求項1または2に記載のジナフトチオフェン誘導体。
- 請求項1〜4のいずれかに記載のジナフトチオフェン誘導体を含有する有機半導体材料。
- 請求項6に記載の有機半導体材料を含有する有機半導体インク。
- 請求項6に記載の有機半導体材料を含有する有機半導体膜。
- 請求項6に記載の有機半導体材料を含有する有機半導体素子。
- 請求項6に記載の有機半導体材料を含有する有機トランジスタ。
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