JP6884746B2 - 高分子化合物、組成物及び有機薄膜トランジスタ - Google Patents
高分子化合物、組成物及び有機薄膜トランジスタ Download PDFInfo
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- JP6884746B2 JP6884746B2 JP2018500136A JP2018500136A JP6884746B2 JP 6884746 B2 JP6884746 B2 JP 6884746B2 JP 2018500136 A JP2018500136 A JP 2018500136A JP 2018500136 A JP2018500136 A JP 2018500136A JP 6884746 B2 JP6884746 B2 JP 6884746B2
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- LTDYJEHLDICQSN-UHFFFAOYSA-N methoxymethyl 4-ethenylbenzoate Chemical compound COCOC(=O)C1=CC=C(C=C)C=C1 LTDYJEHLDICQSN-UHFFFAOYSA-N 0.000 description 1
- SNZRPPBWRSEVIU-UHFFFAOYSA-N methyl 4-chloropyridine-3-carboxylate Chemical compound COC(=O)C1=CN=CC=C1Cl SNZRPPBWRSEVIU-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000013365 molecular weight analysis method Methods 0.000 description 1
- ZZSKMNCIAKKVRB-UHFFFAOYSA-N morpholin-4-yl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)N1CCOCC1 ZZSKMNCIAKKVRB-UHFFFAOYSA-N 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- JMCVCHBBHPFWBF-UHFFFAOYSA-N n,n-diethyl-2-methylprop-2-enamide Chemical compound CCN(CC)C(=O)C(C)=C JMCVCHBBHPFWBF-UHFFFAOYSA-N 0.000 description 1
- OVHHHVAVHBHXAK-UHFFFAOYSA-N n,n-diethylprop-2-enamide Chemical compound CCN(CC)C(=O)C=C OVHHHVAVHBHXAK-UHFFFAOYSA-N 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- FFIQBGKMFJIHFA-UHFFFAOYSA-N n-(2,3,4,5,6-pentafluorophenyl)prop-2-enamide Chemical compound FC1=C(F)C(F)=C(NC(=O)C=C)C(F)=C1F FFIQBGKMFJIHFA-UHFFFAOYSA-N 0.000 description 1
- UUORTJUPDJJXST-UHFFFAOYSA-N n-(2-hydroxyethyl)prop-2-enamide Chemical compound OCCNC(=O)C=C UUORTJUPDJJXST-UHFFFAOYSA-N 0.000 description 1
- ITHABPRFIRDTRK-UHFFFAOYSA-N n-(4-fluorophenyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NC1=CC=C(F)C=C1 ITHABPRFIRDTRK-UHFFFAOYSA-N 0.000 description 1
- LVCGCAYBLBKRDP-UHFFFAOYSA-N n-(4-fluorophenyl)prop-2-enamide Chemical compound FC1=CC=C(NC(=O)C=C)C=C1 LVCGCAYBLBKRDP-UHFFFAOYSA-N 0.000 description 1
- POVITWJTUUJBNK-UHFFFAOYSA-N n-(4-hydroxyphenyl)prop-2-enamide Chemical compound OC1=CC=C(NC(=O)C=C)C=C1 POVITWJTUUJBNK-UHFFFAOYSA-N 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N n-Octanol Natural products CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- PNLUGRYDUHRLOF-UHFFFAOYSA-N n-ethenyl-n-methylacetamide Chemical compound C=CN(C)C(C)=O PNLUGRYDUHRLOF-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000000082 organogermanium group Chemical group 0.000 description 1
- VJZFIQQDUUTCDJ-UHFFFAOYSA-N oxan-2-yl 2-ethenylbenzoate Chemical compound C=CC1=CC=CC=C1C(=O)OC1OCCCC1 VJZFIQQDUUTCDJ-UHFFFAOYSA-N 0.000 description 1
- GRYPAHWNUAJRKU-UHFFFAOYSA-N oxan-2-yl 4-ethenylbenzoate Chemical compound C1=CC(C=C)=CC=C1C(=O)OC1OCCCC1 GRYPAHWNUAJRKU-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- HDBWAWNLGGMZRQ-UHFFFAOYSA-N p-Vinylbiphenyl Chemical group C1=CC(C=C)=CC=C1C1=CC=CC=C1 HDBWAWNLGGMZRQ-UHFFFAOYSA-N 0.000 description 1
- 238000000059 patterning Methods 0.000 description 1
- HVAMZGADVCBITI-UHFFFAOYSA-M pent-4-enoate Chemical compound [O-]C(=O)CCC=C HVAMZGADVCBITI-UHFFFAOYSA-M 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920000553 poly(phenylenevinylene) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920001088 polycarbazole Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- NVNSVQJVBIWZNM-UHFFFAOYSA-N prop-2-enyl 4-hydroxybenzoate Chemical compound OC1=CC=C(C(=O)OCC=C)C=C1 NVNSVQJVBIWZNM-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 1
- MYGFXCLXHGITIQ-UHFFFAOYSA-N quinolin-4-ylhydrazine Chemical compound C1=CC=C2C(NN)=CC=NC2=C1 MYGFXCLXHGITIQ-UHFFFAOYSA-N 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- WWGXHTXOZKVJDN-UHFFFAOYSA-M sodium;n,n-diethylcarbamodithioate;trihydrate Chemical compound O.O.O.[Na+].CCN(CC)C([S-])=S WWGXHTXOZKVJDN-UHFFFAOYSA-M 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- PFBLRDXPNUJYJM-UHFFFAOYSA-N tert-butyl 2-methylpropaneperoxoate Chemical compound CC(C)C(=O)OOC(C)(C)C PFBLRDXPNUJYJM-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical class N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- FHCPAXDKURNIOZ-UHFFFAOYSA-N tetrathiafulvalene Chemical class S1C=CSC1=C1SC=CS1 FHCPAXDKURNIOZ-UHFFFAOYSA-N 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 238000007736 thin film deposition technique Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- HLWCOIUDOLYBGD-UHFFFAOYSA-N trichloro(decyl)silane Chemical compound CCCCCCCCCC[Si](Cl)(Cl)Cl HLWCOIUDOLYBGD-UHFFFAOYSA-N 0.000 description 1
- ZOYFEXPFPVDYIS-UHFFFAOYSA-N trichloro(ethyl)silane Chemical compound CC[Si](Cl)(Cl)Cl ZOYFEXPFPVDYIS-UHFFFAOYSA-N 0.000 description 1
- PYJJCSYBSYXGQQ-UHFFFAOYSA-N trichloro(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](Cl)(Cl)Cl PYJJCSYBSYXGQQ-UHFFFAOYSA-N 0.000 description 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 229940096522 trimethylolpropane triacrylate Drugs 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/16—Halogens
- C08F12/20—Fluorine
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- C08F12/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
- C08F12/02—Monomers containing only one unsaturated aliphatic radical
- C08F12/04—Monomers containing only one unsaturated aliphatic radical containing one ring
- C08F12/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
- C08F12/22—Oxygen
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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Description
[1] ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位と、
ヒドロキシ基を有する繰り返し単位、カルボキシ基を有する繰り返し単位並びにヒドロキシ基及びカルボキシ基を有する繰り返し単位を含む群から選ばれる少なくとも1種の繰り返し単位と、
下記式(1)で表される繰り返し単位と
を含む高分子化合物。
R1、R2、R3は、互いに異なっていてもよく、水素原子、フッ素原子、又は炭素原子数1〜20の1価の有機基を表す。
R4は、水素原子、塩素原子、臭素原子、ヨウ素原子又は炭素原子数1〜20の1価の有機基を表す。
Rfは、フッ素原子、又はフッ素原子を含む1価の有機基を表す。
Raは、炭素原子数1〜20の2価の有機基、−O−で表される基、−CO−で表される基、−COO−で表される基、−NHCO−で表される基、又は−NHCOO−で表される基を表し、前記−O−で表される基、前記−CO−で表される基、前記−COO−で表される基、前記−NHCO−で表される基、及び前記−NHCOO−で表される基の結合手は、前記式(1)中の前記R1が結合する炭素原子側に位置していても、前記式(1)中のベンゼン環を構成する炭素原子側に位置していてもよく、前記2価の有機基中の水素原子は、フッ素原子で置換されていてもよい。
m1は、0〜6の整数を表す。
n1は、1〜5の整数を表す。
Raが複数個ある場合、それらは互いに異なっていてもよい。R4が複数個ある場合、それらは互いに異なっていてもよい。Rfが複数個ある場合、それらは互いに異なっていてもよい。)
[2] 前記ヒドロキシ基を有する繰り返し単位及びカルボキシ基を有する繰り返し単位が、下記式(2)で表される繰り返し単位である、[1]に記載の高分子化合物。
R5、R6、R7は、互いに異なっていてもよく、水素原子、フッ素原子、又は炭素原子数1〜20の1価の有機基を表す。Rbは、炭素原子数1〜20の2価の有機基、−O−で表される基、−CO−で表される基、−COO−で表される基、−NHCO−で表される基、又は−NHCOO−で表される基を表し、前記−O−で表される基、前記−CO−で表される基、前記−COO−で表される基、前記−NHCO−で表される基、及び前記−NHCOO−で表される基の結合手は、前記式(2)中の前記R5が結合する炭素原子側に位置していても、前記式(2)中のXa側に位置していてもよい。前記2価の有機基中の水素原子は、フッ素原子で置換されていてもよい。
m2は、0〜6の整数を表す。
Xaは、ヒドロキシ基又はカルボキシ基を表す。)
[3] 前記ブロック化イソシアナト基又はブロック化イソチオシアナト基が、下記式(3)で表される基又は下記式(4)で表される基である、[1]又は[2]に記載の高分子化合物。
Xbは、酸素原子又は硫黄原子を表す。
R8〜R12は、互いに異なっていてもよく、水素原子又は炭素原子数1〜20の1価の有機基を表す。)
[4] [1]〜[3]のいずれか一つに記載の高分子化合物を含む組成物。
[5] [1]〜[3]のいずれか一つに記載の高分子化合物及び有機溶媒のみからなる、[4]に記載の組成物。
[6] [4]又は[5]に記載の組成物からなる有機薄膜トランジスタの絶縁層用組成物。
[7] [4]〜[6]のいずれか一つに記載の組成物を硬化した膜。
[8] [7]に記載の膜をゲート絶縁層として含む、有機薄膜トランジスタ。
[9] [7]に記載の膜をオーバーコート層としてさらに含む、[8]に記載の有機薄膜トランジスタ。
[10] [4]〜[6]のいずれか一つに記載の組成物を、基材の表面に塗布して塗布層を形成する工程と、
前記塗布層を硬化する工程と
を含む、有機薄膜トランジスタの製造方法。
本明細書で共通して用いられる用語は、特記しない限り、以下の意味である。
炭素原子数1〜20の1価の有機基としては、アルキル基が好ましい。
本発明の高分子化合物は、ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位と、ヒドロキシ基を有する繰り返し単位、カルボキシ基を有する繰り返し単位並びにヒドロキシ基及びカルボキシ基を有する繰り返し単位を含む群から選ばれる少なくとも1種の繰り返し単位と、下記式(1)で表される繰り返し単位とを含む高分子化合物である(以下、「高分子化合物(A)」という場合がある。)。
R1、R2、R3は、互いに異なっていてもよく、水素原子、フッ素原子、又は炭素原子数1〜20の1価の有機基を表す。
R4は、水素原子、塩素原子、臭素原子、ヨウ素原子又は炭素原子数1〜20の1価の有機基を表す。
Rfは、フッ素原子、又はフッ素原子を含む1価の有機基を表す。
Raは、炭素原子数1〜20の2価の有機基、−O−で表される基、−CO−で表される基、−COO−で表される基、−NHCO−で表される基、又は−NHCOO−で表される基を表し、前記−O−で表される基、前記−CO−で表される基、前記−COO−で表される基、前記−NHCO−で表される基、及び前記−NHCOO−で表される基の結合手は、前記式(1)中の前記R1が結合する炭素原子側に位置していても、前記式(1)中のベンゼン環を構成する炭素原子側に位置していてもよく、前記2価の有機基中の水素原子は、フッ素原子で置換されていてもよい。
m1は、0〜6の整数を表す。
n1は、1〜5の整数を表す。
Raが複数個ある場合、それらは互いに異なっていてもよい。R4が複数個ある場合、それらは互いに異なっていてもよい。Rfが複数個ある場合、それらは互いに異なっていてもよい。
ここで、高分子化合物(A)について説明する。高分子化合物(A)は、同一分子内にブロック化イソシアナト基及び/又はブロック化イソチオシアナト基と、ヒドロキシ基及び/又はカルボキシ基と、前記式(1)で表される繰り返し単位とを含む。
高分子化合物(A)は、例えば、ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位の原料となるモノマー(重合性モノマー)と、ヒドロキシ基を有する繰り返し単位、カルボキシ基を有する繰り返し単位並びにヒドロキシ基及びカルボキシ基を有する繰り返し単位を含む群から選ばれる少なくとも1種の繰り返し単位の原料となるモノマー(重合性モノマー)と、前記式(1)で表される繰り返し単位の材料となるモノマー(重合性モノマー)と、要すれば高分子化合物(A)が含み得るその他の繰り返し単位の原料となる他のモノマー(重合性モノマー)とを、光重合開始剤もしくは熱重合開始剤を用いて共重合させる方法により製造することができる。
高分子化合物(A)は、ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位を含む。
換言すると、高分子化合物(A)は、ブロック化イソシアナト基のみを有する繰り返し単位を含んでいても、ブロック化イソチオシアナト基のみを有する繰り返し単位を含んでいても、ブロック化イソシアナト基及びブロック化イソチオシアナト基の両方を有する繰り返し単位を含んでいても、ブロック化イソシアナト基のみを有する繰り返し単位、ブロック化イソチオシアナト基のみを有する繰り返し単位、並びにブロック化イソシアナト基及びブロック化イソチオシアナト基の両方を有する繰り返し単位の2種以上の組み合わせを含んでいてもよい。
以下、ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位の原料となるモノマーの例を示す。
高分子化合物(A)は、ヒドロキシ基を有する繰り返し単位、カルボキシ基を有する繰り返し単位並びにヒドロキシ基及びカルボキシ基を有する繰り返し単位を含む群から選ばれる少なくとも1種の繰り返し単位を含む。
高分子化合物(A)は、下記式(1)で表される繰り返し単位を含む。
高分子化合物(A)は、ブロック化イソシアナト基及び/又はブロック化イソチオシアナト基を有するモノマー、ヒドロキシ基及び/又はカルボキシ基を有する繰り返し単位の原料となるモノマー、上記式(1)で表される繰り返し単位の原料となるモノマー以外の他の繰り返し単位の材料となるモノマーをさらに添加して製造してもよい。
本発明の組成物は、高分子化合物(A)を含む。
本発明にかかる組成物には、2種以上の高分子化合物(A)が含まれていてもよい。
組成物における添加剤などの含有量は、高分子化合物(A)を100重量部とした場合、通常、0重量部〜40重量部である。
本発明の高分子化合物、該高分子化合物を含む組成物は、有機薄膜トランジスタの絶縁層用組成物として好適に用いることができる。
本発明の高分子化合物、該高分子化合物を含む組成物(絶縁層用組成物)を硬化した膜は、有機薄膜トランジスタの機能性部材として好適に用いることができる。
本発明の有機薄膜トランジスタは、既に説明した本発明の組成物を硬化したゲート絶縁層を含む。
以下、図面を参照して、本発明の組成物の好適な適用先である有機薄膜トランジスタの実施形態について説明する。
前記第1実施形態のボトムゲートトップコンタクト型の有機薄膜トランジスタ10は、例えば、基板1の主表面にゲート電極2を形成し、ゲート電極2を覆うようにゲート電極2が設けられた基板1(基材)の表面にゲート絶縁層3を形成し、ゲート絶縁層3上に有機半導体層4を形成し、有機半導体層4に接合するようにソース電極5及びドレイン電極6を形成し、さらに要すれば、基板1に設けられたゲート電極2、ゲート絶縁層3、有機半導体層4、ソース電極5及びドレイン電極6を覆うようにオーバーコート層7を形成することで製造することができる。
焼成は、例えば、80℃〜300℃、好ましくは120℃〜250℃の温度で5分間〜2時間、好ましくは10分間〜1時間程度加熱処理することにより行うことができる。ブロック化イソシアナト基及び/又はブロック化イソチオシアナト基からブロック化剤に由来する保護基を脱離させるための電磁波の照射条件及び焼成条件は、ブロック化イソシアナト基及び/又はブロック化イソチオシアナト基の種類及び量等に応じて適宜決定することができる。
本発明の組成物を用いて製造した有機薄膜トランジスタを用いて、有機薄膜トランジスタを含むディスプレイ用部材を製造することができる。また該有機薄膜トランジスタを含むディスプレイ用部材を用いて、ディスプレイ用部材を備えるディスプレイを製造することができる。
後述する高分子化合物Cの数平均分子量及び重量平均分子量は、ゲル透過クロマトグラフィ(GPC、Waters社製、商品名:Alliance GPC 2000)を用いて求めた。測定される高分子化合物Cは、オルトジクロロベンゼンに溶解させ、GPCに注入した。GPCの移動相にはオルトジクロロベンゼンを用いた。カラムは、「TSKgel GMHHR−H(S)HT(2本連結、東ソー社製)」を用いた。検出器にはUV検出器を用いた。
下記のスキームに沿って、高分子化合物Cを合成した。
反応容器内の気体を窒素ガスで置換した後に、下記式B−1で表される化合物B−1(286.8mg、0.200mmol)、下記式B−2で表される化合物B−2(77.6mg、0.200mmol)、テトラヒドロフランを19mL、トリス(ジベンジリデンアセトン)ジパラジウムを7.3mg、トリ−tert−ブチルホスホニウムテトラフルオロボレートを9.3mg加えて、撹拌した。得られた反応溶液に、3mol/Lのリン酸カリウム水溶液を1.0mL滴下し、3時間還流させた。得られた反応溶液に、フェニルボロン酸を24.4mg加えて、1時間還流させた。得られた反応溶液に、N,N−ジエチルジチオカルバミド酸ナトリウム三水和物を0.1g加えて、3時間還流させた。得られた反応溶液を水に注ぎ、トルエンを加え、トルエン層(トルエン溶液)を抽出した。得られたトルエン溶液を、酢酸水溶液及び水で洗浄した後、シリカゲルカラムを用いて精製した。得られたトルエン溶液をアセトンに滴下したところ、析出物が得られた。得られた析出物を、アセトンを溶媒として用いてソックスレー洗浄し、下記式で表される繰り返し単位を含む高分子化合物Cを得た。高分子化合物Cの得量は244mgであり、ポリスチレン換算の数平均分子量は3.1×104であり、重量平均分子量は6.5×104であった。
スチレン(純正化学社製)3.22g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.61g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)1.50g、4−ヒドロキシブチルアクリレート(日本化成社製)0.71g、2,2’−アゾビス(2−メチルプロピオニトリル)0.05g、プロピレングリコールモノメチルエーテルアセテート(PGMEA)(東京化成社製)6.05gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で17時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(1)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(1)のポリスチレン換算の数平均分子量は1.2×105であり、重量平均分子量は3.3×105であった。
2,3,4,5,6−ペンタフルオロベンジルメタクリレート(シンクエスト・ラボラトリーズ社製)5.32g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)0.61g、4−ヒドロキシブチルアクリレート(日本化成社製)0.36g、2,2’−アゾビス(2−メチルプロピオニトリル)0.04g、PGMEA(東京化成社製)8.21gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、70℃のオイルバス中で17時間重合させて、下記式(v)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(2)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(2)のポリスチレン換算の数平均分子量は5.4×104であり、重量平均分子量は4.5×105であった。
スチレン(純正化学社製)3.13g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.50g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)1.45g、2−ヒドロキシエチルメタクリレート(東京化成社製)0.78g、2,2’−アゾビス(2−メチルプロピオニトリル)0.045g、PGMEA(東京化成社製)5.93gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で16時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(vi)で表される繰り返し単位を含む高分子化合物(3)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(3)のポリスチレン換算の数平均分子量は9.2×104であり、重量平均分子量は2.2×105であった。
スチレン(純正化学社製)3.18g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.55g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)1.48g、メタクリル酸(東京化成社製)0.53g、2,2’−アゾビス(2−メチルプロピオニトリル)0.053g、PGMEA(東京化成社製)5.85gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で16時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(vii)で表される繰り返し単位を含む高分子化合物(4)が溶解している粘稠なPGMEA溶液を得た。高分子化合物(4)のポリスチレン換算の数平均分子量は3.0×104であり、重量平均分子量は9.3×104であった。
スチレン(純正化学社製)3.02g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.38g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)1.41g、4−ビニル安息香酸(東京化成社製)0.86g、2,2’−アゾビス(2−メチルプロピオニトリル)0.043g、PGMEA(東京化成社製)5.80gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で16時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(viii)で表される繰り返し単位を含む高分子化合物(5)が溶解している粘稠なPGMEA溶液を得た。高分子化合物(5)のポリスチレン換算の数平均分子量は4.1×104であり、重量平均分子量は1.3×105であった。
スチレン(純正化学社製)49.40g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)46.10g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)19.00g、2,2’−アゾビス(2−メチルプロピオニトリル)0.57g、PGMEA(和光純薬社製)76.71gを、250mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で18時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位を含む高分子化合物(6)が溶解している粘稠なPGMEA溶液を得た。
4−アミノスチレン(アルドリッチ社製)18.60g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ製)70.79g、2,2’−アゾビス(2−メチルプロピオニトリル)0.45g、PGMEA(東京化成社製)134.75gを、250mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で18時間重合させて、下記式(ii)で表される繰り返し単位、下記式(ix)で表される繰り返し単位を含む高分子化合物(7)が溶解している粘稠なPGMEA溶液を得た。
スチレン(純正化学社製)7.80g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)7.28g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)3.00g、2,2’−アゾビス(2−メチルプロピオニトリル)0.90g、2−ヘプタノン(東京化成社製)12.11gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で18時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位を含む高分子化合物(8)が溶解している粘稠な2−ヘプタノン溶液を得た。高分子化合物(8)のポリスチレン換算の数平均分子量は7.7×104であり、重量平均分子量は1.4×105であった。
2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.57g、4−ヒドロキシブチルアクリレート(日本化成社製)0.90g、2,2’−アゾビス(2−メチルプロピオニトリル)0.022g、2−ヘプタノン(東京化成社製)10.5gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で18時間重合させて、下記式(ii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(9)が溶解している粘稠な2−ヘプタノン溶液を得た。高分子化合物(9)のポリスチレン換算の数平均分子量は4.2×104であり、重量平均分子量は7.6×104であった。
スチレン(純正化学社製)2.87g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.20g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)1.33g、4−アミノスチレン(東京化成社製)0.66g、2,2’−アゾビス(2−メチルプロピオニトリル)0.040g、PGMEA(東京化成社製)8.10gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で17時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(ix)で表される繰り返し単位を含む高分子化合物(10)をゲルとして析出させた。
スチレン(純正化学社製)4.19g、2,3,4,5,6−ペンタフルオロスチレン(アルドリッチ社製)3.94g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)0.81g、4−ヒドロキシブチルアクリレート(日本化成社製)0.48g、2,2’−アゾビス(2−メチルプロピオニトリル)0.047g、PGMEA(東京化成社製)6.29gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、60℃のオイルバス中で17時間重合させて、下記式(i)で表される繰り返し単位、下記式(ii)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(11)が溶解している粘稠なPGMEA溶液を得た。高分子化合物(11)のポリスチレン換算の数平均分子量は6.9×104であり、重量平均分子量は1.7×105であった。
2,3,4,5,6−ペンタフルオロベンジルメタクリレート(シンクエスト・ラボラトリーズ社製)3.62g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)0.276g、4−ヒドロキシブチルアクリレート(日本化成社製)0.328g、2,2’−アゾビス(2−メチルプロピオニトリル)0.021g、PGMEA(東京化成社製)9.90gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、70℃のオイルバス中で16時間重合させて、下記式(v)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(12)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(12)のポリスチレン換算の数平均分子量は4.0×104であり、重量平均分子量は1.7×105であった。
2,3,4,5,6−ペンタフルオロベンジルメタクリレート(シンクエスト・ラボラトリーズ社製)3.85g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)0.412g、4−ヒドロキシブチルアクリレート(日本化成社製)0.123g、2,2’−アゾビス(2−メチルプロピオニトリル)0.022g、PGMEA(東京化成社製)10.3gを、50mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、70℃のオイルバス中で16時間重合させて、下記式(v)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(iv)で表される繰り返し単位を含む高分子化合物(13)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(13)のポリスチレン換算の数平均分子量は3.9×104であり、重量平均分子量は1.5×105であった。
2,3,4,5,6−ペンタフルオロベンジルメタクリレート(シンクエスト・ラボラトリーズ社製)18.63g、2−〔O−[1’−メチルプロピリデンアミノ]カルボキシアミノ〕エチル−メタクリレート(昭和電工社製、商品名「カレンズMOI−BM」)3.63g、4−ビニル安息香酸(東京化成社製)2.22g、2,2’−アゾビス(2−メチルプロピオニトリル)0.131g、PGMEA(東京化成社製)57.5gを、125mL耐圧容器(ACE GLASS社製)に入れ、窒素ガスでバブリングした後、密栓し、70℃のオイルバス中で16時間重合させて、下記式(v)で表される繰り返し単位、下記式(iii)で表される繰り返し単位、下記式(viii)で表される繰り返し単位を含む高分子化合物(14)が溶解している粘稠なPGMEA溶液を得た。得られた高分子化合物(14)のポリスチレン換算の数平均分子量は3.9×104であり、重量平均分子量は9.4×104であった。
合成例2で得た高分子化合物(1)のPGMEA溶液15.14g、PGMEA60.6gを125mLサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(1)を調製した。
合成例3で得た高分子化合物(2)のPGMEA溶液12.6g、PGMEA34.8gを100mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(2)を調製した。
合成例4で得た高分子化合物(3)のPGMEA溶液14.8g、PGMEA52.4gを100mLのサンプル瓶に入れ、攪拌して溶解することにより均一な塗布液(3)を調製した。
合成例5で得た高分子化合物(4)のPGMEA溶液14.6g、PGMEA51.2gを100mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(4)を調製した。
合成例6で得た高分子化合物(5)のPGMEA溶液14.5g、PGMEA50.7gを100mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(5)を調製した。
合成例12で得た高分子化合物(11)のPGMEA溶液15.7g、PGMEA55.1gを100mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(6)を調製した。
合成例13で得た高分子化合物(12)のPGMEA溶液14.1g、PGMEA17.7gを50mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(7)を調製した。
合成例14で得た高分子化合物(13)のPGMEA溶液14.6g、PGMEA18.2gを50mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(8)を調製した。
合成例15で得た高分子化合物(14)のPGMEA溶液82.1g、PGMEA41.0gを150mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(11)を調製した。
合成例7で得た高分子化合物(6)のPGMEA溶液10.00g、合成例8で得た高分子化合物(7)のPGMEA溶液5.93g、PGMEA55.82gを125mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(9)を調製した。塗布液(9)に含まれる高分子化合物のポリスチレン換算の数平均分子量は8.7×104であり、重量平均分子量は2.6×105であった。
合成例9で得た高分子化合物(8)の2−ヘプタノン溶液18.09g、合成例10で得た高分子化合物(9)の2−ヘプタノン溶液14.17g、2−ヘプタノン43.27gを100mLのサンプル瓶に入れ、攪拌して溶解させることにより均一な塗布液(10)を調製した。塗布液(10)に含まれる高分子化合物のポリスチレン換算の数平均分子量は6.0×104であり、重量平均分子量は1.2×105であった。
実施例7で得られた塗布液(7)を用いて、トップゲートボトムコンタクト型の有機薄膜トランジスタ(12)を製造した。以下に具体的に説明する。
具体的には、真空プロ−バ(BCT22MDC−5−HT−SCU;Nagase Electronic Equipments Service Co.,LTD製)を用いて、有機薄膜トランジスタ(12)のゲート電極に電圧を印加してゲート電圧Vgを20V〜−40Vに変化させ、ソース・ドレイン間電圧Vsdを0V〜−40Vに変化させる条件で、キャリア移動度を測定した。
結果を下記表2に示す。
ゲート絶縁層の形成に実施例9で得た塗布液(11)を用いたこと以外は実施例10と同様にして、トップゲートボトムコンタクト型の有機薄膜トランジスタ(13)を製造し、トランジスタ特性を測定し、評価した。結果を下記表2に示す。
2 ゲート電極
3 ゲート絶縁層
4 有機半導体層
5 ソース電極
6 ドレイン電極
7 オーバーコート層
10 有機薄膜トランジスタ
Claims (10)
- ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位と、
ヒドロキシ基を有する繰り返し単位、カルボキシ基を有する繰り返し単位並びにヒドロキシ基及びカルボキシ基を有する繰り返し単位を含む群から選ばれる少なくとも1種の繰り返し単位と、
下記式(1)で表される繰り返し単位とを含み、
ブロック化イソシアナト基及びブロック化イソチオシアナト基を含む群から選ばれる少なくとも1種の基を有する繰り返し単位のモル比が4〜15%である、高分子化合物。
R1、R2、R3は、互いに異なっていてもよく、水素原子、フッ素原子、又は炭素原子数1〜20の1価の有機基を表す。
R4は、水素原子、塩素原子、臭素原子、ヨウ素原子又は炭素原子数1〜20の1価の有機基を表す(ただし、フッ素原子を含む1価の有機基は除かれる。)。
Rfは、フッ素原子、又はフッ素原子を含む1価の有機基を表す。
Raは、炭素原子数1〜20の2価の有機基、−O−で表される基、−CO−で表される基、−COO−で表される基、−NHCO−で表される基、又は−NHCOO−で表される基を表し、前記−O−で表される基、前記−CO−で表される基、前記−COO−で表される基、前記−NHCO−で表される基、及び前記−NHCOO−で表される基の結合手は、前記式(1)中の前記R1が結合する炭素原子側に位置していても、前記式(1)中のベンゼン環を構成する炭素原子側に位置していてもよく、前記2価の有機基中の水素原子は、フッ素原子で置換されていてもよい。
m1は、0〜6の整数を表す。
n1は、1〜5の整数を表す。
Raが複数個ある場合、それらは互いに異なっていてもよい。R4が複数個ある場合、それらは互いに異なっていてもよい。Rfが複数個ある場合、それらは互いに異なっていてもよい。) - 前記ヒドロキシ基を有する繰り返し単位及びカルボキシ基を有する繰り返し単位が、下記式(2)で表される繰り返し単位であり、
下記式(2)で表される繰り返し単位のモル比が1〜15%である、請求項1に記載の高分子化合物。
R5、R6、R7は、互いに異なっていてもよく、水素原子、フッ素原子、又は炭素原子数1〜20の1価の有機基を表す。Rbは、炭素原子数1〜20の2価の有機基、−O−で表される基、−CO−で表される基、−COO−で表される基、−NHCO−で表される基、又は−NHCOO−で表される基を表し、前記−O−で表される基、前記−CO−で表される基、前記−COO−で表される基、前記−NHCO−で表される基、及び前記−NHCOO−で表される基の結合手は、前記式(2)中の前記R5が結合する炭素原子側に位置していても、前記式(2)中のXa側に位置していてもよい。前記2価の有機基中の水素原子は、フッ素原子で置換されていてもよい。
m2は、0〜6の整数を表す。
Xaは、ヒドロキシ基又はカルボキシ基を表す。) - 請求項1〜3のいずれか一項に記載の高分子化合物を含む組成物。
- 請求項1〜3のいずれか一項に記載の高分子化合物及び有機溶媒のみからなる、請求項4に記載の組成物。
- 請求項4又は5に記載の組成物からなる有機薄膜トランジスタの絶縁層用組成物。
- 請求項4〜6のいずれか一項に記載の組成物を硬化した膜。
- 請求項7に記載の膜をゲート絶縁層として含む、有機薄膜トランジスタ。
- 請求項7に記載の膜をオーバーコート層としてさらに含む、請求項8に記載の有機薄膜トランジスタ。
- 請求項4〜6のいずれか一項に記載の組成物を、基材の表面に塗布して塗布層を形成する工程と、
前記塗布層を硬化する工程と
を含む、有機薄膜トランジスタの製造方法。
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