WO2022102451A1 - Film de polyimide et son procédé de production - Google Patents
Film de polyimide et son procédé de production Download PDFInfo
- Publication number
- WO2022102451A1 WO2022102451A1 PCT/JP2021/040230 JP2021040230W WO2022102451A1 WO 2022102451 A1 WO2022102451 A1 WO 2022102451A1 JP 2021040230 W JP2021040230 W JP 2021040230W WO 2022102451 A1 WO2022102451 A1 WO 2022102451A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polyimide
- film
- layer
- coating film
- molecule
- Prior art date
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 185
- 238000004519 manufacturing process Methods 0.000 title claims description 35
- 239000004642 Polyimide Substances 0.000 claims abstract description 137
- 239000002243 precursor Substances 0.000 claims abstract description 21
- 239000011248 coating agent Substances 0.000 claims description 72
- 238000000576 coating method Methods 0.000 claims description 72
- 150000004985 diamines Chemical class 0.000 claims description 66
- 239000002253 acid Substances 0.000 claims description 61
- -1 alicyclic tetracarboxylic acid Chemical class 0.000 claims description 61
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims description 48
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 36
- 150000000000 tetracarboxylic acids Chemical class 0.000 claims description 33
- 239000013557 residual solvent Substances 0.000 claims description 25
- 238000010438 heat treatment Methods 0.000 claims description 22
- 238000002834 transmittance Methods 0.000 claims description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 16
- 239000004305 biphenyl Substances 0.000 claims description 15
- 235000010290 biphenyl Nutrition 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
- 239000000126 substance Substances 0.000 claims description 15
- 125000001174 sulfone group Chemical group 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 238000006068 polycondensation reaction Methods 0.000 claims description 8
- 230000003287 optical effect Effects 0.000 abstract description 6
- 150000003949 imides Chemical class 0.000 abstract 1
- 239000004615 ingredient Substances 0.000 abstract 1
- 230000001105 regulatory effect Effects 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- 229920005575 poly(amic acid) Polymers 0.000 description 34
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000314 lubricant Substances 0.000 description 20
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 12
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical group FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 11
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 230000000704 physical effect Effects 0.000 description 6
- 239000000377 silicon dioxide Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical compound NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 5
- QQGYZOYWNCKGEK-UHFFFAOYSA-N 5-[(1,3-dioxo-2-benzofuran-5-yl)oxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC=2C=C3C(=O)OC(C3=CC=2)=O)=C1 QQGYZOYWNCKGEK-UHFFFAOYSA-N 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 239000001273 butane Substances 0.000 description 5
- CURBACXRQKTCKZ-UHFFFAOYSA-N cyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1C(C(O)=O)C(C(O)=O)C1C(O)=O CURBACXRQKTCKZ-UHFFFAOYSA-N 0.000 description 5
- 125000006159 dianhydride group Chemical group 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 239000011261 inert gas Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- AIVVXPSKEVWKMY-UHFFFAOYSA-N 4-(3,4-dicarboxyphenoxy)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 AIVVXPSKEVWKMY-UHFFFAOYSA-N 0.000 description 4
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000008119 colloidal silica Substances 0.000 description 4
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 239000009719 polyimide resin Substances 0.000 description 4
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- ZMPZWXKBGSQATE-UHFFFAOYSA-N 3-(4-aminophenyl)sulfonylaniline Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=CC(N)=C1 ZMPZWXKBGSQATE-UHFFFAOYSA-N 0.000 description 3
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 3
- XPAQFJJCWGSXGJ-UHFFFAOYSA-N 4-amino-n-(4-aminophenyl)benzamide Chemical compound C1=CC(N)=CC=C1NC(=O)C1=CC=C(N)C=C1 XPAQFJJCWGSXGJ-UHFFFAOYSA-N 0.000 description 3
- ZPAKUZKMGJJMAA-UHFFFAOYSA-N Cyclohexane-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)CC1C(O)=O ZPAKUZKMGJJMAA-UHFFFAOYSA-N 0.000 description 3
- 241000209094 Oryza Species 0.000 description 3
- 235000007164 Oryza sativa Nutrition 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- BDWOQDZGSYLSCZ-UHFFFAOYSA-N [1,3]oxazolo[4,5-f][1,3]benzoxazole Chemical compound C1=C2OC=NC2=CC2=C1OC=N2 BDWOQDZGSYLSCZ-UHFFFAOYSA-N 0.000 description 3
- PMJNNCUVWHTTMV-UHFFFAOYSA-N [1,3]oxazolo[5,4-f][1,3]benzoxazole Chemical compound C1=C2OC=NC2=CC2=C1N=CO2 PMJNNCUVWHTTMV-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000002723 alicyclic group Chemical group 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 230000000149 penetrating effect Effects 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 238000012643 polycondensation polymerization Methods 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 235000009566 rice Nutrition 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WXUAQHNMJWJLTG-UHFFFAOYSA-N 2-methylbutanedioic acid Chemical compound OC(=O)C(C)CC(O)=O WXUAQHNMJWJLTG-UHFFFAOYSA-N 0.000 description 2
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 2
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 2
- GLVOXGPMYXJKGS-UHFFFAOYSA-N 4-phenoxy-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1OC1=CC=CC=C1 GLVOXGPMYXJKGS-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- WVOLTBSCXRRQFR-SJORKVTESA-N Cannabidiolic acid Natural products OC1=C(C(O)=O)C(CCCCC)=CC(O)=C1[C@@H]1[C@@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-SJORKVTESA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical compound OC1=C(C([O-])=O)C(CCCCC)=CC(O)=C1[C@H]1[C@H](C(C)=C)CCC(C)=C1 WVOLTBSCXRRQFR-DLBZAZTESA-M 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 2
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000011256 inorganic filler Substances 0.000 description 2
- 229910003475 inorganic filler Inorganic materials 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
- 229920002647 polyamide Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000003003 spiro group Chemical group 0.000 description 2
- TYFQFVWCELRYAO-UHFFFAOYSA-N suberic acid Chemical compound OC(=O)CCCCCCC(O)=O TYFQFVWCELRYAO-UHFFFAOYSA-N 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 150000003628 tricarboxylic acids Chemical class 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 2
- STIUJDCDGZSXGO-UHFFFAOYSA-N (3-amino-4-phenoxyphenyl)-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)=C1 STIUJDCDGZSXGO-UHFFFAOYSA-N 0.000 description 1
- GSHMRKDZYYLPNZ-UHFFFAOYSA-N (3-amino-4-phenoxyphenyl)-(4-amino-3-phenoxyphenyl)methanone Chemical compound NC1=CC=C(C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)C=C1OC1=CC=CC=C1 GSHMRKDZYYLPNZ-UHFFFAOYSA-N 0.000 description 1
- PHPTWVBSQRENOR-UHFFFAOYSA-N (3-amino-4-phenoxyphenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C(C=C1N)=CC=C1OC1=CC=CC=C1 PHPTWVBSQRENOR-UHFFFAOYSA-N 0.000 description 1
- YKNMIGJJXKBHJE-UHFFFAOYSA-N (3-aminophenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=CC(N)=C1 YKNMIGJJXKBHJE-UHFFFAOYSA-N 0.000 description 1
- HFAMSBMTCKNPRG-UHFFFAOYSA-N (4-amino-3-phenoxyphenyl)-(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(OC=3C=CC=CC=3)C(N)=CC=2)=C1 HFAMSBMTCKNPRG-UHFFFAOYSA-N 0.000 description 1
- NILYJZJYFZUPPO-UHFFFAOYSA-N (4-amino-3-phenoxyphenyl)-(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C(OC=2C=CC=CC=2)=C1 NILYJZJYFZUPPO-UHFFFAOYSA-N 0.000 description 1
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 1
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 1
- ARNCZJZLEMLOBH-UHFFFAOYSA-N 1-benzofuran-6-amine Chemical compound NC1=CC=C2C=COC2=C1 ARNCZJZLEMLOBH-UHFFFAOYSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- QFGCFKJIPBRJGM-UHFFFAOYSA-N 12-[(2-methylpropan-2-yl)oxy]-12-oxododecanoic acid Chemical compound CC(C)(C)OC(=O)CCCCCCCCCCC(O)=O QFGCFKJIPBRJGM-UHFFFAOYSA-N 0.000 description 1
- BEBVJSBFUZVWMS-UHFFFAOYSA-N 2-(2-methylpropyl)cyclohexane-1,4-diamine Chemical compound CC(C)CC1CC(N)CCC1N BEBVJSBFUZVWMS-UHFFFAOYSA-N 0.000 description 1
- IKSUMZCUHPMCQV-UHFFFAOYSA-N 2-(3-aminophenyl)-1,3-benzoxazol-5-amine Chemical compound NC1=CC=CC(C=2OC3=CC=C(N)C=C3N=2)=C1 IKSUMZCUHPMCQV-UHFFFAOYSA-N 0.000 description 1
- VSMRWFMFAFOGGD-UHFFFAOYSA-N 2-(3-aminophenyl)-1,3-benzoxazol-6-amine Chemical compound NC1=CC=CC(C=2OC3=CC(N)=CC=C3N=2)=C1 VSMRWFMFAFOGGD-UHFFFAOYSA-N 0.000 description 1
- IBKFNGCWUPNUHY-UHFFFAOYSA-N 2-(4-aminophenyl)-1,3-benzoxazol-6-amine Chemical compound C1=CC(N)=CC=C1C1=NC2=CC=C(N)C=C2O1 IBKFNGCWUPNUHY-UHFFFAOYSA-N 0.000 description 1
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- XQBSPQLKNWMPMG-UHFFFAOYSA-N bicyclo[2.2.2]octane-2,3,5,6-tetracarboxylic acid Chemical compound C1CC2C(C(O)=O)C(C(=O)O)C1C(C(O)=O)C2C(O)=O XQBSPQLKNWMPMG-UHFFFAOYSA-N 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- SONDVQSYBUQGDH-UHFFFAOYSA-N bis(3-amino-4-phenoxyphenyl)methanone Chemical compound NC1=CC(C(=O)C=2C=C(N)C(OC=3C=CC=CC=3)=CC=2)=CC=C1OC1=CC=CC=C1 SONDVQSYBUQGDH-UHFFFAOYSA-N 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- LRSFHOCOLGECMQ-UHFFFAOYSA-N bis(4-amino-3-phenoxyphenyl)methanone Chemical compound NC1=CC=C(C(=O)C=2C=C(OC=3C=CC=CC=3)C(N)=CC=2)C=C1OC1=CC=CC=C1 LRSFHOCOLGECMQ-UHFFFAOYSA-N 0.000 description 1
- ZLSMCQSGRWNEGX-UHFFFAOYSA-N bis(4-aminophenyl)methanone Chemical compound C1=CC(N)=CC=C1C(=O)C1=CC=C(N)C=C1 ZLSMCQSGRWNEGX-UHFFFAOYSA-N 0.000 description 1
- BBRLKRNNIMVXOD-UHFFFAOYSA-N bis[4-(3-aminophenoxy)phenyl]methanone Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)C(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 BBRLKRNNIMVXOD-UHFFFAOYSA-N 0.000 description 1
- LSDYQEILXDCDTR-UHFFFAOYSA-N bis[4-(4-aminophenoxy)phenyl]methanone Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(=O)C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 LSDYQEILXDCDTR-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- JUNWLZAGQLJVLR-UHFFFAOYSA-J calcium diphosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])(=O)OP([O-])([O-])=O JUNWLZAGQLJVLR-UHFFFAOYSA-J 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 229940043256 calcium pyrophosphate Drugs 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000002734 clay mineral Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008602 contraction Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- SMEJCQZFRMVYGC-UHFFFAOYSA-N cyclohexane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)C(C(O)=O)C1C(O)=O SMEJCQZFRMVYGC-UHFFFAOYSA-N 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- WOSVXXBNNCUXMT-UHFFFAOYSA-N cyclopentane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1CC(C(O)=O)C(C(O)=O)C1C(O)=O WOSVXXBNNCUXMT-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019821 dicalcium diphosphate Nutrition 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 229920005570 flexible polymer Polymers 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- OMGMPQSKRWSUHO-UHFFFAOYSA-N naphthalene-1,2,5-tricarboxylic acid Chemical compound OC(=O)C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OMGMPQSKRWSUHO-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 229920003207 poly(ethylene-2,6-naphthalate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011112 polyethylene naphthalate Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 230000003746 surface roughness Effects 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
- B32B27/281—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42 comprising polyimides
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/34—Layered products comprising a layer of synthetic resin comprising polyamides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/18—Manufacture of films or sheets
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
- C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2479/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2461/00 - C08J2477/00
- C08J2479/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
- C08J2479/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
Definitions
- the present invention relates to a laminated polyimide film that is colorless, has a low coefficient of linear expansion and good mechanical properties, and has no defects such as warpage, and a method for producing the same.
- Polyimide film has excellent heat resistance and good mechanical properties, and is widely used in the electric and electronic fields as a flexible material.
- a general polyimide film is colored yellowish brown, it cannot be applied to a part such as a display device that requires light transmission.
- display devices are becoming thinner and lighter, and further flexibility is required. Therefore, attempts are being made to replace the substrate material from a glass substrate with a flexible polymer film substrate, but the colored polyimide film is a substrate material for a liquid crystal display that displays by turning on / off light transmission. It cannot be used as a peripheral circuit such as a TAB or COF on which a drive circuit of a display device is mounted, or can be applied only to a small part such as the back side of a reflective display system or a self-luminous display device.
- Patent Document 4 a method of heat treatment while spraying a gas having an oxygen content has been proposed (Patent Document 4), but the manufacturing cost is high in an environment where the oxygen concentration is less than 18%, and industrial production is not possible. It's extremely difficult.
- Semi-alicyclic or full-alicyclic polyimides can obtain colorless transparency by increasing the number of monomer components having an alicyclic structure, but become hard and brittle and the elongation at break decreases, making it difficult to produce as a film. Become.
- an aromatic monomer or a monomer having an amide bond in the molecule is introduced, the toughness is increased, the mechanical properties of the film are improved, but the color is easily colored and the colorless transparency is lowered.
- an inorganic component having a refractive index close to that of the resin component heat resistance and colorless transparency are improved, the coefficient of linear expansion is further lowered, and processing suitability is improved, but the resin physical properties become hard and brittle, and the mechanical properties are descend. That is, there is a trade-off relationship between practical properties such as heat resistance and mechanical properties and colorless transparency, and it has been extremely difficult to produce a colorless transparent polyimide film that satisfies all of them.
- the present inventors tried to realize a well-balanced polyimide film by combining a plurality of polyimide resins.
- a combination of resins of a plurality of components is blended, blended, or copolymerized, it is not always possible to obtain a result in which only the good points of each component are combined, but rather the drawbacks are synergistically expressed. There are many cases of doing so.
- the present inventors have found that the advantages of each component can be fully brought out by forming each of the two component polyimides as an independent layer and forming a film.
- a multilayer polyimide film containing at least a polyimide layer (a) and a polyimide layer (b).
- the composition of the polyimide layer (a) and the polyimide layer (b) are different.
- the thickness of the polyimide layer (a) is 0.03 ⁇ m or more, and the film thickness is 0.03 ⁇ m or more.
- the film thickness of the polyimide layer (b) is more than 5 times and 500 times or less the film thickness of the polyimide layer (a).
- the polyimide of the layer (a) is a polyimide having a chemical structure obtained by polycondensation of a tetracarboxylic acid anhydride and a diamine.
- the tetracarboxylic acid anhydride contains an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond in the molecule. It is a tetracarboxylic acid anhydride containing at least one selected from the group consisting of acid dianhydride having.
- the diamine is a diamine containing at least one selected from the group consisting of a diamine having an amide bond in the molecule and a diamine having a trifluoromethyl group in the molecule.
- the polyimide of the layer (b) is a polyimide having a chemical structure obtained by polycondensation of a tetracarboxylic acid anhydride and a diamine.
- the tetracarboxylic acid anhydride contains an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond in the molecule. It is a tetracarboxylic acid anhydride containing at least one selected from the group consisting of acid dianhydride having.
- the diamine is a diamine containing at least one selected from the group consisting of a diamine having a sulfone group in the molecule and a diamine having a trifluoromethyl group in the molecule.
- the multilayer polyimide film according to any one of [1] to [3]. [5] 1: (a) A step of applying a polyimide solution for forming a layer or a polyimide precursor solution to a temporary support to obtain a coating film a1. 2: A step of drying the coating film a1 to obtain a coating film a2 having a residual solvent amount of 5 to 40% by mass.
- the functions are shared, and by setting the film thickness ratio of the two layers within a certain range, a well-balanced, that is, colorless transparency and practically sufficient film strength are achieved.
- a film having a high elongation at break and a low coefficient of linear expansion can be realized without any problems such as warpage.
- the polyimide of the layer (a) in the present invention is preferably an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an acid dianhydride having a trifluoromethyl group in the molecule.
- the polyimide of one layer (b) is preferably an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether.
- It is a polyimide having a chemical structure obtained by condensation polymerization with a diamine containing at least one selected from the group consisting of, and has high colorless transparency, but is flexible because CTE may be high. It cannot be said that the suitability for various applications is always good, and it is also difficult to produce it as a continuous film. When both are blended or copolymerized, only a film having a physical characteristic intermediate or lower than that of the film can be obtained, and the colorless transparency tends to be pulled by the characteristics of the layer (a) which is easily colored.
- the polyimides of these two components are formed as independent layers to divide the functions, and the film thickness ratio of the two layers is set within a certain range to achieve a good balance.
- a film having colorless transparency, practically sufficient film strength, high breaking elongation, and low coefficient of linear expansion can be obtained without warpage.
- the polyimide film is obtained by applying a polyimide solution or a solution of a polyimide precursor to a support, drying it, and subjecting it to a chemical reaction as necessary.
- it is two different components (a).
- the stress generated from one of the layers can be significantly reduced.
- the warp caused by the CTE difference between the layer (a) and the layer (b) is reduced, and a well-balanced film can be obtained without concentrating internal strain on a specific portion.
- the multilayer polyimide film of the present invention has a thickness of 3 ⁇ m or more and 120 ⁇ m or less. It is preferably 4 ⁇ m or more, more preferably 5 ⁇ m or more, and further preferably 8 ⁇ m or more because the mechanical properties are good. Further, it is preferably 100 ⁇ m or less, more preferably 80 ⁇ m or less, and further preferably 60 ⁇ m or less because the transparency becomes good.
- the multilayer polyimide film of the present invention has a yellow index of 5 or less. It is preferably 4 or less, more preferably 3.5 or less, and further preferably 3 or less because the transparency is good. Since the lower the yellow index is, the lower limit is not particularly limited, but industrially, it may be 0.1 or more, and 0.2 or more may be used.
- the multilayer polyimide film of the present invention has a total light transmittance of 86% or more. It is preferably 87% or more, more preferably 88% or more, and further preferably 89% or more because the transparency becomes good.
- the upper limit is not particularly limited, but industrially, it may be 99% or less, and may be 98% or less.
- polyimide is generally a polymer obtained by a polycondensation reaction between a tetracarboxylic acid anhydride and a diamine. It is preferable that the two types of polyimide layers include a layer (a) and a layer (b), and the layer (a) and the layer (b) are mainly composed of polyimides having the following characteristics.
- the polyimide having the following characteristics is preferably contained in each layer in an amount of 70% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, and particularly. It is preferably 100% by mass.
- Polyimide mainly used for the (a) layer (hereinafter, "mainly” may be omitted and simply referred to as "polyimide used for the (a) layer", “polyimide used as the (a) layer”, or the like).
- the yellow index is preferably 9 or less, more preferably 8 or less, and even more preferably 7 or less because the transparency is good.
- the lower limit of the yellow index is not particularly limited, but industrially, it may be 0.1 or more, and may be 0.2 or more.
- the total light transmittance is preferably 82% or more, more preferably 84% or more, still more preferably 86% or more.
- the upper limit is not particularly limited, but industrially, it may be 99% or less, and may be 98% or less.
- the thickness (thickness) of the (a) layer in the multilayer polyimide film needs to be 0.03 ⁇ m or more in order to obtain an independent layer without penetrating the (b) layer, and is 0.03 ⁇ m. It is preferably super, more preferably 0.04 ⁇ m or more, still more preferably 0.05 ⁇ m or more. Further, it is preferably 20 ⁇ m or less, more preferably 10 ⁇ m or less, still more preferably 7.5 ⁇ m or less, and particularly preferably 5 ⁇ m or less because the transparency is good.
- the polyimide mainly used for the layer (a) is preferably a polyimide having a chemical structure obtained by polycondensation of tetracarboxylic acid anhydride and diamine.
- the tetracarboxylic acid anhydride contains an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond in the molecule. It is preferable that it is a tetracarboxylic acid anhydride containing at least one selected from the group consisting of acid dianhydride having.
- the diamine is preferably a diamine containing at least one selected from the group consisting of a diamine having an amide bond in the molecule and a diamine having a trifluoromethyl group in the molecule.
- the amount is preferably 70 mol% or more, more preferably 80 mol% or more, still more preferably 90 mol% or more, and particularly preferably 95 mol% when the total acid component is 100 mol%.
- the total amount of the diamine having an amide bond in the molecule and the diamine having a trifluoromethyl group in the molecule is preferably 70 mol% or more, more preferably 70 mol% or more when the total diamine component is 100 mol%. It is preferably 80 mol% or more, more preferably 90 mol% or more, particularly preferably 95 mol% or more, and may be 100 mol% or more. Within the above range, the mechanical properties of the multilayer polyimide film are improved.
- Polyimide mainly used for the layer (b) (hereinafter, "mainly” may be omitted and simply referred to as "polyimide used for the layer (b)” or “polyimide used as the layer (b)”).
- the yellow index is preferably 4 or less, and more preferably 3 or less because the transparency is good.
- the lower limit of the yellow index is not particularly limited, but industrially, it may be 0.1 or more, and may be 0.2 or more.
- the total light transmittance is preferably 90% or more, more preferably 92% or more.
- the upper limit is not particularly limited, but industrially, it may be 99% or less, and may be 98% or less.
- the thickness of the layer (b) in the multilayer polyimide film is preferably 3 ⁇ m or more, more preferably 4 ⁇ m or more, still more preferably 5 ⁇ m or more, and particularly preferably 6 ⁇ m or more because the mechanical strength is good. Is. Further, it is preferably less than 120 ⁇ m, more preferably 100 ⁇ m or less, still more preferably 80 ⁇ m or less, and particularly preferably 50 ⁇ m or less because the transparency is good.
- the polyimide mainly used for the layer (b) is preferably a polyimide having a chemical structure obtained by polycondensation of tetracarboxylic acid anhydride and diamine.
- the tetracarboxylic acid anhydride contains an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond in the molecule. It is preferable that it is a tetracarboxylic acid anhydride containing at least one selected from the group consisting of acid dianhydride having.
- the diamine is preferably a diamine containing at least one selected from the group consisting of a diamine having a sulfone group in the molecule and a diamine having a trifluoromethyl group in the molecule.
- the amount is preferably 70 mol% or more, more preferably 80 mol% or more, still more preferably 90 mol% or more, and particularly preferably 95 mol% when the total acid component is 100 mol%.
- the total amount of the diamine having a sulfone group in the molecule and the diamine having a trifluoromethyl group in the molecule is preferably 70 mol% or more, more preferably 70 mol% or more when the total diamine component is 100 mol%. It is preferably 80 mol% or more, more preferably 90 mol% or more, particularly preferably 95 mol% or more, and may be 100 mol% or more. Within the above range, the transparency of the multilayer polyimide film becomes good.
- Examples of the alicyclic tetracarboxylic acid anhydride in the present invention include 1,2,3,4-cyclobutanetetracarboxylic acid, 1,2,3,4-cyclopentanetetracarboxylic acid and 1,2,3,4-cyclohexane.
- Tetracarboxylic acid 1,2,4,5-cyclohexanetetracarboxylic acid, 3,3', 4,4'-bicyclohexyltetracarboxylic acid, bicyclo [2,2,1] heptane-2,3,5,6 -Tetracarboxylic acid, bicyclo [2,2,2] octane-2,3,5,6-tetracarboxylic acid, bicyclo [2,2,2] octo-7-en-2,3,5,6-tetra Carboxylic acid, tetrahydroanthracene-2,3,6,7-tetracarboxylic acid, tetradecahydro-1,4: 5,8: 9,10-trimethanoanthracene-2,3,6,7-tetracarboxylic acid, Decahydronaphthalene-2,3,6,7-tetracarboxylic acid, decahydro-1,4: 5,8-dimethanonaphthalene-2,3,6,7-te
- dianhydride having two acid anhydride structures is preferable, and in particular, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride and 1,2,3,4-cyclohexanetetracarboxylic acid are preferable.
- Acid dianhydride, 1,2,4,5-cyclohexanetetracarboxylic acid dianhydride is preferred, 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride, 1,2,4,5-cyclohexanetetracarboxylic Acid dianhydride is more preferred, and 1,2,3,4-cyclobutanetetracarboxylic acid dianhydride is even more preferred. These may be used alone or in combination of two or more.
- the acid benzene having a biphenyl bond in the molecule is 4,4'-( 2,2-Hexafluoroisopropylidene) diphthalic acid, 4,4'-oxydiphthalic acid, bis (1,3-dioxo-1,3-dihydro-2-benzofuran-5-carboxylic acid) 1,4-phenylene, bis (1,3-Dioxo-1,3-dihydro-2-benzofuran-5-yl) Benzene-1,4-dicarboxylate, 4,4'-[4,4'-(3-oxo-1,3) -Dihydro-2-benzofuran-1,1-diyl) bis (benzene-1,4-diyloxy)] dibenzene-1,2-dicarboxylic acid, 3,3', 4,4'
- Acid dianhydrides having a trifluoromethyl group in the molecule include 4,4'-(2,2-hexafluoroisopropylidene) diphthalic acid dianhydride and 1,4-di (trifluoromethyl) pyromerit. Acid dianhydride, 1,4-di (pentafluoroethyl) pyromellitic acid dianhydride and the like can be mentioned.
- Acid dianhydrides having an ether bond in the molecule include 4,4'-oxydiphthalic acid anhydride, 4,4'-(4,4'-isopropylidene diphenoxy) diphthalic acid anhydride, 4,4-[ 4,4- (Propane-2,2-diyl) diphenoxy] Diphthalic acid dianhydride and the like can be mentioned.
- tricarboxylic acid and dicarboxylic acid may be used in addition to tetracarboxylic acid anhydride.
- tricarboxylic acids include aromatic tricarboxylic acids such as trimellitic acid, 1,2,5-naphthalene tricarboxylic acid, diphenyl ether-3,3', 4'-tricarboxylic acid, and diphenylsulfone-3,3', 4'-tricarboxylic acid.
- An acid or an alkylene such as a hydrogenated additive of the above aromatic tricarboxylic acid such as hexahydrotrimeric acid, ethylene glycol bistrimericte, propylene glycol bistrimerite, 1,4-butanediol bistrimerite and polyethylene glycol bistrimerite.
- monoanhydride having one acid anhydride structure is preferable, and in particular, trimellitic acid anhydride and hexahydrotrimellitic acid anhydride are preferable. These may be used alone or in combination of two or more.
- dicarboxylic acids examples include aromatic dicarboxylic acids such as terephthalic acid, isophthalic acid, orthophthalic acid, naphthalenedicarboxylic acid, 4,4'-oxydibenzenecarboxylic acid, and the above aromatic dicarboxylic acid such as 1,6-cyclohexanedicarboxylic acid.
- Hydrogen additives oxalic acid, succinic acid, glutaric acid, adipic acid, heptanedioic acid, octanedioic acid, azelaioic acid, sebacic acid, undecadioic acid, dodecanedioic acid, 2-methylsuccinic acid, and acid acidates thereof.
- an esterified product or the like can be mentioned.
- aromatic dicarboxylic acids and hydrogen additives thereof are preferable, and terephthalic acid, 1,6-cyclohexanedicarboxylic acid, and 4,4'-oxydibenzenecarboxylic acid are particularly preferable.
- the dicarboxylic acids may be used alone or in combination of two or more.
- aromatic diamines and alicyclic amines can be mainly used.
- aromatic diamines include 2,2'-dimethyl-4,4'-diaminobiphenyl, 1,4-bis [2- (4-aminophenyl) -2-propyl] benzene, and 1,4-bis.
- a part or all of the hydrogen atoms on the aromatic ring of the aromatic diamine may be substituted with a halogen atom, an alkyl group or an alkoxyl group having 1 to 3 carbon atoms, or a cyano group, and further, the carbon number 1 may be substituted.
- a part or all of the hydrogen atom of the alkyl group or the alkoxyl group of ⁇ 3 may be substituted with a halogen atom.
- alicyclic diamines examples include 1,4-diaminocyclohexane, 1,4-diamino-2-methylcyclohexane, 1,4-diamino-2-ethylcyclohexane, and 1,4-diamino-2-n-propyl.
- diamine having a sulfone group in the molecule examples include 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl sulfone and the like.
- the (a) layer polyimide and the (b) layer polyimide have a structure of two or more layers (a) / (b), and the (b) layer is on an upper layer, that is, a surface (air surface) in contact with air. It is preferable to arrange it so that it is located.
- the layer (a) which has a smaller coefficient of linear expansion than the layer (b), as the lower layer, that is, the surface in contact with the coating support, the handling of the film is improved and the (b) layer polyimide as the upper layer is excellent. The optical characteristics can be maximized.
- the layer (b) is preferably thicker than the layer (a).
- the multilayer polyimide film of the present invention may have a multilayer structure of three or more layers.
- a three-layer structure of (a) layer / (b) layer / (a) layer, a four-layer structure of (a) layer / (b) layer / (a) layer / (b) layer, (a) layer / It may have a five-layer structure of (b) layer / (a) layer / (b) layer / (a) layer.
- layers other than the layer (a) and the layer (b) may be laminated.
- the third resin layer (c), the fourth resin layer (d), and the like may be inserted into any layer as long as the effects of the present invention are not impaired.
- the composition and surface roughness of both sides may be changed.
- the thickness of the layer (a) is preferably 0.03 ⁇ m or more, preferably 0.05 ⁇ m or more, more preferably 0.1 ⁇ m or more, still more preferably 0.5 ⁇ m or more. Is preferable.
- the thickness of the laminated layers (a) and (b) can be measured by cutting the film diagonally in the thickness direction and observing the composition distribution of the polyimide.
- the polyimide used for the layer (a) in the present invention is preferably a polyimide having a yellow index of 10 or less and a total light transmittance of 80% or more when a film having a thickness of 25 ⁇ 2 ⁇ m is used alone. .. Further, the polyimide used for the layer (a) preferably has a CTE of 30 ppm / K or less, more preferably 20 ppm / K or less, a tensile breaking strength of 120 MPa or more, further preferably 140 MPa or more, and a breaking elongation. It is preferably 8% or more, more preferably 10% or more.
- Preferred polyimides for the layer (a) include an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond.
- An example thereof is a polyimide having a chemical structure obtained by condensation polymerization with a diamine containing one or more of the selected substances. By adopting these configurations, coloring is suppressed.
- the diamine having an amide bond in the molecule 4-amino-N- (4-aminophenyl) benzamide is preferable.
- a diamine having an amide bond is used, it is preferably 70 mol% or more, more preferably 80 mol% or more, and further preferably 90 mol% or more of the total diamine.
- the diamine having a trifluoromethyl group in the molecule include 2,2'-ditrifluoromethyl-4,4'-diaminobiphenyl and 1,4-bis (4-amino-2-trifluoromethylphenoxy) benzene. , 2,2'-Trifluoromethyl-4,4'-diaminodiphenyl ether is preferred.
- the amount used is preferably 70 mol% or more, more preferably 80 mol% or more, and further, 80 mol% or more of the total diamine. Is preferably used in an amount of 90 mol% or more.
- the polyimide used for the layer (b) in the present invention is preferably a polyimide having a yellow index of 5 or less and a total light transmittance of 85% or more when a film having a thickness of 25 ⁇ 2 ⁇ m is used alone. ..
- the polyimide used for the layer (b) includes an alicyclic tetracarboxylic acid anhydride, an acid dianhydride having a biphenyl bond in the molecule, an acid dianhydride having a trifluoromethyl group in the molecule, and an ether bond.
- aromatic tetracarboxylic acid anhydride preferably used for the polyimide of the layer (b)
- 4,4'-oxydiphthalic acid, pyromellitic acid, and 3,3', 4,4'-biphenyltetracarboxylic acid are preferable.
- aromatic tetracarboxylic acid dianhydride used for the (b) layer polyimide it is preferably 30 mol% or more, more preferably 50 mol% or more of the total tetracarboxylic acid of the (b) layer polyimide. .. Transparency is improved by keeping the content of the aromatic tetracarboxylic acid within a predetermined range.
- tetracarboxylic acid containing a trifluoromethyl group used in the polyimide of the layer (b) in the molecule 4,4'-(2,2-hexafluoroisopropylidene) diphthalic acid dianhydride is preferable.
- a tetracarboxylic acid containing a trifluoromethyl group used in the (b) layer polyimide is used, 30 mol% or more of the total tetracarboxylic acid in the (b) layer polyimide is preferable, and more preferably 50. More than mol%. Colorless transparency is improved by keeping the content of the tetracarboxylic acid containing a trifluoromethyl group in the molecule within a predetermined range.
- the diamine preferably used is a diamine having at least a sulfone group in the molecule and / or a diamine having a trifluoromethyl group in the molecule.
- the diamine having a sulfone group in the molecule 3,3'-diaminodiphenyl sulfone, 3,4'-diaminodiphenyl sulfone, and 4,4'-diaminodiphenyl sulfone can be used.
- a diamine containing 70 mol% or more, preferably 80 mol% or more, more preferably 90 mol% or more of a diamine having a sulfone group in the molecule is used in combination with the aromatic tetracarboxylic acid anhydride. Colorless transparency can also be obtained in some cases.
- Diamines having a trifluoromethyl group include 4,4'-diamino-2,2'-bis (trifluoromethyl) biphenyl, 2,2'-ditrifluoromethyl-4,4'-diaminobiphenyl, 1,4.
- -Bis (4-amino-2-trifluoromethylphenoxy) benzene, 2,2'-trifluoromethyl-4,4'-diaminodiphenyl ether is preferred.
- the amount used is preferably 70 mol% or more, 80 mol% or more, and further 90 in the total diamine. It is preferable to use mol% or more.
- the polyimide of the layer (a) and the polyimide of the layer (b) in the present invention are characterized by the yellow index, total light transmittance, mechanical properties, etc. when a film having a thickness of 25 ⁇ 2 ⁇ m is used alone.
- the operation of forming a film having a thickness of 25 ⁇ 2 ⁇ m alone here is an evaluation of a scale possible in the laboratory, and the polyimide solution or the polyimide precursor solution has a size of 10 cm square, preferably 20 cm square or more. It is applied to a glass plate, first preheated at a temperature of up to 120 ° C., preheated and dried until the amount of residual solvent is 40% by mass or less of the coating film, and then at 300 ° C.
- the polyimide of the (a) layer and the polyimide of the (b) layer in the present invention can each contain a lubricant (filler).
- the lubricant may be an inorganic filler or an organic filler, but an inorganic filler is preferable.
- the lubricant is not particularly limited, and examples thereof include silica, carbon, and ceramic, and silica is preferable. These lubricants may be used alone or in combination of two or more.
- the average particle size of the lubricant is preferably 10 nm or more, more preferably 30 nm or more, still more preferably 50 nm or more. Further, it is preferably 1 ⁇ m or less, more preferably 500 nm or less, still more preferably 100 nm or less.
- the content of the lubricant in the polyimide of the layer (a) and the polyimide of the layer (b) is preferably 0.01% by mass or more with respect to the polymer mass. Since the smoothness of the polyimide film is good, it is more preferably 0.02% by mass or more, further preferably 0.05% by mass or more, and particularly preferably 0.1% by mass or more. Further, from the viewpoint of enhancing heat resistance, it is also good to add 20% by mass or more. From the viewpoint of transparency, it is preferably 50% by mass or less, more preferably 30% by mass or less, further preferably 10% by mass or less, and particularly preferably 5% by mass or less.
- the method for producing a multilayer polyimide film of the present invention is 1: (a) A step of applying a polyimide solution for forming a layer or a polyimide precursor solution to a temporary support to obtain a coating film a1. 2: A step of drying the coating film a1 to obtain a coating film a2 having a residual solvent amount of 5 to 40% by mass. 3: (b) A step of applying a polyimide solution for forming a layer or a polyimide precursor solution to the coating film a2 to obtain the coating film ab1.
- the amount of residual solvent in the step 2 is preferably 8% by mass or more and 35% by mass or less, and more preferably 10% by mass or more and 30% by mass or less.
- the polyimide precursor solution is used in the step 1, it is preferable to carry out the imidization reaction in the drying step 4 (operation of reducing the residual solvent amount to 0.5% by mass or less).
- the temporary support is preferably long and flexible.
- the residual solvent amount based on all layers in the second step shall be obtained from the mass of only the coating film ab1 and shall not include the mass of the temporary support. The same applies to the following operations.
- the method for producing a multilayer polyimide film of the present invention is Preferably, in the atmosphere or an inert gas having a temperature of 10 ° C. or higher and 40 ° C. or lower and a humidity of 10% or higher and 55% or lower, 1: (a) a polyimide solution for forming a layer or a polyimide precursor solution is temporarily supported.
- the amount of residual solvent in the steps 2 and 4 is preferably 8% by mass or more and 35% by mass or less, and more preferably 10% by mass or more and 30% by mass or less. Further, when the polyimide precursor solution is used in the step 1, it is preferable to carry out the imidization reaction in the drying step 5 (operation of reducing the residual solvent amount to 0.5% by mass or less).
- the coating film ab3 peeled off from the temporary support in the step 5 becomes a self-supporting film. Then, when the coating film ab3 is heated in the step 6, it is preferable to grip both ends of the coating film ab3 (self-supporting film).
- the temporary support is preferably long and flexible.
- the residual solvent amount based on all layers in the second step shall be obtained from the mass of only the coating film ab1 and shall not include the mass of the temporary support.
- the application of the polyimide solution or the polyimide precursor solution is performed at a temperature of 10 ° C. or higher and 40 ° C. or lower, preferably 15 ° C. or higher and 35 ° C. or lower, and a humidity of 10% RH or higher and 55% RH or lower, preferably 20% RH or higher. It is preferably carried out on a long and flexible temporary support in the atmosphere of 50% RH or in an inert gas.
- the first layer to be applied can be applied using a comma coater, a bar coater, a slit coater, or the like, and the second and subsequent layers can be applied by a die coater, a curtain coater, a spray coater, or the like. .. It is also possible to apply these plurality of layers substantially at the same time by using a multilayer die.
- the environment for applying the solution is preferably in the atmosphere or in an inert gas.
- the inert gas may be interpreted as a gas having a substantially low oxygen concentration, and nitrogen or carbon dioxide may be used from an economical point of view.
- the temporary support used in the present invention glass, a metal plate, a metal belt, a metal drum, a polymer film, a metal foil, or the like can be used.
- a film such as polyethylene terephthalate, polyethylene naphthalate, or polyimide can be used as the temporary support. It is one of the preferable embodiments to perform a mold release treatment on the surface of the temporary support.
- the polyimide precursor is preferably in the form of polyamic acid or polyisoimide.
- a dehydration condensation reaction is required to convert polyamic acid to polyimide.
- the dehydration condensation reaction can be carried out only by heating, but an imidization catalyst can also be allowed to act if necessary. Even in the case of polyisoimide, conversion from an isoimide bond to an imide bond can be performed by heating.
- the amount of residual solvent in the final film is 0.5% by mass or less, preferably 0.2% by mass or less, and more preferably 0.08% by mass or less as an average value of all layers of the film.
- the heating time is preferably 5 minutes or more and 60 minutes or less, preferably 6 minutes or more and 50 minutes or less, and more preferably 7 minutes or more and 30 minutes or less. By keeping the heating time within a predetermined range, it is possible to remove the solvent, complete the necessary chemical reaction, reduce the warp of the film, and keep the colorless transparency, mechanical properties, especially the elongation at break. Can be done. If the heating time is short, the warp of the film becomes large, and if the heating time is longer than necessary, the film coloring becomes stronger and the breaking elongation of the film may decrease.
- the applied solution dries or undergoes a chemical reaction by heating and is self-supporting and can be peeled off from the temporary support, it may be peeled off from the temporary support during the heating step. More specifically, it takes 5 minutes or more and 45 minutes or less, preferably 6 minutes or more and 30 minutes or less, and more preferably 7 minutes or more until the average residual solvent amount of all film layers reaches the range of 15% by mass or more and 40% by mass or less. After heating for 20 minutes or less, the self-supporting film is peeled off from the temporary support.
- the self-supporting film may be stretched.
- the stretching may be in either the longitudinal direction of the film (MD direction) or the width direction (TD) of the film, or both.
- Stretching in the longitudinal direction of the film can be performed by using the speed difference of the transport roll or the difference in speed between the transport roll and the speed after gripping both ends.
- Stretching in the film width direction can be performed by widening the gripped clip or pin. Stretching and heating may be performed at the same time.
- the draw ratio can be arbitrarily selected from 1.00 times to 2.5 times.
- a polyimide that is difficult to stretch by itself and a polyimide that can be stretched can be combined to enable the polyimide to be stretched to a composition that is difficult to stretch, that is, easily broken by stretching.
- Mechanical properties can be improved. Since the volume of polyimide becomes smaller during film formation due to drying or dehydration condensation, the stretching effect is exhibited even when both ends are gripped at equal intervals (stretching ratio is 1.00 times).
- a lubricant is added and contained in the polyimide to impart fine irregularities on the surface of the layer (film) to improve the slipperiness of the film. Is preferable.
- the lubricant is preferably added only to the outer layer (a).
- fine particles having an average particle size of about 0.03 ⁇ m to 3 ⁇ m of inorganic or organic can be used, and specific examples thereof include titanium oxide, alumina, silica, calcium carbonate, calcium phosphate, calcium hydrogen phosphate, calcium pyrophosphate, and the like. Examples include magnesium oxide, calcium oxide and clay minerals.
- the content of the lubricant is preferably 0.01% by mass or more with respect to the polymer mass. Since the smoothness of the polyimide film is good, it is more preferably 0.02% by mass or more, further preferably 0.05% by mass or more, and particularly preferably 0.1% by mass or more. Further, from the viewpoint of enhancing heat resistance, it is also good to add 20% by mass or more. From the viewpoint of transparency, it is preferably 50% by mass or less, more preferably 30% by mass or less, further preferably 10% by mass or less, and particularly preferably 5% by mass or less.
- ⁇ Tension modulus, tensile strength (breaking strength), and breaking elongation> The film was cut into strips of 100 mm ⁇ 10 mm in the flow direction (MD direction) and the width direction (TD direction) at the time of coating, and used as test pieces.
- Tensile tester manufactured by Shimadzu, Autograph (R) model name AG-5000A
- the tensile elastic modulus and tensile strength are obtained in each of the MD and TD directions under the conditions of a tensile speed of 50 mm / min and a chuck distance of 40 mm.
- the elongation at break were obtained, and the average value of the measured values in the MD direction and the TD direction was obtained.
- CTE Coefficient of linear expansion
- ⁇ Film thickness> A diagonally cut surface of the film was prepared by SAICAS DN-20S type (Dipla Wintes), and then this diagonally cut surface was microscopically ATR using germanium crystals (incident angle 30 °) by microscopic IR Cary 620 FTIR (Agilent). The spectrum is obtained by the method, and the ratio of (b) layer film thickness / (a) layer film thickness is obtained from the increase / decrease of the characteristic peaks of each of the (a) layer and (b) layer and the calibration curve obtained in advance. rice field.
- ⁇ Haze> The haze of the film was measured using HAZEMETER (NDH5000, manufactured by Nippon Denshoku Co., Ltd.). A D65 lamp was used as the light source. The same measurement was performed three times, and the arithmetic mean value was adopted.
- TT total light transmittance
- HAZEMETER Nippon Denshoku Co., Ltd.
- a D65 lamp was used as the light source.
- the same measurement was performed three times, and the arithmetic mean value was adopted.
- ⁇ Film warp> A film cut into a square having a size of 100 mm ⁇ 100 mm is used as a test piece, and the test piece is allowed to stand on a flat surface at room temperature so as to be concave, and the distances from the flat surface at the four corners (h1rt, h2rt, h3rt, h4rt: unit mm). ) was measured, and the average value was taken as the amount of warpage (mm).
- a polyamic acid solution A having an NV (solid content) of 10% by mass and a reduction viscosity of 3.10 dl / g.
- Silica (lubricant) is added to the obtained polyamic acid solution A with a dispersion (“Snowtex (registered trademark) DMAC-ST-ZL” manufactured by Nissan Chemical Industries, Ltd.) in which colloidal silica is further dispersed in dimethylacetamide as a lubricant.
- the total amount of polymer solids in the polyamic acid solution was 1.4% by mass), and a uniform polyamic acid solution As was obtained.
- a polyamic acid solution B having a solid content of 14% by mass and a reduction viscosity of 2.50 dl / g was obtained.
- a dispersion obtained by dispersing colloidal silica as a lubricant in dimethylacetamide (“Snowtex (registered trademark) DMAC-ST-ZL” manufactured by Nissan Chemical Industries, Ltd.) and silica (slipper) is a polyamide.
- the total amount of polymer solids in the acid solution was 0.45% by mass), and a uniform polyamic acid solution Bs was obtained.
- a polyamic acid solution C having a solid content of 13.5% by mass and a reduction viscosity of 2.80 dl / g.
- the obtained polyamic acid solution C is mixed with a dispersion (“Snowtex (registered trademark) DMAC-ST-ZL” manufactured by Nissan Chemical Industries, Ltd.) in which colloidal silica is dispersed in dimethylacetamide as a lubricant, and silica (slipper) is a polyamide.
- the total amount of polymer solids in the acid solution was 0.5% by mass), and a uniform polyamic acid solution Cs was obtained.
- BPDA diphenyl-3,3', 4,4'-tetracarboxylic acid dianhydride
- ODPA 4,4'-oxydiphthalic acid dianhydride
- the polyimide solution and the polyamic acid solution (polyimide precursor solution) obtained in Production Examples 1 to 7 were formed into a film by the following method, and the optical properties and mechanical properties were measured. The results are shown in Table 1. (How to obtain a film for measuring physical properties by itself) A polyimide solution or a polyamic acid solution was applied to the center of a glass plate having a side of 30 cm, approximately 20 cm square, using a bar coater so that the final thickness was 25 ⁇ 2 ⁇ m, and dry nitrogen was gently poured. After heating in an inert oven at 100 ° C.
- a muffle furnace replaced with dry nitrogen is used at 300 ° C. for 20 minutes. Heated. Then, it is taken out from the muffle furnace, the end of the dry coating film (film) is raised with a utility knife, and it is carefully peeled from the glass to obtain a film.
- Example 1 In the air air-conditioned at 25 ° C. and 45% RH, the polyamic acid solution As obtained in Production Example 1 was prepared by using a polyethylene terephthalate film A4100 (manufactured by Toyobo Co., Ltd., hereinafter abbreviated as PET film) using a comma coater. The film was applied onto the non-slip material surface so that the final film thickness was 0.8 ⁇ m, and dried at 110 ° C. for 5 minutes. Subsequently, the polyimide solution D obtained in Production Example 4 was applied onto the polyamic acid solution As with a die coater so that the final film thickness was 25 ⁇ m, and this was dried at 110 ° C. for 10 minutes.
- PET film polyethylene terephthalate film A4100 (manufactured by Toyobo Co., Ltd., hereinafter abbreviated as PET film) using a comma coater. The film was applied onto the non-slip material surface so that the final
- the self-supporting film after drying is peeled off from the A4100 film that has been used as a support, passed through a pin tenter having a pin sheet on which pins are arranged, and the film end is gripped by inserting it into the pins so that the film does not break. And, the pin sheet spacing is adjusted so that unnecessary slack does not occur, and the film is transported, and heated at 200 ° C for 3 minutes, 250 ° C for 3 minutes, and 300 ° C for 6 minutes to proceed with the imidization reaction. rice field.
- the film was cooled to room temperature in 2 minutes, and the portions of the film having poor flatness were cut off with a slitter and wound into a roll to obtain a roll of the film having a width of 580 mm and a length of 100 m.
- the evaluation results of the obtained film are shown in Table 2.
- the polyamic acid solution As obtained in Production Example 1 was prepared by using a polyethylene terephthalate film A4100 (manufactured by Toyobo Co., Ltd., hereinafter abbreviated as PET film) using a comma coater. The film was applied onto the non-slip material surface so that the final film thickness was 5.0 ⁇ m, and dried at 110 ° C. for 5 minutes. Subsequently, the polyimide solution D obtained in Production Example 4 was applied onto the polyamic acid solution As with a die coater so that the final film thickness was 25 ⁇ m, and this was dried at 110 ° C. for 10 minutes.
- PET film polyethylene terephthalate film A4100 (manufactured by Toyobo Co., Ltd., hereinafter abbreviated as PET film) using a comma coater. The film was applied onto the non-slip material surface so that the final film thickness was 5.0 ⁇ m, and dried at 110 ° C. for 5 minutes
- the self-supporting film after drying is peeled off from the A4100 film that has been used as a support, passed through a pin tenter having a pin sheet on which pins are arranged, and the film end is gripped by inserting it into the pins so that the film does not break.
- the pin sheet spacing is adjusted and transported so that unnecessary slack does not occur, and the film is heated at 200 ° C for 3 minutes, 250 ° C for 3 minutes, and 300 ° C for 6 minutes to proceed with the imidization reaction. rice field.
- the film was cooled to room temperature in 2 minutes, and the portions of the film having poor flatness were cut off with a slitter and wound into a roll to obtain a film roll having a width of 580 mm and a length of 100 m.
- the evaluation results of the obtained film are shown in Table 2.
- Comparative Example 2 The polyamic acid solution As of Comparative Example 1 was changed to the polyamic acid solution Bs, and the film was applied so that the final film thickness was 0.05 ⁇ m. Then, 10 seconds later, the polyimide solution D obtained in Production Example 4 was used as the polyamic acid solution Bs. A film roll having a width of 580 mm and a length of 100 m was obtained by performing the same operation as in Comparative Example 1 except that the film was applied onto the film with a die coater so that the final film thickness was 30.0 ⁇ m. The evaluation results of the obtained film are shown in Table 2.
- Comparative Example 3 The polyamic acid solution As of Comparative Example 1 was changed to the polyamic acid solution Bs, and the film was applied so that the final film thickness was 0.02 ⁇ m. Then, 10 seconds later, the polyimide solution D obtained in Production Example 4 was used as the polyamic acid solution Cs. A film roll having a width of 580 mm and a length of 100 m was obtained by performing the same operation as in Comparative Example 1 except that the film was applied onto the film with a die coater so that the final film thickness was 8.0 ⁇ m. The evaluation results of the obtained film are shown in Table 2.
- the multilayer polyimide film of the present invention is balanced by forming the two-component polyimides as independent layers to divide the functions and setting the film thickness ratio of the two layers within a certain range. It is possible to obtain a film having a clear color, that is, colorless transparency, practically sufficient film strength, high breaking elongation, and a low coefficient of linear expansion, without any problems such as warpage.
- the multilayer polyimide film of the present invention has excellent optical properties, colorless transparency, excellent mechanical properties, and exhibits a relatively low CTE. Therefore, it is necessary to use it as a member of a flexible and lightweight display device or to have transparency. It can be used for switch elements such as touch panels and pointing devices.
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- Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
- Moulding By Coating Moulds (AREA)
Abstract
La présente invention permet d'obtenir, sans aucun problème de type déformation, un film présentant une combinaison bien équilibrée de propriétés en matière de couleur et de transparence, de résistance de film suffisante dans la pratique, d'allongement élevé à la rupture et de faible coefficient de dilatation linéaire, et ce, en façonnant deux ingrédients polyimidiques sous la forme de couches indépendantes correspondantes en vue de l'attribution de fonctions et en régulant le rapport d'épaisseur du film entre les deux couches sur une valeur se situant dans une certaine plage. Ce film est un film à deux couches composé d'un polyimide à haute résistance en tant que couche interne (a) et d'un polyimide présentant d'excellentes propriétés optiques en tant que couche externe (b). Des solutions de polyimide ou de précurseur de polyimide pour constituer les deux couches sont appliquées sur un support temporaire et traitées thermiquement pour former ledit film d'imide. Les deux couches sont combinées de telle sorte que l'une des deux couches est beaucoup plus mince que l'autre, ce qui permet d'obtenir un film sans déformation et qui est incolore et transparent.
Priority Applications (3)
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KR1020237011998A KR20230098789A (ko) | 2020-11-10 | 2021-11-01 | 폴리이미드 필름 및 그 제조 방법 |
JP2022523343A JPWO2022102451A1 (fr) | 2020-11-10 | 2021-11-01 | |
CN202180057843.3A CN116137837A (zh) | 2020-11-10 | 2021-11-01 | 聚酰亚胺膜及其制造方法 |
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PCT/JP2021/040230 WO2022102451A1 (fr) | 2020-11-10 | 2021-11-01 | Film de polyimide et son procédé de production |
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JP (1) | JPWO2022102451A1 (fr) |
KR (1) | KR20230098789A (fr) |
CN (1) | CN116137837A (fr) |
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WO (1) | WO2022102451A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
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CN115058040A (zh) * | 2022-06-23 | 2022-09-16 | 华中科技大学 | 一种双层聚酰亚胺薄膜及其制备方法和应用 |
CN115141372A (zh) * | 2022-08-08 | 2022-10-04 | 波米科技有限公司 | 一种聚酰亚胺类物质及其应用 |
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WO2016129329A1 (fr) * | 2015-02-09 | 2016-08-18 | コニカミノルタ株式会社 | Procédé de fabrication d'un film stratifié transparent résistant à la chaleur, film stratifié transparent résistant à la chaleur, carte de circuit imprimé souple, substrat pour affichage souple, plaque avant pour affichage souple, dispositif d'éclairage à led, et dispositif d'affichage électroluminescent organique |
WO2018186262A1 (fr) * | 2017-04-06 | 2018-10-11 | 大日本印刷株式会社 | Film polyimide, stratifié, et matériau de surface pour afficheur |
JP2019515819A (ja) * | 2016-12-27 | 2019-06-13 | エルジー・ケム・リミテッド | プラスチック積層フィルム |
WO2020262450A1 (fr) * | 2019-06-27 | 2020-12-30 | 日鉄ケミカル&マテリアル株式会社 | Film de résine, stratifié plaqué de métal et procédé pour sa production |
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JP3425854B2 (ja) | 1997-10-02 | 2003-07-14 | 日本電信電話株式会社 | 低屈折率透明ポリイミド共重合体、及びそれらの前駆体溶液、及びそれらの製造方法 |
JP2002146021A (ja) | 2000-11-10 | 2002-05-22 | Ube Ind Ltd | 可溶性、透明なポリイミドおよびその製造法 |
JP2002348374A (ja) | 2001-05-25 | 2002-12-04 | Hitachi Cable Ltd | ポリアミック酸又はポリイミド及び液晶配向剤 |
KR101423361B1 (ko) | 2007-05-24 | 2014-07-24 | 미츠비시 가스 가가쿠 가부시키가이샤 | 무색 투명 수지 필름의 제조 방법 및 제조 장치 |
-
2021
- 2021-11-01 WO PCT/JP2021/040230 patent/WO2022102451A1/fr active Application Filing
- 2021-11-01 JP JP2022523343A patent/JPWO2022102451A1/ja active Pending
- 2021-11-01 KR KR1020237011998A patent/KR20230098789A/ko unknown
- 2021-11-01 CN CN202180057843.3A patent/CN116137837A/zh active Pending
- 2021-11-03 TW TW110140901A patent/TW202222914A/zh unknown
Patent Citations (4)
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WO2016129329A1 (fr) * | 2015-02-09 | 2016-08-18 | コニカミノルタ株式会社 | Procédé de fabrication d'un film stratifié transparent résistant à la chaleur, film stratifié transparent résistant à la chaleur, carte de circuit imprimé souple, substrat pour affichage souple, plaque avant pour affichage souple, dispositif d'éclairage à led, et dispositif d'affichage électroluminescent organique |
JP2019515819A (ja) * | 2016-12-27 | 2019-06-13 | エルジー・ケム・リミテッド | プラスチック積層フィルム |
WO2018186262A1 (fr) * | 2017-04-06 | 2018-10-11 | 大日本印刷株式会社 | Film polyimide, stratifié, et matériau de surface pour afficheur |
WO2020262450A1 (fr) * | 2019-06-27 | 2020-12-30 | 日鉄ケミカル&マテリアル株式会社 | Film de résine, stratifié plaqué de métal et procédé pour sa production |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
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CN115058040A (zh) * | 2022-06-23 | 2022-09-16 | 华中科技大学 | 一种双层聚酰亚胺薄膜及其制备方法和应用 |
CN115058040B (zh) * | 2022-06-23 | 2023-10-03 | 华中科技大学 | 一种双层聚酰亚胺薄膜及其制备方法和应用 |
CN115141372A (zh) * | 2022-08-08 | 2022-10-04 | 波米科技有限公司 | 一种聚酰亚胺类物质及其应用 |
CN115141372B (zh) * | 2022-08-08 | 2024-01-26 | 波米科技有限公司 | 一种聚酰亚胺类物质及其应用 |
Also Published As
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TW202222914A (zh) | 2022-06-16 |
JPWO2022102451A1 (fr) | 2022-05-19 |
CN116137837A (zh) | 2023-05-19 |
KR20230098789A (ko) | 2023-07-04 |
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