JP6900152B2 - ガラス代替材料用のフィルム - Google Patents
ガラス代替材料用のフィルム Download PDFInfo
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- JP6900152B2 JP6900152B2 JP2016077504A JP2016077504A JP6900152B2 JP 6900152 B2 JP6900152 B2 JP 6900152B2 JP 2016077504 A JP2016077504 A JP 2016077504A JP 2016077504 A JP2016077504 A JP 2016077504A JP 6900152 B2 JP6900152 B2 JP 6900152B2
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- film
- polyimide
- dianhydride
- bis
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- 239000000463 material Substances 0.000 title claims description 16
- 239000011521 glass Substances 0.000 title claims description 15
- 229920001721 polyimide Polymers 0.000 claims description 137
- 239000004642 Polyimide Substances 0.000 claims description 82
- 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 67
- 239000002253 acid Substances 0.000 claims description 47
- 229920005575 poly(amic acid) Polymers 0.000 claims description 42
- 150000004985 diamines Chemical class 0.000 claims description 41
- 239000002243 precursor Substances 0.000 claims description 28
- 238000002834 transmittance Methods 0.000 claims description 16
- 230000009477 glass transition Effects 0.000 claims description 14
- 125000002723 alicyclic group Chemical group 0.000 claims description 10
- 239000000178 monomer Substances 0.000 claims description 10
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 claims description 7
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000006159 dianhydride group Chemical group 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- 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 claims description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 claims 1
- CQMIJLIXKMKFQW-UHFFFAOYSA-N 4-phenylbenzene-1,2,3,5-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C(O)=O)=C1C1=CC=CC=C1 CQMIJLIXKMKFQW-UHFFFAOYSA-N 0.000 claims 1
- 239000010408 film Substances 0.000 description 82
- 239000000243 solution Substances 0.000 description 64
- 239000002904 solvent Substances 0.000 description 61
- 238000000034 method Methods 0.000 description 52
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 30
- 230000015572 biosynthetic process Effects 0.000 description 29
- 239000009719 polyimide resin Substances 0.000 description 25
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
- 238000003786 synthesis reaction Methods 0.000 description 24
- -1 polyethylene terephthalate Polymers 0.000 description 23
- 239000000203 mixture Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- 238000001035 drying Methods 0.000 description 19
- 239000003054 catalyst Substances 0.000 description 18
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- 239000012299 nitrogen atmosphere Substances 0.000 description 15
- 238000005259 measurement Methods 0.000 description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000012024 dehydrating agents Substances 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- NVKGJHAQGWCWDI-UHFFFAOYSA-N 4-[4-amino-2-(trifluoromethyl)phenyl]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F NVKGJHAQGWCWDI-UHFFFAOYSA-N 0.000 description 11
- 238000006116 polymerization reaction Methods 0.000 description 9
- 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 8
- 239000012298 atmosphere Substances 0.000 description 8
- 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 8
- 238000000576 coating method Methods 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000002985 plastic film Substances 0.000 description 7
- 229920006255 plastic film Polymers 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- QYIMZXITLDTULQ-UHFFFAOYSA-N 4-(4-amino-2-methylphenyl)-3-methylaniline Chemical compound CC1=CC(N)=CC=C1C1=CC=C(N)C=C1C QYIMZXITLDTULQ-UHFFFAOYSA-N 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002798 polar solvent Substances 0.000 description 5
- LJMPOXUWPWEILS-UHFFFAOYSA-N 3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1C2C(=O)OC(=O)C2CC2C(=O)OC(=O)C21 LJMPOXUWPWEILS-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
- WKDNYTOXBCRNPV-UHFFFAOYSA-N bpda Chemical compound C1=C2C(=O)OC(=O)C2=CC(C=2C=C3C(=O)OC(C3=CC=2)=O)=C1 WKDNYTOXBCRNPV-UHFFFAOYSA-N 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 3
- JPZRPCNEISCANI-UHFFFAOYSA-N 4-(4-aminophenyl)-3-(trifluoromethyl)aniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C(F)(F)F JPZRPCNEISCANI-UHFFFAOYSA-N 0.000 description 3
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 230000000379 polymerizing effect Effects 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012546 transfer Methods 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- 230000002087 whitening effect Effects 0.000 description 3
- CHLICZRVGGXEOD-UHFFFAOYSA-N 1-Methoxy-4-methylbenzene Chemical compound COC1=CC=C(C)C=C1 CHLICZRVGGXEOD-UHFFFAOYSA-N 0.000 description 2
- HWWYDZCSSYKIAD-UHFFFAOYSA-N 3,5-dimethylpyridine Chemical compound CC1=CN=CC(C)=C1 HWWYDZCSSYKIAD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- PJWQLRKRVISYPL-UHFFFAOYSA-N 4-[4-amino-3-(trifluoromethyl)phenyl]-2-(trifluoromethyl)aniline Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C1=CC=C(N)C(C(F)(F)F)=C1 PJWQLRKRVISYPL-UHFFFAOYSA-N 0.000 description 2
- QHHKLPCQTTWFSS-UHFFFAOYSA-N 5-[2-(1,3-dioxo-2-benzofuran-5-yl)-1,1,1,3,3,3-hexafluoropropan-2-yl]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)(C(F)(F)F)C(F)(F)F)=C1 QHHKLPCQTTWFSS-UHFFFAOYSA-N 0.000 description 2
- 229920002799 BoPET Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- JGGQWILNAAODRS-UHFFFAOYSA-N n-methyl-4-[4-(methylamino)phenyl]aniline Chemical group C1=CC(NC)=CC=C1C1=CC=C(NC)C=C1 JGGQWILNAAODRS-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 238000001291 vacuum drying Methods 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
- 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
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 1
- NSGXIBWMJZWTPY-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropane Chemical compound FC(F)(F)CC(F)(F)F NSGXIBWMJZWTPY-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
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 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
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- FVFYRXJKYAVFSB-UHFFFAOYSA-N 2,3,5,6-tetrafluorobenzene-1,4-diamine Chemical compound NC1=C(F)C(F)=C(N)C(F)=C1F FVFYRXJKYAVFSB-UHFFFAOYSA-N 0.000 description 1
- DJOVAUMVUZNCRR-UHFFFAOYSA-N 2,3,5-trifluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C(F)=C1F DJOVAUMVUZNCRR-UHFFFAOYSA-N 0.000 description 1
- LOSUMUGGQHVNDI-UHFFFAOYSA-N 2,3,5-tris(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F LOSUMUGGQHVNDI-UHFFFAOYSA-N 0.000 description 1
- YMDMDDUYDDFCSX-UHFFFAOYSA-N 2,3-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C(F)(F)F)=C1C(F)(F)F YMDMDDUYDDFCSX-UHFFFAOYSA-N 0.000 description 1
- YXZUDXLWSOZHFN-UHFFFAOYSA-N 2,3-diethylpyridine Chemical compound CCC1=CC=CN=C1CC YXZUDXLWSOZHFN-UHFFFAOYSA-N 0.000 description 1
- WRFSJAVIFPITPG-UHFFFAOYSA-N 2,3-difluorobenzene-1,4-diamine Chemical compound NC1=CC=C(N)C(F)=C1F WRFSJAVIFPITPG-UHFFFAOYSA-N 0.000 description 1
- CEQNIRIQYOUDCF-UHFFFAOYSA-N 2,5-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C=C1C(F)(F)F CEQNIRIQYOUDCF-UHFFFAOYSA-N 0.000 description 1
- ZKTNFNZZMROBEB-UHFFFAOYSA-N 2,5-difluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C=C1F ZKTNFNZZMROBEB-UHFFFAOYSA-N 0.000 description 1
- PVXRBSHBFJXTNM-UHFFFAOYSA-N 2,6-bis(3-aminophenoxy)benzonitrile Chemical compound NC1=CC=CC(OC=2C(=C(OC=3C=C(N)C=CC=3)C=CC=2)C#N)=C1 PVXRBSHBFJXTNM-UHFFFAOYSA-N 0.000 description 1
- OGVUUAGLCNYUGO-UHFFFAOYSA-N 2,6-bis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC(C(F)(F)F)=C(N)C(C(F)(F)F)=C1 OGVUUAGLCNYUGO-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
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- 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
- C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
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- 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
- C08G73/1042—Copolyimides derived from at least two different tetracarboxylic compounds or two different diamino compounds
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- 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
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Description
1)ポリイミドを含むフィルムであって、フィルムの厚さ30μmとした場合において、黄色度が3.0以下、引張弾性率が3.5GPa以上、ガラス転移温度が300℃以上、鉛筆硬度が4H以上であることを特徴とするフィルム。
2)フィルムの厚さ30μmとした場合において、波長400nmの光透過率が60%以上であることを特徴とする、1)に記載のフィルム。
3)ポリイミドの前駆体であるポリアミド酸を構成する酸二無水物が少なくとも1種以上の脂環式酸二無水物を含むことを特徴とする、1)または2)に記載のフィルム。
4)ポリイミドの前駆体であるポリアミド酸を構成するジアミンが少なくとも1種以上のスルホニル基を含むことを特徴とする、1)または2)に記載のフィルム。
5)ポリイミドの前駆体であるポリアミド酸を構成する酸二無水物が少なくとも1種以上の脂環式酸二無水物を含み、且つ、ジアミンが少なくとも1種以上のスルホニル基を含むことを特徴とする1)〜4)のいずれかに記載のフィルム。
6)ポリイミドを構成するジアミンがビス(トリフルオメチル)ベンジジン骨格を含むことを特徴とする、1)〜5)のいずれかに記載のフィルム。
1)ジアミンを有機極性溶媒中に溶解及び/又は分散させた後、これと略等モルの二無水物を反応させて重合する方法。
2)酸二無水物とこれに対し過少モル量のジアミンとを有機極性溶媒中で反応させ、両末端に酸無水物基を有するプレポリマーを得る。続いて、全工程において酸二無水物とジアミンが略等モルとなるようにジアミンを用いて重合する方法。
3)酸二無水物とこれに対し過剰モル量のジアミンとを有機極性溶媒中で反応させ、両末端にアミノ基を有するプレポリマーを得る。続いて、全工程において酸二無水物とジアミン化合物が略等モルとなるように酸二無水物を用いて重合する方法。
4)酸二無水物を有機極性溶媒中に溶解及び/又は分散させた後、これと略等モルとなるようにジアミンを用いて重合する方法。
5)略等モルのテトラカルボン酸とジアミンの混合物を有機極性溶媒中で反応させて重合する方法。
A)得られたポリアミド酸を支持体にキャストして乾燥・イミド化を、行いポリイミドフィルムを得る工程。
B)得られたポリアミド酸溶液に脱水剤及び/またはイミド化触媒を添加し、場合によっては加熱することでイミド化を完了させてポリイミド用液を得る。得られたポリイミド用液を支持体にキャストして乾燥を行いポリイミドフィルムを得る工程。
C)B)で得られたポリイミド溶液に貧溶媒を投入してポリイミド樹脂固形物として析出させて回収し、所望の溶媒に再度溶解させてポリイミド用液を得る。得られたポリイミド用液を支持体にキャストして乾燥を行いポリイミドフィルムを得る工程。
i)有機溶剤中で酸二無水物とジアミンを反応させてポリアミド酸溶液を得る工程、
ii)上記ポリアミド酸溶液を含む製膜ドープを支持体上に流延する工程、
iii)支持体上で加熱した後、支持体からゲルフィルムを引き剥がす工程、
iv)さらに加熱して、残ったアミド酸をイミド化し、かつ乾燥させる工程、
を含むことが好ましい。
i)の工程でのモノマーの純度が高い方が、得られるフィルムは無色透明になる傾向にあり、溶剤の種類によっても変動することがある。ii)〜iv)の工程における熱処理の雰囲気や熱処理の温度もフィルム特性に影響を与え、低酸素濃度雰囲気や低温処理がフィルムは無色透明となる傾向にある。フィルムの着色抑制の観点から、加熱温度はイミド化が完了する範囲で低ければ低いほど好ましい。例えば、350℃以下であるこが好ましく、300℃以下であることが更に好ましく、270℃以下であることが更に好ましく、250℃以下であることが特に好ましい。また、加熱温度が低温であっても、使用するモノマーの種類によってはフィルムが着色する場合があり、着色は雰囲気の制御で抑制が可能となる。加熱時の酸素濃度が5%以下であることが好ましく、1%以下であることが更に好ましく、0.5%以下であることが更に好ましく、0.1%以下であることが特に好ましい。上記工程ii)において無水酢酸等の酸無水物に代表される脱水剤と、イソキノリン、キノリン、β−ピコリン、ピリジン、ジエチルピリジン等の第三級アミン類等に代表されるイミド化触媒とを含む硬化剤を用いてもよい。また、脱水剤とイミド化触媒は、単独で使用することも可能である。これらの方法を単独で、または組み合わせて用いて、黄色度、引張弾性率、ガラス転移温度を所望の範囲に設定する。
i)有機溶剤中で酸二無水物とジアミンを反応させてポリアミド酸溶液を得る工程、
ii)上記ポリアミド酸溶液をイミド化してポリイミド溶液を得る工程、
iii)上記ポリイミド溶液を含む製膜ドープを支持体上に流延する工程、
iv)支持体上で乾燥して引き剥がす工程、又は、支持体上で乾燥した後に支持体からフィルムを引き剥がして追加乾燥する工程
を含むことが好ましい。製膜方法A)に記載と同様の試行錯誤を組み合わせることができる。加えて、iii)とiv)の工程でイミド化を伴わないことから、乾燥温度を低温に抑えることが出来ることが好ましい。フィルム着色を抑える観点から、乾燥温度は200℃以下であることが好ましく、170℃以下であることが好ましく、140℃以下であることが特に好ましい。
i)有機溶剤中で酸二無水物とジアミンを反応させてポリアミド酸溶液を得る工程、
ii)上記ポリアミド酸溶液をイミド化してポリイミド溶液を得る工程、
iii)上記ポリイミド溶液に貧溶媒を投入してポリイミド樹脂固形分を析出させ回収する工程
iv)上記ポリイミド樹脂固形分を溶媒に溶解し、再度ポリイミド溶液を得る工程
v)iv)で得られたポリイミド溶液を含む製膜ドープを支持体上に流延する工程、
vi)支持体上で乾燥して引き剥がす工程、又は、支持体上で乾燥した後に支持体からフィルムを引き剥がして追加乾燥する工程
を含むことが好ましい。製膜方法A)及び製膜方法b)に記載と同様の試行錯誤を組み合わせることができる。加えて、iii)の工程で、前駆体合成時に発生した不純物、脱水剤、イミド化触媒を貧溶媒で洗浄・除去することが可能となる点で好ましい。また、iv)の工程での溶媒の選択が可能となり、製膜工程に適した溶媒や低温での乾燥がかのうとなり、v)やvi)の生産性が大きく向上する点で好ましい。
測定には島津製作所製のAUTOGRAPH AGS−Jを用いて、ASTM D882に準じて行った。(サンプル測定範囲;幅15mm、つかみ具間距離100mm、引張速度;200mm/min、測定温度;23℃)。サンプルは23℃/55%RHで1週間静置して調湿したものを測定した。
日本電色工業株式会社製HANDY COLORIMETER NR−3000を用い測定した。測定は18cm角サイズのサンプルについて位置を変えて五箇所測定し、平均値をフィルムの測定値とした。
JIS K−5400−1990の8.4.1鉛筆引っかき試験により、フィルムの鉛筆硬度を測定した。
日本分光社製紫外可視近赤外分光光度計(V−650)を用いて、フィルムの200−800nmにおける光透過率を測定し、400nmの波長における光透過率を指標として用いた。
日本電色工業製積分球式ヘイズメーター300Aにより、JIS K7105−1981記載の方法により測定した。
セイコー電子工業社製DMS−200を用い、測定長(測定治具間隔)を20mmとして、動的粘弾性測定を行い、貯蔵弾性率の変曲点をガラス転移温度とした。
2LのセパラブルフラスコにN,N−ジメチルホルムアミド(DMF)を320.0g投入し、窒素雰囲気下で攪拌した。そこに、2,2’-ビス(トリフルオロメチル)ベンジジン(TFMB)を47.8g添加し、続けて1,2,3,4−シクロブタンテトラカルボン酸二無水物(CBDA)を23.4g添加し、続けて3,3',4,4'−ビフェニルテトラカルボン酸二無水物(BPDA)を8.7g添加し、窒素雰囲気下で10時間攪拌して溶解させた。固形分濃度20%、23℃での粘度が900ポイズのポリイミド前駆体1を得た。
2LのセパラブルフラスコにDMFを320.0g投入し、窒素雰囲気かで攪拌した。そこに、TFMBを40.0g添加し、続けてCBDAを12.2g添加下、続けて2,2−ビス(3,4−ジカルボキシフェニル)−1,1,1,3,3,3−ヘキサフルオロプロパン二無水物(6FDA)を27.7g添加し、窒素雰囲気下で10時間攪拌して溶解させた。固形分濃度20%、23℃での粘度が1000ポイズのポリイミド前駆体を得た。上記ポリイミド前駆体にイミド化触媒としてピリジン29.6gを添加し、完全に分散させた。分散された溶液中に無水酢酸38.3gを添加し、120℃で2時間攪拌したのち、室温まで冷却した。冷却した溶液攪拌しながら、1Lの2−プロピルアルコール(IPA)を2〜3滴/秒となる速度で投入し、ポリイミドを析出させた。その後、桐山ロートを使用して吸引ろ過を行い、500gのIPAで洗浄を行った。洗浄作業を4回繰り返した後、120℃に設定した真空オーブンで12時間乾燥させることでポリイミド2を得た。
2LのセパラブルフラスコにDMFを320.0g投入し、窒素雰囲気下で攪拌した。そこに、2,2’−ジメチルベンジジン、2,2’−BZ)を38.9g添加し、続けて1,2,4,5−シクロヘキサンテトラカルボン酸二無水物(PMDA−HS)を41.0g添加し、窒素雰囲気下で10時間攪拌して溶解させた。固形分濃度20%、23℃での粘度が800ポイズのポリイミド前駆体を得た。上記ポリイミド前駆体にイミド化触媒としてピリジン43.5gを添加し、完全に分散させた。分散された溶液中に無水酢酸56.1gを添加し、120℃で2時間攪拌したのち、室温まで冷却した。冷却した溶液攪拌しながら、1Lの2−プロピルアルコール(IPA)を2〜3滴/秒となる速度で投入し、ポリイミドを析出させた。その後、桐山ロートを使用して吸引ろ過を行い、500gのIPAで洗浄を行った。洗浄作業を4回繰り返した後、120℃に設定した真空オーブンで12時間乾燥させることでポリイミド3を得た。
2LのセパラブルフラスコにDMFを320.0g投入し、窒素雰囲気かで攪拌した。そこに、TFMBを31.5g添加し、続けて3,3’−ジアミノジフェニルスルホン(3,3’−DDS)を10.5g添加し、続けてCBDAを19.3g添加下し、続けて6FDAを18.7g添加し、窒素雰囲気下で10時間攪拌して溶解させた。固形分濃度20%、23℃での粘度が1100ポイズのポリイミド前駆体を得た。上記ポリイミド前駆体にイミド化触媒としてピリジン35.6gを添加し、完全に分散させた。分散された溶液中に無水酢酸45.9gを添加し、120℃で2時間攪拌したのち、室温まで冷却した。冷却した溶液攪拌しながら、1Lの2−プロピルアルコール(IPA)を2〜3滴/秒となる速度で投入し、ポリイミドを析出させた。その後、桐山ロートを使用して吸引ろ過を行い、500gのIPAで洗浄を行った。洗浄作業を4回繰り返した後、120℃に設定した真空オーブンで12時間乾燥させることでポリイミド4を得た。
2LのセパラブルフラスコにDMFを328.0g投入し、窒素雰囲気下で攪拌した。そこに、TFMBを37.5g添加し、続けてBPDAを34.4g添加し、窒素雰囲気下で19時間攪拌して溶解させた。固形分濃度18%、23℃での粘度が1900ポイズのポリイミド前駆体5を得た。
2LのセパラブルフラスコにDMFを320.0g投入し、窒素雰囲気下で攪拌した。そこに、TFMBを33.5g添加し、続けて6FDAを46.4g添加し、窒素雰囲気下で10時間攪拌して溶解させた。固形分濃度20%、23℃での粘度が1000ポイズのポリイミド前駆体を得た。上記ポリイミド前駆体にイミド化触媒としてピリジン24.8gを添加し、完全に分散させた。分散された溶液中に無水酢酸32.1gを添加し、120℃で2時間攪拌したのち、室温まで冷却した。冷却した溶液攪拌しながら、1Lの2−プロピルアルコール(IPA)を2〜3滴/秒となる速度で投入し、ポリイミドを析出させた。その後、桐山ロートを使用して吸引ろ過を行い、500gのIPAで洗浄を行った。洗浄作業を4回繰り返した後、120℃に設定した真空オーブンで12時間乾燥させることでポリイミド6を得た。
2LのセパラブルフラスコにDMFを328.0g投入し、窒素雰囲気下で攪拌した。そこに、TFMBを33.4g添加し、続けてBPDAを15.4g添加し、続けて6FDAを23.1g添加し、窒素雰囲気下で15時間攪拌して溶解させた。固形分濃度18%、23℃での粘度が1700ポイズのポリイミド前駆体7を得た。
合成例1で得られたポリイミド前駆体1の固形分に対して5%の3,5−ルチジンを添加し、固形分濃度が15%となるようにDMFを加えて攪拌し、均一な溶液を得た。コンマコーターを用いて、前記ポリイミド溶液を無アルカリガラス板状に塗布し、40℃で10分、80℃で30分、150℃で30分、大気雰囲気下で乾燥した。続いて、イナートオーブンを用いて窒素雰囲気下で260で1時間乾燥し厚さ30μmのポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例2で得られたポリイミド2を、DMFに溶解し、固形分濃度13%のポリイミド溶液を得た。コンマコーターを用いて、前記ポリイミド溶液を無アルカリガラス板状に塗布し、40℃で10分、80℃で30分、150℃で30分、200℃で1時間、大気雰囲気下で乾燥し、厚さ30μmのポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例3で得られたポリイミド3を使用することを除き、実施例2と同様にポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例4で得られたポリイミド3を使用することを除き、実施例2と同様にポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例5で得られたポリイミド前駆体5を100g秤量し、別途調合したイミド化促進液(無水酢酸28.4gとβ−ピコリン6.8gとDMF4.8g)を加えた後、直ちにガラス棒を用いて攪拌した溶液をコンマコーターを用いてPETフィルムに塗布し、40℃で5分、80℃で10分、150℃で10分、大気雰囲気下で乾燥した。得られたフィルムをPETフィルムから剥がして金属製のピン枠に固定し、200℃で30秒、250℃で30秒、300℃で30秒、350℃で2分、大気雰囲気下で焼成し、厚さ30μmのポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例6で得られたポリイミド5を使用することを除き、実施例2と同様にポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
合成例7で得られたポリイミド前駆体7を100g秤量し、別途調合したイミド化促進液(無水酢酸25.3gとβ−ピコリン6.1gとDMF8.6g)を加えた後、直ちにガラス棒を用いて攪拌した溶液を使用することを除き、比較例1と同様にポリイミドフィルムを得た。得られたポリイミドフィルムの評価結果を表1に示す。
ポリイミドの前駆体であるポリアミド酸を構成する酸二無水物が少なくとも1種以上の脂環式酸二無水物を含む系は、表1にみられるように低い黄色度、高い弾性率、高いガラス転移温度、高い鉛筆硬度を併せ持ち、ガラス代替材料に好適に使用することができるポリイミドフィルムが得られた。
Claims (2)
- ポリイミドを含むフィルムであって、フィルムの厚さ30μmとした場合において、黄色度が3.0以下、引張弾性率が3.5GPa以上、ガラス転移温度が300℃以上、鉛筆硬度が4H以上であり、
上記ポリイミドの前駆体であるポリアミド酸を構成する酸二無水物が、少なくとも1種以上の脂環式酸二無水物を含み、
上記脂環式酸二無水物は、1,2,3,4−シクロブタンテトラカルボン酸二無水物、1,2,3,4−シクロペンタンテトラカルボン酸二無水物、および、1,2,4,5−シクロヘキサンテトラカルボン酸二無水物から選択される1種類以上であり、
上記ポリイミドの前駆体であるポリアミド酸を構成するジアミンには、下記(i)および(ii)の両方が含まれることを特徴とするガラス代替材料用のフィルム:
(i)1種以上のスルホニル基を含むジアミン;
(ii)ビス(トリフルオメチル)ベンジジン骨格を含むジアミン;
(ただし、下記(a)および(b)の場合を除く:
(a)上記ポリアミド酸が、全モノマー成分を100モル%として、下記化合物7を5モル%、下記化合物11を5モル%、2,2−(ビストリフルオロメチル)ベンジジンを40モル%、4,4’−(ヘキサフルオロイソプロピリデン)ジフタル酸無水物を20モル%およびシクロブタン1,2,3,4−テトラカルボン酸二無水物を30モル%含む場合;
(b)上記ポリアミド酸が、全モノマー成分を100モル%として、下記化合物7を10モル%、下記化合物11を10モル%、2,2−(ビストリフルオロメチル)ベンジジンを30モル%、3,3’,4,4’−ビフェニルテトラカルボン酸二無水物を20モル%およびシクロブタン1,2,3,4−テトラカルボン酸二無水物を30モル%含む場合)。
- フィルムの厚さ30μmとした場合において、波長400nmの光透過率が60%以上であることを特徴とする、請求項1に記載のフィルム。
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