JP6905227B2 - ジアミンおよびポリイミド、並びにそれらの利用 - Google Patents
ジアミンおよびポリイミド、並びにそれらの利用 Download PDFInfo
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- JP6905227B2 JP6905227B2 JP2017099643A JP2017099643A JP6905227B2 JP 6905227 B2 JP6905227 B2 JP 6905227B2 JP 2017099643 A JP2017099643 A JP 2017099643A JP 2017099643 A JP2017099643 A JP 2017099643A JP 6905227 B2 JP6905227 B2 JP 6905227B2
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- Prior art keywords
- polyimide
- bis
- film
- group
- solvent
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- 229920001721 polyimide Polymers 0.000 title claims description 141
- 239000004642 Polyimide Substances 0.000 title claims description 125
- 150000004985 diamines Chemical class 0.000 title claims description 42
- 125000003118 aryl group Chemical group 0.000 claims description 23
- 239000000758 substrate Substances 0.000 claims description 23
- 239000002966 varnish Substances 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 125000001931 aliphatic group Chemical group 0.000 claims description 19
- 238000001035 drying Methods 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000004033 plastic Substances 0.000 claims description 4
- 229920003023 plastic Polymers 0.000 claims description 4
- 239000000243 solution Substances 0.000 description 54
- 239000010408 film Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 47
- 238000000034 method Methods 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- -1 dinitro compound Chemical class 0.000 description 25
- 239000002243 precursor Substances 0.000 description 25
- 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 description 22
- 238000006243 chemical reaction Methods 0.000 description 19
- 239000000126 substance Substances 0.000 description 19
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical class C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 13
- 229920005575 poly(amic acid) Polymers 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 238000010438 heat treatment Methods 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- 238000000576 coating method Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 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 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WVOLTBSCXRRQFR-DLBZAZTESA-M cannabidiolate Chemical group 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 9
- 239000011248 coating agent Substances 0.000 description 9
- 239000011521 glass Substances 0.000 description 9
- 239000000463 material Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 150000001408 amides Chemical class 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 230000000704 physical effect Effects 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- 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 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 238000011282 treatment Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000010409 thin film Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000010419 fine particle Substances 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- XDTTUTIFWDAMIX-UHFFFAOYSA-N 3-methyl-4-nitrobenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1[N+]([O-])=O XDTTUTIFWDAMIX-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
- 150000005443 4-nitrobenzoic acid derivatives Chemical class 0.000 description 3
- YGYCECQIOXZODZ-UHFFFAOYSA-N 4415-87-6 Chemical compound O=C1OC(=O)C2C1C1C(=O)OC(=O)C12 YGYCECQIOXZODZ-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 3
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002776 aggregation Effects 0.000 description 3
- 238000004220 aggregation Methods 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 230000006866 deterioration Effects 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 150000002605 large molecules Chemical class 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
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 239000013557 residual solvent Substances 0.000 description 3
- 150000003384 small molecules Chemical class 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- 0 CC(C(Cc(ccc(C(*(c(cc1)cc(*)c1-c1ccc(*)cc1*)=*)=O)c1)c1N=C)C(C)=O)=O Chemical compound CC(C(Cc(ccc(C(*(c(cc1)cc(*)c1-c1ccc(*)cc1*)=*)=O)c1)c1N=C)C(C)=O)=O 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 235000002597 Solanum melongena Nutrition 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- ZIXLDMFVRPABBX-UHFFFAOYSA-N alpha-methylcyclopentanone Natural products CC1CCCC1=O ZIXLDMFVRPABBX-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- 238000007033 dehydrochlorination reaction Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 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
- 239000003759 ester based solvent Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- JBFHTYHTHYHCDJ-UHFFFAOYSA-N gamma-caprolactone Chemical compound CCC1CCC(=O)O1 JBFHTYHTHYHCDJ-UHFFFAOYSA-N 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
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- 235000009566 rice Nutrition 0.000 description 2
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- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 2
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- 230000004580 weight loss Effects 0.000 description 2
- HFBHOAHFRNLZGN-LURJTMIESA-N (2s)-2-formamido-4-methylpentanoic acid Chemical compound CC(C)C[C@@H](C(O)=O)NC=O HFBHOAHFRNLZGN-LURJTMIESA-N 0.000 description 1
- 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
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-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
- PWGJDPKCLMLPJW-UHFFFAOYSA-N 1,8-diaminooctane Chemical compound NCCCCCCCCN PWGJDPKCLMLPJW-UHFFFAOYSA-N 0.000 description 1
- KZVBBTZJMSWGTK-UHFFFAOYSA-N 1-[2-(2-butoxyethoxy)ethoxy]butane Chemical compound CCCCOCCOCCOCCCC KZVBBTZJMSWGTK-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- BHPCMPVIMAJIQS-UHFFFAOYSA-N 2,3,5,6-tetrakis(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=C(C(F)(F)F)C(C(F)(F)F)=C(N)C(C(F)(F)F)=C1C(F)(F)F BHPCMPVIMAJIQS-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
- 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
- XFWCWQUDUPQGKG-UHFFFAOYSA-N 2,6-difluorobenzene-1,4-diamine Chemical compound NC1=CC(F)=C(N)C(F)=C1 XFWCWQUDUPQGKG-UHFFFAOYSA-N 0.000 description 1
- GXVUZYLYWKWJIM-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanamine Chemical compound NCCOCCN GXVUZYLYWKWJIM-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
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- Paints Or Removers (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
本発明の一実施形態に係るジアミンは、下記式(1):
本発明の一実施形態に係るポリイミドは、下記式(3):
本発明の一実施形態に係るワニスは、本発明の一実施形態に係るポリイミドを固形分濃度5重量%以上含む。固形分濃度が5重量%以上であれば、ワニスの塗工によって得られるフィルムの平滑性を確保することができる。上記固形分濃度は、5〜40重量%が好ましく、10〜25重量%であることがさらに好ましい。
本発明の一実施形態に係るフィルム(ポリイミドフィルム)は、本発明の一実施形態に係るワニス(ポリイミドワニス)を乾燥して得られる。上記フィルムは、基板上にワニスを塗工し、乾燥することで製造することができる。また、ポリイミド前駆体であるポリアミド酸を基板に塗工し、得られた膜を加熱してイミド化および乾燥することでもフィルムを得ることができる。得られるフィルムの熱膨張特性および寸法安定性の観点から、上述のポリイミドワニスを塗工し、乾燥する方法がより好ましい。
本発明の一実施形態に係るポリイミドは、耐熱性および絶縁性等のポリイミド本来の特性に加えて、線熱膨張係数が低く、しかも溶液加工性および透明性に優れるという極めて有用な特性を示す。
(式(1)中、置換基Rは独立して、炭素数1〜4のアルキル基またはアルコキシ基を表し、nは置換基Rの数を表し、1〜4の整数である)。
(式(3)中、置換基Rは独立して、炭素数1〜4のアルキル基またはアルコキシ基を表し、nは置換基Rの数を表し、1〜4の整数であり、X1は4価の脂肪族基および芳香族基の少なくともいずれか一方を表す)。
(式(4)中、X1は4価の脂肪族基および芳香族基の少なくともいずれか一方を表す)。
以下、本発明を実施例により具体的に説明するが、これら実施例に限定されるものではない。なお、以下の例における物性値は、次の方法により測定した。
ジアミンの赤外線吸収スペクトルは、フーリエ変換赤外分光光度計(日本分光社製、FT−IR4100)を用い、KBr法で測定した。またポリイミド前駆体およびポリイミドの赤外線吸収スペクトルは、別途約4〜5μm厚の薄膜を作製し、透過法で測定した。
ジアミンおよびポリイミド粉末の1H−NMRスペクトルは、重水素化ジメチルスルホキシド(DMSO−d6)を溶媒として、NMR分光光度計(日本電子社製、ECP400)を用いて測定した。
ジアミンの融点および融解曲線は、示差走査熱量分析装置(ネッチ・ジャパン社製、DSC3100)を用い、窒素雰囲気中、昇温速度5℃/分で測定した。
ポリイミド前駆体(PAA)およびポリイミド(PI)の還元粘度は、固形分濃度0.5重量%、30℃においてオストワルド粘度計を用いて測定した。この値は固有粘度と見なすことができ、この値が高い程分子量が高いことを表す。
ポリイミドフィルム(約20μm厚)のガラス転移温度(Tg)は、熱機械分析装置(ネッチ・ジャパン社製、TMA4000)を用い、周波数0.1Hz、昇温速度5℃/分における損失エネルギー曲線のピーク温度から求めた。Tgが高いほど、物理的耐熱性が高いことを表す。
ポリイミドフィルム(約20μm厚)のCTEは、熱機械分析装置(ネッチ・ジャパン社製、TMA4000)を用い、荷重0.5g/膜厚1μm当たり、昇温速度5℃/分における試験片の伸びより、100〜200℃の範囲での平均値として求めた。CTE値が0に近いほど熱寸法安定性に優れていることを表す。
ポリイミドフィルム(約20μm厚)の5%重量減少温度(Td 5)は、ネッチ・ジャパン社製熱重量分析装置(TG−DTA2000)を用いて、窒素中(N2)および空気中(air)、昇温速度10℃/分での昇温過程において、ポリイミドフィルム(20μm厚)の重量が、初期重量の5%減少した時の温度から求めた。Td 5値が高いほど化学的耐熱性(熱安定性)が高いことを表す。
ポリイミドフィルム(約20μm厚)の機械的特性はエー・アンド・ディー社製引張試験機(テンシロンUTM−II)を用いて評価した。試験片(30mm長×3mm幅×約20μm厚)を作製し、引張試験(延伸速度:8mm/分)を実施して、応力−歪曲線の初期勾配から引張弾性率(E)、破断点応力から破断強度(σb)、破断時の伸び率から破断伸び(εb)を求めた。破断伸びが高いほどフィルムの靭性が高いことを表す。なお、破断伸びは、平均値(ave)と最大値(max)とを示した。
ポリイミドフィルムの透明性は以下の光学特性から評価した。日本分光社製紫外−可視分光光度計(V−530)を用いて波長200〜800nmの範囲でポリイミドフィルム(約20μm厚)の光透過率曲線を測定し、波長400nmにおける光透過率(T400)、および、光透過率が事実上ゼロとなる波長(カット・オフ波長(λcut))を求めた。またこのスペクトルを基に、色彩計算プログラム(日本分光)を用い、ASTM E313規格に基づいて黄色度指数(YI値)を求めた。更に、ヘイズメーター(日本電色工業社製、NDH4000)を用い、JIS K7361−1およびJIS K7136規格に基づき、全光線透過率(Ttot)および濁度(ヘイズ)を求めた。
偏光板付接眼鏡付Abbe屈折計4T(ATAGO社製)を用い、光源としてNaD線(589.3nm)、中間液としてヨウ化メチレン溶液に硫黄を飽和させた溶液(nD=1.72〜1.80)、および、テストピース(nD=1.72)を用いて、ポリイミドフィルムの面内屈折率ninと面外屈折率noutとを測定し、厚み方向複屈折Δnth(=nin−nout)を求めた。
溶液加工性を、溶媒への溶解性に基づいて評価した。ポリイミドの粉末を99倍重量の溶媒に加え、試験管ミキサーを用いて5分間撹拌して溶解状態を目視で確認した。ここで、ポリイミドの粉末が溶媒に均一に溶解した場合、「優れた溶解性を示す」と評価した。
3−メチル−4−ニトロ安息香酸=3M4NB
3M4NB塩素化体=3M4NBC
N,N−ジメチルホルムアミド=DMF
テトラヒドロフラン=THF
2,2’−ビス(トリフルオロメチル)ベンジジン=TFMB
N,N−ジメチルアセトアミド=DMAc
1,2,3,4−シクロブタンテトラカルボン酸二無水物=CBDA
N−メチル−2−ピロリドン=NMP
ジメチルスルホキシド=DMSO
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=6FDA
γ−ブチロラクトン=GBL。
<ジアミンの合成>
上記式(2)で表される本発明の一実施形態に係るジアミン(以下、M−ABMBと称する)は、M−ABMBの前駆体であるジニトロ化合物(以下、M−NBMBと称する)を合成し、ニトロ基を還元することで合成した。具体的には以下のような手順で行った。
<ポリイミド前駆体の重合、化学イミド化、製膜および膜物性>
反応容器中、実施例1に記載のジアミン(M−ABMB)1.1731g(2mmol)を脱水済みのDMAcに溶解した。得られた溶液にCBDA粉末0.3922g(2mmol)を少しずつ加え、密閉した。反応初期の固形分濃度は30重量%であった。室温で攪拌を続けたところ、重合反応が進み、溶液粘度が増加して十分に攪拌しにくくなった。そのため、反応容器へ徐々にDMAcを添加していき、72時間攪拌後は固形分濃度が18重量%になるまで溶液を希釈した。72時間攪拌後、粘性のある均一なポリイミド前駆体溶液を得た。得られたポリイミド前駆体の固有粘度は1.75dL/gであった。
テトラカルボン酸二無水物として、CBDAを95mol%、6FDAを5mol%用いた以外は実施例2に記載した方法と同様にしてポリイミド前駆体を重合し、化学イミド化およびキャスト製膜を行ってポリイミドフィルムを得た。図1に別途作製したポリイミド薄膜の赤外線吸収スペクトルを示す。当該赤外線吸収スペクトルは、フーリエ変換赤外分光光度計FT/IR−4100 type A(日本分光株式会社製)を用いて測定した。また表1に物性値を示す。このフィルム(膜厚約20μm)は、実施例2のフィルムより高いT400値、より低いYI値およびより低いヘイズ値を示すことから、透明性が改善されていることがわかる。これは6FDAを5mol%共重合することで、溶媒溶解性が改善され、製膜時の溶媒蒸発過程において主鎖の凝集が妨げられた結果であると考えられる。また、低いCTE値(16.9ppm/K)に加えて高い耐熱性(Tg=348℃)を示した。化学イミド化したポリイミド粉末はDMAc、DMAc/GBLの混合溶媒(体積比1/1)およびDMAc/CPNの混合溶媒(体積比1/1)に対して優れた溶解性を示し、固形分濃度約10重量%のワニスを得ることが可能であった。
テトラカルボン酸二無水物として、CBDAを70mol%、6FDAを30mol%用いた以外は実施例2に記載した方法と同様にしてポリイミド前駆体を重合し、化学イミド化およびキャスト製膜を行ってポリイミドフィルムを得た。表1に物性値を示す。このフィルムは高いT400値、低いYI値および低いヘイズ値で示されるように、優れた透明性を有していた。また、低いCTE値(17.9ppm/K)に加えて高い耐熱性(Tg=334℃)を示した。化学イミド化したポリイミド粉末はNMP、DMAcおよびDMFに室温で優れた溶解性を示した。
テトラカルボン酸二無水物として、CBDAを50mol%、6FDAを50mol%用いた以外は実施例2に記載した方法と同様にしてポリイミド前駆体を重合し、化学イミド化およびキャスト製膜を行ってポリイミドフィルムを得た。表1に物性値を示す。このフィルムは高いT400値、低いYI値、低いヘイズ値より、優れた透明性を有していた。また、比較的低いCTE値(23.6ppm/K)に加えて高い耐熱性(Tg=349℃)を示した。化学イミド化したポリイミド粉末はNMP、DMAc、DMFおよびDMSOに室温で優れた溶解性を示した。
テトラカルボン酸二無水物として、CBDAの代わりに6FDAを用いた以外は実施例2に記載した方法と同様にしてポリイミド前駆体を重合し、化学イミド化およびキャスト製膜を行ってポリイミドフィルムを得た。表1に物性値を示す。このフィルムは高いT400値、低いYI値、低いヘイズ値より、優れた透明性を有していた。また、化学イミド化したポリイミド粉末はNMP、DMAc、DMF、DMSO、GBL、トリグライム、シクロペンタノン、アセトンおよびTHFに室温で優れた溶解性を示した。GBLを溶媒として固形分濃度15重量%の濃度で安定なワニスが得られた。THFを溶出溶媒としてゲル浸透クロマトグラフィーにより分子量を測定したところ、数平均分子量(Mn)=2.3×104、重量平均分子量(Mw)=5.7×104であった。
本発明の一実施形態に係るジアミンにおけるメチル置換基の効果を調査するために、メチル置換基のないジアミン(ABMB)を用い、実施例2に記載した方法によりCBDAと重付加反応させてポリイミド前駆体を得た。なお、ABMBは下記式(9)で表される。
ジアミンとしてM−ABMBの代わりにTFMBを用いた以外は、実施例2に記載した方法と同様にしてポリイミド前駆体を重合した。その溶液に実施例2に記載した方法と同様にして化学イミド化剤を滴下したところ、反応溶液がゲル化したため、化学イミド化を実施することは困難であった。これはCBDAとTFMBとから得られるポリイミドの溶媒溶解性が不十分であるためである。
Claims (9)
- 請求項3〜6のいずれか1項に記載のポリイミドを固形分濃度5重量%以上にて含むワニス。
- 請求項7に記載のワニスを乾燥して得られるフィルム。
- 請求項8に記載のフィルムを含む画像表示装置用プラスチック基板。
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