JPWO2013121917A1 - ジアミン、ポリイミド、ならびに、ポリイミドフィルムおよびその利用 - Google Patents
ジアミン、ポリイミド、ならびに、ポリイミドフィルムおよびその利用 Download PDFInfo
- Publication number
- JPWO2013121917A1 JPWO2013121917A1 JP2014500173A JP2014500173A JPWO2013121917A1 JP WO2013121917 A1 JPWO2013121917 A1 JP WO2013121917A1 JP 2014500173 A JP2014500173 A JP 2014500173A JP 2014500173 A JP2014500173 A JP 2014500173A JP WO2013121917 A1 JPWO2013121917 A1 JP WO2013121917A1
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- Prior art keywords
- polyimide
- bis
- solution
- film
- diamine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920001721 polyimide Polymers 0.000 title claims abstract description 159
- 239000004642 Polyimide Substances 0.000 title claims abstract description 126
- 150000004985 diamines Chemical class 0.000 title claims abstract description 52
- 239000000758 substrate Substances 0.000 claims description 30
- 125000001931 aliphatic group Chemical group 0.000 claims description 14
- 239000000463 material Substances 0.000 claims description 14
- 230000003287 optical effect Effects 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 4
- 125000003368 amide group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 89
- 239000010408 film Substances 0.000 description 56
- 239000002904 solvent Substances 0.000 description 39
- 238000000034 method Methods 0.000 description 35
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 24
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 17
- -1 3-aminophenoxy Chemical group 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 16
- 239000011521 glass Substances 0.000 description 16
- 229920005575 poly(amic acid) Polymers 0.000 description 16
- 239000002243 precursor Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- 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 15
- 238000005259 measurement Methods 0.000 description 14
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 13
- 239000000843 powder Substances 0.000 description 13
- 238000002834 transmittance Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 12
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000000576 coating method Methods 0.000 description 11
- 239000012046 mixed solvent Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 10
- 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 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 7
- SXGMVGOVILIERA-UHFFFAOYSA-N (2R,3S)-2,3-diaminobutanoic acid Natural products CC(N)C(N)C(O)=O SXGMVGOVILIERA-UHFFFAOYSA-N 0.000 description 5
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 230000009477 glass transition Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 230000007547 defect Effects 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
- 239000010419 fine particle Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000012299 nitrogen atmosphere Substances 0.000 description 4
- 150000007524 organic acids Chemical class 0.000 description 4
- 239000009719 polyimide resin Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 230000018044 dehydration Effects 0.000 description 3
- 238000006297 dehydration reaction Methods 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 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
- 238000001308 synthesis method Methods 0.000 description 3
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 2
- YUHNZKXDJLNIRA-UHFFFAOYSA-N 1,2-dimethoxyethane;1,2-dimethoxypropane Chemical compound COCCOC.COCC(C)OC YUHNZKXDJLNIRA-UHFFFAOYSA-N 0.000 description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- SKDHHIUENRGTHK-UHFFFAOYSA-N 4-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=C(C(Cl)=O)C=C1 SKDHHIUENRGTHK-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 2
- 239000012024 dehydrating agents Substances 0.000 description 2
- 230000006866 deterioration 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
- 239000003759 ester based solvent Substances 0.000 description 2
- 239000004210 ether based solvent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000005453 ketone based solvent Substances 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- 239000002966 varnish Substances 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
- LJMPOXUWPWEILS-GUCUJZIJSA-N (3ar,4as,7ar,8as)-3a,4,4a,7a,8,8a-hexahydrofuro[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1[C@@H]2C(=O)OC(=O)[C@@H]2C[C@@H]2C(=O)OC(=O)[C@@H]21 LJMPOXUWPWEILS-GUCUJZIJSA-N 0.000 description 1
- YDFIYIYVPIMGSJ-UHFFFAOYSA-N 1,2-diethoxyethane;1,2-dimethoxybutane Chemical compound CCOCCOCC.CCC(OC)COC YDFIYIYVPIMGSJ-UHFFFAOYSA-N 0.000 description 1
- MQQRFOXFIPBFOV-UHFFFAOYSA-N 1,2-dimethylcyclobutane-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1(C)C(C(O)=O)C(C(O)=O)C1(C)C(O)=O MQQRFOXFIPBFOV-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
- 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
- JRRDISHSXWGFRF-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOC JRRDISHSXWGFRF-UHFFFAOYSA-N 0.000 description 1
- ZLDFIWDSBWFSMK-UHFFFAOYSA-N 1-[2-(2-ethoxyethoxy)ethoxy]-2-methoxyethane;1-methoxy-2-[2-(2-methoxyethoxy)ethoxy]ethane Chemical compound COCCOCCOCCOC.CCOCCOCCOCCOC ZLDFIWDSBWFSMK-UHFFFAOYSA-N 0.000 description 1
- YZWVMKLQNYGKLJ-UHFFFAOYSA-N 1-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-2-methoxyethane Chemical compound CCOCCOCCOCCOCCOC YZWVMKLQNYGKLJ-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
- 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
- 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
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
- C08G73/14—Polyamide-imides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
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Abstract
Description
2.下記式(3)で表される繰り返し単位を有することを特徴とするポリイミド。
上記式(1)で表されるジアミンとしては、特に下記式(2)で表されるジアミンが好ましい。下記式(2)で表されるジアミンは、分子内にアミド結合を有する。そのため、下記式(2)で表されるジアミンを用いて得られるポリイミドでは、分子が直線状になると共に、分子間水素結合が形成されると考えられる。
本発明のポリイミドを製造する場合、上記式(2)および(9)で表されるジアミンのいずれか一方のみを用いてもよいし、両方を用いてもよい。上記式(2)および(9)で表されるジアミンを両方用いる場合、モル比は適宜決定されればよい。
上記ポリイミドとしては、下記式(4)で表される繰り返し単位を有するポリイミドが好ましい。
透明性を向上させる観点から、下記式(5)で表される繰り返し単位を有するポリイミドが好ましい。
また、下記式(6)で表される繰り返し単位を有するポリイミドがより好ましい。
本発明のポリイミドの総繰り返し単位を100モル%とした場合に、上記式(7)で表される繰り返し単位の含有量は、1モル%以上50モル%以下であることが好ましく、10モル%以上50モル%以下であることがより好ましく、20モル%以上50モル%以下であることがさらに好ましい。
5.下記式(5)で表される繰り返し単位を有することを特徴とする上記2または4に記載のポリイミド。
6.下記式(6)で表される繰り返し単位を有することを特徴とする上記2または4に記載のポリイミド。
8.上記2、4〜7のいずれか1つに記載のポリイミドから得られたポリイミドフィルム。
2,2’−ビス(トリフルオロメチル)ベンジジン=TFMB
(1S,2S,4R,5R)−シクロヘキサンテトラカルボン酸二無水物=H’‐PMDA
N,N−ジメチルアセトアミド=DMAc
4,4’‐ジアミノベンズアニリド=DABA。
(ジアミンの合成)
上記式(8)で表されるジアミン(以下、「ABMB」という)を上記式(13)に示す方法により合成した。具体的な合成方法を以下に示す。
3.2023g(10mmol)の2,2’−ビス(トリフルオロメチル)ベンジジン(TFMB)、1.75mLのTHF、および3.3mL(40mmol)のピリジン溶液を、3.8023g(20.5mmol)の4−ニトロベンゼンカルボン酸クロライド(4−NBC)を6.26mLのテトラヒドロフラン(以下、「THF」という)に溶かした溶液に氷浴下にてシリンジを用いて添加した。その結果、多量の黄白色沈殿が生じた。12時間静置後、得られた黄白色沈殿をろ過し、THF、イオン交換水で十分洗浄した。得られた粉末を100℃で12時間減圧乾燥し、ABMB前駆体であるニトロ化物(以下、「NBMB」という。収量:5.9216g、収率:95.7%)を得た。得られた生成物はプロトンNMR、FT−IRにより同定した。
9.2410g(14.94mmol)のNBMB、0.9279gのPd/Cを120mLのエタノールに溶解および分散した。得られた溶液に80℃にて水素ガスをバブリングし7時間反応を行なった。反応終点は薄層クロマトグラフィーにより確認した。反応終了後、反応混合物を熱ろ過し、ろ液を水中に滴下したところ白色沈殿を生じた。12時間攪拌後、得られた粉末を分取し、水で十分洗浄した。その後100℃で12時間減圧乾燥を行い、ABMB粗生成物7.9811g(収率:95.6%)を得た。
1.6754g(3mmol)のABMBを5.4784gのNMPに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え、室温で7時間攪拌した。得られた溶液をNMPによって固形分濃度10.2重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下でゆっくりと滴下し、その後24時間攪拌した。得られた溶液を大量のメタノールに加え、目的生成物を沈殿させた。得られた白色沈殿をメタノールで十分洗浄し、真空乾燥した。
フィルム作製条件を次の通り変更したほかは、実施例2と同様に行なった。得られたポリイミド粉末をシクロペンタノンに溶解し、3重量%の溶液を調製した。当該溶液をガラス基板上に流延し、60℃で2時間熱風乾器を用いて乾燥した。その後ガラス基板上で真空中250℃の条件で1時間乾燥を行い、その後基板から剥離しさらに真空中250℃で1時間熱処理し、フィルムを作製した。なお、フィルムは、平均線熱膨張係数、機械特性の測定用として膜厚10μmのものと、屈折率の測定用として膜厚15μmのものと2種類を作製した。
1.3403g(2.4mmol)のABMBと0.1921g(0.6mmol)のTFMBを5.1448gのNMPに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え、室温で7時間攪拌した。得られた溶液をNMPによって固形分濃度10.0重量%に希釈後、3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下でゆっくりと滴下し、その後24時間攪拌した。得られた溶液を大量のメタノールに加え、目的生成物を沈殿させた。得られた白色沈殿をメタノールで十分洗浄し、真空乾燥した。なお、得られたポリイミドは、上記式(15)で表される繰り返し単位を20モル%含んでいる。
(ジアミンの合成)
上記式(10)で表されるジアミン(以下、「EBMB」という)を上記式(14)および(15)に示す方法により合成した。具体的な合成方法を以下に示す。
中間体TFBDを上記式(14)に示す方法によって合成した。まず窒素雰囲気下、三つ口フラスコに濃塩酸24mL、水100mLを入れ、この水溶液中に3.0128g(9.99mmol)のTFMBを加えて撹拌した。−4℃のこの溶液に、1.3802g(30mmol)の亜硝酸ナトリウムを水8mLで溶解した水溶液をシリンジで滴下した。滴下終了後、得られた溶液を−4℃に保ったまま、2時間撹拌し、0.1009g(10mmol)の尿素を加えて更に30分間撹拌してA液とした。
1.4002g(4.35mmol)のTFBD、7.4mLのTHF、1.4mL(17.4mmol)のピリジン溶液を、4−ニトロベンゼンカルボン酸クロライド(4−NBC)を2.8mLのTHFに溶解した溶液に氷浴下シリンジを用いて添加した。その結果黄白色の沈澱が生じた。12時間後、多量の水に再沈殿して、1日撹拌した。得られた黄白色沈澱を濾過し、洗浄後、濾過回収した。得られた粉末を100℃で12時間減圧乾燥し、EBMB前駆体であるニトロ化合物(以下、EBNBとする)を得た。収量は、2.1672g、収率は80.3%であった。
4.0041g(6.4539mmol)のEBNB、0.4295gのPd/Cを120mLのエタノールに溶解および分散した。得られた溶液に70℃にて水素ガスをバブリングし11時間反応を行なった。反応終点は薄層クロマトグラフィーにより確認した。反応終了後、反応混合物を熱ろ過し、ろ液を水中に滴下したところ白色沈殿を生じた。12時間攪拌後、得られた粉末を分取し、水で十分洗浄した。その後80℃で12時間減圧乾燥を行い、EBMB粗生成物3.2505g(収率:89.9%)を得た。
0.8406g(1.5mmol)のEBMB、0.8377g(1.5mmol)のABMBを3.91gのNMPに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え、更にNMPを加えて固形分濃度16.0重量%にて室温で7時間攪拌した。得られた溶液(ポリイミド前駆体)の固有粘度は、2.5dL/gであった。この溶液中に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下でゆっくりと滴下し、その後24時間攪拌した。得られた溶液を大量のメタノールに加え、目的生成物を沈殿させた。得られた白色沈殿をメタノールで十分洗浄し、真空乾燥した。
0.9607g(3mmol)のTFMBをDMAc3.8108gに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え室温にて9時間攪拌した。得られた溶液をDMAcによって固形分濃度13.6重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下で加え、その後24時間攪拌した。得られた溶液をメタノールに加え、目的生成物を沈殿させた。得られた白色沈殿をメタノールで十分洗浄した。
0.7686g(2.4mmol)のTFMBと0.1364g(0.6mmol)のDABAとをDMAc3.6808gに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え室温にて9時間攪拌した。得られた溶液をDMAcによって固形分濃度12.4重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温で加え、その後24時間攪拌した。得られた溶液をメタノールに加え、目的ポリイミド粉末を沈殿させた。得られた白色沈殿をメタノールで十分洗浄した。
0.6725g(2.1mmol)のTFMBと0.2045g(0.9mmol)のDABAとをDMAc3.6155gに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え室温で9時間攪拌した。得られた溶液をDMAcによって固形分濃度12.5重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下で加えたところ、反応混合物がゲル化し、以降の操作を実施することができなかった。
0.5764g(1.8mmol)のTFMBと0.2727g(1.2mmol)のDABAとをDMAc3.5504gに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え室温にて9時間攪拌した。得られた溶液をDMAcによって固形分濃度12.5重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下で加えたところ、反応混合物がゲル化し、以降の操作を実施することができなかった。
0.6818g(3mmol)のDABAをDMAc3.160gに溶解した。得られた溶液に0.6725g(3mmol)のH’‐PMDAを加え室温にて9時間攪拌した。得られた溶液をDMAcによって固形分濃度12.5重量%に希釈後、得られた希釈液に3.0627g(30mmol)の無水酢酸と1.1865g(15mmol)のピリジンとの混合溶媒を室温下で加えたところ、不溶成分が析出し、以降の操作を実施することができなかった。
Claims (13)
- 下記式(1)で表されることを特徴とするジアミン。
- 下記式(2)で表されることを特徴とする請求項1に記載のジアミン。
- 下記式(3)で表される繰り返し単位を有することを特徴とするポリイミド。
- 下記式(4)で表される繰り返し単位を有することを特徴とする請求項3に記載のポリイミド。
- 下記式(5)で表される繰り返し単位を有することを特徴とする請求項3または4に記載のポリイミド。
- 下記式(6)で表される繰り返し単位を有することを特徴とする請求項3または4に記載のポリイミド。
- 下記式(7)で表される繰り返し単位をさらに有することを特徴とする請求項3〜6のいずれか一項に記載のポリイミド。
- 請求項3〜7のいずれか一項に記載のポリイミドから得られたポリイミドフィルム。
- 請求項8に記載のポリイミドフィルムを含有する基板。
- 請求項8に記載のポリイミドフィルムを含有するカラーフィルター。
- 請求項8に記載のポリイミドフィルムを含有する画像表示装置。
- 請求項8に記載のポリイミドフィルムを含有する光学材料。
- 請求項8に記載のポリイミドフィルムを含有する電子デバイス。
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WO2020232597A1 (zh) * | 2019-05-20 | 2020-11-26 | 广东生益科技股份有限公司 | 二胺化合物、其制备方法、热固性树脂组合物及其应用 |
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CN112062962B (zh) * | 2020-08-28 | 2023-07-04 | 浙江中科玖源新材料有限公司 | 一种聚酰亚胺及高耐热低膨胀透明聚酰亚胺薄膜 |
CN112375010B (zh) * | 2020-09-27 | 2023-03-10 | 浙江中科玖源新材料有限公司 | 一种新型二胺、聚酰亚胺及聚酰亚胺薄膜 |
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JPH05203952A (ja) * | 1992-01-23 | 1993-08-13 | Japan Synthetic Rubber Co Ltd | 液晶配向剤 |
JP3226615B2 (ja) * | 1992-08-12 | 2001-11-05 | 三井化学株式会社 | ポリイミドおよびその製造方法 |
JPH0733876A (ja) * | 1993-07-16 | 1995-02-03 | Shin Etsu Chem Co Ltd | ポリイミド及びその製造方法 |
US5478914A (en) * | 1993-07-16 | 1995-12-26 | Shin-Etsu Chemical Co., Ltd. | Polyimides and processes for preparaing the same |
US5990261A (en) | 1996-08-29 | 1999-11-23 | Mitsui Chemicals, Inc. | Organic optical component |
TWI335455B (en) * | 2005-09-22 | 2011-01-01 | Ind Tech Res Inst | Liquid crystal display device |
JP5315496B2 (ja) * | 2008-01-18 | 2013-10-16 | 和光純薬工業株式会社 | 新規な(1s,2s,4r,5r)−シクロヘキサンテトラカルボン酸二無水物及びその利用 |
CN102666659B (zh) * | 2009-11-26 | 2014-03-12 | 株式会社钟化 | 光学膜、光学膜的制造方法、透明基板、图像显示装置以及太阳能电池 |
CN101834015B (zh) * | 2010-03-31 | 2011-12-21 | 鞍山华辉光电子材料科技有限公司 | 聚酰亚胺衬底柔性透明导电膜及其制备方法 |
CN101831074A (zh) * | 2010-04-30 | 2010-09-15 | 辽宁科技大学 | 一种新型含氟共聚聚酰亚胺及其制备方法 |
JP5443311B2 (ja) * | 2010-09-14 | 2014-03-19 | 株式会社カネカ | ポリイミド前駆体、ポリイミド樹脂およびその利用 |
CN102250354A (zh) * | 2011-05-28 | 2011-11-23 | 东华大学 | 一种聚酰亚胺及其制备方法 |
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JP5581463B2 (ja) | 2014-08-27 |
US20150011726A1 (en) | 2015-01-08 |
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