JP2012251080A5 - - Google Patents
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- Publication number
- JP2012251080A5 JP2012251080A5 JP2011125171A JP2011125171A JP2012251080A5 JP 2012251080 A5 JP2012251080 A5 JP 2012251080A5 JP 2011125171 A JP2011125171 A JP 2011125171A JP 2011125171 A JP2011125171 A JP 2011125171A JP 2012251080 A5 JP2012251080 A5 JP 2012251080A5
- Authority
- JP
- Japan
- Prior art keywords
- bis
- dianhydride
- polyimide
- group
- aminophenoxy
- 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
Links
- -1 alicyclic acid anhydride Chemical class 0.000 claims description 17
- 229920001721 polyimide Polymers 0.000 claims description 15
- 239000004642 Polyimide Substances 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000004984 aromatic diamines Chemical class 0.000 claims description 5
- 150000004985 diamines Chemical class 0.000 claims description 5
- 150000008065 acid anhydrides Chemical class 0.000 claims description 4
- 239000002966 varnish Substances 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229920005575 poly(amic acid) Polymers 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000000853 adhesive Substances 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 238000004132 cross linking Methods 0.000 claims 1
- 230000009477 glass transition Effects 0.000 claims 1
- 150000008282 halocarbons Chemical group 0.000 claims 1
- 238000000465 moulding Methods 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- 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 51
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 22
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
- 239000002253 acid Substances 0.000 description 9
- 239000004805 Cyclohexane-1,2-dicarboxylic acid Substances 0.000 description 8
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 150000002430 hydrocarbons Chemical group 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
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 2
- ICNFHJVPAJKPHW-UHFFFAOYSA-N 4,4'-Thiodianiline Chemical compound C1=CC(N)=CC=C1SC1=CC=C(N)C=C1 ICNFHJVPAJKPHW-UHFFFAOYSA-N 0.000 description 2
- MQAHXEQUBNDFGI-UHFFFAOYSA-N 5-[4-[2-[4-[(1,3-dioxo-2-benzofuran-5-yl)oxy]phenyl]propan-2-yl]phenoxy]-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(OC2=CC=C(C=C2)C(C)(C=2C=CC(OC=3C=C4C(=O)OC(=O)C4=CC=3)=CC=2)C)=C1 MQAHXEQUBNDFGI-UHFFFAOYSA-N 0.000 description 2
- NTLBZIURMIOQMG-UHFFFAOYSA-N C1=C(C(=CC=2OC3=CC(=C(C=C3CC12)C(=O)O)C(=O)O)C(=O)O)C(=O)O Chemical compound C1=C(C(=CC=2OC3=CC(=C(C=C3CC12)C(=O)O)C(=O)O)C(=O)O)C(=O)O NTLBZIURMIOQMG-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- YDSWCNNOKPMOTP-UHFFFAOYSA-N mellitic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(O)=O)=C(C(O)=O)C(C(O)=O)=C1C(O)=O YDSWCNNOKPMOTP-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 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
- OLQWMCSSZKNOLQ-ZXZARUISSA-N (3s)-3-[(3r)-2,5-dioxooxolan-3-yl]oxolane-2,5-dione Chemical compound O=C1OC(=O)C[C@H]1[C@@H]1C(=O)OC(=O)C1 OLQWMCSSZKNOLQ-ZXZARUISSA-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
- MNUHUVIZSPCLFF-UHFFFAOYSA-N 1-methylhept-6-ene-1,2,4,5-tetracarboxylic acid Chemical compound OC(=O)C(C)C(C(O)=O)CC(C(O)=O)C(C=C)C(O)=O MNUHUVIZSPCLFF-UHFFFAOYSA-N 0.000 description 1
- AWXPOFLDGZARPN-UHFFFAOYSA-N 2-[2-[2-[2-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1N AWXPOFLDGZARPN-UHFFFAOYSA-N 0.000 description 1
- DPKUNLWBBFHYDO-UHFFFAOYSA-N 2-[2-[3-[2-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC(OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)N)=C1 DPKUNLWBBFHYDO-UHFFFAOYSA-N 0.000 description 1
- ZSKKUMVHJJUXFR-UHFFFAOYSA-N 2-[3-[2-[3-(2-amino-3-propylphenoxy)phenoxy]phenoxy]phenoxy]-6-propylaniline Chemical compound CCCC1=CC=CC(OC=2C=C(OC=3C(=CC=CC=3)OC=3C=C(OC=4C(=C(CCC)C=CC=4)N)C=CC=3)C=CC=2)=C1N ZSKKUMVHJJUXFR-UHFFFAOYSA-N 0.000 description 1
- LLHLUXSWEPNHQT-UHFFFAOYSA-N 2-[3-[2-[3-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC(OC=2C(=CC=CC=2)OC=2C=C(OC=3C(=CC=CC=3)N)C=CC=2)=C1 LLHLUXSWEPNHQT-UHFFFAOYSA-N 0.000 description 1
- RQLOCJDEICYIDJ-UHFFFAOYSA-N 2-[3-[3-[3-(2-aminophenoxy)phenoxy]-5-butan-2-ylphenoxy]phenoxy]aniline Chemical compound C=1C(OC=2C=C(OC=3C(=CC=CC=3)N)C=CC=2)=CC(C(C)CC)=CC=1OC(C=1)=CC=CC=1OC1=CC=CC=C1N RQLOCJDEICYIDJ-UHFFFAOYSA-N 0.000 description 1
- RFDJEHMKNKYQDD-UHFFFAOYSA-N 2-[3-[3-[3-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC(OC=2C=C(OC=3C=C(OC=4C(=CC=CC=4)N)C=CC=3)C=CC=2)=C1 RFDJEHMKNKYQDD-UHFFFAOYSA-N 0.000 description 1
- PHMICAZPRIOSKN-UHFFFAOYSA-N 2-[3-[4-[3-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC(OC=2C=CC(OC=3C=C(OC=4C(=CC=CC=4)N)C=CC=3)=CC=2)=C1 PHMICAZPRIOSKN-UHFFFAOYSA-N 0.000 description 1
- ZFVVYDARMPANRE-UHFFFAOYSA-N 2-[4-[2-[4-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1N ZFVVYDARMPANRE-UHFFFAOYSA-N 0.000 description 1
- MSELOKBZDHROGO-UHFFFAOYSA-N 2-[4-[3-[4-(2-amino-6-methylphenoxy)phenoxy]phenoxy]phenoxy]-3-methylaniline Chemical compound CC1=CC=CC(N)=C1OC(C=C1)=CC=C1OC1=CC=CC(OC=2C=CC(OC=3C(=CC=CC=3C)N)=CC=2)=C1 MSELOKBZDHROGO-UHFFFAOYSA-N 0.000 description 1
- DRFYLELUESOFHU-UHFFFAOYSA-N 2-[4-[3-[4-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC(C=C1)=CC=C1OC1=CC=CC(OC=2C=CC(OC=3C(=CC=CC=3)N)=CC=2)=C1 DRFYLELUESOFHU-UHFFFAOYSA-N 0.000 description 1
- NVEOWWNUWVUQKN-UHFFFAOYSA-N 2-[4-[4-(2-aminophenoxy)phenyl]sulfinylphenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=C(S(=O)C=2C=CC(OC=3C(=CC=CC=3)N)=CC=2)C=C1 NVEOWWNUWVUQKN-UHFFFAOYSA-N 0.000 description 1
- GQQJHQUCWZTXEI-UHFFFAOYSA-N 2-[4-[4-[4-(2-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC(C=C1)=CC=C1OC1=CC=CC=C1N GQQJHQUCWZTXEI-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- SMDGQEQWSSYZKX-UHFFFAOYSA-N 3-(2,3-dicarboxyphenoxy)phthalic acid Chemical compound OC(=O)C1=CC=CC(OC=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O SMDGQEQWSSYZKX-UHFFFAOYSA-N 0.000 description 1
- GWHLJVMSZRKEAQ-UHFFFAOYSA-N 3-(2,3-dicarboxyphenyl)phthalic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=C(C(O)=O)C=CC=2)C(O)=O)=C1C(O)=O GWHLJVMSZRKEAQ-UHFFFAOYSA-N 0.000 description 1
- LXJLFVRAWOOQDR-UHFFFAOYSA-N 3-(3-aminophenoxy)aniline Chemical compound NC1=CC=CC(OC=2C=C(N)C=CC=2)=C1 LXJLFVRAWOOQDR-UHFFFAOYSA-N 0.000 description 1
- JFEXPVDGVLNUSC-UHFFFAOYSA-N 3-(3-aminophenyl)sulfanylaniline Chemical compound NC1=CC=CC(SC=2C=C(N)C=CC=2)=C1 JFEXPVDGVLNUSC-UHFFFAOYSA-N 0.000 description 1
- QHWXZLXQXAZQTO-UHFFFAOYSA-N 3-(3-aminophenyl)sulfinylaniline Chemical compound NC1=CC=CC(S(=O)C=2C=C(N)C=CC=2)=C1 QHWXZLXQXAZQTO-UHFFFAOYSA-N 0.000 description 1
- ZBMISJGHVWNWTE-UHFFFAOYSA-N 3-(4-aminophenoxy)aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC(N)=C1 ZBMISJGHVWNWTE-UHFFFAOYSA-N 0.000 description 1
- HDGMNVDCJJQDKD-UHFFFAOYSA-N 3-(4-aminophenyl)sulfinylaniline Chemical compound C1=CC(N)=CC=C1S(=O)C1=CC=CC(N)=C1 HDGMNVDCJJQDKD-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZDBWYUOUYNQZBM-UHFFFAOYSA-N 3-(aminomethyl)aniline Chemical compound NCC1=CC=CC(N)=C1 ZDBWYUOUYNQZBM-UHFFFAOYSA-N 0.000 description 1
- CKOFBUUFHALZGK-UHFFFAOYSA-N 3-[(3-aminophenyl)methyl]aniline Chemical compound NC1=CC=CC(CC=2C=C(N)C=CC=2)=C1 CKOFBUUFHALZGK-UHFFFAOYSA-N 0.000 description 1
- FGWQCROGAHMWSU-UHFFFAOYSA-N 3-[(4-aminophenyl)methyl]aniline Chemical compound C1=CC(N)=CC=C1CC1=CC=CC(N)=C1 FGWQCROGAHMWSU-UHFFFAOYSA-N 0.000 description 1
- OKUDCAZKFLIUAG-UHFFFAOYSA-N 3-[2-[2-[2-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)OC=2C(=CC=CC=2)OC=2C=C(N)C=CC=2)=C1 OKUDCAZKFLIUAG-UHFFFAOYSA-N 0.000 description 1
- CBHLYWRJXWSALB-UHFFFAOYSA-N 3-[2-[3-[2-(3-aminophenoxy)-4-methylphenoxy]phenoxy]-5-methylphenoxy]aniline Chemical compound C=1C=CC(N)=CC=1OC1=CC(C)=CC=C1OC(C=1)=CC=CC=1OC1=CC=C(C)C=C1OC1=CC=CC(N)=C1 CBHLYWRJXWSALB-UHFFFAOYSA-N 0.000 description 1
- BFDRCGKYIOFJAS-UHFFFAOYSA-N 3-[2-[3-[2-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)OC=2C=C(OC=3C(=CC=CC=3)OC=3C=C(N)C=CC=3)C=CC=2)=C1 BFDRCGKYIOFJAS-UHFFFAOYSA-N 0.000 description 1
- XOJSSTAPKXGHPD-UHFFFAOYSA-N 3-[2-[4-[2-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C(=CC=CC=2)OC=2C=CC(OC=3C(=CC=CC=3)OC=3C=C(N)C=CC=3)=CC=2)=C1 XOJSSTAPKXGHPD-UHFFFAOYSA-N 0.000 description 1
- MDWKZQBHNFKUSS-UHFFFAOYSA-N 3-[3-(2-methylphenoxy)phenoxy]aniline Chemical compound NC=1C=C(OC=2C=C(OC3=C(C=CC=C3)C)C=CC2)C=CC1 MDWKZQBHNFKUSS-UHFFFAOYSA-N 0.000 description 1
- LHPFWCWGTRNXMY-UHFFFAOYSA-N 3-[3-[2-[3-(3-aminophenoxy)phenoxy]-4-methylphenoxy]phenoxy]aniline Chemical compound C=1C=CC(OC=2C=C(N)C=CC=2)=CC=1OC1=CC(C)=CC=C1OC(C=1)=CC=CC=1OC1=CC=CC(N)=C1 LHPFWCWGTRNXMY-UHFFFAOYSA-N 0.000 description 1
- BMPGRWIWWZYARC-UHFFFAOYSA-N 3-[3-[2-[3-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C(=CC=CC=3)OC=3C=C(OC=4C=C(N)C=CC=4)C=CC=3)C=CC=2)=C1 BMPGRWIWWZYARC-UHFFFAOYSA-N 0.000 description 1
- GOJPGBGHAVIMIE-UHFFFAOYSA-N 3-[3-[4-[3-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=CC(OC=4C=C(OC=5C=C(N)C=CC=5)C=CC=4)=CC=3)C=CC=2)=C1 GOJPGBGHAVIMIE-UHFFFAOYSA-N 0.000 description 1
- LBPVOEHZEWAJKQ-UHFFFAOYSA-N 3-[4-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 LBPVOEHZEWAJKQ-UHFFFAOYSA-N 0.000 description 1
- UQHPRIRSWZEGEK-UHFFFAOYSA-N 3-[4-[1-[4-(3-aminophenoxy)phenyl]ethyl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 UQHPRIRSWZEGEK-UHFFFAOYSA-N 0.000 description 1
- FKRWBHYUXXHEEF-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenoxy]phenoxy]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(OC=3C(=CC=CC=3)OC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 FKRWBHYUXXHEEF-UHFFFAOYSA-N 0.000 description 1
- KOUQMRHSPOKPBD-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]butan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(CC)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 KOUQMRHSPOKPBD-UHFFFAOYSA-N 0.000 description 1
- BDROEGDWWLIVJF-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]ethyl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(CCC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 BDROEGDWWLIVJF-UHFFFAOYSA-N 0.000 description 1
- NYRFBMFAUFUULG-UHFFFAOYSA-N 3-[4-[2-[4-(3-aminophenoxy)phenyl]propan-2-yl]phenoxy]aniline Chemical compound C=1C=C(OC=2C=C(N)C=CC=2)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=CC(N)=C1 NYRFBMFAUFUULG-UHFFFAOYSA-N 0.000 description 1
- AMFRAQQDHUSYSZ-UHFFFAOYSA-N 3-[4-[3-[4-(3-aminophenoxy)phenoxy]-2,5-dimethylphenoxy]phenoxy]aniline Chemical compound CC=1C(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=CC(C)=CC=1OC(C=C1)=CC=C1OC1=CC=CC(N)=C1 AMFRAQQDHUSYSZ-UHFFFAOYSA-N 0.000 description 1
- VUCUWNCTOJOFDO-UHFFFAOYSA-N 3-[4-[3-[4-(3-aminophenoxy)phenoxy]-2-ethylphenoxy]phenoxy]aniline Chemical compound C1=CC=C(OC=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)C(CC)=C1OC(C=C1)=CC=C1OC1=CC=CC(N)=C1 VUCUWNCTOJOFDO-UHFFFAOYSA-N 0.000 description 1
- JERFEOKUSPGKGV-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfanylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(SC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 JERFEOKUSPGKGV-UHFFFAOYSA-N 0.000 description 1
- VTHWGYHNEDIPTO-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfinylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 VTHWGYHNEDIPTO-UHFFFAOYSA-N 0.000 description 1
- WCXGOVYROJJXHA-UHFFFAOYSA-N 3-[4-[4-(3-aminophenoxy)phenyl]sulfonylphenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(=CC=2)S(=O)(=O)C=2C=CC(OC=3C=C(N)C=CC=3)=CC=2)=C1 WCXGOVYROJJXHA-UHFFFAOYSA-N 0.000 description 1
- YSMXOEWEUZTWAK-UHFFFAOYSA-N 3-[4-[[4-(3-aminophenoxy)phenyl]methyl]phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=CC(CC=3C=CC(OC=4C=C(N)C=CC=4)=CC=3)=CC=2)=C1 YSMXOEWEUZTWAK-UHFFFAOYSA-N 0.000 description 1
- XMMFKXRGHKXAGG-UHFFFAOYSA-N 3-fluoro-1h-pyrrole Chemical compound FC=1C=CNC=1 XMMFKXRGHKXAGG-UHFFFAOYSA-N 0.000 description 1
- FYYYKXFEKMGYLZ-UHFFFAOYSA-N 4-(1,3-dioxo-2-benzofuran-5-yl)-2-benzofuran-1,3-dione Chemical compound C=1C=C2C(=O)OC(=O)C2=CC=1C1=CC=CC2=C1C(=O)OC2=O FYYYKXFEKMGYLZ-UHFFFAOYSA-N 0.000 description 1
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| KR102181466B1 (ko) * | 2015-03-31 | 2020-11-23 | 아사히 가세이 가부시키가이샤 | 폴리이미드 필름, 폴리이미드 바니시, 폴리이미드 필름을 이용한 제품 및 적층체 |
| JP6821451B2 (ja) * | 2016-01-25 | 2021-01-27 | 日本エイアンドエル株式会社 | ゴム組成物及びその製造方法、配合物、ならびに、ゴム組成物におけるシリカの歩留り比率向上方法 |
| US11421079B2 (en) * | 2016-03-14 | 2022-08-23 | Mitsubishi Gas Chemical Company, Inc. | Method for controlling polyimide backbone structure and method for producing polyimide |
| JP7029119B2 (ja) * | 2017-02-03 | 2022-03-03 | 国立研究開発法人理化学研究所 | 積層構造体およびその製造方法、ならびにフレキシブル・エレクトロニクス素子の製造方法 |
| KR101905112B1 (ko) | 2018-07-02 | 2018-10-08 | (주)오알켐 | 인쇄회로기판용 코팅 조성물 및 이의 제조방법 |
| JP7463964B2 (ja) * | 2018-08-24 | 2024-04-09 | 三菱瓦斯化学株式会社 | ポリイミド樹脂、ポリイミドワニス及びポリイミドフィルム |
| JP7286011B2 (ja) * | 2020-09-23 | 2023-06-02 | 積水化学工業株式会社 | 仮固定材、及び、電子部品の製造方法 |
| CN114989432B (zh) * | 2022-07-08 | 2023-05-05 | 中国地质大学（北京） | 一种聚酰亚胺及其制备方法和应用、热塑性聚酰亚胺工程塑料及其制备方法和应用 |
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| JP2537179B2 (ja) * | 1985-09-19 | 1996-09-25 | 三井東圧化学株式会社 | ポリイミドおよびポリイミドよりなる耐熱性接着剤 |
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| JP2006199945A (ja) * | 2004-12-24 | 2006-08-03 | Mitsubishi Gas Chem Co Inc | 低吸水性ポリイミド樹脂およびその製造方法 |
| WO2009069688A1 (ja) * | 2007-11-30 | 2009-06-04 | Mitsui Chemicals, Inc. | ポリイミド系複合材料およびそのフィルム |
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