DE3490169C2 - - Google Patents
Info
- Publication number
- DE3490169C2 DE3490169C2 DE19843490169 DE3490169A DE3490169C2 DE 3490169 C2 DE3490169 C2 DE 3490169C2 DE 19843490169 DE19843490169 DE 19843490169 DE 3490169 A DE3490169 A DE 3490169A DE 3490169 C2 DE3490169 C2 DE 3490169C2
- Authority
- DE
- Germany
- Prior art keywords
- bis
- groups
- same manner
- general formula
- following
- 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.)
- Expired
Links
- 229920001721 polyimide Polymers 0.000 claims abstract description 52
- 229920005575 poly(amic acid) Polymers 0.000 claims abstract description 39
- 239000004642 Polyimide Substances 0.000 claims abstract description 28
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 125000005907 alkyl ester group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000463 material Substances 0.000 abstract description 7
- 239000011248 coating agent Substances 0.000 abstract description 2
- 238000000576 coating method Methods 0.000 abstract description 2
- 239000004065 semiconductor Substances 0.000 abstract description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 45
- 238000010521 absorption reaction Methods 0.000 description 27
- 238000005979 thermal decomposition reaction Methods 0.000 description 23
- 239000002966 varnish Substances 0.000 description 21
- 150000004985 diamines Chemical class 0.000 description 14
- ANSXAPJVJOKRDJ-UHFFFAOYSA-N furo[3,4-f][2]benzofuran-1,3,5,7-tetrone Chemical compound C1=C2C(=O)OC(=O)C2=CC2=C1C(=O)OC2=O ANSXAPJVJOKRDJ-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 9
- -1 aromatic Tetracarboxylic anhydride Chemical class 0.000 description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 7
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 230000000052 comparative effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 150000008065 acid anhydrides Chemical class 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 230000002829 reductive effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- DPCDFSDBIWVMJC-UHFFFAOYSA-N 4-[4-[4-[4-amino-3-(trifluoromethyl)phenoxy]phenyl]phenoxy]-2-(trifluoromethyl)aniline Chemical group C1=C(C(F)(F)F)C(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=C(C(N)=CC=3)C(F)(F)F)=CC=2)C=C1 DPCDFSDBIWVMJC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 150000004984 aromatic diamines Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 description 2
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical group C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=CC(C(O)=O)=C1C(O)=O NBAUUNCGSMAPFM-UHFFFAOYSA-N 0.000 description 2
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 2
- IOUVQFAYPGDXFG-UHFFFAOYSA-N 4-[4-[2-[4-(3,4-dicarboxyphenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=C(C(C(O)=O)=CC=3)C(O)=O)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 IOUVQFAYPGDXFG-UHFFFAOYSA-N 0.000 description 2
- HHLMWQDRYZAENA-UHFFFAOYSA-N 4-[4-[2-[4-(4-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC1=CC=C(C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)(C(F)(F)F)C(F)(F)F)C=C1 HHLMWQDRYZAENA-UHFFFAOYSA-N 0.000 description 2
- HYDATEKARGDBKU-UHFFFAOYSA-N 4-[4-[4-(4-aminophenoxy)phenyl]phenoxy]aniline Chemical group C1=CC(N)=CC=C1OC1=CC=C(C=2C=CC(OC=3C=CC(N)=CC=3)=CC=2)C=C1 HYDATEKARGDBKU-UHFFFAOYSA-N 0.000 description 2
- LACZRKUWKHQVKS-UHFFFAOYSA-N 4-[4-[4-amino-2-(trifluoromethyl)phenoxy]phenoxy]-3-(trifluoromethyl)aniline Chemical compound FC(F)(F)C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1C(F)(F)F LACZRKUWKHQVKS-UHFFFAOYSA-N 0.000 description 2
- VQVIHDPBMFABCQ-UHFFFAOYSA-N 5-(1,3-dioxo-2-benzofuran-5-carbonyl)-2-benzofuran-1,3-dione Chemical compound C1=C2C(=O)OC(=O)C2=CC(C(C=2C=C3C(=O)OC(=O)C3=CC=2)=O)=C1 VQVIHDPBMFABCQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 230000005260 alpha ray Effects 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical group C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 229910001873 dinitrogen Inorganic materials 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 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
- 239000011737 fluorine Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- KAICRBBQCRKMPO-UHFFFAOYSA-N phosphoric acid;pyridine-3,4-diamine Chemical compound OP(O)(O)=O.NC1=CC=NC=C1N KAICRBBQCRKMPO-UHFFFAOYSA-N 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 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
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 2-(trifluoromethyl)benzene-1,4-diamine Chemical compound NC1=CC=C(N)C(C(F)(F)F)=C1 ZQQOGBKIFPCFMJ-UHFFFAOYSA-N 0.000 description 1
- IOHPPIBXAKZWGA-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)-3,4,5,6-tetrakis(trifluoromethyl)phenoxy]aniline Chemical compound NC1=CC=CC=C1OC(C(=C(C(=C1C(F)(F)F)C(F)(F)F)C(F)(F)F)C(F)(F)F)=C1OC1=CC=CC=C1N IOHPPIBXAKZWGA-UHFFFAOYSA-N 0.000 description 1
- KDGNBLYSSKCVAN-UHFFFAOYSA-N 2-[2-(2-aminophenoxy)-3,4-bis(trifluoromethyl)phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1OC1=CC=CC=C1N KDGNBLYSSKCVAN-UHFFFAOYSA-N 0.000 description 1
- MQZCBPWIFIEALZ-UHFFFAOYSA-N 2-[2-[2-[2-(2-aminophenoxy)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-yl]phenoxy]aniline Chemical compound NC1=CC=CC=C1OC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1OC1=CC=CC=C1N MQZCBPWIFIEALZ-UHFFFAOYSA-N 0.000 description 1
- IXWWWWDWQPOLBR-UHFFFAOYSA-N 2-[3-(2-aminophenyl)-1,1,2,2,3,3-hexafluoropropyl]aniline Chemical compound NC1=CC=CC=C1C(F)(F)C(F)(F)C(F)(F)C1=CC=CC=C1N IXWWWWDWQPOLBR-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 description 1
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 1
- PWTKZYBDXDXRMR-UHFFFAOYSA-N 3,4,5,6-tetrakis(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=C(N)C(C(F)(F)F)=C(C(F)(F)F)C(C(F)(F)F)=C1C(F)(F)F PWTKZYBDXDXRMR-UHFFFAOYSA-N 0.000 description 1
- JXMTULYAQORCGH-UHFFFAOYSA-N 3-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=CC(C(O)=O)=C1C(O)=O JXMTULYAQORCGH-UHFFFAOYSA-N 0.000 description 1
- PQFRTJPVZSPBFI-UHFFFAOYSA-N 3-(trifluoromethyl)benzene-1,2-diamine Chemical compound NC1=CC=CC(C(F)(F)F)=C1N PQFRTJPVZSPBFI-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- LFBALUPVVFCEPA-UHFFFAOYSA-N 4-(3,4-dicarboxyphenyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C(C(O)=O)=C1 LFBALUPVVFCEPA-UHFFFAOYSA-N 0.000 description 1
- KHYXYOGWAIYVBD-UHFFFAOYSA-N 4-(4-propylphenoxy)aniline Chemical compound C1=CC(CCC)=CC=C1OC1=CC=C(N)C=C1 KHYXYOGWAIYVBD-UHFFFAOYSA-N 0.000 description 1
- GEYAGBVEAJGCFB-UHFFFAOYSA-N 4-[2-(3,4-dicarboxyphenyl)propan-2-yl]phthalic acid Chemical compound C=1C=C(C(O)=O)C(C(O)=O)=CC=1C(C)(C)C1=CC=C(C(O)=O)C(C(O)=O)=C1 GEYAGBVEAJGCFB-UHFFFAOYSA-N 0.000 description 1
- IOSOEOCUMAIZRA-UHFFFAOYSA-N 4-[2-(4-aminophenyl)phenyl]aniline Chemical group C1=CC(N)=CC=C1C1=CC=CC=C1C1=CC=C(N)C=C1 IOSOEOCUMAIZRA-UHFFFAOYSA-N 0.000 description 1
- ZYEDGEXYGKWJPB-UHFFFAOYSA-N 4-[2-(4-aminophenyl)propan-2-yl]aniline Chemical compound C=1C=C(N)C=CC=1C(C)(C)C1=CC=C(N)C=C1 ZYEDGEXYGKWJPB-UHFFFAOYSA-N 0.000 description 1
- LTKJRDQWPMBSFN-UHFFFAOYSA-N 4-[3-(4-aminophenyl)-1,1,2,2,3,3-hexafluoropropyl]aniline Chemical compound C1=CC(N)=CC=C1C(F)(F)C(F)(F)C(F)(F)C1=CC=C(N)C=C1 LTKJRDQWPMBSFN-UHFFFAOYSA-N 0.000 description 1
- JCRRFJIVUPSNTA-UHFFFAOYSA-N 4-[4-(4-aminophenoxy)phenoxy]aniline Chemical compound C1=CC(N)=CC=C1OC(C=C1)=CC=C1OC1=CC=C(N)C=C1 JCRRFJIVUPSNTA-UHFFFAOYSA-N 0.000 description 1
- KJLPSBMDOIVXSN-UHFFFAOYSA-N 4-[4-[2-[4-(3,4-dicarboxyphenoxy)phenyl]propan-2-yl]phenoxy]phthalic acid Chemical compound C=1C=C(OC=2C=C(C(C(O)=O)=CC=2)C(O)=O)C=CC=1C(C)(C)C(C=C1)=CC=C1OC1=CC=C(C(O)=O)C(C(O)=O)=C1 KJLPSBMDOIVXSN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- FPAKXKXRPMFMLR-UHFFFAOYSA-N 4-[5-(4-aminophenyl)-1,1,2,2,3,3,4,4,5,5-decafluoropentyl]aniline Chemical compound C1=CC(N)=CC=C1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1=CC=C(N)C=C1 FPAKXKXRPMFMLR-UHFFFAOYSA-N 0.000 description 1
- CFPIGEXZPWTNOR-UHFFFAOYSA-N 4-chloro-1-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1C(F)(F)F CFPIGEXZPWTNOR-UHFFFAOYSA-N 0.000 description 1
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- JFRNSGLDDWKXOZ-UHFFFAOYSA-N C1=CC=C(C(=C1)C2=CC=CC=C2OC3=CC=CC=C3N)C(C(F)(F)F)C(F)(F)F Chemical compound C1=CC=C(C(=C1)C2=CC=CC=C2OC3=CC=CC=C3N)C(C(F)(F)F)C(F)(F)F JFRNSGLDDWKXOZ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 244000292411 Excoecaria agallocha Species 0.000 description 1
- XUUVPVYGCCIKBH-UHFFFAOYSA-N FC(F)(F)NC1=C(OC2=CC=C(C=C2)C2=CC=C(C=C2)OC2=C(C=CC=C2)NC(F)(F)F)C=CC=C1 Chemical group FC(F)(F)NC1=C(OC2=CC=C(C=C2)C2=CC=C(C=C2)OC2=C(C=CC=C2)NC(F)(F)F)C=CC=C1 XUUVPVYGCCIKBH-UHFFFAOYSA-N 0.000 description 1
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- BMBPXWXOUULOJW-UHFFFAOYSA-N NC(C=C1)=CC(C(F)(F)F)=C1OC(C(C(F)(F)F)=C1)=C(C(F)(F)F)C=C1C(C=C1C(F)(F)F)=CC(C(F)(F)F)=C1OC(C=C1)=C(C(F)(F)F)C=C1N Chemical group NC(C=C1)=CC(C(F)(F)F)=C1OC(C(C(F)(F)F)=C1)=C(C(F)(F)F)C=C1C(C=C1C(F)(F)F)=CC(C(F)(F)F)=C1OC(C=C1)=C(C(F)(F)F)C=C1N BMBPXWXOUULOJW-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical class C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- ZCILODAAHLISPY-UHFFFAOYSA-N biphenyl ether Natural products C1=C(CC=C)C(O)=CC(OC=2C(=CC(CC=C)=CC=2)O)=C1 ZCILODAAHLISPY-UHFFFAOYSA-N 0.000 description 1
- DGZXRBRWCYWFCI-UHFFFAOYSA-N bis[4-amino-3-(trifluoromethyl)phenyl]methanone Chemical compound C1=C(C(F)(F)F)C(N)=CC=C1C(=O)C1=CC=C(N)C(C(F)(F)F)=C1 DGZXRBRWCYWFCI-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000013058 crude material Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004427 diamine group Chemical group 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000012776 electronic material Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 229940018564 m-phenylenediamine Drugs 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- INNSUDKSFZEUGG-UHFFFAOYSA-N n-(trifluoromethyl)-2-[2-[2-(trifluoromethylamino)phenoxy]phenoxy]aniline Chemical compound FC(F)(F)NC1=CC=CC=C1OC1=CC=CC=C1OC1=CC=CC=C1NC(F)(F)F INNSUDKSFZEUGG-UHFFFAOYSA-N 0.000 description 1
- OBKARQMATMRWQZ-UHFFFAOYSA-N naphthalene-1,2,5,6-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 OBKARQMATMRWQZ-UHFFFAOYSA-N 0.000 description 1
- OLAPPGSPBNVTRF-UHFFFAOYSA-N naphthalene-1,4,5,8-tetracarboxylic acid Chemical compound C1=CC(C(O)=O)=C2C(C(=O)O)=CC=C(C(O)=O)C2=C1C(O)=O OLAPPGSPBNVTRF-UHFFFAOYSA-N 0.000 description 1
- KQSABULTKYLFEV-UHFFFAOYSA-N naphthalene-1,5-diamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1N KQSABULTKYLFEV-UHFFFAOYSA-N 0.000 description 1
- DOBFTMLCEYUAQC-UHFFFAOYSA-N naphthalene-2,3,6,7-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C=C2C=C(C(O)=O)C(C(=O)O)=CC2=C1 DOBFTMLCEYUAQC-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- FVDOBFPYBSDRKH-UHFFFAOYSA-N perylene-3,4,9,10-tetracarboxylic acid Chemical group C=12C3=CC=C(C(O)=O)C2=C(C(O)=O)C=CC=1C1=CC=C(C(O)=O)C2=C1C3=CC=C2C(=O)O FVDOBFPYBSDRKH-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000005476 soldering Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- 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
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Laminated Bodies (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Wire Bonding (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6208083A JPS59189122A (ja) | 1983-04-11 | 1983-04-11 | 含フッ素ポリアミド酸及びポリイミドの製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3490169C2 true DE3490169C2 (enrdf_load_stackoverflow) | 1989-07-20 |
Family
ID=13189725
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843490169 Pending DE3490169T (de) | 1983-04-11 | 1984-04-11 | Fluorhaltige Polyamidsäure und Polyimid |
| DE19843490169 Expired DE3490169C2 (enrdf_load_stackoverflow) | 1983-04-11 | 1984-04-11 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19843490169 Pending DE3490169T (de) | 1983-04-11 | 1984-04-11 | Fluorhaltige Polyamidsäure und Polyimid |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS59189122A (enrdf_load_stackoverflow) |
| DE (2) | DE3490169T (enrdf_load_stackoverflow) |
| WO (1) | WO1984004102A1 (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413194A1 (en) * | 1989-08-17 | 1991-02-20 | Occidental Chemical Corporation | Novel bis m-benzotrifluoride compounds |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0231781B1 (en) * | 1986-01-22 | 1992-04-01 | Hitachi, Ltd. | Liquid crystal display element |
| US4876329A (en) * | 1988-06-28 | 1989-10-24 | Amoco Corporation | Polyimide polymers and copolymers using 3,5-diaminobenzotrifluoride |
| KR910000832A (ko) * | 1988-06-28 | 1991-01-30 | 랄프 챨스 메더스트 | 인터레벨 유전체 및 기질 피복물용의 저유전상수 및 저수분흡수율을 갖는 폴리이미드 및 코폴리이미드 |
| JP2657700B2 (ja) * | 1988-08-08 | 1997-09-24 | 日本電信電話株式会社 | 含フッ素ポリイミド光学材料 |
| JPH0253827A (ja) * | 1988-08-17 | 1990-02-22 | Kanegafuchi Chem Ind Co Ltd | ポリイミド共重合体 |
| JP2799217B2 (ja) * | 1990-03-30 | 1998-09-17 | 財団法人相模中央化学研究所 | 含フッ素ジアミノベンゼン誘導体およびポリイミド |
| US5233018A (en) * | 1990-09-28 | 1993-08-03 | Nippon Telegraph And Telephone Corporation | Perfluorinated polyimide, perfluorinated poly(amic acid), starting compounds therefor, and methods for preparing them |
| JP2851019B2 (ja) * | 1990-09-28 | 1999-01-27 | 日本電信電話株式会社 | 全フッ素化ポリイミド，全フッ素化ポリアミド酸およびそれらの製造方法 |
| US5484879A (en) * | 1990-12-17 | 1996-01-16 | Occidental Chemical Corporation | Polyimides containing fluorine |
| KR20010087502A (ko) | 2000-03-07 | 2001-09-21 | 윤종용 | 광학용 폴리이미드 단량체, 폴리이미드 화합물 및 그 제조방법 |
| JP4962046B2 (ja) * | 2007-03-01 | 2012-06-27 | 東レ株式会社 | ポリイミドフィルムおよびその製造方法 |
| JP7150335B2 (ja) * | 2019-01-16 | 2022-10-11 | セイカ株式会社 | ４つの芳香環を有するジアミノ又はジニトロベンゼン化合物、およびその製造方法、並びにポリイミド |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1077243A (en) * | 1965-05-18 | 1967-07-26 | Monsanto Chemicals | Polyimides |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS57180633A (en) * | 1981-04-30 | 1982-11-06 | Hitachi Ltd | Curable polyimide resin composition |
| JPS58180531A (ja) * | 1982-04-19 | 1983-10-22 | Hitachi Ltd | 含フツ素ポリイミド、アミド酸並びにそれらの製造方法 |
-
1983
- 1983-04-11 JP JP6208083A patent/JPS59189122A/ja active Granted
-
1984
- 1984-04-11 DE DE19843490169 patent/DE3490169T/de active Pending
- 1984-04-11 DE DE19843490169 patent/DE3490169C2/de not_active Expired
- 1984-04-11 WO PCT/JP1984/000182 patent/WO1984004102A1/ja active Application Filing
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1077243A (en) * | 1965-05-18 | 1967-07-26 | Monsanto Chemicals | Polyimides |
Non-Patent Citations (1)
| Title |
|---|
| Pat. Abstr. Jap. 144 C 148 der JP 180 633 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0413194A1 (en) * | 1989-08-17 | 1991-02-20 | Occidental Chemical Corporation | Novel bis m-benzotrifluoride compounds |
| US5498691A (en) * | 1989-08-17 | 1996-03-12 | Occidental Chemical Corporation | Bis-m-benzotrifluoride compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0214365B2 (enrdf_load_stackoverflow) | 1990-04-06 |
| WO1984004102A1 (en) | 1984-10-25 |
| JPS59189122A (ja) | 1984-10-26 |
| DE3490169T (de) | 1985-05-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Free format text: STREHL, P., DIPL.-ING. DIPL.-WIRTSCH.-ING. SCHUEBEL-HOPF, U., DIPL.-CHEM. DR.RER.NAT., PAT.-ANWAELTE, 8000 MUENCHEN |