JPH0225378B2 - - Google Patents
Info
- Publication number
- JPH0225378B2 JPH0225378B2 JP18352083A JP18352083A JPH0225378B2 JP H0225378 B2 JPH0225378 B2 JP H0225378B2 JP 18352083 A JP18352083 A JP 18352083A JP 18352083 A JP18352083 A JP 18352083A JP H0225378 B2 JPH0225378 B2 JP H0225378B2
- Authority
- JP
- Japan
- Prior art keywords
- polyimide
- general formula
- formula
- mol
- solution
- 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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 46
- -1 aromatic diamine compound Chemical class 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 10
- JVERADGGGBYHNP-UHFFFAOYSA-N 5-phenylbenzene-1,2,3,4-tetracarboxylic acid Chemical compound OC(=O)C1=C(C(O)=O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1C(O)=O JVERADGGGBYHNP-UHFFFAOYSA-N 0.000 claims description 9
- 150000004985 diamines Chemical class 0.000 claims description 8
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 238000005259 measurement Methods 0.000 claims description 2
- 125000000962 organic group Chemical group 0.000 claims description 2
- 229920001721 polyimide Polymers 0.000 description 78
- 239000004642 Polyimide Substances 0.000 description 75
- 239000000243 solution Substances 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 239000003960 organic solvent Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 17
- 229920005575 poly(amic acid) Polymers 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 239000010408 film Substances 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000000034 method Methods 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229920000642 polymer Polymers 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 206010034972 Photosensitivity reaction Diseases 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000003999 initiator Substances 0.000 description 8
- 230000036211 photosensitivity Effects 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 7
- 238000000016 photochemical curing Methods 0.000 description 7
- 230000002165 photosensitisation Effects 0.000 description 7
- 239000003504 photosensitizing agent Substances 0.000 description 7
- 239000000463 material Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000004065 semiconductor Substances 0.000 description 5
- NFNNRBQJQRHJJH-UHFFFAOYSA-N (3,5-diaminophenyl)methyl prop-2-enoate Chemical compound NC1=CC(N)=CC(COC(=O)C=C)=C1 NFNNRBQJQRHJJH-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000002161 passivation Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 238000001308 synthesis method Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- FUWVHKHZYSBENS-UHFFFAOYSA-N (3,5-dinitrophenyl)methyl prop-2-enoate Chemical compound [O-][N+](=O)C1=CC(COC(=O)C=C)=CC([N+]([O-])=O)=C1 FUWVHKHZYSBENS-UHFFFAOYSA-N 0.000 description 3
- JNIVGHFBGSNDHF-UHFFFAOYSA-N 3,5-dinitro-n-phenylbenzamide Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC(C(=O)NC=2C=CC=CC=2)=C1 JNIVGHFBGSNDHF-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000740 bleeding effect Effects 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 230000001235 sensitizing effect Effects 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- GPHYIQCSMDYRGJ-UHFFFAOYSA-N (3,5-dinitrophenyl)methanol Chemical compound OCC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 GPHYIQCSMDYRGJ-UHFFFAOYSA-N 0.000 description 2
- YAHNTQADAFTJMN-UHFFFAOYSA-N 2,3-dinitro-n-phenylbenzamide Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)NC=2C=CC=CC=2)=C1[N+]([O-])=O YAHNTQADAFTJMN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 239000011810 insulating material Substances 0.000 description 2
- 238000009413 insulation Methods 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- WFSDXXBNBWRUNB-UHFFFAOYSA-N (2,3-dinitrophenyl)-phenylmethanone Chemical compound [O-][N+](=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1[N+]([O-])=O WFSDXXBNBWRUNB-UHFFFAOYSA-N 0.000 description 1
- DPNWQJXXLMZUPO-UHFFFAOYSA-N (2,4-diaminophenyl)methyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=C(N)C=C1N DPNWQJXXLMZUPO-UHFFFAOYSA-N 0.000 description 1
- LGBKSNBJDLXGIT-UHFFFAOYSA-N (2,4-diaminophenyl)methyl prop-2-enoate Chemical compound NC1=CC=C(COC(=O)C=C)C(N)=C1 LGBKSNBJDLXGIT-UHFFFAOYSA-N 0.000 description 1
- DBFYZSGZGUZONV-UHFFFAOYSA-N (3,5-diaminophenyl)-[4-(dimethylamino)naphthalen-1-yl]methanone Chemical compound C12=CC=CC=C2C(N(C)C)=CC=C1C(=O)C1=CC(N)=CC(N)=C1 DBFYZSGZGUZONV-UHFFFAOYSA-N 0.000 description 1
- FBMQNRKSAWNXBT-UHFFFAOYSA-N 1,4-diaminoanthracene-9,10-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(N)=CC=C2N FBMQNRKSAWNXBT-UHFFFAOYSA-N 0.000 description 1
- VWBVCOPVKXNMMZ-UHFFFAOYSA-N 1,5-diaminoanthracene-9,10-dione Chemical compound O=C1C2=C(N)C=CC=C2C(=O)C2=C1C=CC=C2N VWBVCOPVKXNMMZ-UHFFFAOYSA-N 0.000 description 1
- ILBBNQMSDGAAPF-UHFFFAOYSA-N 1-(6-hydroxy-6-methylcyclohexa-2,4-dien-1-yl)propan-1-one Chemical compound CCC(=O)C1C=CC=CC1(C)O ILBBNQMSDGAAPF-UHFFFAOYSA-N 0.000 description 1
- FYBFGAFWCBMEDG-UHFFFAOYSA-N 1-[3,5-di(prop-2-enoyl)-1,3,5-triazinan-1-yl]prop-2-en-1-one Chemical compound C=CC(=O)N1CN(C(=O)C=C)CN(C(=O)C=C)C1 FYBFGAFWCBMEDG-UHFFFAOYSA-N 0.000 description 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 description 1
- HABJWTMJQUIKSY-UHFFFAOYSA-N 10,10-bis(4-aminophenyl)anthracen-9-one Chemical compound C1=CC(N)=CC=C1C1(C=2C=CC(N)=CC=2)C2=CC=CC=C2C(=O)C2=CC=CC=C21 HABJWTMJQUIKSY-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- SIWJWTDBYVBOQL-UHFFFAOYSA-N 2,3-diamino-1,3-diphenylprop-2-en-1-one Chemical compound NC(=C(C1=CC=CC=C1)N)C(=O)C1=CC=CC=C1 SIWJWTDBYVBOQL-UHFFFAOYSA-N 0.000 description 1
- VPGHVKMBMPDAJD-UHFFFAOYSA-N 2,3-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC(C(Cl)=O)=C1[N+]([O-])=O VPGHVKMBMPDAJD-UHFFFAOYSA-N 0.000 description 1
- NNOHXABAQAGKRZ-UHFFFAOYSA-N 3,5-dinitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(C(Cl)=O)=CC([N+]([O-])=O)=C1 NNOHXABAQAGKRZ-UHFFFAOYSA-N 0.000 description 1
- NBAUUNCGSMAPFM-UHFFFAOYSA-N 3-(3,4-dicarboxyphenyl)phthalic acid Chemical compound 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 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
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 206010034960 Photophobia Diseases 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010070834 Sensitisation Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000009435 amidation Effects 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical group 0.000 description 1
- TUQQUUXMCKXGDI-UHFFFAOYSA-N bis(3-aminophenyl)methanone Chemical compound NC1=CC=CC(C(=O)C=2C=C(N)C=CC=2)=C1 TUQQUUXMCKXGDI-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- IGTXUDQEBIVUOK-UHFFFAOYSA-N dinitro(phenyl)methanol Chemical compound [O-][N+](=O)C([N+]([O-])=O)(O)C1=CC=CC=C1 IGTXUDQEBIVUOK-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- ORBFAMHUKZLWSD-UHFFFAOYSA-N ethyl 2-(dimethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(C)C ORBFAMHUKZLWSD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 208000013469 light sensitivity Diseases 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- VGKKPJXZCFDIFF-UHFFFAOYSA-N methyl 2-(2,2-dimethylhydrazinyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1NN(C)C VGKKPJXZCFDIFF-UHFFFAOYSA-N 0.000 description 1
- ATDSGWJPIKXGTA-UHFFFAOYSA-N methyl 2-[bis(methylamino)amino]benzoate Chemical compound CNN(NC)C1=CC=CC=C1C(=O)OC ATDSGWJPIKXGTA-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000679 solder Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18352083A JPS6072925A (ja) | 1983-09-30 | 1983-09-30 | 有機溶媒可溶性の感光性ポリイミド |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP18352083A JPS6072925A (ja) | 1983-09-30 | 1983-09-30 | 有機溶媒可溶性の感光性ポリイミド |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6072925A JPS6072925A (ja) | 1985-04-25 |
| JPH0225378B2 true JPH0225378B2 (US06650917-20031118-M00005.png) | 1990-06-01 |
Family
ID=16137281
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP18352083A Granted JPS6072925A (ja) | 1983-09-30 | 1983-09-30 | 有機溶媒可溶性の感光性ポリイミド |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6072925A (US06650917-20031118-M00005.png) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0778370B2 (ja) * | 1985-11-26 | 1995-08-23 | ヤマハ発動機株式会社 | ４行程エンジンの制御装置 |
| JPH0730703B2 (ja) * | 1986-03-07 | 1995-04-10 | ヤマハ発動機株式会社 | エンジンの排気制御装置 |
| JPH0243221A (ja) * | 1988-06-10 | 1990-02-13 | Occidental Chem Corp | 新規可溶性ポリイミドシロキサン及びその製法及び用途 |
| JP2540927B2 (ja) * | 1988-12-16 | 1996-10-09 | 日立化成工業株式会社 | 感光性樹脂組成物およびこれを用いた感光性エレメント |
| JP2785359B2 (ja) * | 1989-07-27 | 1998-08-13 | 日立化成工業株式会社 | ポリイミド系樹脂の製造法 |
| US5851736A (en) * | 1991-03-05 | 1998-12-22 | Nitto Denko Corporation | Heat-resistant photoresist composition, photosensitive substrate, and process for forming heat-resistant positive or negative pattern |
| IT1267642B1 (it) * | 1993-12-09 | 1997-02-07 | Honda Motor Co Ltd | Dispositivo di scarico |
| JP3709997B2 (ja) * | 1994-03-29 | 2005-10-26 | 日東電工株式会社 | 耐熱性ネガ型フォトレジスト組成物および感光性基材、ならびにネガ型パターン形成方法 |
| JP3232022B2 (ja) * | 1997-03-31 | 2001-11-26 | 信越化学工業株式会社 | 感光性樹脂組成物 |
| JP4529252B2 (ja) | 1999-09-28 | 2010-08-25 | 日立化成デュポンマイクロシステムズ株式会社 | ポジ型感光性樹脂組成物、パターンの製造法及び電子部品 |
| US7638254B2 (en) | 2004-05-07 | 2009-12-29 | Hitachi Chemical Dupont Microsystems Ltd | Positive photosensitive resin composition, method for forming pattern, and electronic part |
| JP4775261B2 (ja) | 2004-05-07 | 2011-09-21 | 日立化成デュポンマイクロシステムズ株式会社 | ポジ型感光性樹脂組成物、パターンの製造方法及び電子部品 |
| TWI407255B (zh) | 2005-09-22 | 2013-09-01 | Hitachi Chem Dupont Microsys | 負片型感光性樹脂組成物、圖案形成方法以及電子零件 |
| US8298747B2 (en) | 2007-03-12 | 2012-10-30 | Hitachi Chemical Dupont Microsystems, Ltd. | Photosensitive resin composition, process for producing patterned hardened film with use thereof and electronic part |
| JP5316417B2 (ja) | 2007-10-29 | 2013-10-16 | 日立化成デュポンマイクロシステムズ株式会社 | ポジ型感光性樹脂組成物、パターンの製造方法及び電子部品 |
| KR101010036B1 (ko) * | 2009-08-28 | 2011-01-21 | 주식회사 엘지화학 | 신규한 폴리아믹산, 이를 포함하는 감광성 수지 조성물 및 이로부터 제조된 드라이 필름 |
| JP5783166B2 (ja) * | 2010-02-26 | 2015-09-24 | 日産化学工業株式会社 | 液晶配向剤、液晶表示素子及びジアミン化合物 |
| JP6870289B2 (ja) * | 2016-11-17 | 2021-05-12 | Jsr株式会社 | 液晶配向剤、液晶素子の製造方法、液晶配向膜、液晶素子 |
-
1983
- 1983-09-30 JP JP18352083A patent/JPS6072925A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6072925A (ja) | 1985-04-25 |
