CN100547485C - Photosensitive resin composition - Google Patents
Photosensitive resin composition Download PDFInfo
- Publication number
- CN100547485C CN100547485C CNB2004800169298A CN200480016929A CN100547485C CN 100547485 C CN100547485 C CN 100547485C CN B2004800169298 A CNB2004800169298 A CN B2004800169298A CN 200480016929 A CN200480016929 A CN 200480016929A CN 100547485 C CN100547485 C CN 100547485C
- Authority
- CN
- China
- Prior art keywords
- resin composition
- photosensitive resin
- azo
- polymerization initiator
- cyano
- 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 - Fee Related
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 89
- -1 acryl Chemical group 0.000 claims abstract description 54
- 229920005989 resin Polymers 0.000 claims abstract description 53
- 239000011347 resin Substances 0.000 claims abstract description 51
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000003513 alkali Substances 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 14
- 239000011229 interlayer Substances 0.000 claims abstract description 14
- 239000004065 semiconductor Substances 0.000 claims abstract description 14
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 9
- 229930192627 Naphthoquinone Natural products 0.000 claims abstract description 8
- 150000002791 naphthoquinones Chemical class 0.000 claims abstract description 8
- 239000010408 film Substances 0.000 claims description 56
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 34
- 239000007869 azo polymerization initiator Substances 0.000 claims description 31
- 230000015572 biosynthetic process Effects 0.000 claims description 26
- 238000000034 method Methods 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 17
- 150000002989 phenols Chemical class 0.000 claims description 13
- 239000010409 thin film Substances 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 3
- 238000000059 patterning Methods 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 description 24
- 238000005886 esterification reaction Methods 0.000 description 17
- 239000000758 substrate Substances 0.000 description 17
- 230000032050 esterification Effects 0.000 description 16
- 238000011156 evaluation Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000004925 Acrylic resin Substances 0.000 description 9
- 229920000178 Acrylic resin Polymers 0.000 description 9
- 229920006243 acrylic copolymer Polymers 0.000 description 9
- 238000010438 heat treatment Methods 0.000 description 9
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000003505 polymerization initiator Substances 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 238000002834 transmittance Methods 0.000 description 8
- 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 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 6
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical class C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 5
- CQOZJDNCADWEKH-UHFFFAOYSA-N 2-[3,3-bis(2-hydroxyphenyl)propyl]phenol Chemical compound OC1=CC=CC=C1CCC(C=1C(=CC=CC=1)O)C1=CC=CC=C1O CQOZJDNCADWEKH-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- 239000001294 propane Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 4
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N alpha-isobutyric acid Natural products CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 238000007654 immersion Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 229960004063 propylene glycol Drugs 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- 230000008676 import Effects 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001259 photo etching Methods 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229940080818 propionamide Drugs 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 239000007767 bonding agent Substances 0.000 description 2
- VPSLGSSVPWVZFG-UHFFFAOYSA-N butan-2-yl propanoate Chemical compound CCC(C)OC(=O)CC VPSLGSSVPWVZFG-UHFFFAOYSA-N 0.000 description 2
- 239000001273 butane Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000007669 thermal treatment Methods 0.000 description 2
- AYYISYPLHCSQGL-UHFFFAOYSA-N (2,3,4,5,6-pentachlorophenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl AYYISYPLHCSQGL-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- OWEYKIWAZBBXJK-UHFFFAOYSA-N 1,1-Dichloro-2,2-bis(4-hydroxyphenyl)ethylene Chemical compound C1=CC(O)=CC=C1C(=C(Cl)Cl)C1=CC=C(O)C=C1 OWEYKIWAZBBXJK-UHFFFAOYSA-N 0.000 description 1
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 1
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 1
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 1
- BQMWZHUIGYNOAL-UHFFFAOYSA-N 1-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)C1=CC=CC=C1 BQMWZHUIGYNOAL-UHFFFAOYSA-N 0.000 description 1
- QZMIAUUXMOAEPN-UHFFFAOYSA-N 2-(2-methylpropoxy)butane Chemical compound CCC(C)OCC(C)C QZMIAUUXMOAEPN-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- WHBAYNMEIXUTJV-UHFFFAOYSA-N 2-chloroethyl prop-2-enoate Chemical compound ClCCOC(=O)C=C WHBAYNMEIXUTJV-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 1
- HIIBZFKVMXEQMR-UHFFFAOYSA-N 2-methyl-1-propan-2-yloxypropane Chemical compound CC(C)COC(C)C HIIBZFKVMXEQMR-UHFFFAOYSA-N 0.000 description 1
- WYYOJRLIWPYYHK-UHFFFAOYSA-N 2-methyl-3-(2-methylpropoxy)butane Chemical compound CC(C)COC(C)C(C)C WYYOJRLIWPYYHK-UHFFFAOYSA-N 0.000 description 1
- PFBMTLLGONBMCW-UHFFFAOYSA-N 2-methyl-4-(2-methylpropoxy)pentane Chemical compound CC(C)COC(C)CC(C)C PFBMTLLGONBMCW-UHFFFAOYSA-N 0.000 description 1
- RCEJCSULJQNRQQ-UHFFFAOYSA-N 2-methylbutanenitrile Chemical compound CCC(C)C#N RCEJCSULJQNRQQ-UHFFFAOYSA-N 0.000 description 1
- PDYXVZHOLWKKTM-UHFFFAOYSA-N 2-methylpropanamide;dihydrate Chemical compound O.O.CC(C)C(N)=O PDYXVZHOLWKKTM-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical group CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-UHFFFAOYSA-N 0.000 description 1
- ILZXXGLGJZQLTR-UHFFFAOYSA-N 2-phenylethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1=CC=CC=C1 ILZXXGLGJZQLTR-UHFFFAOYSA-N 0.000 description 1
- KUNMNFNVZOUSLL-UHFFFAOYSA-N 2-propan-2-yl-1,4,5,6-tetrahydropyrimidin-5-ol;dihydrochloride Chemical compound Cl.Cl.CC(C)C1=NCC(O)CN1 KUNMNFNVZOUSLL-UHFFFAOYSA-N 0.000 description 1
- ONUWOXUXSXUMTB-UHFFFAOYSA-N 3,3-dimethylbutan-2-yl propanoate Chemical compound CCC(=O)OC(C)C(C)(C)C ONUWOXUXSXUMTB-UHFFFAOYSA-N 0.000 description 1
- YFNNBSOTOXOZBT-UHFFFAOYSA-N 3,3-dimethylbutan-2-yloxymethylbenzene Chemical compound CC(C)(C)C(C)OCC1=CC=CC=C1 YFNNBSOTOXOZBT-UHFFFAOYSA-N 0.000 description 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 1
- DNJBAJYGHASTJZ-UHFFFAOYSA-N 4-[(4-hydroxy-3,5-dimethylphenyl)methyl]benzene-1,2,3-triol Chemical compound CC1=C(O)C(C)=CC(CC=2C(=C(O)C(O)=CC=2)O)=C1 DNJBAJYGHASTJZ-UHFFFAOYSA-N 0.000 description 1
- IJWIRZQYWANBMP-UHFFFAOYSA-N 4-[2-(4-hydroxy-3-propan-2-ylphenyl)propan-2-yl]-2-propan-2-ylphenol Chemical compound C1=C(O)C(C(C)C)=CC(C(C)(C)C=2C=C(C(O)=CC=2)C(C)C)=C1 IJWIRZQYWANBMP-UHFFFAOYSA-N 0.000 description 1
- WXYSZTISEJBRHW-UHFFFAOYSA-N 4-[2-[4-[1,1-bis(4-hydroxyphenyl)ethyl]phenyl]propan-2-yl]phenol Chemical compound C=1C=C(C(C)(C=2C=CC(O)=CC=2)C=2C=CC(O)=CC=2)C=CC=1C(C)(C)C1=CC=C(O)C=C1 WXYSZTISEJBRHW-UHFFFAOYSA-N 0.000 description 1
- RTANHMOFHGSZQO-UHFFFAOYSA-N 4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)C#N RTANHMOFHGSZQO-UHFFFAOYSA-N 0.000 description 1
- OHOHAFRZJYESCB-UHFFFAOYSA-N 4-methylpentan-2-yl propanoate Chemical compound CCC(=O)OC(C)CC(C)C OHOHAFRZJYESCB-UHFFFAOYSA-N 0.000 description 1
- JUMYFRGTFPZPQH-UHFFFAOYSA-N 4-methylpentan-2-yloxymethylbenzene Chemical compound CC(C)CC(C)OCC1=CC=CC=C1 JUMYFRGTFPZPQH-UHFFFAOYSA-N 0.000 description 1
- DUJMVKJJUANUMQ-UHFFFAOYSA-N 4-methylpentanenitrile Chemical compound CC(C)CCC#N DUJMVKJJUANUMQ-UHFFFAOYSA-N 0.000 description 1
- BMKFFLPVJHCPDD-UHFFFAOYSA-N 5-chloro-5-ethenylcyclohexa-1,3-diene Chemical compound C=CC1(Cl)CC=CC=C1 BMKFFLPVJHCPDD-UHFFFAOYSA-N 0.000 description 1
- IFFCENKANLEONZ-UHFFFAOYSA-N 5-methyl-2-propan-2-yl-4,5-dihydro-1h-imidazole;dihydrochloride Chemical compound Cl.Cl.CC(C)C1=NCC(C)N1 IFFCENKANLEONZ-UHFFFAOYSA-N 0.000 description 1
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
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Classifications
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- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
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- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/039—Macromolecular compounds which are photodegradable, e.g. positive electron resists
- G03F7/0392—Macromolecular compounds which are photodegradable, e.g. positive electron resists the macromolecular compound being present in a chemically amplified positive photoresist composition
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/094—Multilayer resist systems, e.g. planarising layers
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Engineering & Computer Science (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Materials For Photolithography (AREA)
- Photosensitive Polymer And Photoresist Processing (AREA)
- Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
- Polymerisation Methods In General (AREA)
Abstract
A kind ofly contain alkali soluble resins, have the photosensitizer of quinone diazido and the photosensitive resin composition of hardening agent, wherein, described alkali soluble resins is an acryl resin, described photosensitizer with quinone diazido is by the compound of following general formula (I) expression and the reaction product of naphthoquinones two triazo-compounds, described hardening agent contains epoxy radicals, have the planarization film that forms by described photosensitive resin composition or the flat-panel monitor or a semiconductor devices of interlayer dielectric film with a kind of: wherein, R
1, R
2, R
3And R
4Each independently represents H or C
1-2Alkyl, R
5And R
6Each independently represents C
1-2Alkyl.
Description
Technical field
The present invention relates to a kind of photosensitive resin composition, more specifically, relate to the photosensitive resin composition that is suitable for making semiconductor devices, flat-panel monitor (FPD) etc., particularly be fit to form the interlayer dielectric film of semiconductor devices, FPD etc. or the photosensitive resin composition of planarization film.
Background technology
Making the wide spectrum of circuit substrate that SIC (semiconductor integrated circuit) such as LSI or FPD display surface or manufacturing be used for thermal head etc., photoetching technique had been used up to now already, was used for forming microcomponent or realized retrofit.In photoetching technique, use the photosensitive resin composition of a kind of eurymeric or minus, be used for forming corrosion-resisting pattern.In recent years, be used for the interlayer dielectric film of SIC (semiconductor integrated circuit) or FPD etc. or the formation technology of planarization film, just receive publicity as the new application of these photosensitive resin compositions.Especially, market is very strong for the height of FPD display surface demand accurate and fine techniques, it is said that interlayer dielectric film that highly transparent and dielectric properties are good and planarization film are very important materials for obtaining the accurate and fine techniques of this class height.In progress to the many researchs that are used for the photosensitive resin composition that this class uses, and, various compositions have been proposed, for example, JP 7-248629 A and JP 8-262709 A.But, because the composition that is suitable for interlayer dielectric film etc. that proposes so far needs crosslinking chemical to improve thermotolerance for this reason, so they are its bad stability as time passes.Therefore, compare, pay particular attention to for the storage environment of described composition with the usual eurymeric resist that is used for retrofit.And, in the manufacturing process of FPD display surface, adopt circulation developer (it is the developer that is repeated to use) to carry out photoetching.When being used for making the eurymeric resist of thin film transistor (TFT) (TFT) and contain the photosensitive resin composition of the above crosslinking chemical when this circulation developer mixes, will cause such problem, be that crosslinking chemical contained in eurymeric resist and the composition reacts, produce a large amount of deposits that is insoluble to this developer.On the other hand, in JP 5-297582 A, a kind of photosensitive resin composition is disclosed, it can form have high resolving power, the corrosion-resisting pattern of high aspect ratio (aspectratio), high-fire resistance and good cross-sectional profile, it is by using polyol and 1 a kind of as general formula (I) expression subsequently, and the esterification compound of 2-naphthoquinones diazido sulfonic acid is as the photosensitizer realization.But, in the document, the use as the acryl resin of alkali soluble resins is not explained, photosensitive resin composition improved stability is not as time passes explained yet.
Consider above-mentioned situation, purpose of the present invention provides a kind of photosensitive resin composition, even if after higher temperature cures, it still can keep the complanation on film surface, and can provide and have good transmittance and than the film of low-k more in the past, and in the photosensitive resin composition that contains alkali soluble resins and photosensitizer, it has good stable as time passes.
Another object of the present invention provides a kind of the have planarization film that formed by above-mentioned photosensitive resin composition or the FPD or the semiconductor devices of interlayer dielectric film.
In addition, another object of the present invention provides a kind of method that forms heat-pesistant thin film, may further comprise the steps: adopt above-mentioned photosensitive resin composition carry out patterning, the Zone Full of patterned film is exposed and to it carry out subsequently after cure.
Summary of the invention
Result as fervent research and observation, the inventor finds, above-mentioned purpose can realize as photosensitizer that as alkali soluble resins and a kind of particular type photosensitizer described photosensitive resin composition contains a kind of alkali soluble resins and a kind of photosensitizer that contains the quinone diazido by use acryl resin in a kind of photosensitive resin composition.That is to say, by using above-mentioned photosensitive resin composition, a kind ofly after thermal treatment, for example can keep the film surface planarization in 1 hour and have the film of good transmittance and low-k even if just can obtain 220 ℃ of pyroprocessing, and, can obtain a kind of photosensitive resin composition that in long-time, has good stability as time passes, thereby realize the present invention.
That is to say, the present invention relates to the photosensitive resin composition of following (1)-(11) item.
(1) a kind ofly contains alkali soluble resins, has the photosensitizer of quinone diazido and the photosensitive resin composition of hardening agent, wherein, alkali soluble resins is an acryl resin, photosensitizer with quinone diazido is by the compound of following general formula (I) expression and the reaction product of naphthoquinones two triazo-compounds, hardening agent contains epoxy radicals
Wherein, R
1, R
2, R
3And R
4Each independently represents H or C
1-2Alkyl, R
5And R
6Each independently represents C
1-2Alkyl.
(2) above-mentioned (1) described photosensitive resin composition, also contain the phenolic compound by general formula (II) expression:
Wherein, R
11, R
12, R
13, R
14, R
15, R
16And R
17Each independently represents H, C
1-4Alkyl or
Each m and n are the integer of 0-2 independently, and a, b, c, d, e, f, g and h are the integer that satisfies the 0-5 of following relational expression: a+b≤5, c+d≤5, and e+f≤5, and g+h≤5, and i is the integer of 0-2.
(3) above-mentioned (1) or (a 2) described photosensitive resin composition also contains a kind of curing accelerator.
(4) each described photosensitive resin composition in above-mentioned (1)-(3), wherein, described acryl resin contains the formation unit that is derived from (methyl) alkyl acrylate and is derived from (methyl) acrylic acid formation unit.
(5) each described photosensitive resin composition in above-mentioned (1)-(4), wherein, described acryl resin contain quantity be 5-30mol% be derived from (methyl) acrylic acid formation unit.
(6) each described photosensitive resin composition in above-mentioned (1)-(5), wherein, the phenolic compound of being represented by above-mentioned general formula (II) is a kind of compound by following general formula (III) expression:
(7) each described photosensitive resin composition in above-mentioned (1)-(6), wherein, the weight-average molecular weight of described acryl resin is determined as 5000-30000 by polystyrene standard.
(8) each described photosensitive composition in above-mentioned (1)-(7), wherein, described alkali soluble resins is by using not synthetic the obtaining of azo polymerization initiator of cyano-containing.
(9) each described photosensitive composition in above-mentioned (1)-(7), wherein, described alkali soluble resins is to obtain by the azo polymerization initiator that uses cyano-containing is synthetic.
(10) each described photosensitive composition in above-mentioned (1)-(7), wherein, described alkali soluble resins is to obtain by the azo polymerization initiator of azo polymerization initiator that uses cyano-containing not simultaneously and cyano-containing is synthetic.
(11) each described photosensitive composition in above-mentioned (1)-(10), wherein, described alkali soluble resins is to obtain by the azo polymerization initiator of azo polymerization initiator that uses cyano-containing not simultaneously and cyano-containing is synthetic, and the mol ratio of the azo polymerization initiator of the azo polymerization initiator/cyano-containing of cyano-containing is not 20/80～80/20.
In addition, the present invention relates to following (12) and (a 13) described flat-panel monitor or semiconductor devices.
(12) have the planarization film that forms by each described photosensitive resin composition in above-mentioned (1)-(11) or the flat-panel monitor of interlayer dielectric film.
(13) have the planarization film that forms by each described photosensitive resin composition in above-mentioned (1)-(11) or the semiconductor devices of interlayer dielectric film.
(14) a kind of method that forms heat-pesistant thin film may further comprise the steps: adopt each described photosensitive resin composition in above-mentioned (1)-(11) to carry out patterning, the Zone Full of patterned film is exposed, and to it carry out subsequently after cure.
Now the present invention is done more detailed explanation.
Be suitable for the alkaline soluble acrylic resin of photosensitive resin composition of the present invention, can be any one and be used as the alkali soluble resins of used photosensitive resin so far.Any acryl resin, such as the synthetic alkaline soluble acrylic resin of azo polymerization initiator by adopting cyano-containing, by adopting the not synthetic alkaline soluble acrylic resin of azo polymerization initiator of cyano-containing, the azo polymerization initiator by adopting cyano-containing not and the synthetic alkaline soluble acrylic resin of azo polymerization initiator of cyano-containing, or the like, can preferably adopt.
As for the polymerization initiator of not cyano-containing used when synthesizing the alkaline soluble acrylic resin that is used for photosensitive resin composition of the present invention, that can enumerate has:
1,1 '-azo two (1-acetate-1-vinylbenzene),
1,1 '-azo two (1-propionyloxy (propionoxy)-1-vinylbenzene),
1,1 '-azo two (1-isobutoxy (isobutyloxy)-1-vinylbenzene),
1,1 '-azo two (1-neopentanoic acid base-1-vinylbenzene),
1,1 '-azo two (1-acetate-1-phenylpropyl alcohol alkane),
1,1 '-azo two [1-acetate-1-(p-methylphenyl) ethane],
1,1 '-azo two [1-acetate-1-(rubigan) ethane],
1,1 '-azo two (1-acetate-1-benzene butane),
Dimethyl 2,2 '-azo two (2 Methylpropionic acid ester),
1,1 '-azo two (1-chloro-1-vinylbenzene),
1,1 '-azo two (1-chloro-1-propane),
1,1 '-azo two [1-chloro-1-(p-methylphenyl) ethane],
1,1 '-azo two [1-chloro-1-(rubigan) ethane],
1,1 '-azo two (1-chloro-1-benzene butane),
2,2 '-azo two (2-acetate-3,3-dimethylbutane),
2,2 '-azo two (2-acetate-4-methylpentane),
2,2 '-azo two (2-propionyloxy-3,3-dimethylbutane),
2,2 '-azo two (2-propionyloxy-4-methylpentane),
2,2 '-azo two (2-isobutoxy (isobutoxy)-3,3-dimethylbutane),
2,2 '-azo two (2-isobutoxy-4-methylpentane),
2,2 '-azo two (2-neopentanoic acid base-3,3-dimethylbutane),
2,2 '-azo two (2-neopentanoic acid base-4-methylpentane),
2,2 '-azo two (2-benzoxy-3,3-dimethylbutane),
2,2 '-azo two (2-benzoxy-4-methylpentane),
2,2 '-azo two (2-acetate propane),
2,2 '-azo two (2-acetate butane),
2,2 '-azo two (2-acetate-3-methylbutane),
2,2 '-azo two (2-propionyloxy propane),
2,2 '-azo two (2-propionyloxy butane),
2,2 '-azo two (2-propionyloxy-3-methylpropane),
2,2 '-azo two (2-isobutoxy propane),
2,2 '-azo two (2-isobutoxy butane),
2,2 '-azo two (2-isobutoxy-3-methylbutane),
2,2 '-azo two (2-neopentanoic acid base propane),
2,2 '-azo two (2-neopentanoic acid base butane),
2,2 '-azo two (2-neopentanoic acid base-3-methylbutane),
2,2 '-azo two (2,4, the 4-trimethylpentane),
2,2 '-azo two (2-methylpropane),
1,1 '-azo two (1-methoxyl cyclohexane),
2,2 '-azo two (2-methyl-N-phenyl propionyl amidine) dihydrochloride,
2,2 '-azo two [N-(4-hydroxyphenyl)-2-methyl propionyl amidine] dihydrochloride,
2,2 '-azo two [2-methyl-N-(2-propenyl) propionyl amidine] dihydrochloride,
2,2 '-azo two [N-(2-hydroxyethyl)-2-methyl propionyl amidine] dihydrochloride,
2,2 '-azo two [2-(5-methyl-2-imidazoline-2-yl) propane] dihydrochloride,
2, and 2 '-azo two [2-(4,5,6,7-tetrahydrochysene-1H-1,3-diaza
-2-yl) propane] dihydrochloride,
2,2 '-azo two [2-(5-hydroxyl-3,4,5,6-tetrahydropyrimidine-2-yl) propane] dihydrochloride,
2,2 '-azo two [N-(2-propyl group)-2-methyl propanamide],
2,2 '-azo two [2-(2-imidazoline-2-yl) propane],
2,2 '-azo two two (the methylol)-2-hydroxyl-ethyls of 2-methyl-N-[] propionamide },
2,2 '-azo two 2-methyl-N-[1, two (methylol) ethyls of 1-]-propionamide },
2,2 '-azo two [2-methyl-N-(2-methylol) propionamide],
2,2 '-azo two (2-methyl propanamide) dihydrate, or the like.
Not in the azo polymerization initiator of cyano-containing, preferred polymerization initiator is at these:
1,1 '-azo two (1-acetate-1-vinylbenzene),
1,1 '-azo two (1-propionyloxy-1-vinylbenzene),
1,1 '-azo two (1-isobutoxy-1-vinylbenzene),
1,1 '-azo two (1-neopentanoic acid base-1-vinylbenzene),
1,1 '-azo two (1-acetate-1-phenylpropyl alcohol alkane),
1,1 '-azo two [1-acetate-1-(p-methylphenyl) ethane],
1,1 '-azo two [1-acetate-1-(rubigan) ethane],
1,1 '-azo two (1-acetate-1-benzene butane) and dimethyl 2,2 '-azo two (2 Methylpropionic acid ester).
The azo polymerization initiator of cyano-containing, that can enumerate has:
1,1 '-azo two (cyclohexane-1-nitrile),
2,2 '-azo two (2-methylbutyronitrile),
2,2 '-azoisobutyronitrile,
2,2 '-azo two (2, the 4-methyl pentane nitrile),
2,2 '-azo two (2,4-dimethyl-4-methoxyl valeronitrile), a kind of azo polymerization initiator of preferred cyano-containing is 2,2 '-azoisobutyronitrile.
For acryl resin is that the polymerization initiator of cyano-containing synthesizes the situation that resin that obtain and this is used as the acryl resin of photosensitive resin composition of the present invention as the synthetic polymerization initiator of acryl resin by adopting not, can form a kind of good film of fabulous light transmission and thermotolerance and solvent resistance that has.On the other hand, when use is synthesized the acryl resin that obtains by the polymerization initiator that adopts cyano-containing as polymerization initiator, then can obtain the good photosensitive resin composition of thermotolerance and solvent resistance.In addition, when the synthetic acryl resin that obtains of the azo polymerization initiator that uses azo polymerization initiator by adopting cyano-containing not and cyano-containing, just can obtain a kind of at the unusual photosensitive resin composition of excellence aspect multiple performances such as light transmission, solvent resistance, thermotolerance well balanced.In above-mentioned all scenario, every kind of photosensitive resin composition of the present invention is along with the stability of time all is extraordinary.
When the azo polymerization initiator of azo polymerization initiator that uses cyano-containing not and cyano-containing during together as polymerization initiator, usually, to use in the scope at 20: 80～80: 20 with its mol ratio, preferable range is 30: 70～70: 30.
As for the alkaline soluble acrylic resin that is used for photosensitive resin composition of the present invention, alkali solubility polyacrylate (a), alkali solubility polymethacrylate (b) can be proposed and contain at least a acrylate and at least a methacrylate as the alkali solubility that constitutes the unit poly-(acrylate-altogether-methacrylate) (c).These acryl resins can use separately, perhaps, use jointly with their two or more potpourri.As for these acryl resins, in order to make that described resin is alkali-soluble, containing a kind of organic acid monomer is preferred as the acryl resin of copolymer composition, still, can give described resin alkali-soluble copolymerization units, is not limited to organic acid monomer.
As for the monomer component that constitutes these alkali-soluble polyacrylic resins, but the monomer that acrylate, methacrylate, organic acid monomer and other copolymerization are arranged that can propose.As for the monomer component that constitutes these polymkeric substance, be preferred as the following acrylate that exemplifies, methacrylate and organic acid monomer.
Acrylate:
Methyl acrylate, acrylic acid ethyl ester, acrylic acid n-pro-pyl ester, n-butylacrylate, acrylic acid n-hexyl ester, acrylic acid isopropyl esters, acrylic acid isobutyl, acrylic acid tertiary butyl ester, acrylic acid cyclohexyl ester, acrylic acid benzyl ester, acrylic acid 2-chloro-ethyl ester, methyl-α-Lv Daibingxisuan ester, phenyl-alpha-brominated acrylate etc.
Methacrylate:
Methyl methacrylate, the methacrylic acid ethyl ester, methacrylic acid n-pro-pyl ester, the methacrylic acid n-butyl, methacrylic acid n-hexyl ester, the methacrylic acid isopropyl esters, the methacrylic acid isobutyl, the methacrylic acid tertiary butyl ester, the methacrylic acid cyclohexyl ester, the methacrylic acid benzyl ester, the methacrylic acid phenylester, methacrylic acid 1-phenylethylester, methacrylic acid 2-phenylethylester, methacrylic acid furfuryl group ester, methacrylic acid diphenyl methyl ester, methacrylic acid pentachloro-phenyl ester, naphthyl, IBOMA, the methacrylic acid hydroxyethyl ester, hydroxypropyl methacrylate etc.
Organic acid monomer:
Monocarboxylic acid as acrylic acid, methacrylic acid and butenoic acid and so on; Dicarboxylic acids and its dicarboxylic acid anhydride as itaconic acid, maleic acid, fumaric acid, citraconic acid and mesaconic acid and so on; 2-acryloyl hydrogenated phthalates, 2-acryloyl-oxy propyl group hydrogenated phthalates etc.
In addition, but the monomer of other copolymerization can exemplify maleic acid diester, dimethyl ester, styrene, styrene derivative, vinyl cyanide, (methyl) acrylamide, vinyl acetate, vinyl chloride, vinylidene chloride etc. are arranged.But the monomer of these other copolymerization can use if necessary, and its quantity should be the quantity in described acryl resin can be realized the scope of the object of the invention.
A kind of preferred acrylic resins of the present invention, be a kind of multipolymer that contains the formation unit that is derived from (methyl) alkyl acrylate and be derived from (methyl) acrylic acid formation unit, a kind of preferred acryl resin is to contain the acrylic acid described multipolymer of 5-30mol% (methyl).The preferable range that is applied to the weight-average molecular weight (being recorded by polystyrene standard) of the alkaline soluble acrylic resin among the present invention is 5,000-30,000.If molecular weight, then can cause the problem that solvent resistance and thermotolerance worsen less than 5,000,, then can cause the remaining problem of developing that takes place if molecular weight surpasses 30,000.
The photosensitizer with quinone diazido that is used for photosensitive resin composition of the present invention is a kind of by the phenolic compound of above-mentioned general formula (I) expression and the reaction product of naphthoquinones two triazo-compounds.By the phenolic compound of general formula (I) expression, for instance, that can enumerate has a compound by following general formula (I-a)-(I-c) expression.The synthetic of this compounds can be undertaken by known method, for example disclosed method among the JP 5-297582A etc.
On the other hand, naphthoquinones two triazo-compounds (it can react by the phenolic compound with general formula (I) expression and form esterification compound) can be any quinone di-azido compound, as long as it is the compound with quinone diazido.The example of quinone di-azido compound comprises quinone two nitrine sulfonic acid halides, as with 1, and 2-naphthoquinones two nitrine-5-sulfonic acid chloride, 1, the naphthoquinones two nitrine sulfonic acid chlorides and the benzoquinones two nitrine sulfonic acid chlorides of representative such as 2-naphthoquinones two nitrine-4-sulfonic acid chloride.Esterification be by the compound of above-mentioned general formula (I) expression and quinone two nitrine sulfonic acid halides in the presence of base catalyst such as NaOH, sodium carbonate, sodium bicarbonate or triethylamine, usually in-20 reacting realization to about 60 ℃ of temperature approximately.Esterification can be the part of hydroxyl of phenolic compound of general formula (I) expression or the esterification of its whole hydroxyls.Esterification yield can obtain suitable control by phenolic compound quantity of regulating general formula (I) expression and the compound quantity with quinone diazido.In this esterification, can obtain the esterification reaction mixture of different esterification numbers and esterification position.Therefore, esterification yield obtains as the mean values of these potpourris.And these reaction product can be used separately by single product, perhaps its two or more common use.In the present invention, by the phenolic compound of use general formula (I) expression and the reaction product of naphthoquinones two triazo-compounds, can obtain to have the photosensitive resin composition of excellent prolonged storage life, and, can form a kind of film with excellent light transmission, solvent resistance, thermotolerance and dielectricity.In the present invention, above-mentioned reaction product is normally being that the quantity of 1-30 weight portion is used with respect to 100 weight portion alkali soluble resinss in the photosensitive resin composition.And with regard to photosensitizer, other photosensitizer can use with above-mentioned reaction product, as long as do not hinder the object of the invention.
In photosensitive resin composition of the present invention, except the reaction product of the phenolic compound of above-mentioned alkaline soluble acrylic resin and above-mentioned general formula (I) expression and naphthoquinones two triazo-compounds, also preferably contain the phenolic compound of representing by above-mentioned general formula (II).And, in photosensitive resin composition of the present invention, have low molecular compound, normally be used for controlling rate of dissolution, and be used for improving the film residue ratio of photosensitive resin composition or being used for controlling light sensitivity as dissolution inhibitor by the phenolic hydroxyl group of above-mentioned general formula (II) expression.
Low molecular compound with phenolic hydroxyl group of above-mentioned general formula (II) expression, comprise orthoresol, metacresol, paracresol, 2, the 4-xylenols, 2, the 5-xylenols, 2, the 6-xylenols, bisphenol-A, B, C, E, F or G, 4,4 '; 4 "-methine triphenol, 2, two [(2-hydroxy-5-methyl base phenyl) the methyl]-4-methylphenols of 6-, 4,4 '-[1-[4-[1-(4-hydroxy phenyl)-1-Methylethyl] phenyl] ethylidene] bis-phenol, 4,4 '-[1-[4-[2-(4-hydroxy phenyl)-2-propyl group] phenyl] ethylidene] bis-phenol, 4,4 '; 4 "-ethylidine triphenol, two (4-hydroxy phenyl) methyl of 4-[]-the 2-thanatol, 4,4 '-[(2-hydroxy phenyl) methylene] two [2,3-xylenol], 4,4 '-[(3-hydroxy phenyl) methylene] two [2,6-xylenol], 4,4 '-[(4-hydroxy phenyl) methylene] two [2,6-xylenol], 2,2 '-[(2-hydroxy phenyl) methylene] two [3,5-xylenol], 2,2 '-[(4-hydroxy phenyl) methylene] two [3,5-xylenol], 4,4 '-[(3, the 4-dihydroxy phenyl) methylene] two [2,3,6-pseudocuminol], two (3-cyclohexyl-4-hydroxyl-6-aminomethyl phenyl) methyl of 4-[]-1, the 2-Benzenediol, 4,6-two [(3,5-dimethyl-4-hydroxy phenyl) methyl]-1,2,3-benzene triol, 4,4 '-[(2-hydroxy phenyl) methylene] two [3-methylphenols], 4,4 '; 4 "-(3-methyl isophthalic acid-propyl group-3-time base) triphenol, 4,4 '; 4 " 4 ' " four phenol-(1; 4-phenylene two methines); 2; 4,6-three [(3,5-dimethyl-4-hydroxy phenyl) methyl]-1; 3-Benzenediol; 2,4,6-three [(3,5-dimethyl-2-hydroxy phenyl) methyl]-1, the 3-Benzenediol, 4,4 '-[1-[4-[1-[4-hydroxyl-3, two [(hydroxy-3-methyl phenyl) methyl] phenyl of 5-]-1-Methylethyl] phenyl]-ethylidene] two [2, two (hydroxy-3-methyl phenyl) methyl of 6-] phenol etc.Have in the low molecular compound of the phenolic hydroxyl group of representing by above-mentioned general formula (II) at these, for instance, preferred compound comprises 4,4 ', 4 "-and methine triphenol, 2, two [(2-hydroxy-5-methyl base phenyl) the methyl]-4-methylphenols, 4 of 6-; 4 '-[1-[4-[1-(4-hydroxy phenyl)-1-Methylethyl] phenyl] ethylidene] bis-phenol, 4; 4 '-[1-[4-[2-(4-hydroxy phenyl)-2-propyl group] phenyl] ethylidene] bis-phenol, 4,4 ', 4 "-the ethylidine triphenol etc.
Have in the low molecular compound of phenolic hydroxyl group at these, the compound of being represented by above-mentioned general formula (III) or following general formula (IV) is preferred:
These have the consumption of the low molecular compound of phenolic hydroxyl group, with respect to the alkali soluble resins of 100 weight portions, are the 1-20 weight portion.
Preferably, a kind of hardening agent with epoxy radicals also can be attached among the photosensitive resin composition of the present invention.This hardening agent example with epoxy radicals comprises bisphenol-type epoxy resin, cresols phenolic resin varnish type epoxy resin, cycloaliphatic epoxy resin, diglycidyl ether type epoxy, glycidyl amine type epoxy resin, heterocyclic ring epoxy resins etc.But, can be applicable to the hardening agent among the present invention, be not limited only to above-mentioned polymer electrolyte epoxy compound, also comprise the glycidol ether of bisphenol-A or Bisphenol F etc., they are preferred applicable low molecule-type epoxy compounds.This preferable amount with hardening agent of epoxy radicals with respect to 100 weight portion alkali soluble resinss, is the 2-60 weight portion, is preferably the 10-40 weight portion.
In photosensitive resin composition of the present invention, also can contain curing accelerator to promote the cross-linking reaction between epoxy radicals and (methyl) acrylic acid.The curing accelerator example comprises aromatics sulfonium salt such as SI-60L, SI-80L, SI-100L and SI-110L, and (they are all by SanshinChemical Industry Co., Ltd. produce), diaza-bicyclo undecylene salt such as U-CATSA 102, U-CAT SA506, U-CAT SA603 and U-CAT 5002 (producing), U-CAT 5003 and U-CAT 18X (producing by San-Apro Ltd. respectively) by San-AproLtd., or the like.And imidazoles curing accelerator example comprises Quazol 1B2PZ (being produced by ShikokuChemicals Corp.) or the like.By in conjunction with these curing accelerators in photosensitive resin composition of the present invention, just can form cured film with good solvent resistance; Simultaneously, can also obtain to have as time passes the photosensitive resin composition of excellent stability.When adopting curing accelerator,, can realize that also the solvent resistance of cured film is improved even if when hardening agent quantity reduces.And, when alkali soluble resins is the synthetic acryl resin that obtains of the azo polymerization initiator combination of the azo polymerization initiator by using cyano-containing or azo polymerization initiator that uses cyano-containing not and cyano-containing, with independent use not the azo polymerization initiator of cyano-containing compare as polymerization initiator, can obtain the improvement of the solvent resistance of cured film as more preferably result.The curing accelerator quantity of adding with respect to the hardening agent that 100 weight portions have epoxy radicals, is preferably the 0.1-15 weight portion, more preferably the 1-10 weight portion.
As for dissolving alkali soluble resins among the present invention, photosensitizer and having the compound of phenolic hydroxyl group or the solvent of resin, what can exemplify has: ethylene glycol monoalkyl ether such as glycol monomethyl methyl ether, ethylene glycol monomethyl ether etc.; Ethylene glycol monoalkyl ether acetate such as ethylene glycol monomethyl ether acetate, ethylene glycol monomethyl ether acetate etc.; Propylene-glycol monoalky lether such as propylene glycol monomethyl ether, propylene glycol list ethylether etc.; Propylene-glycol monoalky lether acetic acid esters such as propylene glycol monomethyl ether, propylene glycol list ethylether acetic acid esters etc.; Lactate such as methyl lactate, ethyl lactate etc.; Aromatic hydrocarbons such as toluene, dimethylbenzene etc.; Ketone such as MEK, 2-heptanone, cyclohexanone etc.; Acid amides such as N,N-dimethylacetamide, N-Methyl pyrrolidone etc.; Lactone such as gamma-butyrolacton etc.; Like that.These solvents can use separately, also can use by its two or more potpourri.
In photosensitive resin composition of the present invention, if necessary, also can introduce bonding agent, surfactant etc.The example of bonding agent comprises alkyl imidazoline, butyric acid, alkyl acid, polyhydroxy styrene, polyvinyl methyl ether, tert-butyl group novolac resin, epoxy silane, epoxy polymer, silane etc.And the example of described surfactant comprises non-ionic surfactant such as polyglycol and its derivant, i.e. polypropylene glycol or polyoxyethylene lauryl ether; Fluorochemical surfactant such as Fluorad (trade name, Sumitomo 3M Co., the product of Ltd.), Megafac (trade name, Dai-Nippon Ink ﹠amp; Chemicals, the product of Inc.), Surflon (trade name, Asahi Glass Company, the product of Ltd.) and organosiloxane surfactant such as KP341 (trade name, Shin-Etsu Chemical Co., the product of Ltd.).
Photosensitive resin composition of the present invention is to be dissolved in the solvent by the mentioned component that will determine dosage to make.At this moment, every kind of composition can be dissolved in the solvent in advance separately, and before use, the confirmable dosage of the composition of every kind of dissolving mixes and prepares.Normally, described photosensitive resin composition solution is to use after adopting 0.2 μ m filtrator etc. to filter.
Photosensitive resin composition of the present invention adopts following method to form a kind of film with high dielectric property, high light transmittance, high-fire resistance and solvent resistance.This film can preferably and be suitable as planarization film or interlayer dielectric film etc.Its expression at first, is coated to photosensitive resin composition solution of the present invention on the substrate, then, described substrate is carried out prebake, to form film (photoresist) of described photosensitive resin composition.At this moment, the substrate that is coated with photosensitive resin composition on it can be the substrate of any known, as is used for the substrate of FPD or is used to form the substrate of semiconductor devices, as glass or silicon chip.Described substrate can be naked substrate or is formed with the substrate of oxidation film, nitride film, metal film etc. thereon, perhaps can be the substrate that is formed with circuit pattern or semiconductor element thereon.Then, this on-chip photoresist is exposed to through among the light of determining mask with pattern mode ground, develops by using a kind of alkaline developer, if necessary, clean, to form the film eurymeric pattern of described photosensitive resin composition.Will be through the film eurymeric pattern of this formation, after exposing, cure after it is carried out through Zone Full, like this, just can form and a kind of high temperature is had stable on heating film.It is also uncertain that this class has the reason why stable on heating film can form to high temperature, but, according to estimates, have the curing of the hardening agent of epoxy radicals, owing to obtain the promotion that photosensitizer when expose by Zone Full decomposes the acid that produces, thereby formation has the film of high-fire resistance.Formed high-fire resistance film eurymeric pattern can be used as semiconductor element, liquid crystal indicator and as the planarization film of the FPD of plasma scope and so on or interlayer dielectric film etc.Incidentally, be formed at the situation of substrate Zone Full for thermotolerance and solvent resistance film, the pattern mode is exposed or is developed and can not carry out.
In the formation of above-mentioned film, as for the coating method of described photosensitive resin composition solution, can adopt a kind of suitable method, for example spin-coating method, rolling method, flat method, spraying process, mobile rubbing method, the dip coating etc. of launching of being coated with.For instance, the light that is used to expose can comprise that ultraviolet ray is as g-line, i-line etc., far ultraviolet such as KrF excimer laser or ArF excimer laser etc., X-ray, electron beam etc.And developing method comprises the method that is applicable to that so far resist develops, as oar formula development method, immersion development method and swing immersion development method.Developer comprises inorganic base such as NaOH, potassium hydroxide, sodium carbonate and sodium silicate, ammonia, organic amine such as ethamine, propylamine, diethylamine, diethylaminoethanol and triethylamine, quaternary ammonium such as tetramethyl ammonium hydroxide etc.
Embodiment
To make more specific description to the present invention by embodiment now, still, be limitation of the present invention in any case these embodiment can not be interpreted as.
Synthesis example 1 (synthesizing of acrylic copolymer 1)
With 700g propylene glycol monomethyl ether, 171g methyl methacrylate, 90g methacrylic acid 2-hydroxypropyl ester, 39g methacrylic acid and 12.6g dimethyl 2,2 '-azo two (2 Methylpropionic acid ester), be poured into one and wear 2 of stirrer, condenser, thermometer and nitrogen ingress pipe, in the 000ml four neck flasks, mix, then heating, import nitrogen simultaneously, carry out polymerization, continue 8 hours at 85 ℃, obtain having weight-average molecular weight and be 11,000 acrylic copolymer 1.
Synthesis example 2 (synthesizing of acrylic copolymer 2)
With the 700g propylene glycol monomethyl ether, the 171g methyl methacrylate, 90g methacrylic acid 2-hydroxypropyl ester, the 39g methacrylic acid, 6.3g dimethyl 2,2 '-azo two (2 Methylpropionic acid ester) [molecular weight: 230.26] and 4.5g 2,2 '-azoisobutyronitrile [molecular weight: 164.21], be poured into one and worn stirrer, condenser, 2 of thermometer and nitrogen ingress pipe, in the 000ml four neck flasks, mix, then heating, import nitrogen simultaneously, carry out polymerization at 85 ℃, continue 8 hours, obtain having weight-average molecular weight and be 11,000 acrylic copolymer 2.
Synthesis example 3 (synthesizing of acrylic copolymer 3)
With 700g propylene glycol monomethyl ether, 171g methyl methacrylate, 90g methacrylic acid 2-hydroxypropyl ester, 39g methacrylic acid and 9g 2,2 '-azoisobutyronitrile, be poured into one and wear 2 of stirrer, condenser, thermometer and nitrogen ingress pipe, in the 000ml four neck flasks, mix, then heating, import nitrogen simultaneously, carry out polymerization, continue 8 hours at 85 ℃, obtain having weight-average molecular weight and be 11,000 acrylic copolymer 3.
Embodiment 1
The esterification products (esterification yield is 50%) of the acrylic copolymer following general formulas of 1,25 weight portions (V) expression that 100 weight portions are obtained in synthesis example 1, the phenolic compound of the above-mentioned general formula of 5 weight portions (III) expression, 10 weight portion Techmore VG3101L are (by MitsuiChemicals, Inc. produce), be dissolved in a kind of mixed solvent of forming by propylene glycol monomethyl ether and ethyl lactate (mixing ratio is 75: 25) as curing accelerator as hardening agent with epoxy radicals and 0.2 weight portion U-CATSA102 (producing) by San-Apro Ltd..Then, in order to prevent radial gauffer (so-called " streak " is formed on the surface of photoresist) when spin coating, add the 300ppm fluorochemical surfactant in described solution, Megafac R-08 is (by Dai-Nippon Chemicals ﹠amp; Inks Co., Inc. produces).After stirring described solution, described solution adopts 0.2 μ m filtrator to filter, to make photosensitive resin composition 1 of the present invention.
The formation of＜Thinfilm pattern 〉
Adopt spin-coating method, resulting photosensitive resin composition 1 is coated on 4 inches silicon chips, and on heating plate, cured 90 seconds in 100 ℃, form the photoresist that thickness is 3.0 μ m.Described etchant resist sees through a test pattern, by using the g+h+i-lines mask aligner PLA-501F that makes by Canon Inc., expose with optimum exposure dosage, described test pattern contains and has multiple different line thickness and have 1: 1 lines and the lines of interval width and intermittent pattern and have the contact hole pattern of multiple different-diameter, and adopt the aqueous solution of the tetramethyl ammonium hydroxide of 0.4wt% to develop at 23 ℃, continue 60 seconds, have lines and the intermittent pattern and the contact hole pattern of 1: 1 lines and interval width with formation.
＜solvent resistance evaluation 〉
Same way as described above, preparation has the glass substrate of Thinfilm pattern, and difference is to use the quartz glass substrate of 70X70mm size and does not carry out the pattern mode and expose.This glass substrate is immersed among 80 ℃ the Remover100 (being produced by Clariant (Japan) K.K.), continues 1 minute, afterwards, adopts pure water to clean, and cures again 15 minutes at 200 ℃.By using ultraviolet-visible spectrophotometer CARY4E (producing), when the glass substrate transmittance is 400nm, measures the preceding transmittance of immersion solvent and cure processing back transmittance again by Varian Inc..That is,, provide O, but this transmittance difference is 3% or then provides X when bigger for before the immersion solvent and cure the transmittance difference handled between the back again less than 3% situation.The result is as shown in table 1.
＜thermotolerance evaluation 〉
Formation by above-mentioned＜Thinfilm pattern〉described same way as carries out, and preparation has the substrate of the pattern of 1: 1 lines and interval width.In baking oven, it is heated at 220 ℃, continue 60 minutes.Have 10 μ m live widths and have 1: 1 lines and during the part of interval width in observation, when before the heating and the line width variation between the heating back then provide O during less than 1 μ m, when this is changed to 1 μ m or then provides X when bigger.The result is as shown in table 1.
＜time stability evaluation 〉
Be called sample A with one by making photosensitive resin composition 1 leave standstill the sample that obtained in 30 days, another is called sample B by making photosensitive resin composition 1 leave standstill the sample that obtained in 30 days in 23 ℃ in 5 ℃.Sample A and sample B are applied on 4 inches silicon chips by spin-coating method, then cure 90 seconds in 100 ℃ on heating plate, obtain the photoresist that thickness is 3.0 μ m.Described etchant resist sees through a test pattern, by using the g+h+i-lines mask aligner PLA-501F that makes by Canon Inc., expose with optimum exposure dosage, described test pattern contains and has multiple different line thickness and have 1: 1 lines and the lines of interval width and intermittent pattern and have the contact hole pattern of multiple different-diameter, and adopt the aqueous solution of the tetramethyl ammonium hydroxide of 0.4wt% to develop at 23 ℃, continue 60 seconds, have the lines and the intermittent pattern of 1: 1 lines and interval width and have the sectional hole patterns of multiple bore dia and void ratio with formation.Represent with % by the thickness of the thickness of the back etchant resist that develops and the coating back etchant resist ratio that obtains that is divided by, be defined as film residue ratio.When the difference of the film between sample A and sample B residue ratio then provides O less than 3% the time, the difference that remains ratio when this film is 3% or then provides X when bigger.The result is as shown in table 1.
Embodiment 2
Undertaken by embodiment 1 same way as, difference is to use the acrylic copolymer 2 instead of propylene acid copolymers 1 that obtain in the synthesis example 2, prepares photosensitive resin composition 2.Press embodiment 1 same way as,, carry out formation, solvent resistance evaluation, thermotolerance evaluation and the time stability evaluation of Thinfilm pattern by using this photosensitive resin composition 2.The result is as shown in table 1.
Embodiment 3
Undertaken by embodiment 1 same way as, difference is to use the acrylic copolymer 3 instead of propylene acid copolymers 1 that obtain in the synthesis example 3, prepares photosensitive resin composition 3.Press embodiment 1 same way as,, carry out formation, solvent resistance evaluation, thermotolerance evaluation and the time stability evaluation of Thinfilm pattern by using this photosensitive resin composition 3.The result is as shown in table 1.
Comparative Examples 1
Undertaken by embodiment 1 same way as, difference is to use the compound and 1 of above-mentioned general formula (III) expression, 25 weight portion esterification products of 2-naphthoquinones two nitrine-5-sulfonic acid chloride are as the esterification products of photosensitizer, but both do not used Techmore VG3101L (producing) by Mitsui Chemical Inc., do not use U-CAT SA 102 (producing) yet, and prepare photosensitive resin composition 4 by San-Apro Ltd..Press embodiment 1 same way as,, carry out formation, solvent resistance evaluation, thermotolerance evaluation and the time stability evaluation of Thinfilm pattern by applying this photosensitive resin composition 4.The result is as shown in table 1.
Comparative Examples 2
Undertaken by embodiment 1 same way as, difference is to use the compound and 1 of above-mentioned general formula (III) expression, and 25 weight portion esterification products of 2-naphthoquinones two nitrine-5-sulfonic acid chloride are as the esterification products of photosensitizer, and prepares photosensitive resin composition 5.Press embodiment 1 same way as,, carry out formation, solvent resistance evaluation, thermotolerance evaluation and the time stability evaluation of Thinfilm pattern by applying this photosensitive resin composition 5.The result is as shown in table 1.
Table 1
| Solvent resistance is estimated | Thermotolerance is estimated | Time stability is estimated | |
| Embodiment 1 | O | O | O |
| Embodiment 2 | O | O | O |
| Embodiment 3 | O | O | O |
| Comparative Examples 1 | X | X | O |
| Comparative Examples 2 | O | O | X |
Can know that from above-mentioned table 1 photosensitive resin composition of the present invention all is excellent, all is in well balanced state in solvent resistance, thermotolerance and time stability evaluation.And all etchant resists that formed by the photosensitive resin composition of these embodiment all have good dielectricity after thermal treatment.
The advantageous effects of invention
As mentioned above, photosensitive resin composition of the present invention has excellent time stability, and the multiple performance of the film that is formed by these photosensitive resin compositions also is excellent, such as light transmission, solvent resistance, heat resistance and the dielectric property of film. So it is particularly suitable for interlayer dielectric film, planarization film of flat-panel monitor, semiconductor element etc. etc.
Industrial usability
Photosensitive resin composition of the present invention is suitable for interlayer dielectric film and the planarization film of flat-panel monitor and semiconductor element.
Claims (14)
1. one kind contains alkali soluble resins, has the photosensitizer of quinone diazido and the photosensitive resin composition of hardening agent, wherein, described alkali soluble resins is an acryl resin, described photosensitizer with quinone diazido is by the compound of following general formula (I) expression and the reaction product of naphthoquinones two triazo-compounds, described hardening agent contains epoxy radicals
Wherein, R
1, R
2, R
3And R
4Each independently represents H or C
1-2Alkyl, R
5And R
6Each independently represents C
1-2Alkyl.
2. the described photosensitive resin composition of claim 1, also contain the phenolic compound by general formula (II) expression:
Wherein, R
11, R
12, R
13, R
14, R
15, R
16And R
17Each independently represents H, C
1-4Alkyl or
Each m and n are the integer of 0-2 independently, and a, b, c, d, e, f, g and h are the integer that satisfies the 0-5 of following relational expression: a+b≤5, c+d≤5, and e+f≤5, and g+h≤5, and i is the integer of 0-2.
3. the described photosensitive resin composition of claim 1 also contains a kind of curing accelerator.
4. each described photosensitive resin composition among the claim 1-3, wherein, described acryl resin contains the formation unit that is derived from (methyl) alkyl acrylate and is derived from (methyl) acrylic acid formation unit.
5. the described photosensitive resin composition of claim 1, wherein, described acryl resin contain quantity be 5-30mol% be derived from (methyl) acrylic acid formation unit.
6. the described photosensitive resin composition of claim 2 wherein, is a kind of compound by following formula (III) expression by the phenolic compound of above-mentioned general formula (II) expression:
7. the described photosensitive resin composition of claim 1, wherein, the weight-average molecular weight of described acryl resin is determined as 5 by polystyrene standard, 000-30,000.
8. the described photosensitive resin composition of claim 1, wherein, described alkali soluble resins is by using not synthetic the obtaining of azo polymerization initiator of cyano-containing.
9. the described photosensitive resin composition of claim 1, wherein, described alkali soluble resins is to obtain by the azo polymerization initiator that uses cyano-containing is synthetic.
10. the described photosensitive resin composition of claim 1, wherein, described alkali soluble resins is by using the not azo polymerization initiator of cyano-containing and synthetic the obtaining of azo polymerization initiator of cyano-containing simultaneously.
11. the described photosensitive resin composition of claim 10, wherein, described alkali soluble resins is to obtain by the azo polymerization initiator of azo polymerization initiator that uses cyano-containing not simultaneously and cyano-containing is synthetic, and the mol ratio of the azo polymerization initiator of the azo polymerization initiator/cyano-containing of cyano-containing is not 20/80～80/20.
12. have the planarization film that forms by each described photosensitive resin composition among the claim 1-11 or the flat-panel monitor of interlayer dielectric film.
13. have the planarization film that forms by each described photosensitive resin composition among the claim 1-11 or the semiconductor devices of interlayer dielectric film.
14. a method that forms heat-pesistant thin film may further comprise the steps: adopt that each described photosensitive resin composition carries out patterning among the claim 1-11, Zone Full exposed, and carry out subsequently after cure.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP182087/2003 | 2003-06-26 | ||
| JP2003182087A JP4099114B2 (en) | 2003-06-26 | 2003-06-26 | Photosensitive resin composition |
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| Publication Number | Publication Date |
|---|---|
| CN1806206A CN1806206A (en) | 2006-07-19 |
| CN100547485C true CN100547485C (en) | 2009-10-07 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB2004800169298A Expired - Fee Related CN100547485C (en) | 2003-06-26 | 2004-06-17 | Photosensitive resin composition |
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| Country | Link |
|---|---|
| JP (1) | JP4099114B2 (en) |
| KR (1) | KR100983210B1 (en) |
| CN (1) | CN100547485C (en) |
| TW (1) | TWI332121B (en) |
| WO (1) | WO2005001575A1 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105988288A (en) * | 2015-03-17 | 2016-10-05 | 东友精细化工有限公司 | Photosensitive resin composition, photocuring pattern and pattern display device |
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| JP5338352B2 (en) * | 2009-02-09 | 2013-11-13 | 日油株式会社 | Positive photosensitive resin composition |
| KR20110045418A (en) * | 2009-10-27 | 2011-05-04 | 삼성전자주식회사 | Photoresist composition and method of manufacturing a display substrate using the photoresist composition |
| US9411229B2 (en) * | 2011-06-20 | 2016-08-09 | Nippon Kayaku Kabushiki Kaisha | Negative photosensitive resin composition and cured product of same |
| JP2013130816A (en) * | 2011-12-22 | 2013-07-04 | Nippon Zeon Co Ltd | Resin composition for permanent film and electronic component |
| CN105814488B (en) * | 2013-12-11 | 2019-11-05 | 富士胶片株式会社 | Photosensitive polymer combination, the manufacturing method of cured film, cured film, liquid crystal display device and organic EL display device |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH05297582A (en) * | 1992-04-23 | 1993-11-12 | Fuji Photo Film Co Ltd | Positive photoresist composition |
| JPH08301990A (en) * | 1995-05-09 | 1996-11-19 | Nippon Kayaku Co Ltd | Resin composition, resist ink composition, and cured product thereof |
| JP3901266B2 (en) * | 1996-11-15 | 2007-04-04 | 東京応化工業株式会社 | Photosensitive resin composition |
| JP3873263B2 (en) * | 1997-09-22 | 2007-01-24 | Ｊｓｒ株式会社 | Radiation-sensitive resin composition, protective film, interlayer insulating film, and method for forming these films |
| ATE366952T1 (en) * | 1999-06-01 | 2007-08-15 | Toray Industries | POSITIVE WORKING LIGHT SENSITIVE POLYIMIDE PRECURSOR COMPOSITION |
| JP4221819B2 (en) * | 1999-06-01 | 2009-02-12 | 東レ株式会社 | Photosensitive resin precursor composition |
| JP2000347397A (en) * | 1999-06-04 | 2000-12-15 | Jsr Corp | Radiation sensitive resin composition and its use for interlayer dielectric |
| JP2002116536A (en) * | 2000-10-06 | 2002-04-19 | Jsr Corp | Radiation sensitive resin composition, its cured body and element |
| JP2003029407A (en) * | 2001-05-07 | 2003-01-29 | Sumitomo Bakelite Co Ltd | Positive photosensitive resin composition and semiconductor device |
| WO2003029898A1 (en) | 2001-09-27 | 2003-04-10 | Clariant International Ltd. | Photosensitive resin composition |
-
2003
- 2003-06-26 JP JP2003182087A patent/JP4099114B2/en not_active Expired - Fee Related
-
2004
- 2004-06-17 KR KR1020057024971A patent/KR100983210B1/en not_active IP Right Cessation
- 2004-06-17 CN CNB2004800169298A patent/CN100547485C/en not_active Expired - Fee Related
- 2004-06-17 WO PCT/JP2004/008531 patent/WO2005001575A1/en active Application Filing
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105988288A (en) * | 2015-03-17 | 2016-10-05 | 东友精细化工有限公司 | Photosensitive resin composition, photocuring pattern and pattern display device |
| CN105988288B (en) * | 2015-03-17 | 2021-05-28 | 东友精细化工有限公司 | Photosensitive resin composition, photocured pattern and image display device |
Also Published As
| Publication number | Publication date |
|---|---|
| TWI332121B (en) | 2010-10-21 |
| WO2005001575A1 (en) | 2005-01-06 |
| KR100983210B1 (en) | 2010-09-20 |
| TW200504461A (en) | 2005-02-01 |
| JP2005017666A (en) | 2005-01-20 |
| KR20060027817A (en) | 2006-03-28 |
| CN1806206A (en) | 2006-07-19 |
| JP4099114B2 (en) | 2008-06-11 |
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