JP6913679B2 - 感光性樹脂組成物及びそれより調製される硬化膜 - Google Patents
感光性樹脂組成物及びそれより調製される硬化膜 Download PDFInfo
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- JP6913679B2 JP6913679B2 JP2018518606A JP2018518606A JP6913679B2 JP 6913679 B2 JP6913679 B2 JP 6913679B2 JP 2018518606 A JP2018518606 A JP 2018518606A JP 2018518606 A JP2018518606 A JP 2018518606A JP 6913679 B2 JP6913679 B2 JP 6913679B2
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- siloxane polymer
- photosensitive resin
- resin composition
- silicon
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- 239000011342 resin composition Substances 0.000 title claims description 50
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 89
- 229920000642 polymer Polymers 0.000 claims description 79
- -1 silane compound Chemical class 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 43
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 229910000077 silane Inorganic materials 0.000 claims description 37
- 239000004593 Epoxy Substances 0.000 claims description 29
- 125000001153 fluoro group Chemical group F* 0.000 claims description 29
- 239000002904 solvent Substances 0.000 claims description 28
- 238000000034 method Methods 0.000 claims description 27
- 229910052710 silicon Inorganic materials 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 22
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 18
- 238000001312 dry etching Methods 0.000 claims description 17
- 239000010703 silicon Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 8
- 150000002430 hydrocarbons Chemical class 0.000 claims description 7
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000005842 heteroatom Chemical group 0.000 claims description 3
- 239000010408 film Substances 0.000 description 85
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 39
- 230000015572 biosynthetic process Effects 0.000 description 36
- 238000003786 synthesis reaction Methods 0.000 description 36
- 239000000126 substance Substances 0.000 description 27
- 239000000243 solution Substances 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 18
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 16
- 239000004094 surface-active agent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 238000011161 development Methods 0.000 description 11
- 230000018109 developmental process Effects 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 10
- 238000000576 coating method Methods 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 150000005215 alkyl ethers Chemical class 0.000 description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 230000035945 sensitivity Effects 0.000 description 7
- 150000004756 silanes Chemical class 0.000 description 7
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000012528 membrane Substances 0.000 description 6
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000014759 maintenance of location Effects 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 238000002834 transmittance Methods 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003513 alkali Substances 0.000 description 4
- 230000001588 bifunctional effect Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000001029 thermal curing Methods 0.000 description 4
- HTQNYBBTZSBWKL-UHFFFAOYSA-N 2,3,4-trihydroxbenzophenone Chemical compound OC1=C(O)C(O)=CC=C1C(=O)C1=CC=CC=C1 HTQNYBBTZSBWKL-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
- 229910052753 mercury Inorganic materials 0.000 description 3
- BOVWGKNFLVZRDU-UHFFFAOYSA-N triethoxy(trifluoromethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)F BOVWGKNFLVZRDU-UHFFFAOYSA-N 0.000 description 3
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 3
- ORVBHOQTQDOUIW-UHFFFAOYSA-N trimethoxy(trifluoromethyl)silane Chemical compound CO[Si](OC)(OC)C(F)(F)F ORVBHOQTQDOUIW-UHFFFAOYSA-N 0.000 description 3
- QYGBYAQGBVHMDD-XQRVVYSFSA-N (z)-2-cyano-3-thiophen-2-ylprop-2-enoic acid Chemical compound OC(=O)C(\C#N)=C/C1=CC=CS1 QYGBYAQGBVHMDD-XQRVVYSFSA-N 0.000 description 2
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- CPEXFJVZFNYXGU-UHFFFAOYSA-N 2,4,6-trihydroxybenzophenone Chemical compound OC1=CC(O)=CC(O)=C1C(=O)C1=CC=CC=C1 CPEXFJVZFNYXGU-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
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- VATRWWPJWVCZTA-UHFFFAOYSA-N 3-oxo-n-[2-(trifluoromethyl)phenyl]butanamide Chemical compound CC(=O)CC(=O)NC1=CC=CC=C1C(F)(F)F VATRWWPJWVCZTA-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 2
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 229910052581 Si3N4 Inorganic materials 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- YLDKQPMORVEBRU-UHFFFAOYSA-N diphenoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)OC1=CC=CC=C1 YLDKQPMORVEBRU-UHFFFAOYSA-N 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
- MYEJNNDSIXAGNK-UHFFFAOYSA-N ethyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](CC)(OC(C)C)OC(C)C MYEJNNDSIXAGNK-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
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- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
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- 230000035484 reaction time Effects 0.000 description 2
- 125000005372 silanol group Chemical group 0.000 description 2
- HQVNEWCFYHHQES-UHFFFAOYSA-N silicon nitride Chemical compound N12[Si]34N5[Si]62N3[Si]51N64 HQVNEWCFYHHQES-UHFFFAOYSA-N 0.000 description 2
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- 230000008961 swelling Effects 0.000 description 2
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 2
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- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 2
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 2
- XAOGTWQKPPOJOP-UHFFFAOYSA-N triethoxy(1,1,2,2,2-pentafluoroethyl)silane Chemical compound CCO[Si](OCC)(OCC)C(F)(F)C(F)(F)F XAOGTWQKPPOJOP-UHFFFAOYSA-N 0.000 description 2
- NOBMQPILAFKJLD-UHFFFAOYSA-N triethoxy(2,2,2-trifluoroethyl)silane Chemical compound CCO[Si](CC(F)(F)F)(OCC)OCC NOBMQPILAFKJLD-UHFFFAOYSA-N 0.000 description 2
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- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
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- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 2
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- WVJRCSCNOMJNLP-UHFFFAOYSA-N (2-hydroxy-5-trimethoxysilylpentyl) 4-hydroxybenzoate Chemical compound CO[Si](OC)(OC)CCCC(O)COC(=O)C1=CC=C(O)C=C1 WVJRCSCNOMJNLP-UHFFFAOYSA-N 0.000 description 1
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- ZGKWWOVOEOZQPP-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methoxymethoxy-dimethoxy-propylsilane Chemical compound C(C)C1(COC1)COCO[Si](OC)(OC)CCC ZGKWWOVOEOZQPP-UHFFFAOYSA-N 0.000 description 1
- HWZREQONUGCFIT-UHFFFAOYSA-N (3-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound OC1=CC=CC(C(=O)C=2C(=C(O)C(O)=CC=2)O)=C1 HWZREQONUGCFIT-UHFFFAOYSA-N 0.000 description 1
- ZRDYULMDEGRWRC-UHFFFAOYSA-N (4-hydroxyphenyl)-(2,3,4-trihydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1O ZRDYULMDEGRWRC-UHFFFAOYSA-N 0.000 description 1
- 229920003122 (meth)acrylate-based copolymer Polymers 0.000 description 1
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical compound C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 1
- 229940105324 1,2-naphthoquinone Drugs 0.000 description 1
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Classifications
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- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
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- G03F7/20—Exposure; Apparatus therefor
- G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
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- G03F7/32—Liquid compositions therefor, e.g. developers
- G03F7/322—Aqueous alkaline compositions
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- G03F7/26—Processing photosensitive materials; Apparatus therefor
- G03F7/40—Treatment after imagewise removal, e.g. baking
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
- H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
- H01L21/04—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer
- H01L21/18—Manufacture or treatment of semiconductor devices or of parts thereof the devices having potential barriers, e.g. a PN junction, depletion layer or carrier concentration layer the devices having semiconductor bodies comprising elements of Group IV of the Periodic Table or AIIIBV compounds with or without impurities, e.g. doping materials
- H01L21/30—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26
- H01L21/31—Treatment of semiconductor bodies using processes or apparatus not provided for in groups H01L21/20 - H01L21/26 to form insulating layers thereon, e.g. for masking or by using photolithographic techniques; After treatment of these layers; Selection of materials for these layers
- H01L21/3105—After-treatment
- H01L21/31051—Planarisation of the insulating layers
- H01L21/31053—Planarisation of the insulating layers involving a dielectric removal step
- H01L21/31055—Planarisation of the insulating layers involving a dielectric removal step the removal being a chemical etching step, e.g. dry etching
- H01L21/31056—Planarisation of the insulating layers involving a dielectric removal step the removal being a chemical etching step, e.g. dry etching the removal being a selective chemical etching step, e.g. selective dry etching through a mask
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- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers
- H01L27/12—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body
- H01L27/1214—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs
- H01L27/1248—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers the substrate being other than a semiconductor body, e.g. an insulating body comprising a plurality of TFTs formed on a non-semiconducting substrate, e.g. driving circuits for AMLCDs with a particular composition or shape of the interlayer dielectric specially adapted to the circuit arrangement
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- H01L27/00—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate
- H01L27/02—Devices consisting of a plurality of semiconductor or other solid-state components formed in or on a common substrate including semiconductor components specially adapted for rectifying, oscillating, amplifying or switching and having potential barriers; including integrated passive circuit elements having potential barriers
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Description
(A)フッ素原子を含むシロキサンポリマーと、
(B)1,2−キノンジアジド化合物と、
(C)エポキシ化合物と、を含む、感光性樹脂組成物が提供される。
このシロキサンポリマーは、フッ素原子を含むシラン化合物及び/またはその加水分解物の縮合物を含む。このシロキサンポリマーは、フッ素原子を含む限り特に限定されない。フッ素原子はシロキサンポリマーのケイ素原子と結合してもよく、またはケイ素原子と結合した有機基を構成する原子として含まれてもよい。この有機基は、例えば、置換された、または置換されていないフッ素化された炭化水素基を含むことができる。
R1は、フッ素原子またはフッ素原子を含む一価の炭化水素であり、R1が一価の炭化水素である場合、水素原子は部分的または全体的に置換されてもよく、複数のR1が同じ分子内に存在する場合、各R1は互いに同一でも異なってもよく、
R2は、水素、1〜6個の炭素原子を有するアルキル、2〜6個の炭素原子を有するアシル、または6〜15個の炭素原子を有するアリールであり、複数のR2が同じ分子内に存在する場合、各R2は互いに同一でも異なってもよく、R2がアルキル、アシル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、
nは、1〜3の整数である。
R3は、1〜12個の炭素原子を有するアルキル、2〜10個の炭素原子を有するアルケニル、または6〜15個の炭素有するアリールであり、複数のR3が同じ分子内に存在する場合、各R3は、互いに同一でも異なってもよく、R3がアルキル、アルケニル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、R3はヘテロ原子を含む構造単位を含んでもよく、
R4は、水素、1〜6個の炭素原子を有するアルキル、2〜6個の炭素原子を有するアシル、または6〜15個の炭素原子を有するアリールであり、複数のR4が同じ分子内に存在する場合、各R4は互いに同一でも異なってもよく、R4がアルキル、アシル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、
nは、0〜3の整数である。
本発明の感光性樹脂組成物は、1,2−キノンジアジド化合物(B)を含む。
本発明の感光性樹脂組成物において、エポキシ化合物は、シロキサン結合剤の内部密度を大きくするためシロキサンポリマーと共に使用され、それにより組成物から調製される硬化膜の化学耐性を改善することができる。
本発明の感光性樹脂組成物は、上記成分を溶媒が混合される液体組成物として調製され得る。本溶剤は、例えば有機溶剤であってもよい。
本発明の感光性樹脂組成物は、その被覆性を高めるため界面活性剤をさらに含み得る。
以下、本発明を以下の実施例を参照してより詳細に記載する。しかしながら、これらの実施例は本発明を説明するために提供されるに過ぎず、本発明の範囲はこれらに限定されない。
還流冷却器を備えた反応器に40重量%のフェニルトリメトキシシラン、15重量%のメチルトリメトキシシラン、20重量%のテトラエトキシシラン、及び20重量%の純水を添加し、次いで5重量%の酢酸プロピレングリコールモノメチルエーテル(PGMEA)が添加され、続いて、0.1重量%のシュウ酸触媒存在下で混合物を、7時間、還流と撹拌し、その後冷却した。その後、固体分が40重量%であるように、反応生成物がPGMEAで希釈された。約5,000〜10,000Daの重量平均分子量を有するシロキサンポリマーが合成された。
還流冷却器を備えた反応器へ20重量%のフェニルトリメトキシシラン、30重量%のメチルトリメトキシシラン、20重量%のテトラエトキシシラン及び15重量%の純水が添加され、次いで、15重量%のPGMEAが添加され、その後、混合物を0.1重量%のシュウ酸触媒存在下で、6時間還流、撹拌し、冷却した。その後、反応生成物は、固体分が30重量%であるようにPGMEAで希釈された。約8,000〜13,000Daの重量平均分子量を有するシロキサンポリマーが合成された。
還流冷却器を備えた反応器に20重量%のフェニルトリメトキシシラン、30重量%のメチルトリメトキシシラン、20重量%のテトラエトキシシラン及び15重量%の純水が添加され、次いで15重量%のPGMEAが添加され、続いて0.1重量%のシュウ酸触媒存在下、5時間、混合物を還流、撹拌し、冷却した。その後、固体分が30重量%となるように反応生成物はPGMEAで希釈された。約9,000〜15,000Daの重量平均分子量を有するシロキサンポリマーが合成された。
還流冷却器を備えた反応器に30重量%のフェニルトリメトキシシラン、15重量%のメチルトリメトキシシラン、20重量%のテトラエトキシシラン及び10重量%のトリフルオロプロピルトリメトキシシラン及び20重量%の純水が添加され、次いで5重量%のPGMEAが添加され、続いて0.1重量%のシュウ酸触媒存在下7時間、混合物を還流、撹拌し、冷却した。その後、固体分が40重量%となるように反応生成物はPGMEAで希釈された。約5,000〜10,000Daの重量平均分子量を有するフッ素含有シロキサンポリマーが合成された。
冷却器を備えた3頚フラスコを自動温度調節器のついた撹拌装置上に置いた。100重量部のメタクリル酸グリシジル(100モル%)からなるモノマー、10重量部の2,2’−アゾビス(2−メチルブチロニトリル)、及び100重量部のPGMEAがフラスコに添加され、フラスコは窒素で置換された。フラスコは、ゆっくりと混合物を撹拌しながら80℃まで加熱され、温度を5時間、維持し約6,000〜10,000Daの重量平均分子量を有するエポキシ化合物を得た。次いで、PGMEAが添加され、固体分を20重量%に調整した。
以下の例の感光性樹脂組成物と比較例が上記合成例で得られた化合物を使用して合成された。
−1,2−キノンジアジド化合物:MIPHOTO TPA−517、Miwon Commercial Co.,Ltd.
−溶媒:PGMEA、Chemtronics Co.,Ltd.
γ−ブチロラクトン(GBL)、BASF
−界面活性剤:シリコン界面活性剤、FZ−2122、Dow Corning Toray Co., Ltd.
−フッ素界面活性剤、TF−1831、DIC
−フッ素界面活性剤、RS−932、DIC
−フッ素界面活性剤、TF−1807、DIC
実施例及び比較例で得られた各組成物が、スピンコーティングにより窒化ケイ素基板上に被覆された。被覆された基板は、110℃に保たれたホットプレート上で90秒プレベークを受け、乾燥膜を形成した。乾燥膜は、2μmから25μmの範囲の大きさの四角い孔からなるパターンを有するマスクを通して露光された。露光はアライナ(機種名:MA6)を使い、一定時間365nmの波長に基づき0から200mJ/cm2の露光量で露光を行った。アライナは200nm〜450nmの波長を有する光を発光した。乾燥膜は、23℃で、2.38重量%水酸化テトラメチルアンモニウムの水性現像液を、ノズルを通して噴霧することにより現像された。露光された膜は、次に熱対流炉において230℃で30分間加熱され、厚さ3.0μmを有する硬化膜を得た。
実施例と比較例で得られた各組成物が、スピンコーティングにより窒化ケイ素基板上に被覆された。被覆された基板は110℃に保たれたホットプレート上で90秒間プレベークされ、2.1μmの厚さを有する乾燥膜を形成した。乾燥膜は、パターンを有するマスクを通し、アライナ(機種名MA6)を使用して、一定時間365nmの波長に基づき約100mJ/cm2の露光エネルギーで、露光された。アライナは200nm〜450nmの波長を有する光を発光した。乾燥膜は、23℃で、2.38重量%水酸化テトラメチルアンモニウムの水性現像液を、ノズルを通して噴霧することにより現像された。そのように露光された膜は、次に熱対流炉で、230℃で30分間加熱され、厚さ2μmを有する硬化膜を得た。
◎:矩形の形状が明確であり、底部の広がりは観察されなかった。
○:矩形の形状が明確であるが、表面はなめらかではない。
△:矩形の形状が明確であるが、表面はなめらかではない、あるいは斑点状の残存膜が残っている。
X:矩形の形状が明確ではない、または硬化膜が現像されなかった。
プレベーク、マスクを通した露光、現像及び熱的硬化等の実験例2と同じ手順が、実施例、比較例で得られた各組成物について繰り返され、硬化膜を調製した。膜保持率が非接触型厚さ測定装置(SNU Precision)を使用してプレベーク直後の硬化膜の厚さと比較した最終硬化膜の厚さのパーセントを計算することにより得られた。
実施例と比較例で得られた各組成物は、スピンコーティング法によりガラス基板上に被覆された。プレベーク、マスクを通した露光、現像及び熱的硬化等の実験例2で述べられたものと同じ手順が繰り返され、約2μmの厚さを有する硬化膜を調製した。400〜800nmの範囲の波長での硬化膜の光透過率が紫外/可視分光器を使用して測定された。
実験例2で述べられたのと同一の手順に従い実施例と比較例で得られた各組成物を使い、プレベーク、マスクを通した露光、現像及び熱的硬化を経て、硬化膜が得られた。硬化膜のフッ素イオン強度がSIMS分析により測定された。SIMS分析器(TOF SIMS5、ION TOF Co.,Ltd.製造)を使用して、硬化膜の表面から約3000Åの深さまでのフッ素含量が測定された。この場合、1000以上のフッ素イオン強度が撥水性を与えられる良好な程度であると評価され得る。
実験例2で述べられたものと同一の手順に従い実施例と比較例で得られた各組成物を使用してプレベーク、マスクを通した露光、現像及び熱的硬化を経て硬化膜が得られた。硬化膜の表面はO2/SF6ガス(分圧比2.7:1)を使い、100秒間、ICP(活性源)を使いドライエッチングにより約3000Åまでエッチングされた。ドライエッチング後の硬化膜の厚さ(T1)は非接触型厚さ測定装置(SNU Precision)を使い測定された。再処理化学物質(製品名:LT−360)が定温の浴に導入され、温度が50℃に維持された。硬化膜は5分間、浴に浸漬され、再処理化学物質が空気により除去された。次いで、硬化膜の厚さ(T2)が測定された。
実験例6に述べられたものと同一の手順により実施例と比較例で得られた各組成物を使用して硬化膜が得られ、ドライエッチングが行われた。ドライエッチング後に超純水に関して硬化膜の表面の接触角が、接触角測定装置を使用して測定された。一般に、硬化膜の表面は、ドライエッチングによりエッチングされる後に非均一となり得、接触角は、ドライエッチング前の表面と比べて小さくなる。ドライエッチング後に接触角が大きくなる場合、硬化膜にフッ素成分が均一に分散し、良好な撥水性が得られると考えられ得る。ドライエッチング後に接触角が80°以上である場合、表面の撥水性は良好であり、化学物質による膨潤の程度は最小になり、化学耐性は良好と評価され得る。
Claims (9)
- 感光性樹脂組成物であって、
(A)フッ素原子を含むシロキサンポリマーと、
(B)1,2−キノンジアジド化合物と、
(C)エポキシ化合物と、を含み、
前記フッ素原子を含むシロキサンポリマー(A)は、溶媒を除く前記組成物の固体分の全重量を基準として、50〜95重量%の量で含まれ、
前記エポキシ化合物(C)は、溶媒を除く固体分を基準として100重量部の前記シロキサンポリマー(A)に基づき5〜25重量部の量で感光性樹脂組成物に含まれる、感光性樹脂組成物。 - 前記エポキシ化合物(C)がカルボキシル基を含まない、請求項1に記載の感光性樹脂組成物。
- 前記フッ素原子を含むシロキサンポリマー(A)が、以下の式1で表されるシラン化合物に由来する少なくとも1つの構造単位を含み、
R1は、フッ素原子またはフッ素原子を含む一価の炭化水素であり、R1が前記一価の炭化水素である場合、水素原子は部分的または全体的に置換されてもよく、複数のR1が同じ分子内に存在する場合、各R1は互いに同一でも異なってもよく、
R2は、水素、1〜6個の炭素原子を有するアルキル、2〜6個の炭素原子を有するアシル、または6〜15個の炭素原子を有するアリールであり、複数のR2が同じ分子内に存在する場合、各R2は互いに同一でも異なってもよく、R2がアルキル、アシル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、
nは、1〜3の整数である、請求項1または2に記載の感光性樹脂組成物。 - 前記フッ素原子を含むシロキサンポリマー(A)が、以下の式2で表されるシラン化合物に由来する少なくとも1つの構造単位をさらに含み、
R3は、1〜12個の炭素原子を有するアルキル、2〜10個の炭素原子を有するアルケニル、または6〜15個の炭素原子を有するアリールであり、複数のR3が同じ分子内に存在する場合、各R3は互いに同一でも異なってもよく、R3がアルキル、アルケニル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、R3はヘテロ原子を含む構造単位を含んでもよく、
R4は、水素、1〜6個の炭素原子を有するアルキル、2〜6個の炭素原子を有するアシル、または6〜15個の炭素原子を有するアリールであり、複数のR4が同じ分子内に存在する場合、各R4は互いに同一でも異なってもよく、R4がアルキル、アシル、またはアリールである場合、水素原子は部分的または全体的に置換されてもよく、
nは、0〜3の整数である、請求項3に記載の感光性樹脂組成物。 - 前記フッ素原子を含むシロキサンポリマー(A)が、nが0である式2のシラン化合物に由来する構造単位を含む、請求項4に記載の感光性樹脂組成物。
- 前記フッ素原子を含むシロキサンポリマー(A)が、Si原子モル数を基準として前記シロキサンポリマー中に前記フッ素含有構造単位の1〜30%の含量(モル%)の前記フッ素原子を含む、請求項1に記載の感光性樹脂組成物。
- パターンを形成する方法であって、
請求項1に記載の感光性樹脂組成物を使用して基板の表面にケイ素含有膜を形成することと、
光を使用して前記ケイ素含有膜をパターン形成することと、
前記パターン形成されたケイ素含有膜及び前記基板をドライエッチングして、前記基板にパターンを形成することと、を含む、方法。 - 請求項1に記載の感光性樹脂組成物を使用して基板の表面にケイ素含有膜を形成することと、
光を使用して前記ケイ素含有膜をパターン形成することと、
前記パターン形成されたケイ素含有膜及び前記基板をドライエッチングして、前記基板にパターンを形成することと、を含む、ケイ素含有硬化膜を形成する方法。 - 前記ケイ素含有硬化膜が、ドライエッチング後に80°以上の接触角を有する、請求項8に記載のケイ素含有硬化膜を形成する方法。
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PCT/KR2016/010551 WO2017078267A1 (en) | 2015-11-06 | 2016-09-22 | Photosensitive resin composition and cured film prepared therefrom |
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JPH01142721A (ja) | 1987-11-30 | 1989-06-05 | Fujitsu Ltd | ポジ型感光性パターン形成材料およびパターン形成方法 |
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EP1662322B1 (en) | 2004-11-26 | 2017-01-11 | Toray Industries, Inc. | Positive type photo-sensitive siloxane composition, curing film formed by the composition and device with the curing film |
JP4687315B2 (ja) * | 2005-08-04 | 2011-05-25 | 東レ株式会社 | 感光性樹脂組成物、それから形成された硬化膜、および硬化膜を有する素子 |
JP5764863B2 (ja) | 2005-10-28 | 2015-08-19 | 東レ株式会社 | 固体撮像素子 |
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US20120237873A1 (en) * | 2009-12-20 | 2012-09-20 | Toray Industries Inc. | Positive photosensitive resin composition, cured film formed from the same, and device having cured film |
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US8993214B2 (en) * | 2011-05-20 | 2015-03-31 | Az Electronic Materials Usa Corp. | Positive photosensitive siloxane composition |
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US10591818B2 (en) * | 2016-07-28 | 2020-03-17 | Promerus, Llc | Nadic anhydride polymers and photosensitive compositions derived therefrom |
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KR20170053442A (ko) | 2017-05-16 |
CN108139671A (zh) | 2018-06-08 |
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