CN101013263B - Photosensitive resin composition suitable for irrational and slit mold coating method - Google Patents
Photosensitive resin composition suitable for irrational and slit mold coating method Download PDFInfo
- Publication number
- CN101013263B CN101013263B CN200710001223XA CN200710001223A CN101013263B CN 101013263 B CN101013263 B CN 101013263B CN 200710001223X A CN200710001223X A CN 200710001223XA CN 200710001223 A CN200710001223 A CN 200710001223A CN 101013263 B CN101013263 B CN 101013263B
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- CN
- China
- Prior art keywords
- photosensitive resin
- resin composition
- phenolics
- methyl
- emulsion
- 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
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- 239000011342 resin composition Substances 0.000 title claims abstract description 41
- 238000000576 coating method Methods 0.000 title abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 33
- 150000002148 esters Chemical class 0.000 claims abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 235000013824 polyphenols Nutrition 0.000 claims description 31
- 239000000839 emulsion Substances 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 17
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 238000007607 die coating method Methods 0.000 claims description 13
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 claims description 12
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 239000011347 resin Substances 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 31
- 239000011248 coating agent Substances 0.000 abstract description 10
- 235000014113 dietary fatty acids Nutrition 0.000 abstract description 7
- 229930195729 fatty acid Natural products 0.000 abstract description 7
- 239000000194 fatty acid Substances 0.000 abstract description 7
- 150000004665 fatty acids Chemical class 0.000 abstract description 7
- 239000002585 base Substances 0.000 abstract description 5
- 239000003513 alkali Substances 0.000 abstract description 4
- 239000005011 phenolic resin Substances 0.000 abstract description 2
- 230000005855 radiation Effects 0.000 abstract 2
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- -1 bisphenol-A Chemical class 0.000 description 25
- 239000010408 film Substances 0.000 description 17
- 239000007787 solid Substances 0.000 description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 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 7
- 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
- 238000006243 chemical reaction Methods 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 7
- 230000032050 esterification Effects 0.000 description 7
- 238000005886 esterification reaction Methods 0.000 description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
- KETQAJRQOHHATG-UHFFFAOYSA-N 1,2-naphthoquinone Chemical class C1=CC=C2C(=O)C(=O)C=CC2=C1 KETQAJRQOHHATG-UHFFFAOYSA-N 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 239000004793 Polystyrene Substances 0.000 description 6
- 125000001153 fluoro group Chemical class F* 0.000 description 6
- 229920002223 polystyrene Polymers 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 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
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 description 5
- 239000004973 liquid crystal related substance Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 4
- 229930185605 Bisphenol Natural products 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 230000003213 activating effect Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 4
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 4
- 238000005096 rolling process Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- JEFSTMHERNSDBC-UHFFFAOYSA-N 1,2-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC=CCC1(C)O JEFSTMHERNSDBC-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- IXQGCWUGDFDQMF-UHFFFAOYSA-N 2-Ethylphenol Chemical compound CCC1=CC=CC=C1O IXQGCWUGDFDQMF-UHFFFAOYSA-N 0.000 description 3
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229930192627 Naphthoquinone Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
- 150000002791 naphthoquinones Chemical class 0.000 description 3
- 239000001149 (9Z,12Z)-octadeca-9,12-dienoate Substances 0.000 description 2
- 150000000181 1,2-naphthoquinones Chemical class 0.000 description 2
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- JWAZRIHNYRIHIV-UHFFFAOYSA-N 2-naphthol Chemical compound C1=CC=CC2=CC(O)=CC=C21 JWAZRIHNYRIHIV-UHFFFAOYSA-N 0.000 description 2
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 2
- LPCJHUPMQKSPDC-UHFFFAOYSA-N 3,5-diethylphenol Chemical compound CCC1=CC(O)=CC(CC)=C1 LPCJHUPMQKSPDC-UHFFFAOYSA-N 0.000 description 2
- TUAMRELNJMMDMT-UHFFFAOYSA-N 3,5-xylenol Chemical compound CC1=CC(C)=CC(O)=C1 TUAMRELNJMMDMT-UHFFFAOYSA-N 0.000 description 2
- HMNKTRSOROOSPP-UHFFFAOYSA-N 3-Ethylphenol Chemical compound CCC1=CC=CC(O)=C1 HMNKTRSOROOSPP-UHFFFAOYSA-N 0.000 description 2
- NPFYZDNDJHZQKY-UHFFFAOYSA-N 4-Hydroxybenzophenone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=CC=C1 NPFYZDNDJHZQKY-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- 206010034972 Photosensitivity reaction Diseases 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 150000004054 benzoquinones Chemical class 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 150000001896 cresols Chemical class 0.000 description 2
- 238000007766 curtain coating Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- MMXKVMNBHPAILY-UHFFFAOYSA-N ethyl laurate Chemical compound CCCCCCCCCCCC(=O)OCC MMXKVMNBHPAILY-UHFFFAOYSA-N 0.000 description 2
- MMKRHZKQPFCLLS-UHFFFAOYSA-N ethyl myristate Chemical compound CCCCCCCCCCCCCC(=O)OCC MMKRHZKQPFCLLS-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000001459 lithography Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 2
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 description 2
- ZAZKJZBWRNNLDS-UHFFFAOYSA-N methyl tetradecanoate Chemical compound CCCCCCCCCCCCCC(=O)OC ZAZKJZBWRNNLDS-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000036211 photosensitivity Effects 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229960004063 propylene glycol Drugs 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- OKJFKPFBSPZTAH-UHFFFAOYSA-N (2,4-dihydroxyphenyl)-(4-hydroxyphenyl)methanone Chemical compound C1=CC(O)=CC=C1C(=O)C1=CC=C(O)C=C1O OKJFKPFBSPZTAH-UHFFFAOYSA-N 0.000 description 1
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- WTTJVINHCBCLGX-UHFFFAOYSA-N (9trans,12cis)-methyl linoleate Natural products CCCCCC=CCC=CCCCCCCCC(=O)OC WTTJVINHCBCLGX-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
- 150000005206 1,2-dihydroxybenzenes Chemical class 0.000 description 1
- PCNMALATRPXTKX-UHFFFAOYSA-N 1,4-dimethylcyclohexa-2,4-dien-1-ol Chemical compound CC1=CCC(C)(O)C=C1 PCNMALATRPXTKX-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical class CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- DVWSXZIHSUZZKJ-UHFFFAOYSA-N 18:3n-3 Natural products CCC=CCC=CCC=CCCCCCCCC(=O)OC DVWSXZIHSUZZKJ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZCONCJFBSHTFFD-UHFFFAOYSA-N 2,3,5-triethylphenol Chemical compound CCC1=CC(O)=C(CC)C(CC)=C1 ZCONCJFBSHTFFD-UHFFFAOYSA-N 0.000 description 1
- RLEWTHFVGOXXTN-UHFFFAOYSA-N 2,3-diethylphenol Chemical compound CCC1=CC=CC(O)=C1CC RLEWTHFVGOXXTN-UHFFFAOYSA-N 0.000 description 1
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 1
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- BGYYQQXEPNESCZ-UHFFFAOYSA-N 2-[(2-hydroxy-3,5-dimethylphenyl)methyl]benzene-1,3-diol Chemical compound C1=C(C)C=C(C(=C1CC1=C(C=CC=C1O)O)O)C BGYYQQXEPNESCZ-UHFFFAOYSA-N 0.000 description 1
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- ZTMADXFOCUXMJE-UHFFFAOYSA-N 2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC=C1O ZTMADXFOCUXMJE-UHFFFAOYSA-N 0.000 description 1
- LNJCGNRKWOHFFV-UHFFFAOYSA-N 3-(2-hydroxyethylsulfanyl)propanenitrile Chemical compound OCCSCCC#N LNJCGNRKWOHFFV-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
- CYEKUDPFXBLGHH-UHFFFAOYSA-N 3-tert-Butylphenol Chemical compound CC(C)(C)C1=CC=CC(O)=C1 CYEKUDPFXBLGHH-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical class O=C1CCCO1 YEJRWHAVMIAJKC-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
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 1
- PHZREHARUPHHCU-UHFFFAOYSA-N 4-methylbenzene-1,2,3-triol Chemical compound CC1=CC=C(O)C(O)=C1O PHZREHARUPHHCU-UHFFFAOYSA-N 0.000 description 1
- ZBCATMYQYDCTIZ-UHFFFAOYSA-N 4-methylcatechol Chemical compound CC1=CC=C(O)C(O)=C1 ZBCATMYQYDCTIZ-UHFFFAOYSA-N 0.000 description 1
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 description 1
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- 235000001759 Citrus maxima Nutrition 0.000 description 1
- 244000276331 Citrus maxima Species 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
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- PKIXXJPMNDDDOS-UHFFFAOYSA-N Methyl linoleate Natural products CCCCC=CCCC=CCCCCCCCC(=O)OC PKIXXJPMNDDDOS-UHFFFAOYSA-N 0.000 description 1
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- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 description 1
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- TZRXHJWUDPFEEY-UHFFFAOYSA-N Pentaerythritol Tetranitrate Chemical compound [O-][N+](=O)OCC(CO[N+]([O-])=O)(CO[N+]([O-])=O)CO[N+]([O-])=O TZRXHJWUDPFEEY-UHFFFAOYSA-N 0.000 description 1
- IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- RIHODQKIOXUKLF-UHFFFAOYSA-N anisole;phenol Chemical class OC1=CC=CC=C1.COC1=CC=CC=C1 RIHODQKIOXUKLF-UHFFFAOYSA-N 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 229950011260 betanaphthol Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 1
- 229960001777 castor oil Drugs 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- OOOYJJANGWVIRW-UHFFFAOYSA-N chlorobenzene;phenol Chemical class OC1=CC=CC=C1.ClC1=CC=CC=C1 OOOYJJANGWVIRW-UHFFFAOYSA-N 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000007323 disproportionation reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- QYDYPVFESGNLHU-UHFFFAOYSA-N elaidic acid methyl ester Natural products CCCCCCCCC=CCCCCCCCC(=O)OC QYDYPVFESGNLHU-UHFFFAOYSA-N 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- CAMHHLOGFDZBBG-UHFFFAOYSA-N epoxidized methyl oleate Natural products CCCCCCCCC1OC1CCCCCCCC(=O)OC CAMHHLOGFDZBBG-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940031016 ethyl linoleate Drugs 0.000 description 1
- FMMOOAYVCKXGMF-MURFETPASA-N ethyl linoleate Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(=O)OCC FMMOOAYVCKXGMF-MURFETPASA-N 0.000 description 1
- 229940090028 ethyl linolenate Drugs 0.000 description 1
- JYYFMIOPGOFNPK-AGRJPVHOSA-N ethyl linolenate Chemical compound CCOC(=O)CCCCCCC\C=C/C\C=C/C\C=C/CC JYYFMIOPGOFNPK-AGRJPVHOSA-N 0.000 description 1
- JYYFMIOPGOFNPK-UHFFFAOYSA-N ethyl linolenate Natural products CCOC(=O)CCCCCCCC=CCC=CCC=CCC JYYFMIOPGOFNPK-UHFFFAOYSA-N 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- FMMOOAYVCKXGMF-UHFFFAOYSA-N linoleic acid ethyl ester Natural products CCCCCC=CCC=CCCCCCCCC(=O)OCC FMMOOAYVCKXGMF-UHFFFAOYSA-N 0.000 description 1
- 150000002672 m-cresols Chemical class 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- DVWSXZIHSUZZKJ-YSTUJMKBSA-N methyl linolenate Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)OC DVWSXZIHSUZZKJ-YSTUJMKBSA-N 0.000 description 1
- QYDYPVFESGNLHU-KHPPLWFESA-N methyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC QYDYPVFESGNLHU-KHPPLWFESA-N 0.000 description 1
- 229940073769 methyl oleate Drugs 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- KOXNXRMZJZVCJA-UHFFFAOYSA-N phenol 1,2,3-trimethylbenzene Chemical class C1(=CC=CC=C1)O.CC=1C(=C(C=CC1)C)C KOXNXRMZJZVCJA-UHFFFAOYSA-N 0.000 description 1
- MOZWGCRWGKSWAJ-UHFFFAOYSA-N phenol;1,2-xylene Chemical class OC1=CC=CC=C1.CC1=CC=CC=C1C MOZWGCRWGKSWAJ-UHFFFAOYSA-N 0.000 description 1
- LXXWKCAIQDMAJD-UHFFFAOYSA-N phenol;toluene Chemical class CC1=CC=CC=C1.OC1=CC=CC=C1 LXXWKCAIQDMAJD-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- CIBMHJPPKCXONB-UHFFFAOYSA-N propane-2,2-diol Chemical compound CC(C)(O)O CIBMHJPPKCXONB-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical class C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/022—Quinonediazides
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- 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
- G03F7/022—Quinonediazides
- G03F7/023—Macromolecular quinonediazides; Macromolecular additives, e.g. binders
- G03F7/0233—Macromolecular quinonediazides; Macromolecular additives, e.g. binders characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides
- G03F7/0236—Condensation products of carbonyl compounds and phenolic compounds, e.g. novolak resins
Landscapes
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
- Non-Silver Salt Photosensitive Materials And Non-Silver Salt Photography (AREA)
Abstract
The present invention provides a radiation sensitive resin composition suitable for spinless, slit coating and having high coating film thickness uniformity. The radiation sensitive resin composition is characterized in that it includes alkali soluble formaldehyde-phenol resin, sensitizer and ester of fatty acid and lower alcohol. The invention also provides a method for manufacturing resists base plate by the composition and a manufactured resists base plate thereby.
Description
Technical field
The present invention relates to irrotationality, slit die applies and uses photosensitive resin composition; More particularly, relating to a kind of irrotationality, slit die of filming than the better resist of film thickness uniformity in the past of can forming when applying through irrotationality, slit die coating process applies and uses photosensitive resin composition.
Background technology
In the manufacturing of SIC (semiconductor integrated circuit) element, color filter, liquid crystal display cells etc., in order to carry out retrofit, adopted lithography technique in the past, developing the technology that can carry out the microfabrication of submicron degree in recent years.In this lithography technique, after forming antireflection film on the substrate, apply eurymeric or negative type photo-sensitive resin combination as required, form the photosensitivity resist film after the prebake.Then, this photosensitivity resist film is carried out for example developing behind the pattern exposure with various rays such as ultraviolet ray, far ultraviolet, electron beam, X ray, form the resist pattern.
As the coating method of photosensitive resin composition, known spin-coating method, rolling method, the flat the whole bag of tricks such as method (ラ Application De コ one ト method), curtain coating coating process, knife coating, dip coating method that are coated with.Specifically, in the manufacturing of SIC (semiconductor integrated circuit) element or liquid crystal display cells, as the material of resist film, adopt the positive type photosensitive resin combination mostly, and adopt spin-coating method mostly as coating method.In addition, in the manufacturing of liquid crystal display cells,, generally also adopt rolling method when adopting spin-coating method as coating method.
But; When adopting spin-coating method as the method that photosensitive resin composition is coated on the substrate; Drop in resist solution on the substrate along with the centrifugal force of substrate rotation after substrate peripheral direction curtain coating; Most of resist solution becomes superfluous resist solution and is dispersed by the substrate periphery and to remove, and these resist solution of removing that disperse go out of use.This spin-coating method can easily form the resist film with homogeneous film thickness, but on the other hand, and the amount of above-mentioned discarded resist is more, has the high shortcoming of cost.By contrast, rolling method be owing to can making used most of resist utilize as resist film, thereby can cost degradation, produces the shortcoming that striated or shaddock skin shape etc. apply spots but when applying photosensitive resin composition, have.For example, have in the liquid crystal display cells that the resist film of this coating spot makes, the brightness disproportionation of light occurs, cause the tendency that descends as commodity value, therefore also proposed the rolling method (patent documentation 1) of improvement in use.
In addition, for adapting to the maximization of substrate size in recent years, the slit die coating process becomes the main stream approach that replaces spin-coating method.Even under the situation of using this coating method, the composition of composition also is identical usually.For example; Make known former being generally of photosensitive resin composition that flat-panel monitor uses with phenolics and quinone two nitrine emulsion photosensitive resin composition as principal ingredient; Even forming under the situation of filming, also be to use most this composition that needs to regulate viscosity through the slit die coating process.But in general slit die coating process (for example the coating speed of photosensitive resin composition is that 100mm/ is about second), it is higher that the end of applicator surface produces the tendency that expands, and must eliminate the thicker end of film thickness, causes yield rate lower.Consider from the angle of yield-power; Apply in (for example the coating speed of photosensitive resin composition is that 150mm/ is about second) in the high-velocity scanning that further improves coating speed; This tendency further improves, and therefore need with irrotationality, slit die coating process the time, can access the very photosensitive resin composition of homogeneous film thickness.
[patent documentation 1] TOHKEMY 2000-267270 communique
Summary of the invention
The purpose of this invention is to provide a kind of photosensitive resin composition, the shortcoming of the problem before it does not have to produce in irrotationality, slit die coating process.Specifically, provide a kind of and can prevent membrane thickness unevenness when applying, apply the high photosensitive resin composition of film thickness uniformity through irrotationality, slit die coating process.
Resist is in the past formed through irrotationality, the coating of slit die coating process the time; Be considered to substrate end-face film thickness uniformity existing problems; Present inventors find, in the photosensitive resin composition of the emulsion through making the alkali soluble resin that comprises alkali-soluble phenolics etc. and naphthoquinones two triazo-compounds etc., contain fatty acid esterification and obtain specific compound in alcohol; Thereby can obtain to have the photosensitive resin composition of good coating characteristic, accomplish the present invention thus.That is, photosensitive resin composition of the present invention is characterised in that containing fatty acid and the carbon number that alkali-soluble phenolics, emulsion and carbon number are 10-20 is the ester of the alcohol of 1-5.
In addition, the manufacturing approach of resist substrate of the present invention is characterised in that and comprises through the slit die coating process above-mentioned photosensitive resin composition is coated on the substrate, and resist substrate of the present invention is characterised in that through this method manufacturing.
The photosensitive resin composition that is applicable to irrotationality, slit die coating of the application of the invention; Can form and apply more excellent in the past the filming of film thickness uniformity ratio; When making liquid crystal display cells etc. with it, can make the high-quality goods that do not have luminance brightness uneven at low cost.
Embodiment
Photosensitive resin composition of the present invention with the ester of alkali-soluble phenolics, emulsion and fatty acid and alcohol as must composition.Explanation to these each compositions is following.
Used alkali-soluble phenolics is the novolac type phenol resin that is obtained by the aldehyde condensation polymer of at least a phenols and formalin etc. in the photosensitive resin composition of the present invention.
As the used phenols of this alkali-soluble phenolics of preparation, can enumerate for example toluene phenols such as o-cresol, p-cresol and m-cresol; 3,5-xylenol, 2,5-xylenol, 2,3-xylenol, 3, dimethyl benzene phenols such as 4-xylenol; 2,3,4-pseudocuminol, 2,3,5-pseudocuminol, 2,4,5-pseudocuminol, 3,4, trimethylbenzene phenols such as 5-pseudocuminol; Tert-butyl phenols such as 2-tert-butyl phenol, 3-tert-butyl phenol, 4-tert-butyl phenol; 2-metoxyphenol, 3-metoxyphenol, 4-metoxyphenol, 2,3-syringol, 2,5-syringol, 3, methoxybenzene phenols such as 5-syringol; 2-ethyl-phenol, 3-ethyl-phenol, 4-ethyl-phenol, 2,3-diethyl phenol, 3,5-diethyl phenol, 2,3,5-triethyl phenol, 3,4, ethyl phenols such as 5-triethyl phenol; Neighbour-chlorophenol ,-chlorophenol, right-chlorophenol, 2, chlorobenzene phenols such as 3-chlorophenesic acid; Resorcinol classes such as resorcinol, 2-methylresorcinol, cresorcinol, oreinol diphenol; Catechols such as 5-methyl pyrocatechol; Pyrogallol classes such as 5-methyl pyrogallol; Bisphenols such as bisphenol-A, B, C, D, E, F; 2,6-dihydroxymethyl-right-methylolation cresols classes such as cresols; Aphthols such as alpha-Naphthol, betanaphthol etc.They can use separately or with multiple potpourri.
In addition, as aldehydes, except formalin, can also enumerate salicylide, paraformaldehyde, acetaldehyde, benzaldehyde, hydroxy benzaldehyde, chloroacetaldehyde etc., they can use separately or with multiple potpourri.
As alkali-soluble phenolics used herein, can use and separate the alkali-soluble phenolics of removing low molecular weight compositions.As the method that low molecular weight compositions is removed in separation, method of for example can enumerate the liquid-liquid separating method of separation resin in having different deliquescent two kinds of solvents, removing through the centrifuging low molecular weight compositions or thin-film distillation method etc.
As emulsion, preferably can enumerate the emulsion that contains the quinone diazido.Contain the emulsion of quinone diazido as this, any one in the known emulsion of in quinone two nitrine-phenolic resist, using before can using.As this emulsion, preferably with naphthoquinones two nitrine sulfonic acid chlorides or benzoquinones two nitrine sulfonic acid chlorides etc. with have the reaction of low molecular compound or macromolecular compound and the compound that obtains that can carry out the functional group of condensation reaction with these chloride things.Here, can enumerate hydroxyl, amino etc. with the functional group of chloride thing condensation, and hydroxyl is particularly suitable for.As hydroxyl can with the compound of chloride thing condensation, can enumerate for example p-dihydroxy-benzene, resorcinol, 2,4-hydroxy benzophenone, 2,3,4-trihydroxy benzophenone, 2,4; 6-trihydroxy benzophenone, 2,4,4 '-trihydroxy benzophenone, 2,3,4,4 '-tetrahydroxybenzophenone, 2; 2 ', 4,4 '-tetrahydroxybenzophenone, 2,2 ', 3,4; Hydroxy phenyl alkanes, 4 such as hydroxy benzophenone classes, two such as 6 '-pentahydroxybenzophenone (2, the 4-dihydroxy phenyl) methane, two (2,3,4-trihydroxy phenyl) methane, two (2, the 4-dihydroxy phenyl) propane, 4 '; 3 ", 4 "-tetrahydroxy-3,5,3 ', 5 '-tetramethyl triphenyl methane, 4,4 '; 2 ", 3 ", 4 "-penta hydroxy group-3,5, hydroxyl triphenylmethanes such as 3 ', 5 '-tetramethyl triphenyl methane etc.They can use separately, and also can make up use more than 2 kinds.
In addition, as sulfonic acid chlorides such as naphthoquinones two nitrine sulfonic acid chlorides or benzoquinones two nitrine sulfonic acid chlorides, for example preferably can enumerate 1,2-naphthoquinones two nitrine-5-sulfonic acid chloride, 1,2-naphthoquinones two nitrine-4-sulfonic acid chloride etc.The combined amount that contains the emulsion of quinone diazido, per 100 weight portion alkali soluble resins are generally the 5-50 weight portion, are preferably the 10-40 weight portion.If also lack than this amount, then can not obtain enough susceptibilitys as photosensitive resin composition, on the other hand,, then can produce the problem that becomes to analyze if more than this amount, therefore should be noted that.
Photosensitive resin composition of the present invention contains fatty acid and pure ester.The fatty acid here is that carbon number is carboxylic acid, particularly monocarboxylic acid or the dicarboxylic acids of the chain hydrocarbon of 10-20, preferred 14-18, and it can be a saturated fatty acid, also can be unsaturated fatty acid, and hydrocarbon can also have side chain.In addition, in the scope of not damaging effect of the present invention, can also be by replacements such as hydroxyl, amino.Alcohol can use the lower alcohol of carbon number as 1-5, preferred 1-3, preferred especially monohydroxy alcohol.Through these fatty acid and alcohol are reacted, can obtain ester used in the photosensitive resin composition of the present invention under common enzymatic synthesis condition.
Object lesson as preferred ester in the photosensitive resin composition of the present invention; For example; Polyunsaturated fatty acid ester can be enumerated methyl laurate, ethyl laurate, methyl myristate, ethyl myristate, soft-methyl ester, soft-ethyl ester, methyl stearate, ethyl stearte, and unsaturated fatty acid ester can be enumerated methyl oleate, ethyl oleate, castor oil acid methyl esters, castor oil acid ethyl ester, methyl linoleate, ethyl linoleate, methyl linolenate, ethyl linolenate etc.These esters can separately or mix more than 2 kinds and use as required.
The addition of ester, the total weight with respect to 100 weight portion phenolics and emulsion is generally the 1-20 weight portion, is preferably the 1-10 weight portion.If the content of ester also lacks than this amount, then can not fully show effect of the present invention, promptly can damage the homogeneity that applies thickness; In addition, if more than this amount, the tendency that then exists susceptibility to descend; Thereby can not obtain enough susceptibilitys, therefore should be noted that.
Photosensitive resin composition of the present invention can contain solvent as required.Solvent generally includes the solvent that above-mentioned each composition and following adjuvant are dissolved.As operable solvent; Can enumerate lactone such as amide-types such as ketone, DMAC N,N, N-Methyl pyrrolidone, gamma-butyrolacton class such as lactic acid esters such as propylene-glycol monoalky lether acetate esters, methyl lactate, ethyl lactate, toluene, xylene etc. such as propylene-glycol monoalky lether class, propylene glycol methyl ether acetate, propylene glycol monoethyl ether acetates such as ethylene glycol monoalkyl ether acetate class, propylene glycol monomethyl ether, dihydroxypropane single-ethers such as ethylene glycol monoalkyl ether class, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetates such as glycol monoethyl ether, ethylene glycol monoethyl ether are aromatic hydrocarbon based, methyl ethyl ketone, 2-heptanone, cyclohexanone etc.These solvents can separately or mix more than 2 kinds and use.
Photosensitive resin composition of the present invention can also contain surfactant as required.When being coated on photosensitive resin composition on the base material, the surface is gone up and can be produced flakey texture (below be called " fuzzy inequality "), and through in photosensitive resin composition of the present invention, using surfactant, can suppress this fuzzy inequality.Especially preferably use nonionic class surfactant in the photosensitive resin composition of the present invention.As nonionic class surfactant, comprise fluorine class surfactant, silicon class surfactant, hydrocarbon-surfactant etc., especially preferably use fluorine class surfactant.The combined amount of these surfactants with respect to the total amount of 1 weight portion alkali soluble resin and emulsion, is added 200-10000ppm usually.If the content of surfactant is too much, then can cause problems such as poor visualization, therefore should be noted that.
In addition, photosensitive resin composition of the present invention can also contain phenoloid as required.Through in photosensitive resin composition of the present invention, using phenoloid, the effect of the susceptibility that can be improved.This phenoloid is the compound of for example formula (I) expression:
(in the formula, R
1, R
2, R
3, R
4, R
5, R
6And R
7Represent H, C independently of one another
1-C
4Alkyl perhaps
(R here,
8Be H, C
1-C
4Alkyl), m and n are the integer of 0-2 independently of one another, a, b, c, d, e, f, g and h be for satisfying a+b≤5, c+d≤5, e+f≤5, the integer of the 0-5 of g+h≤5, i are the integer of 0-2).
As the object lesson of this phenoloid, can enumerate o-cresol, m-cresol and p-cresol, 2,4-xylenol, 2,5-xylenol, 2; 6-xylenol, bisphenol-A, B, C, E, F and G, 4,4 ', 4 "-and methine triphenol, 2,6-two [(2-hydroxy-5-methyl base phenyl) methyl]-4-methylphenol, 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, 4-[two (4-hydroxy phenyl) methyl]-2-thanatol, 4; 4 '-[(2-hydroxy phenyl) methylene] two [2, the 3-xylenol], 4,4 '-[(3-hydroxy phenyl) methylene] two [2, the 6-xylenol], 4; 4 '-[(4-hydroxy phenyl) methylene] two [2, the 6-xylenol], 2,2 '-[(2-hydroxy phenyl) methylene] two [3, the 5-xylenol], 2; 2 '-[(4-hydroxy phenyl) methylene] two [3, the 5-xylenol], 4,4 '-[(3, the 4-dihydroxy phenyl) methylene] two [2; 3,6-pseudocuminol], 4-[two (3-cyclohexyl-4-hydroxyl-6-aminomethyl phenyl) methyl]-1,2-benzenediol, 4,6-two [(3; 5-dimethyl-4-hydroxy phenyl) methyl]-1,2,3-benzenetriol, 4,4 '-[(2-hydroxy phenyl) methylene] two [3-methylphenols], 4; 4 ', 4 " triphenol, 4-(3-methyl isophthalic acid-dichloropropionanilide-3-time base (イ リ ジ Application)), 4 ', 4 "; 4 " '-(1,4-benzene two methines) four phenol, 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]-1,3-benzenediol, 4; 4 '-[1-[4-[1-[4-hydroxyl-3,5-two [(hydroxy-3-methyl phenyl) methyl] phenyl]-1-Methylethyl] phenyl] ethylidene] two [2,6-two (hydroxy-3-methyl phenyl) methyl] phenol etc.And, can enumerate 4,4 '; 4 as preferred compound "-methine triphenol, 2; 6-two [(2-hydroxy-5-methyl base phenyl) methyl]-4-methylphenol, 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 "-the ethylidine triphenol etc.
In this phenoloid, preferred especially formula (Ia) or compound (Ib).
The addition of phenoloid under the situation of adding, with respect to 100 weight portion alkali-soluble phenolics and emulsion, is generally the 1-25 weight portion, is preferably the 1-20 weight portion.
Photosensitive resin composition of the present invention obtains by containing above-mentioned each composition, and its proterties is solution or dispersion liquid.Usually, be modulated into the coating condition that viscosity is suitable for applying said composition, the preferred dynamic viscosity of photosensitive resin composition of the present invention under 25 ℃ is 2-10cSt, more preferably 2-5cSt.If dynamic viscosity drops on this beyond scope, no matter be too high or low excessively, all can damage the homogeneity that applies thickness, therefore should be noted that.
The present invention is described as follows according to embodiment.
Embodiment 1
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
Activating agent: fluorine class surfactant メ ガ Off ア Star Network (the chemical society of big Japanese ink produces), with respect to all solids composition, add 6000ppm.
All solids composition 100 weight portions with respect to above-mentioned composition; After adding 10 parts of methyl stearates; Stirring and dissolving adopts キ ヤ ノ Application Off エ Application ス ケ automatic viscometer (manufacturing of clutch society of Co., Ltd.) once more, regulates solids content concn; Making its dynamic viscosity under 25 ℃ is 4cSt, obtains composition.
Embodiment 2
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones two nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
Activating agent: fluorine class surfactant メ ガ Off ア Star Network (the chemical society of big Japanese ink produces), with respect to all solids composition, add 6000ppm.
All solids composition 100 weight portions with respect to above-mentioned composition; After adding 10 parts of ethyl steartes, stirring and dissolving adopts キ ヤ ノ Application Off エ Application ス ケ automatic viscometer to regulate solids content concn once more; Making its dynamic viscosity under 25 ℃ is 4cSt, obtains composition.
Comparative example 1
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones two nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
After making solid composite dissolving with solvent, adopt キ ヤ ノ Application Off エ Application ス ケ automatic viscometer to regulate solids content concn, making its dynamic viscosity under 25 ℃ is 4c St, obtains composition.
Comparative example 2
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones two nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
Activating agent: fluorine class surfactant メ ガ Off ア Star Network (the chemical society of big Japanese ink produces), with respect to all solids composition, add 6000ppm.
After making solid composite dissolving with solvent, adopt キ ヤ ノ Application Off エ Application ス ケ automatic viscometer to regulate solids content concn, making its dynamic viscosity under 25 ℃ is 4cSt, obtains composition.
Embodiment 3
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones two nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
With respect to all solids composition 100 weight portions of above-mentioned composition, add 10 parts of methyl stearates after, stirring and dissolving once more adopts キ ヤ ノ Application Off エ Application ス ケ automatic viscometer to regulate solids content concn, making its dynamic viscosity under 25 ℃ is 4cSt.
Embodiment 4
Phenolics: weight-average molecular weight is about 10000 phenolics with polystyrene conversion.
Emulsion: average esterification yield be 75% 2,3,4,4 '-tetrahydroxybenzophenone and 1, the ester compounds of 2-naphthoquinones two nitrine-5-sulfonic acid chloride adds 25 weight portions with respect to 100 weight portion phenolics.
(Honshu Chemical Ind produces phenoloid: TrisP-PA: general formula (Ia)) with respect to 100 weight portion phenolics and emulsion, add 5 weight portions.
Activating agent: fluorine class surfactant メ ガ Off ア Star Network (the chemical society of big Japanese ink produces), with respect to all solids composition, add 6000ppm.
All solids composition 100 weight portions with respect to above-mentioned composition; After adding 10 parts of methyl stearates, stirring and dissolving adopts キ ヤ ノ Application Off エ Application ス ケ automatic viscometer to regulate solids content concn once more; Making its dynamic viscosity under 25 ℃ is 4cSt, obtains composition.
Apply Evaluation for Uniformity
Adopt slit die applicator to be coated on that (substrate size 1100 * 1250mm), drying under reduced pressure carry out prebake through heating plate then, form the ultraviolet curable resin film of about 1.5 μ m on the glass substrate each photosensitive resin composition.
Adopt the blooming analyzer; On coating direction and vertical direction, measure 90 points to right-hand member from the substrate left end; Point except the 50mm of substrate end, except the 20mm, except the 15mm, except the 10mm is calculated average film thickness and maximal value, minimum value, obtain inner evenness (%) through following formula.
(maximal value-minimum value)/average film thickness/2 * 100
Then, difference less than 2% be evaluated as ◎, be the O that is evaluated as of 2% above less than 3%, 3% above less than 4% be evaluated as △, be evaluated as more than 4% *.The gained result lists in table 1.
Table 1
The evaluation of coated surface proterties
In addition, the proterties that visual observations is filmed under sodium vapor lamp is estimated.The applicator surface of comparative example 1 sample is found fuzzy uneven, contains the embodiment 1,2 of ester and surfactant and the applicator surface of 4 sample and does not observe fuzzy inequality fully.
Claims (4)
1. photosensitive resin composition that is used for irrotationality, slit die coating process; It is characterized in that containing alkali-soluble phenolics, contain the emulsion that the quinone diazido is rolled into a ball; With carbon number be that the carboxylic acid and the carbon number of the chain hydrocarbon of 14-18 is the ester of the monohydroxy alcohol of 1-3; The combined amount of wherein said emulsion, per 100 weight portion alkali-soluble phenolics are the 5-50 weight portion, the dynamic viscosity of said resin combination under 25 ℃ is 2-10cSt.
2. the described photosensitive resin composition of claim 1 wherein also contains surfactant.
3. claim 1 or 2 described photosensitive resin compositions wherein further contain phenoloid.
4. the manufacturing approach of a resist substrate is characterized in that comprising each described photosensitive resin composition in the claim 1～3 is coated on the substrate through irrotationality, slit die coating process.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2006-023388 | 2006-01-31 | ||
| JP2006023388 | 2006-01-31 | ||
| JP2006023388A JP4813193B2 (en) | 2006-01-31 | 2006-01-31 | Photosensitive resin composition suitable for spinless and slit coating |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101013263A CN101013263A (en) | 2007-08-08 |
| CN101013263B true CN101013263B (en) | 2012-05-30 |
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| CN200710001223XA Expired - Fee Related CN101013263B (en) | 2006-01-31 | 2007-01-04 | Photosensitive resin composition suitable for irrational and slit mold coating method |
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| Country | Link |
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| JP (1) | JP4813193B2 (en) |
| KR (1) | KR101285574B1 (en) |
| CN (1) | CN101013263B (en) |
| TW (1) | TWI387849B (en) |
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| JP5090833B2 (en) * | 2007-09-11 | 2012-12-05 | 東京応化工業株式会社 | Positive photoresist composition and photosensitive film-coated substrate using the same |
| JP5329999B2 (en) * | 2009-01-29 | 2013-10-30 | ＡｚエレクトロニックマテリアルズＩｐ株式会社 | Pattern formation method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314617A (en) * | 2000-03-22 | 2001-09-26 | 富士胶片株式会社 | Positive sensitive flat-plate printing plate |
| CN1518685A (en) * | 2001-06-12 | 2004-08-04 | ���Ͽع�����˾ | Method for forming thick resist pattern |
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|---|---|---|---|---|
| JP3842446B2 (en) * | 1997-09-25 | 2006-11-08 | 富士写真フイルム株式会社 | Positive photosensitive composition for infrared laser |
| JP2004138995A (en) * | 2002-08-21 | 2004-05-13 | Fuji Photo Film Co Ltd | Plate making method for planographic printing plate |
| JP4545553B2 (en) * | 2004-03-12 | 2010-09-15 | 東京応化工業株式会社 | Non-spin coating positive photoresist composition and resist pattern forming method |
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- 2006-01-31 JP JP2006023388A patent/JP4813193B2/en not_active Expired - Fee Related
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2007
- 2007-01-04 CN CN200710001223XA patent/CN101013263B/en not_active Expired - Fee Related
- 2007-01-19 TW TW096101989A patent/TWI387849B/en not_active IP Right Cessation
- 2007-01-30 KR KR1020070009580A patent/KR101285574B1/en active IP Right Grant
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1314617A (en) * | 2000-03-22 | 2001-09-26 | 富士胶片株式会社 | Positive sensitive flat-plate printing plate |
| CN1518685A (en) * | 2001-06-12 | 2004-08-04 | ���Ͽع�����˾ | Method for forming thick resist pattern |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101013263A (en) | 2007-08-08 |
| TW200739254A (en) | 2007-10-16 |
| TWI387849B (en) | 2013-03-01 |
| KR20070079028A (en) | 2007-08-03 |
| JP4813193B2 (en) | 2011-11-09 |
| JP2007206256A (en) | 2007-08-16 |
| KR101285574B1 (en) | 2013-07-15 |
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