KR20130114790A - Photosensitive resin composition comprising alkali soluble resin - Google Patents
Photosensitive resin composition comprising alkali soluble resin Download PDFInfo
- Publication number
- KR20130114790A KR20130114790A KR1020120037095A KR20120037095A KR20130114790A KR 20130114790 A KR20130114790 A KR 20130114790A KR 1020120037095 A KR1020120037095 A KR 1020120037095A KR 20120037095 A KR20120037095 A KR 20120037095A KR 20130114790 A KR20130114790 A KR 20130114790A
- Authority
- KR
- South Korea
- Prior art keywords
- photosensitive resin
- resin composition
- acrylate
- meth
- structural unit
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 41
- 239000011347 resin Substances 0.000 title claims abstract description 30
- 229920005989 resin Polymers 0.000 title claims abstract description 30
- 239000003513 alkali Substances 0.000 title abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 239000002904 solvent Substances 0.000 claims abstract description 15
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003999 initiator Substances 0.000 claims abstract description 7
- -1 carbazole oxime Chemical class 0.000 claims description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- UJOBWOGCFQCDNV-UHFFFAOYSA-N Carbazole Natural products C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 11
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 238000009413 insulation Methods 0.000 abstract 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 58
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 238000000576 coating method Methods 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000004611 light stabiliser Substances 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 229960004063 propylene glycol Drugs 0.000 description 5
- 235000013772 propylene glycol Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000006087 Silane Coupling Agent Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000003505 polymerization initiator Substances 0.000 description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- QKJHNPXSYSFZMJ-UHFFFAOYSA-N 4-ethenyl-2-methylphenol Chemical compound CC1=CC(C=C)=CC=C1O QKJHNPXSYSFZMJ-UHFFFAOYSA-N 0.000 description 2
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 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 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000010894 electron beam technology Methods 0.000 description 2
- 238000005530 etching Methods 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical compound CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- 229940093476 ethylene glycol Drugs 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N propyl acetate Chemical compound CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 2
- 238000005057 refrigeration Methods 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 238000002411 thermogravimetry Methods 0.000 description 2
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- HZBSQYSUONRRMW-UHFFFAOYSA-N (2-hydroxyphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1O HZBSQYSUONRRMW-UHFFFAOYSA-N 0.000 description 1
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 description 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- PVMMVWNXKOSPRB-UHFFFAOYSA-N 1,2-dipropoxypropane Chemical compound CCCOCC(C)OCCC PVMMVWNXKOSPRB-UHFFFAOYSA-N 0.000 description 1
- ZCCAOOJIWMTVGN-UHFFFAOYSA-N 1,6-diisocyanatohexane;[2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound O=C=NCCCCCCN=C=O.C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C ZCCAOOJIWMTVGN-UHFFFAOYSA-N 0.000 description 1
- QMGJMGFZLXYHCR-UHFFFAOYSA-N 1-(2-butoxypropoxy)butane Chemical compound CCCCOCC(C)OCCCC QMGJMGFZLXYHCR-UHFFFAOYSA-N 0.000 description 1
- CNDOSNMFHUSKGN-UHFFFAOYSA-N 1-(2-hydroxyphenyl)pyrrole-2,5-dione Chemical compound OC1=CC=CC=C1N1C(=O)C=CC1=O CNDOSNMFHUSKGN-UHFFFAOYSA-N 0.000 description 1
- FPZQYYXSOJSITC-UHFFFAOYSA-N 1-(4-chlorophenyl)pyrrole-2,5-dione Chemical compound C1=CC(Cl)=CC=C1N1C(=O)C=CC1=O FPZQYYXSOJSITC-UHFFFAOYSA-N 0.000 description 1
- XUIXZBXRQFZHIT-UHFFFAOYSA-N 1-[1-(1-hydroxypropan-2-yloxy)propan-2-yloxy]-3-methoxypropan-2-ol Chemical compound COCC(O)COC(C)COC(C)CO XUIXZBXRQFZHIT-UHFFFAOYSA-N 0.000 description 1
- RWNUSVWFHDHRCJ-UHFFFAOYSA-N 1-butoxypropan-2-ol Chemical compound CCCCOCC(C)O RWNUSVWFHDHRCJ-UHFFFAOYSA-N 0.000 description 1
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- LGJCFVYMIJLQJO-UHFFFAOYSA-N 1-dodecylperoxydodecane Chemical compound CCCCCCCCCCCCOOCCCCCCCCCCCC LGJCFVYMIJLQJO-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound 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
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 1
- PQJZHMCWDKOPQG-UHFFFAOYSA-N 2-anilino-2-oxoacetic acid Chemical compound OC(=O)C(=O)NC1=CC=CC=C1 PQJZHMCWDKOPQG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- HFCUBKYHMMPGBY-UHFFFAOYSA-N 2-methoxyethyl prop-2-enoate Chemical compound COCCOC(=O)C=C HFCUBKYHMMPGBY-UHFFFAOYSA-N 0.000 description 1
- WUQYBSRMWWRFQH-UHFFFAOYSA-N 2-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC=C1O WUQYBSRMWWRFQH-UHFFFAOYSA-N 0.000 description 1
- YNGIFMKMDRDNBQ-UHFFFAOYSA-N 3-ethenylphenol Chemical compound OC1=CC=CC(C=C)=C1 YNGIFMKMDRDNBQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- REWLXMVGEZMKSG-UHFFFAOYSA-N 3-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=CC(O)=C1 REWLXMVGEZMKSG-UHFFFAOYSA-N 0.000 description 1
- LDMRLRNXHLPZJN-UHFFFAOYSA-N 3-propoxypropan-1-ol Chemical compound CCCOCCCO LDMRLRNXHLPZJN-UHFFFAOYSA-N 0.000 description 1
- CFZDMXAOSDDDRT-UHFFFAOYSA-N 4-ethenylmorpholine Chemical compound C=CN1CCOCC1 CFZDMXAOSDDDRT-UHFFFAOYSA-N 0.000 description 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 1
- JAGRUUPXPPLSRX-UHFFFAOYSA-N 4-prop-1-en-2-ylphenol Chemical compound CC(=C)C1=CC=C(O)C=C1 JAGRUUPXPPLSRX-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-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
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Natural products CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- COMYKUGGAIHLIE-UHFFFAOYSA-N CCCCCCCCCCCCCCCCC(C(=O)O)N1C(CCCC1(C)C)(C)C Chemical compound CCCCCCCCCCCCCCCCC(C(=O)O)N1C(CCCC1(C)C)(C)C COMYKUGGAIHLIE-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 1
- IJMWOMHMDSDKGK-UHFFFAOYSA-N Isopropyl propionate Chemical compound CCC(=O)OC(C)C IJMWOMHMDSDKGK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/235—Saturated compounds containing more than one carboxyl group
- C07C59/245—Saturated compounds containing more than one carboxyl group containing hydroxy or O-metal groups
- C07C59/285—Polyhydroxy dicarboxylic acids having five or more carbon atoms, e.g. saccharic acids
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
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- C08F2/46—Polymerisation initiated by wave energy or particle radiation
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- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
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- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
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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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- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
-
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- 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
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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Abstract
Description
본 발명은 알칼리 가용성 수지를 함유하는 감광성 수지 조성물에 관한 것이다. 구체적으로, 본 발명은 보관 안정성이 개선될 뿐만 아니라, 부착성 및 내열성이 우수한 유기 절연막을 형성할 수 있는 알칼리 가용성 수지를 함유하는 감광성 수지 조성물에 관한 것이다.This invention relates to the photosensitive resin composition containing alkali-soluble resin. Specifically, the present invention relates to a photosensitive resin composition containing an alkali-soluble resin that can not only improve storage stability but also form an organic insulating film excellent in adhesion and heat resistance.
액정표시장치에 사용되는 TFT 기판은, TFT 소자와 화소 전극을 형성하는 투명 도전막 사이에, TFT 어레이 소자를 보호하기 위한 유기 절연막을 갖는다. The TFT substrate used for the liquid crystal display device has an organic insulating film for protecting the TFT array element between the TFT element and the transparent conductive film forming the pixel electrode.
이러한 절연막은 화소 전극 형성 공정에서와 같이 고온에 노출되므로 내열성이 요구되고, 또한, 하부 층과의 부착력이 매우 우수할 것이 요구되는데, 상기 부착력이 부족할 경우, 에칭 과정에서 에칭 용액이 하부 층과 절연막 사이로 침투하여 패턴의 CD(Critical Dimension)가 달라질 수 있으며 경우에 따라서는 패턴 전체가 소실될 수도 있다. 특히, 상기 알칼리 가용성 수지는 알칼리 가용성을 높이기 위해 통상적으로 카복실기를 포함하는데, 상기 카복실기는 에폭시기와 같은 다른 기와의 반응성으로 인하여 경시 변화가 급격하게 진행되어 상온에서 보관이 어렵고 안정적으로 공정에서 사용이 어렵다. 따라서, 감광성 수지 조성물을 대략 5℃에서 냉장 보관하는 방법이 있으나 보관 장소나 냉장 시설에 따른 부수 비용이 발생하여 바람직하지 않다. 또한, 상기 카복실기를 포함하는 알칼리 가용성 수지를 사용하여 절연막을 형성하면, 알칼리 현상액에 대한 용해도가 과도하게 상승되어 현상 동안에 언더 컷이 발생하고, 이에 의해 10㎛ 이하의 작은 패턴이 유실되는 등의 단점이 있다. 이러한 현상을 방지하기 위해 알칼리 현상액의 온도를 낮추거나 전열처리 시간을 늘리는 방법이 있으나, 이 역시 공정 조건을 변경하며 최적화하는데 따른 비용 상승이라는 단점이 있다.Since the insulating film is exposed to high temperature as in the pixel electrode forming process, heat resistance is required, and the adhesion force with the lower layer is required to be very excellent. When the adhesion force is insufficient, the etching solution is formed during the etching process. Penetrating in between the CD (Critical Dimension) of the pattern may vary, and in some cases the entire pattern may be lost. Particularly, the alkali-soluble resin generally includes a carboxyl group to increase alkali solubility, and the carboxyl group is rapidly changed over time due to the reactivity with other groups such as epoxy groups, making it difficult to store at room temperature and stably difficult to use in the process. . Therefore, there is a method of refrigeration of the photosensitive resin composition at approximately 5 ° C, but it is not preferable because of the incidental cost according to the storage location or the refrigeration facility. In addition, when the insulating film is formed using the alkali-soluble resin containing the carboxyl group, the solubility in the alkaline developer is excessively increased, resulting in undercuts during the development, which results in the loss of a small pattern of 10 μm or less. There is this. In order to prevent such a phenomenon, there is a method of lowering the temperature of the alkaline developer or increasing the heat treatment time, but this also has the disadvantage of increasing the cost of changing and optimizing the process conditions.
대한민국 공개특허공보 제2009-0058458호는 페닐기를 포함하는 단량체로부터 유래되는 구성 단위, 에폭시기를 포함하는 단량체로부터 유래되는 구성 단위 및 히드록시기를 포함하는 단량체로부터 유래되는 구성 단위를 갖고 카복실기는 포함하지 않는 알칼리 가용성 수지를 함유하는 감광성 수지 조성물이 개시되어 있다. 그러나, 상기 선행 문헌은 해당 감광성 수지 조성물을 사용하여 형성된 막의 부착력이 여전히 만족할 수준에 있지 않으며, 또한, 막의 내열성에 대해서는 전혀 고려하는 바가 없다.Korean Unexamined Patent Publication No. 2009-0058458 discloses an alkali having a structural unit derived from a monomer containing a phenyl group, a structural unit derived from a monomer containing an epoxy group, and a structural unit derived from a monomer containing a hydroxy group and not containing a carboxyl group. A photosensitive resin composition containing soluble resin is disclosed. However, the above-mentioned literature does not consider the adhesion of the film formed using the photosensitive resin composition still satisfactory, and also does not consider the heat resistance of the film at all.
이에, 본 발명은 보관 안정성이 개선될 뿐만 아니라, 부착성 및 내열성이 우수한 유기 절연막을 형성할 수 있는 알칼리 가용성 수지를 함유하는 감광성 수지 조성물을 제공하는 것을 목적으로 한다.Accordingly, an object of the present invention is to provide a photosensitive resin composition containing an alkali-soluble resin that can not only improve storage stability but also form an organic insulating film excellent in adhesion and heat resistance.
상술한 과제를 달성하기 위한 기술적 수단으로서, 본 발명은 구현예로서 (a-1) 페놀기를 포함하는 에틸렌성 불포화 화합물로부터 유래되는 구성 단위; (a-2) 에폭시기를 1개 이상 포함하는 에틸렌성 불포화 화합물로부터 유래되는 구성 단위; 및 (a-3) 스티렌계 불포화 화합물로부터 유래되는 구성 단위를 포함하고, 카복실기를 포함하지 않는 (A) 알칼리 가용성 수지; (B) 하나 이상의 에틸렌성 불포화 결합을 포함하는 중합성 화합물; (C) 광중합 개시제; 및 (D) 용매를 함유하는 감광성 수지 조성물을 제공한다.As a technical means for achieving the above-mentioned subject, this invention is a structural unit derived from the ethylenically unsaturated compound containing a phenol group as an embodiment (a-1); (a-2) Structural unit derived from the ethylenically unsaturated compound containing one or more epoxy groups; And (a-3) (A) alkali-soluble resin which contains a structural unit derived from a styrenic unsaturated compound and does not contain a carboxyl group; (B) a polymerizable compound comprising at least one ethylenically unsaturated bond; (C) a photopolymerization initiator; And (D) a photosensitive resin composition containing a solvent.
또한, 본 발명은 또다른 구현예로서, 상기 감광성 수지 조성물을 사용하여 제조하는 유기 절연막을 제공한다.In another aspect, the present invention provides an organic insulating film prepared by using the photosensitive resin composition.
본 발명의 감광성 수지 조성물은 보관 안정성이 우수할 뿐만 아니라, 하부 층과의 부착성 및 내열성이 우수한 유기 절연막을 제공할 수 있다.The photosensitive resin composition of this invention is not only excellent in storage stability, but can also provide the organic insulating film excellent in adhesiveness and heat resistance with a lower layer.
이하, 본 발명에 대해 구체적으로 설명한다.Hereinafter, the present invention will be described in detail.
(A) 알칼리 가용성 수지 (A) an alkali-soluble resin
(a-1) (a-1) 페놀기를Phenol group 포함하는 Containing 에틸렌성Ethylenic 불포화 화합물로부터 From unsaturated compounds 유래되는Derived 구성 단위 constituent unit
본 발명의 구성 단위 (a-1)를 형성하기 위한 페놀기를 포함하는 에틸렌성 불포화 화합물로는 o-비닐페놀, m-비닐페놀, p-비닐페놀, 2-메틸-4-비닐페놀, 3-메틸-4-비닐페놀, o-이소프로페닐페놀, m-이소프로페닐페놀, p-이소프로페닐페놀 등의 불포화 페놀, N-(히드록시페닐)(메트)아크릴아미드, N-(히드록시페닐)말레이미드 및 하기 화학식 1을 들 수 있다. 이 중에서도 화학식 1의 화합물이 보관 안정성의 면에서 우수하다.As an ethylenically unsaturated compound containing the phenol group for forming the structural unit (a-1) of this invention, o-vinyl phenol, m-vinyl phenol, p-vinyl phenol, 2-methyl-4- vinyl phenol, 3- Unsaturated phenols such as methyl-4-vinylphenol, o-isopropenylphenol, m-isopropenylphenol, and p-isopropenylphenol, N- (hydroxyphenyl) (meth) acrylamide, N- (hydroxy Phenyl) maleimide and the following general formula (1). Among them, the compound of formula 1 is excellent in terms of storage stability.
[화학식 1][Formula 1]
상기 화학식 1에서, R1은 단일 결합 또는 C1-C10 알킬렌기, 바람직하게는 C1-C5 알킬렌기이고, R2는 수소 원자 또는 C1-C6 알킬기, 바람직하게는 수소 원자 또는 C1-C3 알킬기이다.In Formula 1, R 1 is a single bond or a C 1 -C 10 alkylene group, preferably a C 1 -C 5 alkylene group, R 2 is a hydrogen atom or a C 1 -C 6 alkyl group, preferably a hydrogen atom or C 1 -C 3 alkyl group.
상기 (a-1) 페놀기를 포함하는 에틸렌성 불포화 화합물로부터 유래되는 구성 단위의 함량은 알칼리 가용성 수지 총 중량에 대하여 15 내지 70 중량%이고, 바람직하게는 25 내지 60중량%이고, 보다 바람직하게는 30 내지 50중량%이다. 상기 범위에서 현상성 우수하고, 공정마진이 확보된다.The content of the structural unit derived from the ethylenically unsaturated compound containing the phenol group (a-1) is 15 to 70% by weight, preferably 25 to 60% by weight, more preferably based on the total weight of the alkali-soluble resin. 30 to 50% by weight. It is excellent in developability in the said range, and process margin is ensured.
(a-2) 에폭시기를 1개 이상 포함하는 (a-2) containing at least one epoxy group 에틸렌성Ethylenic 불포화 화합물로부터 From unsaturated compounds 유래되는Derived 구성 단위 constituent unit
본 발명의 구성 단위 (a-2)를 형성하기 위한 에폭시기를 1개 이상 포함하는 에틸렌성 불포화 화합물로는 하기 화학식 2로 표시되는 것이 감광성 수지 조성물의 경화시에 부착성의 면에서 바람직하다:As an ethylenically unsaturated compound containing one or more epoxy groups for forming the structural unit (a-2) of this invention, what is represented by following General formula (2) is preferable at the point of adhesiveness at the time of hardening of the photosensitive resin composition:
[화학식 2](2)
상기 화학식 2에서, R3은 수소 원자 또는 C1-C2 알킬기, 바람직하게는 수소 원자 또는 메틸기이고, R4는 단일 결합 또는 C1-C10 알킬렌기, 바람직하게는 C1-C5 알킬렌기이고, R5는 수소 원자 또는 C1-C6 알킬기, 바람직하게는 수소 원자 또는 C1-C3 알킬기이다.In Formula 2, R 3 is a hydrogen atom or a C 1 -C 2 alkyl group, preferably a hydrogen atom or a methyl group, R 4 is a single bond or a C 1 -C 10 alkylene group, preferably C 1 -C 5 alkyl And R 5 is a hydrogen atom or a C 1 -C 6 alkyl group, preferably a hydrogen atom or a C 1 -C 3 alkyl group.
상기 (a-2) 에폭시기를 1개 이상 포함하는 에틸렌성 불포화 화합물로부터 유래되는 구성 단위의 함량은 알칼리 가용성 수지 총 중량에 대하여 5 내지 60중량%이고, 바람직하게는 10 내지 50 중량%이고, 보다 바람직하게는 20 내지 40중량%이다. 상기 범위에서 해상도가 안정적으로 구현이 가능하며 기판과의 접착력도 충분히 얻을 수 있는 장점이 있다.The content of the structural unit derived from the ethylenically unsaturated compound containing at least one epoxy group (a-2) is 5 to 60% by weight, preferably 10 to 50% by weight, based on the total weight of the alkali-soluble resin. Preferably it is 20-40 weight%. Resolution can be stably implemented in the above range, and there is an advantage that sufficient adhesion with the substrate can be obtained.
(a-3) (a-3) 스티렌계Styrene series 불포화 화합물로부터 From unsaturated compounds 유래되는Derived 구성 단위 constituent unit
본 발명의 구성 단위 (a-3)를 형성하기 위한 스티렌계 불포화 화합물로는 스티렌; 알파-메틸스티렌; 페닐기의 1내지 3개의 수소가 각각 독립적으로 직쇄상 또는 분지상의 C1-C8의 알킬기, -CHCH2, -COCH3, -CH2OCH3, 할로겐(플루오로, 클로로, 브로모, 또는 요오드) 원자 또는 C1-C3의 알콕시기로 치환된 스티렌으로 이루어진 그룹중에서 선택된 1종 이상이 바람직하고, 이 중에서 중합성 및 잔막률의 면에서 스티렌이 바람직하다. Examples of the styrenic unsaturated compound for forming the structural unit (a-3) of the present invention include styrene; Alpha-methylstyrene; One to three hydrogens of the phenyl group are each independently a linear or branched C 1 -C 8 alkyl group, -CHCH 2 , -COCH 3 , -CH 2 OCH 3 , halogen (fluoro, chloro, bromo, or At least one selected from the group consisting of styrene substituted with an iodine) atom or a C 1 -C 3 alkoxy group is preferred, and among these, styrene is preferred in view of polymerizability and residual film ratio .
상기 (a-3) 스티렌계 불포화 화합물로부터 유래되는 구성단위의 함량은 알칼리 가용성 수지 총 중량에 대하여 10내지 60 중량%이고, 바람직하게는 15 내지 55 중량%이고, 보다 바람직하게는 20 내지 50중량%인 것이 보다 바람직하다. 상기 범위에서, 적정 현상성을 유지하여 해상도와 잔막률 확보가 용이한 장점이 있다.The content of the structural unit derived from the styrene-based unsaturated compound (a-3) is 10 to 60% by weight, preferably 15 to 55% by weight, and more preferably 20 to 50% by weight based on the total weight of the alkali-soluble resin. It is more preferable that it is%. In the above range, there is an advantage that it is easy to secure the resolution and the residual film ratio by maintaining the appropriate developability.
(a-4) 추가의 구성 단위(a-4) additional structural units
본 발명에 따른 알칼리 가용성 수지는 필요에 따라, (a-4) 상기 구성 단위 (a-1) 내지 (a-3)과는 상이한 에틸렌성 불포화 화합물로부터 유래되는 구성 단위를 더 포함할 수 있다. Alkali-soluble resin which concerns on this invention can further contain the structural unit derived from ethylenically unsaturated compound different from (a-4) said structural unit (a-1)-(a-3) as needed.
상기 구성 단위 (a-4)를 형성하기 위한 에틸렌성 불포화 화합물로는 페닐(메트)아크릴레이트, 벤질(메트)아크릴레이트, 메틸(메트)아크릴레이트, 에틸(메트)아크릴레이트, 부틸(메트)아크릴레이트, 디메틸아미노에틸(메트)아크릴레이트, 이소부틸(메트)아크릴레이트, t-부틸(메트)아크릴레이트, 시클로헥실(메트)아크릴레이트, 이소보닐(메트)아크릴레이트, 에틸헥실(메트)아크릴레이트, 2-페녹시에틸(메트)아크릴레이트, 테트라히드로퍼프릴(메트)아크릴레이트, 히드록시에틸(메트)아크릴레이트, 2-히드록시프로필(메트)아크릴레이트, 2-히드록시-3-클로로프로필(메트)아크릴레이트, 4-히드록시부틸(메트)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메트)아크릴레이트, 글리세롤(메트)아크릴레이트, 2-메톡시에틸(메트)아크릴레이트, 3-메톡시부틸(메트)아크릴레이트, 에톡시디에틸렌글리콜(메트)아크릴레이트, 메톡시트리에틸렌글리콜(메트)아크릴레이트, 메톡시트리프로필렌글리콜(메트)아크릴레이트, 폴리(에틸렌글리콜)메틸에테르(메트)아크릴레이트, 페녹시디에틸렌글리콜(메트)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메트)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메트)아크릴레이트, 테트라플루오로프로필(메트)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필(메트)아크릴레이트, 옥타플루오로펜틸(메트)아크릴레이트, 헵타데카플루오로데실(메트)아크릴레이트, 트리브로모페닐(메트)아크릴레이트, 2-히드록시에틸(메트)아크릴레이트, 메틸 α-히드록시메틸아크릴레이트, 에틸 α-히드록시메틸아크릴레이트, 프로필 α-히드록시메틸아크릴레이트, 부틸 α-히드록시메틸아크릴레이트, 디시클로펜타닐(메트)아크릴레이트, 디시클로펜테닐(메트)아크릴레이트, 디시클로펜타닐옥시에틸(메트)아크릴레이트 및 디시클로펜테닐옥시에틸(메트)아크릴레이트를 포함하는 (메트)아크릴레이트계 화합물; N-비닐피롤리돈, N-비닐카바졸 및 N-비닐모폴린과 같은 N-비닐을 포함하는 N-비닐 삼차아민류; 비닐메틸에테르, 비닐에틸에테르 및 알릴글리시딜에테르를 포함하는 불포화 에테르류; 및 N-페닐말레이미드, N-(4-클로로페닐)말레이미드 및 N-시클로헥실말레이미드를 포함하는 불포화 이미드류;로 이루어진 그룹으로부터 선택된 1종 이상을 들 수 있다. Ethylenic unsaturated compounds for forming the structural unit (a-4) include phenyl (meth) acrylate, benzyl (meth) acrylate, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) Acrylate, dimethylaminoethyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, ethylhexyl (meth) Acrylate, 2-phenoxyethyl (meth) acrylate, tetrahydroperpril (meth) acrylate, hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3 -Chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxypropyl (meth) acrylate, glycerol (meth) acrylate, 2-methoxyethyl (meth) Acrylate, 3-methoxybutyl (meth) Acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxytripropylene glycol (meth) acrylate, poly (ethylene glycol) methyl ether (meth) acrylate, phenoxydi Ethylene glycol (meth) acrylate, p-nonylphenoxypolyethylene glycol (meth) acrylate, p-nonylphenoxypolypropylene glycol (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1 , 3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, 2 -Hydroxyethyl (meth) acrylate, methyl α-hydroxymethyl acrylate, ethyl α-hydroxymethyl acrylate, propyl α-hydroxymethyl acrylate, butyl α-hydroxymethyl acrylate (Meth) acrylate containing dicyclopentanyl (meth) acrylate, dicyclopentenyl (meth) acrylate, dicyclopentanyloxyethyl (meth) acrylate, and dicyclopentenyloxyethyl (meth) acrylate System compounds; N-vinyl tertiary amines including N-vinyl, such as N-vinylpyrrolidone, N-vinylcarbazole and N-vinylmorpholine; Unsaturated ethers including vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; And unsaturated imides including N-phenylmaleimide, N- (4-chlorophenyl) maleimide, and N-cyclohexylmaleimide.
상기 (a-4) 추가의 구성단위의 함량은 알칼리 가용성 수지 총 중량에 대하여 0 내지 30 중량%이고, 바람직하게는 5 내지 25 중량%이다. 상기 범위에서 조성물의 저장안정성이 유지되고, 잔막율이 향상한다.The content of the additional structural unit (a-4) is 0 to 30% by weight, preferably 5 to 25% by weight based on the total weight of the alkali-soluble resin. The storage stability of the composition is maintained in the above range, and the residual film ratio is improved.
본 발명에서, (메트)아크릴, (메트)아크릴레이트란 아크릴 및/또는 메타크릴, 아크릴레이트 및/또는 메타크릴레이트를 칭한다.In the present invention, (meth) acryl and (meth) acrylate refer to acrylic and / or methacryl, acrylate and / or methacrylate.
본 발명에 따른 알칼리 가용성 수지는 당업계에 공지된 통상의 방법에 따라 제조될 수 있다. 예를 들어, 상기 알칼리 가용성 수지는 분자량 조절제, 중합 개시제, 및 (a-1) 내지 (a-4)의 불포화 화합물을 적당한 용매에 넣고 질소를 투입한 후, 서서히 교반하면서 중합시켜 제조할 수 있다. 상기 분자량 조절제는 당업계에 공지된 임의의 것일 수 있으나, 부틸메캅탄, 옥틸메캅탄 등의 메캅탄 화합물 또는 α-메틸스티렌다이머인 것이 바람직하다. 또한, 상기 중합 개시제도 특별히 한정되지 않으나, 2,2'-아조비스이소부티로니트릴, 2,2'-아조비스(2,4-디메틸발레로니트릴), 2,2'-아조비스(4-메톡시-2,4-디메틸발레로니트릴) 등의 디아조 화합물 및 벤조일퍼옥사이드, 라우릴퍼옥사이드, t-부틸퍼옥시피발레이트, 1,1-비스(t-부틸퍼옥시)시클로헥산 등의 퍼옥시 화합물이 바람직하다.Alkali-soluble resins according to the present invention may be prepared according to conventional methods known in the art. For example, the alkali-soluble resin may be prepared by adding a molecular weight regulator, a polymerization initiator, and an unsaturated compound of (a-1) to (a-4) in a suitable solvent, adding nitrogen, and then slowly stirring to polymerize. . The molecular weight modifier may be any known in the art, but is preferably a mecaptan compound such as butyl mecaptan, octyl mecaptan or α-methylstyrene dimer. Moreover, the said polymerization initiator is not specifically limited, either 2,2'- azobisisobutyronitrile, 2,2'- azobis (2, 4- dimethylvaleronitrile), 2,2'- azobis (4 Diazo compounds such as -methoxy-2,4-dimethylvaleronitrile) and benzoyl peroxide, lauryl peroxide, t-butylperoxy pivalate, 1,1-bis (t-butylperoxy) cyclohexane Peroxy compounds, such as these, are preferable.
또한, 상기 용매는 상술한 성분들과 상용성을 가지되, 이들과 반응하지 않는 것이면 어느 것이나 사용 가능하다. 예를 들어, 프로필렌글리콜모노메틸에테르아세테이트가 사용될 수 있다.In addition, the solvent may be used as long as it is compatible with the above-described components and does not react with them. For example, propylene glycol monomethyl ether acetate can be used.
상기 알칼리 가용성 수지의 겔투과 크로마토그래피(GPC; 테트라히드로퓨란을 용출용매로 함)로 측정한 폴리스티렌 환산의 중량평균분자량(Mw)은 2,000 내지 40,000이고, 바람직하게는 5,000 내지 20,000이다. 상기 범위에서 이를 포함하는 조성물은 도포성이 우수하며, 경화막 형성시 잔막율이 우수하고, 해상도의 조절이 용이하여 원하는 특성을 얻기 쉽다.The gel permeation chromatography of the alkali-soluble resin; weight average molecular weight in terms of polystyrene as measured by gel permeation chromatography (GPC hereinafter tetrahydrofuran as eluting solvent) (M w) is from 2,000 to 40,000, preferably from 5,000 to 20,000. The composition including the same in the above range is excellent in coatability, excellent in residual film ratio when forming a cured film, and easy to control the resolution to obtain desired characteristics.
상기 알칼리 가용성 수지의 함량은 잔부량의 용매를 제외한 감광성 수지 조성물 전체 중량에 대하여 1 내지 60중량%이고, 바람직하게는 5 내지 50 중량%이다. 상기 범위에서 현상성이 적절히 조절되어 잔막 형성과 패턴의 해상도가 우수한 장점이 있다.
The content of the alkali-soluble resin is 1 to 60% by weight, preferably 5 to 50% by weight based on the total weight of the photosensitive resin composition excluding the residual amount of the solvent. The developability is appropriately adjusted in the above range, and there is an advantage in that the residual film formation and the resolution of the pattern are excellent.
(B) (B) 중합성Polymerizable 불포화 화합물 Unsaturated compounds
상기 중합성 불포화 화합물은 광중합 개시제의 작용으로 중합될 수 있는 화합물로서, 감광성 수지 조성물에 일반적으로 사용되는 모노머, 올리고머 또는 중합체로서, 적어도 1개의 에틸렌성 불포화 이중 결합을 가지는 아크릴산 또는 메타크릴산의 단관능 또는 다관능 에스테르 화합물을 포함할 수 있지만, 내화학성 측면에서 바람직하게는 2관능 이상의 다관능성 화합물일 수 있다.The polymerizable unsaturated compound is a compound which can be polymerized by the action of a photopolymerization initiator and is a monomer, an oligomer or a polymer generally used in a photosensitive resin composition, and is an acrylic acid or methacrylic acid having at least one ethylenic unsaturated double bond Functional or multifunctional ester compound, but from the viewpoint of chemical resistance, it may preferably be a multifunctional compound having two or more functional groups.
상기 중합성 불포화 화합물은 반응성 불포화 화합물로서 에틸렌글리콜디(메트)아크릴레이트, 프로필렌글리콜디(메트)아크릴레이트, 디에틸렌글리콜디(메트)아크릴레이트, 트리에틸렌글리콜디(메트)아크릴레이트, 1,6-헥산디올디(메트)아크릴레이트, 폴리에틸렌글리콜디(메트)아크릴레이트, 폴리프로필렌글리콜디(메트)아크릴레이트, 글리세린트리(메트)아크릴레이트, 트리메틸올프로판트리(메트)아크릴레이트, 펜타에리트리톨트리(메트)아크릴레이트, 펜타에리트리톨트리(메트)아크릴레이트와 숙신산의 모노에스테르화물, 펜타에리트리톨테트라(메트)아크릴레이트, 디펜타에리트리톨펜타(메트)아크릴레이트, 디펜타에리트리톨헥사(메트)아크릴레이트, 디펜타에리트리톨펜타(메트)아크릴레이트와 숙신산의 모노에스테르화물, 카프로락톤 변성 디펜타에리트리톨헥사(메트)아크릴레이트, 펜타에리트리톨트리아크릴레이트헥사메틸렌디이소시아네이트(펜타에리트리톨트리아크릴레이트와 헥사메틸렌디이소시아네이트의 반응물), 트리펜타에리트리톨헵타(메트)아크릴레이트, 트리펜타에리트리톨옥타(메트)아크릴레이트, 비스페놀 A 에폭시아크릴레이트, 및 에틸렌글리콜모노메틸에테르아크릴레이트로 이루어진 그룹으로부터 선택된 1종 이상을 사용할 수 있다. Wherein the polymerizable unsaturated compound is at least one selected from the group consisting of ethyleneglycol di (meth) acrylate, propyleneglycol di (meth) acrylate, diethyleneglycol di (meth) acrylate, triethyleneglycol di (meth) (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) Acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, pentaerythritol tri (Meth) acrylate, monoesters of dipentaerythritol penta (meth) acrylate and succinic acid, caprolactone-modified di Taerythritol hexa (meth) acrylate, pentaerythritol triacrylate hexamethylene diisocyanate (reactant of pentaerythritol triacrylate and hexamethylene diisocyanate), tripentaerythritol hepta (meth) acrylate, tripentaerytate One or more types selected from the group consisting of lititol octa (meth) acrylate, bisphenol A epoxy acrylate, and ethylene glycol monomethyl ether acrylate can be used.
또한, 이외에도 직쇄 알킬렌기 및 지환식 구조를 갖고 2개 이상의 이소시아네이트기를 갖는 화합물과, 분자 내에 1개 이상의 수산기를 갖고 3개, 4개 또는 5개의 아크릴로일옥시기 및/또는 메타크릴로일옥시기를 갖는 화합물을 반응시켜 얻어지는 다관능 우레탄아크릴레이트 화합물 등을 들 수 있다.In addition, a compound having a linear alkylene group and an alicyclic structure and having at least two isocyanate groups, and having at least one hydroxyl group in the molecule, and having three, four or five acryloyloxy groups and / or methacryloyloxy groups The polyfunctional urethane acrylate compound etc. which are obtained by making the compound which has it react are mentioned.
상업적으로 구매 가능한 상기 중합성 불포화 화합물로는, 단관능 (메트)아크릴레이트의 시판품으로서, 아로닉스 M-101, 동 M-111, 동 M-114(도아고세이(주) 제품), AKAYARAD TC-110S, 동 TC-120S(닛본가야꾸(주) 제품), V-158, V-2311(오사카유끼 가가꾸고교(주) 제품) 등이 있고, 2관능 (메트)아크릴레이트의 시판품으로서, 아로닉스 M-210, 동 M-240, 동 M-6200(도아 고세이(주) 제품), KAYARAD HDDA, 동 HX-220, 동 R-604(닛본가야꾸(주) 제품), V260, V312, V335 HP(오사카유끼 가가꾸고교(주) 제품) 등이 있으며, 3관능 이상의 (메트)아크릴레이트의 시판품으로서는 아로닉스 M-309, 동 M-400, 동 M-403, 동 M-405, 동 M-450, 동M-7100, 동 M-8030, 동 M-8060, TO-1382(도아고세이(주) 제품), KAYARAD TMPTA, 동 DPHA, 동 DPH1-40H, 동 DPC1-20, 동-30, 동-60, 동-120(닛본가야꾸(주) 제품), V-295, 동-300, 동-360, 동-GPT, 동-3PA, 동-400(오사카유끼 가가꾸고교(주) 제품) 등을 들 수 있다. 상기 중합성 불포화 화합물이 올리고머 또는 중합체로 사용되는 경우 500 내지 10,000의 중량평균분자량을 가질 수 있다. As said polymerizable unsaturated compound which can be purchased commercially, it is a commercial item of monofunctional (meth) acrylate, and it is Aronix M-101, copper M-111, copper M-114 (made by Toagosei Co., Ltd.), AKAYARAD TC- 110S, copper TC-120S (made by Nippon Kayaku Co., Ltd.), V-158, and V-2311 (made by Osaka Yuka Kagaku Kogyo Co., Ltd.), etc., are commercially available products of a bifunctional (meth) acrylate. Knicks M-210, M-240, M-6200 (manufactured by Toa Kosei Co., Ltd.), KAYARAD HDDA, HX-220, R-604 (manufactured by Nippon Kayaku Co., Ltd.), V260, V312, V335 HP (manufactured by Osaka Yuki Kagaku Kogyo Co., Ltd.), and the like, are commercially available products of trifunctional or higher (meth) acrylates such as Aronix M-309, M-400, M-403, M-405, M -450, East M-7100, East M-8030, East M-8060, TO-1382 (Toagosei Co., Ltd.), KAYARAD TMPTA, East DPHA, East DPH1-40H, East DPC1-20, East-30, Copper-60, copper-120 (product of Nippon Kayaku Co., Ltd.), V-295, copper-300, copper-360, copper-GPT, copper-3PA, copper-400 (Osaka-yu The cultivating can be a bridge Co., Ltd.) and the like. When the polymerizable unsaturated compound is used as an oligomer or a polymer, it may have a weight average molecular weight of 500 to 10,000.
상기 중합성 불포화 화합물의 함량은 알칼리 가용성 수지100 중량부(고형분 함량 기준)에 대하여 1 내지 150중량부, 바람직하게는 50 내지 120 중량부의 양으로 사용될 수 있다. 상기 범위에서 패턴 형성이 용이하며, 경화막 형성 후 경화막 표면이 거칠어지지 않으며, 현상시 하단부에 스컴(scum) 등의 패턴형상의 문제가 발생하지 않는다.
The content of the polymerizable unsaturated compound may be used in an amount of 1 to 150 parts by weight, preferably 50 to 120 parts by weight, based on 100 parts by weight of the alkali-soluble resin (based on the solid content). Pattern formation is easy in the above range, the surface of the cured film is not rough after the cured film is formed, and the problem of pattern shape such as scum at the lower end during development does not occur.
(C) (C) 광중합Light curing 개시제Initiator
본 발명에서 사용되는 광중합 개시제는 가시광선, 자외선, 원자외선, 전자선, X선 등의 방사선의 노광에 의해, 중합성 화합물의 중합을 개시할 수 있는 활성종을 발생하는 화합물이다.The photoinitiator used by this invention is a compound which produces the active species which can start superposition | polymerization of a polymeric compound by exposure of radiation, such as visible light, an ultraviolet-ray, an ultraviolet-ray, an electron beam, X-rays.
구체적으로 아세토페논계 화합물, 비이미다졸계 화합물, 트리아진계 화합물, 오늄염계 화합물, 벤조인계 화합물, 벤조페논계 화합물, 디케톤계 화합물, α-디케톤계 화합물, 다핵 퀴논계 화합물, 티오크산톤계 화합물, 디아조계 화합물, 이미드설포네이트계 화합물, 옥심계 화합물, 카바졸계 화합물, 및 설포늄 보레이트계 화합물로 이루어진 그룹으로부터 선택된 1종 이상인 것이 바람직하다. 그 중에서 대한민국 공개특허공보 제2004-0007700호, 대한민국 공개특허공보 제2005-0084149호, 대한민국 공개특허공보 제2008-0083650호, 대한민국 공개특허공보 제2008-0080208호, 대한민국 공개특허공보 제2007-0044062호, 대한민국 공개특허공보 제2007-0091110호, 대한민국 공개특허공보 제2007-0044753호, 대한민국 공개특허공보 제2009-0009991호, 대한민국 공개특허공보 제2009-0093933호, 대한민국 공개특허공보 제2010-0097658호, 대한민국 공개특허공보 제2011-0059525호, 국제공개특허공보 WO 10/102502호 및 국제공개특허공보 WO 10/133077호에 기재된 옥심계 화합물이 바람직하고, Irgacure-OXE-01, Irgacure-OXE-02(BASF사 제품), N-1919(ADEKA사 제품) 등의 시판품이 고감도, 해상도의 면에서 바람직하다. 이중에서도 카르바졸 옥심계 개시제가 특히 바람직하다.Specifically, acetophenone compound, biimidazole compound, triazine compound, onium salt compound, benzoin compound, benzophenone compound, diketone compound, α-diketone compound, polynuclear quinone compound, thioxanthone compound It is preferable that it is at least 1 type selected from the group which consists of a diazo type compound, an imide sulfonate type compound, an oxime type compound, a carbazole type compound, and a sulfonium borate type compound. Among them, Republic of Korea Patent Publication No. 2004-0007700, Republic of Korea Patent Publication No. 2005-0084149, Republic of Korea Patent Publication No. 2008-0083650, Republic of Korea Patent Publication No. 2008-0080208, Republic of Korea Patent Publication No. 2007-0044062 Republic of Korea Patent Publication No. 2007-0091110, Republic of Korea Patent Publication No. 2007-0044753, Republic of Korea Patent Publication No. 2009-0009991, Republic of Korea Patent Publication No. 2009-0093933, Republic of Korea Patent Publication No. 2010-0097658 The oxime compounds described in Korean Patent Application Laid-Open No. 2011-0059525, WO 10/102502 and WO 10/133077 are preferred, and Irgacure-OXE-01, Irgacure-OXE- Commercial items, such as 02 (made by BASF Corporation) and N-1919 (made by ADEKA Corporation), are preferable at the point of high sensitivity and resolution. Of these, carbazole oxime initiators are particularly preferred.
상기 광중합 개시제의 함량은 알칼리 가용성 수지 100 중량부(고형분 함량 기준)에 대하여 0.1 내지 20중량부, 바람직하게는 3 내지 17 중량부의 양으로 사용될 수 있다. 중합 개시제의 함량이 상기의 범위이면 노광에 의한 경화가 충분히 이루어져 유기 절연막의 패턴을 얻기 용이하며, 유기 절연막이 하부 층과 충분히 밀착되는 장점이 있다.
The content of the photopolymerization initiator may be used in an amount of 0.1 to 20 parts by weight, preferably 3 to 17 parts by weight, based on 100 parts by weight of the alkali-soluble resin (based on the solid content). When the content of the polymerization initiator is in the above range, curing by exposure is sufficiently performed to obtain a pattern of the organic insulating film, and the organic insulating film has an advantage of being in close contact with the lower layer.
(D) 용매(D) Solvent
본 발명의 감광성 수지 조성물은 상기한 성분들을 용매와 혼합하여 액상 조성물로서 제조하는 것이 바람직하다. 사용되는 용매로는 상술한 감광성 수지 조성물 성분들과 상용성을 가지되, 이들과 반응하지 않는 것으로, 감광성 수지 조성물에 사용되는 공지의 용매이면 어느 것이나 사용 가능하다.The photosensitive resin composition of the present invention is preferably prepared as a liquid composition by mixing the above components with a solvent. The solvent to be used is compatible with the above-mentioned photosensitive resin composition components and does not react with them. Any known solvent used in the photosensitive resin composition can be used.
이러한 용매의 예로는 에틸렌글리콜모노메틸에테르아세테이트, 에틸렌글리콜모노에틸에테르아세테이트 등의 에틸렌글리콜모노알킬에테르아세테이트류; 프로필렌글리콜모노메틸에테르, 프로필렌글리콜모노에틸에테르, 프로필렌글리콜모노프로필에테르, 프로필렌글리콜모노부틸에테르 등의 프로필렌글리콜모노알킬에테르류; 프로필렌글리콜디메틸에테르, 프로필렌글리콜디에틸에테르, 프로필렌글리콜디프로필에테르, 프로필렌글리콜디부틸에테르 등의 프로필렌글리콜디알킬에테르류; 디프로필렌글리콜디메틸에테르 등의 디프로필렌글리콜디알킬에테르류; 프로필렌글리콜모노메틸에테르아세테이트, 프로필렌글리콜모노에틸에테르아세테이트, 프로필렌글리콜모노프로필에테르아세테이트, 프로필렌글리콜모노부틸에테르아세테이트 등의 프로필렌글리콜모노알킬에테르아세테이트류; 에틸셀로솔브, 부틸셀로솔브 등의 셀로솔브류; 부틸카르비톨 등의 카르비톨류; 락트산 메틸, 락트산 에틸, 락트산 n-프로필, 락트산 이소프로필 등의 락트산 에스테르류; 아세트산 에틸, 아세트산 n-프로필, 아세트산 이소프로필, 아세트산 n-부틸, 아세트산 이소부틸, 아세트산 n-아밀, 아세트산 이소아밀, 프로피온산 이소프로필, 프로피온산 n-부틸, 프로피온산 이소부틸 등의 지방족 카복실산 에스테르류; 3-메톡시프로피온산메틸, 3-메톡시프로피온산에틸, 3-에톡시프로피온산메틸, 3-에톡시프로피온산에틸, 피루브산메틸, 피루브산에틸 등의 에스테르류; 톨루엔, 크실렌 등의 방향족 탄화수소류; 2-헵타논, 3-헵타논, 4-헵타논, 시클로헥사논 등의 케톤류; N-디메틸포름아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈 등의 아미드류; γ-부티로락톤 등의 락톤류; 및 이들의 혼합물을 들 수 있다. 상기 용매는 단독으로 또는 2종 이상을 배합하여 사용할 수 있다.Examples of such a solvent include ethylene glycol monoalkyl ether acetates such as ethylene glycol monomethyl ether acetate and ethylene glycol monoethyl ether acetate; Propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monopropyl ether and propylene glycol monobutyl ether; Propylene glycol dialkyl ethers such as propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol dipropyl ether and propylene glycol dibutyl ether; Dipropylene glycol dialkyl ethers such as dipropylene glycol dimethyl ether; Propylene glycol monoalkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate and propylene glycol monobutyl ether acetate; Cellosolve such as ethyl cellosolve and butyl cellosolve; Carbitols such as butyl carbitol; Lactic acid esters such as methyl lactate, ethyl lactate, n-propyl lactate, and isopropyl lactate; Aliphatic carboxylic acid esters such as ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl acetate, isoamyl acetate, isopropyl propionate, n-butyl propionate and isobutyl propionate; Esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl pyruvate and ethyl pyruvate; Aromatic hydrocarbons such as toluene and xylene; 2-heptanone, 3-heptanone, 4-heptanone, and cyclohexanone; Amides such as N-dimethylformamide, N-methylacetamide, N, N-dimethylacetamide and N-methylpyrrolidone; lactones such as? -butyrolactone; And mixtures thereof. These solvents may be used alone or in combination of two or more.
본 발명에 따른 감광성 수지 조성물에 있어서, 상기 용매의 함유량은 특별히 한정되지 않지만, 얻어지는 감광성 수지 조성물의 도포성, 안정성 등의 관점에서, 조성물 총 중량을 기준으로 고형분 함량이 5 내지 70 중량%, 바람직하게는 10 내지 55중량%가 되도록 유기용매를 포함할 수 있다. In the photosensitive resin composition according to the present invention, the content of the solvent is not particularly limited, but the solid content is 5 to 70% by weight, based on the total weight of the composition, from the viewpoints of coating properties, stability and the like of the obtained photosensitive resin composition. Preferably it may include an organic solvent to 10 to 55% by weight.
여기서, 상기 고형분이란 본 발명의 조성물에서 용매를 제거한 것을 의미한다.
Here, the solid content means that the solvent is removed from the composition of the present invention.
(E) 추가의 성분 (E) Additional Ingredients
본 발명의 감광성 수지 조성물은 상기 성분 (A) 내지 (D) 이외에, 필요에 따라, 조성물의 성능을 저해하지 않는 범위내에서 알칼리 가용성 수지 100 중량부(고형분 함량 기준)에 대하여 0.001 내지 10중량부, 바람직하게는 0.05 내지 5중량부의 양으로 추가의 성분을 포함할 수 있으며, 이러한 추가의 성분으로는 예를 들어 다음과 같은 성분이 있다.0.001-10 weight part of the photosensitive resin composition of this invention with respect to 100 weight part (solid content basis) of alkali-soluble resin in the range which does not impair the performance of a composition other than the said components (A)-(D) as needed. , Preferably in an amount of 0.05 to 5 parts by weight, and may include additional components, such as, for example, the following components.
(e-1) 광 안정제(e-1) light stabilizer
본 발명의 감광성 수지 조성물은 광 안정제를 추가로 함유할 수 있다. 이러한 광 안정제로는 자외선 흡수제나 장애 아민계 광 안정제를 들 수 있다. The photosensitive resin composition of this invention can contain a light stabilizer further. Such light stabilizers include ultraviolet absorbers and hindered amine light stabilizers.
상기 자외선 흡수제로서는 벤조트리아졸계, 벤조페논계, 트리아진계, 옥살릭 아닐리드계, 피리미딘계, 살리실릭계 등을 사용할 수 있으나, 이에 한정되는 것은 아니다. 2-(2-히드록시-3-t-부틸-5-메틸페닐)-5-클로로벤조트리아졸 등의 벤조트리아졸계 또는 2,4-비스(2,4-디메틸페닐)-6-(2-히드록시-4-이소옥틸옥시페닐)-1,3,5-트리아진 등의 트리아진 유도체가 바람직하다. The ultraviolet absorber may be benzotriazole, benzophenone, triazine, oxalic anilide, pyrimidine, salicylic, and the like, but is not limited thereto. Benzotriazoles such as 2- (2-hydroxy-3-t-butyl-5-methylphenyl) -5-chlorobenzotriazole or 2,4-bis (2,4-dimethylphenyl) -6- (2- Triazine derivatives, such as hydroxy-4-isooctyloxyphenyl) -1,3,5-triazine, are preferable.
상기 장애 아민계 광 안정제는 분자량 250 이상이고 4-위치에 치환기를 가지는 2,2,6,6-테트라알킬피페리딘 유도체이고, 그의 4-위치의 치환기로서는 예를 들어 카르복시 그룹, 알콕시 그룹, 알킬아미노 그룹, 히드록시 그룹 등을 들 수 있다. 또한, N-위치에는 알킬 그룹, 아실 그룹이 치환되어 있어도 좋다. 예를 들어, 비스(2,2,6,6-테트라메틸-4-피페리디닐)세바케이트, 2,2,6,6-테트라메틸피페리디닐스테아레이트, 폴리[[6-[(1,1,3,3-테트라메틸부틸)아미노]-1,3,5-트리아진-2,4-디일][(2,2,6,6-테트라메틸-4-피페리디닐)이미노]-1,6-헥산디일[(2,2,6,6-테트라메틸-4-피페리디닐)이미노]] 등을 사용할 수 있다.The hindered amine light stabilizer is a 2,2,6,6-tetraalkylpiperidine derivative having a molecular weight of 250 or more and a substituent at the 4-position, and examples of the 4-position substituent include a carboxy group, an alkoxy group, Alkylamino group, a hydroxy group, etc. are mentioned. In addition, an alkyl group and an acyl group may be substituted in the N-position. For example, bis (2,2,6,6-tetramethyl-4-piperidinyl) sebacate, 2,2,6,6-tetramethylpiperidinylstearate, poly [[6-[(1 , 1,3,3-tetramethylbutyl) amino] -1,3,5-triazine-2,4-diyl] [(2,2,6,6-tetramethyl-4-piperidinyl) imino ] -1,6-hexanediyl [(2,2,6,6-tetramethyl-4-piperidinyl) imino]] and the like can be used.
상기 자외선 흡수제와 장애 아민계 광 안정제는 내광성 및 패턴 형상 특성을 향상시키기 위해 함께 사용할 수도 있다. The ultraviolet absorber and the hindered amine light stabilizer may be used together to improve light resistance and pattern shape characteristics.
(e-2) 계면 활성제(e-2) surfactant
본 발명의 감광성 수지 조성물은 도포성, 거품방지성, 레벨링성 등을 향상시킬 목적으로 계면활성제를 추가로 함유할 수 있다. 상기 계면활성제의 종류는 특별히 한정하지 않으나, 불소계 계면활성제, 실리콘계 계면활성제인 것이 바람직하다. 상기 실리콘계 계면활성제의 시판품으로서 다우코닝 도레이 실리콘사의 DC3PA, DC7PA, SH11PA, SH21PA, SH8400 등이 있고, GE 도시바 실리콘사의 TSF-4440, TSF-4300, TSF-4445, TSF-4446, TSF-4460, TSF-4452 등, BYK사의 BYK 333 등, 다우코닝도레이 실리콘사의 FZ-2100, FZ-2110, FZ-2222, FZ-2233등이 있다. 상기 불소계 계면활성제는 예를 들면 시판품으로서 다이닛본 잉크 가가꾸 고교사의 메가피스 F-470, F-471, F-475, F-482, F-489 등이 있다. 이중에서 BYK사의 BYK 333가 분산성의 면에서 바람직하다. 이들은 단독으로 또는 2종 이상을 조합하여 사용할 수 있다.The photosensitive resin composition of this invention can contain surfactant further for the purpose of improving applicability | paintability, antifoaming property, leveling property, etc. Although the kind of said surfactant is not specifically limited, It is preferable that they are a fluorine-type surfactant and a silicone type surfactant. Commercially available silicone-based surfactants include Dow Corning Toray Silicone Co., Ltd., DC3PA, DC7PA, SH11PA, SH21PA, SH8400 and the like. GE Toshiba Silicone Co., Ltd. -BYK 333, BYK 333, etc., FZ-2100, FZ-2110, FZ-2222, FZ-2233 from Dow Corning Toray Silicone. Examples of the fluorine-based surfactant include Megapis F-470, F-471, F-475, F-482 and F-489 commercially available from Dainippon Ink and Chemicals, Incorporated. Of these, BYK 333 from BYK is preferred in view of dispersibility. These can be used individually or in combination of 2 or more types.
(e-3) (e-3) 실란Silane 커플링제Coupling agent
본 발명의 감광성 수지 조성물은 기판과의 접착성을 향상시키기 위해 카복실기, (메트)아크릴로일기, 이소시아네이트기, 아미노기, 머캅토기, 비닐기 및 에폭시기로 이루어진 그룹으로부터 선택된 1종 이상의 반응성 치환기를 갖는 실란 커플링제를 추가로 포함할 수 있다. The photosensitive resin composition of the present invention has at least one reactive substituent selected from the group consisting of a carboxyl group, a (meth) acryloyl group, an isocyanate group, an amino group, a mercapto group, a vinyl group and an epoxy group in order to improve adhesion to the substrate. It may further comprise a silane coupling agent.
상기 실란 커플링제의 종류는 특별히 한정하지 않으나, 트리메톡시실릴벤조산, γ-메타크릴옥시프로필트리메톡시실란, 비닐트리아세톡시실란, 비닐트리메톡시실란, γ-이소시아네이토프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γ-글리시독시프로필트리에톡시실란, 및 β-(3,4-에폭시시클로헥실)에틸트리메톡시실란으로 이루어진 그룹으로부터 선택된 1종 이상을 사용하는 것이 바람직하다. 이 중에서 내화학성을 유지하면서 기판과의 접착성이 좋은 이소시아네이트기를 갖는 것이 바람직하며, 예를 들면 γ-이소시아네이트프로필트리에톡시실란(Shin-Etsu사의 KBE-9007)이 있다. Although the kind of the said silane coupling agent is not specifically limited, Trimethoxy silyl benzoic acid, (gamma)-methacryloxypropyl trimethoxysilane, vinyl triacetoxysilane, vinyl trimethoxysilane, (gamma)-isocyanatopropyl trie One or more selected from the group consisting of oxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, and β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane Preference is given to using. Among these, it is preferable to have an isocyanate group having good adhesion to the substrate while maintaining chemical resistance, and for example, γ-isocyanate propyltriethoxysilane (KBE-9007 from Shin-Etsu) is available.
상기 언급된 추가의 성분 이외에도, 본 발명에 따른 상기 감광성 수지 조성물은 분산제, 산화방지제, 열중합 방지제, 레벨링제, 광가교 증감제, 경화촉진제 및 용해속도 조절제로 이루어진 그룹으로부터 선택된 1 종 이상의 첨가제를 추가로 포함할 수 있다.
In addition to the above-mentioned additional components, the photosensitive resin composition according to the present invention may contain at least one additive selected from the group consisting of a dispersant, an antioxidant, a thermal polymerization inhibitor, a leveling agent, a photocrosslinking sensitizer, a curing accelerator, and a dissolution rate controlling agent. It may further comprise.
본 발명에 따른 감광성 수지 조성물은 당업계에 공지된 통상의 방법에 따라 기판에 도포, 노광 및 현상함으로써 유기 절연막을 형성할 수 있다. 상기 도포 방법으로는 예를 들어 스프레이 법, 롤 도포법 및 회전 도포법을 사용할 수 있고, 노광에 사용되는 광원으로는 저압 수은등, 고압 수은등, 초고압 수은등, 금속 할로겐화물 램프, 아르곤 가스 레이저 등을 사용할 수 있으며, 경우에 따라 X선, 전자선 등도 이용할 수 있다. 노광량은 조성물 각 성분의 종류, 배합량 및 건조 막 두께에 따라 다르지만, 고압 수은등을 사용하는 경우에는 500mJ/㎠(365nm 파장) 이하이다. 현상에 사용되는 현상액으로는 탄산나트륨, 수산화나트륨, 수산화칼륨, 테트라메틸암모늄히드록시드 등의 알칼리성 수용액을 사용할 수 있다.
The photosensitive resin composition which concerns on this invention can form an organic insulating film by apply | coating, exposing, and developing to a board | substrate according to the conventional method known in the art. As the coating method, for example, a spray method, a roll coating method, and a rotary coating method may be used. As a light source used for exposure, a low pressure mercury lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, an argon gas laser, or the like may be used. In some cases, X-rays, electron beams, and the like may also be used. Although an exposure amount changes with the kind of each component, compounding quantity, and dry film thickness of a composition, when using a high pressure mercury lamp, it is 500 mJ / cm <2> (365 nm wavelength) or less. As a developing solution used for image development, alkaline aqueous solution, such as sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, can be used.
이하, 본 발명의 이해를 돕기 위하여 합성예 및 실시예를 예시하여 설명한다. 하기 합성예 기재된 중량평균분자량은 겔 투과 크로마토그래피(GPC)에 의해 측정한 폴리스티렌 환산값이다.Hereinafter, the synthesis examples and examples will be described to help understand the present invention. The weight average molecular weight described in the following synthesis example is a polystyrene conversion value measured by gel permeation chromatography (GPC).
합성예Synthetic example 1 One
건조관이 달린 냉각관, 스터러 및 온도 자동조절기가 달린 삼구 플라스크에 옥틸메캅탄 3중량부, 2,2'-아조비스(2,4-디메틸발레로니트닐) 2중량부, 프로필렌글리콜모노메틸에테르아세테이트 100중량부, o-히드록시페닐메타크릴레이트 35중량부, 스티렌 35중량부 및 글리시딜메타크릴레이트 30중량부를 넣고 질소를 투입한 후, 서서히 교반하면서 용액의 온도를 60℃로 상승시키고 이 온도를 5 시간 유지하며 중합시켜 알칼리 가용성 수지(중량평균분자량(Mw): 9,800)를 합성하였다.3 parts by weight of octyl mecaptan, 2 parts by weight of 2,2'-azobis (2,4-dimethylvaleronitrile) in a three-necked flask with a drying tube, a stirrer and a thermostat, propylene glycol mono 100 parts by weight of methyl ether acetate, 35 parts by weight of o-hydroxyphenyl methacrylate, 35 parts by weight of styrene and 30 parts by weight of glycidyl methacrylate were added thereto, nitrogen was added thereto, and the solution was gradually stirred to 60 ° C. The alkali soluble resin (weight average molecular weight (Mw): 9,800) was synthesized by increasing the temperature and maintaining the temperature for 5 hours.
합성예Synthetic example 2 내지 7 2 to 7
하기 표 1에 기재된 화합물 및 합성예 2, 4의 숙성 온도를 65℃로 사용한 것을 제외하고는 상기 합성예 1과 동일한 방법으로 알칼리 가용성 수지를 합성하였다.Alkali-soluble resins were synthesized in the same manner as in Synthesis Example 1, except that the compounds shown in Table 1 and the aging temperatures of Synthesis Examples 2 and 4 were used at 65 ° C.
[표 1][Table 1]
실시예Example 1 One
합성예 1에 따른 알칼리 가용성 수지 12중량부(고형분 함량), 디펜타에리트리톨헥사아크릴레이트(상품명 DPHA, Nippon Kayaku사) 10중량부(고형분 함량), Irgacure-OXE-02(BASF 사) 1중량부(고형분 함량) 및 프로필렌글리콜모노메틸에테르아세테이트 77중량부를 쉐이커(shaker)를 이용하여 2시간 혼합하여 감광성 수지 조성물을 제조하였다.
12 parts by weight of an alkali-soluble resin (solid content) according to Synthesis Example 1, 10 parts by weight (solid content) of dipentaerythritol hexaacrylate (trade name DPHA, Nippon Kayaku), and 1 part of Irgacure-OXE-02 (BASF) Part (solid content) and 77 parts by weight of propylene glycol monomethyl ether acetate were mixed for 2 hours using a shaker to prepare a photosensitive resin composition.
실시예Example 2 내지 2 to 실시예Example 12 및 12 and 비교예Comparative Example 1 내지 1 to 비교예Comparative Example 7 7
하기 표 2에 기재된 바와 같이 성분 내지는 성분들의 함량을 변화시킨 것을 제외하고는, 상기 실시예 1과 동일한 공정을 수행하여 감광성 수지 조성물을 제조하였다.Except for changing the content of the components or components as shown in Table 2, was carried out the same process as in Example 1 to prepare a photosensitive resin composition.
[표 2][Table 2]
시험예Test Example
상기 실시예 및 비교예에 따라 감광성 수지 조성물 및 상기 감광성 수지 조성물로부터 형성된 경화막의 물성을 하기와 같이 평가하고, 그 결과를 표 3에 나타내었다.According to the said Example and the comparative example, the physical property of the photosensitive resin composition and the cured film formed from the said photosensitive resin composition was evaluated as follows, and the result is shown in Table 3.
1) 보관 안정성 (점도변화)1) Storage stability (viscosity change)
감광성 수지 조성물 10 g을 20 ㎖ 유리 바이알 병에 넣고 40℃에서 24 시간 보관한 후 점도의 상승 정도(%)를 측정하였다. 점도는 TOKI SANGYO 사의 TV-22 회전식 점도계를 이용하여 측정하였다. 점도 측정 방법은 1㎖ 시료를 채취하여 점도 측정기에 담아 온도가 25℃로 안정화된 후에 점도 측정기의 스핀들에 걸리는 압력을 이용하여 점도를 측정한다. 상승 정도(%)가 5% 이하이면 우수, 3% 이하이면 매우 우수하다고 할 수 있다.10 g of the photosensitive resin composition was placed in a 20 ml glass vial bottle, and stored at 40 ° C. for 24 hours to measure the degree of increase of the viscosity (%). The viscosity was measured using the TV-22 rotary viscometer of TOKI SANGYO. Viscosity measurement method is to take a 1ml sample, put it in a viscosity meter and stabilize the viscosity using the pressure applied to the spindle of the viscosity meter after the temperature is stabilized to 25 ℃. If the degree of increase (%) is 5% or less, it can be said to be excellent.
2) 2) 부착성Adhesion (최소 잔류 라인 패턴)(Minimum residual line pattern)
감광성 수지 조성물을 유리 기판 상에 3 ㎛ 두께로 회전 도포한 후 110℃에서 100 초간 예비베이크(prebake)하였다. 1 ㎛ ~ 30 ㎛까지 1 ㎛ 간격으로 라인 패턴이 6개씩 있는 포토 마스크를 개재하여 상기 도포막에 5mJ/㎠(365 nm의 파장)로 노광한 후, 2.38중량% 테트라메틸암모늄히드록시드(TMAH) 알칼리 수용액으로 100 초간 현상하였다. 탈이온수를 20 초간 분사하여 씻어내고 건조시킨 후 기판에 남아있는 라인 패턴의 최소 사이즈(㎛)를 측정하였다. 사이즈가 작을 수록 부착성은 양호하다고 할 수 있따.The photosensitive resin composition was spun onto a glass substrate with a thickness of 3 μm and then prebaked at 110 ° C. for 100 seconds. 2.38% by weight of tetramethylammonium hydroxide (TMAH) after exposure to the coating film at 5 mJ / cm 2 (wavelength of 365 nm) through photo masks having six line patterns at intervals of 1 μm to 30 μm at 1 μm intervals. ) Developed for 100 seconds with aqueous alkali solution. Deionized water was sprayed for 20 seconds, washed, and dried to measure the minimum size (µm) of the line pattern remaining on the substrate. The smaller the size, the better the adhesion.
3) 내열성3) heat resistance
감광성 수지 조성물을 유리 기판 상에 3 ㎛ 두께로 회전 도포한 후 110℃에서 100 초간 예비베이크(prebake)하였다. 상기 도포막을 30mJ/㎠(365 nm의 파장)로 노광한 후, 2.38% TMAH 알칼리 수용액으로 100 초간 현상하였다. 탈이온수를 20 초간 분사하여 씻어낸 후, 230℃ 오븐 속에 1 시간 포스트베이크(postbake)하였다. 이후, 기판 위의 경화막을 3 ㎎ 채취하여 TGA(Thermo-Gravimetric Analysis) 장치에 넣고 상온에서 300℃까지 분당 10℃로 온도를 상승하여 무게의 감소 정도를 중량으로 측정하여 %로 분석하였다. 손실량이 적을수록 내열성이 우수하다.The photosensitive resin composition was spun onto a glass substrate with a thickness of 3 μm and then prebaked at 110 ° C. for 100 seconds. The coating film was exposed at 30 mJ / cm 2 (wavelength of 365 nm) and then developed for 100 seconds with a 2.38% TMAH alkali aqueous solution. Deionized water was sprayed for 20 seconds to rinse off and post-baked for 1 hour in a 230 ° C. oven. Thereafter, 3 mg of the cured film on the substrate was collected and placed in a TGA (Thermo-Gravimetric Analysis) apparatus, and the temperature was increased to 10 ° C. per minute from room temperature to 300 ° C., and the weight loss was measured by weight and analyzed in%. The smaller the loss, the better the heat resistance.
[표 3][Table 3]
상기 표 3에 나타난 바와 같이, 본 발명에 따른 알칼리 가용성 수지를 사용하여 제조된 실시예 1 내지 12의 감광성 수지 조성물은 페놀기를 포함하는 에틸렌성 불포화 화합물로부터 유래되는 구성 단위를 포함하지 않는 알칼리 가용성 수지를 사용하여 제조된 비교예 1 내지 7의 감광성 수지 조성물에 비하여 보관 안정성이 우수하고, 부착성 및 내열성이 우수한 막을 제공할 수 있었다. As shown in Table 3, the photosensitive resin compositions of Examples 1 to 12 prepared using the alkali-soluble resin according to the present invention do not contain a structural unit derived from an ethylenically unsaturated compound containing a phenol group. Compared with the photosensitive resin compositions of Comparative Examples 1 to 7 prepared using, it was possible to provide a film having excellent storage stability and excellent adhesion and heat resistance.
Claims (6)
(B) 하나 이상의 에틸렌성 불포화 결합을 포함하는 중합성 화합물;
(C) 광중합 개시제; 및
(D) 용매를 함유하는 감광성 수지 조성물.(A) (a-1) Structural unit derived from ethylenically unsaturated compound containing a phenol group; (a-2) Structural unit derived from the ethylenically unsaturated compound containing one or more epoxy groups; And (a-3) Alkali-soluble resin which contains the structural unit derived from a styrene-type unsaturated compound and does not contain a carboxyl group;
(B) a polymerizable compound comprising at least one ethylenically unsaturated bond;
(C) photoinitiator; And
(D) Photosensitive resin composition containing a solvent.
[화학식 1]
상기 화학식 1에서, R1은 단일 결합 또는 C1-C10 알킬렌기이고, R2는 수소 원자 또는 C1-C6 알킬기이다.The ethylenically unsaturated compound containing the phenol group of the said structural unit (a-1) is represented by following General formula (1), The photosensitive resin composition of Claim 1 characterized by the above-mentioned.
[Formula 1]
In Formula 1, R 1 is a single bond or a C 1 -C 10 alkylene group, R 2 is a hydrogen atom or a C 1 -C 6 alkyl group.
[화학식 2]
상기 화학식 2에서, R3은 수소 원자 또는 C1-C2 알킬기이고, R4는 단일 결합 또는 C1-C10 알킬렌기이고, R5는 수소 원자 또는 C1-C6 알킬기이다.The ethylenically unsaturated compound containing one or more epoxy groups of the said structural unit (a-2) is represented by following General formula (2), The photosensitive resin composition of Claim 1 characterized by the above-mentioned.
(2)
In Formula 2, R 3 is a hydrogen atom or a C 1 -C 2 alkyl group, R 4 is a single bond or a C 1 -C 10 alkylene group, R 5 is a hydrogen atom or a C 1 -C 6 alkyl group.
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| KR20160035515A (en) * | 2014-09-23 | 2016-03-31 | 동우 화인켐 주식회사 | Photosensitive resin composition |
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