KR101249681B1 - binder resin and photosensitive resin composition comprising the same and column Spacer made by the photosensitive resin composition - Google Patents
binder resin and photosensitive resin composition comprising the same and column Spacer made by the photosensitive resin composition Download PDFInfo
- Publication number
- KR101249681B1 KR101249681B1 KR1020080007171A KR20080007171A KR101249681B1 KR 101249681 B1 KR101249681 B1 KR 101249681B1 KR 1020080007171 A KR1020080007171 A KR 1020080007171A KR 20080007171 A KR20080007171 A KR 20080007171A KR 101249681 B1 KR101249681 B1 KR 101249681B1
- Authority
- KR
- South Korea
- Prior art keywords
- acrylate
- meth
- methyl
- ethyl
- acid
- 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.)
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- 239000011347 resin Substances 0.000 title claims abstract description 41
- 229920005989 resin Polymers 0.000 title claims abstract description 41
- 239000011230 binding agent Substances 0.000 title claims abstract description 40
- 239000011342 resin composition Substances 0.000 title claims description 23
- 125000006850 spacer group Chemical group 0.000 title claims description 6
- 239000000203 mixture Substances 0.000 claims abstract description 19
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 94
- -1 aliphatic carbon compound Chemical class 0.000 claims description 51
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 30
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 12
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003999 initiator Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 6
- IUTPJBLLJJNPAJ-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)propanoic acid Chemical compound OC(=O)CCN1C(=O)C=CC1=O IUTPJBLLJJNPAJ-UHFFFAOYSA-N 0.000 claims description 6
- OWVMFLLVLFONOO-UHFFFAOYSA-N 3-butoxypropanoic acid Chemical compound CCCCOCCC(O)=O OWVMFLLVLFONOO-UHFFFAOYSA-N 0.000 claims description 6
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 6
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 claims description 6
- 239000002202 Polyethylene glycol Substances 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 6
- 229940116333 ethyl lactate Drugs 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 6
- 229920001223 polyethylene glycol Polymers 0.000 claims description 6
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 5
- 150000001923 cyclic compounds Chemical class 0.000 claims description 5
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N acrylic acid methyl ester Natural products COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 4
- LXSVWFRZICUOLU-ZCFIWIBFSA-N (2r)-2-butoxypropanoic acid Chemical compound CCCCO[C@H](C)C(O)=O LXSVWFRZICUOLU-ZCFIWIBFSA-N 0.000 claims description 3
- ZGJREYUOKJFGAP-UHFFFAOYSA-N 1,3,5-tris(trichloromethyl)-1,3,5-triazinane Chemical compound ClC(Cl)(Cl)N1CN(C(Cl)(Cl)Cl)CN(C(Cl)(Cl)Cl)C1 ZGJREYUOKJFGAP-UHFFFAOYSA-N 0.000 claims description 3
- IRHDNBHTFQNBKA-UHFFFAOYSA-N 1,3-bis(2,3,4-trichlorophenyl)-2,4-dihydro-1,3,5-triazine Chemical compound ClC1=C(Cl)C(Cl)=CC=C1N1CN(C=2C(=C(Cl)C(Cl)=CC=2)Cl)C=NC1 IRHDNBHTFQNBKA-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 claims description 3
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 claims description 3
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 claims description 3
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 claims description 3
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 claims description 3
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 claims description 3
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 claims description 3
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 claims description 3
- HLIQLHSBZXDKLV-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-phenoxyethanol Chemical compound OCCOCC(O)OC1=CC=CC=C1 HLIQLHSBZXDKLV-UHFFFAOYSA-N 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- MUUOUUYKIVSIAR-UHFFFAOYSA-N 2-but-3-enyloxirane Chemical compound C=CCCC1CO1 MUUOUUYKIVSIAR-UHFFFAOYSA-N 0.000 claims description 3
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 3
- XBHQOMRKOUANQQ-UHFFFAOYSA-N 2-ethoxypropanoic acid Chemical compound CCOC(C)C(O)=O XBHQOMRKOUANQQ-UHFFFAOYSA-N 0.000 claims description 3
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
- FCZHJHKCOZGQJZ-UHFFFAOYSA-N 2-oct-7-enyloxirane Chemical compound C=CCCCCCCC1CO1 FCZHJHKCOZGQJZ-UHFFFAOYSA-N 0.000 claims description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 3
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 claims description 3
- UNDXPKDBFOOQFC-UHFFFAOYSA-N 4-[2-nitro-4-(trifluoromethyl)phenyl]morpholine Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=CC=C1N1CCOCC1 UNDXPKDBFOOQFC-UHFFFAOYSA-N 0.000 claims description 3
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims description 3
- KXXLCMPSLFIEEH-UHFFFAOYSA-N 4h-naphthalene-1,3-dione Chemical compound C1=CC=C2CC(=O)CC(=O)C2=C1 KXXLCMPSLFIEEH-UHFFFAOYSA-N 0.000 claims description 3
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 3
- GXBYFVGCMPJVJX-UHFFFAOYSA-N Epoxybutene Chemical compound C=CC1CO1 GXBYFVGCMPJVJX-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 claims description 3
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 claims description 3
- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims description 3
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 claims description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 3
- 239000012965 benzophenone Substances 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 claims description 3
- VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 claims description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 3
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 claims description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 3
- 229940119545 isobornyl methacrylate Drugs 0.000 claims description 3
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 3
- VNKYTQGIUYNRMY-UHFFFAOYSA-N methoxypropane Chemical compound CCCOC VNKYTQGIUYNRMY-UHFFFAOYSA-N 0.000 claims description 3
- 150000004702 methyl esters Chemical class 0.000 claims description 3
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 claims description 3
- YBCIDCSDCILTTE-UHFFFAOYSA-N oxiran-2-ylmethyl bicyclo[2.2.1]hept-2-ene-5-carboxylate Chemical compound C1C(C=C2)CC2C1C(=O)OCC1CO1 YBCIDCSDCILTTE-UHFFFAOYSA-N 0.000 claims description 3
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 claims description 3
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 3
- MBDNRNMVTZADMQ-UHFFFAOYSA-N sulfolene Chemical compound O=S1(=O)CC=CC1 MBDNRNMVTZADMQ-UHFFFAOYSA-N 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims description 3
- DWWMSEANWMWMCB-UHFFFAOYSA-N tribromomethylsulfonylbenzene Chemical compound BrC(Br)(Br)S(=O)(=O)C1=CC=CC=C1 DWWMSEANWMWMCB-UHFFFAOYSA-N 0.000 claims description 3
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 claims description 3
- GZZRDBYXGPSMCR-UHFFFAOYSA-N 1-(2-chlorophenyl)-3,5-bis(trichloromethyl)-1,3,5-triazinane Chemical compound ClC1=CC=CC=C1N1CN(C(Cl)(Cl)Cl)CN(C(Cl)(Cl)Cl)C1 GZZRDBYXGPSMCR-UHFFFAOYSA-N 0.000 claims description 2
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 claims description 2
- LZHUBCULTHIFNO-UHFFFAOYSA-N 2,4-dihydroxy-1,5-bis[4-(2-hydroxyethoxy)phenyl]-2,4-dimethylpentan-3-one Chemical compound C=1C=C(OCCO)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCO)C=C1 LZHUBCULTHIFNO-UHFFFAOYSA-N 0.000 claims description 2
- SGUYGLMQEOSQTH-UHFFFAOYSA-N 2-propoxyacetic acid Chemical compound CCCOCC(O)=O SGUYGLMQEOSQTH-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- 239000007983 Tris buffer Substances 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- YEWZQCDRZRYAEB-UHFFFAOYSA-N ditert-butyl hydrogen phosphate Chemical compound CC(C)(C)OP(O)(=O)OC(C)(C)C YEWZQCDRZRYAEB-UHFFFAOYSA-N 0.000 claims description 2
- 229960004275 glycolic acid Drugs 0.000 claims description 2
- 239000004816 latex Substances 0.000 claims description 2
- 229920000126 latex Polymers 0.000 claims description 2
- AZOJAKKTOVKBTB-UHFFFAOYSA-N methyl 4-(dimethylamino)-2-methylidenebutanoate Chemical compound COC(=O)C(=C)CCN(C)C AZOJAKKTOVKBTB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims 1
- 229920001451 polypropylene glycol Polymers 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 description 9
- 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 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920002120 photoresistant polymer Polymers 0.000 description 4
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- YEKDUBMGZZTUDY-UHFFFAOYSA-N 1-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)N1C(=O)C=CC1=O YEKDUBMGZZTUDY-UHFFFAOYSA-N 0.000 description 2
- NMMXJQKTXREVGN-UHFFFAOYSA-N 2-(4-benzoyl-3-hydroxyphenoxy)ethyl prop-2-enoate Chemical compound OC1=CC(OCCOC(=O)C=C)=CC=C1C(=O)C1=CC=CC=C1 NMMXJQKTXREVGN-UHFFFAOYSA-N 0.000 description 2
- 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 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-VAWYXSNFSA-N AIBN Substances N#CC(C)(C)\N=N\C(C)(C)C#N OZAIFHULBGXAKX-VAWYXSNFSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- 229940113165 trimethylolpropane Drugs 0.000 description 2
- DXUMYHZTYVPBEZ-UHFFFAOYSA-N 2,4,6-tris(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 DXUMYHZTYVPBEZ-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
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ICPWFHKNYYRBSZ-UHFFFAOYSA-N 2-methoxypropanoic acid Chemical compound COC(C)C(O)=O ICPWFHKNYYRBSZ-UHFFFAOYSA-N 0.000 description 1
- MECNWXGGNCJFQJ-UHFFFAOYSA-N 3-piperidin-1-ylpropane-1,2-diol Chemical group OCC(O)CN1CCCCC1 MECNWXGGNCJFQJ-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 1
- NBUBVMPGVBQKSI-UHFFFAOYSA-N C(C)(=O)OC(COC)C.C(C)OCCOCCOCC Chemical compound C(C)(=O)OC(COC)C.C(C)OCCOCCOCC NBUBVMPGVBQKSI-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- SEEVRZDUPHZSOX-WPWMEQJKSA-N [(e)-1-[9-ethyl-6-(2-methylbenzoyl)carbazol-3-yl]ethylideneamino] acetate Chemical compound C=1C=C2N(CC)C3=CC=C(C(\C)=N\OC(C)=O)C=C3C2=CC=1C(=O)C1=CC=CC=C1C SEEVRZDUPHZSOX-WPWMEQJKSA-N 0.000 description 1
- 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 1
- NOZAQBYNLKNDRT-UHFFFAOYSA-N [diacetyloxy(ethenyl)silyl] acetate Chemical compound CC(=O)O[Si](OC(C)=O)(OC(C)=O)C=C NOZAQBYNLKNDRT-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- HKLVZVIXBWVFGF-UHFFFAOYSA-N benzoic acid trimethoxysilane Chemical compound C(C1=CC=CC=C1)(=O)O.CO[SiH](OC)OC HKLVZVIXBWVFGF-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- TWSMAGLIJBUJTR-UHFFFAOYSA-N butan-2-one;1-methoxypropan-2-yl acetate Chemical compound CCC(C)=O.COCC(C)OC(C)=O TWSMAGLIJBUJTR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000000976 ink Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-N o-dicarboxybenzene Natural products OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- OSIVISXRDMXJQR-UHFFFAOYSA-M potassium;2-[ethyl(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctylsulfonyl)amino]acetate Chemical compound [K+].[O-]C(=O)CN(CC)S(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F OSIVISXRDMXJQR-UHFFFAOYSA-M 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- WEZYFYMYMKUAHY-UHFFFAOYSA-N tert-butyl 2,4-dibenzylpiperazine-1-carboxylate Chemical compound C1C(CC=2C=CC=CC=2)N(C(=O)OC(C)(C)C)CCN1CC1=CC=CC=C1 WEZYFYMYMKUAHY-UHFFFAOYSA-N 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
- C09J133/04—Homopolymers or copolymers of esters
- C09J133/06—Homopolymers or copolymers of esters of esters containing only carbon, hydrogen and oxygen, the oxygen atom being present only as part of the carboxyl radical
- C09J133/10—Homopolymers or copolymers of methacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J125/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Adhesives based on derivatives of such polymers
- C09J125/02—Homopolymers or copolymers of hydrocarbons
- C09J125/04—Homopolymers or copolymers of styrene
- C09J125/08—Copolymers of styrene
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
Abstract
본 발명은 화학식 1로 표시되는 반복단위를 포함하는 바인더 수지 및 이를 포함하는 감광성 조성물에 대한 것이다.The present invention relates to a binder resin including a repeating unit represented by Formula 1 and a photosensitive composition comprising the same.
본 발명에 의하면 현상 시간이 단축되고, 현상성이 개선되는 효과가 있다.According to the present invention, there is an effect that the developing time is shortened and the developability is improved.
현상성, 감광성 조성물, 바인더 수지. Developable, photosensitive composition, binder resin.
Description
본 발명은 바인더 수지와, 이를 포함하는 감광성 수지조성물과 이 감광성 수지조성물에 의하여 제조된 컬럼스페이서에 대한 것이다.The present invention relates to a binder resin, a photosensitive resin composition comprising the same, and a column spacer prepared by the photosensitive resin composition.
감광성 조성물은 기판상에 도포되어 도막을 형성하고, 이 도막의 특정 부분에 포토마스크 등을 이용하여 광조사에 의한 노광을 실시한 후, 비노광부를 현상 처리하여 제거함으로써 패턴을 형성하는데 사용될 수 있다. The photosensitive composition may be applied to a substrate to form a coating film, and a specific portion of the coating film may be exposed by light irradiation using a photomask or the like, and then used to form a pattern by developing and removing the non-exposed portion.
이러한 감광성 조성물은 광을 조사하여 중합하고 경화시키는 것이 가능하므로 광경화성 잉크, 감광성 인쇄판, 각종 포토레지스트, LCD용 컬러 필터 포토레지스트, 컬럼스페이서, 수지 블랙 매트릭스용 포토레지스트, 또는 투명 감광재 등에 이용되고 있다.Since the photosensitive composition can be irradiated with light to polymerize and harden, the photosensitive composition is used for photocurable inks, photosensitive printing plates, various photoresists, color filter photoresists for LCDs, column spacers, photoresists for resin black matrices, or transparent photoresists. have.
감광성 조성물은 통상적으로 바인더 수지, 에틸렌성 불포화 결합을 갖는 중합성 화합물, 광중합 개시제 및 용매를 포함한다.The photosensitive composition usually contains a binder resin, a polymerizable compound having an ethylenically unsaturated bond, a photopolymerization initiator and a solvent.
감광성 수지조성물에 있어서, 현상 시간을 단축하거나 감도를 개선하는 등의 현상성 개선은 생산 효율의 향상 등에 있어서, 중요한 문제이다.In the photosensitive resin composition, improvement of developability, such as shortening developing time or improving sensitivity, is an important problem in improving production efficiency.
따라서, 현상성을 개선하기 위한 노력이 계속되어 왔다.Therefore, efforts to improve developability have been continued.
종래에는 바인더 수지의 제조시 과량이 산기 모노머를 투입하여, 바인더 수지 중 산기 모노머의 비율을 높이는 방법이 사용되었다. 그런데, 높은 산가를 갖는 바인더 수지는 광중합성 관능기의 도입시 통상 사용되는 용매에 대한 용해도가 낮아 중합 도중 침전이 생겨 원하는 분자량을 얻을 수 없는 등의 문제가 있다. 또한, 바인더 수지의 제조시 산기 모노머의 비율을 높게 하는 경우, 다른 특성을 부여하는 모노머의 비율이 상대적으로 낮아져 다른 특성을 해치게 된다.In the past, a method in which an excess amount of an acid group monomer is added in the production of the binder resin to increase the proportion of the acid group monomer in the binder resin has been used. However, a binder resin having a high acid value has a problem such as low solubility in a solvent which is usually used at the time of introduction of the photopolymerizable functional group, so that precipitation occurs during the polymerization and the desired molecular weight cannot be obtained. In addition, in the case of increasing the ratio of the acid group monomer in the manufacture of the binder resin, the ratio of the monomers giving other characteristics is relatively low, and the other characteristics are impaired.
본 발명이 해결하고자 하는 과제는 현상성이 개선된 감광성 수지조성물을 제공하는 것이다.The problem to be solved by the present invention is to provide a photosensitive resin composition with improved developability.
본 발명에 의한 바인더 수지는 다음의 화학식 1로 표시되는 반복단위를 포함한다.The binder resin according to the present invention includes a repeating unit represented by the following formula (1).
화학식 1Formula 1
R1은 에스테르류이고,R 1 is an ester,
a는 5~30이며, b는 5~30이며, c는 5~30이고, d는 0~30, e는 5~20이다.a is 5-30, b is 5-30, c is 5-30, d is 0-30, e is 5-20.
또한, 상기 화학식 1에서의 R1은 다음의 화학식 2의 구조를 가질 수 있다.Further, R 1 in the formula (1) may have a structure of the formula 2 below.
화학식 2(2)
상기 화학식 2에서 R2는 알리파틱 카본 화합물, 고리화합물 중에서 선택된 다.In Formula 2, R 2 is selected from an aliphatic carbon compound and a cyclic compound.
또한, 상기 화학식 2에서의 R2는
또한, 상기 바인더 수지의 분자량은 5천~2만이고, 산가는0~150일 수 있다.In addition, the molecular weight of the binder resin is 5,000 to 20,000, the acid value may be 0 to 150.
본 발명에 의한 감광성 수지조성물은 화학식 1로 표현되는 반복구조를 포함하는 바인더 수지와, 용매 및 에틸렌성 불포화 결합을 가지는 중합성 화합물을 포함한다.The photosensitive resin composition according to the present invention includes a binder resin including a repeating structure represented by the formula (1), and a polymerizable compound having a solvent and an ethylenically unsaturated bond.
또한, 상기 용매는 메탄올, 에탄올, 테트라하이드로퓨란, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 프로필렌 글리콜 메틸 에테르 아세테이트, 프로필렌 글리콜 에틸 에테르 아세테이트, 프로펠렌 글리콜프로필 에테르 아세테이트, 프로필렌 글리콜 부틸 에테르 아세테이트, 메틸에틸케톤, 시클로헥사논, 4-히드록시-4-메틸-2-펜타난, 아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 2-히드록시프로피온산의 에틸, 메틸에스테르, 2-히드록시-2-메틸프로피온산의 에틸에스테르, 히드록시아세트산의 메틸, 에틸, 부틸 에스테르, 젖산에틸, 젖산에틸, 젖산프로필, 젖산부틸, 메톡시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 프로폭시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 부톡시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 2-메톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 2-에톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 2-부톡시프로피온산의 메 틸, 에틸, 프로필, 부틸 에스테르, 3-메톡시프로판의 메틸, 에틸, 프로필, 부틸에스테르, 3-에톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 3-부톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, N-메틸 포름아미드, N,N-디메틸 포름아미드, N-메틸 아세트아미드, N,N-디메틸 아세트아미드, N-메틸 피롤리돈, 디메틸 설폭시드, 벤질 에틸 에테르 중에서 하나 이상 선택될 수 있다.In addition, the solvent is methanol, ethanol, tetrahydrofuran, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol butyl ether acetate , Methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanane, methyl of acetic acid, ethyl, propyl, butyl ester, ethyl of 2-hydroxypropionic acid, methyl ester, 2-hydroxy- Ethyl ester of 2-methylpropionic acid, methyl of hydroxyacetic acid, ethyl, butyl ester, ethyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl of methoxyacetic acid, ethyl, propyl, butyl ester, methyl of propoxyacetic acid, Ethyl, propyl, butyl ester, butoxy acetic acid methyl, ethyl, propyl, butyl ester, 2-meth Methyl, ethyl, propyl, butyl ester of cipropionic acid, methyl of 2-ethoxypropionic acid, ethyl, propyl, butyl ester, methyl of 2-butoxypropionic acid, ethyl, propyl, butyl ester, methyl of 3-methoxypropane , Ethyl, propyl, butyl ester, methyl of 3-ethoxypropionic acid, ethyl, propyl, butyl ester, methyl of 3-butoxypropionic acid, ethyl, propyl, butyl ester, N-methyl formamide, N, N-dimethyl form One or more of amide, N-methyl acetamide, N, N-dimethyl acetamide, N-methyl pyrrolidone, dimethyl sulfoxide, benzyl ethyl ether.
또한, 상기 바인더수지는 화학식 1의 반복단위를 가지는 바인더수지에 페닐기, 아마이드기, 아크릴기를 포함하는 제3단량체를 더 중합하여 제조되는 것을 특징으로 하는 감광성 수지조성물.The binder resin may be prepared by further polymerizing a third monomer including a phenyl group, an amide group, and an acryl group in a binder resin having a repeating unit represented by Chemical Formula 1.
또한, 상기 제3 단량체는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 디메틸아미노에킬(메타)아크릴레이트, 2-페녹시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시-3-클로로프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메타)아크릴레이트, 에틸헥실 아크릴레이트, 2-메톡시에틸(메탈)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 에톡시디에틸렌글리콜(메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시트리프로필렌글리콜(메타)아크릴레이트, 메톡시폴리에틸렌글리콜(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메타)아크릴레이트, 테트라플루오로프로필(메타)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필(메타)아크릴레이트, 옥타플루오로펜틸(메타)아크릴레이트, 헵타데카플루오로데실(메타)아크릴 레이트, 트리브로모페닐(메타)아크릴레이트, 스티렌, 클로로스티렌, α-메틸 스티렌, 비닐톨루엔알릴글리시딜에테르, 글리시딜(메타)아크릴레이트, 3,4-에폭시시클로헥실메틸(메타)아크릴레이트, 글리시딜 5-노보넨-2-카복실레이트(엔도, 엑소 혼합물), 5- 노보넨-2-메틸-2-카복실레이트(엔도,엑소 혼합물), 1,2-에폭시-5-헥센 및 1,2-에폭시-9-데센, 아이소보닐 메타아크릴레이트, 아다만틸 메틸아크릴레이트, 부타다이엔모노옥사이드, 2-(디메틸아미노)에틸 메틸아크릴레이트, N-메틸말레이미드, N-에틸말레이미드, N-부틸 말레이미드, N-tert-부틸 말레이미드, N-사이클로헥실말레이미드, 3-말레이미도프로피오닉산 N-하이드록시 석시닐이미드 에스터, 3-말레이미도프로피오닉산, 부타다이엔 술폰, 에틸렌 글리콜 페닐 에테르 아크릴레이트, 2-(4-벤조일-3-하이드록시페녹시)-에틸 아크릴레이트, 2-하이드로-3-페닐옥시프로필 아크릴레이트 중에서 하나 이상 선택될 수 있다.In addition, the third monomer may be methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, 2-phenoxyethyl (Meth) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydrate Oxypropyl (meth) acrylate, ethylhexyl acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (Meth) acrylate, methoxy tripropylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonyl phenoxy polyethylene glycol (meth) acrylate, p-nonyl Phenoxypolypropylene glycol (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) ) Acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, styrene, chlorostyrene, α-methyl styrene, vinyltolueneallyl glycidyl ether, glycidyl (meth) acrylic Latex, 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl 5-norbornene-2-carboxylate (endo, exo mixture), 5- norbornene-2-methyl-2-carboxylate (endo) , Exo mixtures), 1,2-epoxy-5-hexene and 1,2-epoxy-9-decene, isobornyl methacrylate, adamantyl methylacrylate, butadiene monooxide, 2- (dimethylamino Ethyl methyl acrylate, N-methyl maleimide, N-ethyl maleimide, N-butyl maleimide, N-tert- Butyl maleimide, N-cyclohexylmaleimide, 3-maleimido propionic acid N-hydroxy succinylimide ester, 3-maleimido propionic acid, butadiene sulfone, ethylene glycol phenyl ether acrylate, 2- One or more of (4-benzoyl-3-hydroxyphenoxy) -ethyl acrylate, 2-hydro-3-phenyloxypropyl acrylate can be selected.
또한, 광중합 개시제를 더 포함할 수 있다.In addition, the photopolymerization initiator may be further included.
또한, 상기 광중합 개시제는 티옥산톤, 2,4-디에틸 티옥산톤, 티옥산톤-4-술폰산, 벤조페논, 4,4′-비스(디에틸아미노)벤조페논, 아세토페논, p-디메틸아미노아세토페논, a,a′-디메톡시아세톡시벤조페논, 2,2′-디메톡시-2-페틸아세토페논, p-메톡시아세토페논, 2,-벤질-2-디에틸아미노-1-(4-모르폴리노페닐)-부탄-1-온, 2-히드록시-2-메틸-1-페닐프로판-1-온, 4-(2-히드록시에톡시)페닐-(2-히드록시-2-프로필)케톤, 1-히드록시시클로헥실페닐케톤, 1,3-나프토퀴논, 1,3,5-트리스(트리클로로메틸)-s-트리아진, 1,3-비스(트리클로로메틸)-5-(2-클로로페닐)-s-트리아진, 1,3-비스(트리클로로페닐)-s-트리아진, 페나실 클로라이드, 트리브로모메틸페닐술 폰, 트리스(트리클로로메틸)-s-트리아진, 디-t-부틸포옥사이드, 2,4,6-트리메틸 벤조일 디페닐 포스핀 옥사이드 중에서 1종이상 선택될 수 있다.The photopolymerization initiator may be thioxanthone, 2,4-diethyl thioxanthone, thioxanthone-4-sulfonic acid, benzophenone, 4,4'-bis (diethylamino) benzophenone, acetophenone, p- Dimethylaminoacetophenone, a, a'-dimethoxyacetoxybenzophenone, 2,2'-dimethoxy-2-petylacetophenone, p-methoxyacetophenone, 2, -benzyl-2-diethylamino-1 -(4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy Hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenylketone, 1,3-naphthoquinone, 1,3,5-tris (trichloromethyl) -s-triazine, 1,3-bis (trichloro Rhomethyl) -5- (2-chlorophenyl) -s-triazine, 1,3-bis (trichlorophenyl) -s-triazine, phenacyl chloride, tribromomethylphenylsulfon, tris (trichloromethyl at least one of -s-triazine, di-t-butylphosphate, 2,4,6-trimethyl benzoyl diphenyl phosphine oxide It can be.
본 발명에 의한 컬럼 스페이서는 상기의 감광성 수지조성물에 의해 제조된다.The column spacer according to the present invention is produced by the above photosensitive resin composition.
본 발명에 의하면 현상 시간이 단축되고, 현상성이 개선되는 효과가 있다.According to the present invention, there is an effect that the developing time is shortened and the developability is improved.
본 발명에 의한 바인더 수지는 다음의 화학식 1의 반복구조를 포함한다.The binder resin according to the present invention includes a repeating structure of the following Chemical Formula 1.
화학식 1Formula 1
R1은 에스테르류이고, R 1 is an ester,
a는 5~30이며, b는 5~30이며, c는 5~30이고, d는 0~30, e는 5~20이다.a is 5-30, b is 5-30, c is 5-30, d is 0-30, e is 5-20.
R1은 다음의 화학식 2의 구조를 가질 수 있는데, R 1 may have a structure of Formula 2,
화학식 2(2)
R2는 알리파틱 탄소 화합물(aliphatic carbon compound) 또는 고리화합물일 수 있다.R 2 may be an aliphatic carbon compound or a cyclic compound.
이러한 R2는,
이 경우 다음의 화학식 3 및 화학식 4의 반복구조를 가지게 되는데, 바인더 수지의 경우, 산가를 조절하지 않고서도 고리 화합물의 도입에 의해 현상성이 개선되므로 산가의 조절에 따른 침전이나, 다른 특성의 저하가 없으며 현상성이 우수하다.In this case, it has the repeating structure of the following formulas (3) and (4), in the case of the binder resin, the developability is improved by the introduction of the cyclic compound without adjusting the acid value, so precipitation or degradation of other properties due to the adjustment of the acid value It is excellent in developability.
[화학식 3](3)
[화학식 4][Formula 4]
본 발명에 의한 바인더 수지는 고리화합물의 입체구조 때문에 현상성이 개선된다. 또한, 내열성이 우수하므로 포스트베이크 온도에서 열분해가 일어나지 않는다.The binder resin according to the present invention has improved developability due to the steric structure of the cyclic compound. In addition, since the heat resistance is excellent, no pyrolysis occurs at the postbaking temperature.
본 발명에 의한 바인더 수지는 분자량이 5천에서 2만, 산가는 0에서 150인 것이 바람직하다. It is preferable that the binder resin by this invention has a molecular weight of 5,000-20,000, and an acid value is 0-150.
본 발명에 의한 감광성 수지조성물은 상기의 화학식 1로 표시되는 구조를 포함하는 바인더 수지와, 용매와, 에틸렌성 불포화 결합을 갖는 중합성 화합물을 포함한다. The photosensitive resin composition which concerns on this invention contains the binder resin containing the structure represented by said Formula (1), a solvent, and a polymeric compound which has an ethylenically unsaturated bond.
상기 용매는 상기 바인더 수지의 제조 또는 조성물의 고형분 및 점도 유지의 역할을 하며, 다음과 같은 물질을 사용할 수 있다. 메탄올, 에탄올 등의 알코올류 테트라하이드로퓨란, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르 등의 에테르류 프로필렌 글리콜 메틸 에테르 아세테이트, 프로필렌 글리콜 에틸 에테 르 아세테이트, 프로펠렌 글리콜프로필 에테르 아세테이트, 프로필렌 글리콜 부틸 에테르 아세테이트 등의 프로필렌 글리콜 알킬 에테르 아세테이트류 등이다. 이러한 용매 가운데에서 용해성, 각 성분과의 반응성 및 도막 형성의 편리성의 관점에서 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 프로펠렌 글리콜 메틸 에테르 아세테이트류 메틸에틸케톤, 시클로헥사논, 4-히드록시-4-메틸-2-펜타난 등의 케톤류 아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 2-히드록시프로피온산의 에틸, 메틸에스테르, 2-히드록시-2-메틸프로피온산의 에틸에스테르, 히드록시아세트산의 메틸, 에틸, 부틸 에스테르, 젖산에틸, 젖산에틸, 젖산프로필, 젖산부틸, 메톡시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 프로폭시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 부톡시아세트산의 메틸, 에틸, 프로필, 부틸에스테르, 2-메톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 2-에톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 2-부톡시프로피온산의 메틸, 에틸, 프로필, 부틸 에스테르, 3-메톡시프로판의 메틸, 에틸, 프로필, 부틸에스테르, 3-에톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르, 3-부톡시프로피온산의 메틸, 에틸, 프로필, 부틸에스테르 등의 에스테르류의 사용이 바람직하다.The solvent serves to maintain the solid content and viscosity of the binder resin or the composition, and the following materials may be used. Alcohols, such as methanol and ethanol Ethers, such as tetrahydrofuran, diethylene glycol dimethyl ether, and diethylene glycol diethyl ether Propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, propylene glycol butyl Propylene glycol alkyl ether acetates such as ether acetate and the like. Diethylene glycol dimethyl ether, diethylene glycol diethyl ether, propylene glycol methyl ether acetate methyl ethyl ketone, cyclohexanone, 4-hydride from the viewpoint of solubility, reactivity with each component, and convenience of coating film formation among these solvents Methyl, ethyl, propyl, butyl esters of ketone acetic acid such as hydroxy-4-methyl-2-pentanane, ethyl esters of 2-hydroxypropionic acid, methyl esters, ethyl esters of 2-hydroxy-2-methylpropionic acid, hydroxy Methyl, ethyl, butyl ester of acetic acid, ethyl lactate, ethyl lactate, propyl lactate, butyl lactate, methyl, ethyl, propyl, butyl ester of methoxyacetic acid, methyl, ethyl, propyl, butyl ester, butoxyacetic acid of propoxyacetic acid Methyl, ethyl, propyl, butyl ester, methyl of 2-methoxypropionic acid, ethyl, propyl, butyl ester, methyl of 2-ethoxypropionic acid, , Propyl, butyl ester, methyl, ethyl, propyl, butyl ester of 2-butoxypropionic acid, methyl, ethyl, propyl, butyl ester of 3-methoxypropane, methyl, ethyl, propyl, butyl ester of 3-ethoxypropionic acid The use of esters such as methyl, ethyl, propyl, and butyl esters of and 3-butoxypropionic acid is preferred.
또한 상기 용매는 고비등점 용매와 함께 사용될 수 있다. 사용 가능한 고비등점 용매로서, 예컨대 N-메틸 포름아미드, N,N-디메틸 포름아미드, N-메틸 아세트아미드, N,N-디메틸 아세트아미드, N-메틸 피롤리돈, 디메틸 설폭시드, 벤질 에틸 에테르를 들 수 있다.The solvent may also be used with high boiling solvents. As the high boiling point solvent which can be used, for example, N-methyl formamide, N, N-dimethyl formamide, N-methyl acetamide, N, N-dimethyl acetamide, N-methyl pyrrolidone, dimethyl sulfoxide, benzyl ethyl ether Can be mentioned.
또한, 상기 에틸렌성 불포화 결합을 가지는 중합성 화합물은 에틸렌글리콜 디(메타)아크릴레이트, 에틸렌기의 수가 2∼14인 폴리에틸렌 글리콜 디(메타)아크릴레이트, 트리메틸올프로판 디(메타)아크릴레이트, 트리메틸올프로판 트리(메타)아크릴레이트, 펜타에리스리톨 트리(메타)아크릴레이트, 펜타에리스리톨 테트라(메타)아크릴레이트, 프로필렌기의 수가 2∼14인 프로필렌 글리콜 디(메타)아크릴레이트, 디펜타에리스리톨 펜타(메타)아크릴레이트, 디펜타에리스리톨 헥사(메타)아크릴레이트 등의 다가 알콜을 α, β-불포화 카르복실산으로 에스테르화하여 얻어지는 화합물; 트리메틸올프로판트리글리시딜에테르아크릴산 부가물, 비스페놀 A 디글리시딜에테르아크릴산 부가물 등의 글리시딜기를 함유하는 화합물에 (메타)아크릴산을 부가하여 얻어지는 화합물; β-히드록시에틸(메타)아크릴레이트의 프탈산디에스테르, β-히드록시에틸 (메타)아크릴레이트의 톨루엔 디이소시아네이트 부가물 등의 수산기 또는 에틸렌성 불포화 결합을 가지는 화합물과 다가 카르복실산과의 에스테르 화합물, 또는 폴리이소시아네이트와의 부가물; 및 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 2-에틸헥실(메타)아크릴레이트 등의 (메타)아크릴산 알킬에스테르로 이루어지는 군으로부터 선택되는 1 종 이상을 사용할 수 있으나, 이들에만 한정되지 않고 당 기술 분야에 알려져 있는 것들을 사용할 수도 있다.Moreover, the polymeric compound which has the said ethylenically unsaturated bond is ethylene glycol di (meth) acrylate, the polyethylene glycol di (meth) acrylate whose number of ethylene groups is 2-14, trimethylolpropane di (meth) acrylate, trimethyl Olpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, propylene glycol di (meth) acrylate with 2 to 14 propylene groups, dipentaerythritol penta (meth Compound obtained by esterifying polyhydric alcohols, such as a acrylate and dipentaerythritol hexa (meth) acrylate with the (alpha), (beta)-unsaturated carboxylic acid; Compounds obtained by adding (meth) acrylic acid to a compound containing glycidyl groups such as trimethylolpropanetriglycidyl ether acrylic acid adduct and bisphenol A diglycidyl ether acrylic acid adduct; Ester compound of the compound which has hydroxyl group or ethylenically unsaturated bond, such as phthalic acid diester of (beta) -hydroxyethyl (meth) acrylate and toluene diisocyanate adduct of (beta) -hydroxyethyl (meth) acrylate, and polyhydric carboxylic acid Or adducts with polyisocyanates; And one or more selected from the group consisting of (meth) acrylic acid alkyl esters such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, and 2-ethylhexyl (meth) acrylate. Although not limited thereto, those known in the art may be used.
상기 감광성 수지조성물 전체 중 상기 용매는 60~80중량%, 상기 바인더 수지는 5~20중량%로 포함하는 것이 바람직하다. It is preferable that the said solvent contains 60 to 80 weight% and the said binder resin in 5 to 20 weight% of the said whole photosensitive resin composition.
또한, 본 발명에 의한 감광성 수지조성물의 바인더 수지는 상기 화학식 1의 반복구조를 가지는 바인더 수지에 페닐기, 아마이드기, 아크릴기를 포함하는 제3단 량체를 더 추가하여 중합한 바인더 수지일 수 있다.In addition, the binder resin of the photosensitive resin composition according to the present invention may be a binder resin polymerized by further adding a third monomer including a phenyl group, an amide group, and an acrylic group to a binder resin having a repeating structure of Formula 1.
제3단량체의 예로는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 디메틸아미노에킬(메타)아크릴레이트, 2-페녹시에틸(메타)아크릴레이트, 2-히드록시프로필(메타)아크릴레이트, 2-히드록시-3-클로로프로필(메타)아크릴레이트, 4-히드록시부틸(메타)아크릴레이트, 아실옥틸옥시-2-히드록시프로필(메타)아크릴레이트, 에틸헥실 아크릴레이트, 2-메톡시에틸(메탈)아크릴레이트, 3-메톡시부틸(메타)아크릴레이트, 에톡시디에틸렌글리콜(메타)아크릴레이트, 메톡시트리에틸렌글리콜(메타)아크릴레이트, 메톡시트리프로필렌글리콜(메타)아크릴레이트, 메톡시폴리에틸렌글리콜(메타)아크릴레이트, 페녹시디에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리에틸렌글리콜(메타)아크릴레이트, p-노닐페녹시폴리프로필렌글리콜(메타)아크릴레이트, 테트라플루오로프로필(메타)아크릴레이트, 1,1,1,3,3,3-헥사플루오로이소프로필(메타)아크릴레이트, 옥타플루오로펜틸(메타)아크릴레이트, 헵타데카플루오로데실(메타)아크릴레이트, 트리브로모페닐(메타)아크릴레이트, 스티렌, 클로로스티렌, α-메틸 스티렌, 비닐톨루엔알릴글리시딜에테르, 글리시딜(메타)아크릴레이트, 3,4-에폭시시클로헥실메틸(메타)아크릴레이트, 글리시딜 5-노보넨-2-카복실레이트(엔도, 엑소 혼합물), 5- 노보넨-2-메틸-2-카복실레이트(엔도,엑소 혼합물), 1,2-에폭시-5-헥센 및 1,2-에폭시-9-데센, 아이소보닐 메타아크릴레이트, 아다만틸 메틸아크릴레이트, 부타다이엔모노옥사이드, 2-(디메틸아미노)에틸 메틸아크릴레이트, N-메틸말레이미드, N-에틸말레이미드, N-부틸 말레이미드, N-tert-부틸 말레이미드, N-사이클로헥실말레이미드, 3-말레이미도프로피오닉산 N-하이드록시 석시닐이미드 에스터, 3-말레이미도프로피오닉산, 부타다이엔 술폰, 에틸렌 글리콜 페닐 에테르 아크릴레이트, 2-(4-벤조일-3-하이드록시페녹시)-에틸 아크릴레이트, 2-하이드로-3-페닐옥시프로필 아크릴레이트 등이 있고, 이를 1종이상 선택하여 사용할 수 있다.Examples of tertiary monomers include methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, benzyl (meth) acrylate, dimethylaminoethyl (meth) acrylate, 2-phenoxyethyl ( Meta) acrylate, 2-hydroxypropyl (meth) acrylate, 2-hydroxy-3-chloropropyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, acyloctyloxy-2-hydroxy Propyl (meth) acrylate, ethylhexyl acrylate, 2-methoxyethyl (meth) acrylate, 3-methoxybutyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol ( Meth) acrylate, methoxy tripropylene glycol (meth) acrylate, methoxy polyethylene glycol (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, p-nonylphenoxy polyethylene glycol (meth) acrylate, p Nonylphenoxy Cypolypropylene glycol (meth) acrylate, tetrafluoropropyl (meth) acrylate, 1,1,1,3,3,3-hexafluoroisopropyl (meth) acrylate, octafluoropentyl (meth) Acrylate, heptadecafluorodecyl (meth) acrylate, tribromophenyl (meth) acrylate, styrene, chlorostyrene, α-methyl styrene, vinyltolueneallyl glycidyl ether, glycidyl (meth) acrylate , 3,4-epoxycyclohexylmethyl (meth) acrylate, glycidyl 5-norbornene-2-carboxylate (endo, exo mixture), 5- norbornene-2-methyl-2-carboxylate (endo, Exo mixtures), 1,2-epoxy-5-hexene and 1,2-epoxy-9-decene, isobornyl methacrylate, adamantyl methylacrylate, butadiene monooxide, 2- (dimethylamino) Ethyl methyl acrylate, N-methylmaleimide, N-ethylmaleimide, N-butyl maleimide, N-tert-butyl Maleimide, N-cyclohexylmaleimide, 3-maleimidopropionic acid N-hydroxy succinylimide ester, 3-maleimidopropionic acid, butadiene sulfone, ethylene glycol phenyl ether acrylate, 2- ( 4-benzoyl-3-hydroxyphenoxy) -ethyl acrylate, 2-hydro-3-phenyloxypropyl acrylate, and the like, and one or more thereof can be selected and used.
상기 제3단량체는 전체 감광성 수지 조성물 중 5~25중량%로 포함하는 것이 바람직하다.It is preferable to contain the said 3rd monomer in 5 to 25weight% of all the photosensitive resin compositions.
또한, 광중합 개시제를 더 사용할 수 있는데, 상기 광중합 개시제는 케톤류 안트라퀴논, 퀴논류, 할로겐화합물, 과산화물, 아실 포스핀 옥사이드류가 사용될 수 있다.In addition, a photopolymerization initiator may be further used, and the photopolymerization initiator may be a ketone anthraquinone, quinones, a halogen compound, a peroxide, or an acyl phosphine oxide.
이러한, 광중합 개시제의 예로는 티옥산톤, 2,4-디에틸 티옥산톤, 티옥산톤-4-술폰산, 벤조페논, 4,4′-비스(디에틸아미노)벤조페논, 아세토페논, p-디메틸아미노아세토페논, a,a′-디메톡시아세톡시벤조페논, 2,2′-디메톡시-2-페틸아세토페논, p-메톡시아세토페논, 2,-벤질-2-디에틸아미노-1-(4-모르폴리노페닐)-부탄-1-온, 2-히드록시-2-메틸-1-페닐프로판-1-온, 4-(2-히드록시에톡시)페닐-(2-히드록시-2-프로필)케톤, 1-히드록시시클로헥실페닐케톤, 1,3-나프토퀴논, 1,3,5-트리스(트리클로로메틸)-s-트리아진, 1,3-비스(트리클로로메틸)-5-(2-클로로페닐)-s-트리아진, 1,3-비스(트리클로로페닐)-s-트리아진, 페나실 클로라이드, 트리브로모메틸페닐술폰, 트리스(트리클로로메틸)-s-트리아진, 디-t-부틸포옥사이드, 2,4,6-트리메틸 벤조일 디페닐 포스핀 옥사이드 등이 있다.Examples of such photoinitiators include thioxanthone, 2,4-diethyl thioxanthone, thioxanthone-4-sulfonic acid, benzophenone, 4,4'-bis (diethylamino) benzophenone, acetophenone, p -Dimethylaminoacetophenone, a, a'-dimethoxyacetoxybenzophenone, 2,2'-dimethoxy-2-petylacetophenone, p-methoxyacetophenone, 2, -benzyl-2-diethylamino- 1- (4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2- Hydroxy-2-propyl) ketone, 1-hydroxycyclohexylphenyl ketone, 1,3-naphthoquinone, 1,3,5-tris (trichloromethyl) -s-triazine, 1,3-bis ( Trichloromethyl) -5- (2-chlorophenyl) -s-triazine, 1,3-bis (trichlorophenyl) -s-triazine, phenacyl chloride, tribromomethylphenylsulphone, tris (trichloromethyl ) -s-triazine, di-t-butylfooxide, 2,4,6-trimethyl benzoyl diphenyl phosphine oxide and the like.
상기 광중합 개시제는 전체 감광성 수지 조성물 중 0.5~4중량%로 포함하는 것이 바람직하다.It is preferable to contain the said photoinitiator in 0.5 to 4 weight% of all the photosensitive resin compositions.
또한, 계면활성제 또는 접착 조제와 같이 일반적으로 감광성 수지조성물에 첨가되는 첨가제를 더 포함할 수도 있다.In addition, it may further include an additive generally added to the photosensitive resin composition, such as a surfactant or an adhesion aid.
계면활성제로는 3M사의 FC-129,FC-170C, FC-430, FC-4430, DIC사의 F-172, F-173, F-183, F-470, F-475, 신에츠실리콘사의 KP322,KP323,KP340, KP341과 같은 불소 및 실리콘계 계면활성제를 포함할 수 있다.As surfactant, 3M's FC-129, FC-170C, FC-430, FC-4430, DIC's F-172, F-173, F-183, F-470, F-475 and Shin-Etsu Silicone KP322, KP323 Fluorine and silicone-based surfactants such as KP340 and KP341.
또한, 접착조제로서는 관능성 실란 커플링제가 사용될 수 있다. 예를들어 트리메톡시실란 안식향산, γ-이소시아네이트프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란, γγ-메타크릴록시프로필트리메톡시실란, 비닐트리아세톡시실란, 비닐트리메톡시실란 등을 사용할 수 있다.In addition, a functional silane coupling agent may be used as the adhesion aid. For example, trimethoxysilane benzoic acid, γ-isocyanatepropyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γγ-methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxy Silane and the like can be used.
또한, 본 발명에 의한 감광성 수지 조성물은 컬럼 스페이서의 제조에 사용될 수 있다. In addition, the photosensitive resin composition according to the present invention can be used for the production of column spacers.
이하에서는, 실시예를 통하여 본 발명을 보다 자세하게 설명한다. 하기의 실시예는 본 발명을 설명하기 위한 것일 뿐 본 발명이 이에 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail with reference to Examples. The following examples are only for illustrating the present invention, but the present invention is not limited thereto.
제조예Manufacturing example 1 : 바인더 수지 1의 제조 1: Preparation of Binder Resin 1
반응 용기에 열개시제로서 2,2'-아조비스이소부티로니트릴(AIBN)을 3 중량부 용매에 녹인 후 벤질메타아크릴레이트/N-페닐말레이미드/스티렌/메타아크릴산/2-메틸-2-아다만틸-5-노보렌-2-카보실레이트를 15/25/25/25/10의 몰비로 투입한 후 질소 분위기에서 60℃를 유지하며 12시간 반응시켰다. 2,2'-azobisisobutyronitrile (AIBN) was dissolved in 3 parts by weight of solvent as a thermal initiator in the reaction vessel, and then benzyl methacrylate / N-phenylmaleimide / styrene / methacrylic acid / 2-methyl-2- Adamantyl-5-norborene-2-carbosylate was added at a molar ratio of 15/25/25/25/10, and the reaction was carried out for 12 hours while maintaining 60 ° C in a nitrogen atmosphere.
상기에서 얻은 공중합체 용액을 교반기가 부착된 플라스크에 투입하고, 글리시딜메타아크릴레이트를 가한 다음, 추가로 24시간 반응시켜 감광성 열경화성 공중합체를 제조하였다. 제조된 바인더 수지1의 산가는 55KOHmg/g, 중량평균분자량은 14,500이었다.The copolymer solution obtained above was added to a flask with a stirrer, and glycidyl methacrylate was added, followed by further reaction for 24 hours to prepare a photosensitive thermosetting copolymer. The acid value of the prepared binder resin 1 was 55KOHmg / g, the weight average molecular weight was 14,500.
제조예Manufacturing example 2 : 바인더 수지 2의 제조 2: Preparation of Binder Resin 2
반응 용기에 2,2'-아조비스이소부티로니트릴(AIBN) 3 중량부를 용매에 녹인 후 벤질메타아크릴레이트/N-페닐말레이미드/스티렌/노보렌산을 25/25/25/25의 몰비로 투입한 후 질소 분위기에서 60℃를 유지하며 12시간 반응시켰다. After dissolving 3 parts by weight of 2,2'-azobisisobutyronitrile (AIBN) in a solvent in a reaction vessel, benzylmethacrylate / N-phenylmaleimide / styrene / novoronic acid in a molar ratio of 25/25/25/25 After the addition, the reaction was carried out for 12 hours while maintaining at 60 ° C. in a nitrogen atmosphere.
상기에서 얻은 공중합체 용액을 교반기가 부착된 플라스크에 투입하고, 글리시딜메타아크릴레이트를 가한 다음, 추가로 24시간 반응시켜 감광성 열경화성 공중합체를 제조하였다. 제조된 바인더 수지2의 산가는 60KOHmg/g, 중량평균분자량은 13,000이었다.The copolymer solution obtained above was added to a flask with a stirrer, and glycidyl methacrylate was added, followed by further reaction for 24 hours to prepare a photosensitive thermosetting copolymer. The acid value of the prepared binder resin 2 was 60 KOHmg / g, the weight average molecular weight was 13,000.
비교제조예Comparative Production Example : 바인더 수지 3의 제조 : Preparation of Binder Resin 3
제조예 1과 동일한 방법으로 벤질메타아크릴레이트/N-페닐말레이미드/스티렌/메타아크릴산을 25/25/25/25의 몰비로 투입하여 바인더 수지 3을 제조하였다.In the same manner as in Preparation Example 1, benzyl methacrylate / N-phenylmaleimide / styrene / methacrylic acid was added at a molar ratio of 25/25/25/25 to prepare binder resin 3.
제조된 공중합체의 산가는 65 KOH mg/g, 중량평균분자량은 14,000이었다.The acid value of the prepared copolymer was 65 KOH mg / g, the weight average molecular weight was 14,000.
실시예Example 1 One
자외선 차단기와 교반기가 설치되어 있는 반응 혼합조에, 상기 제조예1에서 제조된 바인더 수지 1을 20 중량%, 다관능성 모노머(디펜타에리트리톨 헥사아크릴레이트) 15 중량%, 광개시제(상품명 : OXE-02) 0.5 중량%, 실란계에폭시 화합물(상품명 : KBM 503) 0.5 중량%, 소량의 열중합금지제(4-메톡시페놀) 및 레벨링제(상품명 : BYK 331)를 순차적으로 첨가하여 감광성 조성물을 제조한 후 교반하였다. 이어서 조성물에 프로필렌글리콜 메틸에테르아세테이트 500g 가하여, 조성물의 점도를 13cps로 조절하였다.20 wt% of the binder resin 1 prepared in Preparation Example 1, 15 wt% of a polyfunctional monomer (dipentaerythritol hexaacrylate), a photoinitiator (trade name: OXE-02) ) 0.5% by weight, silane epoxy compound (trade name: KBM 503) 0.5% by weight, a small amount of thermal polymerization inhibitor (4-methoxyphenol) and a leveling agent (trade name: BYK 331) was added sequentially to prepare a photosensitive composition After stirring. Next, 500 g of propylene glycol methyl ether acetate was added to the composition to adjust the viscosity of the composition to 13 cps.
실시예Example 2 2
실시예 1에서 바인더 수지 1 대신에 제조예 2의 바인더 수지 2를 이용하여 실시예 1과 동일한 방법으로 감광성 수지 조성물을 제조하였다.The photosensitive resin composition was manufactured by the same method as Example 1 using the binder resin 2 of the manufacture example 2 instead of the binder resin 1 in Example 1.
비교예Comparative example
실시예 1에서 바인더 수지 1 대신에 비교제조예의 바인더 수지 3을 이용하여 실시예 1과 동일한 방법으로 감광성 수지 조성물을 제조하였다.The photosensitive resin composition was manufactured by the same method as Example 1 using the binder resin 3 of the comparative manufacture example instead of the binder resin 1 in Example 1.
실험예Experimental Example 1 : 감광성 조성물의 물성 평가 1: Evaluation of Physical Properties of Photosensitive Composition
상기 실시예 및 비교예에서 제조된 감광성 조성물의 물성을 하기와 같은 방법으로 측정하였으며, 그 결과를 다음 표 1에 나타내었다.The physical properties of the photosensitive compositions prepared in Examples and Comparative Examples were measured by the following method, and the results are shown in Table 1 below.
(1) 현상특성(1) Developing characteristics
노광 후 현상액 KOH 0.04%에 패턴 생성 시간이 10초 이하면 매우 양호, 10~30초이면 양호, 30~60초이면 보통으로 평가하였다. After the exposure, 0.04% of developer KOH was very good if the pattern generation time was 10 seconds or less, good if it was 10 to 30 seconds, and normal if it was 30 to 60 seconds.
(2) 잔막율(2) residual film rate
후열 처리 전후에 두께를 측정함으로 두께의 차이를 하기 수학식 1로 평가하였다.By measuring the thickness before and after the post heat treatment, the difference in thickness was evaluated by the following equation (1).
[수학식 1][Equation 1]
잔막율 = (후열처리 후 막 두께) / (후열처리 전 막 두께) X 100 (%)Residual film ratio = (film thickness after post-heat treatment) / (film thickness before post-heat treatment) X 100 (%)
잔막율 수치가 클수록 우수하다고 할 수 있다. 잔막율이 95%가 넘는 경우 우수, 95~93% 양호, 그 이하의 경우 불량으로 평가하였다.The higher the residual film ratio, the better. When the residual film ratio was more than 95%, the evaluation was excellent, 95-93% good, and less than that.
(3) 열적 내성(3) thermal resistance
최종적으로 패턴을 형성한 후 열적인 충격에 의한 두께 변화를 하기 수학식 2로 확인하였다.After the final pattern was formed, the thickness change due to thermal shock was confirmed by Equation 2 below.
[수학식 2]&Quot; (2) "
두께 변화율 = (열처리 후 막 두께) / (열처리 전 막 두께) X 100 (%)Thickness change rate = (film thickness after heat treatment) / (film thickness before heat treatment) X 100 (%)
고온의 열이 주어졌을 때 일정한 시간이 지난 후 두께의 변화가 많지 않아야 양호하다고 할 수 있다. 240 ℃ 에서 1시간 동안 열을 가했을 때 두께 변화율이 90% 이상이면 양호, 그 이하의 경우 불량으로 평가하였다.Given the heat of high temperature, a certain amount of change in thickness after a certain period of time can be said to be good. When heat was applied at 240 ° C. for 1 hour, the rate of change in thickness was 90% or more.
(4) 내화학성(4) chemical resistance
여러 화학 물질(10 % NaOH 수용액, 10 % HCl 수용액, NMP)에 방치해 두었을 때 두께 변화를 관찰함으로 내화학성 검사를 실시하였다. 두께 변화율은 상기 수학식 2로 계산하였다. 열적 내성과 마찬가지로 화학 물질에 노출이 되었을 때 두께 변화율이 없을수록 양호하다고 할 수 있다. 상온에서 각 화학 물질에 대해서 1시간 동안 담궈 놓았을 때 103% 이하이면 양호, 그 이상이면 불량이라고 판정하였다.When left in various chemicals (10% NaOH aqueous solution, 10% HCl aqueous solution, NMP), the chemical resistance test was performed by observing the thickness change. Thickness change rate was calculated by the above equation (2). As with thermal resistance, the lower the rate of change of thickness when exposed to chemicals, the better. When submerged for 1 hour at room temperature for 1 hour, it was determined that 103% or less was good, and more than that, poor.
[표 1][Table 1]
상기 표 1에 나타난 바와 같이, 본 발명에 따른 감광성 조성물은 현상특성, 잔막율, 내열성, 내화학성이 우수함을 확인하였다.As shown in Table 1, it was confirmed that the photosensitive composition according to the present invention has excellent development characteristics, residual film ratio, heat resistance, and chemical resistance.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR101609234B1 (en) | 2015-01-13 | 2016-04-05 | 동우 화인켐 주식회사 | Photosensitive resin comopsition, photocurable pattern formed from the same and image display comprising the pattern |
| KR101611836B1 (en) * | 2015-01-13 | 2016-04-12 | 동우 화인켐 주식회사 | Photosensitive resin comopsition, photocurable pattern formed from the same and image display comprising the pattern |
| CN105785717A (en) * | 2015-01-13 | 2016-07-20 | 东友精细化工有限公司 | Photosensitive resin composition, photocurable pattern formed from the same and image display comprising the pattern |
| JP2016130844A (en) * | 2015-01-13 | 2016-07-21 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Photosensitive resin composition, photocuring pattern formed therefrom, and image display device including the same |
| JP2016130847A (en) * | 2015-01-13 | 2016-07-21 | 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. | Photosensitive resin composition, photocuring pattern formed therefrom, and image display device including the same |
| KR20190053801A (en) * | 2017-11-10 | 2019-05-20 | 주식회사 엘지화학 | Photo-curable and thermo-curable copolymer, and photosensitive resin composition, photosensitive resin film, color filter using the same |
| KR102118627B1 (en) | 2017-11-10 | 2020-06-09 | 주식회사 엘지화학 | Photo-curable and thermo-curable copolymer, and photosensitive resin composition, photosensitive resin film, color filter using the same |
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| KR20090081208A (en) | 2009-07-28 |
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