KR102008491B1 - Photosensitive resin composition for organic insulator - Google Patents
Photosensitive resin composition for organic insulator Download PDFInfo
- Publication number
- KR102008491B1 KR102008491B1 KR1020130168994A KR20130168994A KR102008491B1 KR 102008491 B1 KR102008491 B1 KR 102008491B1 KR 1020130168994 A KR1020130168994 A KR 1020130168994A KR 20130168994 A KR20130168994 A KR 20130168994A KR 102008491 B1 KR102008491 B1 KR 102008491B1
- Authority
- KR
- South Korea
- Prior art keywords
- unsaturated
- resin composition
- weight
- photosensitive resin
- organic insulating
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims abstract description 33
- 239000012212 insulator Substances 0.000 title 1
- 239000000178 monomer Substances 0.000 claims description 46
- 229920005989 resin Polymers 0.000 claims description 27
- 239000011347 resin Substances 0.000 claims description 27
- 239000002904 solvent Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 16
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 13
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 10
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 6
- 239000005977 Ethylene Substances 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N ethyl trimethyl methane Natural products CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 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 claims description 3
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 230000035945 sensitivity Effects 0.000 abstract description 11
- 238000000034 method Methods 0.000 abstract description 4
- 230000008569 process Effects 0.000 abstract description 4
- 239000010408 film Substances 0.000 description 55
- 239000011248 coating agent Substances 0.000 description 25
- 238000000576 coating method Methods 0.000 description 25
- -1 α-ethyl acrylate glycidyl ester Chemical class 0.000 description 22
- 239000003513 alkali Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 13
- 150000004702 methyl esters Chemical class 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 9
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 8
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 8
- 239000003999 initiator Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 229920002678 cellulose Polymers 0.000 description 6
- 239000001913 cellulose Substances 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 239000011521 glass Substances 0.000 description 6
- 238000011161 development Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- 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 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 4
- 229920006026 co-polymeric resin Polymers 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 238000002834 transmittance Methods 0.000 description 4
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-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
- 150000001336 alkenes Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 150000001925 cycloalkenes Chemical class 0.000 description 3
- 230000003247 decreasing effect Effects 0.000 description 3
- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 3
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- FRASJONUBLZVQX-UHFFFAOYSA-N 1,4-naphthoquinone Chemical compound C1=CC=C2C(=O)C=CC(=O)C2=C1 FRASJONUBLZVQX-UHFFFAOYSA-N 0.000 description 2
- FUWDFGKRNIDKAE-UHFFFAOYSA-N 1-butoxypropan-2-yl acetate Chemical compound CCCCOCC(C)OC(C)=O FUWDFGKRNIDKAE-UHFFFAOYSA-N 0.000 description 2
- UAJRSHJHFRVGMG-UHFFFAOYSA-N 1-ethenyl-4-methoxybenzene Chemical compound COC1=CC=C(C=C)C=C1 UAJRSHJHFRVGMG-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- DMFAHCVITRDZQB-UHFFFAOYSA-N 1-propoxypropan-2-yl acetate Chemical compound CCCOCC(C)OC(C)=O DMFAHCVITRDZQB-UHFFFAOYSA-N 0.000 description 2
- SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- OWVMFLLVLFONOO-UHFFFAOYSA-N 3-butoxypropanoic acid Chemical compound CCCCOCCC(O)=O OWVMFLLVLFONOO-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 239000004695 Polyether sulfone Substances 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 2
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 238000009835 boiling Methods 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
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical group C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical group CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 2
- 230000035699 permeability Effects 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 239000002985 plastic film Substances 0.000 description 2
- 229920006255 plastic film Polymers 0.000 description 2
- 229920006393 polyether sulfone Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007870 radical polymerization initiator Substances 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LXSVWFRZICUOLU-ZCFIWIBFSA-N (2r)-2-butoxypropanoic acid Chemical compound CCCCO[C@H](C)C(O)=O LXSVWFRZICUOLU-ZCFIWIBFSA-N 0.000 description 1
- 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 description 1
- 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 description 1
- 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 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- 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
- 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 description 1
- 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 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- PTBAHIRKWPUZAM-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCC1CO1 PTBAHIRKWPUZAM-UHFFFAOYSA-N 0.000 description 1
- CBKJLMZJKHOGEQ-UHFFFAOYSA-N 2-(oxiran-2-yl)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCC1CO1 CBKJLMZJKHOGEQ-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- JFWFAUHHNYTWOO-UHFFFAOYSA-N 2-[(2-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC=C1COCC1OC1 JFWFAUHHNYTWOO-UHFFFAOYSA-N 0.000 description 1
- OCKQMFDZQUFKRD-UHFFFAOYSA-N 2-[(3-ethenylphenyl)methoxymethyl]oxirane Chemical compound C=CC1=CC=CC(COCC2OC2)=C1 OCKQMFDZQUFKRD-UHFFFAOYSA-N 0.000 description 1
- ZADXFVHUPXKZBJ-UHFFFAOYSA-N 2-[(4-ethenylphenyl)methoxymethyl]oxirane Chemical compound C1=CC(C=C)=CC=C1COCC1OC1 ZADXFVHUPXKZBJ-UHFFFAOYSA-N 0.000 description 1
- HQEOJGGRIVORTI-UHFFFAOYSA-N 2-benzyl-2-(diethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(CC)CC)CC1=CC=CC=C1 HQEOJGGRIVORTI-UHFFFAOYSA-N 0.000 description 1
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- WYYQKWASBLTRIW-UHFFFAOYSA-N 2-trimethoxysilylbenzoic acid Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1C(O)=O WYYQKWASBLTRIW-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
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- SSIZVBOERWVGFR-UHFFFAOYSA-N 5-(oxiran-2-yl)pentyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCC1CO1 SSIZVBOERWVGFR-UHFFFAOYSA-N 0.000 description 1
- CYKONRWVCOIAHL-UHFFFAOYSA-N 5-(oxiran-2-yl)pentyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCC1CO1 CYKONRWVCOIAHL-UHFFFAOYSA-N 0.000 description 1
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- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
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- 239000004696 Poly ether ether ketone Substances 0.000 description 1
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- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
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Abstract
본 발명은 다양한 Display 공정의 유기 절연막에 적합한 감광성 수지 조성물에 관한 것으로, 보다 상세하게는, 높은 평탄도, 감도, 내열성, 투명성 및 밀착력을 얻을 수 있을 뿐만 아니라, 높은 잔막율을 유지하면서 패턴현상성을 향상시킨 유기 절연막용 감광성 수지 조성물에 관한 것이다.The present invention relates to a photosensitive resin composition suitable for an organic insulating film of various display processes, and more particularly, it is possible not only to obtain high flatness, sensitivity, heat resistance, transparency and adhesion, but also to maintain a high residual film ratio. It is related with the photosensitive resin composition for organic insulating films which improved.
Description
본 발명은 다양한 Display 공정의 유기 절연막에 적합한 감광성 수지 조성물에 관한 것으로, 보다 상세하게는, 높은 평탄도, 감도, 내열성, 투명성 및 밀착력을 얻을 수 있을 뿐만 아니라, 높은 잔막율을 유지하면서 패턴현상성을 향상시킨 유기 절연막용 감광성 수지 조성물에 관한 것이다.The present invention relates to a photosensitive resin composition suitable for an organic insulating film of various display processes, and more particularly, it is possible not only to obtain high flatness, sensitivity, heat resistance, transparency and adhesion, but also to maintain a high residual film ratio. It is related with the photosensitive resin composition for organic insulating films which improved.
유기 절연막용 감광성 수지 조성물은 플라스틱 광학부품, 각종 디스플레이패널, 예를 들면 액정디스플레이(LCD), 플라즈마디스플레이(PDP), 브라운관(CRT), 전자발광 디스플레이(EL) 등의 패널에 보호막, 평탄화막, 전극배선 연결 등의 목적으로 이용되고 있다.The photosensitive resin composition for an organic insulating film is a plastic optical component, various display panels, such as a liquid crystal display (LCD), a plasma display (PDP), a cathode ray tube (CRT), an electroluminescent display (EL), a protective film, a flattening film, It is used for the purpose of electrode wiring connection.
TFT-LCD(Thin Film Transistor Liquid Crystal Dispaly)는 TFT-array가 형성된 유기기판에 컬러필터층과 액정층을 도입하여 패널을 형성한 후 전기적인 신호를인가하여 디스플레이 하는 것을 말한다. TFT-array를 형성하기 위해서는 전극들을 보호하고, 배선 연결이 가능한 유기 절연막용 감광성 수지 조성물이 필요하다. 최근 TFT-LCD에 대한 연구는 해상도향상에 그 초점이 맞혀져 있으며 이 때 높은 해상도를 구현하기 위해서는 유기 절연막용 감광성 수지 조성물의 높은 잔막율을 유지하면서 패턴현상성이 우수하여야 한다. TFT-LCD (Thin Film Transistor Liquid Crystal Dispaly) refers to display by applying an electrical signal after forming a panel by introducing a color filter layer and a liquid crystal layer to the organic substrate formed TFT-array. In order to form a TFT-array, a photosensitive resin composition for an organic insulating film that protects electrodes and can be connected by wires is required. In recent years, research on TFT-LCD has focused on improving the resolution, and in order to realize high resolution, it has to be excellent in pattern development while maintaining a high residual film ratio of the photosensitive resin composition for an organic insulating film.
종래의 유기 절연막용 감광성 수지 조성물은 패턴현상성이 우수하면 잔막율이 떨어지며, 잔막율이 우수하면 패턴현상성이 저하되어 홀패턴의 크기가 작아지는문제가 있었다.The conventional photosensitive resin composition for organic insulating films has a problem that the residual film ratio is lowered when the pattern developability is excellent, and the pattern developability is lowered when the residual film ratio is excellent, thereby decreasing the size of the hole pattern.
본 발명은 평탄도, 감도, 내열성, 투명성, 잔막율등이 우수할 뿐만 아니라, 패턴현상성이 우수하면서 높은잔막율을 유지하는 유기 절연막용 감광성 수지 조성물을 제공하고자 한다.An object of the present invention is to provide a photosensitive resin composition for an organic insulating film which not only has excellent flatness, sensitivity, heat resistance, transparency, residual film ratio, etc., but also excellent pattern developability and maintains a high residual film ratio.
상기와 같은 목적을 달성하기 위하여, 본 발명의 일구현예는 [A]알칼리 가용성수지, [B]불포화성에틸렌계모노머, [C]광중합개시제및 [D]용매를 포함하고, 상기 [B]불포화성에틸렌계모노머는 b-1) 하기 화학식 1로 표시되는 불포화성에틸렌모노머및 b-2) 3관능 이상의 불포화기를 가지 는에틸렌모노머를 포함하는 것을 특징으로하는 하드코팅용 감광성 수지 조성물을 제공한다.
In order to achieve the above object, one embodiment of the present invention comprises [A] alkali soluble resin, [B] unsaturated unsaturated monomer, [C] photoinitiator and [D] solvent, [B] The unsaturated ethylenic monomer provides b-1) an unsaturated ethylene monomer represented by the following Chemical Formula 1 and b-2) an ethylene monomer having a trifunctional or more than three functional unsaturated group. .
<화학식 1><Formula 1>
상기 화학식 1에서, R은 탄소원자수 1 내지 6인 알킬기, 지방족 탄화수소기 또는 페닐기이다.In Formula 1, R is an alkyl group having 1 to 6 carbon atoms, an aliphatic hydrocarbon group or a phenyl group.
본 발명의 바람직한 일 구현예에서, 상기 b-1) 화학식 1로 표시되는 모노머는 중량평균분자량이 100 내지 2,000g/mol인 것을 특징으로 할 수 있다.In a preferred embodiment of the present invention, b-1) the monomer represented by Formula 1 may be characterized in that the weight average molecular weight of 100 to 2,000g / mol.
본 발명의 바람직한 일 구현예에서, 상기 하드코팅용 감광성 수지 조성물은 [A]알칼리 가용성수지 5 ~ 80 중량%, [B]불포화성에틸렌계모노머 5 ~ 60 중량%, [C]광중합개시제 0.5 ~ 20 중량% 및 [D]용매 20 ~ 80 중량%로 포함하는 것을 특징으로할 수 있다.In a preferred embodiment of the present invention, the hard coating photosensitive resin composition is [A] alkali soluble resin 5 to 80% by weight, [B] unsaturated unsaturated ethylene monomer 5 to 60% by weight, [C] photoinitiator 0.5 ~ 20 to 80% by weight and the solvent [D] 20 to 80% by weight.
본 발명의 바람직한 일구현예에서, 상기 [A]알칼리 가용성수지는 a-1) 불포화카르본산, 불포화카르본산무수물 및 이들의 혼합물로 구성된 군에서 선택되는 화합물, a-2) 에폭시기함유불포화화합물 및 a-3) 올레핀계 불포화화합물의 공중합체 수지인 것을 특징으로 할 수 있다.In a preferred embodiment of the present invention, the [A] alkali soluble resin is selected from the group consisting of a-1) unsaturated carboxylic acids, unsaturated carboxylic anhydrides and mixtures thereof, a-2) epoxy group-containing unsaturated compounds and a-3) It is characterized by being the copolymer resin of an olefinic unsaturated compound.
본 발명의 바람직한 일 구현예에서, 상기 [A]알칼리 가용성수지는 중량평균분자량이 5,000 내지 40,000g/mol인 것을 특징으로 할 수 있다.In a preferred embodiment of the present invention, the [A] alkali soluble resin may be characterized in that the weight average molecular weight of 5,000 to 40,000g / mol.
본 발명의 바람직한 일 구현예에서, 상기 하드코팅용 감광성 수지 조성물은 상온점도가 3 내지 30cps인 것을 특징으로 할 수 있다.In a preferred embodiment of the present invention, the hard coating photosensitive resin composition may be characterized in that the room temperature viscosity is 3 to 30cps.
본 발명의 다른 구현예는 상기 유기 절연막을 포함하는 디스플레이장치인 것이다.Another embodiment of the present invention is a display device including the organic insulating layer.
본 발명에 따른 감광성 수지 조성물은 평탄도, 감도, 내열성, 투명성이 우수하며, 특히 높은 잔막율을 가지면서 패턴형상성이 우수한 조성물로 고해상도 디스플레이에 적합한 유기 절연막이다.The photosensitive resin composition according to the present invention is an organic insulating film suitable for high resolution display with a composition having excellent flatness, sensitivity, heat resistance and transparency, and particularly having a high residual film ratio and excellent pattern shape.
다른 식으로 정의되지 않는 한, 본 명세서에서 사용된 모든 기술적 및 과학적 용어들은 본 발명이 속하는 기술분야에서 숙련된 전문가에 의해서 통상적으로 이해되는 것과 동일한 의미를 가진다. 일반적으로, 본 명세서에서 사용된 명명법은본 기술분야에서 잘 알려져 있고 통상적으로 사용되는 것이다.Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. In general, the nomenclature used herein is well known and commonly used in the art.
본원 명세서 전체에서, 어떤 부분이 어떤 구성요소를 "포함" 한다고 할 때, 이는 특별히 반대되는 기재가 없는 한 다른 구성요소를 제외하는 것이 아니라 다른 구성요소를 더 포함할 수 있는 것을 의미한다.Throughout this specification, when a part is said to "include" a certain component, it means that it can further include other components, without excluding the other components unless specifically stated otherwise.
본 발명은 일관점에서, [A]알칼리 가용성수지, [B]불포화성에틸렌계모노머, [C]광중합개시제 및 [D]용매를 포함하고, 상기 [B]불포화성에틸렌계모노머는 b-1) 하기 화학식 1로 표시되는 불포화성 에틸렌모노머 및 b-2) 3관능 이상의 불포화기를 가지는 에틸렌모노머를 포함하는 것을 특징으로 하는 감광성 수지 조성물에 관한 것이다.The present invention consistently includes the [A] alkali soluble resin, the [B] unsaturated ethylenic monomer, the [C] photopolymerization initiator and the [D] solvent, wherein the [B] unsaturated unsaturated monomer is b-1. The present invention relates to an unsaturated ethylene monomer represented by the following formula (1) and b-2) an ethylene monomer having a trifunctional or higher unsaturated group.
<화학식 1><Formula 1>
상기 화학식 1에서, R은 탄소원자수 1 내지 6인 알킬기, 지방족 탄화수소기 또는 페닐기이다.In Formula 1, R is an alkyl group having 1 to 6 carbon atoms, an aliphatic hydrocarbon group or a phenyl group.
이하, 본 발명을 보다 상세히 설명한다.Hereinafter, the present invention will be described in more detail.
본 발명에 따른 하드코팅용 감광성 수지 조성물은 a-1) 불포화카르본산, 불포화카르본산무수물 및 이들의 혼합물로 구성된 군에서 선택되는 화합물, a-2) 에폭시기함유 불포화화합물 및 a-3) 올레핀계 불포화화합물의 공중합체수지인 [A]알칼리 가용성수지; b-1) 상기화학식 1로 표시되는 불포화성 에틸렌모노머 및 b-2) 3관능 이상의 불포화기를 가지는 에틸렌모노머를 포함하는[B] 불포화성 에틸렌계모노머; [C]광중합개시제 및 [D]용매를 포함한다.The photosensitive resin composition for hard coating according to the present invention comprises a-1) a compound selected from the group consisting of unsaturated carboxylic acids, unsaturated carboxylic anhydrides and mixtures thereof, a-2) epoxy group-containing unsaturated compounds and a-3) olefins [A] alkali-soluble resin which is a copolymer resin of an unsaturated compound; b-1) [B] unsaturated ethylene monomer comprising an unsaturated ethylene monomer represented by Formula 1 and b-2) an ethylene monomer having a tri- or higher functional unsaturated group; [C] photoinitiator and [D] solvent.
본 발명에 따른 감광성 수지 조성물의 각 구성요소를 구체적으로 살펴보면 다음과 같다.Looking at each component of the photosensitive resin composition according to the invention in detail.
[A] 알칼리 가용성수지 [A] Alkali Soluble Resin
본 발명에 사용되는 [A]알칼리 가용성수지는 a-1) 불포화카르본산, 불포화카르본산무수물 및 이들의 혼합물로 구성된 군에서 선택되는 화합물, a-2) 에폭시기함유 불포화화합물 및 a-3) 올레핀계 불포화화합물의 공중합체수지일 수 있다.The alkali soluble resin [A] used in the present invention is selected from the group consisting of a-1) unsaturated carboxylic acids, unsaturated carboxylic anhydrides and mixtures thereof, a-2) epoxy group-containing unsaturated compounds and a-3) olefins. It may be a copolymer resin of the unsaturated compound.
상기 a-1) 불포화카르본산, 불포화카르본산무수물 및 이들의 혼합물로 구성된 군에서 선택되는 화합물로는 아크릴산, 메타크릴산, 크로톤산, 이타콘산, 말레산, 푸마르산, 시트라콘산, 메사콘산 및 이들 디카르복실산의 무수물중단독 또는 조합해서 사용할 수 있다. 이중, 아크릴산, 메타크릴산, 무수말레산등이공중합반응성, 내열성 및 입수가 용이한 점에서 바람직하게 사용된다. 상기 a-1) 단량체는 [A]알칼리 가용성수지 중에 1 내지 15중량%로 포함되는 것이 바람직하다. The compound selected from the group consisting of a-1) unsaturated carboxylic acid, unsaturated carboxylic anhydride and mixtures thereof includes acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid and Anhydrides alone or in combination of these dicarboxylic acids can be used. Of these, acrylic acid, methacrylic acid, maleic anhydride and the like are preferably used in view of easy polymerization polymerization resistance, heat resistance and availability. The a-1) monomer is preferably contained in 1 to 15% by weight of the alkali soluble resin [A].
또한, 상기 a-2)에폭시기함유 불포화화합물로는 메타크릴산글리시딜, 아크릴산글리시딜에스테르, 메타크릴산글리시딜에스테르,α-에틸아크릴산글리시딜에스테르, α-n-프로필아크릴산글리시딜에스테르, α-n-부틸아크릴산글리시딜에스테르, 아크릴산-3,4-에폭시부틸에스테르, 메타크릴산-3,4-에폭시부틸에스테르, 아크릴산-6,7-에폭시헵틸에스테르, 메타크릴산-6,7-에폭시헵틸에스테르, α-에틸아크릴산-6,7-에폭시헵틸에스테르, o-비닐벤질글리시딜에테르, m-비닐벤질글리시딜에테르, p-비닐벤질글리시딜에테르 등이 공중합반응성 및 얻어지는 박막의 내열성, 경도를 높인다는 점에서 바람직하게 사용된다. 이러한 화합물은 단독으로 또는 조합해서 사용된다. 상기 a-2) 단량체는 [A]알칼리 가용성수지 중에 1 내지 15중량%로 포함되는 것이 바람직하다. In addition, the a-2) epoxy group-containing unsaturated compound is glycidyl methacrylate, glycidyl acrylate, glycidyl methacrylate, α-ethyl acrylate glycidyl ester, and α-n-propyl acrylate. Cydyl ester, α-n-butyl acrylate glycidyl ester, acrylic acid-3,4-epoxybutyl ester, methacrylic acid-3,4-epoxybutyl ester, acrylic acid-6,7-epoxyheptyl ester, methacrylic acid -6,7-epoxyheptyl ester, α-ethylacrylic acid-6,7-epoxyheptyl ester, o-vinylbenzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, and the like. It is preferably used in view of increasing copolymerization reactivity and heat resistance and hardness of the obtained thin film. These compounds are used alone or in combination. The a-2) monomer is preferably contained in 1 to 15% by weight of the alkali soluble resin [A].
상기 a-3)올레핀계불포화화합물로는스티렌, o-메틸스티렌, m-메틸스티렌, p-메틸스티렌, 비닐톨루엔, p-메톡시스티렌, 아크릴로니트릴, 메타크릴로니트릴, 염화비닐, 염화비닐리덴, 아크릴아미드, 메타크릴아미드, 초산비닐, 1,3-부타디엔, 이소프렌, 2,3-디메틸-1,3-부타디엔, 디사이클로펜틸아크릴레이트 등을 들 수 있다. 상기 a-3) 단량체는 [A]알칼리 가용성수지 중에 1 내지 30중량%로 포함되는 것이 바람직하다. As the a-3) olefin unsaturated compound, styrene, o-methyl styrene, m-methyl styrene, p-methyl styrene, vinyl toluene, p-methoxy styrene, acrylonitrile, methacrylonitrile, vinyl chloride, vinyl chloride Leaden, acrylamide, methacrylamide, vinyl acetate, 1,3-butadiene, isoprene, 2,3-dimethyl-1,3-butadiene, dicyclopentyl acrylate, and the like. The a-3) monomer is preferably contained in 1 to 30% by weight of the alkali soluble resin [A].
이러한, [A]알칼리 가용성수지는 고형분함량이 [A]성분에 대하여 10 내지 70중량%인 것일 수 있으며, 더욱 바람직하게는 20 내지 50중량%를 함유할 수 있다. 고형분함량이 10중량% 미만인 경우는 공중합체 [A]의 보존안전성 및 [a1] ~ [a3]의구성요소를 모두 포함하는 중합체를 제조시 중합조절이 잘 되지 않아 고체화되는 경향이 있고, 70중량%를 초과하는 경우에는 공중합체 [A]의 현상성, 내열성 및 표면경도 등이 저하되는 경향이 있다. Such an alkaline soluble resin [A] may have a solid content of 10 to 70 wt% with respect to the [A] component, and more preferably 20 to 50 wt%. If the solid content is less than 10% by weight, there is a tendency to solidify due to poor polymerization control when preparing a polymer containing both the preservation safety of the copolymer [A] and the components of [a1] to [a3]. When exceeding%, there exists a tendency for developability, heat resistance, surface hardness, etc. of copolymer [A] to fall.
상기 공중합체수지인 [A]알칼리 가용성수지는 조성물 중에 10 내지 80중량%로 포함되는 것이 바람직하다. 상기 [A]알칼리 가용성수지의 함량이 상기 범위 내에 있는 경우 내수성, 내열성, 현상성 및 코팅성 개선의 효과가 있다. It is preferable that [A] alkali-soluble resin which is the said copolymer resin is contained in 10 to 80 weight% in a composition. When the content of the [A] alkali soluble resin is within the above range, there is an effect of improving the water resistance, heat resistance, developability and coating properties.
상기 공중합체 [A]의 합성에 사용된 용매로는 메탄올, 에탄올 등의 알코올류; 테트라하이드로퓨란, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르 등의 에테르류; 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜에틸에테르아세테이트, 프로펠렌글리콜프로필에테르아세테이트, 프로필렌글리콜부틸에테르아세테이트 등의 프로필렌글리콜알킬에테르아세테이트류 등이 바람직하다. 상기 용매는 [A]알칼리 가용성수지 중에 60 내지 70중량%로 포함되는 것이 바람직하다.As a solvent used for the synthesis | combination of the said copolymer [A], Alcohol, such as methanol and ethanol; Ethers such as tetrahydrofuran, diethylene glycol dimethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate and propylene glycol butyl ether acetate are preferable. The solvent is preferably contained in 60 to 70% by weight of the alkali soluble resin [A].
상기 공중합체 [A]의 합성에 사용된 중합개시제로는, 일반적으로 라디칼중합개시제로서 알려져 있는 것이면 제한없이 사용가능하고, 예를 들면 2,2'-아조비스이소부티로니트릴, 2,2'-아조비스-(2,4-디메틸발레로니트릴), 2,2'-아조비스-(4-메톡시-2,4-디메틸발레로니트릴) 등의 아조화합물; 벤조일퍼옥시드, t-부틸퍼옥시피바레이트, 1,1'-비스-(t-부틸퍼옥시)시클로헥산 등의 유기과산화물; 및 과산화수소를 들 수 있다. 라디칼중합개시제로서 과산화물을 이용한 경우에는 과산화물을 환원제와 함께 이용하여 레독스 개시제로 사용해도 좋다. 상기 중합개시제는 [A]알칼리 가용성수지 중에 1 내지 10중량%로 포함되는 것이 바람직하다.As a polymerization initiator used for the synthesis | combination of the said copolymer [A], as long as it is generally known as a radical polymerization initiator, it can be used without limitation, For example, 2,2'- azobisisobutyronitrile, 2,2 ' Azo compounds such as -azobis- (2,4-dimethylvaleronitrile) and 2,2'-azobis- (4-methoxy-2,4-dimethylvaleronitrile); Organic peroxides such as benzoyl peroxide, t-butylperoxy pibarate, 1,1'-bis- (t-butylperoxy) cyclohexane; And hydrogen peroxide. When a peroxide is used as a radical polymerization initiator, you may use it as a redox initiator by using a peroxide together with a reducing agent. The polymerization initiator is preferably contained in 1 to 10% by weight of the alkali soluble resin [A].
전술된 [A]알칼리 가용성수지는 중량평균분자량 5,000 내지 40,000g/mol인 것이다. 상기 알칼리 가용성수지의 중량평균분자량이 상기 범위 내에 있는 경우 우수한 코팅성 및 현상성을 가질 수 있다.The above-mentioned [A] alkali soluble resin is a weight average molecular weight of 5,000 to 40,000 g / mol. When the weight average molecular weight of the alkali-soluble resin is in the above range may have excellent coating properties and developability.
[B] 불포화성에틸렌계모노머[B] Unsaturated Ethylene Monomer
본 발명에서는 사용된 불포화성 에틸렌계모노머는 아크릴모노머로서, 단관능, 2관능, 또는 3관능이상의 (메타)아크릴레이트와의 중합성이 양호하고, 노광시 노광수축율이 낮아 고온다습 조건에서도 밀착력이 개선된다는 관점에서 바람직하다. 이러한 단관능, 2관능, 또는 3관능 이상의 (메타)아크릴레이트는 단독으로 또는 조합하여 사용된다.In the present invention, the unsaturated ethylenic monomer used is an acrylic monomer, which has good polymerization property with mono-, bi-, or tri- or more (meth) acrylates, and has low adhesion shrinkage during exposure, so that the adhesion strength is high even at high temperature and high humidity conditions. It is preferable from the viewpoint of improving. Such mono-, bi-, or tri- or higher (meth) acrylates are used alone or in combination.
하기 b-1) 화학식 1로 표시되는 불포화성 에틸렌계모노머를 포함하여 높은 잔막율을 유지하면서 패턴현상성이 우수한 효과를 얻을 수 있다. B-1) Including an unsaturated ethylenic monomer represented by Formula 1, it is possible to obtain an excellent pattern developability while maintaining a high residual film ratio.
<화학식 1><Formula 1>
상기 화학식 1에서, R은탄소원자수 1 내지 6인알킬기, 지방족 탄화수소기 또는 페닐기이다.In Formula 1, R is an alkyl group having 1 to 6 carbon atoms, an aliphatic hydrocarbon group or a phenyl group.
이를 구체적으로 설명하면, 기존의 다관능 불포화성 에틸렌계모노머를 갖는 감광성 수지 조성물은 패턴현상성을 향상시키기 위해 함량을 줄이면 잔막율이 떨어지는 문제점이 발생하였고, 잔막율을 높이기 위해 함량을 높이면 패턴현상성이 떨어지는 문제가 있었는데, 본 발명에서는 화학식 1의 불포화성 에틸렌계모노머를 적용하여 우수한 잔막율은 유지하면서 패턴현상성을 개선하는 효과를 얻을 수 있었다.In detail, the conventional photosensitive resin composition having a polyfunctional unsaturated ethylenic monomer had a problem that the residual film rate decreased when the content was decreased to improve the pattern developability, and the pattern development occurred when the content was increased to increase the residual film rate. There was a problem of poor properties, in the present invention by applying the unsaturated ethylenic monomer of formula (1) was able to obtain the effect of improving the pattern development while maintaining the excellent residual film ratio.
상기 b-1) 화학식 1로 표시되는 불포화성 에틸렌계모노머는 중량평균 분자량이 100 내지 2,000g/mol인 것이 바람직하다. 상기 중량평균 분자량이 100g/mol 미만인 경우, 내열성, 잔막율이 저하되는 문제점이 있고, 2,000g/mol을 초과하는 경우에는 코팅성, 해상도가 떨어지는 문제가 있다.The unsaturated ethylene monomer represented by b-1) formula (1) preferably has a weight average molecular weight of 100 to 2,000 g / mol. If the weight average molecular weight is less than 100g / mol, there is a problem that the heat resistance, the residual film ratio is lowered, and when the weight average molecular weight exceeds 2,000g / mol, there is a problem of poor coating properties, resolution.
또한, 상기 b-1 화학식 1로 표시되는 불포화성 에틸렌계모노머는 [B] 불포화성 에틸렌계모노머 중에 5내지 50 중량%로 포함되는 것이 바람직하다. 상기 함량이 3중량% 미만일 경우 밀착력, 해상도가 떨어지고, 50 중량%를 초과하는 경우에는 내열성, 잔막율 등이 떨어지는 단점이 있다. In addition, the unsaturated ethylene monomer represented by b-1 Formula 1 is preferably contained in 5 to 50% by weight in the [B] unsaturated ethylene monomer. If the content is less than 3% by weight, the adhesion, the resolution is lowered, if it exceeds 50% by weight there is a disadvantage that the heat resistance, residual film rate and the like.
상기 b-2) 3관능 이상의 불포화기를 가지는 에틸렌모노머의 예로는 트리스히드록시에틸이소시아뉴레이트트리(메타)아크릴레이트, 트리메틸프로판트리(메타)아크릴레이트, 펜타에리트리톨트리(메타)아크릴레이트, 펜타에리트리톨테트라(메타)아크릴레이트, 디펜타에리트리톨헥사(메타)아크릴레이트 등을 들 수 있다.B-2) Examples of the ethylene monomer having a tri- or higher functional unsaturated group include trishydroxyethyl isocyanate tri (meth) acrylate, trimethyl propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, Pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, etc. are mentioned.
상기 불포화성 에틸렌계모노머는 조성물 전체 함량에 대해 5 내지 60중량% 포함될 수 있으며, 상기 함량 범위 내에 있는 경우 현상내성 및 패턴성을 갖는 효과를 얻을 수 있다.The unsaturated ethylenic monomer may be included in the amount of 5 to 60% by weight based on the total content of the composition, when in the content range it can be obtained the effect having development resistance and pattern resistance.
[C] 광중합개시제[C] photopolymerization initiator
본 발명에 있어서의 광중합개시제란, 노광에 의해 분해 또는 결합을 일으키며 라디칼, 음이온, 양이온 등의 상기 [B] 불포화성 에틸렌계모노머의 중합을 개시할 수 있는 활성종을 발생시키는 화합물을 의미한다. The photoinitiator in the present invention means a compound which causes decomposition or bonding upon exposure and generates active species capable of initiating polymerization of the above-mentioned [B] unsaturated ethylenic monomers such as radicals, anions and cations.
본 발명의 광경화형 수지조성물은 전체 조성 중 0.5 내지 20중량% 되도록 광중합개시제를 포함한다. 그 함량이 0.5중량% 미만이면 하드코팅필름의 감도가 충분하지 않아 현상공정에서 하드코팅필름이 유실되기 쉽고, 현상공정에서 하드코팅필름이 유지된다고 하더라도 충분히 높은 가교밀도를 갖는 하드코팅필름을 얻기 어렵다. 광중합개시제의 함량이 20중량% 초과면 하드코팅필름의 내열성, 평탄화성 등이 저하되기 쉽다. The photocurable resin composition of the present invention comprises a photopolymerization initiator to be 0.5 to 20% by weight of the total composition. If the content is less than 0.5% by weight, the sensitivity of the hard coating film is insufficient, so that the hard coating film is easily lost in the developing process, and even if the hard coating film is maintained in the developing process, it is difficult to obtain a hard coating film having a sufficiently high crosslinking density. . When the content of the photopolymerization initiator is more than 20% by weight, heat resistance, planarization property, etc. of the hard coat film tend to be reduced.
이같은 광중합개시제의 예로는 티옥산톤, 2,4-디에틸티옥산톤, 티옥산톤-4-술폰산, 벤조페논, 4,4'-비스(디에틸아미노)벤조페논, 아세토페논, p-디메틸아미노아세토페논, α_α'-디메톡시아세톡시벤조페논, 2,2'-디메톡시-2-페틸아세토페논, p-메톡시아세토페논, 2-메틸[4-(메틸티오)페닐]-2-모르폴리노-1-프로파논, 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-히드록시시클로헥실페닐케톤등의케톤류안트라퀴논, 1,4-나프토퀴논등의퀴논류 1,3,5-트리스(트리클로로메틸)-s-트리아진, 1,3-비스(트리클로로메틸)-5-(2-클로로페닐)-s-트리아진, 1,3-비스(트리클로로페닐)-s-트리아진, 페나실클로라이드, 트리브로모메틸페닐술폰, 트리스(트리클로로메틸)-s-트리아진 등의 할로겐화합물 디-t-부틸퍼옥사이드 등의 과산화물 2,4,6-트리메틸벤조일디페닐포스핀옥사이드 등의 아실포스핀옥사이드류 등을 들 수 있다. Examples of such photoinitiators include thioxanthone, 2,4-diethylthioxanthone, thioxanthone-4-sulfonic acid, benzophenone, 4,4'-bis (diethylamino) benzophenone, acetophenone, p- Dimethylaminoacetophenone, α_α'-dimethoxyacetoxybenzophenone, 2,2'-dimethoxy-2-petylacetophenone, p-methoxyacetophenone, 2-methyl [4- (methylthio) phenyl] -2 Morpholino-1-propane, 2-benzyl-2-diethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-hydroxy-2-methyl-1-phenylpropane Ketones anthraquinone, 1, 4- naphthoquinone, such as a 1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2- propyl) ketone, and 1-hydroxy cyclohexyl phenyl ketone Quinones 1,3,5-tris (trichloromethyl) -s-triazine, 1,3-bis (trichloromethyl) -5- (2-chlorophenyl) -s-triazine, 1,3 Halogens such as -bis (trichlorophenyl) -s-triazine, phenacyl chloride, tribromomethylphenyl sulfone, and tris (trichloromethyl) -s-triazine And acyl phosphine oxides such as peroxide 2,4,6-trimethylbenzoyldiphenylphosphine oxide, such as a logen compound di-t-butylperoxide.
이러한 광중합개시제는 단독 또는 조합하여 사용할 수 있다.These photoinitiators can be used alone or in combination.
[D] 용매[D] solvent
본 발명에 사용되는 용매로는 공중합체 [A]의 제조시 혹은 조성물의 고형분 및 점도를 유지시킬 수 있는 용매로서 다음과 같은 물질들이 사용가능하다. 구체적으로는, 메탄올, 에탄올 등의 알코올류; 테트라하이드로퓨란, 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르 등의 에테르류; 프로필렌글리콜메틸에테르아세테이트, 프로필렌글리콜에틸에테르아세테이트, 프로펠렌글리콜프로필에테르아세테이트, 프로필렌글리콜부틸에테르아세테이트 등의 프로필렌글리콜알킬에테르아세테이트류 등을 들 수 있다. 이러한 용매가운데에서 용해성, 각 성분과의 반응성 및 도막형성의 편리성의 관점에서 디에틸렌글리콜디메틸에테르, 디에틸렌글리콜디에틸에테르, 프로펠렌글리콜메틸에테르아세테이트류메틸에틸케톤, 시클로헥사논, 4-히드록시-4-메틸-2-펜타난등의케톤류아세트산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 2-히드록시프로피온산의에틸에스테르, 메틸에스테르; 2-히드록시-2-메틸프로피온산의에틸에스테르; 히드록시아세트산의메틸에스테르, 에틸에스테르, 부틸에스테르; 젖산에틸, 젖산프로필, 젖산부틸; 메톡시아세트산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 프로폭시아세트산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 부톡시아세트산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 2-메톡시프로피온산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 2-에톡시프로피온산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 2-부톡시프로피온산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 3-메톡시프로판의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 3-에톡시프로피온산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르; 3-부톡시프로피온산의메틸에스테르, 에틸에스테르, 프로필에스테르, 부틸에스테르등의 에스테르류를 들 수 있다. As the solvent used in the present invention, the following materials can be used in the preparation of the copolymer [A] or as a solvent capable of maintaining the solid content and the viscosity of the composition. Specifically, Alcohol, such as methanol and ethanol; Ethers such as tetrahydrofuran, diethylene glycol dimethyl ether and diethylene glycol diethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, propylene glycol propyl ether acetate, and propylene glycol butyl ether acetate. 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 in such a solvent Methyl esters, ethyl esters, propyl esters and butyl esters of ketone acetic acids such as oxy-4-methyl-2-pentanane; Ethyl ester and methyl ester of 2-hydroxypropionic acid; Ethyl ester of 2-hydroxy-2-methylpropionic acid; Methyl ester of hydroxyacetic acid, ethyl ester, butyl ester; Ethyl lactate, propyl lactate, butyl lactate; Methyl ester of methoxy acetic acid, ethyl ester, propyl ester, butyl ester; Methyl esters, ethyl esters, propyl esters, butyl esters of propoxyacetic acid; Methyl ester of butoxy acetic acid, ethyl ester, propyl ester, butyl ester; Methyl ester of 2-methoxypropionic acid, ethyl ester, propyl ester, butyl ester; Methyl ester, ethyl ester, propyl ester, butyl ester of 2-ethoxypropionic acid; Methyl ester, ethyl ester, propyl ester, butyl ester of 2-butoxypropionic acid; Methyl ester, ethyl ester, propyl ester, butyl ester of 3-methoxypropane; Methyl ester, ethyl ester, propyl ester, butyl ester of 3-ethoxypropionic acid; Ester, such as methyl ester of 3-butoxy propionic acid, ethyl ester, propyl ester, and butyl ester, is mentioned.
또한 상기 용매와 함께 고비등점 용매를 병용한 것도 가능하다. 병용할 수 있는 고비등점 용매로서는, 예를 들면 N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸설폭시드, 벤질에틸에테르 등을 들 수 있다. Moreover, it is also possible to use a high boiling point solvent together with the said solvent. As a high boiling point solvent which can be used together, it is N-methylformamide, N, N-dimethylformamide, N-methylacetamide, N, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, for example. And benzyl ethyl ether.
상기 용매는 코팅시에 평탄성을 향상시킨다는 점에서 조성물 전체 함량에 대해 20 내지 80중량% 포함되는 것이 바람직하다. The solvent is preferably included 20 to 80% by weight relative to the total content of the composition in that it improves the flatness during coating.
이외에 첨가될 수 있는 기타첨가제로는 도포성을 향상하기 위한 계면활성제를 들 수 있다. 계면활성제로는 불소 및 실리콘계 계면활성제를 들 수 있는데, 예를 들면 3M사의 FC-129, FC-170C, FC-430, DIC사의 F-172, F-173, F-183, F-470, F-475, 신에츠실리콘사의 KP322, KP323, KP340, KP341 등을 들 수 있다. 이러한 계면활성제는 [A]알칼리 가용성수지 100 중량부에 대하여, 바람직한 것은 5 중량부 이하, 보다 바람직한 것은 2 중량부 이하의 양으로 사용된다. 계면활성제의 양이 5 중량부를 초과한 경우에는 도포시 거품이 발생하기 쉬워진다.In addition, other additives that may be added include a surfactant for improving applicability. Surfactants include fluorine and silicone-based surfactants, for example, 3M's FC-129, FC-170C, FC-430, DIC's F-172, F-173, F-183, F-470, F -KP322, KP323, KP340, KP341 by Shin-Etsu Silicone, etc. are mentioned. Such surfactant is used in an amount of preferably 5 parts by weight or less, more preferably 2 parts by weight or less, based on 100 parts by weight of the [A] alkali-soluble resin. When the amount of the surfactant exceeds 5 parts by weight, bubbles are likely to occur during application.
또한, 기체와의 밀착성을 향상시키기 위해 접착조제를 사용하는 것도 가능하다. 이와같은 접착조제로는 관능성 실란커플링제가 바람직하게 사용되는데, 예를 들면, 트리메톡시실릴안식향산, 메타크릴록시프로필트리메톡시실란, 비닐트리아세톡시실란, 비닐트리메톡시실란, γ-이소시아네이트프로필트리에톡시실란, γ-글리시독시프로필트리메톡시실란 등을 들 수 있다. 이러한 접착조제는 [A]알칼리 가용성수지 100 중량부에 대하여, 바람직한 것은 20 중량부 이하, 보다 바람직한 것은 10 중량부 이하의 양으로 사용된다. 접착조제의 양이 20 중량부를 초과한 경우에는 내열성이 저하되기 쉽다.It is also possible to use an adhesion aid in order to improve the adhesion with the base. As such an adhesion aid, a functional silane coupling agent is preferably used. For example, trimethoxysilyl benzoic acid, methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane, γ- Isocyanate propyl triethoxysilane, (gamma)-glycidoxy propyl trimethoxysilane, etc. are mentioned. Such adhesion aid is used in an amount of preferably 20 parts by weight or less, more preferably 10 parts by weight or less, based on 100 parts by weight of the [A] alkali-soluble resin. When the amount of the adhesion aid exceeds 20 parts by weight, the heat resistance tends to be lowered.
전술된 하드코팅용 감광성 수지 조성물은 상온에서 3 내지 30cps인 점도를 가지는 것인데, 이는 스핀(Spin) 또는 스핀레스(Spinless) 코팅시 전체적으로 평탄한 도막 즉, 하드코팅필름을 형성할 수 있는 효과를 얻을 수 있는 것이다. The above-mentioned hard coating photosensitive resin composition has a viscosity of 3 to 30 cps at room temperature, which can achieve the effect of forming an overall flat coating, that is, a hard coating film during spin or spinless coating. It is.
본 발명은 다른 관점에서, 상기 하드코팅용 감광성 수지 조성물을 이용하여 형성된 하드코팅필름에 관한 것이다.In another aspect, the present invention relates to a hard coat film formed by using the photosensitive resin composition for hard coating.
본 발명에 따른 하드코팅필름은 전술한 하드코팅용 조성물을 투명기재의 일면 또는 양면에 도포시킨 다음 경화시켜 형성된 하드코팅층을 구비한다. 상기한 본발명에 따른 조성물을 이용하여 제조된 하드코팅필름은 경도, 평탄도, 감도, 내열성, 투명성, 내수성 등이 우수할 뿐만 아니라, 고온고습(85℃, 85% RH, 500hrs) 신뢰성 평가시 밀착력 등을 해결하여 신뢰성을 높일 수 있게 된다.The hard coating film according to the present invention includes a hard coating layer formed by applying the above-described hard coating composition on one side or both sides of a transparent substrate and then curing. The hard coating film prepared using the composition according to the present invention is excellent in hardness, flatness, sensitivity, heat resistance, transparency, water resistance, etc., and at the time of reliability evaluation at high temperature and high humidity (85 ° C., 85% RH, 500hrs). Reliability can be improved by solving adhesion.
상기 투명기재로서는 투명성이 있는 기재이면 사용가능하고, 그 예로, 플라스틱필름, 유리, 투명전극, 실리콘나이트라이드계필름이면 어떤 필름이라도 사용가능하며, 상기 플라스틱필름은 예를 들면, 노르보르넨이나다환노르보르넨계 단량체와 같은 시클로올레핀을 포함하는 단량체의 단위를 갖는 시클로올레핀계유도체, 디아세틸셀룰로오스, 트리아세틸셀룰로오스, 아세틸셀룰로오스부틸레이트, 이소부틸에스테르셀룰로오스, 프로피오닐셀룰로오스, 부티릴셀룰로오스 또는 아세틸프로피오닐셀룰로오스 등에서 선택되는 셀룰로오스, 에틸렌-아세트산비닐공중합체, 폴리에스테르, 폴리스티렌, 폴리아미드, 폴리에테르이미드, 폴리아크릴, 폴리이미드, 폴리에테르술폰, 폴리술폰, 폴리에틸렌, 폴리프로필렌, 폴리메틸펜텐, 폴리염화비닐, 폴리염화비닐리덴, 폴리비닐알콜, 폴리비닐아세탈, 폴리에테르케톤, 폴리에테르에테르케톤, 폴리에테르술폰, 폴리메틸메타아크릴레이트, 폴리에틸렌테레프탈레이트, 폴리부틸렌테레프탈레이트, 폴리에틸렌나프탈레이트, 폴리카보네이트, 폴리우레탄, 에폭시 중에서 선택된 것을 사용할 수 있으며, 미연신 1축 또는 2축 연신필름을 사용할 수 있다.As the transparent substrate, any substrate can be used as long as it is transparent. For example, any film can be used as long as it is a plastic film, glass, a transparent electrode, or a silicon nitride film. The plastic film is, for example, norbornene or polycyclic ring. Cycloolefin derivatives having units of monomers containing cycloolefins such as norbornene monomers, diacetyl cellulose, triacetyl cellulose, acetyl cellulose butyrate, isobutyl ester cellulose, propionyl cellulose, butyryl cellulose or acetyl propionyl Cellulose selected from cellulose, ethylene-vinyl acetate copolymer, polyester, polystyrene, polyamide, polyetherimide, polyacryl, polyimide, polyether sulfone, polysulfone, polyethylene, polypropylene, polymethylpentene, polyvinyl chloride , Polychlorinated Nilidene, polyvinyl alcohol, polyvinyl acetal, polyether ketone, polyether ether ketone, polyether sulfone, polymethyl methacrylate, polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polycarbonate, polyurethane, One selected from the epoxy may be used, and an unstretched uniaxial or biaxially oriented film may be used.
이 중에서 바람직하게는 투명성 및 내열성이 우수한 1축 또는 2축 연신폴리에스테르필름이나, 투명성 및 내열성이 우수하면서필름의대형화에대응할수있는시클로올레핀계유도체필름, 투명성 및 광학적으로 이방성이 없다는 점으로 트리아세틸셀룰로오스필름이 적합하게 사용될 수 있다. Among them, a monoaxial or biaxially stretched polyester film having excellent transparency and heat resistance, but a cycloolefin derivative film capable of coping with a large film while providing transparency and heat resistance, and triacetyl due to its transparency and optical anisotropy Cellulose film can be used suitably.
전술된 유기 절연막용 감광성 수지 조성물은 상온에서 3 내지 50cps인 점도를 가지는 것인데, 이는 스핀(Spin) 또는 스핀레스(Spinless) 코팅시 전체적으로 평탄한 도막 즉, 유기 절연막을 형성할 수 있는 효과를 얻을 수 있는 것이다. The above-described photosensitive resin composition for an organic insulating film has a viscosity of 3 to 50 cps at room temperature, which can achieve an effect of forming an overall flat coating film, that is, an organic insulating film during spin or spinless coating. will be.
본 발명의 다른 일구현예는 상기 유기 절연막을 포함하는 디스플레이장치인 것이다.Another embodiment of the present invention is a display device including the organic insulating film.
이하 본 발명의 바람직한 실시예 및 비교예를 설명한다. 그러나 하기 한 실시예는 본 발명의 바람직한 일실시예일뿐 본 발명이 하기 한 실시예에 한정되는 것은 아니다. Hereinafter, preferred examples and comparative examples of the present invention will be described. However, one embodiment below is only a preferred embodiment of the present invention and the present invention is not limited to the following embodiment.
<제조예 1>알카리가용성수지제조Preparation Example 1 Alkali Soluble Resin Manufacture
냉각관과 교반기가 구비된 반응용기에 광중합개시제로서 2,2'-아조비스이소부티로니트릴 10중량부를 용매 프로필렌글리콜모노메틸에테르아세테이트 200중량부에 녹였다. 계속해서 스티렌 65중량부, 메타크릴산 15중량부, 메타크릴산글리시딜 20중량부를 투입하고 질소치환한 후 부드럽게 교반을 시작하였다. 용액의 온도를 70℃로 상승시키고, 이 온도를 4시간 동안 유지하여 공중합체를 포함한 중합체용액을 얻었다. 얻어진 중합체용액의 고형분 농도는 35중량%이었다. 이를 알칼리 가용성수지라 하였다.In a reaction vessel equipped with a cooling tube and a stirrer, 10 parts by weight of 2,2'-azobisisobutyronitrile was dissolved in 200 parts by weight of a solvent propylene glycol monomethyl ether acetate as a photopolymerization initiator. Subsequently, 65 parts by weight of styrene, 15 parts by weight of methacrylic acid, and 20 parts by weight of glycidyl methacrylate were added thereto, followed by nitrogen replacement, followed by gentle stirring. The temperature of the solution was raised to 70 ° C., and this temperature was maintained for 4 hours to obtain a polymer solution including a copolymer. Solid content concentration of the obtained polymer solution was 35 weight%. This is called alkali-soluble resin.
<실시예 1 내지 5 및 비교예 1 내지 3><Examples 1 to 5 and Comparative Examples 1 to 3>
감광성물질로서 알카리가용성수지와 용매 로프로필렌글리콜모노메틸에테르아세테이트, 불포화성에틸렌결합을 갖는 모노머(디펜타에리트리톨헥사(메타)아크릴레이트)를 배합하고 여기에 접착조제로 화학식1 구조의 실란화합물을 하기 표 1에 나타낸 바와 같이 함유량을 변화시켜 가면서 배합하여 감광성수지를 제조하였다.As a photosensitive material, an alkali-soluble resin, a solvent, propylene glycol monomethyl ether acetate, and a monomer having an unsaturated ethylene bond (dipentaerythritol hexa (meth) acrylate) are mixed, and a silane compound having the formula (1) structure is used as an adhesion aid. As shown in Table 1 below, the compound was blended with varying content to prepare a photosensitive resin.
[A] alkali soluble resin
(화학식1의모노머)[B] ethylenically unsaturated monomers
Monomer of Formula 1
[B] 6-functional ethylenically unsaturated monomer
[C] oxime photopolymerization initiator
1) 함량단위는중량%이다. 1) The content unit is weight percent.
2) [B] 에틸렌성불포화모노머 (화학식1의모노머)는DPE6A-MS (공영사)이다.2) [B] The ethylenically unsaturated monomer (monomer of Chemical Formula 1) is DPE6A-MS (Cooperative).
3) [B] 6관능에틸렌성불포화모노머는DPHA (교에이사)이다.3) [B] The 6 functional ethylenically unsaturated monomer is DPHA (Gyoei Co., Ltd.).
4) [C]옥심계광중합개시제 OXE-01(바스프)이다.
4) [C] oxime photopolymerization initiator OXE-01 (BASF).
상기 실시예 및 비교예에서 제조된 조성물에 대하여 다음과 같이 물성평가하였으며, 그 결과를 하기 표 2에 나타내었다.The physical properties of the compositions prepared in Examples and Comparative Examples were evaluated as follows, and the results are shown in Table 2 below.
(1) 평탄성(1) flatness
컬러레지스트가 패턴닝된 Glass에 제조된 각각의 감광성 수지 조성물을 스핀코팅하고 핫플레이트에서 100℃, 120초의 조건으로 예비건조를 행하여 막두께 3㎛의 포토레지스트막을 형성하였다, 이러한 막이 형성된 Glass를 노광한 후 2.38%TMAH 수용액에 60초간 현상하고 다시 220℃, 1시간 동안 강한 열처리를 실시하였다. 여기서 얻어진 건조 도막의 5point의 두께를 측정하여 평탄성을 측정하였다.Each photosensitive resin composition prepared on the glass patterned with color resist was spin-coated and pre-dried at a temperature of 100 ° C. for 120 seconds on a hot plate to form a photoresist film having a thickness of 3 μm. After developing for 60 seconds in a 2.38% TMAH aqueous solution and again subjected to strong heat treatment for 220 ℃, 1 hour. The thickness of 5 points of the dry coating film obtained here was measured, and flatness was measured.
상기 평탄성을 측정하여 두께편차가 0.025㎛미만인 경우 ◎, 0.026㎛~0.05㎛인 경우를 ○, 0.06㎛~0.1㎛인 경우를 △, 0.1㎛초과인 경우를 X로 나타내었다.The flatness was measured to indicate that the thickness deviation was less than 0.025 µm,?, 0.026 µm to 0.05 µm,?, 0.06 µm to 0.1 µm, and? And 0.1 µm, respectively.
(2) 감도(2) sensitivity
Glass에 제조된 각각의 감광성 수지 조성물을 스핀 800rpm으로 코팅하고 핫플레이트에서 100℃, 120초의 조건으로 예비건조를 행하고 노광량을 60, 70, 80, 90, 30, 60, 90mJ/㎠의 조건으로 각각 노광을 실시한 후 2.38%TMAH 수용액에 60초간 현상하고 다시 220℃, 1시간 동안 강한 열처리를 실시하였다. 이때 얻어진 도막의 두께를 측정하였다.Each photosensitive resin composition prepared in Glass was coated with a spin of 800 rpm, pre-dried at a temperature of 100 ° C. and 120 seconds on a hot plate, and the exposure dose was set at 60, 70, 80, 90, 30, 60, 90 mJ / cm 2, respectively. After exposure, the solution was developed in a 2.38% TMAH aqueous solution for 60 seconds, and then subjected to a strong heat treatment at 220 ° C. for 1 hour. The thickness of the coating film obtained at this time was measured.
상기 두께를 측정하여 90mJ/㎠에서 얻어진 도막의 두께 대비 90% 이상을 얻은 것을 각 조성에서 감도로 선택하였다.The thickness was measured to obtain 90% or more of the thickness of the coating film obtained at 90 mJ / cm 2 as the sensitivity in each composition.
(3) 내열성(3) heat resistance
상기 감도측정에서 형성된 패턴막의 상,하, 좌, 우의 폭을 측정하였다. 이때 각의 변화율이 미드베이크(100℃, 2분)전 기준, 0~10%인 경우를 ◎, 11~20% 인 경우를 ○, 21~40%인 경우를 △, 40% 초과인 경우를 X로 나타내었다.The widths of the top, bottom, left and right sides of the pattern film formed by the sensitivity measurement were measured. At this time, when the change rate of each angle is 0 to 10%, ◎, 11 to 20%, ○, 21 to 40%, and △, 40% or more, before the mid-baking (100 ° C, 2 minutes) It is represented by X.
(4) 밀착성(4) adhesion
Glass에 제조된 각각의 감광성 수지 조성물을 스핀 800rpm으로 코팅하고 핫플레이트에서 100℃, 120초의 조건으로 예비건조를 행하고 패턴사이즈별(4㎛ - 100㎛) 마스크를 사용하고 노광량을 50mJ/㎠으로 노광한 후 2.38%TMAH 수용액에 60초간 현상하고 다시 220℃, 1시간 동안 강한 열처리를 실시하였다. 이때 유실되지 않고 남아 있는 최소 패턴사이즈를 확인하였다.Each photosensitive resin composition prepared in Glass was coated with a spin of 800 rpm, pre-dried at 100 ° C. for 120 seconds on a hot plate, using a mask according to pattern size (4 μm to 100 μm), and the exposure amount was exposed at 50 mJ / cm 2. After developing for 60 seconds in a 2.38% TMAH aqueous solution and again subjected to strong heat treatment for 220 ℃, 1 hour. At this time, the minimum pattern size remaining without loss was confirmed.
상기 측정에서 유실되지 않고 남아있는 최소 패턴사이즈가 5㎛이하 인 경우를 ◎, 6~10㎛인 경우를 ○, 11~15㎛인 경우를 △, 15㎛ 초과인 경우를 X로 나타내었다.The case where the minimum pattern size remaining without loss in the above measurement is 5 µm or less,?, 6-10 µm,?, 11-15 µm,?, And 15 µm are represented by X.
(5) 투과율(5) transmittance
투과도는 분광광도계를 이용하여 400nm에서의 투과율을 측정하였다.The transmittance | permeability measured the transmittance | permeability in 400 nm using the spectrophotometer.
(6) 패턴현상성(6) pattern developability
Glass에 제조된 각각의 감광성 수지 조성물을 스핀 800rpm으로 코팅하고 핫플레이트에서 100℃, 120초의 조건으로 예비건조를 행하고 패턴사이즈별(4㎛ - 100㎛) 마스크를 사용하고 노광량을 50mJ/㎠으로 노광한 후 2.38%TMAH 수용액에 60초간 현상하고 다시 220℃, 1시간 동안 강한 열처리를 실시하였다. 이때 깨끗하게 얻어진 도막의 최소 패턴사이즈를 측정하였다.Each photosensitive resin composition prepared in Glass was coated with a spin of 800 rpm, pre-dried at 100 ° C. for 120 seconds on a hot plate, using a mask according to pattern size (4 μm to 100 μm), and the exposure amount was exposed at 50 mJ / cm 2. After developing for 60 seconds in a 2.38% TMAH aqueous solution and again subjected to strong heat treatment for 220 ℃, 1 hour. At this time, the minimum pattern size of the coating film obtained clearly was measured.
(7) 잔막율(7) residual film rate
Glass에 제조된 각각의 감광성 수지 조성물을 스핀코팅하고 핫플레이트에서 100℃, 120초의 조건으로 예비건조를 행하여 막 두께 3㎛의 포토레지스트막을 형성하였다, 이러한 막이 형성된 Glass를 노광한 후 2.38%TMAH 수용액에 60초간 현상하고 다시 220℃, 1시간 동안 강한 열처리를 실시하였다. 예비건조시의 막두께와 후경화를 통한 용매 제거 후의 형성된 막의 두께를 측정하여 비율측정을 통하여 잔막율을 측정하였다. Each photosensitive resin composition prepared in Glass was spin-coated and pre-dried at a temperature of 100 ° C. for 120 seconds on a hot plate to form a photoresist film having a thickness of 3 μm. After developing for 60 seconds and again subjected to strong heat treatment for 220 ℃, 1 hour. The film thickness during predrying and the thickness of the formed film after solvent removal through post-cure were measured, and the residual film rate was measured by ratio measurement.
점도
(cps)Composition
Viscosity
(cps)
(mJ/㎠)Sensitivity
(mJ / ㎠)
(㎛)Pattern development
(Μm)
(%)Residual rate
(%)
(%)Transmittance
(%)
상기 표 2를 통하여 본 발명에 따라 실시예 1 ~ 5에서 제조한 감광성 수지 조성물은 평탄도, 감도, 내열성, 투명성, 잔막율 등이 우수하였고, 특히 패턴현상성이 우수하면서도 기판과의 밀착성이 우수한 결과를 얻었다.The photosensitive resin composition prepared in Examples 1 to 5 according to the present invention through Table 2 was excellent in flatness, sensitivity, heat resistance, transparency, residual film ratio, etc., in particular, excellent pattern developability and excellent adhesion to the substrate The result was obtained.
본 발명의 단순한 변형 또는 변경은 모두 이 분야의 통상의 지식을 가진 자에 의하여 용이하게 실시될 수 있으며 이러한 변형이나 변경은 모두 본 발명의 영역에 포함되는 것으로 볼 수 있다.All simple modifications or changes of the present invention can be easily carried out by those skilled in the art, and all such modifications or changes can be seen to be included in the scope of the present invention.
Claims (8)
<화학식 1>
상기 화학식 1에서, R은 탄소원자수 1 내지 6인 알킬기, 지방족 탄화수소기 또는 페닐기이다.[A] alkali-soluble resin, [B] unsaturated ethylenic monomer, [C] photoinitiator and [D] solvent, wherein the [B] unsaturated unsaturated monomer is represented by b-1) Photosensitive resin composition for organic insulating films containing unsaturated ethylene monomer and b-2) ethylene monomer which has a trifunctional or more than trifunctional unsaturated group
<Formula 1>
In Formula 1, R is an alkyl group having 1 to 6 carbon atoms, an aliphatic hydrocarbon group or a phenyl group.
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