KR20230104426A - Photosensitive resin composition comprising two or more oxime ester fluorene derivative compounds as photoinitiator component - Google Patents
Photosensitive resin composition comprising two or more oxime ester fluorene derivative compounds as photoinitiator component Download PDFInfo
- Publication number
- KR20230104426A KR20230104426A KR1020210194046A KR20210194046A KR20230104426A KR 20230104426 A KR20230104426 A KR 20230104426A KR 1020210194046 A KR1020210194046 A KR 1020210194046A KR 20210194046 A KR20210194046 A KR 20210194046A KR 20230104426 A KR20230104426 A KR 20230104426A
- Authority
- KR
- South Korea
- Prior art keywords
- alkyl
- resin composition
- photosensitive resin
- meth
- acrylate
- Prior art date
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- -1 oxime ester fluorene derivative compounds Chemical class 0.000 title claims abstract description 108
- 239000011342 resin composition Substances 0.000 title claims abstract description 42
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 16
- 125000006736 (C6-C20) aryl group Chemical group 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 12
- 239000011230 binding agent Substances 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 229920000058 polyacrylate Polymers 0.000 claims description 7
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005561 phenanthryl group Chemical group 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 claims description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 2
- 239000010409 thin film Substances 0.000 abstract description 21
- 238000000206 photolithography Methods 0.000 abstract description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 73
- 239000000203 mixture Substances 0.000 description 23
- 239000010408 film Substances 0.000 description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 8
- 239000004094 surface-active agent Substances 0.000 description 8
- 238000007259 addition reaction Methods 0.000 description 7
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 7
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 7
- 229920002120 photoresistant polymer Polymers 0.000 description 7
- FKRCODPIKNYEAC-UHFFFAOYSA-N propionic acid ethyl ester Natural products CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- 239000000853 adhesive Substances 0.000 description 6
- 230000001070 adhesive effect Effects 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 6
- 239000011976 maleic acid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 5
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 4
- 229940017219 methyl propionate Drugs 0.000 description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 3
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 3
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 3
- DABFKTHTXOELJF-UHFFFAOYSA-N 1-propylpyrrole-2,5-dione Chemical compound CCCN1C(=O)C=CC1=O DABFKTHTXOELJF-UHFFFAOYSA-N 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 3
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 3
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 229920006243 acrylic copolymer Polymers 0.000 description 3
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 3
- 125000005907 alkyl ester group Chemical group 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000018109 developmental process Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 230000035945 sensitivity Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 2
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- SXPVZPQNFIDDPP-UHFFFAOYSA-N 3-(4-hydroxyphenyl)pyrrole-2,5-dione Chemical compound C1=CC(O)=CC=C1C1=CC(=O)NC1=O SXPVZPQNFIDDPP-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 229940022663 acetate Drugs 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000008366 benzophenones Chemical class 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012986 chain transfer agent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003822 epoxy resin Substances 0.000 description 2
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 2
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 2
- ZWRUINPWMLAQRD-UHFFFAOYSA-N nonan-1-ol Chemical compound CCCCCCCCCO ZWRUINPWMLAQRD-UHFFFAOYSA-N 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 229920000647 polyepoxide Polymers 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
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000007261 regionalization Effects 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 2
- 150000003918 triazines Chemical class 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DAFHKNAQFPVRKR-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylpropanoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)C DAFHKNAQFPVRKR-UHFFFAOYSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
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Abstract
본 발명은 광개시제 성분으로서 2종 이상의 옥심에스테르 플루오렌 유도체 화합물을 포함하는 감광성 수지 조성물에 관한 것으로, 보다 상세하게는, 광개시제 성분으로서 구조적으로 상이한 옥심에스테르 플루오렌 유도체 화합물 2종 이상의 조합을 포함함으로써, 두께가 높은 박막에서 우수한 심부 경화성을 나타내어 박막의 경화도 증가 및 패턴의 접착성과 직진성을 향상시켜 포토리소그래피법에 유리한 특성을 가지고, 수용성 기반 용액으로 제거 가능하여 LED, TFT-LCD, MEMS, 반도체 분야에서 적합하게 사용될 수 있는 감광성 수지 조성물에 관한 것이다.The present invention relates to a photosensitive resin composition comprising two or more oxime ester fluorene derivative compounds as a photoinitiator component, and more particularly, as a photoinitiator component, by including a combination of two or more structurally different oxime ester fluorene derivative compounds, It shows excellent deep curing properties in thin films with high thickness, which increases the curing degree of thin films and improves the adhesiveness and straightness of patterns, which is advantageous to photolithography. It relates to a photosensitive resin composition that can be suitably used in
Description
본 발명은 광개시제 성분으로서 2종 이상의 옥심에스테르 플루오렌 유도체 화합물을 포함하는 감광성 수지 조성물에 관한 것으로, 보다 상세하게는, 광개시제 성분으로서 구조적으로 상이한 옥심에스테르 플루오렌 유도체 화합물 2종 이상의 조합을 포함함으로써, 두께가 높은 박막에서 우수한 심부 경화성을 나타내어 박막의 경화도 증가 및 패턴의 접착성과 직진성을 향상시켜 포토리소그래피법에 유리한 특성을 가지고, 수용성 기반 용액으로 제거 가능하여 LED, TFT-LCD, MEMS, 반도체 분야에서 적합하게 사용될 수 있는 감광성 수지 조성물에 관한 것이다.The present invention relates to a photosensitive resin composition comprising two or more oxime ester fluorene derivative compounds as a photoinitiator component, and more particularly, as a photoinitiator component, by including a combination of two or more structurally different oxime ester fluorene derivative compounds, It shows excellent deep curing properties in thin films with high thickness, which increases the curing degree of thin films and improves the adhesiveness and straightness of patterns, which is advantageous to photolithography. It relates to a photosensitive resin composition that can be suitably used in
감광성 조성물은 일반적으로 바인더 수지, 불포화 결합을 갖는 중합성 화합물, 광중합 개시제, 용매 및 기타 첨가제들을 포함하며, 기판상에 도포되어 도막을 형성하고, 이 도막의 특정 부분에 포토마스크 등을 이용하여 광 조사에 의한 노광을 실시한 후, 비 노광부를 현상 처리하여 제거함으로써 패턴을 형성하는데 사용될 수 있다. 이러한 감광성 조성물은 광을 조사하여 경화시키는 것이 가능하므로, 광경화성 잉크, 감광성 인쇄판, 각종 포토레지스트, LCD용 포토레지스트 또는 투명 감광제 등에 사용될 수 있다. A photosensitive composition generally includes a binder resin, a polymerizable compound having an unsaturated bond, a photopolymerization initiator, a solvent, and other additives, and is applied on a substrate to form a coating film, and a photomask is used on a specific portion of the coating film to form a photosensitive composition. After performing exposure by irradiation, it can be used to form a pattern by removing the non-exposed portion by developing. Since such a photosensitive composition can be cured by irradiation with light, it can be used as a photocurable ink, a photosensitive printing plate, various photoresists, a photoresist for LCD, or a transparent photoresist.
감광성 조성물에서 광개시제는 불포화 결합을 갖는 바인더 또는 중합성 화합물과 결합하여 경화를 하게 되고, 이로 인한 박막 또는 패턴에 대한 강도를 가지게 하여, 공정 과정에 박막의 손실 또는 떨어지는 것을 막아주는 역할을 한다. In the photosensitive composition, the photoinitiator is cured by being combined with a binder or polymerizable compound having an unsaturated bond, thereby providing strength to the thin film or pattern, and preventing loss or falling of the thin film during the process.
일반적으로, 감광성 조성물은 수십 마이크론(μm) 두께의 코팅막으로 형성되는데, 광개시제의 종류에 따른 박막의 경화도 차이가 발생하게 된다. 따라서 패턴의 하부에 들어가는 빛의 차이가 생기게 되고, 이로 인하여 패턴의 모양에 차이가 발생하게 된다. 이러한 차이를 조절하기 위해서 상이한 2종의 광개시제를 이용하여 패턴 모양을 조절할 수 있으며, 이를 통해 우수한 직진성을 갖는 패턴을 형성할 수 있다. In general, the photosensitive composition is formed as a coating film having a thickness of several tens of microns (μm), and a difference in curing degree of the thin film occurs depending on the type of photoinitiator. Therefore, a difference in light entering the lower part of the pattern occurs, and this causes a difference in the shape of the pattern. In order to control this difference, the pattern shape can be adjusted using two different types of photoinitiators, and through this, a pattern having excellent straightness can be formed.
일반적으로 옥심에스테르 플루오렌 유도체 화합물을 단독으로 포함하는 감광성 조성물의 경우, 수십 마이크론(μm) 두께의 박막에서는 빛이 심부까지 들어가지 않아 박막 하부의 경화도가 줄어드는 단점을 가지고 있으며, 박막 하부까지 경화도를 증가시키기 위해서 옥심에스테르 플루오렌 유도체 화합물의 사용량을 줄이면, 박막 전체에 감도가 부족하여 포토레지스트를 이용한 패턴 형성시 패턴의 크기가 작거나 접착력이 떨어지는 단점을 가지고 있다. In general, in the case of a photosensitive composition containing an oxime ester fluorene derivative compound alone, light does not penetrate deep into a thin film with a thickness of several tens of microns (μm), so the curing degree of the lower part of the thin film is reduced. If the amount of the oxime ester fluorene derivative compound is reduced in order to increase the sensitivity of the entire thin film, there is a disadvantage in that the size of the pattern is small or the adhesion is poor when forming a pattern using a photoresist.
이러한 단점을 극복하기 위해서, 옥심에스테르 플루오렌 유도체 화합물을 소량 사용하고 아세토페논 유도체, 벤조페논 유도체, 트리아진 유도체, 비이미다졸 유도체, 아실포스핀 옥사이드 유도체등을 함께 사용하여 경화도를 향상시키고 있다. 하지만 옥심에스테르 플루오렌 유도체 대비 아세토페논 유도체, 벤조페논 유도체, 트리아진 유도체, 비이미다졸 유도체, 아실포스핀 옥사이드 유도체등의 광개시제는 감도가 많이 떨어지기 때문에 과량의 광개시제를 사용해야만 경화도를 확보할 수 있는 단점을 가지고 있다.In order to overcome these disadvantages, a small amount of oxime ester fluorene derivative compound is used, and acetophenone derivative, benzophenone derivative, triazine derivative, biimidazole derivative, and acylphosphine oxide derivative are used together to improve the degree of curing. However, compared to oxime ester fluorene derivatives, photoinitiators such as acetophenone derivatives, benzophenone derivatives, triazine derivatives, biimidazole derivatives, and acylphosphine oxide derivatives are less sensitive. has a downside.
따라서, 감도가 우수한 옥심에스테르 플루오렌 유도체 화합물을 비교적 소량으로 사용하면서도, 두께가 높은 박막에 대해서 우수한 심부 경화성을 나타낼 수 있는 기술의 개발이 요청되고 있다.Therefore, there is a demand for development of a technique capable of exhibiting excellent deep curing properties for a thin film having a high thickness while using a relatively small amount of an oxime ester fluorene derivative compound having excellent sensitivity.
본 발명의 목적은 두께가 높은 박막에 대해서도 우수한 심부 경화성을 나타내어 직진성이 우수한 패턴을 형성시킬 수 있으며, 패턴의 접착력 또한 향상시킬 수 있는 감광성 수지 조성물을 제공하는 것이다.An object of the present invention is to provide a photosensitive resin composition capable of forming a pattern with excellent straightness by exhibiting excellent deep curing properties even for a thin film having a high thickness, and improving the adhesive strength of the pattern.
상기한 목적을 달성하고자 본 발명은, 광개시제 성분으로서 하기 화학식 1로 표시되는 옥심에스테르 플루오렌 유도체 화합물 2종 이상; 바인더; 및 광중합성 화합물;을 포함하는, 감광성 수지 조성물을 제공한다:In order to achieve the above object, the present invention, as a photoinitiator component, two or more oxime ester fluorene derivative compounds represented by the following formula (1); bookbinder; And a photopolymerizable compound; provides a photosensitive resin composition comprising:
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R3는 각각 독립적으로 수소, 할로겐, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬 또는 (C3-C20)사이클로알킬이고;R 1 to R 3 are each independently selected from hydrogen, halogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy( C1-C20)alkyl, hydroxy(C1-C20)alkoxy(C1-C20)alkyl or (C3-C20)cycloalkyl;
A는 수소, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬, (C3-C20)사이클로알킬, 아미노, 니트로, 시아노 또는 히드록시이고; A is hydrogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy (C1-C20)alkyl, hydroxy( C1-C20)alkoxy(C1-C20)alkyl, (C3-C20)cycloalkyl, amino, nitro, cyano or hydroxy;
n은 0 또는 1이다.n is 0 or 1;
본 발명의 다른 측면에 따르면, 상기 감광성 수지 조성물로부터 형성된 경화막이 제공된다.According to another aspect of the present invention, a cured film formed from the photosensitive resin composition is provided.
본 발명의 또 다른 측면에 따르면, 상기 경화막을 포함하는 전자 소자(예컨대, LED, TFT-LCD, MEMS, 반도체 소자 등)가 제공된다.According to another aspect of the present invention, an electronic device (eg, LED, TFT-LCD, MEMS, semiconductor device, etc.) including the cured film is provided.
본 발명에 따른 감광성 수지 조성물은, 두께가 높은(예컨대, 5㎛ 이상) 박막에 대해서도 접착성과 직진성이 우수한 패턴을 형성시킬 수 있으며, 패턴 형성시 낮은 노광량에서도 접착력이 양호할 뿐만 아니라 패턴의 직진성이 우수한 특성을 제공할 수 있있다.The photosensitive resin composition according to the present invention can form a pattern with excellent adhesiveness and straightness even for a thin film having a high thickness (eg, 5 μm or more), and has good adhesiveness even at a low exposure amount during pattern formation, and the straightness of the pattern It can provide excellent characteristics.
본 명세서에 기재된 “알킬”, “알콕시” 및 그 외 “알킬”부분을 포함하는 치환체는 직쇄 또는 분쇄 형태를 모두 포함하고, “사이클로알킬”은 단일 고리계뿐만 아니라 다중 고리계 탄화수소도 포함한다. 또한, 본 명세서에 기재된 “아릴”은 하나의 수소 제거에 의해서 방향족 탄화수소로부터 유도된 유기 라디칼로, 각 고리에 적절하게는 4 내지 7개, 바람직하게는 5 또는 6개의 고리원자를 포함하는 단일 또는 융합고리계를 포함하며, 다수개의 아릴이 단일결합으로 연결되어 있는 형태까지 포함한다. 또한, 본 명세서에 기재된 “히드록시알킬”은 상기에서 정의된 알킬기에 히드록시기가 결합된 OH-알킬을 의미하며, “히드록시알콕시알킬”은 상기 히드록시알킬기에 알콕시기가 결합된 히드록시알킬-O-알킬을 의미한다.Substituents including "alkyl", "alkoxy" and other "alkyl" moieties described herein include both straight-chain and branched forms, and "cycloalkyl" includes both single-ring and multi-ring hydrocarbons. In addition, “aryl” as described herein is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and each ring has 4 to 7, preferably 5 or 6 ring atoms, and is a single or It includes a fused ring system, and even includes a form in which a plurality of aryls are connected by single bonds. In addition, “hydroxyalkyl” described herein means OH-alkyl in which a hydroxy group is bonded to the above-defined alkyl group, and “hydroxyalkoxyalkyl” is a hydroxyalkyl-O in which an alkoxy group is bonded to the hydroxyalkyl group -means alkyl.
또한 본 명세서에서, 용어 “(메트)아크릴”은 “아크릴” 및 “메타크릴”을 모두 포함하는 개념으로 사용된다.Also, in this specification, the term “(meth)acryl” is used as a concept including both “acryl” and “methacryl”.
이하에서 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
본 발명의 감광성 수지 조성물은, 광개시제 성분으로서 하기 화학식 1로 표시되는 옥심에스테르 플루오렌 유도체 화합물 2종 이상을 포함한다:The photosensitive resin composition of the present invention includes two or more oxime ester fluorene derivative compounds represented by the following formula (1) as a photoinitiator component:
[화학식 1][Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R3는 각각 독립적으로 수소, 할로겐, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬 또는 (C3-C20)사이클로알킬이고;R 1 to R 3 are each independently selected from hydrogen, halogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy( C1-C20)alkyl, hydroxy(C1-C20)alkoxy(C1-C20)alkyl or (C3-C20)cycloalkyl;
A는 수소, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬, (C3-C20)사이클로알킬, 아미노, 니트로, 시아노 또는 히드록시이고; A is hydrogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy (C1-C20)alkyl, hydroxy( C1-C20)alkoxy(C1-C20)alkyl, (C3-C20)cycloalkyl, amino, nitro, cyano or hydroxy;
n은 0 또는 1이다.n is 0 or 1;
보다 구체적으로, 이에 한정되지는 않으나,More specifically, but not limited to,
상기 (C1-C20)알킬기는 (C1-C10)알킬이고, 보다 더 구체적으로는 (C1-C6)알킬이며;The (C1-C20)alkyl group is (C1-C10)alkyl, more specifically (C1-C6)alkyl;
상기 (C6-C20)아릴기는 (C6-C18)아릴이고;The (C6-C20) aryl group is a (C6-C18) aryl;
상기 (C1-C20)알콕시기는 (C1-C10)알콕시이고, 보다 더 구체적으로는 (C1-C4)알콕시이며;The (C1-C20) alkoxy group is (C1-C10) alkoxy, more specifically (C1-C4) alkoxy;
상기 (C6-C20)아릴(C1-C20)알킬기는 (C6-C18)아릴(C1-C10)알킬이고, 보다 더 구체적으로는 (C6-C18)아릴(C1-C6)알킬이며,The (C6-C20) aryl (C1-C20) alkyl group is (C6-C18) aryl (C1-C10) alkyl, more specifically (C6-C18) aryl (C1-C6) alkyl,
상기 히드록시(C1-C20)알킬기는 히드록시(C1-C10)알킬이고, 보다 더 구체적으로는 히드록시(C1-C6)알킬이며;The hydroxy (C1-C20) alkyl group is hydroxy (C1-C10) alkyl, more specifically hydroxy (C1-C6) alkyl;
상기 히드록시(C1-C20)알콕시(C1-C20)알킬기는 히드록시(C1-C10)알콕시(C1-C10)알킬이고, 보다 더 구체적으로는 히드록시(C1-C4)알콕시(C1-C6)알킬이며;The hydroxy (C1-C20) alkoxy (C1-C20) alkyl group is hydroxy (C1-C10) alkoxy (C1-C10) alkyl, more specifically, hydroxy (C1-C4) alkoxy (C1-C6) alkyl;
상기 (C3-C20)사이클로알킬기는 (C3-C10)사이클로알킬이다.The (C3-C20)cycloalkyl group is a (C3-C10)cycloalkyl.
일 구체예에 따르면, 상기 화학식 1에서,According to one embodiment, in Formula 1,
R1 내지 R3는 각각 독립적으로 수소, 브로모, 클로로, 아이오도, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, n-펜틸, i-펜틸, n-헥실, i-헥실, 페닐, 나프틸, 바이페닐, 터페닐, 안트릴, 인데닐, 페난트릴, 메톡시, 에톡시, n-프로필옥시, i-프로필옥시, n-부톡시, i-부톡시, t-부톡시, 히드록시메틸, 히드록시에틸, 히드록시n-프로필, 히드록시n-부틸, 히드록시i-부틸, 히드록시n-펜틸, 히드록시i-펜틸, 히드록시n-헥실, 히드록시i-헥실, 히드록시메톡시메틸, 히드록시메톡시에틸, 히드록시메톡시프로필, 히드록시메톡시부틸, 히드록시에톡시메틸, 히드록시에톡시에틸, 히드록시에톡시프로필, 히드록시에톡시부틸, 히드록시에톡시펜틸 또는 히드록시에톡시헥실이고;R 1 to R 3 are each independently hydrogen, bromo, chloro, iodo, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, n-pentyl, i-pentyl , n-hexyl, i-hexyl, phenyl, naphthyl, biphenyl, terphenyl, anthryl, indenyl, phenanthryl, methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy, i-butoxy, t-butoxy, hydroxymethyl, hydroxyethyl, hydroxyn-propyl, hydroxyn-butyl, hydroxyi-butyl, hydroxyn-pentyl, hydroxyi-pentyl, hydroxy n-hexyl, hydroxyi-hexyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxy propyl, hydroxyethoxybutyl, hydroxyethoxypentyl or hydroxyethoxyhexyl;
A는 수소, 메틸, 에틸, n-프로필, i-프로필, n-부틸, i-부틸, t-부틸, 페닐, 나프틸, 바이페닐, 터페닐 안트릴, 인데닐, 페난트릴, 메톡시, 에톡시, 프로판옥시, 부톡시, 히드록시메틸, 히드록시에틸, 히드록시프로필, 히드록시부틸, 히드록시메톡시메틸, 히드록시메톡시에틸, 히드록시메톡시프로필, 히드록시메톡시부틸, 히드록시에톡시메틸, 히드록시에톡시에틸, 히드록시에톡시프로필, 히드록시에톡시부틸, 아미노, 니트로, 시아노 또는 히드록시일 수 있으나, A is hydrogen, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, t-butyl, phenyl, naphthyl, biphenyl, terphenyl anthryl, indenyl, phenanthryl, methoxy, Ethoxy, propanoxy, butoxy, hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl, hydroxymethoxymethyl, hydroxymethoxyethyl, hydroxymethoxypropyl, hydroxymethoxybutyl, hydroxy hydroxyethoxymethyl, hydroxyethoxyethyl, hydroxyethoxypropyl, hydroxyethoxybutyl, amino, nitro, cyano or hydroxy;
이에 한정되지는 않는다.It is not limited to this.
일 구체예에서, 상기 화학식 1로 표시되는 옥심에스테르 플루오렌 유도체 화합물로는 대표적으로 하기의 화합물들을 들 수 있으나, 이에 한정되지는 않는다.In one embodiment, examples of the oxime ester fluorene derivative compound represented by Formula 1 include the following compounds, but are not limited thereto.
본 발명의 감광성 수지 조성물에 광개시제 성분으로서 포함되는 상기 화학식 1로 표시되는 옥심에스테르 플루오렌 유도체 화합물들은 2종 이상이며, 보다 구체적으로는 2종 내지 4종, 보다 더 구체적으로는 2종 또는 3종, 보다 더 구체적으로는 2종일 수 있다.The oxime ester fluorene derivative compounds represented by Formula 1 included as a photoinitiator component in the photosensitive resin composition of the present invention are two or more, more specifically two to four, more specifically two or three , More specifically, it may be two types.
일 구체예에서, 본 발명의 감광성 수지 조성물에 포함되는 화학식 1의 옥심에스테르 플루오렌 유도체 화합물들의 총량은, 조성물 100 중량부를 기준으로, 0.01 내지 10 중량부일 수 있다. 조성물 내의 화학식 1의 옥심에스테르 플루오렌 유도체 화합물들의 총 함량이 상기 수준보다 지나치게 적으면 낮은 감도로 인하여 잔막율이 나빠지고 패턴 형성에 어려움이 있을 수 있고, 반대로 상기 수준보다 지나치게 적으면 조성물의 보존 안정성에 문제가 발생할 수 있고, 광개시제의 용해도 감소로 인하여 박막 표면에 이물질을 발생시킬 수 있다.In one embodiment, the total amount of the oxime ester fluorene derivative compounds of Formula 1 included in the photosensitive resin composition of the present invention may be 0.01 to 10 parts by weight based on 100 parts by weight of the composition. If the total content of the oxime ester fluorene derivative compounds of Formula 1 in the composition is too less than the above level, the film remaining rate deteriorates due to low sensitivity and there may be difficulty in pattern formation, conversely, if it is too less than the above level, the storage stability of the composition problems may occur, and foreign substances may be generated on the surface of the thin film due to the decrease in solubility of the photoinitiator.
보다 구체적으로, 본 발명의 감광성 수지 조성물 100 중량부에 포함되는 화학식 1의 옥심에스테르 플루오렌 유도체 화합물들의 총량은, 예컨대, 0.01 중량부 이상, 0.05 중량부 이상, 0.1 중량부 이상, 0.5 중량부 이상, 1 중량부 이상, 2 중량부 이상, 3 중량부 이상 또는 4 중량부 이상일 수 있고, 또한 10 중량부 이하, 9.5 중량부 이하, 9 중량부 이하, 8.5 중량부 이하 또는 8 중량부 이하일 수 있으나, 이에 한정되지 않는다.More specifically, the total amount of oxime ester fluorene derivative compounds of Formula 1 included in 100 parts by weight of the photosensitive resin composition of the present invention is, for example, 0.01 parts by weight or more, 0.05 parts by weight or more, 0.1 parts by weight or more, 0.5 parts by weight or more , 1 part by weight or more, 2 parts by weight or more, 3 parts by weight or more, or 4 parts by weight or more, and may be 10 parts by weight or less, 9.5 parts by weight or less, 9 parts by weight or less, 8.5 parts by weight or less, or 8 parts by weight or less. , but not limited thereto.
본 발명의 감광성 수지 조성물에 포함되는 바인더 수지로는 아크릴 중합체 또는 측쇄에 아크릴 불포화 결합을 갖는 아크릴 중합체를 사용할 수 있다.As the binder resin included in the photosensitive resin composition of the present invention, an acrylic polymer or an acrylic polymer having an acrylic unsaturated bond in a side chain may be used.
일 구체예에서, 상기 아크릴 중합체는 아크릴계 단량체를 포함하는 단량체들의 (공)중합체일 수 있다. 이러한 아크릴계 단량체의 예로는 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 프로필(메타)아크릴레이트, 부틸(메타)아크릴레이트, 펜틸(메타)아크릴레이트, 헥실(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 헵틸(메타)아크릴레이트, 옥틸(메타)아크릴레이트, 노닐(메타)아크릴 레이트, 데실(메타)아크릴레이트, 라우릴(메타)아크릴레이트, 도데실(메타)아크릴레이트, 테트라데실(메타)아크릴레이트, 헥사데실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 아다만틸(메타)아크릴레이트, 디시클로펜타닐(메타)아크릴레이트, 디시클로펜테닐(메타)아크릴레이트, 벤질(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 2-에톡시에틸(메타)아크릴레이트, (메타)아크릴산, 이타코닉산, 말레익산, 말레익산무수물, 말레익산모노알킬에스테르, 모노알킬 이타코네이트, 모노알킬 퓨말레이트, 글리시딜 (메타)아크릴레이트, 3,4-에폭시부틸(메타)아크릴레이트, 2,3-에폭시시클로헥실(메타)아크릴레이트, 3,4-에폭시시클로헥실메틸(메타)아크릴레이트, 4-하이드록시페닐(메타)아크릴레이트, 3-메틸옥세탄-3-메틸(메타)아크릴레이트, 3-에틸옥세탄-3-메틸(메타)아크릴레이트, (메타)아크릴아미드, N-메틸(메타)아크릴아미드 등을 들 수 있으며, 이들을 각각 단독으로 또는 2종 이상 함께 사용할 수 있다. 또한 이러한 아크릴계 단량체와 스티렌, α-메틸스티렌, 아세톡시스티렌, N-메틸말레이미드, N-에틸말레이미드, N-프로필말레이미드, N-부틸말레이미드, N-시클로헥실말레이미드, N-페닐말레이미드 등의 단량체를 공중합하여 얻어진 공중합체도 본 발명에서 사용가능하다.In one embodiment, the acrylic polymer may be a (co)polymer of monomers including an acrylic monomer. Examples of such acrylic monomers include methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, butyl (meth)acrylate, pentyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, lauryl (meth)acrylate, dodecyl (meth)acrylate, Tetradecyl (meth)acrylate, hexadecyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate Late, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, (meth)acrylic acid, itaconic acid, maleic acid, maleic acid anhydride, maleic acid mono Alkyl ester, monoalkyl itaconate, monoalkyl fumarate, glycidyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, 2,3-epoxycyclohexyl (meth)acrylate, 3, 4-epoxycyclohexylmethyl (meth)acrylate, 4-hydroxyphenyl (meth)acrylate, 3-methyloxetane-3-methyl (meth)acrylate, 3-ethyloxetane-3-methyl (meth)acrylate Acrylate, (meth)acrylamide, N-methyl (meth)acrylamide, etc. can be mentioned, These can be used individually or in combination of 2 or more types. In addition, these acrylic monomers and styrene, α-methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, N-phenyl Copolymers obtained by copolymerizing monomers such as maleimide can also be used in the present invention.
일 구체예에서, 상기 측쇄에 아크릴 불포화 결합을 갖는 아크릴 중합체는 카르복실산을 함유한 아크릴 공중합체에 에폭시 수지를 부가반응한 공중합체일 수 있다. 예를 들면, 아크릴산, 메타아크릴산, 이타코닉산, 말레익산, 말레익산모노알킬 에스테르 등의 카르복실산을 함유한 아크릴 모노머와 메틸(메타)아크릴레이트, 헥실(메타)아크릴레이트 등의 알킬(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 아다만틸(메타)아크릴레이트, 디시클로펜타닐(메타)아크릴레이트, 디시클로펜테닐(메타)아크릴레이트, 벤질(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 2-에톡시에틸(메타)아크릴레이트, 스티렌, α-메틸스티렌, 아세톡시스티렌, N-메틸말레이미드, N-에틸말레이미드, N-프로필말레이미드, N-부틸말레이미드, N-시클로헥실말레이미드, (메타)아크릴아미드, N-메틸(메타)아크릴아미드 등을 공중합하여 얻은, 카르복실산을 함유한 아크릴 공중합체에 글리시딜아크릴레이트, 글리시딜메타아크릴레이트, 3,4-에폭시부틸(메타)아크릴레이트, 2,3-에폭시시클로헥실(메타)아크릴레이트, 3,4-에폭시시클로헥실메틸(메타)아크릴레이트 등의 에폭시 모노머를 40 내지 180℃의 온도에서 부가반응하여 얻어진 것을 바인더 수지로서 사용할 수 있다.In one embodiment, the acrylic polymer having an acrylic unsaturated bond in the side chain may be a copolymer obtained by adding an epoxy resin to an acrylic copolymer containing carboxylic acid. For example, acrylic monomers containing carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, maleic acid, and maleic acid monoalkyl esters, and alkyl (meth)acrylates such as methyl (meth)acrylate and hexyl (meth)acrylate )Acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, adamantyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, benzyl ( meth)acrylate, 2-methoxyethyl (meth)acrylate, 2-ethoxyethyl (meth)acrylate, styrene, α-methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, An acrylic copolymer containing carboxylic acid obtained by copolymerizing N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide, (meth)acrylamide, N-methyl (meth)acrylamide, etc. Cidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl (meth)acrylate, 2,3-epoxycyclohexyl (meth)acrylate, 3,4-epoxycyclohexylmethyl (meth)acrylate What was obtained by addition reaction of epoxy monomers, such as 40-180 degreeC, can be used as a binder resin.
측쇄에 아크릴 불포화 결합을 갖는 아크릴 중합체의 또 다른 예로는 에폭시기를 함유한 아크릴 공중합체에 카르복실산을 부가반응한 공중합체를 들 수 있다. 예를 들어, 글리시딜아크릴레이트, 글리시딜메타아크릴레이트, 3,4-에폭시부틸(메타)아크릴레이트, 2,3-에폭시시클로헥실(메타)아크릴레이트, 3,4-에폭시시클로헥실메틸(메타)아크릴레이트 등의 에폭시기를 함유한 아크릴 모노머와 메틸(메타)아크릴레이트, 헥실(메타)아크릴레이트 등의 알킬(메타)아크릴레이트, 시클로헥실(메타)아크릴레이트, 이소보닐(메타)아크릴레이트, 아다만틸(메타)아크릴 레이트, 디시클로펜타닐(메타)아크릴레이트, 디시클로펜테닐(메타)아크릴레이트, 벤질(메타)아크릴레이트, 2-메톡시에틸(메타)아크릴레이트, 2-에톡시에틸(메타) 아크릴레이트, 스티렌, α-메틸스티렌, 아세톡시스티렌, N-메틸말레이미드, N-에틸말레이미드, N-프로필말레이미드, N-부틸말레이미드, N-시클로헥실말레이미드, (메타)아크릴아미드, N-메틸(메타)아크릴아미드 등의 모노머를 공중합하여 얻은, 에폭시기를 함유한 아크릴 공중합체에 아크릴산, 메타아크릴산, 이타코닉산, 말레익산, 말레익산모노알킬에스테르 등의 카르복실산을 함유한 아크릴 모노머를 40 내지 180℃의 온도에서 부가반응하여 얻어진 것을 바인더 수지로서 사용할 수 있다.Another example of the acrylic polymer having an acrylic unsaturated bond in the side chain is a copolymer obtained by addition reaction of carboxylic acid to an acrylic copolymer containing an epoxy group. For example, glycidyl acrylate, glycidyl methacrylate, 3,4-epoxybutyl (meth)acrylate, 2,3-epoxycyclohexyl (meth)acrylate, 3,4-epoxycyclohexylmethyl Acrylic monomers containing an epoxy group such as (meth)acrylate, alkyl (meth)acrylates such as methyl (meth)acrylate and hexyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate Late, adamantyl (meth)acrylate, dicyclopentanyl (meth)acrylate, dicyclopentenyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 2- Ethoxyethyl (meth)acrylate, styrene, α-methylstyrene, acetoxystyrene, N-methylmaleimide, N-ethylmaleimide, N-propylmaleimide, N-butylmaleimide, N-cyclohexylmaleimide , acrylic acid, methacrylic acid, itaconic acid, maleic acid, maleic acid monoalkyl ester, etc. An acrylic monomer containing carboxylic acid may be used as a binder resin obtained by an addition reaction at a temperature of 40 to 180°C.
일 구체예에서, 바인더 수지로 사용되는 중합체의 중량평균 분자량(Mw, g/mol)은 2,000 내지 300,000일 수 있고, 보다 구체적으로는 4,000 내지 100,000일 수 있으며, 그 분산도는 1 내지 5일 수 있으나, 이에 한정되지 않는다.In one embodiment, the weight average molecular weight (Mw, g/mol) of the polymer used as the binder resin may be 2,000 to 300,000, more specifically 4,000 to 100,000, and the degree of dispersion may be 1 to 5. However, it is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물에 포함되는 바인더 수지의 함량은, 조성물 100 중량부를 기준으로, 40 내지 60 중량부일 수 있다. 조성물 내의 바인더 수지 함량이 상기 범위 내일 때, 패턴 특성 조절이 용이해지고, 박막의 내열성 및 내화학성 등이 양호해질 수 있다.In one embodiment, the content of the binder resin included in the photosensitive resin composition of the present invention, based on 100 parts by weight of the composition, may be 40 to 60 parts by weight. When the content of the binder resin in the composition is within the above range, pattern characteristics may be easily controlled, and heat resistance and chemical resistance of the thin film may be improved.
보다 구체적으로, 본 발명의 감광성 수지 조성물 100 중량부에 포함되는 바인더 수지의 함량은, 예컨대, 40 중량부 이상, 41 중량부 이상, 42 중량부 이상, 43 중량부 이상, 44 중량부 이상 또는 45 중량부 이상일 수 있고, 또한 60 중량부 이하, 59 중량부 이하, 58 중량부 이하, 57 중량부 이하, 56 중량부 이하 또는 55 중량부 이하일 수 있으나, 이에 한정되지 않는다.More specifically, the content of the binder resin included in 100 parts by weight of the photosensitive resin composition of the present invention is, for example, 40 parts by weight or more, 41 parts by weight or more, 42 parts by weight or more, 43 parts by weight or more, 44 parts by weight or more, or 45 parts by weight or more. It may be more than 60 parts by weight, 59 parts by weight or less, 58 parts by weight or less, 57 parts by weight or less, 56 parts by weight or less, or 55 parts by weight or less, but is not limited thereto.
본 발명의 감광성 수지 조성물에 포함되는 광중합성 화합물로는 2개 이상의 에틸렌계 이중 결합을 가지는 가교성 모노머를 사용할 수 있다.As the photopolymerizable compound included in the photosensitive resin composition of the present invention, a crosslinkable monomer having two or more ethylenic double bonds may be used.
일 구체예에서, 이러한 가교성 모노머의 예로는, 에틸렌옥사이드기의 수가 2 내지 20인 폴리에틸렌글리콜디(메타)아크릴레이트, 에틸렌글리콜디(메타)아크릴레이트, 프로필렌옥사이드기의 수가 2 내지 14인 폴리프로필렌글리콜디(메타)아크릴레이트, 프로필렌글리콜디(메타)아크릴레이트, 트리메틸올프로판디(메타)아크릴레이트, 비스페놀 A와 디글리시딜에테르아크릴산의 부가반응 생성물, 에틸이소시아눌릭산트리(메타)아크릴레이트, β-히드록시에틸(메타)아크릴레이트의 프탈산디에스테르, β-히드록시에틸(메타)아크릴레이트와 톨루엔 디이소시아네이트의 부가반응 생성물, 트리메틸올프로판트리(메타)아크릴레이트, 테트라메틸올메탄테트라(메타)아크릴레이트, 펜타에리스리톨트리(메타)아크릴레이트, 펜타에리스리톨테트라(메타)아크릴레이트, 디펜타에리스리톨펜타(메타)아크릴레이트, 디펜타에리스리톨헥사(메타)아크릴레이트, 디펜타에리스리톨트리(메타)아크릴레이트, 트리메틸올과 프로판트리글리시딜에테르아크릴산의 부가반응 생성물 및 노볼락 에폭시 수지와 (메타)아크릴산의 부가반응 생성물에 프탈산 무수물을 반응하여 생성된 노볼락 에폭시 아크릴레이트 등이 있다. 이들은 단독으로 혹은 2종 이상 조합하여 사용될 수 있다.In one embodiment, examples of such crosslinkable monomers include polyethylene glycol di(meth)acrylate having 2 to 20 ethylene oxide groups, ethylene glycol di(meth)acrylate, and poly(meth)acrylate having 2 to 14 propylene oxide groups. Propylene glycol di(meth)acrylate, propylene glycol di(meth)acrylate, trimethylolpropane di(meth)acrylate, addition reaction product of bisphenol A and diglycidyl ether acrylic acid, ethyl isocyanuric acid tri(meth) )Acrylate, phthalic acid diester of β-hydroxyethyl (meth)acrylate, addition reaction product of β-hydroxyethyl (meth)acrylate and toluene diisocyanate, trimethylolpropane tri(meth)acrylate, tetramethyl Olmethane tetra(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol penta(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol Tri(meth)acrylate, novolak epoxy acrylate produced by reacting phthalic anhydride with an addition reaction product of trimethylol and propane triglycidyl ether acrylic acid, and an addition reaction product of novolak epoxy resin and (meth)acrylic acid. . These may be used alone or in combination of two or more.
일 구체예에 따르면, 상기 광중합성 화합물로서 이소시아누레이트 화합물을 사용할 수 있으며, 이러한 이소시아누레이트 화합물로는 모노알릴디글리시딜이소시아누레이트 화합물, 디알릴모노글리시딜이소시아누레이트 화합물, 트리알릴이소시아누레이트 화합물 등을 들 수 있다. 상기 모노알릴디글리시딜이소시아누레이트 화합물의 예로는 모노알릴디글리시딜이소시아누레이트, 1-알릴-3,5-비스(2-메틸에폭시프로필)이소시아누레이트, 1-(2-메틸프로페닐)-3,5-디글리시딜이소시아누레이트, 1-(2-메틸프로페닐)-3,5-비스(2-메틸에폭시프로필)이소시아누레이트 등이 있고, 상기 디알릴모노글리시딜이소시아누레이트 화합물의 예로는 디알릴모노글리시딜이소시아누레이트, 1,3-디알릴-5-(2-메틸에폭시프로필)이소시아누레이트, 1,3-비스(2-메틸프로페닐)-5-글리시딜이소시아누레이트, 1,3-비스(2-메틸프로페닐)-5-(2-메틸에폭시프로필)이소시아누레이트 등이 있으며, 상기 트리알릴이소시아누레이트 화합물의 예로는 트리알릴이소시아누레이트, 트리스(2-메틸프로페닐)이소시아누레이트 등이 있으나, 이에 한정되지 않는다. 이들은 단독으로 혹은 2종 이상 조합하여 사용될 수 있다.According to one embodiment, an isocyanurate compound may be used as the photopolymerizable compound, and examples of the isocyanurate compound include a monoallyldiglycidylisocyanurate compound and a diallylmonoglycidylisocyanurate compound. A rate compound, a triallyl isocyanurate compound, etc. are mentioned. Examples of the monoallyldiglycidylisocyanurate compound include monoallyldiglycidylisocyanurate, 1-allyl-3,5-bis(2-methylepoxypropyl)isocyanurate, 1-( 2-methylpropenyl)-3,5-diglycidyl isocyanurate, 1-(2-methylpropenyl)-3,5-bis(2-methylepoxypropyl)isocyanurate, and the like; Examples of the diallyl monoglycidyl isocyanurate compound include diallyl monoglycidyl isocyanurate, 1,3-diallyl-5-(2-methylepoxypropyl) isocyanurate, 1,3 -Bis(2-methylpropenyl)-5-glycidyl isocyanurate, 1,3-bis(2-methylpropenyl)-5-(2-methylepoxypropyl)isocyanurate, etc. Examples of the triallyl isocyanurate compound include triallyl isocyanurate, tris (2-methylpropenyl) isocyanurate, and the like, but are not limited thereto. These may be used alone or in combination of two or more.
일 구체예에서, 본 발명의 감광성 수지 조성물에 포함되는 광중합성 화합물의 함량은, 조성물 100 중량부를 기준으로, 5 내지 20 중량부일 수 있다. 조성물 내의 광중합성 화합물 함량이 상기 범위 내일 때, 노광 및 현상 공정 진행 후에 노광된 부분의 패턴 모양이 우수하게 유지될 수 있다.In one embodiment, the amount of the photopolymerizable compound included in the photosensitive resin composition of the present invention may be 5 to 20 parts by weight based on 100 parts by weight of the composition. When the content of the photopolymerizable compound in the composition is within the above range, the pattern shape of the exposed portion may be excellently maintained after exposure and development processes are performed.
보다 구체적으로, 본 발명의 감광성 수지 조성물 100 중량부에 포함되는 광중합성 화합물의 함량은, 예컨대, 5 중량부 이상, 6 중량부 이상, 7 중량부 이상 또는 8 중량부 이상일 수 있고, 또한 20 중량부 이하, 19 중량부 이하, 18 중량부 이하, 17 중량부 이하, 16 중량부 이하 또는 15 중량부 이하일 수 있으나, 이에 한정되지 않는다.More specifically, the amount of the photopolymerizable compound included in 100 parts by weight of the photosensitive resin composition of the present invention may be, for example, 5 parts by weight or more, 6 parts by weight or more, 7 parts by weight or more, or 8 parts by weight or more, or 20 parts by weight or more. parts by weight or less, 19 parts by weight or less, 18 parts by weight or less, 17 parts by weight or less, 16 parts by weight or less, or 15 parts by weight or less, but is not limited thereto.
본 발명의 감광성 수지 조성물은, 상기 설명한 성분들 이외에, 감광성 수지 조성물에 통상 사용되는 성분들을 하나 이상 더 포함할 수 있다.The photosensitive resin composition of the present invention may further include one or more components commonly used in photosensitive resin compositions in addition to the components described above.
일 구체예에서, 본 발명의 감광성 수지 조성물은 상기 화학식 1로 표시되는 옥심에스테르 플루오렌 유도체 화합물들 이외에 추가의 광개시제를 더 포함할 수 있다.In one embodiment, the photosensitive resin composition of the present invention may further include an additional photoinitiator in addition to the oxime ester fluorene derivative compounds represented by Chemical Formula 1.
이러한 추가의 광개시제로는, 아세토페논계, 벤조페논계, 트리아진계, 벤조인계, 이미다졸계, 잔톤계 및/또는 옥심계 광 개시제(예컨대, OXE-01, OXE-02, N-1919, Irgacure 651, Irgacure 907, Irgacure 369, Irgacure 379, TPO, CGI124, EPD/BMS 혼합계 등)를 사용할 수 있으며, 보다 구체적으로 상기 추가의 광개시제는, 벤조페논, 페닐비페닐케톤, 1-히드록시-1-벤조일사이클로헥산, 벤질디메틸케탈, 1-벤질-1-디메틸아미노-1-(4-모폴리노-벤조일)프로판, 2-모폴릴-2-(4-메틸머캅토)벤조일프로판, 티오잔톤(thioxanthone), 1-클로로-4-프록시티오잔톤(1-chloro-4-proxythioxanthone), 이소프로필티오잔톤, 디에틸티오잔톤, 에틸안트라퀴논, 4-벤조일-4-메틸디페닐설파이드, 벤조일부틸에테르, 2-히드록시-2-벤조일프로판, 2-히드록시-2-(4-이소프로필)벤조일프로판, 4-부틸벤조일트리클로로메탄, 4-페녹시벤조일디클로로메탄, 벤조일포름산메틸, 1,7-비스(9-아크리디닐)헵탄, 9-n-부틸-3,6-비스(2-모폴리노-이소부틸로일)카바졸, 2-메틸-4,6-비스(트리클로로메틸)-s-트리아진, 2-페닐-4,6-비스(트리클로로메틸)-s-트리아진, 2-나프틸-4,6-비스(트리클로로메틸)-s-트리아진 또는 이들의 혼합물일 수 있으나, 이에 한정되지 않는다.Such additional photoinitiators include acetophenone-based, benzophenone-based, triazine-based, benzoin-based, imidazole-based, xanthone-based and/or oxime-based photoinitiators (e.g., OXE-01, OXE-02, N-1919, Irgacure 651, Irgacure 907, Irgacure 369, Irgacure 379, TPO, CGI124, EPD/BMS mixed system, etc.) may be used, and more specifically, the additional photoinitiators include benzophenone, phenylbiphenylketone, 1-hydroxy-1 -Benzylcyclohexane, benzyldimethylketal, 1-benzyl-1-dimethylamino-1-(4-morpholino-benzoyl)propane, 2-morpholyl-2-(4-methylmercapto)benzoylpropane, thioxanthone (thioxanthone), 1-chloro-4-proxythioxanthone, isopropylthioxanthone, diethylthioxanthone, ethylanthraquinone, 4-benzoyl-4-methyldiphenylsulfide, benzoylbutyl Ether, 2-hydroxy-2-benzoylpropane, 2-hydroxy-2-(4-isopropyl)benzoylpropane, 4-butylbenzoyltrichloromethane, 4-phenoxybenzoyldichloromethane, benzoylformate, 1, 7-bis (9-acridinyl) heptane, 9-n-butyl-3,6-bis (2-morpholino-isobutyloyl) carbazole, 2-methyl-4,6-bis (trichloro Methyl) -s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2-naphthyl-4,6-bis (trichloromethyl) -s-triazine or these It may be a mixture of, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물이 이러한 추가의 광개시제를 포함하는 경우, 그 함량은, 조성물 100 중량부를 기준으로, 예컨대, 0.01 내지 10 중량부일 수 있고, 보다 구체적으로는 0.01 내지 5 중량부일 수 있으나, 이에 한정되지 않는다.In one embodiment, when the photosensitive resin composition of the present invention includes such an additional photoinitiator, the content thereof may be, for example, 0.01 to 10 parts by weight, more specifically 0.01 to 5 parts by weight, based on 100 parts by weight of the composition. It may be negative, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물은 광개시제의 라디칼 생성 및 박막의 경화도를 증진시키기 위하여 보조경화제를 더 포함할 수 있다.In one embodiment, the photosensitive resin composition of the present invention may further include an auxiliary curing agent in order to increase the radical generation of the photoinitiator and the curing degree of the thin film.
이러한 보조경화제는, 예컨대, 디옥틸프탈레이트, 디이소노닐프탈레이트, 디옥틸아디페이트, 트리크레실포스페이트, 및 2,2,4-트리메틸-1,3-펜탄디올 모노이소부티레이트, 2-머캡토벤조이미다졸, 2-머캡토벤조티아졸, 2-머캡토벤조옥사졸, 2,5,-디머캡토-1,3,4-티아디아졸, 및 2-머캡토-4,6-디메틸아미노피리딘으로 이루어진 그룹으로 선택된 하나 이상일 수 있으나, 이에 한정되지 않는다.Such co-curing agents include, for example, dioctylphthalate, diisononylphthalate, dioctyl adipate, tricresyl phosphate, and 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, 2-mercaptobenzo Imidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5,-dimercapto-1,3,4-thiadiazole, and 2-mercapto-4,6-dimethylaminopyridine It may be one or more selected from a group consisting of, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물이 이러한 보조경화제를 포함하는 경우, 그 함량은, 조성물 100 중량부를 기준으로, 예컨대, 0.1 내지 10 중량부일 수 있으나, 이에 한정되지 않는다.In one embodiment, when the photosensitive resin composition of the present invention includes such an auxiliary curing agent, the content thereof may be, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the composition, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물은 기판과의 접착성을 향상시키기 위하여 접착 보조제를 더 포함할 수 있다.In one embodiment, the photosensitive resin composition of the present invention may further include an adhesive aid to improve adhesion with a substrate.
이러한 접착 보조제는 비닐기, 카르복실기, 메타크릴옥시기, 이소시아네이트기, 에폭시기 등의 반응성 치환기를 가질 수 있으며, 예컨대, 트리메톡시실릴 벤조산, γ-메타크릴옥시프로필 트리메톡시실란, 비닐 트리아세톡시실란, 비닐 트리메톡시실란, γ-이소시아네이트 프로필 트리에톡시실란, γ-글리시독시프로필트리메톡시실란, 및 β-(3,4-에폭시사이클로헥실)에틸트리메톡시실란으로 이루어진 그룹으로 선택된 하나 이상일 수 있으나, 이에 한정되지 않는다.The adhesive aid may have a reactive substituent such as a vinyl group, a carboxyl group, a methacryloxy group, an isocyanate group, an epoxy group, and the like, and examples thereof include trimethoxysilyl benzoic acid, γ-methacryloxypropyl trimethoxysilane, and vinyl triacetoxy. selected from the group consisting of silane, vinyl trimethoxysilane, γ-isocyanate propyl triethoxysilane, γ-glycidoxypropyltrimethoxysilane, and β-(3,4-epoxycyclohexyl)ethyltrimethoxysilane It may be one or more, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물이 이러한 접착 보조제를 포함하는 경우, 그 함량은, 조성물 100 중량부를 기준으로, 예컨대, 0.1 내지 10 중량부일 수 있으나, 이에 한정되지 않는다.In one embodiment, when the photosensitive resin composition of the present invention includes such an adhesive aid, the content thereof may be, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the composition, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물은 코팅성이나 현상성을 향상시키기 위하여 계면활성제를 더 포함할 수 있다.In one embodiment, the photosensitive resin composition of the present invention may further include a surfactant to improve coating properties or developability.
이러한 계면활성제는, 예컨대, 불소계 계면활성제 또는 실리콘 계면활성제일 수 있으나, 이에 한정되지 않는다. 불소계 계면활성제의 시판품으로는 BM-1000, BM-1100(BM Chemie社), 프로라이드 FC-135/FC-170C/FC-430(스미토모 쓰리엠㈜), SH-28PA/-190/SZ-6032(도레 시리콘㈜) 등이 있고, 실리콘 계면활성제의 시판품으로는 BYK사의 BYK-310,BYK-313, BYK-320, BYK-333 등이 있으며, 분산성의 면에서 유리하게는 BYK-307이 사용될 수 있다.Such surfactants may be, for example, fluorine-based surfactants or silicone surfactants, but are not limited thereto. Commercially available fluorinated surfactants include BM-1000, BM-1100 (BM Chemie Co.), Proride FC-135/FC-170C/FC-430 (Sumitomo 3M Co., Ltd.), SH-28PA/-190/SZ-6032 ( Dore Silicon Co., Ltd.), and commercially available silicone surfactants include BYK's BYK-310, BYK-313, BYK-320, and BYK-333, and BYK-307 can be used advantageously in terms of dispersibility. there is.
일 구체예에서, 본 발명의 감광성 수지 조성물이 이러한 계면활성제를 포함하는 경우, 그 함량은, 조성물 100 중량부를 기준으로, 예컨대, 0.01 내지 5 중량부일 수 있으나, 이에 한정되지 않는다.In one embodiment, when the photosensitive resin composition of the present invention includes such a surfactant, the content thereof may be, for example, 0.01 to 5 parts by weight based on 100 parts by weight of the composition, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물은 용매를 더 포함할 수 있다.In one embodiment, the photosensitive resin composition of the present invention may further include a solvent.
용매로는 바인더 수지, 다관능 모노머, 및 기타 첨가제와의 상용성을 고려하여 적절한 것을 사용할 수 있으며, 예컨대, 메탄올, 에탄올 등의 알코올류; 디클로로에틸 에테르, n-부틸 에테르, 디이소아밀 에테르, 메틸페닐 에테르, 테트라히드로퓨란 등의 에테르류; 에틸렌 글리콜 모노메틸에테르, 에틸렌 글리콜 모노에틸에테르 등의 글리콜 에테르류; 메틸 셀로솔브 아세테이트, 에틸 셀로솔브 아세테이트, 디에틸 셀로솔브 아세테이트 등의 셀로솔브 아세테이트류; 메틸에틸 카르비톨, 디에틸 카르비톨, 디에틸렌 글리콜 모노메틸에테르, 디에틸렌 글리콜 모노에틸에테르, 디에틸렌 글리콜 디메틸에테르, 디에틸렌 글리콜 메틸에틸에테르, 디에틸렌 글리콜 디에틸에테르 등의 카르비톨류; 프로필렌 글리콜 메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류; 톨루엔, 크실렌 등의 방향족 탄화수소류; 메틸에틸케톤, 사이클로헥사논, 4-히드록시-4-메틸-2-펜타논, 메틸-n-프로필케톤, 메틸-n-부틸케톤, 메틸-n-아밀케톤, 2-헵타논 등의 케톤류; 초산 에틸, 초산-n-부틸, 초산 이소부틸 등의 포화 지방족 모노카르복실산 알킬 에스테르류; 젖산 메틸, 젖산 에틸 등의 젖산 에스테르류; 옥시 초산 메틸, 옥시 초산 에틸, 옥시 초산 부틸 등의 옥시 초산 알킬 에스테르류; 메톡시 초산 메틸, 메톡시 초산 에틸, 메톡시 초산 부틸, 에톡시 초산 메틸, 에톡시 초산 에틸 등의 알콕시 초산 알킬 에스테르류; 3-옥시 프로피온산 메틸, 3-옥시 프로피온산 에틸 등의 3-옥시 프로피온산 알킬 에스테르류; 3-메톡시 프로피온산 메틸, 3-메톡시 프로피온산 에틸, 3-에톡시 프로피온산 에틸, 3-에톡시 프로피온산 메틸 등의 3-알콕시 프로피온산 알킬 에스테르류; 2-옥시 프로피온산 메틸, 2-옥시 프로피온산 에틸, 2-옥시 프로피온산 프로필 등의 2-옥시 프로피온산 알킬 에스테르류; 2-메톡시 프로피온산메틸, 2-메톡시 프로피온산 에틸, 2-에톡시 프로피온산 에틸, 2-에톡시 프로피온산 메틸 등의 2-알콕시 프로피온산 알킬 에스테르류; 2-옥시-2-메틸 프로피온산 메틸, 2-옥시-2-메틸 프로피온산 에틸 등의 2-옥시-2-메틸프로피온산 에스테르류, 2-메톡시-2-메틸 프로피온산 메틸, 2-에톡시-2-메틸 프로피온산 에틸 등의 2-알콕시-2-메틸 프로피온산 알킬류의 모노옥시 모노카르복실산 알킬 에스테르류; 2-히드록시 프로피온산 에틸, 2-히드록시-2-메틸 프로피온산 에틸, 히드록시 초산 에틸, 2-히드록시-3-메틸 부탄산 메틸 등의 에스테르류; 피루빈산 에틸 등의 케톤산 에스테르류 등이 있으며, 또한, N-메틸포름아미드, N,N-디메틸포름아미드, N-메틸포름아닐리드, N-메틸아세트아미드, N,N-디메틸아세트아미드, N-메틸피롤리돈, 디메틸술폭시드, 벤질에틸에테르, 디헥실에테르, 아세틸아세톤, 이소포론, 카프론산, 카프릴산, 1-옥탄올, 1-노난올, 벤질알코올, 초산 벤질, 안식향산 에틸, 옥살산 디에틸, 말레인산 디에틸, γ-부티로락톤, 탄산 에틸렌, 탄산 프로필렌, 페닐 셀로솔브 아세테이트 중에서 선택된 용매를 단독으로 또는 2종 이상을 혼합한 용매를 사용할 수 있으나, 이에 한정되지 않는다.As the solvent, an appropriate solvent may be used in consideration of compatibility with the binder resin, the multifunctional monomer, and other additives, and examples thereof include alcohols such as methanol and ethanol; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, and tetrahydrofuran; glycol ethers such as ethylene glycol monomethyl ether and ethylene glycol monoethyl ether; Cellosolve acetates, such as methyl cellosolve acetate, ethyl cellosolve acetate, and diethyl cellosolve acetate; carbitols such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and diethylene glycol diethyl ether; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate and propylene glycol propyl ether acetate; Aromatic hydrocarbons, such as toluene and xylene; Ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-propyl ketone, methyl-n-butyl ketone, methyl-n-amyl ketone, and 2-heptanone ; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate and isobutyl acetate; lactic acid esters such as methyl lactate and ethyl lactate; oxyacetic acid alkyl esters such as methyl oxyacetate, ethyl oxyacetate, and butyl oxyacetate; Alkoxy acetic acid alkyl esters, such as methoxy methyl acetate, methoxy ethyl acetate, methoxy butyl acetate, ethoxy methyl acetate, and ethoxy ethyl acetate; 3-oxy propionic acid alkyl esters such as 3-oxy methyl propionate and 3-oxy ethyl propionate; 3-alkoxy propionic acid alkyl esters such as 3-methoxy methyl propionate, 3-methoxy ethyl propionate, 3-ethoxy ethyl propionate, and 3-ethoxy methyl propionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, and propyl 2-oxypropionate; 2-alkoxy propionic acid alkyl esters such as 2-methoxy methyl propionate, 2-methoxy ethyl propionate, 2-ethoxy ethyl propionate, and 2-ethoxy methyl propionate; 2-oxy-2-methylpropionic acid esters such as 2-oxy-2-methyl methyl propionate, 2-oxy-2-methyl ethyl propionate, 2-methoxy-2-methyl methyl propionate, 2-ethoxy-2- monooxy monocarboxylic acid alkyl esters of 2-alkoxy-2-methyl alkyl propionate such as methyl ethyl propionate; esters such as 2-hydroxy ethyl propionate, 2-hydroxy-2-methyl ethyl propionate, hydroxy ethyl acetate, and 2-hydroxy-3-methyl methyl butanoate; and ketonic acid esters such as ethyl pyruvate, N-methylformamide, N,N-dimethylformamide, N-methylformanilide, N-methylacetamide, N,N-dimethylacetamide, N-methylpyrrolidone, dimethylsulfoxide, benzylethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate , Diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, and a solvent selected from phenyl cellosolve acetate alone or a mixture of two or more solvents may be used, but is not limited thereto.
일 구체예에서, 본 발명의 감광성 수지 조성물 내의 용매 함량은 조성물 총 중량에서 나머지 성분들의 함량을 제외한 잔량으로, 조성물 100 중량부를 기준으로, 예컨대, 20 내지 80 중량부일 수 있고, 보다 구체적으로는 30 내지 60 중량부일 수 있으나, 이에 한정되지 않는다.In one embodiment, the content of the solvent in the photosensitive resin composition of the present invention is the remaining amount after subtracting the content of the remaining components from the total weight of the composition, based on 100 parts by weight of the composition, may be, for example, 20 to 80 parts by weight, more specifically 30 parts by weight to 60 parts by weight, but is not limited thereto.
본 발명의 감광성 수지 조성물은 포토레지스트 공정에서 사용되는 알칼리 현상 용액인 2.38% TMAH 용액에 뛰어난 현상력을 나타내고, 친환경적인 알카리 수용액에도 쉽게 제거되므로 남이 있는 포토레지스트 및 제거되는 포토레지스트로 사용되기에도 매우 적합하다.The photosensitive resin composition of the present invention exhibits excellent developing power in 2.38% TMAH solution, which is an alkaline developing solution used in the photoresist process, and is easily removed even in an environmentally friendly alkaline aqueous solution, so it is very suitable for use as a photoresist with residue and a photoresist to be removed. Suitable.
따라서, 본 발명의 다른 측면에 따르면, 상기 감광성 수지 조성물로부터 형성된 경화막이 제공된다.Therefore, according to another aspect of the present invention, a cured film formed from the photosensitive resin composition is provided.
본 발명의 또 다른 측면에 따르면, 상기 경화막을 포함하는 전자 소자(예컨대, LED, TFT-LCD, MEMS, 반도체 소자 등)가 제공된다.According to another aspect of the present invention, an electronic device (eg, LED, TFT-LCD, MEMS, semiconductor device, etc.) including the cured film is provided.
이하, 실시예 및 비교예를 통하여 본 발명을 보다 상세하게 설명한다. 그러나, 본 발명의 범위가 이들로 한정되는 것은 아니다.Hereinafter, the present invention will be described in more detail through Examples and Comparative Examples. However, the scope of the present invention is not limited thereto.
[실시예][Example]
제조예: 바인더 수지의 제조Production Example: Production of Binder Resin
모노머들로서, 메틸아크릴산(MAA), 스티렌(STY), 글리시딜 메타크릴레이트(GMA), 메틸메타크릴레이트(MMA) 및 4-히드록시페닐 말레이미드(HPMI)를 각각 10:35:10:35:10의 몰비로 혼합한 혼합물 40 중량부를 3구 둥근 바닥 플라스크에 첨가한 다음, 열개시제 1.5 중량부, 사슬이동제로 2.5 중량부를 첨가하였다. 중합 용매로 메틸 3-메톡시프로피오네이트(MMP) 60 중량부를 반응 플라스크에 첨가하여 모노머, 개시제, 사슬이동제들을 용해한 후 70℃를 유지하면서 약 6시간 동안 교반하에 중합하였다. 그 후, 중합금지제 t-부틸하이드로퀴논(t-BHQ) 100 ppm을 넣어 추가적인 중합을 금지시켰다. 제조된 공중합체의 중량평균분자량(Mw)은 9,230 분산도 (PDI)는 2.10 이었다As monomers, methyl acrylic acid (MAA), styrene (STY), glycidyl methacrylate (GMA), methyl methacrylate (MMA) and 4-hydroxyphenyl maleimide (HPMI) were prepared in 10:35:10: 40 parts by weight of the mixture mixed in a molar ratio of 35:10 was added to a three-neck round bottom flask, followed by addition of 1.5 parts by weight of a thermal initiator and 2.5 parts by weight of a chain transfer agent. 60 parts by weight of methyl 3-methoxypropionate (MMP) as a polymerization solvent was added to the reaction flask to dissolve the monomer, initiator, and chain transfer agent, and then polymerization was performed under stirring for about 6 hours while maintaining 70°C. Thereafter, 100 ppm of polymerization inhibitor t-butylhydroquinone (t-BHQ) was added to inhibit further polymerization. The weight average molecular weight (Mw) of the prepared copolymer was 9,230 and the degree of dispersion (PDI) was 2.10.
감광성 수지 조성물 제조Preparation of photosensitive resin composition
하기 by 1에 나타낸 종류 및 양의 성분들을 사용하여 감광성 수지 조성물을 제조하였다. A photosensitive resin composition was prepared using the types and amounts of components shown in by 1 below.
- 바인더 공중합체: 상기 제조예에서 제조된 공중합체- Binder copolymer: copolymer prepared in the above preparation example
- 다관능 모노머(광중합성 화합물): 트리메틸올프로판 트리아크릴레이트- Multifunctional monomer (photopolymerizable compound): trimethylolpropane triacrylate
- 광개시제 A: 하기 화학식의 옥심에스테르 플루오렌 유도체-Photoinitiator A: oxime ester fluorene derivative of the following formula
- 광개시제 B: 하기 화학식의 옥심에스테르 플루오렌 유도체- Photoinitiator B: oxime ester fluorene derivative of the following formula
- TPO: 2,4,6,-트리메틸벤조일디페닐포스핀 옥사이드- TPO: 2,4,6,-trimethylbenzoyldiphenylphosphine oxide
- 계면활성제: byk-307(BYK사)-Surfactant: byk-307 (BYK)
- 용매: 프로필렌 글리콜 메틸 에테르 아세테이트- Solvent: Propylene glycol methyl ether acetate
[표 1][Table 1]
박막 제조 및 박막 성능 평가Thin film fabrication and thin film performance evaluation
제조된 각 실시예 및 비교예의 감광성 수지 조성물을 각각 Cu 웨이퍼 위에 스핀코팅 방법으로 약 100 마이크로미터 두께를 코팅하였다. 이후 코팅막을 100℃ 핫플레이트 위에서 약 10분간 프리베이크하여 코팅막에 잔류하는 용매를 제거하였다. 이후 박막의 두께를 확인하기 위하여 Dektak 장비를 사용하여 두께를 측정하였다.The prepared photosensitive resin composition of each Example and Comparative Example was coated on a Cu wafer to a thickness of about 100 micrometers by a spin coating method. Thereafter, the coating film was prebaked on a hot plate at 100° C. for about 10 minutes to remove the solvent remaining in the coating film. Then, the thickness was measured using Dektak equipment to check the thickness of the thin film.
기판 상의 코팅막을 Sapphire100E(Ultratech)를 이용하여 i-line 기준 100~2000mJ로 빛을 조사한 후 2.38% TMAH 알칼리 용액에 약 60초간 노출시켜 현상을 하였다. 이후 형성된 패턴의 모양을 확인하기 위하여 SEM 장비를 이용하여 측정하였다. 패턴의 모양이 직진성이 좋을 경우 “양호”, 박막 하부의 경화도 부족으로 인하여 패턴이 역삼각형을 나타내는 경우에는 “역사다리꼴”, 그리고 경화도가 많이 부족하여 패턴이 없거나, 노광기에서 나온 빛이 박막의 하부에까지 도달하지 못하여 현상 후 패턴이 떨어지는 경우 “X”로 표기하였다. The coating film on the substrate was irradiated with light at 100 to 2000 mJ based on i-line using Sapphire100E (Ultratech), and then exposed to a 2.38% TMAH alkaline solution for about 60 seconds to develop. Then, in order to confirm the shape of the formed pattern, it was measured using SEM equipment. “Good” when the shape of the pattern is good in straightness, “Inverted trapezoid” when the pattern shows an inverted triangle due to insufficient curing of the lower part of the thin film, and “Inverted trapezoid” when the curing degree is too insufficient and there is no pattern, or the light from the exposure machine If the pattern did not reach the bottom and the pattern fell after development, it was marked as “X”.
한편, 기판 상의 접착력을 확인하기 위해서 현미경으로 확인하였으며 패턴의 접착성을 확인하였다. 50㎛ 패턴이 남아 있는 기준으로 광량을 정리하여 표기하였다.On the other hand, in order to confirm the adhesive force on the substrate, it was confirmed with a microscope and the adhesiveness of the pattern was confirmed. The amount of light was summarized and marked based on the remaining 50 μm pattern.
[표 2][Table 2]
상기 표 2로부터 알 수 있듯이, 본 발명 실시예의 조성물들은 기존에 사용하는 광개시제 대비 적은 양을 사용하면서도 낮은 광량에서 패턴을 형성할 뿐만 아니라 패턴의 모양 및 접착력이 우수하였다. As can be seen from Table 2, the compositions of Examples of the present invention not only formed a pattern at a low amount of light while using a smaller amount than the conventional photoinitiator, but also had excellent shape and adhesive strength of the pattern.
반면, 비교예 1은 700mJ의 광량에서 광량이 부족하여 패턴이 떨어졌고, 비교예 2는 광량이 부족하여 패턴은 형성하였지만 역사다리꼴의 형태를 띠었으며, 비교예 3의 경우에는 광량은 충분하였지만 박막의 하부까지 빛이 도달하지 못하여 패턴이 떨어졌고, 비교예 4, 5는 광량이 부족하여 패턴이 떨어졌으며, 비교예 6은 패턴이 붙어 있지만 역사다리꼴의 형태를 띠었고, 비교예 7, 8 및 9는 광량이 부족하여 패턴이 다 떨어졌다.On the other hand, in Comparative Example 1, the pattern fell due to the insufficient amount of light at the light amount of 700mJ, and in Comparative Example 2, the pattern was formed due to the insufficient amount of light, but took the form of an inverted trapezoid. In the case of Comparative Example 3, the amount of light was sufficient, but the thin film The pattern fell because the light did not reach the lower part, and in Comparative Examples 4 and 5, the pattern fell because the amount of light was insufficient, and in Comparative Example 6, although the pattern was attached, it took the form of an inverted trapezoid. 9 ran out of patterns due to lack of light.
Claims (7)
[화학식 1]
상기 화학식 1에서,
R1 내지 R3는 각각 독립적으로 수소, 할로겐, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬 또는 (C3-C20)사이클로알킬이고;
A는 수소, (C1-C20)알킬, (C6-C20)아릴, (C1-C20)알콕시, (C6-C20)아릴(C1-C20)알킬, 히드록시(C1-C20)알킬, 히드록시(C1-C20)알콕시(C1-C20)알킬, (C3-C20)사이클로알킬, 아미노, 니트로, 시아노 또는 히드록시이고;
n은 0 또는 1이다.Two or more oxime ester fluorene derivative compounds represented by the following formula (1) as photoinitiator components; bookbinder; And a photopolymerizable compound; a photosensitive resin composition comprising:
[Formula 1]
In Formula 1,
R 1 to R 3 are each independently selected from hydrogen, halogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy( C1-C20)alkyl, hydroxy(C1-C20)alkoxy(C1-C20)alkyl or (C3-C20)cycloalkyl;
A is hydrogen, (C1-C20)alkyl, (C6-C20)aryl, (C1-C20)alkoxy, (C6-C20)aryl(C1-C20)alkyl, hydroxy (C1-C20)alkyl, hydroxy( C1-C20)alkoxy(C1-C20)alkyl, (C3-C20)cycloalkyl, amino, nitro, cyano or hydroxy;
n is 0 or 1;
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