KR101814673B1 - Novel compound,photosensitive resin composition comprising the same and color filter - Google Patents
Novel compound,photosensitive resin composition comprising the same and color filter Download PDFInfo
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- KR101814673B1 KR101814673B1 KR1020140169129A KR20140169129A KR101814673B1 KR 101814673 B1 KR101814673 B1 KR 101814673B1 KR 1020140169129 A KR1020140169129 A KR 1020140169129A KR 20140169129 A KR20140169129 A KR 20140169129A KR 101814673 B1 KR101814673 B1 KR 101814673B1
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 146
- 239000011342 resin composition Substances 0.000 title claims abstract description 62
- 239000000126 substance Substances 0.000 claims abstract description 78
- 239000000049 pigment Substances 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 18
- 239000011347 resin Substances 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000003999 initiator Substances 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 239000001043 yellow dye Substances 0.000 claims description 6
- 229910052796 boron Inorganic materials 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229910052698 phosphorus Inorganic materials 0.000 claims description 4
- 230000031700 light absorption Effects 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 5
- 125000000962 organic group Chemical group 0.000 claims 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- 230000015572 biosynthetic process Effects 0.000 description 47
- 238000003786 synthesis reaction Methods 0.000 description 46
- -1 aromatic vinyl compound Chemical class 0.000 description 30
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 28
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 27
- 238000006243 chemical reaction Methods 0.000 description 26
- 238000004440 column chromatography Methods 0.000 description 26
- 239000011541 reaction mixture Substances 0.000 description 20
- 239000003446 ligand Substances 0.000 description 19
- 239000002243 precursor Substances 0.000 description 19
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 18
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 18
- 229910052802 copper Inorganic materials 0.000 description 18
- 239000010949 copper Substances 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
- 238000000605 extraction Methods 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 150000001639 boron compounds Chemical class 0.000 description 12
- 239000006185 dispersion Substances 0.000 description 12
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 11
- 239000000975 dye Substances 0.000 description 11
- 239000004593 Epoxy Substances 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- UKVQBONVSSLJBB-UHFFFAOYSA-N 2-pyridin-2-ylacetonitrile Chemical compound N#CCC1=CC=CC=N1 UKVQBONVSSLJBB-UHFFFAOYSA-N 0.000 description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 9
- 230000002378 acidificating effect Effects 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000012312 sodium hydride Substances 0.000 description 9
- 229910000104 sodium hydride Inorganic materials 0.000 description 9
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000002270 dispersing agent Substances 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- 238000004519 manufacturing process Methods 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 125000005907 alkyl ester group Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 239000000178 monomer Substances 0.000 description 7
- 229910000027 potassium carbonate Inorganic materials 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 229920001577 copolymer Polymers 0.000 description 6
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 5
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 5
- 239000003086 colorant Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- YKHQFTANTNMYPP-UHFFFAOYSA-N 2-bromopyridin-3-ol Chemical compound OC1=CC=CN=C1Br YKHQFTANTNMYPP-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 239000006087 Silane Coupling Agent Substances 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SKCNYHLTRZIINA-UHFFFAOYSA-N 2-chloro-5-(chloromethyl)pyridine Chemical compound ClCC1=CC=C(Cl)N=C1 SKCNYHLTRZIINA-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-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
- 244000028419 Styrax benzoin Species 0.000 description 3
- 235000000126 Styrax benzoin Nutrition 0.000 description 3
- 235000008411 Sumatra benzointree Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940022663 acetate Drugs 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- 0 **(*=C)IC1=CN2N[n+]3ccccc3C(C#N)=C2C=C1 Chemical compound **(*=C)IC1=CN2N[n+]3ccccc3C(C#N)=C2C=C1 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-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
- VVWJETKSWYYHER-UHFFFAOYSA-N 2,2-dipyridin-2-ylacetonitrile Chemical compound C=1C=CC=NC=1C(C#N)C1=CC=CC=N1 VVWJETKSWYYHER-UHFFFAOYSA-N 0.000 description 2
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
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- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- MWDGNKGKLOBESZ-UHFFFAOYSA-N 2-oxooctanal Chemical compound CCCCCCC(=O)C=O MWDGNKGKLOBESZ-UHFFFAOYSA-N 0.000 description 2
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 2
- 239000004925 Acrylic resin Substances 0.000 description 2
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- 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
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229920005822 acrylic binder Polymers 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- DRADBSOZTPMFID-UHFFFAOYSA-N benzene-1,2-diol;boron Chemical compound [B].OC1=CC=CC=C1O DRADBSOZTPMFID-UHFFFAOYSA-N 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
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- 238000001035 drying Methods 0.000 description 2
- 150000002081 enamines Chemical class 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
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- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 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
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- FJKOQFIGFHTRRW-UHFFFAOYSA-N (2-methoxy-3-methylphenyl)-(3-methylphenyl)methanone Chemical compound COC1=C(C)C=CC=C1C(=O)C1=CC=CC(C)=C1 FJKOQFIGFHTRRW-UHFFFAOYSA-N 0.000 description 1
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- WKKWHJAMADAFKB-UHFFFAOYSA-N (4-phenylsulfanylphenyl) acetate Chemical compound C1=CC(OC(=O)C)=CC=C1SC1=CC=CC=C1 WKKWHJAMADAFKB-UHFFFAOYSA-N 0.000 description 1
- WBODDOZXDKQEFS-UHFFFAOYSA-N 1,2,3,4-tetramethyl-5-phenylbenzene Chemical group CC1=C(C)C(C)=CC(C=2C=CC=CC=2)=C1C WBODDOZXDKQEFS-UHFFFAOYSA-N 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
- MSAHTMIQULFMRG-UHFFFAOYSA-N 1,2-diphenyl-2-propan-2-yloxyethanone Chemical compound C=1C=CC=CC=1C(OC(C)C)C(=O)C1=CC=CC=C1 MSAHTMIQULFMRG-UHFFFAOYSA-N 0.000 description 1
- DKEGCUDAFWNSSO-UHFFFAOYSA-N 1,8-dibromooctane Chemical compound BrCCCCCCCCBr DKEGCUDAFWNSSO-UHFFFAOYSA-N 0.000 description 1
- ULXPDINNESNIKS-UHFFFAOYSA-N 1-(4-butylphenyl)-2,2-dichloroethanone Chemical compound CCCCC1=CC=C(C(=O)C(Cl)Cl)C=C1 ULXPDINNESNIKS-UHFFFAOYSA-N 0.000 description 1
- JNGALPZRHWQEEZ-UHFFFAOYSA-N 1-(4-phenylsulfanylphenyl)octan-1-one Chemical compound C1=CC(C(=O)CCCCCCC)=CC=C1SC1=CC=CC=C1 JNGALPZRHWQEEZ-UHFFFAOYSA-N 0.000 description 1
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- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- PPFNAOBWGRMDLL-UHFFFAOYSA-N methyl 2-ethoxyacetate Chemical compound CCOCC(=O)OC PPFNAOBWGRMDLL-UHFFFAOYSA-N 0.000 description 1
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 description 1
- YSGBMDFJWFIEDF-UHFFFAOYSA-N methyl 2-hydroxy-3-methylbutanoate Chemical compound COC(=O)C(O)C(C)C YSGBMDFJWFIEDF-UHFFFAOYSA-N 0.000 description 1
- HSDFKDZBJMDHFF-UHFFFAOYSA-N methyl 3-ethoxypropanoate Chemical compound CCOCCC(=O)OC HSDFKDZBJMDHFF-UHFFFAOYSA-N 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N omega-Hydroxydodecanoic acid Natural products OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- LYXOWKPVTCPORE-UHFFFAOYSA-N phenyl-(4-phenylphenyl)methanone Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1C(=O)C1=CC=CC=C1 LYXOWKPVTCPORE-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
Landscapes
- Physics & Mathematics (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials For Photolithography (AREA)
Abstract
하기 화학식 1로 표시되는 화합물, 이를 포함하는 감광성 수지 조성물 및 상기 감광성 수지 조성물을 이용하여 제조되는 컬러필터가 제공된다.
[화학식 1]
(상기 화학식 1에서, 각 치환기는 명세서에 정의된 바와 같다.)There is provided a compound represented by the following Chemical Formula 1, a photosensitive resin composition containing the same, and a color filter manufactured using the photosensitive resin composition.
[Chemical Formula 1]
(Wherein each substituent is as defined in the specification).
Description
본 기재는 신규한 화합물, 이를 포함하는 감광성 수지 조성물 및 컬러필터에 관한 것이다.
The present invention relates to a novel compound, a photosensitive resin composition containing the same, and a color filter.
안료형 감광성 수지 조성물로 제조된 컬러필터에서는 안료 입자 크기에서 비롯되는 휘도와 명암비의 한계가 존재한다. 또한 이미지 센서용 컬러 촬상 소자의 경우에는 미세한 패턴 형성을 위해 더 작은 분산입도를 요구하게 된다. 이와 같은 요구에 부응하고자 안료 대신 입자를 이루지 않는 염료를 도입한 감광성 수지 조성물을 제조하여 휘도와 명암비 등의 색특성이 개선된 컬러필터를 구현하려는 시도가 계속되고 있다.In a color filter made of a pigment type photosensitive resin composition, there is a limit of luminance and contrast ratio resulting from the pigment particle size. Further, in the case of a color imaging device for an image sensor, a smaller dispersion particle size is required for forming a fine pattern. In order to meet such a demand, attempts have been made to fabricate a photosensitive resin composition in which a dye that does not form particles is introduced instead of a pigment, thereby realizing a color filter having improved color characteristics such as brightness and contrast ratio.
따라서, 감광성 수지 조성물의 제조에 사용되는 염료로 적합한 화합물에 대한 연구가 필요한 실정이다.
Therefore, it is necessary to study a compound suitable as a dye used in the production of a photosensitive resin composition.
일 구현예는 신규한 화합물을 제공하기 위한 것이다.One embodiment is to provide a novel compound.
다른 일 구현예는 상기 화합물을 포함하는 감광성 수지 조성물을 제공하기 위한 것이다.Another embodiment is to provide a photosensitive resin composition comprising the above compound.
또 다른 구현예는 상기 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공하기 위한 것이다.
Another embodiment is to provide a color filter manufactured using the photosensitive resin composition.
본 발명의 일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment of the present invention provides a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R8은 각각 독립적으로 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C1 내지 C20 알콕시기 또는 치환 또는 비치환된 C6 내지 C20 헤테로아릴기이고,R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group or a substituted or unsubstituted C6 to C20 heteroaryl group,
M은하기 화학식 2 또는 화학식 3으로 표시되고,M is represented by the formula (2) or (3)
[화학식 2](2)
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.A is a substituted or unsubstituted C6 to C20 aryl group.
상기 R1 내지 R4는 모두 수소 원자이고, 상기 R5 내지 R8는 각각 독립적으로 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C1 내지 C20 알콕시기일 수 있다.Each of R 1 to R 4 is a hydrogen atom, and each of R 5 to R 8 may independently be a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.
상기 R1 내지 R4는 모두 수소 원자이고, 상기 R6은 수소 원자 또는 치환 또는 비치환된 치환된 C1 내지 C20 알킬기이고, 상기 R8은 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알콕시기일 수 있다.Wherein R 1 to R 4 are all hydrogen atoms, R 6 is a hydrogen atom or a substituted or unsubstituted substituted C 1 to C 20 alkyl group, and R 8 is a hydrogen atom or a substituted or unsubstituted C 1 to C 20 alkoxy group have.
상기 화학식 1은 하기 화학식 4 내지 화학식 7 중 어느 하나로 표시될 수 있다.The formula (1) may be represented by any one of the following formulas (4) to (7).
[화학식 4][Chemical Formula 4]
[화학식 5][Chemical Formula 5]
[화학식 6][Chemical Formula 6]
[화학식 7](7)
상기 화학식 4 내지 화학식 7에서,In the above Chemical Formulas 4 to 7,
X1은 N, P 또는 B이고,X < 1 > is N, P or B,
X2 및 X3는 각각 독립적으로, O, S, S(=O) 또는 S(=O)2이고,X 2 and X 3 are each independently O, S, S (= O) or S (= O) 2 ,
L1은 치환 또는 비치환된 C1 내지 C20 알킬렌기이고,L 1 is a substituted or unsubstituted C1 to C20 alkylene group,
L2는 치환 또는 비치환된 C1 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,L 2 is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 헤테로아릴기 또는 시아노기이고,R 9 to R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a cyano group,
M은 하기 화학식 2 또는 화학식 3으로 표시되고,M is represented by the following formula (2) or (3)
[화학식 2](2)
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.A is a substituted or unsubstituted C6 to C20 aryl group.
상기 화학식 1은 하기 화학식 8 내지 화학식 19로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The formula (1) may be represented by any one of the following formulas (8) to (19).
[화학식 8][Chemical Formula 8]
[화학식 9][Chemical Formula 9]
[화학식 10][Chemical formula 10]
[화학식 11](11)
[화학식 12][Chemical Formula 12]
[화학식 13][Chemical Formula 13]
[화학식 14][Chemical Formula 14]
[화학식 15][Chemical Formula 15]
[화학식 16][Chemical Formula 16]
[화학식 17][Chemical Formula 17]
[화학식 18][Chemical Formula 18]
[화학식 19][Chemical Formula 19]
상기 화합물은 황색 염료일 수 있다.The compound may be a yellow dye.
상기 황색 염료는 400nm 내지 550nm의 파장범위에서 최대 흡광영역을 가질 수 있다.The yellow dye may have a maximum light absorption region in the wavelength range of 400 nm to 550 nm.
다른 일 구현예는 상기 화합물을 포함하는 감광성 수지 조성물을 제공한다.Another embodiment provides a photosensitive resin composition comprising the above compound.
상기 감광성 수지 조성물은 안료, 알칼리 가용성 수지, 광중합성 화합물, 광중합 개시제 및 용매를 더 포함할 수 있다.The photosensitive resin composition may further comprise a pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
또 다른 일 구현예는 상기 감광성 수지 조성물을 이용하여 제조되는 컬러필터를 제공한다.Another embodiment provides a color filter manufactured using the photosensitive resin composition.
기타 본 발명의 측면들의 구체적인 사항은 이하의 상세한 설명에 포함되어 있다.
Other aspects of the present invention are included in the following detailed description.
일 구현예에 따른 디피리도메틴계 붕소 화합물은 우수한 황색 분광 특성과 높은 몰흡광계수를 가지고 유기 용매에 대한 용해도가 우수하여, 컬러필터용 감광성 수지 조성물 제조 시 염료로 사용될 수 있고, 상기 염료를 포함하는 컬러필터는 우수한 휘도 및 명암비를 가질 수 있다.
The dipyridomethyl boron compound according to one embodiment has excellent yellow spectral characteristics and a high molar extinction coefficient and is excellent in solubility in an organic solvent and can be used as a dye in the production of a photosensitive resin composition for a color filter, Color filters can have excellent luminance and contrast ratio.
이하, 본 발명의 구현예를 상세히 설명하기로 한다. 다만, 이는 예시로서 제시되는 것으로, 이에 의해 본 발명이 제한되지는 않으며 본 발명은 후술할 청구범위의 범주에 의해 정의될 뿐이다. Hereinafter, embodiments of the present invention will be described in detail. However, it should be understood that the present invention is not limited thereto, and the present invention is only defined by the scope of the following claims.
본 명세서에서 특별한 언급이 없는 한, "치환" 내지 "치환된"이란, 본 발명의 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 알키닐기, 치환 또는 비치환된 지환족 유기기, 치환 또는 비치환된 아릴기, 및 치환 또는 비치환된 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다.Means that at least one hydrogen atom of the functional group of the present invention is substituted with a halogen atom (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group NH 2, NH (R 200), or N (R 201) (R 202), wherein R 200, R 201 and R 202 are the same or different, each independently being a C1 to C10 alkyl groups), amidino group, A substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted alkynyl group, a substituted or unsubstituted alicyclic alkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted aryl group, And a substituted or unsubstituted heterocyclic group substituted with at least one substituent selected from the group consisting of a substituted or unsubstituted heterocyclic group.
본 명세서에서 특별한 언급이 없는 한, "알킬기"란 C1 내지 C20 알킬기를 의미하고, 구체적으로는 C1 내지 C15 알킬기를 의미하고, "사이클로알킬기"란 C3 내지 C20 사이클로알킬기를 의미하고, 구체적으로는 C3 내지 C18 사이클로알킬기를 의미하고, "알콕시기"란 C1 내지 C20 알콕시기를 의미하고, 구체적으로는 C1 내지 C18 알콕시기를 의미하고, "아릴기"란 C6 내지 C20 아릴기를 의미하고, 구체적으로는 C6 내지 C18 아릴기를 의미하고, "알케닐기"란 C2 내지 C20 알케닐기를 의미하고, 구체적으로는 C2 내지 C18 알케닐기를 의미하고, "알킬렌기"란 C1 내지 C20 알킬렌기를 의미하고, 구체적으로는 C1 내지 C18 알킬렌기를 의미하고, "아릴렌기"란 C6 내지 C20 아릴렌기를 의미하고, 구체적으로는 C6 내지 C16 아릴렌기를 의미한다.Unless otherwise specified in the specification, "alkyl group" means C1 to C20 alkyl group, specifically C1 to C15 alkyl group, "cycloalkyl group" means C3 to C20 cycloalkyl group, specifically C3 Refers to a C1 to C20 alkoxy group, specifically, a C1 to C18 alkoxy group, and an "aryl group" means a C6 to C20 aryl group, specifically, a C6 to C20 aryl group, Refers to a C 2 to C 20 alkenyl group, specifically, a C 2 to C 18 alkenyl group, and the "alkylene group" refers to a C 1 to C 20 alkylene group, specifically, a C1 Refers to a C6 to C20 arylene group, and specifically refers to a C6 to C16 arylene group.
본 명세서에서 특별한 언급이 없는 한, "(메타)아크릴레이트"는 "아크릴레이트"와 "메타크릴레이트" 둘 다 가능함을 의미하며, "(메타)아크릴산"은 "아크릴산"과 "메타크릴산" 둘 다 가능함을 의미한다.(Meth) acrylate "refers to both" acrylic acid "and" methacrylic acid " It means both are possible.
본 명세서에서 별도의 정의가 없는 한, "조합"이란 혼합 또는 공중합을 의미한다. 또한 "공중합"이란 블록 공중합 내지 랜덤 공중합을 의미하고, "공중합체"란 블록 공중합체 내지 랜덤 공중합체를 의미한다.As used herein, unless otherwise defined, "combination" means mixing or copolymerization. "Copolymerization" means block copolymerization or random copolymerization, and "copolymer" means block copolymer or random copolymer.
본 명세서 내 화학식에서 별도의 정의가 없는 한, 화학 결합이 그려져야 하는 위치에 화학결합이 그려져 있지 않은 경우는 상기 위치에 수소 원자가 결합되어 있음을 의미한다.Unless otherwise defined in the chemical formulas in this specification, when no chemical bond is drawn at the position where the chemical bond should be drawn, it means that the hydrogen atom is bonded at the above position.
본 명세서에서 별도의 정의가 없는 한, "＊"는 동일하거나 상이한 원자 또는 화학식과 연결되는 부분을 의미한다.Unless otherwise defined herein, "*" means the same or different atom or moiety connected to a formula.
또한, 본 명세서에서 별도의 정의가 없는 한, "최대 흡광영역"이란 최대 흡광도를 나타내는 영역(범위)을 의미한다.
Further, unless otherwise defined in this specification, the "maximum light absorbing region" means a region (range) showing the maximum absorbance.
일 구현예는 하기 화학식 1로 표시되는 화합물을 제공한다.An embodiment provides a compound represented by the following formula (1).
[화학식 1][Chemical Formula 1]
상기 화학식 1에서,In Formula 1,
R1 내지 R8은 각각 독립적으로 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C1 내지 C20 알콕시기 또는 치환 또는 비치환된 C6 내지 C20 헤테로아릴기이고,R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group or a substituted or unsubstituted C6 to C20 heteroaryl group,
M은하기 화학식 2 또는 화학식 3으로 표시되고,M is represented by the formula (2) or (3)
[화학식 2](2)
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.A is a substituted or unsubstituted C6 to C20 aryl group.
상기 화학식 1로 표시되는 화합물은 디피리도메틴계 붕소 화합물로, 우수한 황색 분광 특성과 높은 몰흡광계수를 가지며, 유기용매에 대해 용해도 또한 우수하다. 나아가, 상기 화학식 1로 표시되는 화합물은 고정된 위치에 시아노기를 포함하기 때문에, 디피리도메틴 리간드가 안정하고, 상기 화학식 1로 표시되는 화합물의 내열성, 내화학성 및 공정성이 우수해진다.The compound represented by Formula 1 is a dipyridomethyl boron compound having excellent yellow spectral characteristics and a high molar absorptivity, and is also excellent in solubility in an organic solvent. Further, since the compound represented by Formula 1 includes a cyano group at a fixed position, the dipyridomethyl ligand is stable, and the heat resistance, chemical resistance, and processability of the compound represented by Formula 1 are excellent.
구체적으로 상기 디피리도메틴 리간드는 피리딘 고리의 방향족 안정성 때문에 하기 화학식 X와 같은 이민형태로 존재(즉, 두 개의 피리딘 고리가 sp3 탄소에 의해 연결)하는 반면, 상기 화학식 1로 표시되는 화합물과 같이 고정된 위치에 시아노기가 있으면 하기 화학식 Y와 같은 콘쥬게이션된 엔아민(conjugated enamine) 형태로 존재하게 된다.Specifically, the dipyridomethyl ligand exists in the form of an imine (i.e., two pyridine rings are linked by sp 3 carbon) due to the aromatic stability of the pyridine ring, while the compound represented by the formula (1) If there is a cyano group at a fixed position, it is present in the form of a conjugated enamine such as the following formula (Y).
[화학식 X](X)
[화학식 Y][Formula Y]
이 경우, 디피리도메틴 리간드가 이민 형태가 아닌 콘쥬게이션된 엔아민 형태로 존재하게 될 경우,원하는 분광대를 맞출 수 있으며, 공정성 측면에서 감광성 수지 조성물을 230℃ 이상의 온도에서 포스트 베이킹할 때 상기 시아노기가 블로킹기(blocking group)로서 작용하여 내열성 및 내화학성이 우수해지게 된다.In this case, when the dipyridomethyl ligand is present in the conjugated enamine form rather than in the imine form, the desired aprotic band can be aligned. From the viewpoint of processability, when the photosensitive resin composition is post- The nitrogen gas acts as a blocking group, so that heat resistance and chemical resistance are excellent.
또한, 상기 화학식 1에서,R1 내지 R8은치환 또는 비치환된 아릴기가 아니다. 상기 R1 내지 R8이 치환 또는 비치환된 아릴기인 경우, Pd 계열 촉매를 사용하여 합성해야 하는데 Pd 계열 촉매의 가격이 높아 경제성이 떨어지고, 분광 peak가 넓어(broad) 투과도가 높아야하는 부분에서 오히려 흡광이 일어나 휘도가 저하되며, 전반적으로 PGMEA 등의 유기용매에 대한 용해도가 매우 떨어지게 된다.In Formula 1, R 1 to R 8 are not a substituted or unsubstituted aryl group. When R 1 to R 8 are substituted or unsubstituted aryl groups, it is necessary to synthesize Pd-based catalysts. However, since the cost of Pd-based catalysts is high, economical efficiency is low and broad spectral peaks are required. The light absorption occurs and the luminance is lowered, and the solubility in an organic solvent such as PGMEA is very low.
상기 R1 내지 R4는 모두 수소 원자이고, 상기 R5 내지 R8는 각각 독립적으로 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C1 내지 C20 알콕시기일 수 있다.Each of R 1 to R 4 is a hydrogen atom, and each of R 5 to R 8 may independently be a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, or a substituted or unsubstituted C1 to C20 alkoxy group.
예컨대, 상기 R1 내지 R4는 모두 수소 원자이고, 상기 R6은 수소 원자 또는 치환 또는 비치환된 치환된 C1 내지 C20 알킬기이고, 상기 R8은 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알콕시기일 수 있다.For example, R 1 to R 4 are all hydrogen atoms, R 6 is a hydrogen atom or a substituted or unsubstituted substituted C 1 to C 20 alkyl group, R 8 is a hydrogen atom or a substituted or unsubstituted C 1 to C 20 alkoxy .
상기 화학식 1은 하기 화학식 4 내지 화학식 7 중 어느 하나로 표시될 수 있다.The formula (1) may be represented by any one of the following formulas (4) to (7).
[화학식 4][Chemical Formula 4]
[화학식 5][Chemical Formula 5]
[화학식 6][Chemical Formula 6]
[화학식 7](7)
상기 화학식 4 내지 화학식 7에서,In the above Chemical Formulas 4 to 7,
X1은 N, P 또는 B이고,X < 1 > is N, P or B,
X2 및 X3는 각각 독립적으로, O, S, S(=O) 또는 S(=O)2이고,X 2 and X 3 are each independently O, S, S (= O) or S (= O) 2 ,
L1은 치환 또는 비치환된 C1 내지 C20 알킬렌기이고,L 1 is a substituted or unsubstituted C1 to C20 alkylene group,
L2는 치환 또는 비치환된 C1 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,L 2 is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R9 내지 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 헤테로아릴기 또는 시아노기이고,R 9 to R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a cyano group,
M은하기 화학식 2 또는 화학식 3으로 표시되고,M is represented by the formula (2) or (3)
[화학식 2](2)
[화학식 3](3)
상기 화학식 3에서,In Formula 3,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.A is a substituted or unsubstituted C6 to C20 aryl group.
예컨대, 상기 R9 및 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기일 수 있고, 상기 R10 및 R11은 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 헤테로아릴기 또는 시아노기일 수 있다.For example, R 9 and R 12 may each independently be a substituted or unsubstituted C1 to C20 alkyl group, and each of R 10 and R 11 is independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted A C2 to C20 heteroaryl group or a cyano group.
전술한 바와 같이, 일 구현예에 따른 화합물은 디피리도메틴계 붕소 화합물로, 예컨대 상기 화학식 1로 표시되는 화합물은 디피리도메틴계 이불화 붕소 화합물 또는 디피리도메틴계 카테콜 붕소 화합물일 수 있다.As described above, the compound according to one embodiment is a dipyridomethine-based boron compound. For example, the compound represented by Formula 1 may be a dipyridomethane-based quaternary boron compound or a dipyridomethane-based catechol boron compound.
상기 화학식 1로 표시되는 화합물, 예컨대 상기 디피리도메틴계 이불화 붕소 화합물은 하기 화학식 8 내지 화학식 15로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The compound represented by the formula (1), for example, the dipyridomethane-based boronized boron compound may be represented by any one selected from the group consisting of the following chemical formulas (8) to (15).
[화학식 8][Chemical Formula 8]
[화학식 9][Chemical Formula 9]
[화학식 10][Chemical formula 10]
[화학식 11](11)
[화학식 12][Chemical Formula 12]
[화학식 13][Chemical Formula 13]
[화학식 14][Chemical Formula 14]
[화학식 15][Chemical Formula 15]
상기 화학식 1로 표시되는 화합물, 예컨대 상기 디피리도메틴계 카테콜 붕소 화합물은 하기 화학식 16 내지 화학식 19로 이루어진 군에서 선택된 어느 하나로 표시될 수 있다.The compound represented by Formula 1, for example, the dipyridomethine-based catechol boron compound may be represented by any one selected from the group consisting of the following Chemical Formulas 16 to 19:
[화학식 16][Chemical Formula 16]
[화학식 17][Chemical Formula 17]
[화학식 18][Chemical Formula 18]
[화학식 19][Chemical Formula 19]
일 구현예에 따른 화합물은 고정된 위치에 시아노기를 포함하는 디피리도메틴계 붕소 화합물로서, 적은 양으로도 보다 선명한 색의 발현이 가능하여, 착색제로 사용 시 휘도나 명암비 등의 색특성이 우수한 디스플레이 소자의 제조가 가능하다. 예컨대, 상기 화합물은 착색제, 예컨대 염료, 예컨대 황색 염료, 예컨대 400nm 내지 550nm의 파장범위에서 최대 흡광영역을 가지는 염료일 수 있다.The compound according to one embodiment is a dipyridomethine boron compound containing a cyano group at a fixed position and can express a clearer color even in a small amount, and when used as a colorant, has excellent color characteristics such as luminance and contrast ratio It is possible to manufacture a display device. For example, the compound may be a colorant, such as a dye, such as a yellow dye, e.g., a dye having a maximum light absorbing region in the wavelength range of 400 nm to 550 nm.
일반적으로, 염료는 컬러필터 내에 사용되는 구성성분 중 가장 고가의 구성성분이다. 그러므로, 원하는 효과, 예컨대 고휘도나 고명암비 등을 달성하기 위해서는 고가의 염료를 더 많이 사용해야 하기 때문에 생산 단가가 상승할 수 밖에 없었다. 그러나, 일 구현예에 따른 화합물을 컬러필터 내 염료로 사용하는 경우, 적은 양으로도 고휘도, 고명암비 등의 우수한 색특성을 달성할 수 있어 생산 단가의 절감이 가능하다.In general, dyes are the most expensive component of the components used in color filters. Therefore, in order to achieve a desired effect, for example, a high luminance and a high contrast ratio, it is necessary to use more expensive dye, so that the production cost has to be increased. However, when the compound according to one embodiment is used as a dye in a color filter, excellent color characteristics such as high luminance and high contrast ratio can be achieved even in a small amount, and production cost can be reduced.
다른 일 구현예에 따르면, 상기 일 구현예에 따른 화합물을 포함하는 감광성 수지 조성물을 제공한다.According to another embodiment, there is provided a photosensitive resin composition comprising the compound according to one embodiment.
예컨대, 상기 감광성 수지 조성물은 상기 일 구현예에 따른 화합물, 안료, 알칼리 가용성 수지, 광중합성 화합물, 광중합 개시제 및 용매를 포함할 수 있다.For example, the photosensitive resin composition may include a compound according to one embodiment, a pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
상기 일 구현예에 따른 화합물은 감광성 수지 조성물 내에서 착색제, 예컨대 염료, 예컨대 황색 염료로서의 역할을 하여, 우수한 색특성을 발현할 수 있다.The compound according to one embodiment serves as a coloring agent such as a dye, for example, a yellow dye in the photosensitive resin composition, and can exhibit excellent color characteristics.
일 구현예에 따른 화합물은 상기 감광성 수지 조성물 총량에 대해 1 중량% 내지 10 중량%, 예컨대 3 중량% 내지 7 중량%로 포함될 수 있다. 상기 범위로 일 구현예에 따른 화합물이 포함될 경우 색재현율 및 명암비가 우수해진다. The compound according to one embodiment may be included in an amount of 1 wt% to 10 wt%, for example, 3 wt% to 7 wt% based on the total amount of the photosensitive resin composition. When the compound according to one embodiment is included in the above range, the color reproducibility and the contrast ratio are excellent .
상기 안료는 황색 안료, 녹색 안료 또는 이들의 조합 등을 포함할 수 있으나 이에 한정되는 것은 아니다.예컨대 상기 안료는 안료분산액의 형태로 상기 감광성 수지 조성물에 포함될 수 있다.The pigment may include, but is not limited to, a yellow pigment, a green pigment, a combination thereof, etc. For example, the pigment may be included in the photosensitive resin composition in the form of a pigment dispersion.
상기 안료분산액은 고형분의 안료, 용제 및 상기 용제 내에 상기 안료를 균일하게 분산시키기 위한 분산제를 포함할 수 있다.The pigment dispersion may include a solid pigment, a solvent, and a dispersant for uniformly dispersing the pigment in the solvent.
상기 고형분의 안료는 안료분산액 총량에 대하여 1 중량%내지 20 중량%, 예컨대 8 중량% 내지 20 중량%, 예컨대 15 중량% 내지 20 중량%, 예컨대 8 중량% 내지 15 중량%, 예컨대 10 중량% 내지 20 중량%, 예컨대 10 중량% 내지 15 중량%로 포함될 수 있다.The solid pigment may be present in the pigment dispersion in an amount ranging from 1% to 20%, such as 8% to 20%, such as 15% to 20%, such as 8% to 15% 20% by weight, such as 10% by weight to 15% by weight.
상기 분산제로는 비이온성 분산제, 음이온성 분산제, 양이온성 분산제 등을 사용할 수 있다. 상기 분산제의 구체적인 예로는, 폴리알킬렌글리콜 및 이의 에스테르, 폴리옥시알킬렌, 다가알코올 에스테르 알킬렌 옥사이드 부가물, 알코올알킬렌 옥사이드 부가물, 술폰산 에스테르, 술폰산 염, 카르복실산 에스테르, 카르복실산 염, 알킬아미드 알킬렌 옥사이드 부가물, 알킬 아민 등을 들 수 있으며, 이들을 단독으로 또는 둘 이상 혼합하여 사용할 수 있다.As the dispersing agent, a nonionic dispersing agent, an anionic dispersing agent, a cationic dispersing agent and the like can be used. Specific examples of the dispersing agent include polyalkylene glycols and esters thereof, polyoxyalkylene, polyhydric alcohol ester alkylene oxide adduct, alcohol alkylene oxide adduct, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid Salts, alkylamide alkylene oxide adducts, and alkylamines. These may be used singly or in combination of two or more.
상기 분산제의 시판되는 제품을 예로 들면, BYK社의 DISPERBYK-101, DISPERBYK-130, DISPERBYK-140, DISPERBYK-160, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-165, DISPERBYK-166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 등; EFKA 케미칼社의 EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400, EFKA-450 등; Zeneka社의 Solsperse 5000,Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 등; 또는 Ajinomoto社의 PB711, PB821 등이 있다.DISPERBYK-161, DISPERBYK-160, DISPERBYK-161, DISPERBYK-161, DISPERBYK-162, DISPERBYK-163, DISPERBYK-164, DISPERBYK-160 and DISPERBYK-160 of BYK Co., -166, DISPERBYK-170, DISPERBYK-171, DISPERBYK-182, DISPERBYK-2000, DISPERBYK-2001 and the like; EFKA-47, EFKA-47EA, EFKA-48, EFKA-49, EFKA-100, EFKA-400 and EFKA-450 of EFKA Chemical Co., Solsperse 5000, Solsperse 12000, Solsperse 13240, Solsperse 13940, Solsperse 17000, Solsperse 20000, Solsperse24000GR, Solsperse 27000, Solsperse 28000 from Zeneka; Or Ajinomoto's PB711 and PB821.
상기 분산제는 안료분산액 총량에 대하여 1 중량% 내지 20 중량%로 포함될 수 있다. 분산제가 상기 범위 내로 포함될 경우, 적절한 점도를 유지할 수 있어 감광성 수지 조성물의 분산성이 우수하며, 이로 인해 제품 적용시 광학적, 물리적 및 화학적 품질을 유지할 수 있다.The dispersing agent may be contained in an amount of 1 to 20% by weight based on the total amount of the pigment dispersion. When the dispersing agent is contained within the above range, the dispersibility of the photosensitive resin composition can be maintained because an appropriate viscosity can be maintained, so that optical, physical and chemical quality can be maintained when the product is applied.
상기 안료분산액을 형성하는 용제로는 에틸렌글리콜 아세테이트, 에틸셀로솔브, 프로필렌글리콜 모노메틸에테르아세테이트, 에틸락테이트, 폴리에틸렌글리콜, 사이클로헥사논, 프로필렌글리콜 메틸에테르 등을 사용할 수 있다. As the solvent for forming the pigment dispersion, ethylene glycol acetate, ethyl cellosolve, propylene glycol monomethyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether and the like can be used.
상기 안료분산액은 상기 감광성 수지 조성물 총량에 대하여 10중량% 내지 30 중량%, 예컨대 10 중량% 내지 25 중량%로 포함될 수 있다. 상기 안료분산액이 상기 범위 내로 포함될 경우, 공정마진 확보에 유리하고, 색재현율 및 명암비가 우수해진다.The pigment dispersion may be contained in an amount of 10% by weight to 30% by weight, for example, 10% by weight to 25% by weight based on the total amount of the photosensitive resin composition. When the pigment dispersion is contained within the above range, it is advantageous in securing a process margin and excellent color reproduction ratio and contrast ratio.
상기 알칼리 가용성 수지는 아크릴계 수지일 수 있다.The alkali-soluble resin may be an acrylic resin.
상기 아크릴계 수지는 제1 에틸렌성 불포화 단량체 및 이와 공중합 가능한 제2 에틸렌성 불포화 단량체의 공중합체로, 하나 이상의 아크릴계 반복단위를 포함하는 수지이다. The acrylic resin is a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer, and is a resin containing at least one acrylic repeating unit.
상기 제1 에틸렌성 불포화 단량체는 하나 이상의 카르복시기를 함유하는 에틸렌성 불포화 단량체이며, 이의 구체적인 예로는 아크릴산, 메타크릴산, 말레산, 이타콘산, 푸마르산, 또는 이들의 조합을 들 수 있다.The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group, and specific examples thereof include acrylic acid, methacrylic acid, maleic acid, itaconic acid, fumaric acid, and combinations thereof.
상기 제1 에틸렌성 불포화 단량체는 상기 아크릴계 바인더 수지 총량에 대하여 5 중량% 내지 50 중량%, 예컨대 10 중량% 내지 40 중량%로 포함될 수 있다.The first ethylenically unsaturated monomer may be included in an amount of 5% by weight to 50% by weight, for example, 10% by weight to 40% by weight based on the total amount of the acrylic binder resin.
상기 제2 에틸렌성 불포화 단량체는 스티렌, α-메틸스티렌, 비닐톨루엔, 비닐벤질메틸에테르 등의 방향족 비닐 화합물; 메틸(메타)아크릴레이트, 에틸(메타)아크릴레이트, 부틸(메타)아크릴레이트, 2-히드록시에틸(메타)아크릴레이트, 2-히드록시 부틸(메타)아크릴레이트, 벤질(메타)아크릴레이트, 사이클로헥실(메타)아크릴레이트, 페닐(메타)아크릴레이트 등의 불포화 카르복시산 에스테르 화합물; 2-아미노에틸(메타)아크릴레이트, 2-디메틸아미노에틸(메타)아크릴레이트 등의 불포화 카르복시산 아미노 알킬 에스테르 화합물; 초산비닐, 안식향산 비닐 등의 카르복시산 비닐 에스테르 화합물; 글리시딜(메타)아크릴레이트 등의 불포화 카르복시산 글리시딜 에스테르 화합물; (메타)아크릴로니트릴 등의 시안화 비닐 화합물; (메타)아크릴아미드 등의 불포화 아미드 화합물; 등을 들 수 있으며, 이들을 단독으로 또는 둘 이상 혼합하여 사용할 수 있다.The second ethylenically unsaturated monomer may be an aromatic vinyl compound such as styrene,? -Methylstyrene, vinyltoluene, or vinylbenzyl methyl ether; (Meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, Unsaturated carboxylic acid ester compounds such as cyclohexyl (meth) acrylate and phenyl (meth) acrylate; Unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate and 2-dimethylaminoethyl (meth) acrylate; Carboxylic acid vinyl ester compounds such as vinyl acetate and vinyl benzoate; Unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate; A vinyl cyanide compound such as (meth) acrylonitrile; Unsaturated amide compounds such as (meth) acrylamide; These may be used singly or in combination of two or more.
상기 아크릴계 바인더 수지의 구체적인 예로는 (메타)아크릴산/벤질메타크릴레이트 공중합체, (메타)아크릴산/벤질메타크릴레이트/스티렌 공중합체, (메타)아크릴산/벤질메타크릴레이트/2-히드록시에틸메타크릴레이트 공중합체, (메타)아크릴산/벤질메타크릴레이트/스티렌/2-히드록시에틸메타크릴레이트 공중합체 등을 들 수 있으나, 이에 한정되는 것은 아니며, 이들을 단독 또는 2종 이상을 배합하여 사용할 수도 있다.Specific examples of the acrylic binder resin include (meth) acrylic acid / benzyl methacrylate copolymer, (meth) acrylic acid / benzyl methacrylate / styrene copolymer, (meth) acrylic acid / benzyl methacrylate / 2- Acrylate copolymer, a (meth) acrylic acid / benzyl methacrylate / styrene / 2-hydroxyethyl methacrylate copolymer, and the like, but not limited thereto, and they may be used alone or in combination have.
상기 알칼리 가용성 수지의 중량평균 분자량은 3,000 g/mol 내지 150,000 g/mol, 예컨대 5,000 g/mol 내지 50,000 g/mol, 예컨대 20,000 g/mol 내지 30,000 g/mol 일 수 있다. 상기 알칼리 가용성 수지의 중량평균 분자량이 상기 범위 내일 경우, 상기 감광성 수지 조성물의 물리적 및 화학적 물성이 우수하고 점도가 적절하며, 컬러필터 제조시 기판과의 밀착성이 우수하다. The weight-average molecular weight of the alkali-soluble resin may be from 3,000 g / mol to 150,000 g / mol, such as from 5,000 g / mol to 50,000 g / mol, such as from 20,000 g / mol to 30,000 g / mol. When the weight average molecular weight of the alkali-soluble resin is within the above range, the photosensitive resin composition has excellent physical and chemical properties, is suitable in viscosity, and has excellent adhesion with a substrate in the production of a color filter.
상기 알칼리 가용성 수지의 산가는 15 mgKOH/g 내지 60 mgKOH/g, 예컨대 20 mgKOH/g 내지 50 mgKOH/g 일 수 있다. 알칼리 가용성 수지의 산가가 상기 범위 내일 경우 픽셀 패턴의 해상도가 우수하다.The acid value of the alkali-soluble resin may be from 15 mgKOH / g to 60 mgKOH / g, for example, from 20 mgKOH / g to 50 mgKOH / g. When the acid value of the alkali-soluble resin is within the above range, the resolution of the pixel pattern is excellent.
상기 알칼리 가용성 수지는 상기 감광성 수지 조성물 총량에 대하여 1 중량% 내지 30 중량%, 예컨대 1 중량% 내지 15 중량%로 포함될 수 있다. 알칼리 가용성 수지가 상기 범위 내로 포함될 경우, 컬러필터 제조시 현상성이 우수하며 가교성이 개선되어 우수한 표면 평활도를 얻을 수 있다.The alkali-soluble resin may be contained in an amount of 1% by weight to 30% by weight, for example, 1% by weight to 15% by weight based on the total amount of the photosensitive resin composition. When the alkali-soluble resin is contained within the above-mentioned range, the color filter is excellent in developability in the production of a color filter, and the cross-linkability is improved, whereby excellent surface smoothness can be obtained.
상기 광중합성 화합물은 적어도 1개의 에틸렌성 불포화 이중결합을 가지는 (메타)아크릴산의 일관능 또는 다관능 에스테르가 사용될 수 있다.The photopolymerizable compound may be a monofunctional or polyfunctional ester of (meth) acrylic acid having at least one ethylenically unsaturated double bond.
광중합성 화합물은 상기 에틸렌성 불포화 이중결합을 가짐으로써, 패턴 형성 공정에서 노광시 충분한 중합을 일으킴으로써 내열성, 내광성 및 내화학성이 우수한 패턴을 형성할 수 있다.By having the ethylenically unsaturated double bond, the photopolymerizable compound can form a pattern having excellent heat resistance, light resistance and chemical resistance by causing sufficient polymerization during exposure in the pattern formation step.
광중합성 화합물의 구체적인 예로는, 에틸렌 글리콜 디(메타)아크릴레이트, 디에틸렌 글리콜 디(메타)아크릴레이트, 트리에틸렌 글리콜 디(메타)아크릴레이트, 프로필렌 글리콜 디(메타)아크릴레이트, 네오펜틸 글리콜 디(메타)아크릴레이트, 1,4-부탄디올 디(메타)아크릴레이트, 1,6-헥산디올 디(메타)아크릴레이트, 비스페놀A 디(메타)아크릴레이트, 펜타에리트리톨 디(메타)아크릴레이트, 펜타에리트리톨 트리(메타)아크릴레이트, 펜타에리트리톨 테트라(메타)아크릴레이트, 펜타에리트리톨 헥사(메타)아크릴레이트, 디펜타에리트리톨 디(메타)아크릴레이트, 디펜타에리트리톨 트리(메타)아크릴레이트, 디펜타에리트리톨 펜타(메타)아크릴레이트, 디펜타에리트리톨 헥사(메타)아크릴레이트, 비스페놀A 에폭시(메타)아크릴레이트, 에틸렌 글리콜 모노메틸에테르 (메타)아크릴레이트, 트리메틸올 프로판 트리(메타)아크릴레이트, 트리스(메타)아크릴로일옥시에틸 포스페이트, 노볼락에폭시 (메타)아크릴레이트 등을 들 수 있다. Specific examples of the photopolymerizable compound include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, neopentyl glycol di (Meth) acrylate, 1,6-hexanediol di (meth) acrylate, bisphenol A di (meth) acrylate, pentaerythritol di (meth) acrylate, (Meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (Meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol A epoxy (meth) acrylate, ethylene glycol monomethacrylate (Meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, novolac epoxy (meth) acrylate and the like.
광중합성 화합물의 시판되는 제품을 예로 들면 다음과 같다. 상기 (메타)아크릴산의 일관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-101®, 동 M-111®, 동 M-114® 등; 니혼 가야꾸(주)社의 KAYARAD TC-110S®, 동 TC-120S® 등; 오사카 유끼 가가꾸 고교(주)社의 V-158®, V-2311® 등을 들 수 있다. 상기 (메타)아크릴산의 이관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-210®, 동 M-240®, 동 M-6200® 등; 니혼 가야꾸(주)社의 KAYARAD HDDA®, 동 HX-220®, 동 R-604® 등; 오사카 유끼 가가꾸 고교(주)社의 V-260®, V-312®, V-335 HP® 등을 들 수 있다. 상기 (메타)아크릴산의 삼관능 에스테르의 예로는, 도아 고세이 가가꾸 고교(주)社의 아로닉스 M-309®, 동 M-400®, 동 M-405®, 동 M-450®, 동 M-710®, 동 M-8030®, 동 M-8060® 등; 니혼 가야꾸(주)社의 KAYARAD TMPTA®, 동 DPCA-20®, 동-30®, 동-60®, 동-120® 등; 오사카 유끼 가야꾸 고교(주)社의 V-295®, 동-300®, 동-360®, 동-GPT®, 동-3PA®, 동-400® 등을 들 수 있다. 상기 제품을 단독 사용 또는 2종 이상 함께 사용할 수 있다.Examples of commercially available products of photopolymerizable compounds are as follows. The (meth) acrylic acid is one example of a polyfunctional ester, such as doah Gosei Kagaku Kogyo's (primary)社Aronix M-101 ®, the same M-111 ®, the same M-114 ®; KAYARAD TC-110S ® and TC-120S ® from Nihon Kayaku Co., Ltd.; Osaka yukki the like Kagaku Kogyo (main)社of V-158 ®, V-2311 ®. The (meth) transfer function of an example esters of acrylic acid are, doah Gosei Kagaku Kogyo (Note)社of Aronix M-210 ®, copper or the like M-240 ®, the same M-6200 ®; KAYARAD HDDA ® , HX-220 ® and R-604 ® from Nihon Kayaku Corporation; Osaka yukki the like Kagaku Kogyo Co., Ltd. of 社V-260 ®, V- 312 ®, V-335 HP ®. Examples of the tri-functional ester of (meth) acrylic acid, doah Gosei Kagaku Kogyo (Note)社of Aronix M-309 ®, the same M-400 ®, the same M-405 ®, the same M-450 ®, Dong M -710 ® , copper M-8030 ® , copper M-8060 ® and the like; Nippon Kayaku (Note)社of KAYARAD TMPTA ®, copper DPCA-20 ®, ® copper -30, -60 ® copper, copper ® -120 and the like; Osaka yukki Kayaku high (primary)社of V-295 ®, copper ® -300, -360 ® copper, copper -GPT ®, copper -3PA ®, and the like copper -400 ®. These products may be used alone or in combination of two or more.
상기 광중합성 화합물은 보다 우수한 현상성을 부여하기 위하여 산무수물로 처리하여 사용할 수도 있다.The photopolymerizable compound may be treated with an acid anhydride so as to give better developing properties.
상기 광중합성 화합물은 상기 감광성 수지 조성물 총량에 대하여 1 중량% 내지 15 중량%, 예컨대 5 중량% 내지 10 중량%로 포함될 수 있다. 광중합성 화합물이 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광시 경화가 충분히 일어나 신뢰성이 우수하며, 알칼리 현상액에의 현상성이 우수하다.The photopolymerizable compound may be contained in an amount of 1 wt% to 15 wt%, for example, 5 wt% to 10 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerizable compound is contained within the above-mentioned range, the pattern forming process sufficiently cures upon exposure to light, which is excellent in reliability and developability in an alkaline developer.
상기 광중합 개시제는 감광성 수지 조성물에 일반적으로 사용되는 개시제로서, 예를 들어 아세토페논계 화합물, 벤조페논계 화합물, 티오크산톤계 화합물, 벤조인계 화합물, 옥심계 화합물, 또는 이들의 조합을 사용할 수 있다. The photopolymerization initiator may be, for example, an acetophenone-based compound, a benzophenone-based compound, a thioxanthone-based compound, a benzoin-based compound, an oxime-based compound, or a combination thereof as an initiator generally used in a photosensitive resin composition .
상기 아세토페논계의 화합물의 예로는, 2,2'-디에톡시 아세토페논, 2,2'-디부톡시 아세토페논, 2-히드록시-2-메틸프로피오페논, p-t-부틸트리클로로 아세토페논, p-t-부틸디클로로 아세토페논, 4-클로로 아세토페논, 2,2'-디클로로-4-페녹시 아세토페논, 2-메틸-1-(4-(메틸티오)페닐)-2-모폴리노프로판-1-온, 2-벤질-2-디메틸아미노-1-(4-모폴리노페닐)-부탄-1-온 등을 들 수 있다.Examples of the acetophenone-based compound include 2,2'-diethoxyacetophenone, 2,2'-dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, pt-butyltrichloroacetophenone, dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropanone, p-butyldichloroacetophenone, 1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one.
상기 벤조페논계 화합물의 예로는, 벤조페논, 벤조일 안식향산, 벤조일 안식향산 메틸, 4-페닐 벤조페논, 히드록시 벤조페논, 아크릴화 벤조페논, 4,4'-비스(디메틸 아미노)벤조페논, 4,4'-비스(디에틸아미노)벤조페논, 4,4'-디메틸아미노벤조페논, 4,4'-디클로로벤조페논, 3,3'-디메틸-2-메톡시벤조페논 등을 들 수 있다.Examples of the benzophenone compound include benzophenone, benzoyl benzoic acid, methyl benzoyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4,4'-bis (dimethylamino) benzophenone, '-Bis (diethylamino) benzophenone, 4,4'-dimethylaminobenzophenone, 4,4'-dichlorobenzophenone, and 3,3'-dimethyl-2-methoxybenzophenone.
상기 티오크산톤계 화합물의 예로는, 티오크산톤, 2-메틸티오크산톤, 이소프로필 티오크산톤, 2,4-디에틸 티오크산톤, 2,4-디이소프로필 티오크산톤, 2-클로로티오크산톤 등을 들 수 있다.Examples of the thioxanthone compound include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, 2- Chlorothioxanthone and the like.
상기 벤조인계 화합물의 예로는, 벤조인, 벤조인 메틸 에테르, 벤조인 에틸 에테르, 벤조인 이소프로필 에테르, 벤조인 이소부틸 에테르, 벤질디메틸케탈 등을 들 수 있다.Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and benzyl dimethyl ketal.
상기 트리아진계 화합물의 예로는, 2,4,6-트리클로로-s-트리아진, 2-페닐 4,6-비스(트리클로로메틸)-s-트리아진, 2-(3', 4'-디메톡시스티릴)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(4'-메톡시나프틸)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-메톡시페닐)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(p-톨릴)-4,6-비스(트리클로로 메틸)-s-트리아진, 2-비페닐 4,6-비스(트리클로로 메틸)-s-트리아진, 비스(트리클로로메틸)-6-스티릴-s-트리아진, 2-(나프토-1-일)-4,6-비스(트리클로로메틸)-s-트리아진, 2-(4-메톡시나프토-1-일)-4,6-비스(트리클로로메틸)-s-트리아진, 2-4-비스(트리클로로메틸)-6-피페로닐-s-트리아진, 2-4-비스(트리클로로메틸)-6-(4-메톡시스티릴)-s-트리아진 등을 들 수 있다.Examples of the triazine-based compound include 2,4,6-trichloro-s-triazine, 2-phenyl 4,6-bis (trichloromethyl) (Trichloromethyl) -s-triazine, 2- (4'-methoxynaphthyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) Bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphtho- Bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphtho-1-yl) (Trichloromethyl) -6- (4-methoxystyryl) -s-triazine, and the like.
상기 옥심계 화합물의 예로는, O-아실옥심계 화합물, 2-(o-벤조일옥심)-1-[4-(페닐티오)페닐]-1,2-옥탄디온, 1-(o-아세틸옥심)-1-[9-에틸-6-(2-메틸벤조일)-9H-카르바졸-3-일]에탄온, O-에톡시카르보닐-α-옥시아미노-1-페닐프로판-1-온 등을 사용할 수 있다. 상기 O-아실옥심계 화합물의 구체적인 예로는, 1,2-옥탄디온, 2-디메틸아미노-2-(4-메틸벤질)-1-(4-모르폴린-4-일-페닐)-부탄-1-온, 1-(4-페닐술파닐페닐)-부탄-1,2-디온2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1,2-디온2-옥심-O-벤조에이트, 1-(4-페닐술파닐페닐)-옥탄-1-온옥심-O-아세테이트 및 1-(4-페닐술파닐페닐)-부탄-1-온옥심-O-아세테이트 등을 들 수 있다. Examples of the oxime compounds include O-acyloxime compounds, 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl] -1,2-octanedione, 1- ) -1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone, O-ethoxycarbonyl- Etc. may be used. Specific examples of the O-acyloxime-based compound include 1,2-octanedione, 2-dimethylamino-2- (4-methylbenzyl) -1- (4-morpholin- (4-phenylsulfanylphenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- -Oxime-O-benzoate, 1- (4-phenylsulfanylphenyl) -octane-1-one oxime-O-acetate and 1- (4-phenylsulfanylphenyl) Acetate and the like.
상기 광중합 개시제는 상기 화합물 이외에도 카바졸계 화합물, 디케톤류 화합물, 술포늄 보레이트계 화합물, 디아조계 화합물, 이미다졸계 화합물, 비이미다졸계 화합물 등을 사용할 수 있다.The photopolymerization initiator may be a carbazole compound, a diketone compound, a sulfonium borate compound, a diazo compound, an imidazole compound, or a nonimidazole compound in addition to the above compounds.
상기 광중합 개시제는 빛을 흡수하여 들뜬 상태가 된 후 그 에너지를 전달함으로써 화학반응을 일으키는 광 증감제와 함께 사용될 수도 있다.The photopolymerization initiator may be used in combination with a photosensitizer that generates a chemical reaction by absorbing light to be in an excited state and transferring its energy.
상기 광 증감제의 예로는, 테트라에틸렌글리콜 비스-3-머캡토 프로피오네이트, 펜타에리트리톨 테트라키스-3-머캡토 프로피오네이트, 디펜타에리트리톨 테트라키스-3-머캡토 프로피오네이트 등을 들 수 있다. Examples of the photosensitizer include tetraethylene glycol bis-3-mercaptopropionate, pentaerythritol tetrakis-3-mercaptopropionate, dipentaerythritol tetrakis-3-mercaptopropionate and the like .
상기 광중합 개시제는 상기 감광성 수지 조성물 총량에 대하여 0.01 중량% 내지 10 중량%, 예컨대 0.1 중량% 내지 5 중량%로 포함될 수 있다. 광중합 개시제가 상기 범위 내로 포함될 경우, 패턴 형성 공정에서 노광시 경화가 충분히 일어나 우수한 신뢰성을 얻을 수 있으며, 패턴의 내열성, 내광성 및 내화학성이 우수하고, 해상도 및 밀착성 또한 우수하며, 미반응 개시제로 인한 투과율의 저하를 막을 수 있다.The photopolymerization initiator may be included in an amount of 0.01 wt% to 10 wt%, for example, 0.1 wt% to 5 wt% with respect to the total amount of the photosensitive resin composition. When the photopolymerization initiator is contained within the above range, the photopolymerization initiator is sufficiently cured upon exposure in the pattern formation step to obtain excellent reliability, and the pattern is excellent in heat resistance, light resistance, chemical resistance, resolution and adhesion, It is possible to prevent the transmittance from being lowered.
상기 용매는 일 구현예에 따른 화합물, 안료, 알칼리 가용성 수지, 광중합성 화합물 및 광중합 개시제와의 상용성을 가지되 반응하지 않는 물질들이 사용될 수 있다.The solvent may be a compound, a pigment, an alkali-soluble resin, a photopolymerizable compound, and a compound having compatibility with a photopolymerization initiator but not reacting with the compound according to one embodiment.
상기 용매의 예로는, 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 알킬에스테르류; 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 프로피온산 메틸, 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-메틸 프로피온산 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-메틸포름아닐라드, 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 등의 고비점 용매를 들 수 있다.Examples of the solvent include alcohols such as methanol and ethanol; Ethers such as dichloroethyl ether, n-butyl ether, diisobutyl 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 methylethylcarbitol, diethylcarbitol, 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- ; 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; Alkoxyacetic acid alkyl esters such as methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, and ethyl ethoxyacetate; 3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate; 3-alkoxypropionic acid alkyl esters such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, ethyl 3-ethoxypropionate and methyl 3-ethoxypropionate; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate and propyl 2-oxypropionate; 2-alkoxypropionic acid alkyl esters such as methyl 2-methoxypropionate, ethyl 2-methoxypropionate, ethyl 2-ethoxypropionate and methyl 2-ethoxypropionate; 2-methylpropionic acid esters such as methyl 2-oxy-2-methylpropionate and ethyl 2-oxy-2-methylpropionate, methyl 2-methoxy- Monooximonocarboxylic acid alkyl esters of 2-alkoxy-2-methylpropionic acid alkyls such as ethyl methyl propionate; Esters such as ethyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate and methyl 2-hydroxy-3-methylbutanoate; Ketone acid esters such as ethyl pyruvate, and the like, and also include N-methylformamide, N, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N, N-dimethylacetamide , N-methylpyrrolidone, dimethylsulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, And high boiling solvents such as ethyl acetate, diethyl oxalate, diethyl maleate,? -Butyrolactone, ethylene carbonate, propylene carbonate, and phenyl cellosolve acetate.
이들 중 좋게는 상용성 및 반응성을 고려하여, 에틸렌 글리콜 모노에틸에테르 등의 글리콜 에테르류; 에틸 셀로솔브 아세테이트 등의 에틸렌 글리콜 알킬에테르 아세테이트류; 2-히드록시 프로피온산 에틸 등의 에스테르류; 디에틸렌 글리콜 모노메틸에테르 등의 카르비톨류; 프로필렌 글리콜 모노메틸에테르 아세테이트, 프로필렌 글리콜 프로필에테르 아세테이트 등의 프로필렌 글리콜 알킬에테르 아세테이트류가 사용될 수 있다.Among them, glycol ethers such as ethylene glycol monoethyl ether and the like are preferably used in consideration of compatibility and reactivity; Ethylene glycol alkyl ether acetates such as ethyl cellosolve acetate; Esters such as ethyl 2-hydroxypropionate; Carbitols such as diethylene glycol monomethyl ether; Propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate and propylene glycol propyl ether acetate can be used.
상기 용매는 상기 감광성 수지 조성물 총량에 대하여 잔부량, 예컨대 30 중량% 내지 80 중량%로 포함될 수 있다. 용매가 상기 범위 내로 포함될 경우 상기 감광성 수지 조성물이 적절한 점도를 가짐에 따라 컬러필터 제조시 공정성이 우수하다.The solvent may be contained in an amount of 30% by weight to 80% by weight based on the total amount of the photosensitive resin composition. When the solvent is contained within the above range, the photosensitive resin composition has an appropriate viscosity, and thus the processability in the production of the color filter is excellent.
다른 일 구현예에 따른 감광성 수지 조성물은 기판과의 밀착성 등을 개선하기 위해 에폭시 화합물을 더 포함할 수 있다. The photosensitive resin composition according to another embodiment may further include an epoxy compound to improve adhesion with the substrate.
상기 에폭시 화합물의 예로는, 페놀 노볼락 에폭시 화합물, 테트라메틸 비페닐 에폭시 화합물, 비스페놀 A형 에폭시 화합물, 지환족 에폭시화합물 또는 이들의 조합을 들 수 있다.Examples of the epoxy compound include a phenol novolak epoxy compound, a tetramethylbiphenyl epoxy compound, a bisphenol A type epoxy compound, an alicyclic epoxy compound, or a combination thereof.
상기 에폭시 화합물은 감광성 수지 조성물 100 중량부에 대하여 0.01 중량부 내지 20 중량부, 예컨대 0.1 중량부 내지 10 중량부로 포함될 수 있다. 에폭시 화합물이 상기 범위 내로 포함될 경우 밀착성, 저장성 등이 우수하다. The epoxy compound may be contained in an amount of 0.01 to 20 parts by weight, for example, 0.1 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the epoxy compound is contained within the above range, the adhesiveness and storage stability are excellent.
또한 상기 감광성 수지 조성물은 기판과의 접착성을 향상시키기 위해 카르복실기, 메타크릴로일기, 이소시아네이트기, 에폭시기 등의 반응성 치환기를 갖는 실란 커플링제를 더 포함할 수 있다.The photosensitive resin composition may further include a silane coupling agent having a reactive substituent such as a carboxyl group, a methacryloyl group, an isocyanate group or an epoxy group in order to improve the adhesiveness to the substrate.
상기 실란 커플링제의 예로는, 트리메톡시실릴 벤조산, γ-메타크릴 옥시프로필 트리메톡시실란, 비닐 트리아세톡시실란, 비닐 트리메톡시실란, γ-이소시아네이트 프로필 트리에톡시실란, γ-글리시독시 프로필 트리메톡시실란, β-(3,4-에폭시사이클로헥실)에틸트리메톡시실란 등을 들 수 있으며, 이들을 단독 또는 2종 이상 혼합하여 사용할 수 있다. Examples of the silane coupling agent include trimethoxysilylbenzoic acid,? -Methacryloxypropyltrimethoxysilane, vinyltriacetoxysilane, vinyltrimethoxysilane,? -Isocyanatepropyltriethoxysilane,? -Glycidoxine (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc. These may be used alone or in combination of two or more.
상기 실란 커플링제는 감광성 수지 조성물 100 중량부에 대하여 0.01 중량부 내지 10 중량부로 포함될 수 있다. 실란 커플링제가 상기 범위 내로 포함될 경우 밀착성, 저장성 등이 우수하다. The silane coupling agent may be contained in an amount of 0.01 to 10 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the silane coupling agent is contained within the above range, the adhesion and storage stability are excellent.
또한 상기 감광성 수지 조성물은 필요에 따라 코팅성 향상 및 결점 생성 방지 효과를 위해 계면 활성제를 더 포함할 수 있다. The above-mentioned photosensitive resin composition may further contain a surfactant for improving coatability and preventing defect formation if necessary.
상기 계면활성제의 예로는, BM Chemie社의 BM-1000®, BM-1100® 등; 다이 닛폰 잉키 가가꾸 고교(주)社의 메카 팩 F 142D®, 동 F 172®, 동 F 173®, 동 F 183® 등; 스미토모 스리엠(주)社의 프로라드 FC-135®, 동 FC-170C®, 동 FC-430®, 동 FC-431® 등; 아사히 그라스(주)社의 사프론 S-112®, 동 S-113®, 동 S-131®, 동 S-141®, 동 S-145® 등; 도레이 실리콘(주)社의 SH-28PA®, 동-190®, 동-193®, SZ-6032®, SF-8428® 등의 명칭으로 시판된고 있는 불소계 계면 활성제를 사용할 수 있다.Examples of the surfactants include, BM Chemie BM-1000 ® of社, BM-1100 ®, and the like; Mechacup F 142D ® , copper F 172 ® , copper F 173 ® , copper F 183 ® and the like manufactured by Dainippon Ink & Chemicals Incorporated; Sumitomo M. (Note)社Pro rod FC-135 ®, the same FC-170C ®, copper FC-430 ®, the same FC-431 ®, and the like; Asahi Grass Co., Saffron S-112 ® of社, such S-113 ®, the same S-131 ®, the same S-141 ®, the same S-145 ®, and the like; Toray silicone (Note)社SH-28PA ®, copper -190 ®, may be used copper ® -193, fluorine-based surfactants and commercially available under the name, such as SZ-6032 ®, SF-8428 ®.
상기 계면 활성제는 감광성 수지 조성물 100 중량부에 대하여 0.001 중량부 내지 5 중량부로 사용될 수 있다. 계면 활성제가 상기 범위 내로 포함될 경우 코팅 균일성이 확보되고, 얼룩이 발생하지 않으며, 유리 기판에 대한 습윤성(wetting)이 우수하다.The surfactant may be used in an amount of 0.001 part by weight to 5 parts by weight based on 100 parts by weight of the photosensitive resin composition. When the surfactant is contained within the above range, uniformity of coating is ensured, no staining occurs, and wetting of the glass substrate is excellent.
또한 상기 감광성 수지 조성물은 물성을 저해하지 않는 범위 내에서 산화방지제, 안정제 등의 기타 첨가제가 일정량 첨가될 수도 있다.The photosensitive resin composition may contain a certain amount of other additives such as an antioxidant and a stabilizer within a range that does not impair the physical properties.
또 다른 일 구현예에 따르면, 상기 일 구현예에 따른 감광성 수지 조성물을 이용하여 제조된 컬러필터를 제공한다. According to another embodiment, there is provided a color filter manufactured using the photosensitive resin composition according to one embodiment.
상기 컬러필터 내 패턴 형성 공정은 다음과 같다.The pattern forming process in the color filter is as follows.
상기 감광성 수지 조성물을 지지 기판상에 스핀 코팅, 슬릿 코팅, 잉크젯 프린팅 등으로 도포하는 공정; 상기 도포된 감광성 수지 조성물을 건조하여 감광성 수지 조성물 막을 형성하는 공정; 상기 감광성 수지 조성물 막을 노광하는 공정; 상기 노광된 감광성 수지 조성물 막을 알칼리 수용액으로 현상하여 감광성 수지막을 제조하는 공정; 및 상기 감광성 수지막을 가열 처리하는 공정을 포함한다. 상기 공정 상의 조건 등에 대하여는 당해 분야에서 널리 알려진 사항이므로, 본 명세서에서 자세한 설명은 생략하기로 한다.
Applying the photosensitive resin composition on a support substrate by spin coating, slit coating, inkjet printing or the like; Drying the applied photosensitive resin composition to form a photosensitive resin composition film; Exposing the photosensitive resin composition film; Developing the exposed photosensitive resin composition film with an aqueous alkali solution to produce a photosensitive resin film; And a step of heat-treating the photosensitive resin film. The process conditions and the like are well known in the art, and therefore, detailed description thereof will be omitted herein.
이하, 실시예를 들어 본 발명에 대해서 더욱 상세하게 설명할 것이나, 하기의 실시예는 본 발명의 바람직한 실시예일 뿐 본 발명이 하기 실시예에 한정되는 것은 아니다.
EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples. However, the following Examples are only the preferred embodiments of the present invention, and the present invention is not limited to the following Examples.
(화합물의 합성)(Synthesis of Compound)
합성예Synthetic example 1: 화학식 12로 표시되는 화합물의 합성 1: Synthesis of the compound represented by the formula (12)
(1) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간동안 교반하였다. 이 후, 2-Bromo-3-(2-ethylhexyloxy)pyridine(4.58g)을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드([3-(2-Ethyl-hexyloxy)-1H-pyridin-2-ylidene]-pyridin-2-yl-acetonitrile)를 얻었다.(1) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Then, 2-bromo-3- (2-ethylhexyloxy) pyridine (4.58 g) was added and stirred under reflux. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during the extraction process and separated by column chromatography to obtain a precursor ligand ([3- (2-Ethyl-hexyloxy) -1H-pyridin-2-ylidene] -pyridin-2-yl-acetonitrile ).
(2) 상기 과정 (1)에서 얻은 전구체 리간드([3-(2-Ethyl-hexyloxy)-1H-pyridin-2-ylidene]-pyridin-2-yl-acetonitrile) 0.97g을 dichloromethane(100mL)에 녹인 후, 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼크로마토그래피로 분리하여하기 화학식 12로 표시되는 화합물을 얻었다.(2) 0.97 g of the precursor ligand (3- (2-Ethyl-hexyloxy) -1H-pyridin-2-ylidene] -pyridin-2-yl- acetonitrile obtained in the above step (1) was dissolved in dichloromethane After that, triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (12).
[화학식 12][Chemical Formula 12]
1H NMR (300 MHz, CDCl3) δ0.93(6H), 1.38 (9H), 4.00 (2H), 6.88 (1H), 6.96 (1H), 7.04 (1H), 7.72 (1H), 7.83 (2H), 8.19 (1H)
1 H NMR (300 MHz, CDCl 3) δ 0.93 (6H), 1.38 (9H), 4.00 (2H), 6.88 (1H), 6.96 (1H), 7.04 (1H), 7.72 (1H), 7.83 (2H) , 8.19 (1H)
합성예Synthetic example 2: 화학식 8로 표시되는 화합물의 합성 2: Synthesis of Compound Represented by Formula 8
(1) 2-Bromo-3-hydroxypyridine(5.19g), Benzyl bromide(5.1g), Potassium carbonate(4.84g)을 DMF에 녹이고, 80℃에서 교반한다. Dichloromethane으로 추출 후, 컬럼 크로마토그래피를 이용하여 중간체인 2-Bromo-3-(2-Benzyloxy)pyridine를 얻었다.(1) 2-Bromo-3-hydroxypyridine (5.19 g), Benzyl bromide (5.1 g) and Potassium carbonate (4.84 g) are dissolved in DMF and stirred at 80 ° C. After extraction with dichloromethane, the intermediate 2-bromo-3- (2-benzyloxy) pyridine was obtained by column chromatography.
(2) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간동안 교반하였다. 이 후, 상기 과정 (1)에서 얻은 중간체인 2-Bromo-3-(2-Benzyloxy)pyridine(3.72g)을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻었다.(2) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 2-bromo-3- (2-benzyloxy) pyridine (3.72 g) as an intermediate obtained in the above step (1) is added and stirred under reflux. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(3) 상기 과정 (2)에서 얻은 전구체 리간드 1.43g을 dichloromethane(100mL)에 녹인 후, 여기에 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 8로 표시되는 화합물을 얻었다.(3) 1.43 g of the precursor ligand obtained in the above step (2) was dissolved in dichloromethane (100 mL), and then triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following general formula (8).
[화학식 8][Chemical Formula 8]
1H NMR (300 MHz, CDCl3) δ 5.33 (2H), 6.79 (1H), 7.00 (2H), 7.40 (3H), 7.52 (2H), 7.74 (1H), 7.83 (2H), 8.20 (1H)
1 H NMR (300 MHz, CDCl 3) δ 5.33 (2H), 6.79 (1H), 7.00 (2H), 7.40 (3H), 7.52 (2H), 7.74 (1H), 7.83 (2H), 8.20 (1H)
합성예Synthetic example 3: 화학식 9로 표시되는 화합물의 합성 3: Synthesis of Compound Represented by Formula 9
(1) 2-Bromo-3-hydroxypyridine(5.19g), 1-Bromoethylbenzene(5.55g), Potassium carbonate(4.84g)을 DMF에 녹이고, 80℃에서 교반한다. Dichloromethane으로 추출 후, 컬럼 크로마토그래피를 이용하여 중간체를 얻었다.(1) 2-Bromo-3-hydroxypyridine (5.19 g), 1-bromoethylbenzene (5.55 g) and Potassium carbonate (4.84 g) were dissolved in DMF and stirred at 80 ° C. After extraction with dichloromethane, an intermediate was obtained by column chromatography.
(2) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간 동안 교반하였다. 이 후, 상기 과정 (1)에서 얻은 중간체 3.97g을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻었다.(2) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 3.97 g of the intermediate obtained in the above step (1) was added and stirred while refluxing. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(3) 상기 과정 (2)에서 얻은 전구체 리간드 1.5g을 dichloromethane(100mL)에 녹인 후, 여기에 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 9로 표시되는 화합물을 얻었다.(3) 1.5 g of the precursor ligand obtained in the above step (2) was dissolved in dichloromethane (100 mL), and then triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following general formula (9).
[화학식 9][Chemical Formula 9]
GC-MS(DI) m/z: 349.13
GC-MS (DI) m / z: 349.13
합성예Synthetic example 4: 화학식 10으로 표시되는 화합물의 합성 4: Synthesis of Compound Represented by Formula 10
(1) 2-Bromo-3-hydroxypyridine(5.19g), 1-Bromo-2-methylpropane(4.11g), Potassium carbonate(4.84g)을 DMF에 녹이고, 80℃에서 교반한다. Dichloromethane으로 추출 후, 컬럼 크로마토그래피를 이용하여 중간체를 얻었다.(1) 2-Bromo-3-hydroxypyridine (5.19 g), 1-Bromo-2-methylpropane (4.11 g) and Potassium carbonate (4.84 g) are dissolved in DMF and stirred at 80 ° C. After extraction with dichloromethane, an intermediate was obtained by column chromatography.
(2) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간 동안 교반하였다. 이 후, 상기 과정 (1)에서 얻은 중간체 4.2g을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻었다.(2) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 4.2 g of the intermediate obtained in the above step (1) is added, and the mixture is stirred under reflux. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(3) 상기 과정 (2)에서 얻은 전구체 리간드 1.58g을 dichloromethane(100mL)에 녹인 후, 여기에 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 10으로 표시되는 화합물을 얻었다.(3) 1.58 g of the precursor ligand obtained in the above step (2) was dissolved in dichloromethane (100 mL), and then triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (10).
[화학식 10][Chemical formula 10]
1H NMR (300 MHz, CDCl3) δ 1.14 (6H), 2.37 (1H), 3.87 (2H), 6.87 (1H), 6.98 (2H), 7.73 (1H), 7.85 (2H), 8.19 (1H)
1 H NMR (300 MHz, CDCl 3) δ 1.14 (6H), 2.37 (1H), 3.87 (2H), 6.87 (1H), 6.98 (2H), 7.73 (1H), 7.85 (2H), 8.19 (1H)
합성예Synthetic example 5: 화학식 11로 표시되는 화합물의 합성 5: Synthesis of Compound Represented by Formula 11
(1) 2-Bromo-3-hydroxypyridine(5.19g), 1-Bromo-4-methylpropane(5.02g), Potassium carbonate(4.84g)을 DMF에 녹이고, 80℃에서 교반한다. Dichloromethane으로 추출 후, 컬럼 크로마토그래피를 이용하여 중간체를 얻었다.(1) 2-Bromo-3-hydroxypyridine (5.19 g), 1-Bromo-4-methylpropane (5.02 g) and Potassium carbonate (4.84 g) are dissolved in DMF and stirred at 80 ° C. After extraction with dichloromethane, an intermediate was obtained by column chromatography.
(2) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간 동안 교반하였다. 이 후, 상기 과정 (1)에서 얻은 중간체 3.92g을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻었다.(2) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Thereafter, 3.92 g of the intermediate obtained in the above step (1) was added, and the mixture was stirred under reflux. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(3) 상기 과정 (2)에서 얻은 전구체 리간드 1.48g을 dichloromethane(100mL)에 녹인 후, 여기에 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 11로 표시되는 화합물을 얻었다.(3) 1.48 g of the precursor ligand obtained in the above step (2) was dissolved in dichloromethane (100 mL), and then triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (11).
[화학식 11](11)
GC-MS(DI) m/z: 343.17
GC-MS (DI) m / z: 343.17
합성예Synthetic example 6: 화학식 13으로 표시되는 화합물의 합성 6: Synthesis of Compound Represented by Formula 13
(1) 2-Chloro-5-(chloromethyl)pyridine(3.22g), 1,4-Dihydroxybenzene(2.20g), Potassium carbonate(3.04g)을 DMF에 녹이고, 80℃에서 교반한다. 반응종료 후, Dichloromethane으로 추출하여 중간체를 얻는다.(1) 2-Chloro-5- (chloromethyl) pyridine (3.22 g), 1,4-Dihydroxybenzene (2.20 g) and Potassium carbonate (3.04 g) are dissolved in DMF and stirred at 80 ° C. After completion of the reaction, the mixture is extracted with dichloromethane to obtain an intermediate.
(2) 상기 과정 (1)에서 얻은 중간체(3.53g), 1-Bromo-2-ethylhexane(3.84g), Potassium carbonate (2.3g)을 DMF에 녹이고, 80℃에서 교반한다. 반응종료 후, Dichloromethane으로 추출하여 중간체를 얻는다.(2) 3.53 g of the intermediate obtained in the above step (1), 1-bromo-2-ethylhexane (3.84 g) and potassium carbonate (2.3 g) are dissolved in DMF and stirred at 80 ° C. After completion of the reaction, the mixture is extracted with dichloromethane to obtain an intermediate.
(3)1,4-Dioxane (50mL)에 녹인 2-Pyridine acetonitrile(1.18g)에 Sodium hydride(1.2g)을 상온에서 천천히 가하고 30분 동안 교반하였다. 이 후, 상기 과정 (2)에서 얻은 중간체 3.48g을 천천히 넣고 환류 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻는다.(3) Sodium hydride (1.2 g) was slowly added to 2-pyridine acetonitrile (1.18 g) dissolved in 1,4-dioxane (50 mL) at room temperature and stirred for 30 minutes. Thereafter, 3.48 g of the intermediate obtained in the above step (2) was slowly added and stirred under reflux. After completion of the reaction, the reaction mixture is neutralized with an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(4) 상기 과정 (3)에서 얻은 전구체 리간드 2.15g을 dichloromethane(50mL)에 녹인 후, 여기에 상온에서 triethylamine(2.5mL), Borontrifluoride diethyl etherate(3.5mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 13으로 표시되는 화합물을 얻었다.(4) 2.15 g of the precursor ligand obtained in the above step (3) was dissolved in dichloromethane (50 mL), and then triethylamine (2.5 mL) and borontrifluoride diethyl etherate (3.5 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (13).
[화학식 13][Chemical Formula 13]
GC-MS(DI) m/z: 477.23
GC-MS (DI) m / z: 477.23
합성예Synthetic example 7: 화학식 14로 표시되는 화합물의 합성 7: Synthesis of Compound Represented by Formula 14
(1) 2-Chloro-5-(chloromethyl)pyridine(3.22g), Di(2-ethylhexyl)amine (4.90g), Potassium carbonate(3.04g)을 DMF에 녹이고, 80℃에서 교반한다.반응 종료 후 Dichloromethane으로 추출하여 중간체를 얻는다.(1) 2-Chloro-5- (chloromethyl) pyridine (3.22 g), Di (2-ethylhexyl) amine (4.90 g) and Potassium carbonate (3.04 g) were dissolved in DMF and stirred at 80 ° C. After completion of the reaction Extract with dichloromethane to obtain an intermediate.
(2) 1,4-Dioxane (100mL)에 녹인 2-Pyridine acetonitrile(1.18g)에 Sodium hydride(1.2g)을 상온에서 천천히 가하고 30분동안 교반하였다. 이 후, 상기과정 (1)에서 얻은 상기 중간체 3.33g을 천천히 넣고 환류 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻는다.(2) Sodium hydride (1.2 g) was slowly added to 2-pyridine acetonitrile (1.18 g) dissolved in 1,4-dioxane (100 mL) at room temperature and stirred for 30 minutes. Thereafter, 3.33 g of the intermediate obtained in the above step (1) was slowly added and stirred under reflux. After completion of the reaction, the reaction mixture is neutralized with an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(3)상기 과정 (2)에서 얻은 전구체 리간드 2.24g을 dichloromethane(50mL)에 녹인 후, 여기에 상온에서 triethylamine(2.5mL), Borontrifluoride diethyl etherate(3.5mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 하기 화학식 14로 표시되는 화합물을 얻었다.(3) 2.24 g of the precursor ligand obtained in the above step (2) was dissolved in dichloromethane (50 mL), and then triethylamine (2.5 mL) and borontrifluoride diethyl etherate (3.5 mL) were sequentially added thereto at room temperature and stirred. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (14).
[화학식 14][Chemical Formula 14]
1H NMR (300 MHz, CDCl3) δ 0.86(12H), 1.25 (16H), 1.43 (2H), 2.16(4H), 3.40(2H), 6.89(1H), 7.54(2H), 7.68(1H), 7.75(1H), 8.06(1H), 8.15(1H)
1 H NMR (300 MHz, CDCl 3) δ 0.86 (12H), 1.25 (16H), 1.43 (2H), 2.16 (4H), 3.40 (2H), 6.89 (1H), 7.54 (2H), 7.68 (1H) , 7.75 (1H), 8.06 (1H), 8.15 (1H)
합성예Synthetic example 8: 화학식 16으로 표시되는 화합물의 합성 8: Synthesis of the compound represented by the formula (16)
(1) THF(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간동안 교반하였다. 이 후, 2-Bromopyridine(2.55g)을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드(bis(2-pyridyl)acetonitrile)를 얻었다.(1) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in THF (100 mL) at room temperature and stirred for 1 hour. Then, 2-bromopyridine (2.55 g) is added and stirred under reflux. After completion of the reaction, the reaction mixture was neutralized with an acidic aqueous solution during extraction and separated by column chromatography to obtain bis (2-pyridyl) acetonitrile.
(2) 상기 과정 (1)에서 얻은 전구체 리간드(bis(2-pyridyl)acetonitrile) 0.98g을 dichloromethane(100mL)에 녹인 후, 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼크로마토그래피로 분리하여 전구체인 디피리도메탄계 이불화붕소 화합물을 얻었다.(2) 0.98 g of the bis (2-pyridyl) acetonitrile obtained in the above step (1) was dissolved in dichloromethane (100 mL), and then triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) Respectively. After completion of the reaction, the reaction product was separated by column chromatography to obtain a precursor, a dipyridomethane-based boronized boron compound.
(3) 상기 과정 (2)에서 얻은 전구체인 디피리도메탄계 붕소화합물(1.22g)을 dichloromethane 50mL에 녹인 후, 고체상의 Aluminum chloride(1.7g)을 가하고 5분 정도 교반한다. 이 후, Acetonitrile에 녹인 Catechol(1.1g)을 넣고 상온에서 교반하다. 반응종료 후, 컬럼 크로마토그래피로 분리하여 하기 화학식 16으로 표시되는 화합물을 얻었다.(3) Dipyridomethane boron compound (1.22 g) which is the precursor obtained in the above process (2) is dissolved in 50 mL of dichloromethane, and then solid aluminum chloride (1.7 g) is added and stirred for 5 minutes. After that, catechol (1.1 g) dissolved in acetonitrile is added and stirred at room temperature. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (16).
[화학식 16][Chemical Formula 16]
1H NMR (300 MHz, CDCl3) δ 6.85(6H), 7.59 (2H), 7.69 (2H), 7.87 (2H)
1 H NMR (300 MHz, CDCl 3 ) ? 6.85 (6H), 7.59 (2H), 7.69
합성예Synthetic example 9: 화학식 17로 표시되는 화합물의 합성 9: Synthesis of Compound Represented by Chemical Formula 17
상기 합성예 8의 합성과정 (2)에서 얻은 붕소화합물(1.22g)을 dichloromethane 50mL에 녹인 후, 고체상의 Aluminum chloride(1.7g)을 가하고 5분 정도 교반한다. 이 후, Acetonitrile에 녹인 4-tert-Butylpyrocatechol(1.67g)을 넣고 상온에서 교반하다. 반응종료 후, 컬럼 크로마토그래피로 분리하여 하기 화학식 17로 표시되는 화합물을 얻었다.The boron compound (1.22 g) obtained in the synthesis process (2) of Synthesis Example 8 was dissolved in 50 mL of dichloromethane, and then solid aluminum chloride (1.7 g) was added and stirred for 5 minutes. After that, 4- tert- butylpyrocatechol (1.67 g) dissolved in acetonitrile is added and stirred at room temperature. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following general formula (17).
[화학식 17][Chemical Formula 17]
GC-MS(DI) m/z: 369.16
GC-MS (DI) m / z: 369.16
합성예Synthetic example 10: 화학식 18로 표시되는 화합물의 합성 10: Synthesis of Compound Represented by Formula 18
상기 합성예 4의 합성과정 (3)에서 얻은 붕소화합물(1.22g)을 dichloromethane 50mL에 녹인 후, 고체상의 Aluminum chloride(1.7g)을 가하고 5분 정도 교반한다. 이 후, Acetonitrile에 녹인 4-tert-Butylpyrocatechol(1.67g)을 넣고 상온에서 교반하다. 반응종료 후, 컬럼 크로마토그래피로 분리하여 하기 화학식 18로 표시되는 화합물을 얻었다.The boron compound (1.22 g) obtained in the synthesis step (3) of Synthesis Example 4 was dissolved in 50 mL of dichloromethane, and then solid aluminum chloride (1.7 g) was added and stirred for 5 minutes. After that, 4- tert- butylpyrocatechol (1.67 g) dissolved in acetonitrile is added and stirred at room temperature. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (18).
[화학식 18][Chemical Formula 18]
1H NMR (300 MHz, CDCl3) δ 1.15(6H), 2.38(1H), 3.87(1H), 6.76(1H), 6.85(5H), 6.99(1H), 7.57 (1H), 7.70(1H), 7.85(1H), 7.93 (1H)
1 H NMR (300 MHz, CDCl 3) δ 1.15 (6H), 2.38 (1H), 3.87 (1H), 6.76 (1H), 6.85 (5H), 6.99 (1H), 7.57 (1H), 7.70 (1H) , 7.85 (1H), 7.93 (1H)
합성예Synthetic example 11: 화학식 19로 표시되는 화합물의 합성 11: Synthesis of Compound Represented by Formula 19
상기 합성예 1의 합성과정 (2)에서 얻은 붕소화합물(1.22g)을 dichloromethane 50mL에 녹인 후, 고체상의 Aluminum chloride(1.7g)을 가하고 5분 정도 교반한다. 이 후, Acetonitrile에 녹인 4-tert-Butylpyrocatechol(1.67g)을 넣고 상온에서 교반하다. 반응종료 후, 컬럼 크로마토그래피로 분리하여 하기 화학식 19로 표시되는 화합물을 얻었다.After dissolving the boron compound (1.22 g) obtained in the synthesis step (2) of Synthesis Example 1 in 50 mL of dichloromethane, solid aluminum chloride (1.7 g) was added and stirred for 5 minutes. After that, 4- tert- butylpyrocatechol (1.67 g) dissolved in acetonitrile is added and stirred at room temperature. After completion of the reaction, the reaction mixture was separated by column chromatography to obtain a compound represented by the following formula (19).
[화학식 19][Chemical Formula 19]
GC-MS(DI) m/z: 441.34
GC-MS (DI) m / z: 441.34
합성예Synthetic example 12: 화학식 15로 표시되는 화합물의 합성 12: Synthesis of compound represented by formula (15)
(1) 1,4-Dioxane(100mL)에 녹인 2-Pyridine acetonitrile(1.9g)에 Sodium hydride(2.24g)을 상온에서 천천히 가하고 1시간 동안 교반하였다. 이 후, 2-Chloro-5-(chloromethyl)pyridine (1.00g)을 넣고 환류하면서 교반한다. 반응 종료 후 추출과정에서 산성수용액을 이용하여 중화시키고, 컬럼 크로마토그래피로 분리하여 전구체 리간드를 얻었다.(1) Sodium hydride (2.24 g) was slowly added to 2-pyridine acetonitrile (1.9 g) dissolved in 1,4-dioxane (100 mL) at room temperature and stirred for 1 hour. Thereafter, 2-Chloro-5- (chloromethyl) pyridine (1.00 g) is added and stirred under reflux. After completion of the reaction, the reaction mixture was neutralized using an acidic aqueous solution during extraction and separated by column chromatography to obtain a precursor ligand.
(2) 상기 과정 (1)에서 얻은 전구체 리간드 1.63g을 dichloromethane(100mL)에 녹인 후, 상온에서 triethylamine(3mL), Borontrifluoride diethyl etherate(4mL)를 순서대로 넣고 교반하였다. 반응 종료 후 컬럼 크로마토그래피로 분리하여 전구체인 디피리도메탄계 이불화붕소 화합물을 얻었다.(2) 1.63 g of the precursor ligand obtained in the above step (1) was dissolved in dichloromethane (100 mL), and triethylamine (3 mL) and borontrifluoride diethyl etherate (4 mL) were sequentially added at room temperature and stirred. After completion of the reaction, the reaction product was separated by column chromatography to obtain a precursor, a dipyridomethane-based boronized boron compound.
[화학식 15][Chemical Formula 15]
1H NMR (300 MHz, CDCl3) δ 3.36(2H), 4.26 (1H), 6.93 (1H), 7.33 (2H), 7.51(3H), 7.72 (2H), 7.85(1H), 8.14(1H), 8.66 (1H)
1 H NMR (300 MHz, CDCl 3) δ 3.36 (2H), 4.26 (1H), 6.93 (1H), 7.33 (2H), 7.51 (3H), 7.72 (2H), 7.85 (1H), 8.14 (1H) , 8.66 (1H)
비교 compare 합성예Synthetic example 1 One
환류 냉각기와 교반기를 장착한 10ℓ의 중합 반응기에 사이클로헥사논(Shiny社) 1000g을 80℃로 가열한 후, 위에서 제조된 화합물(12) 300g, 벤질 메타크릴레이트(Hitach社) 300g, 메타크릴산(대정화금製) 106g 및 2,2'-아조비스아이소부티로니트릴(wako社) 92g을 사이클로헥사논(Shiny社) 5000g에 녹인 용액을 가열된 중합 반응기에 3시간 동안 서서히 투입하였다. 투입 완료 후 14시간 동안 교반하여 하기 화학식 20으로 표시되는 반복단위를 포함하는 폴리머를 얻었다. Waters社의 겔투과 크로마토그래피(Gel Permission Chromatography: GPC)를 이용하여 측정한 중량평균분자량은 9,800 g/mol 이었다. 1000 g of cyclohexanone (Shiny) was heated to 80 占 폚, and then 300 g of the compound (12) prepared above, 300 g of benzyl methacrylate (Hitach), 300 g of methacrylic acid (Manufactured by Daikin Industries, Ltd.) and 92 g of 2,2'-azobisisobutyronitrile (wako) in 5000 g of cyclohexanone (Shiny) was slowly added to the heated polymerization reactor for 3 hours. After completion of the addition, the mixture was stirred for 14 hours to obtain a polymer containing a repeating unit represented by the following formula (20). The weight average molecular weight measured by Gel Permeation Chromatography (GPC) of Waters was 9,800 g / mol.
[화학식 20][Chemical Formula 20]
(상기 화학식 20에서, a=2, b=2 및 c=1 이다.)
(In the above formula (20), a = 2, b = 2, and c = 1.)
(감광성 수지 조성물의 합성)(Synthesis of photosensitive resin composition)
실시예Example 1 One
하기 언급된 구성성분들을 하기 표 1에 나타낸 조성으로 혼합하여 실시예 1에 따른 감광성 수지 조성물을 제조하였다.The photosensitive resin composition according to Example 1 was prepared by mixing the following components in the compositions shown in Table 1 below.
구체적으로, 용매에 광중합 개시제를 녹인 후 2 시간 동안 상온에서 교반한 다음, 여기에 알칼리 가용성 수지 및 광중합성 화합물을 첨가하여 2시간 동안 상온에서 교반하였다. 이어서, 얻어진 상기 반응물에 착색제로서 상기 합성예 1에서 제조된 화합물(화학식 3-1로 표시되는 화합물) 및 안료(안료분산액 형태)를 넣고 1 시간 동안 상온에서 교반하였다. 이어 상기 생성물을 3회 여과하여 불순물을 제거함으로써, 감광성 수지 조성물을 제조하였다.
Specifically, a photopolymerization initiator was dissolved in a solvent, and the mixture was stirred at room temperature for 2 hours. Then, an alkali-soluble resin and a photopolymerizable compound were added thereto, followed by stirring at room temperature for 2 hours. Then, the obtained reaction product was added with the compound (the compound represented by Formula 3-1) and the pigment (in the form of pigment dispersion) prepared in Synthesis Example 1 as a colorant and stirred at room temperature for 1 hour. Then, the product was filtered three times to remove impurities, thereby preparing a photosensitive resin composition.
분자량(Mw)=22,000g/mol
(A): 메타크릴산
(B): 벤질메타크릴레이트(A) / (B) = 15/85 (w / w),
Molecular weight (Mw) = 22,000 g / mol
(A): methacrylic acid
(B): benzyl methacrylate
실시예Example 2 2
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 2의 화합물(화학식 8로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 2 (the compound of Formula 8) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 3 3
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 3의 화합물(화학식 9로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 3 (the compound of Formula 9) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 4 4
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 4의 화합물(화학식 10으로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 4 (the compound of Formula 10) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예 5Example 5
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 5의 화합물(화학식 11로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 5 (the compound of Formula 11) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 6 6
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 6의 화합물(화학식 13으로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 6 (the compound of Formula 13) was used instead of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 7 7
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 7의 화합물(화학식 14로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 7 (the compound of Formula 14) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 8 8
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 8의 화합물(화학식 16으로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 8 (the compound of Formula 16) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 9 9
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 9의 화합물(화학식 17로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1 except that the compound of Synthesis Example 9 (the compound of Formula 17) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 10 10
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 10의 화합물(화학식 18로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 10 (the compound of Formula 18) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 11 11
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 11의 화합물(화학식 19로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 11 (the compound of Formula 19) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
실시예Example 12 12
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 합성예 12의 화합물(화학식 15로 표시되는 화합물)을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Synthesis Example 12 (the compound of Formula 15) was used in place of the compound of Synthesis Example 1 (the compound of Formula 12).
비교예Comparative Example 1 One
합성예 1의 화합물(화학식 12로 표시되는 화합물) 대신 비교 합성예 1(화학식 20으로 표시되는 화합물)의 화합물을 사용한 것을 제외하고는 실시예 1과 동일하게 하여, 감광성 수지 조성물을 제조하였다.
A photosensitive resin composition was prepared in the same manner as in Example 1, except that the compound of Comparative Synthesis Example 1 (the compound represented by the general formula (20)) was used instead of the compound of Synthesis Example 1 (the compound represented by the general formula (12)).
평가: evaluation: 색좌표Color coordinates , 휘도, 및 명암비 측정, Luminance, and contrast ratio
탈지 세척한 두께 1 mm의 유리 기판 상에 1 ㎛ 내지 3 ㎛의 두께로 상기 실시예 1 내지 실시예 12 및 비교예 1에서 제조한 감광성 수지 조성물을 도포하고, 90℃의 핫 플레이트 상에서 2분 동안 건조시켜 도막을 수득하였다. 계속해서 도막에 365nm의 주파장을 가진 고압수은램프를 사용하여 노광하여 수득하였다. 200℃의 열풍순환식 건조로 안에서 5분 동안 건조시켜 수득하였다. 화소층은 분광광도계(MCPD3000, Otsuka electronic社)를 이용하여 색좌표(x, y), 휘도(Y) 및 명암비를 측정하여, 하기 표 2에 기재하였다.
The photosensitive resin composition prepared in Examples 1 to 12 and Comparative Example 1 was applied on a 1 mm thick glass substrate having a thickness of 1 to 3 占 퐉 and washed on a hot plate at 90 占 폚 for 2 minutes And dried to obtain a coating film. Subsequently, a coating film was obtained by exposure using a high-pressure mercury lamp having a dominant wavelength of 365 nm. And dried in a hot air circulating drying oven at 200 ° C for 5 minutes. The color layer (x, y), luminance (Y), and contrast ratio were measured using a spectrophotometer (MCPD3000, Otsuka electronic Co.)
상기 표 2로부터, 일 구현예에 따른 화합물을 염료로 포함하는 실시예 1 내지 실시예 12의 감광성 수지 조성물이 상기 화합물을 포함하지 않은 비교예 1의 감광성 수지 조성물보다 우수한 색특성을 나타냄을 확인할 수 있다.
From Table 2, it can be seen that the photosensitive resin compositions of Examples 1 to 12 containing the compound according to one embodiment as a dye exhibited color characteristics superior to those of the photosensitive resin composition of Comparative Example 1, have.
이상 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고, 특허청구범위와 발명의 상세한 설명 및 첨부한 도면의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고, 이 또한 본 발명의 범위에 속하는 것은 당연하다.While the present invention has been particularly shown and described with reference to exemplary embodiments thereof, it is to be understood that the invention is not limited to the disclosed exemplary embodiments, but, on the contrary, And it goes without saying that the invention belongs to the scope of the invention.
Claims (13)
[화학식 1]
상기 화학식 1에서,
R1 내지 R8은 각각 독립적으로 수소 원자, 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C1 내지 C20 알콕시기 또는 치환 또는 비치환된 C6 내지 C20 헤테로아릴기이고,
M은 하기 화학식 3으로 표시되고,
[화학식 3]
상기 화학식 3에서,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.
(상기에서 "치환" 내지 "치환된"이란, 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 알킬기, 알케닐기, 알키닐기, 지환족 유기기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다)
A compound represented by the following formula (1):
[Chemical Formula 1]
In Formula 1,
R 1 to R 8 are each independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C1 to C20 alkoxy group or a substituted or unsubstituted C6 to C20 heteroaryl group,
M is represented by the following formula (3)
(3)
In Formula 3,
A is a substituted or unsubstituted C6 to C20 aryl group.
(Wherein the "substituted" to "substituted" means one or more hydrogen atom is a halogen atom in the functional group (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH 2, NH (R 200) or N (R 201 ) (R 202 ), wherein R 200 , R 201 and R 202 are the same or different and are each independently a C 1 to C 10 alkyl group), an amidino group, a hydrazine group, Substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alicyclic organic group, an aryl group and a heterocyclic group)
상기 R1 내지 R4는 모두 수소 원자이고,
상기 R5 내지 R8는 각각 독립적으로 수소 원자,치환 또는 비치환된 C1 내지 C20 알킬기 또는 치환 또는 비치환된 C1 내지 C20 알콕시기인 화합물.
(상기에서 "치환" 내지 "치환된"이란, 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 알킬기, 알케닐기, 알키닐기, 지환족 유기기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다)
The method according to claim 1,
Wherein each of R 1 to R 4 is a hydrogen atom,
Each of R 5 to R 8 is independently a hydrogen atom, a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C1 to C20 alkoxy group.
(Wherein the "substituted" to "substituted" means one or more hydrogen atom is a halogen atom in the functional group (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH 2, NH (R 200) or N (R 201 ) (R 202 ), wherein R 200 , R 201 and R 202 are the same or different and are each independently a C 1 to C 10 alkyl group), an amidino group, a hydrazine group, Substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alicyclic organic group, an aryl group and a heterocyclic group)
상기 R1 내지 R4는 모두 수소 원자이고,
상기 R6은 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알킬기이고,
상기 R8은 수소 원자 또는 치환 또는 비치환된 C1 내지 C20 알콕시기인 화합물.
(상기에서 "치환" 내지 "치환된"이란, 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 알킬기, 알케닐기, 알키닐기, 지환족 유기기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다)
The method according to claim 1,
Wherein each of R 1 to R 4 is a hydrogen atom,
R 6 is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
Wherein R < 8 > is a hydrogen atom or a substituted or unsubstituted C1 to C20 alkoxy group.
(Wherein the "substituted" to "substituted" means one or more hydrogen atom is a halogen atom in the functional group (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH 2, NH (R 200) or N (R 201 ) (R 202 ), wherein R 200 , R 201 and R 202 are the same or different and are each independently a C 1 to C 10 alkyl group), an amidino group, a hydrazine group, Substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alicyclic organic group, an aryl group and a heterocyclic group)
상기 화학식 1은 하기 화학식 4 내지 화학식 7 중 어느 하나로 표시되는 화합물:
[화학식 4]
[화학식 5]
[화학식 6]
[화학식 7]
상기 화학식 4 내지 화학식 7에서,
X1은 N, P 또는 B이고,
X2 및 X3는 각각 독립적으로, O, S, S(=O) 또는 S(=O)2이고,
L1은 치환 또는 비치환된 C1 내지 C20 알킬렌기이고,
L2는 치환 또는 비치환된 C1 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,
R9 및 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 헤테로아릴기 또는 시아노기이고,
M은 하기 화학식 3으로 표시되고,
[화학식 3]
상기 화학식 3에서,
A는 치환 또는 비치환된 C6 내지 C20 아릴기이다.
(상기에서 "치환" 내지 "치환된"이란, 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 알킬기, 알케닐기, 알키닐기, 지환족 유기기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다)
The method according to claim 1,
(1) is a compound represented by any one of the following formulas (4) to (7)
[Chemical Formula 4]
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above Chemical Formulas 4 to 7,
X < 1 > is N, P or B,
X 2 and X 3 are each independently O, S, S (= O) or S (= O) 2 ,
L 1 is a substituted or unsubstituted C1 to C20 alkylene group,
L 2 is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R 9 and R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a cyano group,
M is represented by the following formula (3)
(3)
In Formula 3,
A is a substituted or unsubstituted C6 to C20 aryl group.
(Wherein the "substituted" to "substituted" means one or more hydrogen atom is a halogen atom in the functional group (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH 2, NH (R 200) or N (R 201 ) (R 202 ), wherein R 200 , R 201 and R 202 are the same or different and are each independently a C 1 to C 10 alkyl group), an amidino group, a hydrazine group, Substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alicyclic organic group, an aryl group and a heterocyclic group)
상기 화학식 1은 하기 화학식 16 내지 화학식 19로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물.
[화학식 16]
[화학식 17]
[화학식 18]
[화학식 19]
The method according to claim 1,
The compound represented by Formula 1 is represented by any one selected from the group consisting of the following Formulas 16 to 19:
[Chemical Formula 16]
[Chemical Formula 17]
[Chemical Formula 18]
[Chemical Formula 19]
[화학식 5]
[화학식 6]
[화학식 7]
상기 화학식 5 내지 화학식 7에서,
X1은 N, P 또는 B이고,
X2 및 X3는 각각 독립적으로, O, S, S(=O) 또는 S(=O)2이고,
L1은 치환 또는 비치환된 C1 내지 C20 알킬렌기이고,
L2는 치환 또는 비치환된 C1 내지 C20 알킬렌기 또는 치환 또는 비치환된 C6 내지 C20 아릴렌기이고,
R9 및 R12는 각각 독립적으로 치환 또는 비치환된 C1 내지 C20 알킬기, 치환 또는 비치환된 C2 내지 C20 헤테로아릴기 또는 시아노기이고,
M은 하기 화학식 2로 표시된다.
[화학식 2]
(상기에서 "치환" 내지 "치환된"이란, 작용기 중의 하나 이상의 수소 원자가 할로겐 원자(F, Br, Cl 또는 I), 히드록시기, 니트로기, 시아노기, 아미노기(NH2, NH(R200) 또는 N(R201)(R202)이고, 여기서 R200, R201 및 R202는 동일하거나 서로 상이하며, 각각 독립적으로 C1 내지 C10 알킬기임), 아미디노기, 하이드라진기, 하이드라존기, 카르복실기, 알킬기, 알케닐기, 알키닐기, 지환족 유기기, 아릴기 및 헤테로고리기로 이루어진 군에서 선택되는 1종 이상의 치환기로 치환된 것을 의미한다)
A compound represented by any one of the following formulas (5) to (7):
[Chemical Formula 5]
[Chemical Formula 6]
(7)
In the above Chemical Formulas 5 to 7,
X < 1 > is N, P or B,
X 2 and X 3 are each independently O, S, S (= O) or S (= O) 2 ,
L 1 is a substituted or unsubstituted C1 to C20 alkylene group,
L 2 is a substituted or unsubstituted C1 to C20 alkylene group or a substituted or unsubstituted C6 to C20 arylene group,
R 9 and R 12 are each independently a substituted or unsubstituted C1 to C20 alkyl group, a substituted or unsubstituted C2 to C20 heteroaryl group or a cyano group,
M is represented by the following formula (2).
(2)
(Wherein the "substituted" to "substituted" means one or more hydrogen atom is a halogen atom in the functional group (F, Br, Cl or I), a hydroxy group, a nitro group, a cyano group, an amino group (NH 2, NH (R 200) or N (R 201 ) (R 202 ), wherein R 200 , R 201 and R 202 are the same or different and are each independently a C 1 to C 10 alkyl group), an amidino group, a hydrazine group, Substituted with at least one substituent selected from the group consisting of an alkyl group, an alkenyl group, an alkynyl group, an alicyclic organic group, an aryl group and a heterocyclic group)
상기 화합물은 하기 화학식 8 내지 화학식 15로 이루어진 군에서 선택된 어느 하나로 표시되는 화합물.
[화학식 8]
[화학식 9]
[화학식 10]
[화학식 11]
[화학식 12]
[화학식 13]
[화학식 14]
[화학식 15]
8. The method of claim 7,
Wherein said compound is represented by any one of the following formulas (8) to (15).
[Chemical Formula 8]
[Chemical Formula 9]
[Chemical formula 10]
(11)
[Chemical Formula 12]
[Chemical Formula 13]
[Chemical Formula 14]
[Chemical Formula 15]
상기 화합물은 황색 염료인 화합물.
8. The method of claim 1 or 7,
Wherein said compound is a yellow dye.
상기 황색 염료는 400nm 내지 550nm의 파장범위에서 최대 흡광영역을 가지는 화합물.
10. The method of claim 9,
Wherein the yellow dye has a maximum light absorption region in a wavelength range of 400 nm to 550 nm.
8. A photosensitive resin composition comprising the compound of any one of claims 1 to 7.
상기 감광성 수지 조성물은 안료, 알칼리 가용성 수지, 광중합성 화합물, 광중합 개시제 및 용매를 더 포함하는 감광성 수지 조성물.
12. The method of claim 11,
The photosensitive resin composition further comprises a pigment, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and a solvent.
A color filter produced by using the photosensitive resin composition of claim 11.
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|---|---|---|---|---|
| JP2003307611A (en) * | 2002-04-17 | 2003-10-31 | Fujifilm Arch Co Ltd | Color filter and method for manufacturing the same |
Non-Patent Citations (1)
| Title |
|---|
| Organic Letters, Vol.44, pp. 4010-4013, 2010* |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2016085075A1 (en) | 2016-06-02 |
| KR20160064877A (en) | 2016-06-08 |
| TWI589582B (en) | 2017-07-01 |
| TW201619169A (en) | 2016-06-01 |
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