CN111880373A - Photosensitive resin composition, photosensitive resin layer and color filter - Google Patents
Photosensitive resin composition, photosensitive resin layer and color filter Download PDFInfo
- Publication number
- CN111880373A CN111880373A CN202010357498.2A CN202010357498A CN111880373A CN 111880373 A CN111880373 A CN 111880373A CN 202010357498 A CN202010357498 A CN 202010357498A CN 111880373 A CN111880373 A CN 111880373A
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- CN
- China
- Prior art keywords
- photosensitive resin
- chemical formula
- resin composition
- unsubstituted
- substituted
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 239000011342 resin composition Substances 0.000 title claims abstract description 69
- 229920005989 resin Polymers 0.000 title claims abstract description 36
- 239000011347 resin Substances 0.000 title claims abstract description 36
- 239000000126 substance Substances 0.000 claims abstract description 272
- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- 239000011258 core-shell material Substances 0.000 claims abstract description 59
- 239000002904 solvent Substances 0.000 claims abstract description 27
- 239000003086 colorant Substances 0.000 claims abstract description 23
- 239000011230 binding agent Substances 0.000 claims abstract description 17
- 239000003999 initiator Substances 0.000 claims abstract description 15
- 239000000975 dye Substances 0.000 claims description 74
- 239000000049 pigment Substances 0.000 claims description 33
- -1 acryloyloxy Chemical group 0.000 claims description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 6
- 239000001046 green dye Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- KQIGMPWTAHJUMN-UHFFFAOYSA-N 3-aminopropane-1,2-diol Chemical compound NCC(O)CO KQIGMPWTAHJUMN-UHFFFAOYSA-N 0.000 claims description 3
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000007822 coupling agent Substances 0.000 claims description 3
- 239000007870 radical polymerization initiator Substances 0.000 claims description 3
- 229910000077 silane Inorganic materials 0.000 claims description 3
- 239000004094 surface-active agent Substances 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 76
- 238000003786 synthesis reaction Methods 0.000 description 76
- 238000002360 preparation method Methods 0.000 description 50
- 238000000034 method Methods 0.000 description 42
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 33
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 24
- 239000000178 monomer Substances 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 239000010410 layer Substances 0.000 description 13
- 239000006185 dispersion Substances 0.000 description 11
- 239000000758 substrate Substances 0.000 description 10
- 239000004593 Epoxy Substances 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000001055 blue pigment Substances 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 239000001054 red pigment Substances 0.000 description 9
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 7
- 241000011547 Plebejus idas Species 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 239000001056 green pigment Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 238000000576 coating method Methods 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 239000001052 yellow pigment Substances 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000010408 film Substances 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WHNBDXQTMPYBAT-UHFFFAOYSA-N 2-butyloxirane Chemical compound CCCCC1CO1 WHNBDXQTMPYBAT-UHFFFAOYSA-N 0.000 description 3
- LPEKGGXMPWTOCB-UHFFFAOYSA-N 8beta-(2,3-epoxy-2-methylbutyryloxy)-14-acetoxytithifolin Natural products COC(=O)C(C)O LPEKGGXMPWTOCB-UHFFFAOYSA-N 0.000 description 3
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-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
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 3
- 229960002130 benzoin Drugs 0.000 description 3
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 239000011247 coating layer Substances 0.000 description 3
- 235000019382 gum benzoic Nutrition 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 150000002678 macrocyclic compounds Chemical class 0.000 description 3
- 239000011159 matrix material Substances 0.000 description 3
- 229910044991 metal oxide Inorganic materials 0.000 description 3
- 150000004706 metal oxides Chemical class 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229960004063 propylene glycol Drugs 0.000 description 3
- GWHOGODUVLQCEB-UHFFFAOYSA-N pyridine-2,6-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC(C(Cl)=O)=N1 GWHOGODUVLQCEB-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 230000003595 spectral effect Effects 0.000 description 3
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-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
- BWYYRZBQXLCZJL-UHFFFAOYSA-N 2,4-dimethyl-n-phenylaniline Chemical compound CC1=CC(C)=CC=C1NC1=CC=CC=C1 BWYYRZBQXLCZJL-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 2
- HXDLWJWIAHWIKI-UHFFFAOYSA-N 2-hydroxyethyl acetate Chemical compound CC(=O)OCCO HXDLWJWIAHWIKI-UHFFFAOYSA-N 0.000 description 2
- SFAMKDPMPDEXGH-UHFFFAOYSA-N 2-hydroxyethyl propanoate Chemical compound CCC(=O)OCCO SFAMKDPMPDEXGH-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
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- ATHHXGZTWNVVOU-UHFFFAOYSA-N N-methylformamide Chemical compound CNC=O ATHHXGZTWNVVOU-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 241000448053 Toya Species 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000004840 adhesive resin Substances 0.000 description 2
- 229920006223 adhesive resin Polymers 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
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- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- CATSNJVOTSVZJV-UHFFFAOYSA-N heptan-2-one Chemical compound CCCCCC(C)=O CATSNJVOTSVZJV-UHFFFAOYSA-N 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000003384 imaging method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
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- 150000002923 oximes Chemical class 0.000 description 2
- 239000004065 semiconductor Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- STGNLGBPLOVYMA-MAZDBSFSSA-N (E)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.OC(=O)\C=C\C(O)=O STGNLGBPLOVYMA-MAZDBSFSSA-N 0.000 description 1
- STGNLGBPLOVYMA-TZKOHIRVSA-N (z)-but-2-enedioic acid Chemical compound OC(=O)\C=C/C(O)=O.OC(=O)\C=C/C(O)=O STGNLGBPLOVYMA-TZKOHIRVSA-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
- RBACIKXCRWGCBB-UHFFFAOYSA-N 1,2-Epoxybutane Chemical compound CCC1CO1 RBACIKXCRWGCBB-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
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- IMDHDEPPVWETOI-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2,2-trichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)(Cl)Cl)C=C1 IMDHDEPPVWETOI-UHFFFAOYSA-N 0.000 description 1
- VMCRQYHCDSXNLW-UHFFFAOYSA-N 1-(4-tert-butylphenyl)-2,2-dichloroethanone Chemical compound CC(C)(C)C1=CC=C(C(=O)C(Cl)Cl)C=C1 VMCRQYHCDSXNLW-UHFFFAOYSA-N 0.000 description 1
- ZBTMRBYMKUEVEU-UHFFFAOYSA-N 1-bromo-4-methylbenzene Chemical compound CC1=CC=C(Br)C=C1 ZBTMRBYMKUEVEU-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- RRQYJINTUHWNHW-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxyethoxy)ethane Chemical compound CCOCCOCCOCC RRQYJINTUHWNHW-UHFFFAOYSA-N 0.000 description 1
- CNJRPYFBORAQAU-UHFFFAOYSA-N 1-ethoxy-2-(2-methoxyethoxy)ethane Chemical compound CCOCCOCCOC CNJRPYFBORAQAU-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-UHFFFAOYSA-N 0.000 description 1
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 1
- ZAOMUMJENGCKAR-UHFFFAOYSA-N 2-(1-phenylbut-3-en-2-yloxy)but-3-enylbenzene Chemical compound C=1C=CC=CC=1CC(C=C)OC(C=C)CC1=CC=CC=C1 ZAOMUMJENGCKAR-UHFFFAOYSA-N 0.000 description 1
- AZUHIVLOSAPWDM-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-1h-imidazole Chemical compound C1=CNC(C=2NC=CN=2)=N1 AZUHIVLOSAPWDM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- DQMOHZLFVGYNAN-UHFFFAOYSA-N 2-(2-phenylethenyl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound ClC(Cl)(Cl)C1=NC(C(Cl)(Cl)Cl)=NC(C=CC=2C=CC=CC=2)=N1 DQMOHZLFVGYNAN-UHFFFAOYSA-N 0.000 description 1
- FVNIIPIYHHEXQA-UHFFFAOYSA-N 2-(4-methoxynaphthalen-1-yl)-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C12=CC=CC=C2C(OC)=CC=C1C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 FVNIIPIYHHEXQA-UHFFFAOYSA-N 0.000 description 1
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- 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
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
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- 125000004591 piperonyl group Chemical group C(C1=CC=2OCOC2C=C1)* 0.000 description 1
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- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 description 1
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Images
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
- G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K9/00—Use of pretreated ingredients
- C08K9/04—Ingredients treated with organic substances
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/007—Squaraine dyes
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- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
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- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
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- 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
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
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- 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
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- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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- G—PHYSICS
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- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- G—PHYSICS
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- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
Abstract
The application provides a photosensitive resin composition, a photosensitive resin layer manufactured by using the photosensitive resin composition and a color filter comprising the photosensitive resin layer, wherein the photosensitive resin composition comprises: (A) a colorant comprising a core-shell structured dye; (B) a binder resin; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the core is an arylcyanine-based compound and the shell is represented by chemical formula 1. In chemical formula 1Each substituent is as defined in the specification. The present application can improve the durability of a color filter and have high brightness and high contrast ratio. [ chemical formula 1]
Description
CROSS-REFERENCE TO RELATED APPLICATIONS
The present application claims priority and benefit of korean patent application No. 10-2019-0051681 filed by the korean intellectual property office at 5/02/2019, which is incorporated herein by reference in its entirety.
Technical Field
The present disclosure relates to a photosensitive resin composition, a photosensitive resin layer using the photosensitive resin composition, and a color filter including the photosensitive resin layer.
Background
Among many types of displays, liquid crystal displays have advantages in brightness, thinness, low cost, low operating power consumption, and improved adhesion to integrated circuits, and have been more widely used for laptop computers, monitors, and TV screens. The liquid crystal display device includes: a lower substrate on which a black matrix, a color filter, and an ITO pixel electrode are formed; and an upper substrate on which an active circuit portion including a liquid crystal layer, a thin film transistor, and a capacitor layer and an ITO pixel electrode are formed. The color filter is formed in the pixel region by sequentially stacking a plurality of pixel portions, which are generally formed of three primary colors such as red (R), green (G), and blue (B) in a predetermined order, to form each pixel, and the black matrix layer is disposed in a predetermined pattern on the transparent substrate to form a boundary between the pixels.
The pigment dispersion method is one of methods of forming a color filter, and provides a colored thin film by repeating a series of processes such as: the method includes coating a photopolymerizable composition including a colorant on a transparent substrate including a black matrix, exposing the formed pattern, removing a non-exposed portion with a solvent, and thermally curing the same. The colored photosensitive resin composition for manufacturing a color filter according to the pigment dispersion method generally includes an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, an epoxy resin, a solvent, other additives, and the like. The pigment dispersion method is actively applied to manufacture LCDs such as mobile phones, laptop computers, monitors, and TVs. However, photosensitive resin compositions for color filters used in pigment dispersion methods have recently been required to have improved performance and excellent pattern characteristics. In particular, high color reproducibility and high brightness as well as high contrast ratio characteristics are urgently required.
The image sensor is a component for photographing in a cellular phone camera or a Digital Still Camera (DSC). Image sensors may be classified into charge-coupled device (CCD) image sensors and Complementary Metal Oxide Semiconductor (CMOS) image sensors depending on manufacturing processes and application methods. Color imaging devices for charge coupled device image sensors or complementary metal oxide semiconductor image sensors include color filters each having filter segments mixing primary colors of red, green, and blue, and the colors are separated. The most recent color filters installed in color imaging devices have a pattern size of 2 micrometers or less than 2 micrometers, which is 1/100 to 1/200 of the pattern size of conventional color filter patterns for LCDs. Therefore, increased resolution and reduced pattern residue are important factors in determining device performance.
A color filter manufactured by using the pigment-type photosensitive resin composition has limitations in brightness and contrast ratio due to the size of pigment particles. In addition, a color image forming apparatus for an image sensor requires a small dispersion particle diameter for forming a fine pattern. In order to meet the demand, efforts have been made to obtain a color filter having improved brightness and contrast ratio by introducing a dye that does not form particles instead of a pigment, thereby preparing a photosensitive resin composition suitable for the dye. However, the dye has poor durability to the pigment, such as light resistance and heat resistance, and the like, and thus the brightness may be reduced.
Disclosure of Invention
The embodiment provides a photosensitive resin composition having improved brightness and durability.
Another embodiment provides a photosensitive resin layer manufactured using the photosensitive resin composition.
Another embodiment provides a color filter comprising a photosensitive resin layer.
Embodiments provide a photosensitive resin composition, comprising: (A) a colorant comprising a core-shell structured dye; (B) a binder resin; (C) a photopolymerizable compound (photopolymerizable monomer); (D) a photopolymerization initiator; and (E) a solvent, wherein the core is an arylcyanine-based compound and the shell is represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, which is a bonding position),
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom,
m is an integer of 1 to 10,
n is an integer of 0 to 3, and
L1and L2Independently a single bond or a substituted or unsubstituted C1 to C10 alkylene.
The shell may be represented by chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, which is a bonding position),
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom, and
n is an integer of 0 to 3.
The shell may be represented by one of chemical formulas 2-1 to 2-3.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
In chemical formulas 2-1 to 2-3,
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, and
R7and R8Independently a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, which is a bonding position).
The shell may have a cage width of 6.5 angstroms to 7.5 angstroms.
The shell may be represented by one of chemical formulas 3-1 to 3-4.
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formulas 3-3]
[ chemical formulas 3-4]
The arylcyanine compounds may be represented by chemical formula 4.
[ chemical formula 4]
In the chemical formula 4, the first and second organic solvents,
R9to R12Independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted C6 to C20 aryl.
The core may have a length of 1 to 3 nanometers.
The core may have a maximum absorption peak in wavelengths of 530 nanometers to 680 nanometers.
The arylcyanine compound may be represented by one of chemical formulas 4-1 to 4-6.
[ chemical formula 4-1]
[ chemical formula 4-2]
[ chemical formulas 4-3]
[ chemical formulas 4-4]
[ chemical formulas 4-5]
[ chemical formulas 4-6]
The core-shell structured dye may comprise a core and a shell in a molar ratio of 1: 1.
The core-shell structured dye may be a green dye.
The colorant may further comprise a pigment.
The photosensitive resin composition may include 0.5 to 20% by weight of a colorant, based on the total amount of the photosensitive resin composition; 0.1 to 30% by weight of a binder resin; 0.1 to 30% by weight of a photopolymerizable compound (monomer); 0.1 to 5% by weight of a photopolymerization initiator; and the balance solvent.
The photosensitive resin composition may further include malonic acid, 3-amino-1, 2-propanediol, a silane-based coupling agent including a vinyl group or a (meth) acryloyloxy group, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof.
Another embodiment provides a photosensitive resin layer manufactured using the photosensitive resin composition.
Another embodiment provides a color filter comprising a photosensitive resin layer. Other embodiments of the invention are encompassed by the following detailed description.
The photosensitive resin composition according to the embodiment can implement a color filter having improved brightness and durability by using a core-shell dye comprising a shell having a specific structure surrounding an arylcyanine-based core.
Drawings
Fig. 1 is a view showing the cage width of the shell represented by chemical formulas 3 to 4.
Detailed Description
Hereinafter, embodiments of the present invention are described in detail. However, these embodiments are exemplary, the present invention is not limited thereto and the present invention is defined by the scope of the claims.
In the present specification, when a specific definition is not otherwise provided, "substituted" means that at least one hydrogen of a compound is replaced by a substituent selected from: halogen atoms (F, Cl, Br, or I), hydroxyl groups, C1 to C20 alkoxy groups, nitro groups, cyano groups, amino groups, imino groups, azido groups, amidino groups, hydrazine groups, hydrazino groups, carbonyl groups, carbamoyl groups, thiol groups, ester groups, ether groups, carboxyl groups or salts thereof, sulfonic acid groups or salts thereof, phosphoric acid or salts thereof, C1 to C20 alkyl groups, C2 to C20 alkenyl groups, C2 to C20 alkynyl groups, C6 to C30 aryl groups, C3 to C20 cycloalkyl groups, C3 to C20 cycloalkenyl groups, C3 to C20 cycloalkynyl groups, C2 to C20 heterocycloalkyl groups, C2 to C20 heterocycloalkenyl groups, C2 to C20 heterocycloalkynyl groups, and combinations thereof.
In the present specification, "heterocycloalkyl", "heterocycloalkenyl", "heterocycloalkynyl" and "heterocycloalkylene" refer to cycloalkyl, cycloalkenyl, cycloalkynyl and cycloalkylene cyclic compounds containing at least one heteroatom of N, O, S or P, when no special definition is otherwise provided.
In the present specification, "(meth) acrylate" means both "acrylate" and "methacrylate" when a specific definition is not otherwise provided.
In the present specification, "combination" means mixing or copolymerization when a specific definition is not otherwise provided.
In the present specification, when a definition is not otherwise provided, in the chemical formula, when a chemical bond is not drawn, hydrogen is bonded at a presumably given position.
In the present specification, "+" indicates a point of bonding the same or different atoms or chemical formulae, when no special definition is otherwise provided.
The photosensitive resin composition according to the embodiment comprises: (A) a colorant comprising a core-shell structured dye; (B) a binder resin; (C) a photopolymerizable compound; (D) a photopolymerization initiator; and (E) a solvent, wherein the core is an arylcyanine-based compound and the shell is represented by chemical formula 1.
[ chemical formula 1]
In the chemical formula 1, the first and second,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position),
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom,
m is an integer of 1 to 10,
n is an integer of 0 to 3, and
L1and L2Independently a single bond or a substituted or unsubstituted C1 to C10 alkylene.
In chemical formula 1, L1And L2May independently be a substituted or unsubstituted C1 to C10 alkylene. In this case, the solubility is improved and a structure in which a shell surrounds the arylcyanine based compound is easily formed.
For example, the core-shell dye according to the embodiment includes a non-covalent bond, i.e., a hydrogen bond, between an oxygen atom of the arylcyanine-based compound and a hydrogen atom bonded to a nitrogen atom of the shell represented by chemical formula 1.
Generally, an arylcyanine compound is generally used as a green dye because it has improved green spectral characteristics and a high molar absorption coefficient. However, after manufacturing a color resist having inferior durability compared to a pigment, brightness may be reduced during a baking process. In the photosensitive resin compositions according to the examples, a core-shell structure compound in which a shell represented by chemical formula 1 uses an arylcyanine based compound as a core to form a core-shell structure was used as a colorant instead of a conventional arylcyanine based compound. The core-shell structured compound is used as a colorant to improve the durability of the color filter, thereby realizing a color filter having high brightness and high contrast ratio.
Hereinafter, each component is specifically described.
(A) Coloring agent
The photosensitive resin composition according to the embodiment includes a core-shell structured dye.
As described above, in the color filter made of the pigment-type photosensitive resin composition, there are limitations on brightness and contrast ratio due to the pigment particle size. In addition, for application to an image sensor, a resin composition composed of smaller particles is required for forming a fine pattern. In order to achieve this, efforts have been made to implement a color filter having improved brightness and contrast ratio by introducing a dye that does not form particles instead of a pigment to prepare a photosensitive resin composition suitable for the dye. However, the dye has weak durability compared to the pigment, and thus has a limitation in improving brightness and contrast ratio.
However, in the case of the dye used as the colorant in the photosensitive resin composition according to the example, the center of the arylcyanine based compound having excellent green spectral characteristics and a high molar extinction coefficient is surrounded by the macrocyclic compound represented by chemical formula 1, the durability can be improved more than the pigment-type photosensitive resin composition and the dye-type photosensitive resin composition to implement a color filter having brightness and contrast ratio.
Specifically, the core-shell dye has a structure consisting of an arylcyanine type core around which a shell of a macrocyclic compound represented by chemical formula 1 surrounds to form a coating layer, and a shell surrounding the core. Due to this structure, that is, by having a structure in which the arylcyanine based compound exists in the ring represented by chemical formula 1, the durability of the dye having the core-shell structure may be improved and thus a color filter having high brightness and high contrast ratio may be implemented.
For example, the shell may be represented by chemical formula 2.
[ chemical formula 2]
In the chemical formula 2, the first and second organic solvents,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position),
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom, and
n is an integer of 0 to 3.
For example, in chemical formulas 1 and 2, R1May be a hydrogen atom, and R2To R5May independently be a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group, provided that R2To R5Is a substituted or unsubstituted C1 to C20 alkyl group.
For example, in chemical formulas 1 and 2, R1May be a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position), R2To R5Independently a hydrogen atom.
For example, R1May be a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position), and R is2To R5At least one of which may be a substituted or unsubstituted C1 to C20 alkyl group.
For example, chemical formula 2 may be represented by chemical formula 2A.
[ chemical formula 2A ]
In the chemical formula 2A, the metal oxide,
R1is a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position), and
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group.
For example, the shell may be represented by one of chemical formulas 2-1 to 2-3.
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
In chemical formulas 2-1 to 2-3,
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R7and R8Independently a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6(wherein R is6Is a substituted or unsubstituted C1 to C20 alkyl group, and is a bonding position).
For example, the shell may have a cage width of 6.5 to 7.5 angstroms and a volume of 10 to 16 angstroms. The cage width refers to an internal distance of the shell in the present disclosure, for example, a distance between two different phenylene groups in which two methylene groups are bonded in the shell represented by chemical formula 2 (see fig. 1). When the shell has a cage width within the range, a core-shell dye having a structure surrounding the arylcyanine based compound can be obtained, and thus when the core-shell dye is used as a colorant of the photosensitive resin composition, a color filter having improved durability and high luminance can be implemented.
For example, the shell may be represented by one of chemical formula 3-1 to chemical formula 3-4, but is not limited thereto.
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formulas 3-3]
[ chemical formulas 3-4]
For example, in the core-shell dye, the arylcyanine based compound constituting the core may be represented by chemical formula 4.
[ chemical formula 4]
In the chemical formula 4, the first and second organic solvents,
R9to R12Independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted C6 to C20 aryl.
For example, in chemical formula 4,R9and R11May independently be a substituted or unsubstituted C1 to C20 alkyl group or a substituted or unsubstituted C3 to C20 cycloalkyl group, and R10And R12And may independently be a substituted or unsubstituted C6 to C20 aryl group.
For example, R9And R11May independently be "C1 to C20 alkyl substituted or unsubstituted by C1 to C10 alkoxy" or "C3 to C20 cycloalkyl substituted or unsubstituted by C1 to C10 alkoxy".
For example, the C1 to C10 alkoxy group may be an unsubstituted C1 to C10 alkoxy group or a C1 to C6 alkoxy group substituted with a C1 to C4 alkyl group.
The compound represented by chemical formula 4 has three types of resonance structures as shown in the following drawings, but in the present specification, the compound having one type of resonance structure and represented by chemical formula 4 is shown for convenience. In other words, the compound represented by chemical formula 4 may have any one type of structure among three types of resonance structures.
For example, the core (that is, the arylcyanine based compound) may be represented by one of chemical formulas 4-1 to 4-6, but is not limited thereto.
[ chemical formula 4-1]
[ chemical formula 4-2]
[ chemical formulas 4-3]
[ chemical formulas 4-4]
[ chemical formulas 4-5]
[ chemical formulas 4-6]
For example, when the compounds represented by chemical formulas 4-1 to 4-6, and particularly the compounds represented by chemical formulas 4-6, are used for the photosensitive resin composition (e.g., as a dye), the solubility to a solvent, which will be described later, may be greater than or equal to 5, such as 5 to 10. The solubility can be obtained by the amount (g) of the dye (compound) dissolved in 100 g of the solvent. When the compound (e.g., dye) has solubility in the range, compatibility with other components (that is, a binder resin, a photopolymerizable monomer, and a photopolymerization initiator described later) in the photosensitive resin composition and coloring characteristics can be ensured, and precipitation of the dye can be prevented.
For example, the compounds represented by chemical formulas 4-1 to 4-6 may have improved heat resistance. That is, the thermal decomposition temperature measured using a thermogravimetric analyzer (TGA) may be greater than or equal to 200 deg.C, such as 200 deg.C to 300 deg.C.
The length of the compound represented by chemical formula 4 included in or composed of the core may be 1 nm to 3 nm, for example, 1.5 nm to 2 nm. When the compound represented by chemical formula 4 has a length within the range, a core-shell structure may be easily formed. In other words, the compound represented by chemical formula 4 has a length within the range and thus a structure in which the compound represented by chemical formula 4 is surrounded by a shell, which is a macrocyclic compound represented by chemical formula 1, can be easily formed. When a compound having a length outside the range is used, a structure in which the shell does not surround the core compound may not be obtained, and durability may not be improved.
For example, the core-shell structured compound may have a maximum absorption peak in wavelengths of 530 nanometers to 680 nanometers. The dye having a core-shell structure of spectral characteristics is used, for example, as a green dye and thus a photosensitive resin composition for a color filter having high brightness and high contrast ratio can be provided.
For example, the core-shell structured compound may comprise a core and a shell of the arylcyanine type at a molar ratio of 1: 1. When the core and the shell are present in the molar ratio, a coating layer (shell) surrounding the arylcyanine based core can be preferably formed.
For example, the core-shell structured dye may be represented by one of the compounds represented by chemical formulas 5-1 to 5-24, but is not limited thereto.
[ chemical formula 5-1]
[ chemical formula 5-2]
[ chemical formulas 5-3]
[ chemical formulas 5-4]
[ chemical formulas 5 to 5]
[ chemical formulas 5 to 6]
[ chemical formulas 5 to 7]
[ chemical formulas 5 to 8]
[ chemical formulas 5 to 9]
[ chemical formulas 5 to 10]
[ chemical formulas 5 to 11]
[ chemical formulas 5 to 12]
[ chemical formulas 5 to 13]
[ chemical formulas 5 to 14]
[ chemical formulas 5 to 15]
[ chemical formulas 5 to 16]
[ chemical formulas 5 to 17]
[ chemical formulas 5 to 18]
[ chemical formulas 5 to 19]
[ chemical formulas 5 to 20]
[ chemical formulas 5 to 21]
[ chemical formulas 5 to 22]
[ chemical formulas 5 to 23]
[ chemical formulas 5 to 24]
The core-shell dye can be used alone as the green dye and can be mixed with the auxiliary dye.
The auxiliary dye may be triarylmethane-based dye, anthraquinone-based dye, benzylidene-based dye, cyanine-based dye, phthalocyanin-based dye, azaporphyrin-based dye, indigo-based dye, xanthene-based dye, pyridone azo-based dye, and the like.
The core-shell dye may be mixed with the pigment. That is, the colorant may further comprise a pigment.
The pigment may be a red pigment, a green pigment, a blue pigment, a yellow pigment, a black pigment, and the like.
Examples of the red pigment may be c.i. red pigment 254, c.i. red pigment 255, c.i. red pigment 264, c.i. red pigment 270, c.i. red pigment 272, c.i. red pigment 177, c.i. red pigment 89, and the like. Examples of the green pigment may be c.i. green pigment 7, c.i. green pigment 36, c.i. green pigment 58, c.i. green pigment 59, and the like. Examples of the blue pigment may be copper phthalocyanine pigments such as c.i. blue pigment 15:6, c.i. blue pigment 15:1, c.i. blue pigment 15:2, c.i. blue pigment 15:3, c.i. blue pigment 15:4, c.i. blue pigment 15:5, c.i. blue pigment 16, and the like. Examples of the yellow pigment may be isoindoline-based pigments such as c.i. yellow pigment 139 and the like; quinoline yellow pigments such as c.i. yellow pigment 138 and the like; nickel complex pigments such as c.i. yellow pigment 150 and the like. Examples of black pigments may be aniline black, perylene black, titanium black, carbon black, and the like. The pigments may be used alone or in a mixture of two or more and are not limited thereto.
The pigment may be contained in the photosensitive resin composition for a color filter in a pigment dispersion state. The pigment dispersion liquid may be composed of a pigment and a solvent, a dispersant, a dispersion resin, and the like.
The solvent may be ethylene glycol acetate, ethyl cellosolve (ethyl cellosolve), propylene glycol methyl ether acetate, ethyl lactate, polyethylene glycol, cyclohexanone, propylene glycol methyl ether, and the like, and desirably is propylene glycol methyl ether acetate.
The dispersant contributes to uniform dispersion of the pigment, and may include a nonionic dispersant, an anionic dispersant, or a cationic dispersant. Specific examples may be polyalkylene glycol or an ester thereof, polyoxyalkylene, polyol ester alkylene oxide addition product, alcohol alkylene oxide addition product, sulfonic acid ester, sulfonic acid salt, carboxylic acid ester, carboxylic acid salt, alkylamide alkylene oxide addition product, alkylamine, and may be used alone or in a mixture of two or more.
The dispersion resin may be an acryl-based resin including a carboxyl group, and improves the stability of the pigment dispersion liquid and the pattern characteristics of the pixels.
When mixing the core-shell dye with the pigment, the core-shell dye and the pigment may be mixed in a weight ratio of 1:9 to 9:1, and specifically in a weight ratio of 3:7 to 7: 3. When the core-shell dye and the pigment are mixed in the weight ratio range, high brightness and contrast ratio can be obtained while maintaining color characteristics.
The colorant may be included in an amount of 0.5 to 20 wt% (e.g., 1 to 15 wt%) based on the total amount of the photosensitive resin composition. When the colorant is used in the range, high brightness and high contrast ratio at desired color coordinates can be achieved.
(B) Adhesive resin
The binder resin may be a copolymer of a first ethylenically unsaturated monomer and a second ethylenically unsaturated monomer copolymerizable with the first ethylenically unsaturated monomer and a resin comprising at least one acryl-based repeating unit.
The first ethylenically unsaturated monomer is an ethylenically unsaturated monomer containing at least one carboxyl group. Examples of monomers include acrylic acid, methacrylic acid, maleic acid (maleic acid), itaconic acid (itaconic acid), fumaric acid (fumaric acid), or combinations thereof.
The first ethylenically unsaturated monomer may be included in an amount of 5 to 50 wt% (e.g., 10 to 40 wt%) based on the total amount of the alkali-soluble resin.
Examples of the second ethylenically unsaturated monomer may include aromatic vinyl compounds such as styrene, α -methylstyrene, vinyltoluene, vinylbenzyl methyl ether, and the like; unsaturated carboxylic acid ester compounds such as methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate, and the like; unsaturated carboxylic acid aminoalkyl ester compounds such as 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, and the like; vinyl carboxylate compounds such as vinyl acetate, vinyl benzoate, and the like; unsaturated carboxylic acid glycidyl ester compounds such as glycidyl (meth) acrylate and the like; vinyl cyanide compounds such as (meth) acrylonitrile and the like; unsaturated amide compounds such as (meth) acrylamide and the like; and the like, and examples of the second ethylenically unsaturated monomer may be used alone or in the form of a mixture of two or more.
Examples of the binder resin may include methacrylic acid/benzyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene copolymer, methacrylic acid/benzyl methacrylate/2-hydroxyethyl methacrylate copolymer, methacrylic acid/benzyl methacrylate/styrene/2-hydroxyethyl methacrylate copolymer, and the like, but are not limited thereto, and examples of the binder resin may be used alone or in a mixture of two or more.
The binder resin may have a weight average molecular weight of 3,000 g/mole to 150,000 g/mole, for example 5,000 g/mole to 50,000 g/mole or 20,000 g/mole to 30,000 g/mole. When the binder resin has a weight average molecular weight within the range, the composition may have excellent close contact characteristics with the substrate, good physical and chemical characteristics, and appropriate viscosity.
The binder resin may have an acid value of 15mg KOH/g to 60mg KOH/g, for example 20mg KOH/g to 50mg KOH/g. When the binder resin has an acid value within the range, it may bring excellent pixel resolution.
The binder resin may be included in an amount of 0.1 to 30 wt% (e.g., 5 to 20 wt%) based on the total amount of the photosensitive resin composition. When the binder resin is included in the range, the composition may have excellent developability and improved crosslinking, and thus excellent surface flatness when manufactured into a color filter.
(C) Photopolymerizable monomers
The photopolymerizable monomer may be a monofunctional or polyfunctional ester of (meth) acrylic acid containing at least one ethylenically unsaturated double bond.
The photopolymerizable monomer has an ethylenically unsaturated double bond, and thus, can cause sufficient polymerization during exposure in the pattern forming process and form a pattern having excellent heat resistance, light resistance, and chemical resistance.
Specific examples of the photopolymerizable monomer may be 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, 4-butanediol di (meth) acrylate, 1, 6-hexanediol di (meth) acrylate, bisphenol a di (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, pentaerythritol hexa (meth) acrylate, dipentaerythritol di (meth) acrylate, dipentaerythritol tri (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, bisphenol a epoxy (meth) acrylate, and the like, Ethylene glycol monomethyl ether (meth) acrylate, trimethylolpropane tri (meth) acrylate, tris (meth) acryloyloxyethyl phosphate, aldehyde epoxy (meth) acrylate, and the like.
Commercially available examples of reactive unsaturated compounds are as follows. The monofunctional (meth) acrylate may comprise anix (Aronix)
(Toagosei chemical industry Co., Ltd.); kayalard (KAYARAD)
(Nippon Kayaku Co., Ltd.,. Ltd.);
(Osaka organic Chemical industry, Ltd.) and the like. Examples of difunctional (meth) acrylates may include anixox
(Toya Synthesis chemical industries, Ltd.), Kayarad
(Nippon Kagaku Co., Ltd.),
V-335
(osaka organic chemical industry limited) and the like. Examples of trifunctional (meth) acrylates may include anixox
(Toya Synthesis chemical industries, Ltd.), Kayarad
(Nippon Kagaku Co., Ltd.),
(Osaka, by disproportionation pharmaceuticals, Inc. (Osaka Yuki Kayaku Kogyo Co. Ltd.)) and the like. These may be used alone or in a mixture of two or more.
The photopolymerizable monomer may be treated with an acid anhydride to improve developability.
The photopolymerizable monomer may be included in an amount of 0.1 wt% to 30 wt% (e.g., 5 wt% to 20 wt%) based on the total amount of the photosensitive resin composition. When the photopolymerizable monomer is included in the range, pattern characteristics and developability may be improved during color filter manufacturing.
(D) Photopolymerization initiator
The photopolymerization initiator may include acetophenone-based compounds, benzophenone-based compounds, thioxanthone-based compounds, benzoin-based compounds, triazine-based compounds, oxime-based compounds, and the like.
Examples of the acetophenone compounds may include 2,2' -diethoxyacetophenone, 2' -dibutoxyacetophenone, 2-hydroxy-2-methylpropiophenone, p-tert-butyltrichloroacetophenone, p-tert-butyldichloroacetophenone, 4-chloroacetophenone, 2' -dichloro-4-phenoxyacetophenone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, and the like.
Examples of the benzophenone-based compound may be benzophenone, benzoyl benzoate, benzoyl methylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4' -bis (dimethylamino) benzophenone, 4' -bis (diethylamino) benzophenone, 4' -dimethylaminobenzophenone, 4' -dichlorobenzophenone, 3' -dimethyl-2-methoxybenzophenone, and the like.
Examples of the thioxanthone-based compound may include thioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2, 4-diethylthioxanthone, 2, 4-diisopropylthioxanthone, 2-chlorothioxanthone, and the like.
Examples of benzoin-based compounds may include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, benzyl dimethyl ketal, and the like.
Examples of the triazine-based compound may include 2,4, 6-trichloro-s-triazine, 2-phenyl-4, 6-bis (trichloromethyl) -s-triazine, 2- (3',4' -dimethoxystyryl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4' -methoxynaphthyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4, 6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4, 6-bis (trichloromethyl) -s-triazine, 2-biphenyl-4, 6-bis (trichloromethyl) -s-triazine, bis (trichloromethyl) -6-styryl-s-triazine, p-tolyl-4, 6-bis (trichloromethyl) -s-triazine, p-, 2- (naphthol) -4, 6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthol) -4, 6-bis (trichloromethyl) -s-triazine, 2-4-trichloromethyl (sunflower) -6-triazine (2-4-trichloromethyl (piperonyl) -6-triazine), 2-4-trichloromethyl (4' -methoxystyryl) -6-triazine, and the like.
Examples of oximes may include 2- (o-benzoyloxime) -1- [4- (phenylthio) phenyl ] -1, 2-octanedione, 1- (o-acetyloxime) -1- [ 9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl ] ethanone, and the like.
The photopolymerization initiator may include carbazole-based compounds, diketone-based compounds, sulfonium borate-based compounds, diazo-based compounds, imidazole-based compounds, bisimidazole-based compounds, fluorene-based compounds, and the like, in addition to the compounds.
The photopolymerization initiator may be included in an amount of 0.1 to 5 wt% (e.g., 1 to 3 wt%) based on the total amount of the photosensitive resin composition. When the photopolymerization initiator is included within the range, the composition may be sufficiently photopolymerizable when exposed during a pattern forming process for preparing a color filter, thereby achieving excellent sensitivity and improving transmittance.
(E) Solvent(s)
The solvent is not particularly limited, but examples of the solvent include alcohols such as methanol, ethanol, and the like; ethers such as dichloroethyl ether, n-butyl ether, diisoamyl ether, methylphenyl ether, tetrahydrofuran (tetrahydrofuran), and the like; glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, propylene glycol methyl ether, and the like; cellosolve acetates such as cellosolve methyl acetate, cellosolve ethyl acetate, cellosolve diethyl acetate, and the like; carbitols (carbitols) such as methyl ethyl carbitol, diethyl carbitol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether, and the like; propylene glycol alkyl ether acetates such as propylene glycol methyl ether acetate, propylene glycol propyl ether acetate and the like; aromatic hydrocarbons such as toluene, xylene, and the like; ketones such as methyl ethyl ketone, cyclohexanone, 4-hydroxy-4-methyl-2-pentanone, methyl-n-acetone, methyl-n-butanone, methyl-n-pentanone, 2-heptanone, and the like; saturated aliphatic monocarboxylic acid alkyl esters such as ethyl acetate, n-butyl acetate, isobutyl acetate and the like; alkyl lactate such as methyl lactate, ethyl lactate, and the like; alkyl glycolates such as methyl glycolate, ethyl glycolate, butyl glycolate, and the like; alkoxyalkyl acetates such as methoxymethyl acetate, methoxyethyl acetate, methoxybutyl acetate, ethoxymethyl acetate, ethoxyethyl acetate, and the like; alkyl 3-hydroxypropionates such as methyl 3-hydroxypropionate, ethyl 3-hydroxypropionate and the like; alkyl 3-alkoxypropionates, such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, methyl 3-ethoxypropionate, and the like; alkyl 2-hydroxypropionates such as methyl 2-hydroxypropionate, ethyl 2-hydroxypropionate, propyl 2-hydroxypropionate and the like; alkyl 2-alkoxypropionates, such as methyl 2-methoxypropionate, ethyl 2-ethoxypropionate, methyl 2-ethoxypropionate, and the like; alkyl 2-hydroxy-2-methylpropionates such as methyl 2-hydroxy-2-methylpropionate, ethyl 2-hydroxy-2-methylpropionate and the like; alkyl 2-alkoxy-2-methylpropionates such as methyl 2-methoxy-2-methylpropionate, ethyl 2-ethoxy-2-methylpropionate and the like; esters such as 2-hydroxyethyl propionate, 2-hydroxy-2-methylethyl propionate, hydroxyethyl acetate, methyl 2-hydroxy-3-methylbutyrate, and the like; or a ketoester compound such as ethylpyruvate. Further, the solvent may be N-methylformamide, N-dimethylformamide, N-methylformanilide, N-methylacetamide, N-dimethylacetamide, N-methylpyrrolidone, dimethyl sulfoxide, benzyl ethyl ether, dihexyl ether, acetylacetone, isophorone (isophorone), hexanoic acid, octanoic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ -butyrolactone, ethylene carbonate, propylene carbonate, cellosolve acetate, and the like. These may be used alone or in a mixture of two or more.
In view of blending property, reactivity, and the like, the solvent may contain glycol ethers such as ethylene glycol monoethyl ether and the like; ethylene glycol alkyl ether acetates such as cellosolve ethyl acetate and the like; esters, such as 2-hydroxyethyl propionate and the like; diethylene glycols, such as diethylene glycol monomethyl ether and the like; propylene glycol alkyl ether acetates such as propylene glycol monomethyl ether acetate, propylene glycol propyl ether acetate and the like.
The solvent may be included in a balance, and specifically, in an amount of 20 to 90 wt%, based on the total amount of the photosensitive resin composition.
When the solvent is included within the range, the photosensitive resin composition may have excellent coating characteristics and maintain excellent flatness in a layer having a thickness of 3 μm or more.
(F) Other additives
The photosensitive resin composition may further comprise other additives such as malonic acid; 3-amino-1, 2-propanediol; a silane-based coupling agent containing a vinyl group or a (meth) acryloyloxy group; a leveling agent; a fluorine-based surfactant; a radical polymerization initiator to prevent stains or spots during coating, to adjust leveling, or to prevent pattern residues due to non-development.
The photosensitive resin composition may further include an epoxy compound in order to improve the close contact property with the substrate.
Examples of the epoxy compound may include a phenol novolac epoxy compound (phenonol novolac epoxy compound), a tetramethyl biphenyl epoxy compound, a bisphenol a epoxy compound, a cycloaliphatic epoxy compound, or a combination thereof.
The amount of additive used can be controlled depending on the desired properties.
Another embodiment provides a photosensitive resin layer produced by using the photosensitive resin composition.
Another embodiment provides a color filter manufactured by using the photosensitive resin composition. The method of manufacturing the color filter is as follows.
A protective layer (SiN) of 500 to 1500 angstroms in thickness is coated on or over a bare glass substrate using a suitable method such as spin coating, slit coating, and the likex) The glass substrate of (1) is coated with a photosensitive resin composition for a color filter having a thickness of 3.1 to 3.4 μm. After the coating, the composition is irradiated with light to form a pattern required for a color filter. After the light irradiation, the coating layer is treated with an alkaline developer, and a non-irradiated region thereof can be dissolved, thereby forming a pattern for a color filter. This process is repeated depending on the desired R, G and the number of B colors to produce a color filter having the desired pattern.
In addition, the image pattern obtained by development is cured by heat treatment, actinic ray irradiation or the like, thereby improving crack resistance, solvent resistance and the like.
Hereinafter, the present invention is described in more detail with reference to examples. However, these examples should not be construed in any way as limiting the scope of the invention.
(preparation of monomolecular Compound)
(preparation example 1: preparation of intermediate A)
Aniline (10 mol), 4-bromotoluene (10 mol), Pd2(dba)3(0.1 mol) and Xphos (0.1 mol) were added to toluene, heated at 100 ℃ and then stirred for 24 hours. Ethyl acetate was added thereto and washed twice with water to extract an organic layer. The extracted organic layer was distilled under reduced pressure and purified by column chromatography to obtain intermediate a.
(preparation example 2: preparation of intermediate B-1)
2, 4-dimethyldiphenylamine (10 moles), 1, 2-epoxyhexane (12 moles) and sodium hydride (12 moles) were added to N, N-Dimethylformamide (DMF), heated at 90 ℃ and then stirred for 24 hours. Ethyl acetate was added thereto and washed twice with water to extract an organic layer. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain intermediate B-1.
(preparation example 3: preparation of intermediate B-2)
Intermediate B-2 was obtained according to the same method as preparation example 2, except that 1, 2-epoxybutane was used instead of 1, 2-epoxyhexane.
(preparation example 4: preparation of intermediate B-3)
Intermediate B-3 was obtained according to the same method as preparation example 2, except that intermediate a was used instead of 2, 4-dimethyldiphenylamine.
(preparation example 5: preparation of intermediate B-4)
Intermediate B-4 was obtained according to the same method as preparation example 2, except that 1, 2-epoxycyclohexane was used instead of 1, 2-epoxyhexane.
(preparation example 6: preparation of intermediate C-1)
Intermediate B-1(10 mmol), methyl iodide (15 mmol) and sodium hydride (15 mmol) were added to N, N-dimethylformamide and stirred at room temperature for 24 hours. Ethyl acetate was added thereto and washed twice with water to extract an organic layer. The extracted organic layer was distilled under reduced pressure and separated by column chromatography to obtain intermediate C-1.
(preparation example 7: preparation of intermediate C-2)
The compound represented by intermediate C-2 was obtained according to the same method as that of preparation example 6, except that 2-iodopropane was used instead of methyl iodide.
(preparation example 8: preparation of intermediate C-3)
A compound represented by intermediate C-3 was obtained in the same manner as in preparation example 6, except that intermediate B-2 was used instead of intermediate B-1.
(preparation example 9: preparation of intermediate C-4)
The compound represented by intermediate C-4 was obtained according to the same method as that of preparation example 8, except that ethyl iodide was used instead of methyl iodide.
(preparation example 10: preparation of intermediate C-5)
A compound represented by intermediate C-5 was obtained in the same manner as in preparation example 6, except that intermediate B-4 was used instead of intermediate B-1.
(preparation example 11: preparation of intermediate C-6)
A compound represented by intermediate C-6 was obtained in the same manner as in preparation example 10, except that 1-iodo-2-ethylhexane was used instead of methyl iodide.
(preparation example 12: preparation chemical formula 4-1)
Intermediate C-1(60 mmol) and 3, 4-dihydroxy-3-cyclobutyne-1, 2-dione (30 mmol) were added in toluene (200 ml) and butanol (200 ml) and refluxed to obtain a product, and the product was removed with a Dean-stark distillation apparatus. After stirring for 12 hours, the green reaction was distilled under reduced pressure and purified by column chromatography to obtain the compound represented by chemical formula 4-1.
(preparation example 13: preparation chemical formula 4-2)
The compound represented by chemical formula 4-2 was obtained according to the same method as preparation example 12, except that intermediate C-2 was used instead of intermediate C-1.
(preparation example 14: preparation chemical formula 4-3)
A compound represented by chemical formula 4-3 was obtained according to the same method as preparation example 12, except that intermediate C-3 was used instead of intermediate C-1.
(preparation example 15: preparation chemical formula 4-4)
A compound represented by chemical formula 4-4 was obtained according to the same method as preparation example 12, except that intermediate C-4 was used instead of intermediate C-1.
(preparation example 16: preparation chemical formula 4-5)
The compound represented by chemical formula 4-5 was obtained according to the same method as preparation example 12, except that intermediate C-5 was used instead of intermediate C-1.
(preparation example 17: preparation chemical formula 4-6)
The compound represented by chemical formula 4-6 was obtained according to the same method as preparation example 12, except that intermediate C-6 was used instead of intermediate C-1.
(preparation of core-Shell dye)
(Synthesis example 1: Synthesis chemical formula 5-1)
The compound represented by chemical formula 4-1 (5 mmol) was dissolved in 600 ml of chloroform solvent, and triethylamine (triethylimine; TEA) (50 mmol) was then added thereto. 2, 6-pyridinedicarbonyl dichloride (20 mmol) and (2,3,5, 6-tetramethyl-1, 4-phenylene) dimethanamine (20 mmol) were dissolved in 60 ml of chloroform and added simultaneously in a dropwise manner at room temperature over a period of 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain the compound represented by chemical formula 5-1.
Maldi-tof MS：1346.75m/z
(Synthesis example 2: Synthesis chemical formula 5-2)
The compound represented by chemical formula 5-2 was obtained according to the same method as synthetic example 1, except that the compound represented by chemical formula 4-2 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1402.82m/z
(Synthesis example 3: Synthesis chemical formula 5-3)
The compound represented by chemical formula 5-3 was obtained according to the same method as synthetic example 1, except that the compound represented by chemical formula 4-3 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1290.60m/z
(Synthesis example 4: Synthesis chemical formula 5-4)
The compound represented by chemical formula 5-4 was obtained according to the same method as synthetic example 1, except that the compound represented by chemical formula 4-4 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1318.72m/z
(Synthesis example 5: Synthesis chemical formula 5-5)
The compound represented by chemical formula 5-5 was obtained according to the same method as synthetic example 1, except that the compound represented by chemical formula 4-5 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1342.72m/z
(Synthesis example 6: Synthesis chemical formula 5-6)
The compounds represented by chemical formulas 5 to 6 were obtained according to the same method as synthetic example 1, except that the compounds represented by chemical formulas 4 to 6 were used instead of the compounds represented by chemical formula 4-1.
Maldi-tof MS：1538.94m/z
(Synthesis example 7: Synthesis chemical formula 5-7)
The compound represented by chemical formula 4-1 (5 mmol) was dissolved in 600 ml of chloroform solvent, and triethylamine (50 mmol) was then added thereto. 2, 6-pyridinedicarbonyl dichloride (20 mmol) and (2-methyl-1, 4-phenylene) dimethanamine (20 mmol) were dissolved in 60 ml of chloroform and added simultaneously in a dropwise manner at room temperature over a period of 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain the compounds represented by chemical formulas 5 to 7.
Maldi-tof MS：1262.66m/z
(Synthesis example 8: Synthesis chemical formula 5-8)
The compounds represented by chemical formulas 5 to 8 were obtained according to the same method as synthetic example 7, except that the compound represented by chemical formula 4-2 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1318.72m/z
(Synthesis example 9: Synthesis chemical formula 5-9)
Compounds represented by chemical formulas 5 to 9 were obtained according to the same method as synthetic example 7, except that the compound represented by chemical formula 4-3 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1206.59m/z
(Synthesis example 10: Synthesis chemical formula 5-10)
Compounds represented by chemical formulas 5 to 10 were obtained according to the same method as synthetic example 7, except that the compound represented by chemical formula 4-4 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1234.63m/z
(Synthesis example 11: Synthesis chemical formula 5-11)
The compounds represented by chemical formulas 5 to 11 were obtained according to the same method as synthetic example 7, except that the compounds represented by chemical formulas 4 to 5 were used instead of the compounds represented by chemical formula 4-1.
Maldi-tof MS：1258.63m/z
(Synthesis example 12: Synthesis chemical formula 5-12)
Compounds represented by chemical formulas 5 to 12 were obtained according to the same method as synthetic example 7, except that the compound represented by chemical formula 4-6 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1454.84m/z
(Synthesis example 13: Synthesis chemical formulas 5-13)
The compound represented by chemical formula 4-1 (5 mmol) was dissolved in 600 ml of chloroform solvent, and triethylamine (50 mmol) was then added thereto. 4-trifluoromethylpyridine-2, 6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 ml of chloroform and added simultaneously in a dropwise manner at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain compounds represented by chemical formulas 5 to 13.
Maldi-tof MS：1370.60m/z
(Synthesis example 14: Synthesis chemical formulas 5 to 14)
Compounds represented by chemical formulas 5 to 14 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-2 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1426.66m/z
(Synthesis example 15: Synthesis chemical formulas 5-15)
Compounds represented by chemical formulas 5 to 15 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-3 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1314.54m/z
(Synthesis example 16: Synthesis chemical formula 5-16)
Compounds represented by chemical formulas 5 to 16 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-4 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1342.57m/z
(Synthesis example 17: Synthesis chemical formulas 5-17)
Compounds represented by chemical formulas 5 to 17 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-5 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1366.57m/z
(Synthesis example 18: Synthesis chemical formula 5-18)
Compounds represented by chemical formulas 5 to 18 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-6 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1562.79m/z
(Synthesis example 19: Synthesis chemical formulas 5-19)
The compound represented by chemical formula 4-1 (5 mmol) was dissolved in 600 ml of chloroform solvent, and triethylamine (50 mmol) was then added thereto. 2-ethylhexyloxypyridine-2, 6-dicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 ml of chloroform and added simultaneously in a dropwise manner at room temperature for 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain compounds represented by chemical formulas 5 to 19.
Maldi-tof MS：1490.87m/z
(Synthesis example 20: Synthesis chemical formula 5-20)
Compounds represented by chemical formulas 5 to 20 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-2 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1546.93m/z
(Synthesis example 21: Synthesis chemical formula 5-21)
Compounds represented by chemical formulas 5 to 21 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-3 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1434.80m/z
(Synthesis example 22: Synthesis chemical formula 5-22)
Compounds represented by chemical formulas 5 to 22 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-4 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1462.83m/z
(Synthesis example 23: Synthesis chemical formula 5-23)
Compounds represented by chemical formulas 5 to 23 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-5 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1486.83m/z
(Synthesis example 24: Synthesis chemical formulas 5-24)
Compounds represented by chemical formulas 5 to 24 were obtained according to the same method as synthetic example 13, except that the compound represented by chemical formula 4-6 was used instead of the compound represented by chemical formula 4-1.
Maldi-tof MS：1683.05m/z
(comparative Synthesis example 1)
The compound represented by chemical formula 4-1 (5 mmol) was dissolved in 600 ml of chloroform solvent, and triethylamine (50 mmol) was then added thereto. 2, 6-pyridinedicarbonyl dichloride (20 mmol) and p-xylylenediamine (20 mmol) were dissolved in 60 ml of chloroform and added simultaneously at room temperature in a dropwise manner over a period of 5 hours. After 12 hours, the mixture was distilled under reduced pressure and separated by column chromatography to obtain a core-shell structure compound.
(preparation of photosensitive resin composition)
The following components were used to prepare a photosensitive resin composition.
(A) Coloring agent
(dyes)
(A-1) Synthesis of core-shell dye prepared in example 1 (represented by chemical formula 5-1)
(A-2) Synthesis of core-shell dye prepared in example 2 (represented by chemical formula 5-2)
(A-3) Synthesis of core-shell dye prepared in example 3 (represented by chemical formula 5-3)
(A-4) Synthesis of core-shell dye prepared in example 4 (represented by chemical formula 5-4)
(A-5) Synthesis of core-shell dye prepared in example 5 (represented by chemical formula 5-5)
(A-6) Synthesis of core-shell dye prepared in example 6 (represented by chemical formula 5-6)
(A-7) Synthesis of core-shell dye prepared in example 7 (represented by chemical formulas 5 to 7)
(A-8) Synthesis of core-shell dye prepared in example 8 (represented by chemical formulas 5 to 8)
(A-9) Synthesis of core-shell dye prepared in example 9 (represented by chemical formulas 5 to 9)
(A-10) Synthesis of core-shell dye prepared in example 10 (represented by chemical formulas 5 to 10)
(A-11) Synthesis of core-shell dye prepared in example 11 (represented by chemical formulas 5 to 11)
(A-12) Synthesis of core-shell dye prepared in example 12 (represented by chemical formulas 5 to 12)
(A-13) Synthesis of core-shell dye prepared in example 13 (represented by chemical formulas 5 to 13)
(A-14) Synthesis of core-shell dye prepared in example 14 (represented by chemical formulas 5 to 14)
(A-15) Synthesis of core-shell dye prepared in example 15 (represented by chemical formulas 5 to 15)
(A-16) Synthesis of core-shell dye prepared in example 16 (represented by chemical formulas 5 to 16)
(A-17) Synthesis of core-shell dye prepared in example 17 (represented by chemical formulas 5 to 17)
(A-18) Synthesis of core-shell dye prepared in example 18 (represented by chemical formulas 5 to 18)
(A-19) Synthesis of core-shell dyes prepared in example 19 (represented by chemical formulas 5 to 19)
(A-20) Synthesis of core-shell dye prepared in example 20 (represented by chemical formulas 5 to 20)
(A-21) Synthesis of core-shell dye prepared in example 21 (represented by chemical formulas 5 to 21)
(A-22) Synthesis of core-shell dye prepared in example 22 (represented by chemical formulas 5 to 22)
(A-23) Synthesis of core-shell dye prepared in example 23 (represented by chemical formulas 5 to 23)
(A-24) Synthesis of core-shell dyes prepared in example 24 (represented by chemical formulas 5 to 24)
(A-25) core-Shell dye prepared in comparative Synthesis example 1
(pigment)
(A' -1) C.I. Green pigment 58
(B) Adhesive resin
Methacrylic acid/benzyl methacrylate copolymer having a weight average molecular weight of 22,000 g/mole (mixing weight ratio: 15 wt%/85 wt%).
(C) Photopolymerizable monomers
Dipentaerythritol hexaacrylate
(D) Photopolymerization initiator
(D-1)1, 2-octanedione
(D-2) 2-dimethylamino-2- (4-methyl-benzyl) -1- (4-morpholin-4-yl-phenyl) -butan-1-one
(E) Solvent(s)
(E-1) Cyclohexanone
(E-2) propylene glycol monomethyl ether acetate
Examples 1 to 24, comparative example 1 and comparative example 2
Photosensitive resin compositions were prepared by mixing each component of the compositions shown in tables 1 and 2. Specifically, a photopolymerization initiator was dissolved in a solvent, the solution was stirred at room temperature for 2 hours, a colorant was added thereto, the mixture was stirred for 30 minutes, a binder resin and a photopolymerizable monomer were added thereto, and the obtained mixture was stirred at room temperature for 2 hours. The solution was filtered three times to remove impurities and prepare a photosensitive resin composition.
[ Table 1]
(unit: wt%)
[ Table 2]
(unit: wt%)
(evaluation)
Evaluation 1: evaluation of durability
Photosensitive resin compositions according to examples 1 to 24, comparative example 1 and comparative example 2, which were 1 to 3 μm thick, were respectively coated on degreased glass substrates 1 mm thick and dried on a hot plate at 90 ℃ for 2 minutes to obtain films. The film was exposed with a high-pressure mercury lamp having a dominant wavelength of 365 nm and dried in an oven at 200 ℃ for 60 hours, and a spectrophotometer (MCPD3000, tsukamur Electronics co., Ltd.) measured the color coordinate change and thereby evaluated the durability, and the results are shown in table 3.
Evaluation reference for durability
Excellent: color coordinate change of less than 0.003
Good: a color coordinate change of 0.003 or more and 0.005 or less
Poor: color coordinate change is higher than 0.005
[ Table 3]
According to table 3, the photosensitive resin compositions of examples 1 to 24 including the core-shell dye according to the examples showed increased durability.
Evaluation 2: evaluation of luminance and contrast ratio
Photosensitive resin compositions according to examples 1 to 24, comparative example 1 and comparative example 2, which were 1 to 3 μm thick, were respectively coated on a 1 mm thick degreased glass substrate and dried on a hot plate at 90 ℃ for 2 minutes to form a film. Subsequently, the film was exposed to light using a high pressure mercury lamp having a main wavelength of 365 nm and dried in a forced convection oven of a 200 ℃ oven for 5 minutes. The luminance and contrast ratio of the pixel layer were measured using a spectrophotometer (MCPD3000, tsukamur electronic corporation), and the results are shown in table 4.
[ Table 4]
According to table 4, examples 1 to 24 including the core-shell dye according to the embodiment show high brightness and high contrast ratio, compared to comparative examples 1 and 2 not including the core-shell dye.
While the invention has been described in connection with what is presently considered to be practical example embodiments, it is to be understood that the invention is not to be limited to the disclosed embodiments, but on the contrary, is intended to cover various modifications and equivalent arrangements included within the spirit and scope of the appended claims. The foregoing embodiments are therefore to be considered in all respects illustrative rather than limiting of the invention.
Claims (16)
1. A photosensitive resin composition comprises
(A) Colorants, including core-shell structured dyes;
(B) a binder resin;
(C) a photopolymerizable compound;
(D) a photopolymerization initiator; and
(E) a solvent, a water-soluble organic solvent,
wherein the core comprises an arylcyanine compound, and
the shell is represented by chemical formula 1:
[ chemical formula 1]
Wherein, in chemical formula 1,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6,
R6Is a substituted or unsubstituted C1 to C20 alkyl group, is a bonding position,
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom,
m is an integer of 1 to 10,
n is an integer of 0 to 3, and
L1and L2Independently a single bond or a substituted or unsubstituted C1 to C10 alkylene.
2. The photosensitive resin composition of claim 1, wherein the shell is represented by chemical formula 2:
[ chemical formula 2]
Wherein, in chemical formula 2,
R1is a hydrogen atom, a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6,
R6Is a substituted or unsubstituted C1 to C20 alkyl group, is a bonding position,
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
with the proviso that R1To R5Not simultaneously being a hydrogen atom, and
n is an integer of 0 to 3.
3. The photosensitive resin composition of claim 1, wherein the shell is represented by one of chemical formulas 2-1 to 2-3:
[ chemical formula 2-1]
[ chemical formula 2-2]
[ chemical formulas 2-3]
Wherein, in chemical formulas 2-1 to 2-3,
R2to R5Independently a hydrogen atom or a substituted or unsubstituted C1 to C20 alkyl group,
R7and R8Independently a halogen atom, a substituted OR unsubstituted C1 to C20 alkyl group OR-OR6,
R6Is a substituted or unsubstituted C1 to C20 alkyl group, which is a bonding position.
4. The photosensitive resin composition of claim 1, wherein the shell has a cage width of 6.5 to 7.5 angstroms.
5. The photosensitive resin composition of claim 1, wherein the shell is represented by one of chemical formulas 3-1 to 3-4:
[ chemical formula 3-1]
[ chemical formula 3-2]
[ chemical formulas 3-3]
[ chemical formulas 3-4]
6. The photosensitive resin composition of claim 1, wherein the arylcyanine based compound is represented by chemical formula 4:
[ chemical formula 4]
Wherein, in chemical formula 4,
R9to R12Independently a substituted or unsubstituted C1 to C20 alkyl, a substituted or unsubstituted C3 to C20 cycloalkyl, or a substituted or unsubstituted C6 to C20 aryl.
7. The photosensitive resin composition of claim 1, wherein the core has a length of 1 to 3 nanometers.
8. The photosensitive resin composition of claim 1, wherein the core has a maximum absorption peak in a wavelength of 530 to 680 nanometers.
9. The photosensitive resin composition of claim 1, wherein the arylcyanine based compound is represented by one of chemical formulas 4-1 to 4-6:
[ chemical formula 4-1]
[ chemical formula 4-2]
[ chemical formulas 4-3]
[ chemical formulas 4-4]
[ chemical formulas 4-5]
[ chemical formulas 4-6]
10. The photosensitive resin composition of claim 1, wherein the core-shell structured dye comprises the core and the shell in a molar ratio of 1: 1.
11. The photosensitive resin composition of claim 1, wherein the core-shell structured dye is a green dye.
12. The photosensitive resin composition of claim 1, wherein the colorant further comprises a pigment.
13. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition comprises
Based on the total amount of the photosensitive resin composition,
0.5 to 20 weight percent of the colorant;
0.1 to 30% by weight of the binder resin;
0.1 to 30% by weight of the photopolymerizable compound;
0.1 to 5% by weight of the photopolymerization initiator; and
the balance of the solvent.
14. The photosensitive resin composition of claim 1, wherein the photosensitive resin composition further comprises malonic acid, 3-amino-1, 2-propanediol, a silane-based coupling agent comprising vinyl or (meth) acryloyloxy, a leveling agent, a surfactant, a radical polymerization initiator, or a combination thereof.
15. A photosensitive resin layer produced using the photosensitive resin composition described in any one of claims 1 to 14.
16. A color filter comprising the photosensitive resin layer according to claim 15.
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| KR10-2019-0051681 | 2019-05-02 | ||
| KR1020190051681A KR20200127482A (en) | 2019-05-02 | 2019-05-02 | Photosensitive resin composition, photosensitive resin layer including the same and color filter |
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Cited By (3)
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| CN115572492A (en) * | 2021-06-21 | 2023-01-06 | 三星Sdi株式会社 | Core-shell compound, photosensitive resin composition, photosensitive resin layer, color filter, and CMOS image sensor |
| CN115678308A (en) * | 2021-07-23 | 2023-02-03 | 三星Sdi株式会社 | Dye compound, photosensitive resin composition comprising the same, color filter and CMOS image sensor |
| CN115873420A (en) * | 2021-09-28 | 2023-03-31 | 三星Sdi株式会社 | Core-shell dye, photosensitive resin composition, photosensitive resin film, color filter, and CMOS image sensor |
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| KR20220094939A (en) * | 2020-12-29 | 2022-07-06 | 삼성에스디아이 주식회사 | Core-shell compound, photosensitive resin composition comprising the same, photosensitive resin layer, color filter and cmos image sensor |
| KR102603293B1 (en) * | 2021-03-24 | 2023-11-15 | 삼성에스디아이 주식회사 | Photosensitive resin composition comprising the same, photosensitive resin layer, color filter and cmos image sensor |
| KR20230013508A (en) * | 2021-07-19 | 2023-01-26 | 삼성에스디아이 주식회사 | Core-shell compound, photosensitive resin composition comprising the same, photosensitive resin layer, color filter and display device |
| WO2023162791A1 (en) * | 2022-02-25 | 2023-08-31 | 富士フイルム株式会社 | Infrared absorbing composition, infrared absorber, film, optical filter and solid-state imaging element |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012013945A (en) * | 2010-06-30 | 2012-01-19 | Fujifilm Corp | Colored curable composition, color filter, method for manufacturing color filter, solid imaging element and liquid crystal display element |
| KR20140072682A (en) * | 2012-12-05 | 2014-06-13 | 제일모직주식회사 | Core-shell dye, photosensitive resin composition for color filter including the same, and color filter using the same |
| CN104570605A (en) * | 2013-10-17 | 2015-04-29 | 住友化学株式会社 | Colored curable resin composition |
| JP2016117858A (en) * | 2014-12-22 | 2016-06-30 | 住友化学株式会社 | Colored curable resin composition |
| CN107793327A (en) * | 2016-09-05 | 2018-03-13 | 三星Sdi株式会社 | Compounds, nucleocapsid dyestuff, Photosensitve resin composition and colored filter |
| KR20180035074A (en) * | 2016-09-28 | 2018-04-05 | 삼성에스디아이 주식회사 | Novel compound, photosensitive resin composition including the same and color filter |
| KR20180107968A (en) * | 2017-03-23 | 2018-10-04 | 삼성에스디아이 주식회사 | Novel compound, core-shell dye and photosensitive resin composition including the same |
| KR20190001361A (en) * | 2017-06-27 | 2019-01-04 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer and color filter including the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102087260B1 (en) * | 2016-09-26 | 2020-03-10 | 삼성에스디아이 주식회사 | Novel compound, core-shell dye, photosensitive resin composition including the same, and color filter |
| KR102087259B1 (en) * | 2016-09-28 | 2020-03-10 | 삼성에스디아이 주식회사 | Novel compound, core-shell dye, photosensitive resin composition including the same, and color filter |
| US11091646B2 (en) * | 2017-08-14 | 2021-08-17 | Seta Biomedicals, Llc | Luminescent squaraine rotaxane compounds |
-
2019
- 2019-05-02 KR KR1020190051681A patent/KR20200127482A/en not_active Application Discontinuation
-
2020
- 2020-04-29 CN CN202010357498.2A patent/CN111880373A/en active Pending
- 2020-04-30 TW TW109114481A patent/TWI826684B/en active
- 2020-04-30 JP JP2020080504A patent/JP7111768B2/en active Active
-
2023
- 2023-02-01 KR KR1020230013928A patent/KR102624671B1/en active IP Right Grant
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2012013945A (en) * | 2010-06-30 | 2012-01-19 | Fujifilm Corp | Colored curable composition, color filter, method for manufacturing color filter, solid imaging element and liquid crystal display element |
| KR20140072682A (en) * | 2012-12-05 | 2014-06-13 | 제일모직주식회사 | Core-shell dye, photosensitive resin composition for color filter including the same, and color filter using the same |
| CN104570605A (en) * | 2013-10-17 | 2015-04-29 | 住友化学株式会社 | Colored curable resin composition |
| JP2016117858A (en) * | 2014-12-22 | 2016-06-30 | 住友化学株式会社 | Colored curable resin composition |
| CN107793327A (en) * | 2016-09-05 | 2018-03-13 | 三星Sdi株式会社 | Compounds, nucleocapsid dyestuff, Photosensitve resin composition and colored filter |
| KR20180035074A (en) * | 2016-09-28 | 2018-04-05 | 삼성에스디아이 주식회사 | Novel compound, photosensitive resin composition including the same and color filter |
| KR20180107968A (en) * | 2017-03-23 | 2018-10-04 | 삼성에스디아이 주식회사 | Novel compound, core-shell dye and photosensitive resin composition including the same |
| KR20190001361A (en) * | 2017-06-27 | 2019-01-04 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer and color filter including the same |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115572492A (en) * | 2021-06-21 | 2023-01-06 | 三星Sdi株式会社 | Core-shell compound, photosensitive resin composition, photosensitive resin layer, color filter, and CMOS image sensor |
| CN115678308A (en) * | 2021-07-23 | 2023-02-03 | 三星Sdi株式会社 | Dye compound, photosensitive resin composition comprising the same, color filter and CMOS image sensor |
| CN115873420A (en) * | 2021-09-28 | 2023-03-31 | 三星Sdi株式会社 | Core-shell dye, photosensitive resin composition, photosensitive resin film, color filter, and CMOS image sensor |
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| TW202041602A (en) | 2020-11-16 |
| KR102624671B1 (en) | 2024-01-12 |
| KR20230024934A (en) | 2023-02-21 |
| JP2020184073A (en) | 2020-11-12 |
| KR20200127482A (en) | 2020-11-11 |
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| TWI826684B (en) | 2023-12-21 |
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