JP6903854B2 - Colorant compounds and coloring compositions containing them - Google Patents
Colorant compounds and coloring compositions containing them Download PDFInfo
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- JP6903854B2 JP6903854B2 JP2019548924A JP2019548924A JP6903854B2 JP 6903854 B2 JP6903854 B2 JP 6903854B2 JP 2019548924 A JP2019548924 A JP 2019548924A JP 2019548924 A JP2019548924 A JP 2019548924A JP 6903854 B2 JP6903854 B2 JP 6903854B2
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- 150000001875 compounds Chemical class 0.000 title claims description 132
- 239000003086 colorant Substances 0.000 title claims description 50
- 239000000203 mixture Substances 0.000 title claims description 50
- 238000004040 coloring Methods 0.000 title claims description 47
- 239000000126 substance Substances 0.000 claims description 132
- 125000004432 carbon atom Chemical group C* 0.000 claims description 74
- 239000000049 pigment Substances 0.000 claims description 27
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000005110 aryl thio group Chemical group 0.000 claims description 23
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- 125000001931 aliphatic group Chemical group 0.000 claims description 12
- 101000614399 Homo sapiens Serine/threonine-protein phosphatase 2A regulatory subunit B'' subunit beta Proteins 0.000 claims description 10
- 102100040471 Serine/threonine-protein phosphatase 2A regulatory subunit B'' subunit beta Human genes 0.000 claims description 10
- 239000011347 resin Substances 0.000 claims description 10
- 229920005989 resin Polymers 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000178 monomer Substances 0.000 claims description 7
- 239000011230 binding agent Substances 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 5
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 4
- 150000004056 anthraquinones Chemical class 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 230000001747 exhibiting effect Effects 0.000 claims description 3
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 3
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 3
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical compound C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 claims description 3
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
- GJCOSYZMQJWQCA-UHFFFAOYSA-N 9H-xanthene Chemical compound C1=CC=C2CC3=CC=CC=C3OC2=C1 GJCOSYZMQJWQCA-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000001056 green pigment Substances 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 claims description 2
- QDLAGTHXVHQKRE-UHFFFAOYSA-N lichenxanthone Natural products COC1=CC(O)=C2C(=O)C3=C(C)C=C(OC)C=C3OC2=C1 QDLAGTHXVHQKRE-UHFFFAOYSA-N 0.000 claims description 2
- 125000005504 styryl group Chemical group 0.000 claims description 2
- 239000001052 yellow pigment Substances 0.000 claims description 2
- SLVOILNPGZPVOM-UHFFFAOYSA-N 1h-pyrano[3,2-b]pyrrole-2,3,5-trione Chemical compound C1=CC(=O)OC2=C1NC(=O)C2=O SLVOILNPGZPVOM-UHFFFAOYSA-N 0.000 claims 1
- 150000001721 carbon Chemical group 0.000 claims 1
- 239000001054 red pigment Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 43
- 239000011342 resin composition Substances 0.000 description 22
- 239000000758 substrate Substances 0.000 description 22
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
- 229940126062 Compound A Drugs 0.000 description 5
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
- WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000001723 curing Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 0 CC(C(c(c1c2*)c(*)c3c2c(*)c(*)c(*)c3*)=O)C1=O Chemical compound CC(C(c(c1c2*)c(*)c3c2c(*)c(*)c(*)c3*)=O)C1=O 0.000 description 3
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229940125904 compound 1 Drugs 0.000 description 3
- 229940125773 compound 10 Drugs 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 229940126214 compound 3 Drugs 0.000 description 3
- 229940125898 compound 5 Drugs 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 3
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 3
- 239000004973 liquid crystal related substance Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920002120 photoresistant polymer Polymers 0.000 description 3
- 238000010189 synthetic method Methods 0.000 description 3
- 238000000411 transmission spectrum Methods 0.000 description 3
- YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 2
- 125000005916 2-methylpentyl group Chemical group 0.000 description 2
- UNDDFQCMSGPPAR-UHFFFAOYSA-N CCCCSc(c(SCCCC)c(c(Cl)c1C(N2c3c4nc(C(C(c5cc(cccc6)c6cc55)=O)C5=O)ccc4c(CN(C(c4ccccc44)=O)C4=O)cc3)=O)SCCCC)c1C2=O Chemical compound CCCCSc(c(SCCCC)c(c(Cl)c1C(N2c3c4nc(C(C(c5cc(cccc6)c6cc55)=O)C5=O)ccc4c(CN(C(c4ccccc44)=O)C4=O)cc3)=O)SCCCC)c1C2=O UNDDFQCMSGPPAR-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N anhydrous diethylene glycol Natural products OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 238000000206 photolithography Methods 0.000 description 2
- 229940067265 pigment yellow 138 Drugs 0.000 description 2
- 125000003367 polycyclic group Chemical group 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
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- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
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- UVNPEUJXKZFWSJ-LMTQTHQJSA-N (R)-N-[(4S)-8-[6-amino-5-[(3,3-difluoro-2-oxo-1H-pyrrolo[2,3-b]pyridin-4-yl)sulfanyl]pyrazin-2-yl]-2-oxa-8-azaspiro[4.5]decan-4-yl]-2-methylpropane-2-sulfinamide Chemical compound CC(C)(C)[S@@](=O)N[C@@H]1COCC11CCN(CC1)c1cnc(Sc2ccnc3NC(=O)C(F)(F)c23)c(N)n1 UVNPEUJXKZFWSJ-LMTQTHQJSA-N 0.000 description 1
- IXJJELULBDAIMY-UHFFFAOYSA-N 1,2,5,6-tetrahydrotriazine Chemical compound C1CC=NNN1 IXJJELULBDAIMY-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 1
- MKPHQUIFIPKXJL-UHFFFAOYSA-N 1,2-dihydroxypropyl 2-methylprop-2-enoate Chemical compound CC(O)C(O)OC(=O)C(C)=C MKPHQUIFIPKXJL-UHFFFAOYSA-N 0.000 description 1
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 description 1
- BIGYLAKFCGVRAN-UHFFFAOYSA-N 1,3,4-thiadiazolidine-2,5-dithione Chemical compound S=C1NNC(=S)S1 BIGYLAKFCGVRAN-UHFFFAOYSA-N 0.000 description 1
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-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
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 1
- IMQFZQVZKBIPCQ-UHFFFAOYSA-N 2,2-bis(3-sulfanylpropanoyloxymethyl)butyl 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(CC)(COC(=O)CCS)COC(=O)CCS IMQFZQVZKBIPCQ-UHFFFAOYSA-N 0.000 description 1
- UEICDZNUHYPLEP-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)-1,1-diphenylpropane-1,3-diol prop-2-enoic acid Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C1(=CC=CC=C1)C(O)(C(CO)(CO)CO)C1=CC=CC=C1 UEICDZNUHYPLEP-UHFFFAOYSA-N 0.000 description 1
- GDOBGDUGIFUCJV-UHFFFAOYSA-N 2,2-dimethylbutane;2-methylprop-2-enoic acid Chemical compound CCC(C)(C)C.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O GDOBGDUGIFUCJV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
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- DEDUBNVYPMOFDR-UHFFFAOYSA-N 2-ethoxypropan-1-ol Chemical compound CCOC(C)CO DEDUBNVYPMOFDR-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 1
- YTTFFPATQICAQN-UHFFFAOYSA-N 2-methoxypropan-1-ol Chemical compound COC(C)CO YTTFFPATQICAQN-UHFFFAOYSA-N 0.000 description 1
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- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 description 1
- 125000004920 4-methyl-2-pentyl group Chemical group CC(CC(C)*)C 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/04—Isoindoline dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour
- G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour based on liquid crystals, e.g. single liquid crystal display cells
- G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
- G02F1/1333—Constructional arrangements; Manufacturing methods
- G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
- G02F1/133509—Filters, e.g. light shielding masks
- G02F1/133514—Colour filters
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Nonlinear Science (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Architecture (AREA)
- Structural Engineering (AREA)
- Mathematical Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Optical Filters (AREA)
- Materials For Photolithography (AREA)
Description
[関連出願の相互参照]
本出願は、２０１７年９月４日付の韓国特許出願第１０−２０１７−０１１２６９１号および２０１８年８月２２日付の韓国特許出願第１０−２０１８−００９８１４２号に基づく優先権の利益を主張し、当該韓国特許出願の文献に開示された全ての内容は本明細書の一部として含まれる。
[Cross-reference of related applications]
This application claims the priority benefit under Korean Patent Application No. 10-2017-0112691 dated September 4, 2017 and Korean Patent Application No. 10-2018-0998142 dated August 22, 2018. All content disclosed in the literature of Korean patent applications is included as part of this specification.
本発明は、着色剤化合物およびこれを含む着色組成物に関する。より詳しくは、優れた色特性、耐熱性および溶解度を示す新規な構造の着色剤化合物およびこれを含む着色組成物に関する。 The present invention relates to a colorant compound and a coloring composition containing the same. More specifically, the present invention relates to a colorant compound having a novel structure exhibiting excellent color characteristics, heat resistance and solubility, and a coloring composition containing the same.
液晶表示装置（ＬＣＤ）および有機発光ダイオード（ＯＬＥＤ）などに用いられるカラーフィルターは、表示装置でカラー画像を実現するために使用されるもので、基本となる基板に色素を様々な方法を用いてコーティング、硬化し、パターン化する工程を経て製作される。 Color filters used in liquid crystal displays (LCDs) and organic light emitting diodes (OLEDs) are used to realize color images in display devices, and dyes are applied to the basic substrate by various methods. Manufactured through a process of coating, curing and patterning.
カラーフィルターは、ガラスなどの透明基板上に赤色、緑色、青色の３色の各画素部が形成されるものであって、画像表示装置や固体撮像素子に使用されるカラーフィルターは、通常、赤色（Ｒ）、緑色（Ｇ）、および青色（Ｂ）の三原色の着色パターンを有しており、通過する光を着色したり三原色に分離したりする役割を果たす。 The color filter has three color pixel portions of red, green, and blue formed on a transparent substrate such as glass, and the color filter used for an image display device or a solid-state image sensor is usually red. It has a coloring pattern of the three primary colors (R), green (G), and blue (B), and plays a role of coloring the passing light and separating it into the three primary colors.
前記赤色、緑色、青色を表示する色素は、微細な粒子、つまり、染料（Ｄｙｅ）または顔料（Ｐｉｇｍｅｎｔ）からなり、このような色素は所望の領域の色表示特性を得るため、単独で使用するよりも類似色を示す色素を混合して赤色、緑色、青色を表示することになる。 The dyes displaying red, green, and blue consist of fine particles, that is, dyes or pigments, and such dyes are used alone to obtain color display characteristics in a desired region. Dyes showing similar colors are mixed to display red, green, and blue.
色素として使用される物質は、共通的に色再現性上好ましい吸収特性を有すること、使用される条件下における耐光性、耐熱性、オゾンなどの酸化性ガスに対する耐性が良好であること、などが要求される。 Substances used as pigments commonly have favorable absorption characteristics in terms of color reproducibility, and have good light resistance, heat resistance, and resistance to oxidizing gases such as ozone under the conditions in which they are used. Required.
最近、液晶ディスプレイの大画面化および高鮮明化の技術開発が進められている。このような状況において液晶ディスプレイなどに使用するカラーフィルターは高い色純度が要求される。カラーフィルターの製造に用いられる多様な色素または着色剤は知られているが、公知の色材料のみを用いて色純度、輝度、明暗比を向上させる方法は漸次限界点に到達している。 Recently, technological developments for larger screens and higher clarity of liquid crystal displays have been promoted. In such a situation, a color filter used for a liquid crystal display or the like is required to have high color purity. Although various pigments or colorants used in the production of color filters are known, methods for improving color purity, brightness, and light-dark ratio using only known color materials have gradually reached the limit.
特に、顔料分散法を用いたカラーフィルターの製造時、顔料分散法により添加される顔料誘導体および分散剤などによって感光性樹脂組成物中の顔料含有量を増加させにくいため、薄膜カラーフィルターの製造が難しいのが実情である。したがって、このような問題点を解決するための新規な色素の開発が要求されている。 In particular, when manufacturing a color filter using the pigment dispersion method, it is difficult to increase the pigment content in the photosensitive resin composition due to the pigment derivative and the dispersant added by the pigment dispersion method, so that a thin film color filter can be manufactured. The reality is that it is difficult. Therefore, the development of a new dye for solving such a problem is required.
本発明は、上記課題を解決するために、色再現性、色特性、耐熱性、溶解度などに優れて、カラーフィルター用色材として用いられる新規な構造の着色剤化合物およびこれを含む着色組成物を提供することを目的とする。 In order to solve the above problems, the present invention provides a colorant compound having a novel structure which is excellent in color reproducibility, color characteristics, heat resistance, solubility and the like and is used as a color material for a color filter, and a coloring composition containing the same. The purpose is to provide.
上記課題を解決するために、本発明の一実施形態は、下記化学式１で表される着色剤化合物を提供する。
[化学式１]
Ｒ１〜Ｒ５は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数６〜２０の芳香族環が１以上結合したＮ−アルキレン−ピペリジンジオン（ｐｉｐｅｒｉｄｉｎｅ ｄｉｏｎｅ）、またはＮ−アルキレン−ピロリジンジオン（ｐｙｒｒｏｌｉｄｉｎｅ ｄｉｏｎｅ）であり；
Ｒ６は、下記化学式２または３であり；
Ｒ７〜Ｒ１０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり；
[化学式２]
Ｒ１１〜Ｒ２０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり、
Ｒ７〜Ｒ２０のうちの１つ以上は、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基である。
In order to solve the above problems, one embodiment of the present invention provides a colorant compound represented by the following chemical formula 1.
[Chemical formula 1]
R 1 to R 5 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, N-alkylene-piperidine dione having one or more aromatic rings having 6 to 20 carbon atoms, or N, respectively. -Alkylene-pyrrolidine dione;
R 6 is the following chemical formula 2 or 3;
R 7 to R 10 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms;
[Chemical formula 2]
R 11 to R 20 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms.
One or more of R 7 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or a carbon number of carbon atoms. 1 to 30 alkoxy groups.
本発明の他の一実施形態は、前記着色剤化合物を含む着色組成物を提供する。 Another embodiment of the present invention provides a coloring composition containing the colorant compound.
本発明のまた他の一実施形態は、前記着色組成物を含むカラーフィルターを提供する。 Yet another embodiment of the present invention provides a color filter containing the coloring composition.
本発明のまた他の一実施形態は、前記カラーフィルターを含むディスプレイ装置を提供する。 Yet another embodiment of the present invention provides a display device that includes the color filter.
本発明の着色剤化合物は、今までに知られていない新規な構造の化合物であって、特定グループ（ｍｏｉｅｔｙ）を含み、安定した色再現性、優れた耐熱性および溶解度を示すことができる。また、従来技術に比べて溶媒に対する溶解度に優れており、顔料分散法の使用時に顔料誘導体および分散剤の使用量を減少させることができる。 The colorant compound of the present invention is a compound having a novel structure that has not been known so far, contains a specific group (moiety), and can exhibit stable color reproducibility, excellent heat resistance, and solubility. In addition, it has excellent solubility in a solvent as compared with the prior art, and the amount of the pigment derivative and the dispersant used can be reduced when the pigment dispersion method is used.
したがって、本発明に係るカラーフィルターは、優れた色再現性および耐熱性によって色再現率が高く、輝度および明暗比が高い高解像度のカラーフィルターを提供することができる。また、新規着色剤化合物の優れた溶解度によって着色組成物中の顔料含有量を増加させることができるため、薄膜カラーフィルターの製造が可能になる。 Therefore, the color filter according to the present invention can provide a high-resolution color filter having a high color reproducibility and a high brightness and light-dark ratio due to its excellent color reproducibility and heat resistance. In addition, the excellent solubility of the novel colorant compound can increase the pigment content in the coloring composition, which makes it possible to manufacture a thin film color filter.
本発明は、多様な変更を加えることができ、様々な形態を有することができるところ、特定の実施形態を例示し、以下で詳細に説明する。しかし、これは本発明を特定の実施形態に対して限定するものではなく、本発明の思想および技術範囲に含まれる全ての変更、均等物または代替物を含むものと理解しなければならない。 The present invention exemplifies specific embodiments where various modifications can be made and can have various forms, which will be described in detail below. However, this is not intended to limit the invention to any particular embodiment, but should be understood to include all modifications, equivalents or alternatives contained within the ideas and technical scope of the invention.
以下、本発明の着色剤化合物およびこれを含む着色組成物についてより詳しく説明する。 Hereinafter, the colorant compound of the present invention and the coloring composition containing the same will be described in more detail.
着色剤化合物
本発明の一実施形態による着色剤化合物は、下記化学式１で表される。
[化学式１]
Ｒ１〜Ｒ５は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数６〜２０の芳香族環が１以上結合したＮ−アルキレン−ピペリジンジオン（ｐｉｐｅｒｉｄｉｎｅ ｄｉｏｎｅ）、またはＮ−アルキレン−ピロリジンジオン（ｐｙｒｒｏｌｉｄｉｎｅ ｄｉｏｎｅ）であり；
Ｒ６は、下記化学式２または３であり；
Ｒ７〜Ｒ１０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり；
[化学式２]
Ｒ１１〜Ｒ２０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり、
Ｒ７〜Ｒ２０のうちの１つ以上は、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基である。
Colorant Compound The colorant compound according to the embodiment of the present invention is represented by the following chemical formula 1.
[Chemical formula 1]
R 1 to R 5 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, N-alkylene-piperidine dione having one or more aromatic rings having 6 to 20 carbon atoms, or N, respectively. -Alkylene-pyrrolidine dione;
R 6 is the following chemical formula 2 or 3;
R 7 to R 10 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms;
[Chemical formula 2]
R 11 to R 20 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms.
One or more of R 7 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or a carbon number of carbon atoms. 1 to 30 alkoxy groups.
一方、本明細書において、
本発明のまた他の一実施形態による着色剤化合物は、上記化学式１の着色剤化合物であって、Ｒ１、Ｒ２、Ｒ４およびＲ５は、それぞれ水素、またはハロゲンであり；前記Ｒ３は、下記化学式４の官能基または下記化学式５の官能基であり得る。
[化学式４]
[Chemical formula 4]
一方、前記'置換または非置換の'という用語は、重水素；ハロゲン基；ニトリル基；ニトロ基；ヒドロキシ基；カルボニル基；エステル基；イミド基；アミノ基；ホスフィンオキシド基；アルコキシ基；アリールオキシ基；アルキルチオキシ基；アリールチオキシ基；アルキルスルホキシ基；アリールスルホキシ基；シリル基；ホウ素基；アルキル基；シクロアルキル基；アルケニル基；アリール基；アラルキル基；アラルケニル基；アルキルアリール基；アルキルアミン基；アラルキルアミン基；ヘテロアリールアミン基；アリールアミン基；アリールホスフィン基；またはＮ、ＯおよびＳ原子のうちの１個以上を含むヘテロ環基からなる群から選択された１個以上の置換基で置換または非置換されるか、前記例示された置換基のうちの２以上の置換基が連結された置換または非置換されることを意味する。例えば、'２以上の置換基が連結された置換基'は、ビフェニル基であってもよい。すなわち、ビフェニル基は、アリール基であってもよく、２個のフェニル基が連結された置換基と解釈されてもよい。 On the other hand, the term'substituted or unsubstituted'refers to as heavy hydrogen; halogen group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryloxy. Group; Alkyltioxy Group; Arylthioxy Group; Alkylsulfoxic Group; Arylsulfoxic Group; Cyril Group; Boron Group; Alkyl Group; Cycloalkyl Group; Alkenyl Group; Alkylamine group; aralkylamine group; heteroarylamine group; arylamine group; arylphosphin group; or one or more selected from the group consisting of heterocyclic groups containing one or more of N, O and S atoms. It means that it is substituted or unsubstituted with a substituent, or that two or more of the above-exemplified substituents are linked and substituted. For example, the'substituent in which two or more substituents are linked'may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are linked.
前記アルキル基は炭素数は１〜２０、または炭素数は１〜１０、または炭素数は１〜５の直鎖もしくは分枝鎖のアルキル基であってもよい。アルキル基の具体的な例としては、メチル、エチル、プロピル、ｎ−プロピル、イソプロピル、ブチル、ｎ−ブチル、イソブチル、ｔｅｒｔ−ブチル、ｓｅｃ−ブチル、１−メチルブチル、１−エチルブチル、ペンチル、ｎ−ペンチル、イソペンチル、ネオペンチル、ｔｅｒｔ−ペンチル、ヘキシル、ｎ−ヘキシル、１−メチルペンチル、２−メチルペンチル、４−メチル−２−ペンチル、３，３−ジメチルブチル、２−エチルブチル、ヘプチル、ｎ−ヘプチル、１−メチルヘキシル、オクチル、ｎ−オクチル、ｔｅｒｔ−オクチル、１−メチルヘプチル、２−エチルヘキシル、２−プロピルペンチル、ｎ−ノニル、２，２−ジメチルヘプチル、１−エチルプロピル、１，１−ジメチルプロピル、イソヘキシル、２−メチルペンチル、４−メチルヘキシル、５−メチルヘキシルなどがあるが、これらに限定されるものではない。 The alkyl group may be a linear or branched alkyl group having 1 to 20 carbon atoms, 1 to 10 carbon atoms, or 1 to 5 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-. Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl , 1-Methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethylpropyl, 1,1- There are, but are not limited to, dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl and the like.
前記アルコキシ基は、直鎖、分枝鎖または環鎖であってもよい。アルコキシ基の炭素数は特に限定されないが、炭素数１〜３０であることが好ましい。具体的には、メトキシ、エトキシ、ｎ−プロポキシ、イソプロポキシ、ｉ−プロピルオキシ、ｎ−ブトキシ、イソブトキシ、ｔｅｒｔ−ブトキシ、ｓｅｃ−ブトキシ、ｎ−ペンチルオキシ、ネオペンチルオキシ、イソペンチルオキシ、ｎ−ヘキシルオキシ、３，３−ジメチルブチルオキシ、ｎ−オクチルオキシ、ｎ−ノニルオキシ、ｎ−メシルオキシ、ベンジルオキシ、ｐ−メチルベンジルオキシなどが挙げられるが、これらに限定されるものではない。 The alkoxy group may be a straight chain, a branched chain or a ring chain. The number of carbon atoms of the alkoxy group is not particularly limited, but it is preferably 1 to 30 carbon atoms. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n- Examples thereof include, but are not limited to, hexyloxy, 3,3-dimethylbutyloxy, n-octyloxy, n-nonyloxy, n-mesyloxy, benzyloxy and p-methylbenzyloxy.
前記アリール基は炭素数６〜３０、または炭素数６〜２０、または炭素数６〜１２の単環式アリール基または多環式アリール基であってもよい。前記単環式アリール基としては、フェニル基、ビフェニル基、ターフェニル基などであってもよいが、これらに限定されるものではない。前記多環式アリール基としては、ナフチル基、アントラセニル基、フェナントリル基、ピレニル基、ペリレニル基、クリセニル基、フルオレニル基などであってもよいが、これらに限定されるものではない。 The aryl group may be a monocyclic aryl group or a polycyclic aryl group having 6 to 30 carbon atoms, 6 to 20 carbon atoms, or 6 to 12 carbon atoms. The monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, or the like, but is not limited thereto. The polycyclic aryl group may be, but is not limited to, a naphthyl group, an anthracenyl group, a phenanthryl group, a pyrenyl group, a perylenel group, a chrysenyl group, a fluorenyl group and the like.
前記アリールアルキル基、アルキルアリール基中のアリール基は、上述したアリール基に関する説明が適用可能である。前記アリールアルキル基、アルキルアリール基中のアルキル基は、上述したアルキル基に関する説明が適用可能である。 As the arylalkyl group and the aryl group in the alkylaryl group, the above-mentioned description regarding the aryl group can be applied. As the arylalkyl group and the alkyl group in the alkylaryl group, the above-mentioned description regarding the alkyl group can be applied.
本発明のまた他の一実施形態による着色剤化合物は、上記化学式１の着色剤化合物であって、Ｒ７〜Ｒ１０のうちの１つ以上が炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）であり、前記Ｒ１１〜Ｒ２０は、それぞれ、水素、ハロゲン、または炭素数１〜１０の脂肪族基であり得る。 The colorant compound according to still another embodiment of the present invention is the colorant compound of the above chemical formula 1, wherein one or more of R 7 to R 10 is a ring or linear chain having 1 to 30 carbon atoms. It is an alkyl thio group or an aryl thio group having 1 to 30 carbon atoms, and R 11 to R 20 are hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, respectively. possible.
本発明のまた他の一実施形態による着色剤化合物は、上記化学式１の着色剤化合物であって、Ｒ７〜Ｒ１０は、それぞれ、水素、ハロゲン、または炭素数１〜１０の脂肪族基であり、前記Ｒ１１〜Ｒ１４のうちの１つ以上、またはＲ１５〜Ｒ２０のうちの１つ以上が炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）であり得る。 The colorant compound according to still another embodiment of the present invention is the colorant compound of the above chemical formula 1, wherein R 7 to R 10 are hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, respectively. Yes, one or more of the above R 11 to R 14 , or one or more of R 15 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, or carbon. It can be an arylthio group of the number 1-30.
一方、上記化学式１において、前記Ｒ７〜Ｒ２０のうちの１つ以上は、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり得、より詳しくは、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）であり得る。 On the other hand, in the above chemical formula 1, one or more of the R 7 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms (alkyl thio group) or an aryl thio group having 1 to 30 carbon atoms. It can be an aryl thio group), or an alkoxy group having 1 to 30 carbon atoms, and more particularly, it can be a ring or linear alkyl thio group having 1 to 30 carbon atoms (alkyl thio group).
一方、本発明の一実施形態によれば、前記Ｒ７〜Ｒ２０のうちの１つ以上は、炭素数３〜６の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）であり得、例えば、下記化学式１０のブチルチオ基であり得る。
[化学式１０]
[Chemical formula 10]
上述のように、上記化学式１の着色剤化合物は、キノフタロン（ｑｕｉｎｏｐｈｔｈａｌｏｎｅ）系誘導体化合物の特定位置に１つ以上の炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基が置換された構造を有することができ、より詳しくは、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）が置換された構造を有することができる。 As described above, the colorant compound of the above chemical formula 1 has one or more ring or linear alkylthio group having 1 to 30 carbon atoms, carbon at a specific position of the quinophthalone-based derivative compound. It can have a structure in which an arylthio group having a number of 1 to 30 or an alkoxy group having a carbon number of 1 to 30 is substituted, and more particularly, a ring or a linear alkylthio having a carbon number of 1 to 30. It can have a structure in which an alkyl thio group or an aryl thio group having 1 to 30 carbon atoms is substituted.
具体的には、化学式１の着色剤化合物に、上記のように１つ以上のアルキルチオ基が導入されることによって分子の平面性を減少させて、分子間のπ−π相互作用（ｉｎｔｅｒａｃｔｉｏｎ）を減少させることができる。これにより、分子が有機溶媒に容易に溶媒和（ｓｏｌｖａｔｉｏｎ）されることによって、前記着色剤化合物は、有機溶剤に対する溶解度が増加する特徴を有することができる。 Specifically, by introducing one or more alkylthio groups into the colorant compound of Chemical Formula 1 as described above, the flatness of the molecule is reduced, and the π-π interaction between the molecules is induced. Can be reduced. Thereby, the colorant compound can have a characteristic that the solubility in the organic solvent is increased by easily solvating the molecule into the organic solvent.
そのため、前記着色剤化合物は、有機溶媒（例えば、ＤＭＦ）に対する溶解度が顕著に向上するので、これを含む着色組成物を顔料分散法で製造するときに要求される顔料誘導体、分散剤使用量が顕著に減少する。したがって、前記比率ほど着色組成物中に前記着色剤化合物または顔料含有量を増加させることができるので、薄膜カラーフィルターの製造が容易になる。 Therefore, the colorant compound has a significantly improved solubility in an organic solvent (for example, DMF), so that the amount of the pigment derivative and dispersant used when producing a coloring composition containing the colorant compound by the pigment dispersion method is large. Significantly decreases. Therefore, the content of the colorant compound or the pigment in the coloring composition can be increased by the above ratio, so that the thin film color filter can be easily manufactured.
上述した着色剤化合物の具体的な例としては、下記化学式６〜４７で表される化合物が挙げられるが、本発明はこれらに限定されるものではない。
[化学式６]
[Chemical formula 6]
上記化学式１の着色剤化合物の合成方法では、通常知られている合成方法および合成装置を大きな制限なく使用することができる。例えば、化学式１の着色剤化合物は、まず、ピグメントイエローにフタルイミド（ｐｈｔｈａｌｉｍｉｄｅ）、または１，８−ナフタルイミド（１，８−Ｎａｐｈｔｈａｌｉｍｉｄｅ）を選択的に導入した後、そこにアルキルチオール（ａｌｋｙｌｔｈｉｏｌ）、例えば、１−ブタンチオール（１−ｂｕｔａｎｔｈｉｏｌ）を反応させて製造することもできる。 In the method for synthesizing the colorant compound of the above chemical formula 1, generally known synthetic methods and synthesizing devices can be used without major restrictions. For example, in the colorant compound of Chemical Formula 1, first, phthalimide or 1,8-naphthalimide is selectively introduced into pigment yellow, and then alkylthiol, For example, it can also be produced by reacting 1-butanethiol.
着色組成物
本発明の一実施形態によれば、前記着色剤化合物を含む着色組成物を提供する。
Coloring Composition According to one embodiment of the present invention, a coloring composition containing the colorant compound is provided.
本発明の一実施形態によれば、前記着色組成物は、染料（Ｄｙｅ）および顔料（Ｐｉｇｍｅｎｔ）のうちの少なくとも１つをさらに含むことができるが、このとき、前記染料および顔料は、それぞれ黄色、赤色および緑色から選択されるいずれか１つの色を示す化合物を１種以上含むことができる。 According to one embodiment of the present invention, the coloring composition may further contain at least one of a dye (Dye) and a pigment (Pigment), at which time the dye and the pigment are yellow, respectively. , Red and green can contain one or more compounds exhibiting any one color.
本発明の一実施形態によれば、前記黄色を示す化合物は、金属−複合体（ｍｅｔａｌ−ｃｏｍｐｌｅｘ）系化合物、アゾ（ａｚｏ）系化合物、キノフタロン（ｑｕｉｎｏｐｈｔｈａｌｏｎｅ）系化合物、イソインドリン（ｉｓｏｉｎｄｏｌｉｎｅ）系化合物、およびスチリル（Ｓｔｙｒｙｌ）系化合物を含む群から選択される１種以上の化合物を含むことができる。 According to one embodiment of the present invention, the yellow compound is a metal-complex-based compound, an azo-based compound, a quinophthalone-based compound, or an isoindoline-based compound. , And one or more compounds selected from the group comprising Styryl compounds.
本発明のまた他の一実施形態によれば、前記赤色を示す化合物は、金属−複合体（ｍｅｔａｌ−ｃｏｍｐｌｅｘ）系化合物、アゾ（ａｚｏ）系化合物、キサンテン（ｘａｎｔｈｅｎｅ）系化合物、ジケトピロロピロール（ｄｉｋｅｔｏｐｙｒｒｏｌｏｐｙｒｒｏｌｅ）系化合物、アントラキノン（ａｎｔｈｒａｑｕｉｎｏｎｅ）系化合物、およびペリレン（Ｐｅｒｙｌｅｎｅ）系化合物を含む群から選択される１種以上の化合物を含むことができる。 According to yet another embodiment of the present invention, the red-colored compound is a metal-complex-based compound, an azo-based compound, a xanthene-based compound, or diketopyrrolopyrrole. It can contain one or more compounds selected from the group containing (diketopyrrolopyrolole) -based compounds, anthraquinone-based compounds, and perylene-based compounds.
本発明のまた他の一実施形態によれば、前記緑色を示す化合物は、金属−複合体（ｍｅｔａｌ−ｃｏｍｐｌｅｘ）系化合物、トリアリールメタン（ｔｒｉａｒｙｌｍｅｔｈａｎｅ）系化合物、アントラキノン（ａｎｔｈｒａｑｕｉｎｏｎｅ）系化合物を含む群から選択される１種以上の化合物を含むことができる。 According to yet another embodiment of the present invention, the green compound includes a metal-complex-based compound, a triarylmethane-based compound, and an anthraquinone-based compound. It can contain one or more compounds selected from.
一方、本発明の一実施形態によれば、前記顔料としては、ＰＹ１２９、ＰＹ１３８、ＰＹ１３９、ＰＹ１５０、およびＰＹ１８５を含む黄色顔料群；ＰＲ４８、ＰＲ４８：１、ＰＲ４８：２、ＰＲ４８：３、ＰＲ４８：４、ＰＲ１７７、ＰＲ１７９、ＰＲ２０７、ＰＲ２５４、ＰＲ２５５、ＰＲ２６４、およびＰＲ２６９を含む赤色顔料群；およびＰＧ７、ＰＧ３６、ＰＧ５８、およびＰＧ５９を含む緑色顔料群；から選択される少なくとも１種を含むことができる。 On the other hand, according to one embodiment of the present invention, the pigments include a group of yellow pigments including PY129, PY138, PY139, PY150, and PY185; PR48, PR48: 1, PR48: 2, PR48: 3, PR48: 4. , PR177, PR179, PR207, PR254, PR255, PR264, and PR269; and a group of green pigments including PG7, PG36, PG58, and PG59;
本発明の一実施形態による着色組成物は、前記着色剤化合物以外に、バインダー樹脂、多官能性モノマー、光開始剤および溶媒をさらに含むことができる。 The coloring composition according to one embodiment of the present invention may further contain a binder resin, a polyfunctional monomer, a photoinitiator and a solvent in addition to the coloring agent compound.
着色剤化合物に対する詳細な説明および具体的な例は上述のとおりであり、着色組成物中の前記着色剤化合物は、前記着色組成物１００重量部に対して、２０重量部以上、好ましくは２５重量部以上含むことができ、５０重量部以下、好ましくは４０重量部以下含むことができる。 Detailed explanations and specific examples of the colorant compound are as described above, and the colorant compound in the coloring composition is 20 parts by weight or more, preferably 25 parts by weight, based on 100 parts by weight of the coloring composition. It can contain more than 50 parts by weight, preferably 50 parts by weight or less, preferably 40 parts by weight or less.
前記着色剤化合物の含有量が、このような範囲未満であれば、ディープカラー（Ｄｅｅｐ ｃｏｌｏｒ）の実現が難しく、このような範囲を超えれば樹脂組成物の硬化反応がうまく起こらないこともあり、このような範囲内に含まれることが好適である。 If the content of the colorant compound is less than such a range, it is difficult to realize a deep color, and if it exceeds such a range, the curing reaction of the resin composition may not occur well. It is preferable that it is included in such a range.
一方、前記着色組成物１００重量部は、前記着色組成物に含まれる着色剤化合物、バインダー樹脂、多官能性モノマーおよび光開始剤を全て合わせたものを１００重量部とし、後述のように溶媒をさらに含む場合、上述した成分を含む固形分（ｓｏｌｉｄ ｃｏｎｔｅｎｔｓ）１００重量部を基準とする。 On the other hand, 100 parts by weight of the coloring composition is 100 parts by weight of the colorant compound, the binder resin, the polyfunctional monomer and the photoinitiator contained in the coloring composition, and the solvent is used as described later. When it is further contained, 100 parts by weight of solid components containing the above-mentioned components is used as a reference.
一方、本発明の一実施形態による着色組成物において、上記化学式１の着色剤化合物は、単独または２種以上を混合して使用することができる。また、本発明の一実施形態による着色組成物は、必要に応じて、上記化学式１の着色剤化合物に加えて、他の公知の着色剤を任意にさらに含むこともできる。 On the other hand, in the coloring composition according to one embodiment of the present invention, the coloring agent compound of the above chemical formula 1 can be used alone or in combination of two or more. Further, the coloring composition according to the embodiment of the present invention may optionally further contain other known coloring agents in addition to the coloring agent compound of the above chemical formula 1, if necessary.
一方、前記着色組成物を公知の着色剤と一緒に混合して使用する場合、顔料の再凝集を防止するか、または異物の生成を防止する効果をさらに得ることができるので、上記のような形態でカラーフィルターに適用時、明暗比が向上する追加の効果を得ることができる。 On the other hand, when the coloring composition is mixed with a known colorant and used, the effect of preventing the reaggregation of the pigment or the formation of foreign substances can be further obtained. When applied to a color filter in the form, an additional effect of improving the light-dark ratio can be obtained.
前記バインダー樹脂としては特に制限されず、本発明が属する技術分野で一般的に知られているものを使用することができ、好ましくは、アルカリ可溶性樹脂を使用することができる。 The binder resin is not particularly limited, and those generally known in the technical field to which the present invention belongs can be used, and an alkali-soluble resin can be preferably used.
具体的には、アルカリ可溶性樹脂として（メト）アクリル系樹脂、アクリルアミド系樹脂、ノボラック系樹脂などを使用することができ、好ましくは、重量平均分子量（Ｍｗ）が３，０００〜１５０，０００ｇ／ｍｏｌであることを使用することができるが、本発明はこれに限定されるものではない。一方、前記重量平均分子量は、ポリスチレンを標準物質として用いてＧＰＣ（Ｇｅｌ Ｐｅｒｍｅａｔｉｏｎ Ｃｈｒｏｍａｔｏｇｒａｐｈｙ）で測定したのである。 Specifically, (meth) acrylic resin, acrylamide resin, novolak resin and the like can be used as the alkali-soluble resin, and the weight average molecular weight (Mw) is preferably 3,000 to 150,000 g / mol. However, the present invention is not limited thereto. On the other hand, the weight average molecular weight was measured by GPC (Gel Permeation Chromatography) using polystyrene as a standard substance.
一方、前記着色組成物中の前記バインダー樹脂は、前記着色組成物１００重量部に対して、３重量部以上、好ましくは５重量部以上、より好ましくは１０重量部以上含むことができ、３０重量部以下、好ましくは２０重量部以下、より好ましくは１５重量部以下含むことができる。 On the other hand, the binder resin in the coloring composition can contain 3 parts by weight or more, preferably 5 parts by weight or more, more preferably 10 parts by weight or more, and 30 parts by weight, based on 100 parts by weight of the coloring composition. It can contain parts or less, preferably 20 parts by weight or less, and more preferably 15 parts by weight or less.
前記多官能性モノマーは、特に制限されず、本発明の技術分野で公知のものを使用することができ、前記多官能性モノマーは、光によりフォトレジスト像を形成する役割を果たすモノマーであり、具体的には、プロピレングリコールメタクリレート、ジペンタエリスリトールヘキサアクリレート、ジペンタエリスリトールアクリレート、ネオペンチルグリコールジアクリレート、６−ヘキサンジオールジアクリレート、１，６−ヘキサンジオールアクリレートテトラエチレングリコールメタクリレート、ビスフェノキシエチルアルコールジアクリレート、トリスヒドロキシエチルイソシアヌレートトリメタクリレート、トリメチルプロパントリメタクリレート、ジフェニルペンタエリスリトールヘキサアクリレート、ペンタエリスリトールトリメタクリレート、ペンタエリスリトールテトラメタクリレートおよびジペンタエリスリトールヘキサメタクリレートからなる群から選択される１種または２種以上の混合物であってもよい。 The polyfunctional monomer is not particularly limited, and those known in the technical field of the present invention can be used. The polyfunctional monomer is a monomer that plays a role of forming a photoresist image by light. Specifically, propylene glycol methacrylate, dipentaerythritol hexaacrylate, dipentaerythritol acrylate, neopentyl glycol diacrylate, 6-hexanediol diacrylate, 1,6-hexanediol acrylate tetraethylene glycol methacrylate, bisphenoxyethyl alcohol di. One or more selected from the group consisting of acrylate, trishydroxyethyl isocyanurate trimethacrylate, trimethylpropane trimethacrylate, diphenylpentaerythritol hexaacrylate, pentaerythritol trimethacrylate, pentaerythritol tetramethacrylate and dipentaerythritol hexamethacrylate. It may be a mixture.
前記着色組成物中の前記多官能性モノマーは、前記着色組成物１００重量部に対して、３０重量部以上、好ましくは４０重量部以上、より好ましくは５０重量部以上含むことができ、８０重量部以下、好ましくは７０重量部以下、より好ましくは６０重量部以下含むことができる。 The polyfunctional monomer in the coloring composition can contain 30 parts by weight or more, preferably 40 parts by weight or more, more preferably 50 parts by weight or more, and 80 parts by weight, based on 100 parts by weight of the coloring composition. It can contain parts or less, preferably 70 parts by weight or less, and more preferably 60 parts by weight or less.
前記光開始剤としては、２，４−トリクロロメチル−（４'−メトキシフェニル）−６−トリアジン、２，４−トリクロロメチル−（４'−メトキシスチリル）−６−トリアジン、２，４−トリクロロメチル−（フィプロニル）６−トリアジン、１−ヒドロキシシクロヘキシルフェニルケトン、４−（２−ヒドロキシエトキシ）−フェニル（２−ヒドロキシ）プロピルケトン、ベンゾフェノン、２，４，６−トリメチルアミノベンゾフェノンからなる群から選択される１種以上の化合物を使用することができるが、これらだけに限定されるものではない。 Examples of the photoinitiator include 2,4-trichloromethyl- (4'-methoxyphenyl) -6-triazine, 2,4-trichloromethyl- (4'-methoxystyryl) -6-triazine, and 2,4-trichloro. Select from the group consisting of methyl- (fipronyl) 6-triazine, 1-hydroxycyclohexylphenylketone, 4- (2-hydroxyethoxy) -phenyl (2-hydroxy) propylketone, benzophenone, 2,4,6-trimethylaminobenzophenone. One or more compounds can be used, but the invention is not limited thereto.
前記着色組成物中の前記光重合開始剤は、前記着色組成物１００重量部に対して、０．１〜１０重量部で含まれる。 The photopolymerization initiator in the coloring composition is contained in an amount of 0.1 to 10 parts by weight with respect to 100 parts by weight of the coloring composition.
一方、本発明の一実施形態による着色組成物は、塗布性および作業性を高めるために溶媒をさらに含むことができる。 On the other hand, the coloring composition according to one embodiment of the present invention may further contain a solvent in order to improve coatability and workability.
本発明の一実施形態によれば、前記溶媒としては、メチルエチルケトン、メチルセロソルブ、エチルセロソルブ、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールメチルエチルエーテル、２−エトキシプロパノール、２−メトキシプロパノール、３−メトキシブタノール、シクロヘキサノン、シクロペンタノン、プロピレングリコールメチルエーテルアセテート、プロピレングリコールエチルエーテルアセテート、３−メトキシブチルアセテート、エチル３−エトキシプロピオネート、エチルセロソルブアセテート、メチルセロソルブアセテート、ブチルアセテート、またはジプロピレングリコールモノメチルエーテルからなる群から選択される１種以上の化合物を使用することができるが、これらだけに限定されるものではない。 According to one embodiment of the present invention, the solvent includes methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol methyl. Ethylene ether, 2-ethoxypropanol, 2-methoxypropanol, 3-methoxybutanol, cyclohexanone, cyclopentanone, propylene glycol methyl ether acetate, propylene glycol ethyl ether acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate, One or more compounds selected from the group consisting of ethyl cellosolve acetate, methyl cellosolve acetate, butyl acetate, or dipropylene glycol monomethyl ether can be used, but is not limited thereto.
前記溶媒の含有量は、塗布性および作業性を考慮して調節することができるので、特に制限されないが、例えば、前記着色組成物１００重量部に対して、５０〜５００重量部で含まれる。 The content of the solvent can be adjusted in consideration of coatability and workability, and is not particularly limited. For example, the content of the solvent is 50 to 500 parts by weight with respect to 100 parts by weight of the coloring composition.
本発明の一実施形態によれば、前記着色組成物は、上述した成分に加えて、硬化促進剤、熱重合抑制剤、分散剤、酸化防止剤、紫外線吸収剤、レベリング剤、光増感剤、可塑剤、接着促進剤、充填剤、または界面活性剤などの従来カラーフィルター用着色組成物に含まれ得る添加剤をさらに含むことができる。 According to one embodiment of the present invention, in addition to the above-mentioned components, the coloring composition includes a curing accelerator, a thermal polymerization inhibitor, a dispersant, an antioxidant, an ultraviolet absorber, a leveling agent, and a photosensitizer. , Plasticizers, Adhesion Accelerators, Fillers, or Surfactants, which may further include additives that may be included in conventional color filters for color filters.
前記硬化促進剤としては、例えば、２−メルカプトベンゾイミダゾール、２−メルカプトベンゾチアゾール、２−メルカプトベンゾオキサゾール、２，５−ジメルカプト−１，３，４−チアジアゾール、２−メルカプト−４，６−ジメチルアミノピリジン、ペンタエリスリトールテトラキス（３−メルカプトプロピオネート）、ペンタエリスリトールトリス（３−メルカプトプロピオネート）、ペンタエリスリトールテトラキス（２−メルカプトアセテート）、ペンタエリスリトールトリス（２−メルカプトアセテート）、トリメチロールプロパントリス（２−メルカプトアセテート）、トリメチロールプロパントリス（３−メルカプトプロピオネート）、トリメチロールエタントリス（２−メルカプトアセテート）、およびトリメチロールエタントリス（３−メルカプトプロピオネート）からなる群から選択される１種以上を含むことができるが、これらだけに限定されるものではなく、本発明が属する技術分野で一般的に知られているものを含むことができる。 Examples of the curing accelerator include 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5-dimercapto-1,3,4-thiadiazol, 2-mercapto-4,6-dimethyl. Aminopyridine, pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tris (2-mercaptoacetate), trimethylolpropane Select from the group consisting of Tris (2-mercaptoacetate), Trimethylolpropanetris (3-mercaptopropionate), Trimethylolethanetris (2-mercaptoacetate), and Trimethylolethanetris (3-mercaptopropionate). However, it is not limited to these, and can include those generally known in the technical field to which the present invention belongs.
一方、本発明の一実施形態による着色組成物は、本発明が属する技術分野で一般的に知られている方法、例えば印刷法、またはフォトリソグラフィ法によりカラーフィルターを製造するのに使用することができる。 On the other hand, the coloring composition according to one embodiment of the present invention can be used for producing a color filter by a method generally known in the technical field to which the present invention belongs, for example, a printing method or a photolithography method. it can.
例えば、フォトリソグラフィ法によれば、前記着色組成物を透明基板上にスプレーコーティング、スピンコーティング、スリットコーティング、ロールコーティング、浸漬などの方法によって塗布する。塗布膜に所定のパターンを有するマスクを通して選択的に露光（ｅｘｐｏｓｕｒｅ）工程を行う。一方、前記露光前の熱処理（ｐｒｅ ｂａｋｅ）および／または露光後の熱処理（ｐｏｓｔ ｂａｋｅ）工程をさらに行うこともできる。露光後に前記着色組成物を現像（ｄｅｖｅｌｏｐｍｅｎｔ）して、所望のフォトレジストパターンを形成する。現像した基板を洗浄し、乾燥して、目的とする形態のフォトレジストパターンが形成されたカラーフィルターを収得することができる。一方、前記収得したカラーフィルターは、ディスプレイ装置などに活用可能である。 For example, according to a photolithography method, the coloring composition is applied onto a transparent substrate by a method such as spray coating, spin coating, slit coating, roll coating, or dipping. The exposure step is selectively performed through a mask having a predetermined pattern on the coating film. On the other hand, the pre-exposure heat treatment (pre-bake) and / or post-exposure heat treatment (post-bake) step can be further performed. After exposure, the coloring composition is developed to form a desired photoresist pattern. The developed substrate can be washed and dried to obtain a color filter on which a photoresist pattern of a desired form is formed. On the other hand, the obtained color filter can be used for a display device or the like.
以上、上述したように、本発明の着色剤化合物は、従来知られていない新規な構造の化合物であり、特定グループ（ｍｏｉｅｔｙ）を含み、安定した色再現性、優れた耐熱性および溶解度を示すことができる。また、従来技術に比べて溶媒に対する溶解度に優れていて、顔料分散法の使用時に顔料誘導体および分散剤の使用量を減少させることができる。 As described above, the colorant compound of the present invention is a compound having a novel structure that has not been known in the past, contains a specific group (moiety), and exhibits stable color reproducibility, excellent heat resistance, and solubility. be able to. In addition, it has excellent solubility in a solvent as compared with the prior art, and the amount of the pigment derivative and the dispersant used can be reduced when the pigment dispersion method is used.
したがって、本発明に係るカラーフィルターは、優れた色再現性および耐熱性により色再現率が高く、輝度および明暗比が高い高解像度のカラーフィルターを提供することができる。また、新規な着色剤化合物の優れた溶解度により着色組成物中の顔料含有量を増加させることができるので、薄膜カラーフィルターの製造が可能となる。
［発明を実施するための形態］
Therefore, the color filter according to the present invention can provide a high-resolution color filter having a high color reproducibility and a high brightness and light-dark ratio due to its excellent color reproducibility and heat resistance. Further, since the pigment content in the coloring composition can be increased due to the excellent solubility of the novel colorant compound, a thin film color filter can be manufactured.
[Mode for carrying out the invention]
以下、本発明の具体的な実施形態を通して、発明の作用および効果をより詳しく説明する。ただし、これらの実施形態は、発明の例として提示したものであり、これにより発明の権利範囲が決まるわけではない。 Hereinafter, the actions and effects of the invention will be described in more detail through specific embodiments of the present invention. However, these embodiments are presented as examples of the invention, and the scope of rights of the invention is not determined by this.
製造例１：化合物１の合成
そこに１００ｇのピグメントイエロー１３８（ＢＡＳＦ社製）を添加した後、該混合物を１００℃で加熱し、３時間攪拌した。次いで、前記混合物に水３５００ｇを添加し、６０℃で３０分間攪拌した。このようにして沈殿した生成物をろ過し、中性になるように水で洗浄した後、真空乾燥旋盤内で９０℃で乾燥して化合物（Ａ）を得た。 After adding 100 g of Pigment Yellow 138 (manufactured by BASF), the mixture was heated at 100 ° C. and stirred for 3 hours. Then, 3500 g of water was added to the mixture, and the mixture was stirred at 60 ° C. for 30 minutes. The product thus precipitated was filtered, washed with water to neutralize, and then dried in a vacuum drying lathe at 90 ° C. to give compound (A).
次に、５００ｍｌ １−ｎｅｃｋ ＲＢＦに前記化合物（Ａ）３ｇ（３．４１７ｍｍｏｌ）、１−Ｂｕｔａｎｔｈｉｏｌ ０．５２ｇ（７．０３３ｍｍｏｌ）、Ｋ２ＣＯ３１．９４ｇ（１４．０６ｍｍｏｌ）を入れ、６０℃で２４時間攪拌した。反応溶液を常温に冷却した後、減圧下でろ過させた。減圧下で溶媒を除去し、カラムで精製して、前記化合物１を得た。ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物１の分子量９０７を確認した。 Next, 3 g (3.417 mmol) of the compound (A), 0.52 g (7.033 mmol) of 1-Butanthiol, and 1.94 g (14.06 mmol) of K 2 CO 3 were added to 500 ml 1-neck RBF, and the temperature was 60 ° C. Was stirred for 24 hours. The reaction solution was cooled to room temperature and then filtered under reduced pressure. The solvent was removed under reduced pressure and purified on a column to obtain the above compound 1. As a result of analysis of APCI negative MS, the molecular weight of Compound 1 was confirmed to be 907.
製造例２：化合物２の合成
次に、５００ｍｌ １−ｎｅｃｋ ＲＢＦに前記化合物（Ｂ）３ｇ（３．３２ｍｍｏｌ）、１−Ｂｕｔａｎｔｈｉｏｌ ０．４９ｇ（６．６５ｍｍｏｌ）、Ｋ２ＣＯ３ １．８３ｇ（１３．２８ｍｍｏｌ）を入れ、６０℃で２４時間攪拌した。反応溶液を常温に冷却した後、減圧下でろ過させた。減圧下で溶媒を除去し、カラムで精製して、前記化合物２を得た。ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物２の分子量９５７を確認した。 Next, 3 g (3.32 mmol) of the compound (B), 0.49 g (6.65 mmol) of 1-Butanthiol, and 1.83 g (13.28 mmol) of K 2 CO 3 were added to 500 ml 1-neck RBF, and the temperature was 60 ° C. Was stirred for 24 hours. The reaction solution was cooled to room temperature and then filtered under reduced pressure. The solvent was removed under reduced pressure and purified on a column to obtain the compound 2. As a result of analysis of APCI negative MS, the molecular weight of Compound 2 was confirmed to be 957.
製造例３：化合物３の合成
次に、５００ｍｌ １−ｎｅｃｋ ＲＢＦに前記化合物（Ｄ）３ｇ（３．９２ｍｍｏｌ）、１−Ｂｕｔａｎｔｈｉｏｌ ０．５８ｇ（７．８４ｍｍｏｌ）、Ｋ２ＣＯ３ ２．１７ｇ（１５．６９ｍｍｏｌ）を入れ、６０℃で２４時間攪拌した。反応溶液を常温に冷却した後、減圧下でろ過させた。減圧下で溶媒を除去し、カラムで精製して、前記化合物３を得た。ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物３の分子量８１９を確認した。 Then, 500ml 1-neck RBF in the compound (D) 3g (3.92mmol), 1-Butanthiol 0.58g (7.84mmol), K 2 CO 3 placed 2.17g (15.69mmol), 60 ℃ Was stirred for 24 hours. The reaction solution was cooled to room temperature and then filtered under reduced pressure. The solvent was removed under reduced pressure and purified on a column to obtain the above compound 3. As a result of analysis of APCI negative MS, the molecular weight of Compound 3 was confirmed to be 819.
製造例４：化合物４の合成
次に、５００ｍｌ １−ｎｅｃｋ ＲＢＦに前記化合物（Ｅ）３ｇ（３．６８ｍｍｏｌ）、１−Ｂｕｔａｎｔｈｉｏｌ ０．５４ｇ（７．３６ｍｍｏｌ）、Ｋ２ＣＯ３ ２．０３ｇ（１４．７２ｍｍｏｌ）を入れ、６０℃で２４時間攪拌した。反応溶液を常温に冷却した後、減圧下でろ過させた。減圧下で溶媒を除去し、カラムで精製して、前記化合物４を得た。ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物４の分子量８６９を確認した。 Then, 500ml 1-neck RBF in the compound (E) 3g (3.68mmol), 1-Butanthiol 0.54g (7.36mmol), K 2 CO 3 placed 2.03g (14.72mmol), 60 ℃ Was stirred for 24 hours. The reaction solution was cooled to room temperature and then filtered under reduced pressure. The solvent was removed under reduced pressure and purified on a column to obtain the above compound 4. As a result of analysis of APCI negative MS, the molecular weight of Compound 4 was confirmed to be 869.
製造例５：化合物５の合成
ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物５の分子量７５３を確認した。 As a result of analysis of APCI negative MS, the molecular weight of Compound 5 was confirmed to be 753.
製造例６：化合物６の合成
ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物６の分子量８０３を確認した。 As a result of analysis of APCI negative MS, the molecular weight of compound 6 was confirmed to be 803.
製造例７：化合物７の合成
ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物７の分子量８０３を確認した。 As a result of analysis of APCI negative MS, the molecular weight of compound 7 was confirmed to be 803.
製造例８：化合物８の合成
ＡＰＣＩ ｎｅｇａｔｉｖｅ ＭＳの分析結果、化合物７の分子量８５３を確認した。 As a result of analysis of APCI negative MS, the molecular weight of Compound 7 was confirmed to be 853.
製造例９：化合物９の合成
製造例１０：化合物１０の合成
製造例１１：化合物１１の合成
比較製造例
一般的に感光性樹脂組成物に色材として使用されるピグメントイエロー（ｙｅｌｌｏｗ）１３８（ＢＡＳＦ社製）を用意した。
実験１：溶解度評価
前記製造例１〜１１および比較製造例による化合物を用意し、これをジメチルホルムアミド（ＤＭＦ）１００ｇに対する溶解度を測定し、その結果を下記表１に示す。具体的には、溶解度が１％以上の場合はＯ、１％未満の場合はＸと表示した。
実施例１
前記製造例１により合成された化合物１を５．５５４ｇ、バインダー樹脂としてはベンジルメタクリレートとメタクリル酸の共重合体（モル比７０：３０、酸価は１１３ ＫＯＨ ｍｇ／ｇ、ＧＰＣで測定した重量平均分子量２０，０００）、分子量分布（ＰＤＩ）２．０ｇ、固形分（Ｓ．Ｃ）２５％、溶媒ＰＧＭＥＡ含み）１０．３７６ｇ、光開始剤としてはＩ−３６９（ＢＡＳＦ社製）２．０１８ｇ、光重合性化合物としてＤＰＨＡ（日本化薬社製）１２．４４３ｇ、溶剤ＰＧＭＥＡ（ポリプロピレングリコールモノメチルエーテルアセテート）６８．５９３ｇ、および添加剤としてＦ−４７５（ＤＩＣ社製）１．０１６ｇを混合して、感光性樹脂組成物を製造した。
Example 1
5.554 g of Compound 1 synthesized according to Production Example 1, a copolymer of benzyl methacrylate and methacrylic acid as a binder resin (molar ratio 70:30, acid value 113 KOH mg / g, weight average measured by GPC). Molecular weight 20,000), molecular weight distribution (PDI) 2.0 g, solid content (SC) 25%, solvent PGMEA included) 10.376 g, photoinitiator I-369 (manufactured by BASF) 2.018 g, DPHA (manufactured by Nippon Kayaku Co., Ltd.) 12.443 g as a photopolymerizable compound, solvent PGMEA (polypropylene glycol monomethyl ether acetate) 68.593 g, and F-475 (manufactured by DIC) 1.016 g as an additive were mixed. A photosensitive resin composition was produced.
実施例２
前記製造例２により合成された化合物２を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 2
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 2 synthesized in Production Example 2 was used.
実施例３
前記製造例３により合成された化合物３を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 3
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 3 synthesized in Production Example 3 was used.
実施例４
前記製造例４により合成された化合物４を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 4
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 4 synthesized in Production Example 4 was used.
実施例５
前記製造例５により合成された化合物５を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 5
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 5 synthesized in Production Example 5 was used.
実施例６
前記製造例６により合成された化合物６を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 6
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 6 synthesized in Production Example 6 was used.
実施例７
前記製造例７により合成された化合物７を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 7
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 7 synthesized in Production Example 7 was used.
実施例８
前記製造例８により合成された化合物８を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 8
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 8 synthesized in Production Example 8 was used.
実施例９
前記製造例９により合成された化合物９を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 9
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 9 synthesized in Production Example 9 was used.
実施例１０
前記製造例１０により合成された化合物１０を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 10
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 10 synthesized in Production Example 10 was used.
実施例１１
前記製造例１１により合成された化合物１１を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Example 11
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound 11 synthesized in Production Example 11 was used.
比較例１
前記比較製造例の化合物を使用したことを除いては、前記実施例１と同様の方法で、感光性樹脂組成物を製造した。
Comparative Example 1
A photosensitive resin composition was produced in the same manner as in Example 1 except that the compound of the Comparative Production Example was used.
基板製作
前記実施例１〜１１および比較例１による感光性樹脂組成物を、基板製作にそれぞれ使用した。具体的には、前記実施例および比較例による感光性樹脂組成物をガラス（５ｘ５ｃｍ）上にスピンコート（ｓｐｉｎｃｏａｔｉｎｇ）し、１００℃で１００秒間前熱処理（ｐｒｅｂａｋｅ）を施してフィルムを形成した。
Substrate Production The photosensitive resin compositions according to Examples 1 to 11 and Comparative Example 1 were used for substrate production, respectively. Specifically, the photosensitive resin compositions according to the above Examples and Comparative Examples were spin coated on glass (5x5 cm) and preheated at 100 ° C. for 100 seconds to form a film.
フィルムを形成した基板とフォトマスク（ｐｈｏｔｏ ｍａｓｋ）との間隔を２５０ｕｍとし、露光機を用いて基板の全面に４０ｍＪ／ｃｍ２の露光量を照射した。その後、露光した基板を現像液（ＫＯＨ、０．０５％）で６０秒間現像し、２３０℃で２０分間後熱処理（ｐｏｓｔｂａｋｅ）を施して基板を製作した。 The distance between the substrate on which the film was formed and the photomask (photomask) was set to 250 um, and the entire surface of the substrate was irradiated with an exposure amount of 40 mJ / cm 2 using an exposure machine. Then, the exposed substrate was developed with a developing solution (KOH, 0.05%) for 60 seconds, and then subjected to post-heat treatment (postbake) at 230 ° C. for 20 minutes to prepare a substrate.
実験２：耐熱性評価
前記基板製作方法により製作された基板を分光器（ＭＣＰＤ−大塚電子社製）を用いて、３８０ｎｍ〜７８０ｎｍ範囲の可視光領域の透過率スペクトルを得た。また、前熱処理（ｐｒｅｂａｋｅ）基板を追加的に２３０℃で２０分間後熱処理（ｐｏｓｔｂａｋｅ）を施して、同じ装備と測定範囲で透過率スペクトルを得た。
Experiment 2: Heat resistance evaluation A transmittance spectrum in the visible light region in the range of 380 nm to 780 nm was obtained using a spectroscope (MCPD-manufactured by Otsuka Electronics Co., Ltd.) on the substrate manufactured by the above substrate manufacturing method. Further, the preheat-treated (prebake) substrate was additionally subjected to post-heat treatment (postbake) at 230 ° C. for 20 minutes to obtain a transmittance spectrum with the same equipment and measurement range.
得られた透過率スペクトルとＣ光源バックライトを用い、得られた値Ｅ（Ｌ＊、ａ＊、ｂ＊）を用いて色変化（以下、ΔＥａｂ）を計算し、下記表２に示す。 Using the obtained transmittance spectrum and the C light source backlight, the color change (hereinafter, ΔEab) is calculated using the obtained values E (L *, a *, b *), and is shown in Table 2 below.
具体的には、ΔＥａｂを計算する式は以下の通りである。
ΔＥ（Ｌ＊、ａ＊、ｂ＊）＝{（ΔＬ＊）２＋（Δａ＊）２＋（Δｂ＊）２}１／２
上記式において、ΔＥ値が小さいということは、色耐熱性に優れていることを意味し、一般的にΔＥａｂ＜３の値を有すると、耐熱性に優れた色材であると言われる。
ΔE (L *, a *, b *) = {(ΔL *) 2+ (Δa *) 2+ (Δb *) 2} 1/2
In the above formula, a small ΔE value means that the color heat resistance is excellent, and generally, a color material having a value of ΔEab <3 is said to be a color material having excellent heat resistance.
上記表２で、比較例１の着色剤化合物は、色変化（ΔＥａｂ）が０．２９と小さい商用材料であることが確認された。さらに、実施例１〜１１に適用された各着色剤化合物も色変化（ΔＥａｂ）が３より小さく、比較例１の着色剤化合物と類似した水準までも到達できるほど色耐熱性に優れており、したがって、カラーフィルター用色素として使用可能であることが確認された。 In Table 2 above, it was confirmed that the colorant compound of Comparative Example 1 was a commercial material having a small color change (ΔEab) of 0.29. Further, each of the colorant compounds applied to Examples 1 to 11 also has a color change (ΔEab) smaller than 3, and is excellent in color heat resistance so that it can reach a level similar to that of the colorant compound of Comparative Example 1. Therefore, it was confirmed that it can be used as a dye for a color filter.
実験３：コントラスト評価
下記表３に示す構成成分および組成比率（単位：ｇ）で混合して、実施例１２〜２２および、比較例２の感光性樹脂組成物を製造した。前記製造した感光性樹脂組成物を用いて、上述した基板製作方法により基板を製作した。
Experiment 3: Contrast evaluation The photosensitive resin compositions of Examples 12 to 22 and Comparative Example 2 were produced by mixing the constituent components and composition ratios (unit: g) shown in Table 3 below. A substrate was produced by the above-mentioned substrate production method using the produced photosensitive resin composition.
このように製作された基板をコントラスト測定器（壺坂電機社製）を用いて、基板の上下の偏光板が平行および直交のときの輝度を測定し、以下の計算式でコントラスト比を計算した。 Using a contrast measuring device (manufactured by Tsubosaka Electric Co., Ltd.), the brightness of the substrate manufactured in this way was measured when the upper and lower polarizing plates of the substrate were parallel and orthogonal, and the contrast ratio was calculated by the following formula. ..
コントラスト（Ｃｏｎｔｒａｓｔ ｒａｔｉｏ、ＣＲ）＝基板の上下の偏光板が平行のときの輝度／基板の上下の偏光板が直交のときの輝度
実施例１２〜２２および、比較例２の感光性樹脂組成物で製作した基板のコントラスト比は、下記表４に示す。
上記表４の結果を参照すれば、本発明の実施例１２〜２２による感光性樹脂組成物を用いた基板の場合、有機溶媒に対して溶解度が低い顔料（ＰＹ１３８）を含む感光性樹脂組成物を用いた基板（比較例２）に比べて光の散乱を減らし、コントラスト比が向上したことを確認できた。 With reference to the results in Table 4 above, in the case of the substrate using the photosensitive resin composition according to Examples 12 to 22 of the present invention, the photosensitive resin composition containing a pigment (PY138) having a low solubility in an organic solvent. It was confirmed that the scattering of light was reduced and the contrast ratio was improved as compared with the substrate using (Comparative Example 2).
Claims (15)
[化学式１]
Ｒ１ 、Ｒ ２ 、Ｒ ４ およびＲ５は、それぞれ、水素またはハロゲンであり；
Ｒ ３ は、下記化学式４の官能基または下記化学式５の官能基であり；
Ｒ６は、下記化学式２または３であり；
Ｒ７〜Ｒ１０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり；
[化学式２]
Ｒ１１〜Ｒ２０は、それぞれ、水素、ハロゲン、炭素数１〜１０の脂肪族基、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり、
Ｒ７〜Ｒ２０のうちの１つ以上は、炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアルコキシ基であり、
[化学式４]
Ｒ ２１ 、Ｒ ２２ およびＲ ２３ は、それぞれ独立して、水素、置換または非置換の炭素数１〜２０のアルキル基；置換または非置換の炭素数１〜２０のアルコキシ基；置換または非置換の炭素数１〜２０のヒドロキシアルキル基；置換または非置換の炭素数６〜３０のアリール基；置換または非置換の炭素数７〜３０のアリールアルキル基；置換または非置換の炭素数７〜３０のアルキルアリール基であり；
前記ｎ、ｎ １ およびｎ ２ は、整数であり、０≦ｎ≦４、０≦ｎ １ ≦３、０≦ｎ ２ ≦３である。 Colorant compound represented by the following chemical formula 1:
[Chemical formula 1]
R 1 , R 2 , R 4 and R 5 are hydrogen or halogen, respectively;
R 3 is a functional group of the following chemical formula 4 or a functional group of the following chemical formula 5;
R 6 is the following chemical formula 2 or 3;
R 7 to R 10 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms;
[Chemical formula 2]
R 11 to R 20 are hydrogen, halogen, an aliphatic group having 1 to 10 carbon atoms, a ring or linear alkylthio group having 1 to 30 carbon atoms (alkoxy group), and an arylthio having 1 to 30 carbon atoms, respectively. A group (aryl thio group), or an alkoxy group having 1 to 30 carbon atoms.
One or more of R 7 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, an aryl thio group having 1 to 30 carbon atoms, or a carbon number of carbon atoms. alkoxy group der of 1 to 30 is,
[Chemical formula 4]
R 21 , R 22 and R 23 are independently hydrogen, substituted or unsubstituted alkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted alkoxy groups having 1 to 20 carbon atoms; substituted or unsubstituted. Hydroxyalkyl groups having 1 to 20 carbon atoms; substituted or unsubstituted aryl groups having 6 to 30 carbon atoms; substituted or unsubstituted arylalkyl groups having 7 to 30 carbon atoms; substituted or unsubstituted aryl groups having 7 to 30 carbon atoms. Alkylaryl group;
The n, n 1 and n 2 are integers, and 0 ≦ n ≦ 4, 0 ≦ n 1 ≦ 3, 0 ≦ n 2 ≦ 3.
前記Ｒ１１〜Ｒ２０は、それぞれ、水素、ハロゲン、または炭素数１〜１０の脂肪族基である、請求項１に記載の着色剤化合物。 One or more of R 7 to R 10 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, or an aryl thio group having 1 to 30 carbon atoms.
The colorant compound according to claim 1 , wherein R 11 to R 20 are hydrogen, halogen, or an aliphatic group having 1 to 10 carbon atoms, respectively.
前記Ｒ１１〜Ｒ１４のうちの１つ以上、またはＲ１５〜Ｒ２０のうちの１つ以上が炭素数１〜３０の環または直鎖状のアルキルチオ基（ａｌｋｙｌ ｔｈｉｏ ｇｒｏｕｐ）、または炭素数１〜３０のアリールチオ基（ａｒｙｌ ｔｈｉｏ ｇｒｏｕｐ）である、請求項１または２に記載の着色剤化合物。 R 7 to R 10 are hydrogen, halogen, or aliphatic groups having 1 to 10 carbon atoms, respectively.
One or more of R 11 to R 14 or one or more of R 15 to R 20 is a ring or linear alkyl thio group having 1 to 30 carbon atoms, or 1 carbon atom. The colorant compound according to claim 1 or 2, which is an arylthio group of ~ 30.
[化学式６]
[Chemical formula 6]
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