TWI812745B - 喹啉黃化合物 - Google Patents
喹啉黃化合物 Download PDFInfo
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- TWI812745B TWI812745B TW108122803A TW108122803A TWI812745B TW I812745 B TWI812745 B TW I812745B TW 108122803 A TW108122803 A TW 108122803A TW 108122803 A TW108122803 A TW 108122803A TW I812745 B TWI812745 B TW I812745B
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- Prior art keywords
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- mass
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- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical class C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 239000000203 mixture Substances 0.000 claims abstract description 34
- 229940051201 quinoline yellow Drugs 0.000 claims abstract description 17
- 239000004172 quinoline yellow Substances 0.000 claims abstract description 17
- 235000012752 quinoline yellow Nutrition 0.000 claims abstract description 17
- 239000003086 colorant Substances 0.000 claims abstract description 10
- 238000004040 coloring Methods 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000001052 yellow pigment Substances 0.000 abstract description 17
- 238000000034 method Methods 0.000 abstract description 15
- 238000006471 dimerization reaction Methods 0.000 abstract description 3
- 238000010521 absorption reaction Methods 0.000 abstract description 2
- 230000005540 biological transmission Effects 0.000 abstract description 2
- 230000021615 conjugation Effects 0.000 abstract description 2
- 230000000447 dimerizing effect Effects 0.000 abstract description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract description 2
- 125000006850 spacer group Chemical group 0.000 abstract description 2
- 125000000879 imine group Chemical group 0.000 abstract 1
- 239000000049 pigment Substances 0.000 description 80
- 150000001875 compounds Chemical class 0.000 description 40
- 238000004519 manufacturing process Methods 0.000 description 23
- 239000006185 dispersion Substances 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 14
- 238000003786 synthesis reaction Methods 0.000 description 14
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 239000012860 organic pigment Substances 0.000 description 7
- 239000003960 organic solvent Substances 0.000 description 7
- 239000003973 paint Substances 0.000 description 7
- 229940067265 pigment yellow 138 Drugs 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 6
- 239000000975 dye Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 239000001056 green pigment Substances 0.000 description 5
- 239000000976 ink Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- -1 quinophthalone compound Chemical class 0.000 description 5
- 239000001054 red pigment Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 239000001055 blue pigment Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 238000000434 field desorption mass spectrometry Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class 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 4
- 230000035484 reaction time Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- AUHHYELHRWCWEZ-UHFFFAOYSA-N tetrachlorophthalic anhydride Chemical compound ClC1=C(Cl)C(Cl)=C2C(=O)OC(=O)C2=C1Cl AUHHYELHRWCWEZ-UHFFFAOYSA-N 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 3
- 239000002270 dispersing agent Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000003999 initiator Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-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
- 239000005711 Benzoic acid Substances 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- HUVXQFBFIFIDDU-UHFFFAOYSA-N aluminum phthalocyanine Chemical class [Al+3].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 HUVXQFBFIFIDDU-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 150000004056 anthraquinones Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000003759 ester based solvent Substances 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 description 2
- 150000002830 nitrogen compounds Chemical class 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000019612 pigmentation Effects 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- ZEMYZPXPNMSHCE-UHFFFAOYSA-N (3-methyl-1-prop-2-enoyloxypentyl) prop-2-enoate Chemical compound CCC(C)CC(OC(=O)C=C)OC(=O)C=C ZEMYZPXPNMSHCE-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
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- WZKWDDGQDVDTGZ-UHFFFAOYSA-N 2-methyl-6-[(2-methylquinolin-6-yl)methyl]quinoline Chemical compound C(C=1C=C2C=CC(=NC2=CC=1)C)C=1C=C2C=CC(=NC2=CC=1)C WZKWDDGQDVDTGZ-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- BJDDKZDZTHIIJB-UHFFFAOYSA-N 4,5,6,7-tetrafluoro-2-benzofuran-1,3-dione Chemical compound FC1=C(F)C(F)=C2C(=O)OC(=O)C2=C1F BJDDKZDZTHIIJB-UHFFFAOYSA-N 0.000 description 1
- ULSOWUBMELTORB-UHFFFAOYSA-N 5,6-dichloro-2-benzofuran-1,3-dione Chemical compound C1=C(Cl)C(Cl)=CC2=C1C(=O)OC2=O ULSOWUBMELTORB-UHFFFAOYSA-N 0.000 description 1
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- 241000208340 Araliaceae Species 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- GTTUGTRPTCKTHF-UPQMTBSMSA-N C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C(C)(C)C)C([C@H](O)[C@H](O)CO)O Chemical compound C(C=C)(=O)O.C(C=C)(=O)O.C(C=C)(=O)O.C(C(C)(C)C)C([C@H](O)[C@H](O)CO)O GTTUGTRPTCKTHF-UPQMTBSMSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
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- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 1
- 235000003140 Panax quinquefolius Nutrition 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
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- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- QHWKHLYUUZGSCW-UHFFFAOYSA-N Tetrabromophthalic anhydride Chemical compound BrC1=C(Br)C(Br)=C2C(=O)OC(=O)C2=C1Br QHWKHLYUUZGSCW-UHFFFAOYSA-N 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- RKFMOTBTFHXWCM-UHFFFAOYSA-M [AlH2]O Chemical compound [AlH2]O RKFMOTBTFHXWCM-UHFFFAOYSA-M 0.000 description 1
- XHPWRTXYJFNZAW-UHFFFAOYSA-N [[4-[2-(4-diazonioimino-2-sulfocyclohexa-2,5-dien-1-ylidene)ethylidene]-3-sulfocyclohexa-2,5-dien-1-ylidene]hydrazinylidene]azanide Chemical compound OS(=O)(=O)C1=CC(N=[N+]=[N-])=CC=C1C=CC1=CC=C(N=[N+]=[N-])C=C1S(O)(=O)=O XHPWRTXYJFNZAW-UHFFFAOYSA-N 0.000 description 1
- LBGCRGLFTKVXDZ-UHFFFAOYSA-M ac1mc2aw Chemical compound [Al+3].[Cl-].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 LBGCRGLFTKVXDZ-UHFFFAOYSA-M 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
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- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
- 150000008641 benzimidazolones Chemical class 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- KQNZLOUWXSAZGD-UHFFFAOYSA-N benzylperoxymethylbenzene Chemical compound C=1C=CC=CC=1COOCC1=CC=CC=C1 KQNZLOUWXSAZGD-UHFFFAOYSA-N 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- QEBHBRUSOHBKAJ-UHFFFAOYSA-M bromoaluminum Chemical compound Br[Al] QEBHBRUSOHBKAJ-UHFFFAOYSA-M 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
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- MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
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- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
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- 230000000694 effects Effects 0.000 description 1
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- 239000004210 ether based solvent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000008434 ginseng Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 150000002466 imines Chemical group 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920006122 polyamide resin Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011164 primary particle Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical compound C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- JBJWASZNUJCEKT-UHFFFAOYSA-M sodium;hydroxide;hydrate Chemical compound O.[OH-].[Na+] JBJWASZNUJCEKT-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000000411 transmission spectrum Methods 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C09B25/00—Quinophthalones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- G—PHYSICS
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/18—Halogen atoms or nitro radicals
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- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
- C09B67/0066—Aqueous dispersions of pigments containing only dispersing agents
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- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
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- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0092—Dyes in solid form
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Abstract
本發明提供兼具優良之亮度及著色力的新穎黃色顏料。
藉由將特定之喹啉黃骨架二聚化,發現顯示更選擇性之吸收/透過。再者,亦對二聚化手法重覆檢討,發現不採用單純的直接鍵結,而使用亞甲基鏈作為間隔基,切斷共軛,可抑制過剩之偏紅化。此外,藉由多鹵化及導入醯亞胺構造,使分散性提高。再者,提供含有該喹啉黃化合物之著色劑,及含有該著色劑之著色組成物。
Description
本發明係關於新穎喹啉黃(quinophthalone)化合物。
專利文獻1及2中,揭示具有一定構造之雙喹啉黃化合物。又,專利文獻3中,揭示具有一定構造之喹啉黃化合物。然而,專利文獻1、2及3中,並未揭示下述式(1)所表示的本發明之化合物。
專利文獻1 日本特公昭48-32765號公報
專利文獻2 國際公開2013/098836號小冊子
專利文獻3 日本特開昭53-228號公報
現今,著色組成物被使用於各種領域,就具體之用途而言,可列舉印刷油墨、塗料、樹脂用著色劑、纖維用著色劑、資訊記錄用色料(使用於彩色濾光片、調色劑、噴墨等之色料)等。使用於著色組成物之色素主要大致分為顏料及染料,就彼等所尋求之性能而言,有色特性(著色力、鮮明性)、耐性(耐候性、耐光性、耐熱性、耐溶劑性)等。通常,與以分子狀態顯色之染料不同,顏料係由粒子狀態(一次粒子之凝集體)顯色。因此,顏料與染料相比,一般為耐性方面較優異者,然而 著色力或鮮明性多較差。由於此種背景,乃尋求高著色力/高彩度之顏料。其中,在著色力之觀點中具有優勢的有機顏料,特別受到矚目。
在此等有機顏料中,迄今已積極開發了許多的新穎顏料,如比色指數之登錄數僅次於紅色顏料的黃色顏料等。就實際上所用之黃色有機顏料而言,例如,在印刷油墨用途方面使用C.I.顏料黃3、顏料黃12、顏料黃74等,在塗料用途方面使用C.I.顏料黃74、顏料黃83、顏料黃109、顏料黃110等,在彩色濾光片用途方面使用C.I.顏料黃129、顏料黃138、顏料黃150、顏料黃185等。然而,彼等之基本構造主要為偶氮、甲亞胺(azomethine)、異吲哚啉、異吲哚啉酮等。因此,黃色有機顏料中之構造變化,尚不足以對應於所要求的各種用途。
尤其,液晶顯示器用彩色濾光片,或者彼等彩色濾光片所用的顏料,要求與先前之泛用用途相異的特性。具體而言,要求可減低背光之電力消耗的「高亮度」,彩色濾光片的薄膜化及可使高色再現的「高著色力」等。然而,現狀是現行之彩色濾光片所用之黃色顏料,並沒有回應此等全部要求的顏料。
其中,彩色濾光片包含紅色畫素部(R)、綠色畫素部(G)及藍色畫素部(B),黃色顏料多作為綠色畫素部之調色用。黃色顏料之中,使用量最多者為C.I.顏料黃138,然而該C.I.顏料黃138缺乏著色力,在要求高色再現性之色規格中無實用性。因此,在高色再現性之色規格中,雖使用C.I.顏料黃150作為現行之黃色顏料,然而該C.I.顏料黃150在亮度/著色力方面亦稱 不上充分。因此,希求創造出兼具優良之亮度及著色力的新穎黃色顏料。
本發明人等為解決上述課題而專心檢討之結果,發現藉由將喹啉黃骨架二聚化,更顯示選擇性吸收/透過。再者,亦在二聚化手法方面重覆檢討,發現不採用單純直接鍵結,而使用亞甲基鏈作為間隔基(spacer),藉由切斷共軛,可抑制過度之偏紅化。此外,藉由、多鹵化及導入醯亞胺構造,可使分散性提高。
本發明人等基於此種檢討結果,發現下述式(1)所表示的化合物可解決上述課題,於是完成本發明。亦即本發明係關於下述式(1):
(式(1)中,X1~X16各自獨立為氫原子或鹵素原子)所表示的喹啉黃化合物(以下,有記載為「本發明化合物」之情況)。
本發明化合物具有優良之亮度及著色力。尤其,在彩色濾光片用途中的高色再現用色規格中,本發明化合物具 有比現今之黃色顏料(C.I.顏料黃150)更良好的亮度,並且具有超過其之優良著色力。
就上述式(1)中之鹵素原子而言,可列舉氟、氯、溴或碘之各原子,其中,以氟原子、氯原子或溴原子為較佳,氯原子為更佳。
再者,上述式(1)所表示的喹啉黃化合物,存在下述通式(1-i)及通式(1-ii)等之構造的互變異構物,而關於此等,亦包含於本發明中。
式(1-i)及式(1-ii)中,X1~X16係如上所述。
本發明之喹啉黃化合物的具體例列舉於下,然而、本發明不被此等限定。
此種本發明化合物之製造方法無特別限制,可適宜利用先前周知之方法而製造。以下,記載本發明化合物的製造方法之一態樣。然而,本發明不受此等限定。
本發明化合物可藉由例如包含以下之步驟I、步驟II、步驟III及步驟IV的方法而得到。
首先,依照J.Heterocyclic Chem.,30,17(1993)記載之方法等,相對於1當量之4,4'-二胺基二苯基甲烷,添加2~3當量之巴豆醛,在氧化劑存在下,於強酸中反應,合成式(2)之6,6’-亞甲基雙(2-甲基喹啉)。
其中,就強酸而言,可列舉鹽酸、硫酸、硝酸等。
就氧化劑而言,可列舉碘化鈉、對四氯苯醌、硝基苯等。
關於步驟I,反應溫度為80℃~100℃,較佳可於90℃~100℃進行,反應時間為1小時~6小時,較佳為於3小時~6小時進行。
再者,藉由使所得到之式(2)之化合物與硝酸或發煙硝酸於濃硫酸存在下反應,可得到式(3)之化合物。
關於步驟II,反應溫度為-20℃~+40℃,較佳可於0℃~+20℃進行,反應時間為1小時~4小時,較佳可於1小時~3小時進行。
再者,藉由對1當量之所得到的式(3)之化合物,添加6~8當量之還原鐵,使其反應,可得到式(4)之化合物。
關於步驟III,反應溫度為60℃~80℃,較佳可於70℃~80℃進行,反應時間為1小時~3小時,較佳可於2小時~3小時進行。
再者,依照日本特開2013~61622號公報記載之方法等,藉由相對於1當量之所得到的式(4)之化合物,使4~6當量之酞酸酐或者四鹵化酞酸酐於酸觸媒存在下反應,可得到式(1)之化合物。
其中,就酸觸媒而言,可列舉苯甲酸、氯化鋅等。
關於步驟IV,反應溫度為180℃~250℃,較佳可於200℃~250℃進行,反應時間為1小時~8小時,較佳可於3小時~8小時進行。
本發明化合物可單獨使用,亦可適當選擇2種以上之化合物併用。
本發明化合物被認為可適用於各種的用途。例如,可使用作為印刷油墨、塗料、著色塑膠、調色劑、噴墨用油墨、顯示器用遮光性構件、種子著色等廣範圍用途的著色劑。
本發明化合物為顯示作為有機顏料之性質者,藉由鹽磨處理等,實施顏料粒子之微細化,有更適合使用的情形。此種處理只要依照周知慣用之方法進行即可。
本發明化合物為了調色等目的,亦可與本發明化合物以外之有機顏料、有機染料、有機顏料衍生物等色料併用。此等可配合上述之用途而適當選擇,依據用途,可將本發明化合物單獨使用,亦可適當併用2種以上。
就可併用之色料而言,只要為周知之顏料、染料等任一者皆可。
依據用途,可列舉偶氮系、雙偶氮系、甲亞胺系、蒽醌系、喹啉黃系、喹吖啶酮系、二酮吡咯并吡咯系、二系、苯并咪唑酮系、酞菁系、異吲哚啉系、異吲哚啉酮系、並系顏料,及二苯并哌喃系、偶氮系、雙偶氮系、蒽醌系、喹啉黃系、三芳基甲烷系、次甲基系、酞菁系、玫瑰紅(rhodamine)系染料等。
就可與本發明化合物併用之黃色顏料而言,在油墨用途方面,可例示C.I.顏料黃3、顏料黃12、顏料黃74等,在塗料用途方面,可例示C.I.顏料黃74、顏料黃83、顏料黃109、顏料黃110等,在彩色濾光片用途方面,可例示C.I.顏料黃83、顏料黃129、顏料黃138、顏料黃139、顏料黃150、顏料黃185、顏料黃231等。
尤其在使用本發明化合物用於形成彩色濾光片用途中之綠色畫素部的情況,例如,可與如C.I.顏料綠1、顏料綠2、顏料綠4、顏料綠7、顏料綠8、顏料綠10、顏料綠13、顏料綠14、顏料綠15、顏料綠17、顏料綠18、顏料綠19、顏料綠26、顏料綠36、顏料綠45、顏料綠48、顏料綠50、顏料綠51、顏料綠54、顏料綠55、顏料綠58、顏料綠59、顏料綠62、顏料綠63之綠色顏料等併用,然而不以此等為限。在使用本發明化合物用於形成彩色濾光片用途中之綠色畫素部的情況,綠色顏料與本發明之黃色顏料的併用比率,例如,對於每100質量份之綠色顏料,黃色顏料為10~100質量份。
又,在使用本發明化合物用於形成綠色畫素部的情況,亦可將本發明化合物與藍色顏料併用。就藍色顏料而言,例如,可列舉C.I.顏料藍15、顏料藍15:1、顏料藍15:2、顏料藍15:3、顏料藍15:4、顏料藍15:6、鋁酞菁衍生物等。
其中,上述之鋁酞菁衍生物,例如,可列舉下述通式(5-1)所表示的化合物等。
(式(5-1)中,R為鹵素原子、羥基、或下述通式(5-2)所表示的基)
(式(5-2)中,X為直接鍵或氧原子;Ar為苯基或萘基;式中,星號表示鍵結部位)
就上述的式(5-1)中之R中的前述鹵素原子而言,例如,可列舉氟原子、氯原子、溴原子、碘原子等。其中,就R中之前述鹵素原子而言,以氯原子、或溴原子為較佳。
式(5-1)中,R以氯原子、溴原子、羥基、或上述通式(5-2)所表示的基為較佳。
式(5-2)中,X以氧原子為較佳。
即使式(5-1)之中,就較佳者而言,例如,可列舉羥基鋁酞菁、氯鋁酞菁、溴鋁酞菁、下述式(5-1-1)所表示的化 合物、下述式(5-1-2)所表示的化合物、下述式(5-1-3)所表示的化合物等。
再者,本發明化合物,亦可與紅色顏料併用而用於形成彩色濾光片用途中之紅色畫素部。就紅色顏料而言,例如,可列舉C.I.顏料紅177、顏料紅254等。
將本發明用於形成彩色濾光片之綠色畫素部的圖案時,可採用周知之方法。典型而言,可得到包含本發明之化合物及感光性樹脂作為必要成分的彩色濾光片用感光性組成物。
就彩色濾光片之製造方法而言,可列舉例如稱為光刻(photolithography)之方法,其係使本發明化合物分散於包含感光性樹脂之分散媒中後,以旋塗法、輥塗法、噴墨法等,塗布在玻璃等透明基板上,繼而對此塗布膜,經由光罩藉由紫外線進行圖案曝光後,將未曝光部分用溶劑等洗淨,得到綠色圖案。將本發明用於形成彩色濾光片之紅色畫素部之圖案的情況亦相同。
此外,亦可藉由電鍍法、轉印法、微胞電解法、PVED(Photovoltaic Electrodeposition,光伏電沉積)法之方法形成畫素部之圖案,製造彩色濾光片。
在調製彩色濾光片用感光性組成物方面,例如,以顏料、感光性樹脂、光聚合起始劑、溶解前述樹脂之有機溶劑作為必要成分,並進行混合。就該製造方法而言,一般為將顏料及有機溶劑,視需要可使用分散劑,調製成分散液後,在其中添加感光性樹脂等而調製的方法。
就此處之顏料而言,在得到綠色畫素部的情況,可使用將本發明化合物顏料化者,及上述之綠色顏料或藍色顏料。同樣地,在得到紅色畫素部之情況方面,可使用將本發明化合物顏料化者,及上述之紅色顏料。
就視需要使用之分散劑而言,可列舉例如BYK-Chemie公司之DISPERBYK(註冊商標名)130、DISPERBYK 161、DISPERBYK 162、DISPERBYK 163、DISPERBYK 170、DISPERBYK LPN-6919、DISPERBYK LPN-21116、BASF公司之Efka-46、Efka-47等。又,亦可與勻塗劑、偶合劑、陽離子系之界面活性劑等合併而使用。
就有機溶劑而言,有例如甲苯或二甲苯、甲氧基苯等芳香族系溶劑;乙酸乙酯或乙酸丁酯、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚乙酸酯等乙酸酯系溶劑;丙酸乙氧基乙酯等丙酸酯系溶劑;甲醇、乙醇等醇系溶劑;丁基賽璐蘇、丙二醇單甲基醚、二乙二醇乙基醚、二乙二醇二甲基醚等醚系溶劑;甲基乙基酮、甲基異丁基酮、環己酮等酮系溶劑;己烷等脂肪族烴系溶劑;N,N-二甲基甲醯胺、γ-丁內醯胺、N-甲基-2-吡咯啶酮、苯胺、吡啶等氮化合物系溶劑;γ-丁內酯等內酯系溶劑;如胺甲酸甲酯與胺甲酸乙酯之48:52之混合物的胺甲酸酯等。就有機溶劑而言,尤其以丙酸酯系、醇系、醚系、酮系、氮化合物系、內酯系等極性溶劑,水可溶者較適合。
每100質量份之本發明之彩色濾光片用顏料組成物,將300~1000質量份之有機溶劑、視需要的100質量份以下之分散劑及/或20質量份以下之喹啉黃衍生物,攪拌分散使其均勻,可得到分散液。繼而,在此分散液中,每100質量份之分散液,添加3~20質量份之感光性樹脂,並且每1質量份之感光性樹脂,添加0.05~3質量份之光聚合起始劑,視需要進一步添加有機溶劑,攪拌分散使其均勻,可得到彩色濾光片畫素部用感光性組成物。
上述之彩色濾光片用顏料組成物,意指對於每10質量份之本發明之喹啉黃顏料組成物,在綠色畫素用途之情況,為適當設定並混合有200質量份以下之綠色顏料或/及200質量份以下之藍色顏料者,又,在紅色畫素用途之情況,為混合有200質量份以下之紅色顏料者。再者,視需要亦可混合有其他的黃色顏料。
就此時可使用之感光性樹脂而言,可列舉例如胺基甲酸酯系樹脂、丙烯酸系樹脂、聚醯胺酸系樹脂、聚醯亞胺系樹脂、苯乙烯馬來酸系樹脂、苯乙烯馬來酸酐系樹脂等熱塑性樹脂;或例如1,6-己二醇二丙烯酸酯、乙二醇二丙烯酸酯、新戊二醇二丙烯酸酯、三乙二醇二丙烯酸酯、雙(丙烯醯氧基乙氧基)雙酚A、3-甲基戊二醇二丙烯酸酯等2官能單體;三羥甲基丙烷三丙烯酸酯、新戊四醇三丙烯酸酯、參(2-羥基乙基)異氰酸酯、二新戊四醇六丙烯酸酯、二新戊四醇五丙烯酸酯等多官能單體等光聚合性單體。
就光聚合起始劑而言,例如苯乙酮、二苯甲酮、苄基二甲基縮酮、過氧化苯甲醯、2-氯-9-氧硫、1,3-雙 (4'-疊氮基苯亞甲基)-2-丙烷、1,3-雙(4'-疊氮基苯亞甲基)-2-丙烷-2'-磺酸、4,4'-二疊氮基二苯乙烯-2,2'-二磺酸等。
此種方式調製之彩色濾光片畫素部用感光性組成物,可藉由經由光罩,利用紫外線進行圖案曝光後,用有機溶劑或鹼性水等洗淨未曝光部分,而製作彩色濾光片。
以下,基於實施例說明本發明,然而本發明並不受其限定。再者,實施例及比較例中若未特別預先說明時,「份」及「%」係以質量為基準。
在燒瓶中添加55g之濃硫酸,於冰冷下攪拌,同時添加7.0g(23.5mmol)之依照文獻(Polymer,volume 39,No.20(1998),p4949)記載之方法所得到的6,6'-亞甲基二(2-甲基喹啉)。保持在10℃以下,同時滴入6.1g之60%硝酸,於10℃至20℃持續攪拌1小時。將反應液注入150ml之冰水中,使用20wt%氫氧化鈉水溶液,調整至pH3。將析出之粉末以減壓過濾回收,用水洗淨至中性。將所得到之固體在70℃送風乾燥後,將粗生成物用100ml之熱乙酸乙酯,再用60ml之熱甲苯洗淨過濾,除去雜質,得到6.52g(16.8mmol)之中間物(A)。(產率:72%)
1H-NMR(DMSO-d6)δppm:2.70(s,6H),4.42(s,2H),7.58(d,J=8.8Hz,2H),7.63(d,J=8.8Hz,2H),8.09(d,J=8.8Hz,2H),8.13(d,J=8.8Hz,2H)
13C-NMR(DMSO-d6)δppm:24.5,32.0,117.7,124.8,127.5,129.8,130.5,131.9,145.8,146.2,160.7
FT-IR(KBr disk)cm-1:3048,1602,1520,1494,1363
在燒瓶中添加5.30g之還原鐵、135ml之乙酸,於攪拌下加熱至50℃。繼而,保持於70℃以下添加4.50g(11.6mmol)之合成例1所得到的化合物(A)。添加結束後,持續於60℃攪拌1小時後,將反應液冷卻至35℃以下,並注入於500ml之冰水中,用20%NaOH水調製成pH9。將所生成之沉澱物於矽藻土上減壓過濾。回收固體物質,在70℃送風乾燥後,添加100ml之二甲亞碸(DMSO)及100ml之N,N-二甲基甲醯胺(DMF)的混合溶劑,於90℃攪拌1小時。將混合物於矽藻土上減壓過濾,將所得到之濾液一面攪拌一面加人至1L之水中。以減壓過濾回收所生成之沉澱物,水洗,得到3.80g(11.6mmol)之中間物(B)。(產率100%)
1H-NMR(DMSO-d6)δppm:2.57(s,6H),3.95(s,2H),5.66(s,4H),7.06(d,J=8.2Hz,2H),7.16(d,J=8.2Hz,2H),7.23(d,J=8.2Hz,2H),8.49(d,J=8.2Hz,2H)
13C-NMR(DMSO-d6)δppm:24.6,32.1,115.8,116.2,119.5,130.9,131.8,141.5,147.4,157.0
FT-IR(KBr disk)cm-1:3464,3363,3315,3192,1640,1591,1573,1415,1365,801
在氮氣環境下,量取135g之苯甲酸置於燒瓶中,並於140℃熔融。在其中,添加3.80g(11.6mmol)之合成例2所得到的中間物(B)及17.99g(62.9mmol)之四氯酞酸酐、0.49g(3.6mmol)之無水氯化鋅,並於220℃攪拌6小時。將反應混合物冷卻至120℃後,添加300mL之氯苯,並攪拌1小時,藉由減壓過濾,得到10.5g(7.5mmol)之為黃色粉末的喹啉黃化合物(C)。(產率:65%)
FT-IR cm-1:1788,1729,1688,1638,1607,1537,1420,1310,732
FD-MS:1400 M+
在合成例3中,使用4,5-二氯酞酸酐代替四氯酞酸酐,得到為黃色粉末之喹啉黃化合物(D)。(產率80%)
FT-IR cm-1:1790,1728,1685,1634,1582,1548,1417,1343,1312,768,740
FD-MS:1124 M+
在合成例3中,使用四溴酞酸酐代替四氯酞酸酐,得到為黃色粉末之喹啉黃化合物(E)。(產率85%)
FT-IR cm-1:1730,1685,1633,1604,1530,1417,1335,1114,661
FD-MS:2111 M+
在合成例3中,使用四氟酞酸酐代替四氯酞酸酐,得到為黃色粉末之喹啉黃化合物(F)。(產率70%)
1H-NMR(DMSO-d6)δppm:4.15(s,2H),7.51(d,j=8.8Hz,2H),8.21(d,j=8.8Hz,2H),8.46(d,j=9.6Hz,2H),8.59(d,j=9.6Hz,2H),13.80(s,2H)
FT-IR cm-1:1734,1633,1614,1494,1387,1091,949
FD-MS:1136 M+
將0.500質量份之前述合成例所得到的喹啉黃化合物與1.50質量份之氯化鈉、0.750質量份之二乙二醇一起磨碎。然後,將其混合物投入600質量份之溫水中,並攪拌1小時。將水不溶分過濾分離,用溫水充分洗淨後,以90℃送風乾燥進行顏料化。顏料之粒子系為100nm以下,粒子之平均長度/寬度比小於3.00。使用所得到之喹啉黃化合物的黃色顏料,進行以下之分散試驗及彩色濾光片評價試驗。
將0.700質量份之喹啉黃化合物(C)加入至玻璃瓶中,添加6.60質量份之丙二醇單甲基醚乙酸酯、1.40質量份之DISPERBYK(註冊商標名)LPN-21116(BYK Chemie股份有限公司製)、22.0質量份之0.3-0.4mmφ賽普爾珠粒,並以油漆調節機(paint conditioner)(東洋精機股份有限公司製)分散2小時。在所得到之分散液中添加6.00質量份之丙二醇單甲基醚乙酸酯,進一步以油漆調節機分散0.5小時,得到顏料分散體。將4.00質量份之所得到之顏料分散體、0.60質量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標名)ZL-295、0.22質量份之丙二醇單甲基醚乙酸酯加入至玻璃瓶中,藉由振動,製作黃色調色用組成物。
除了在製造例1中使用合成例4所得到之喹啉黃化合物(D)代替喹啉黃化合物(C)以外,以同樣之方法製作旋塗液。
將2.48質量份之C.I.顏料綠59(DIC股份有限公司製)加入至玻璃瓶中,添加10.9量份之丙二醇單甲基醚乙酸酯、1.24質量份之DISPERBYK(註冊商標名)LPN-6919(BYK Chemie股份有限公司製)、1.86質量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標名)ZL-295、0.3-0.4mmφ賽普爾珠粒,藉由油漆調節機(東洋精機股份有限公司製)分散2小時,得到顏料分散體。再者,將4.00質量份之所得到之顏料分散體、0.980質量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標名)ZL-295、0.220質量份之丙二醇單甲基醚乙酸酯加入至玻璃瓶中,藉由振動,製作綠色調色用組成物。
將製造例1所得到之黃色調色用組成物及製造例3所得到之綠色調色用組成物混合,藉由旋塗機,塗布在玻璃基板上後,進行乾燥。將所得到之評價用玻璃基板於230℃加熱1小時後,製作在使用高色再現用色規格之C光源之情況顯示各綠色色度的綠色彩色濾光片。再者,就綠色色度而言,使用日本特開2013-205581中所使用的(0.210,0.710)、及日本特開2011-242425中所使用的(0.230,0.670)。
除了使用製造例2所得到之組成物代替製造例1所得到之組成物作為黃色調色用組成物以外,藉由與實施例1同樣之方法製作綠色彩色濾光片。
將0.70質量份之C.I.顏料黃138(BASF公司製)加入至玻璃瓶中,添加6.42質量份之丙二醇單甲基醚乙酸酯、0.467質量份之DISPERBYK(商標名)LPN-6919(BYK Chemie股份有限公司製)、0.700質量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標)ZL-295、22.0質量份之0.3-0.4mmφ賽普爾珠粒,藉由油漆調節機(東洋精機股份有限公司製)分散4小時,得到顏料分散體。再者,將4.00質量份之所得到之顏料分散體、1.00質量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標)ZL-295、0.220質量份之丙二醇單甲基醚乙酸酯加入至玻璃瓶中,製作旋塗液。
除了使用製造例4所得到之組成物代替製造例1所得到之組成物作為黃色調色用組成物以外,依照與實施例1同樣之方法製作綠色彩色濾光片。
將1.14質量份之C.I.顏料黃150(山陽色素公司製)加入塑膠瓶中,添加12.0質量份之丙二醇單甲基醚乙酸酯、2.84質量份之DISPERBYK(註冊商標名)LPN-21116(BYK Chemie股份有限公司製)、38.0質量份之0.3-0.4mmφ賽普爾珠粒,藉由油漆調節機(東洋精機股份有限公司製)分散4小時,得到顏料分散體。再者,將2.00質量份之所得到的顏料分散體、0.490質 量份之DIC股份有限公司製丙烯酸樹脂溶液Unidic(註冊商標名)ZL-295、0.110質量份之丙二醇單甲基醚乙酸酯加入至玻璃瓶中,藉由振動,製作黃色調色用組成物。
除了使用製造例5所得到之組成物代替製造例1所得到之組成物作為黃色調色用組成物以外,依照與實施例1同樣之方法製作綠色彩色濾光片。
除了使用日本特開昭53-228記載之方法所合成的喹啉黃化合物(6)代替C.I.顏料黃138(BASF公司製)以外,依照與製造例4同樣之方法製作黃色調色用組成物。
除了使用製造例6所得到之組成物代替製造例1所得到之組成物作為黃色調色用組成物以外,依照與實施例1同樣之方法製作綠色彩色濾光片。
使用各例製作之彩色濾光片,分別藉由分光光度計(HITACHI公司製U3900/3900H型)測定色度及透過光譜,藉由膜厚計(HITACHI公司製VS1000掃描型白色干擾顯微鏡)測定膜厚(膜厚越薄,越高著色力)。將結果示於以下之表1及表2。
實施例1及實施例2,與現今之使用黃色顏料(C.I.顏料黃150)的比較例2相比,顯示良好之亮度,膜厚顯著地變薄。其係顯示本發明之黃色顏料在高色再現性規格中,為高亮度/高著色力,適合作為彩色濾光片用黃色顏料。
又,即使與比較例3(喹啉黃化合物(6))比較檢討,實施例1及實施例2亦同樣顯示高亮度,且膜厚更薄,因此可確認藉由二聚化使彩色濾光片特性顯著地提高。喹啉黃化合物(6)係作為日本特開昭53-228之實施例2所記載的化合物。
再者,比較例1(C.I.顏料黃138)由於亮度低,且膜厚非常厚,未達到實用程度。因此,本發明化合物具有超過現今之代表性黃色顏料的顯著效果。
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Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53228A (en) * | 1976-06-25 | 1978-01-05 | Teijin Ltd | Yellow organic compounds and method of producing same |
JPS53124555A (en) * | 1977-04-07 | 1978-10-31 | Teijin Ltd | Colouring agent for plastic molded articles |
JP2008074985A (ja) * | 2006-09-22 | 2008-04-03 | Toyo Ink Mfg Co Ltd | 顔料、顔料組成物及び顔料分散体 |
WO2013098836A1 (en) * | 2011-10-24 | 2013-07-04 | Keki Hormusji Gharda | A bis-quinophthalome pigment and a process for preparing the same |
JP2018062578A (ja) * | 2016-10-13 | 2018-04-19 | Dic株式会社 | 新規キノフタロン化合物 |
TW201839062A (zh) * | 2017-03-01 | 2018-11-01 | 日商迪愛生股份有限公司 | 喹啉黃化合物 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS4832765B1 (zh) | 1970-12-29 | 1973-10-09 | ||
JPS4832765A (zh) | 1971-08-31 | 1973-05-02 | ||
GB1570822A (en) * | 1976-02-17 | 1980-07-09 | Teijin Ltd | Quinoline derivatives |
DE4020423A1 (de) * | 1990-06-27 | 1992-01-02 | Basf Ag | Verfahren zur herstellung von chinophthalonen |
JP5604968B2 (ja) | 2010-05-14 | 2014-10-15 | 東レ株式会社 | カラーフィルター用緑色着色剤組成物、カラーフィルター基板および液晶表示装置 |
JP5817028B2 (ja) | 2011-08-23 | 2015-11-18 | 東洋インキScホールディングス株式会社 | カラーフィルタ用着色組成物、およびカラーフィルタ |
KR101380997B1 (ko) | 2012-02-28 | 2014-04-10 | 한국과학기술원 | 공간 인식을 통한 벡터 기반 제스처를 보정하는 방법 및 그 장치 |
JP6024149B2 (ja) | 2012-03-28 | 2016-11-09 | 大日本印刷株式会社 | カラーフィルター用着色樹脂組成物、カラーフィルター、及び液晶表示装置 |
US9764580B2 (en) * | 2013-03-29 | 2017-09-19 | Dai Nippon Printing Co., Ltd. | Thermal transfer sheet, coating liquid for colorant layer, method for manufacturing thermal transfer sheet, and image forming method |
-
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Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS53228A (en) * | 1976-06-25 | 1978-01-05 | Teijin Ltd | Yellow organic compounds and method of producing same |
JPS53124555A (en) * | 1977-04-07 | 1978-10-31 | Teijin Ltd | Colouring agent for plastic molded articles |
JP2008074985A (ja) * | 2006-09-22 | 2008-04-03 | Toyo Ink Mfg Co Ltd | 顔料、顔料組成物及び顔料分散体 |
WO2013098836A1 (en) * | 2011-10-24 | 2013-07-04 | Keki Hormusji Gharda | A bis-quinophthalome pigment and a process for preparing the same |
JP2018062578A (ja) * | 2016-10-13 | 2018-04-19 | Dic株式会社 | 新規キノフタロン化合物 |
TW201839062A (zh) * | 2017-03-01 | 2018-11-01 | 日商迪愛生股份有限公司 | 喹啉黃化合物 |
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