KR102603878B1 - A compound, a method for preparing the same, and a colorant comprising the same - Google Patents
A compound, a method for preparing the same, and a colorant comprising the same Download PDFInfo
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- KR102603878B1 KR102603878B1 KR1020160007121A KR20160007121A KR102603878B1 KR 102603878 B1 KR102603878 B1 KR 102603878B1 KR 1020160007121 A KR1020160007121 A KR 1020160007121A KR 20160007121 A KR20160007121 A KR 20160007121A KR 102603878 B1 KR102603878 B1 KR 102603878B1
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- Prior art keywords
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 47
- 239000003086 colorant Substances 0.000 title claims abstract description 25
- 238000000034 method Methods 0.000 title claims description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 7
- 239000000203 mixture Substances 0.000 claims description 22
- 239000002270 dispersing agent Substances 0.000 claims description 21
- 239000000463 material Substances 0.000 claims description 17
- 239000000049 pigment Substances 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 ammonium cations Chemical class 0.000 claims description 10
- 229920006317 cationic polymer Polymers 0.000 claims description 10
- 150000001768 cations Chemical class 0.000 claims description 10
- JHIAOWGCGNMQKA-UHFFFAOYSA-N 2-methyl-8-quinolinamine Chemical compound C1=CC=C(N)C2=NC(C)=CC=C21 JHIAOWGCGNMQKA-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- UHPGVDHXHDPYQP-UHFFFAOYSA-N 2-methyl-8-nitroquinoline Chemical compound C1=CC=C([N+]([O-])=O)C2=NC(C)=CC=C21 UHPGVDHXHDPYQP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052751 metal Inorganic materials 0.000 claims description 5
- 239000002184 metal Substances 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 5
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 229910052736 halogen Chemical group 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000000178 monomer Substances 0.000 claims description 3
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000003505 polymerization initiator Substances 0.000 claims description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical compound NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 claims description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 claims description 2
- 239000001060 yellow colorant Substances 0.000 abstract description 12
- 125000000524 functional group Chemical group 0.000 description 14
- 125000003118 aryl group Chemical group 0.000 description 11
- 239000000975 dye Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 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
- 239000000040 green colorant Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000001062 red colorant Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N phthalic anhydride Chemical group C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- 125000003367 polycyclic group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YLJYVKLZVHWUCT-UHFFFAOYSA-N 5-tert-butyl-2-benzofuran-1,3-dione Chemical compound CC(C)(C)C1=CC=C2C(=O)OC(=O)C2=C1 YLJYVKLZVHWUCT-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 229910004298 SiO 2 Inorganic materials 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- 235000010233 benzoic acid Nutrition 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000001767 cationic compounds Chemical class 0.000 description 2
- 238000010668 complexation reaction Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000004973 liquid crystal related substance Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 239000001007 phthalocyanine dye Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- IZMJMCDDWKSTTK-UHFFFAOYSA-N quinoline yellow Chemical group C1=CC=CC2=NC(C3C(C4=CC=CC=C4C3=O)=O)=CC=C21 IZMJMCDDWKSTTK-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 239000001043 yellow dye Substances 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical class CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000536 complexating effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000006170 formylation reaction Methods 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- AJDUTMFFZHIJEM-UHFFFAOYSA-N n-(9,10-dioxoanthracen-1-yl)-4-[4-[[4-[4-[(9,10-dioxoanthracen-1-yl)carbamoyl]phenyl]phenyl]diazenyl]phenyl]benzamide Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C=CC=C2NC(=O)C(C=C1)=CC=C1C(C=C1)=CC=C1N=NC(C=C1)=CC=C1C(C=C1)=CC=C1C(=O)NC1=CC=CC2=C1C(=O)C1=CC=CC=C1C2=O AJDUTMFFZHIJEM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052760 oxygen Chemical group 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000005309 thioalkoxy group Chemical group 0.000 description 1
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
- C07D215/38—Nitrogen atoms
- C07D215/40—Nitrogen atoms attached in position 8
-
- 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
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- 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
-
- 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
- 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
- C09B67/0063—Preparation of organic pigments of organic pigments with only macromolecular substances
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Optics & Photonics (AREA)
- Optical Filters (AREA)
- Plural Heterocyclic Compounds (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
본 발명에서는 황색 착색제 화합물, 이의 제조 방법, 및 이를 포함하는 착색제가 개시된다.The present invention discloses a yellow colorant compound, a method for producing the same, and a colorant containing the same.
Description
본 발명은 우수한 내열성을 갖는 황색 착색제 화합물, 및 이의 제조 방법에 관한 것이다. 본 발명은 또한 상기 염료 화합물을 포함하는 컬러필터용 착색제 조성물, 및 이러한 컬러필터를 구비한 디스플레이 장치에 관한 것이다.The present invention relates to a yellow colorant compound having excellent heat resistance, and a method for producing the same. The present invention also relates to a colorant composition for a color filter containing the above dye compound, and a display device equipped with such a color filter.
컬러필터는 다양한 분야에서 널리 사용되고 있으며, 특히 액정 디스플레이(liquid crystal display; LCD) 및 유기발광다이오드(organic light-emitting diode; OLED) 디스플레이 등의 디스플레이 장치에서 사용되고 있다. 디스플레이 기술의 급격한 발전으로 인해 컬러필터 기술의 추가적인 개선, 특히 휘도(brightness), 콘트라스트비(contrast ratio), 및 색 재현성 면에서의 개선이 업계에서 요구되고 있다.Color filters are widely used in various fields, especially in display devices such as liquid crystal displays (LCD) and organic light-emitting diode (OLED) displays. Due to the rapid development of display technology, additional improvements in color filter technology, especially improvements in brightness, contrast ratio, and color reproducibility, are required in the industry.
컬러필터를 형성할 때는 안료 및/또는 염료를 포함하는 착색제 물질을 함유하는 착색 조성물이 종종 사용된다. 염료에 비해 안료는 일반적으로 열 및/또는 환경에 대하여 보다 나은 안정성을 보이는 반면, 달성가능한 휘도가 종종 불충분하다. 반면, 염료가 컬러필터의 착색제로서 사용되는 경우, 컬러필터의 휘도 측면에서는 만족스러운 결과가 얻어질 수 있으나, 이의 안정성, 특히 내열성, 및/또는 콘트라스트비는 종종 불충분하다.When forming color filters, coloring compositions containing colorant substances including pigments and/or dyes are often used. While pigments compared to dyes generally show better stability to heat and/or the environment, the achievable brightness is often insufficient. On the other hand, when a dye is used as a colorant for a color filter, satisfactory results can be obtained in terms of the luminance of the color filter, but its stability, especially heat resistance, and/or contrast ratio are often insufficient.
하나 이상의 황색 착색제, 예컨대 황색 안료 및 황색 염료 등이 적색 또는 녹색 픽셀용 컬러필터에서 조색제(auxiliary colorant)로서 종종 사용된다. 이러한 황색 착색제는 1종 이상의 적색/녹색 착색제와 함께 사용될 수 있고, 이때 상기 적색/녹색 착색제가 단독으로 사용되었을 때 나타내는 색을 시프트(shift)시킬 수 있다. 디스플레이 컬러필터 용도에서 유리하게 사용될 수 있는 황색 염료의 개발이 업계에서 요구되고 있다.One or more yellow colorants, such as yellow pigments and yellow dyes, are often used as auxiliary colorants in color filters for red or green pixels. This yellow colorant can be used in combination with one or more red/green colorants, and can shift the color displayed when the red/green colorant is used alone. There is a demand in the industry for the development of a yellow dye that can be advantageously used in display color filter applications.
본 발명의 목적은 디스플레이의 컬러필터 형성용 황색 착색제로서 유리하게 사용될 수 있는 화합물을 제공하는 것이다. 본 발명의 다른 목적은 디스플레이 용도에서 컬러필터 가공시의 고온 공정을 견디면서도 충분한 휘도와 콘트라스트비를 나타낼 수 있는 화합물을 제공하는 것이다. 본 발명의 또 다른 목적은 디스플레이용 컬러필터의 형성시 사용되는 용매에서 유리한 분산성을 나타내는 화합물을 제공하는 것이다.The object of the present invention is to provide compounds that can be advantageously used as yellow colorants for forming color filters in displays. Another object of the present invention is to provide a compound that can exhibit sufficient brightness and contrast ratio while withstanding the high temperature process during color filter processing in display applications. Another object of the present invention is to provide a compound that exhibits advantageous dispersibility in a solvent used in forming a color filter for a display.
본 발명자들은 놀랍게도 본 발명에 따른 퀴노프탈론(quinophthalone) 구조체로부터 유도된 화합물이 뛰어난 안정성, 특히 우수한 내광성 및 내열성뿐 아니라 우수한 분산성까지 보일 수 있다는 것을 발견하여 본 발명을 완성하기에 이르렀다. 본 발명자들은 또한 본 발명에 따른 화합물이 우수한 휘도 및 콘트라스트비를 갖는 컬러필터를 형성하는 데 유리하게 사용될 수 있다는 사실도 발견하였다.The present inventors surprisingly discovered that a compound derived from the quinophthalone structure according to the present invention can exhibit excellent stability, particularly excellent light and heat resistance, as well as excellent dispersibility, and thus completed the present invention. The present inventors have also discovered that the compounds according to the present invention can be advantageously used to form color filters with excellent luminance and contrast ratio.
본 발명에 따른 화합물은 뛰어난 내열성과 우수한 휘도 및 콘트라스트비를 달성할 수 있을뿐 아니라, 우수한 분산성을 가질 수 있어, 디스플레이용 컬러필터를 형성하는 데 유리하게 사용될 수 있다.The compound according to the present invention can not only achieve excellent heat resistance and excellent brightness and contrast ratio, but also have excellent dispersibility, so it can be advantageously used to form a color filter for a display.
본 발명에 있어서, "알킬기"란 특히 일반적으로 탄소원자 1 내지 20개를 갖는 직쇄, 분지쇄, 또는 환형 탄화수소기를 의미하는 것으로 이해된다. 알킬기의 예로는 메틸, 에틸, 프로필, 이소프로필, 부틸, 이소부틸, sec-부틸, tert-부틸, 펜틸, 네오펜틸, 헥실, 시클로프로필, 시클로부틸, 시클로펜틸, 및 시클로헥실이 포함된다.In the present invention, “alkyl group” is particularly understood to mean a straight-chain, branched-chain, or cyclic hydrocarbon group, generally having 1 to 20 carbon atoms. Examples of alkyl groups include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec -butyl, tert -butyl, pentyl, neopentyl, hexyl, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl.
본 발명에 있어서, "아릴기"란 특히 방향족 환으로부터 유도된 임의의 관능기 또는 치환체를 의미하는 것으로 이해된다. 구체적으로 아릴기는 탄소원자 1 내지 20개(특히 6 내지 12개가 저비용으로 용이하게 합성할 수 있다는 점에서 바람직함)를 가질 수 있고, 아릴기의 수소원자의 일부 또는 전부는 다른 기들, 특히 알킬기, 알콕시기, 아릴기, 아릴옥시기, 티오알콕시기, 이종고리 화합물(heterocycle), 아미노기 또는 히드록실기에 의해 치환되거나 치환되지 않을 수 있다. 아릴기로는 바람직하게는 임의로 치환된 페닐기, 나프틸기, 안트릴기, 및 페난트릴기 등을 들 수 있다.In the present invention, “aryl group” is understood to mean particularly any functional group or substituent derived from an aromatic ring. Specifically, the aryl group may have 1 to 20 carbon atoms (particularly 6 to 12 carbon atoms are preferred because they can be easily synthesized at low cost), and some or all of the hydrogen atoms of the aryl group may be used in other groups, especially alkyl groups, It may or may not be substituted by an alkoxy group, an aryl group, an aryloxy group, a thioalkoxy group, a heterocycle, an amino group, or a hydroxyl group. Preferred aryl groups include optionally substituted phenyl groups, naphthyl groups, anthryl groups, and phenanthryl groups.
본 발명에 있어서, "밀베이스(millbase) 조성물"이란 특히 컬러필터를 형성하기 위한 최종 조성물 중에 포함되는 성분들 중 적어도 일부를 포함하는 중간체 조성물을 의미하는 것으로 이해된다. 상기 컬러필터를 형성하기 위한 최종 조성물은 밀베이스 조성물과 다른 성분들을 조합함으로써 제조될 수 있다. 본 발명에서, 밀베이스 조성물은 종종 컬러필터를 형성하기 위한 최종 조성물 중에 포함되는 착색제 성분을 포함한다.In the present invention, “millbase composition” is understood to mean, in particular, an intermediate composition containing at least some of the components included in the final composition for forming a color filter. The final composition for forming the color filter can be prepared by combining the millbase composition and other ingredients. In the present invention, the millbase composition often includes a colorant component that is included in the final composition for forming the color filter.
본 발명의 일 측면은, 하기 화학식 1을 갖는 화합물에 관한 것이다:One aspect of the invention relates to a compound having the formula (1):
본 발명에서, X는 독립적으로 수소 또는 할로겐으로부터 선택된다. 본 발명에서는 모든 X가 수소인 것이 바람직하다.In the present invention, X is independently selected from hydrogen or halogen. In the present invention, it is preferred that all X's are hydrogen.
본 발명에서, Y는 관능기를 나타낸다. 이러한 관능기는 다양한 목적들, 예컨대 안정성(예를 들어 내광성 및 내열성) 및/또는 분산성을 향상시킬 목적으로 상기 퀴노프탈론 유도체 화합물에 도입될 수 있다. 본 발명에서, Y는 바람직하게는 -SO3 -M+, -COO-M+, -COH, -C(O)NR'R", -S(O)2NR'R", -NO2, 및 -NR'R" (여기서 M+는 독립적으로 양이온이고, R' 및 R"는 독립적으로 수소, 알킬기 또는 아릴기로부터 선택되거나, R' 및 R"는 서로 결합하여 단환 또는 다환 구조를 형성할 수 있음)로 구성되는 군으로부터 선택된다. 이러한 환 구조는 하나 이상의 헤테로 원자, 예컨대 질소, 황 및 산소를 포함할 수도 있다. 환 구조의 예로는 하기의 구조가 포함되나, 본 발명은 이에 제한되지 않는다:In the present invention, Y represents a functional group. These functional groups can be introduced into the quinophthalone derivative compounds for various purposes, such as improving stability (eg light resistance and heat resistance) and/or dispersibility. In the present invention, Y is preferably -SO 3 -M + , -COO -M + , -COH, -C(O)NR'R", -S(O) 2 NR'R", -NO 2 , and -NR'R" (wherein M + is independently a cation, R' and R" are independently selected from hydrogen, an alkyl group, or an aryl group, or R' and R" may be combined with each other to form a monocyclic or polycyclic structure. This ring structure may contain one or more heteroatoms such as nitrogen, sulfur and oxygen. Examples of ring structures include the following structures, but the present invention is not limited thereto. Does not:
본 발명에서는 특히 Y가 -SO3 -M+인 경우 우수한 결과가 얻어질 수 있다. 임의의 특정 이론에 구애되는 바 없이, 이러한 -SO3 -M+기의 도입에 의해 뛰어난 내열성 및 분산성이 얻어질 수 있는 것으로 이해된다.In the present invention, excellent results can be obtained, especially when Y is -SO 3 -M + . Without being bound by any particular theory, it is understood that excellent heat resistance and dispersibility can be obtained by the introduction of this -SO 3 -M + group.
본 발명에서, R1 내지 R8는 무수프탈산 구조체의 치환기를 나타낸다. 상기 화합물의 최종 어플리케이션에서의 용도를 실질적으로 방해하지 않는다면 어떠한 종류의 치환기라도 사용될 수 있다. 바람직하게는, R1 내지 R8은 독립적으로 수소, 알킬기, 아릴기, 알킬 에스테르(예컨대 메틸 에스테르, 에틸 에스테르 등), 아릴 에스테르, 및 상기에서 설명된 관능기("Y")로 구성되는 군으로부터 선택된다. 본 발명에서, R1 내지 R8 중 적어도 하나가 벌크 유기기(bulky organic group)를 포함하는 것이 특히 바람직하다. 이러한 벌크 유기기는 상기 화합물의 유기 용매 중 분산성을 증가시킬 수 있을뿐 아니라 상기 화합물의 내열성도 개선시킬 수 있다. 상기 벌크 유기기의 대표예로서 탄소수가 3개 이상인 알킬기, 예컨대 프로필, 이소프로필, 부틸, 이소부틸, sec-부틸, tert-부틸, 펜틸, 네오펜틸, 및 헥실기가 포함되나, 본 발명은 이에 제한되지 않는다. 특히 R2 및 R6가 상기 벌크 유기기이면서 R1, R3, R4, R5, R7, 및 R8이 모두 수소인 것이 바람직하다.In the present invention, R1 to R8 represent substituents of the phthalic anhydride structure. Any type of substituent may be used as long as it does not substantially interfere with the use of the compound in its final application. Preferably, R1 to R8 are independently selected from the group consisting of hydrogen, alkyl groups, aryl groups, alkyl esters (such as methyl esters, ethyl esters, etc.), aryl esters, and functional groups (“Y”) described above. . In the present invention, it is particularly preferred that at least one of R1 to R8 contains a bulk organic group. These bulk organic groups can not only increase the dispersibility of the compound in organic solvents but also improve the heat resistance of the compound. Representative examples of the bulk organic group include alkyl groups having 3 or more carbon atoms, such as propyl, isopropyl, butyl, isobutyl, sec -butyl, tert -butyl, pentyl, neopentyl, and hexyl groups, but the present invention includes Not limited. In particular, it is preferable that R2 and R6 are the above bulk organic groups and that R1, R3, R4, R5, R7, and R8 are all hydrogen.
본 발명에서 M+는 임의의 양이온일 수 있다. 이러한 양이온의 특정예로는 양성자(proton), 암모늄 양이온, 및 금속 양이온, 예컨대 알칼리 금속 양이온 (예를 들어 Li+, Na+, K+ 등), 알칼리 토금속 양이온 (예를 들어 Mg2+, Ca2+ 등), 및 주기율표 13족 금속 양이온 (예를 들어 Al3+) 등을 들 수 있다. 본 발명에서는 M+로서 양성자, 암모늄 양이온, 및 알칼리 금속 양이온이 바람직하게 사용될 수 있다. 별법으로, 상기 관능기(Y)가 산성기, 예컨대 -SO3 -H+ 및 -COO-H+로부터 선택되는 경우, 이러한 관능기는 다양한 목적을 위해 양이온성 화합물(cationic compound)과의 컴플렉스화(complexation)를 통해 추가로 개질될 수 있다.In the present invention, M + may be any cation. Specific examples of such cations include protons, ammonium cations, and metal cations such as alkali metal cations (e.g. Li + , Na + , K + etc.), alkaline earth metal cations (e.g. Mg 2+ , Ca 2+, etc.), and metal cations of group 13 of the periodic table (for example, Al 3+ ). In the present invention, protons, ammonium cations, and alkali metal cations can be preferably used as M + . Alternatively, if the functional group (Y) is selected from acidic groups, such as -SO 3 -H + and -COO -H + , these functional groups can be used for complexation with cationic compounds for various purposes. ) can be further modified through.
이러한 양이온성 화합물의 바람직한 예로서 양이온성 중합체 기재 분산제(cationic polymer-based dispersant)를 들 수 있다. 따라서, 본 발명에서 M+는 양이온성 중합체 기재 분산제의 양이온부일 수 있다. 상기 관능기를 이러한 양이온성 중합체 기재 분산제와 컴플렉스화시킴으로서 내열성 및/또는 분산성의 추가적인 개선이 달성될 수 있다. 상기 양이온성 중합체 기재 분산제의 특정예로서 1종 이상의 암모늄기를 포함하는 중합체 기재 분산제를 들 수 있다. 본 발명에서 상기 양이온성 중합체 기재 분산제의 평균 분자량(Mw)은 4,000 g/mol 내지 30,000 g/mol일 수 있고, 바람직하게는 Mw가 7,000 g/mol 내지 25,000 g/mol인 양이온성 중합체 기재 분산제가 사용될 수 있다. 양이온성 중합체 기재 분산제, 특히 1종 이상의 암모늄기를 포함하는 상기 분산제는 BYK CHEMIE로부터 구매할 수 있다 (BYK 시리즈).A preferred example of such a cationic compound is a cationic polymer-based dispersant. Therefore, in the present invention, M + may be the cationic portion of the cationic polymer-based dispersant. Further improvements in heat resistance and/or dispersibility can be achieved by complexing the above functional groups with such cationic polymer based dispersants. Specific examples of the cationic polymer-based dispersant include polymer-based dispersants containing at least one ammonium group. In the present invention, the average molecular weight (Mw) of the cationic polymer-based dispersant may be 4,000 g/mol to 30,000 g/mol, and preferably the cationic polymer-based dispersant has an Mw of 7,000 g/mol to 25,000 g/mol. can be used Cationic polymer based dispersants, especially those containing at least one ammonium group, can be purchased from BYK CHEMIE (BYK series).
따라서, 본 발명의 또 다른 측면은 하나 이상의 본 발명의 따른 화합물 및 하나 이상의 양이온성 중합체 기재 분산제의 콤플렉스(complex)에 관한 것이다. 이러한 컴플렉스는 상기 착색제 화합물 및 분산제를 용매 중에서 임의로 교반 하에 혼합함으로써 형성될 수 있다.Accordingly, another aspect of the invention relates to a complex of one or more compounds according to the invention and one or more dispersants based on cationic polymers. This complex can be formed by mixing the colorant compound and dispersant in a solvent, optionally with stirring.
본 발명의 화합물은 바람직하게는 하기 화학식 1a를 갖는 음이온을 포함한다:The compounds of the present invention preferably contain an anion having the formula (1a):
<화학식 1a><Formula 1a>
본 발명의 또 하나의 측면은 본 발명의 화합물의 제조 방법에 관한 것이다.Another aspect of the present invention relates to methods for preparing the compounds of the present invention.
본 발명의 일 실시태양에서, 상기 제조 방법은 적어도, 1종 이상의 치환 또는 비치환의 8-퀴날딘(8-quinaldine)을 1종 이상의 관능화제(functionalizing agent)와 반응시키는 것을 포함한다. 상기 치환된 8-퀴날딘의 특정예로서 8-니트로퀴날딘 및 8-아미노퀴날딘을 들 수 있으나, 본 발명은 이에 제한되지 않는다.In one embodiment of the present invention, the production method includes reacting at least one type of substituted or unsubstituted 8-quinaldine with one or more functionalizing agents. Specific examples of the substituted 8-quinaldine include 8-nitroquinaldine and 8-aminoquinaldine, but the present invention is not limited thereto.
본 발명에서, "관능화제"란 특히 원하는 관능기를 대상 화합물에 부여할 수 있는 화학작용제(chemical agent)를 의미하는 것으로 이해된다. 본 발명에서, 상기 관능기의 바람직한 예로서 -SO3 -M+, -COO-M+, -COH, -C(O)NR'R", -S(O)2NR'R", -NO2, 및 -NR'R" (여기서 M+는 독립적으로 양이온이고, R' 및 R"는 독립적으로 수소, 알킬기 또는 아릴기로부터 선택되거나, R' 및 R"는 서로 결합하여 단환 또는 다환 구조를 형성할 수 있음)를 들 수 있으나, 본 발명은 이에 제한되지 않는다.In the present invention, “functionalizing agent” is understood to mean, in particular, a chemical agent capable of imparting a desired functional group to the target compound. In the present invention, preferred examples of the functional group include -SO 3 -M + , -COO -M + , -COH, -C(O)NR'R", -S(O) 2 NR'R", -NO 2 , and -NR'R" (wherein M + is independently a cation, R' and R" are independently selected from hydrogen, an alkyl group, or an aryl group, or R' and R" are combined with each other to form a monocyclic or polycyclic structure. can be performed), but the present invention is not limited thereto.
상기 관능기(Y)를 치환 또는 비치환의 8-퀴날딘에 도입하는 방법으로서 임의의 공지된 방법 및 관능화제가 사용될 수 있다. 예컨대, -SO3 -H+기는 1종 이상의 술폰화제(sulfonating agent)를 사용함으로써 치환 또는 비치환의 8-퀴날딘에 도입될 수 있다. 이러한 술폰화제의 예로는 황산(농황산 및 일반 황산 포함), 발연황산, 클로로술폰산, 삼산화황, 및 아미도술폰산을 포함하나, 이에 제한되지 않는다. -COO-H+ 및 -NO2기의 도입은 각각 포르밀화 반응 및 니트로화 반응(예컨대 질산을 사용)에 의해 수행될 수 있다. 몇몇 종류의 관능기를 치환 8-퀴날딘으로 도입하는 반응식은 하기와 같이 예시될 수 있으나, 본 발명은 이에 제한되지 않는다:As a method for introducing the functional group (Y) into substituted or unsubstituted 8-quinaldine, any known method and functionalizing agent can be used. For example, the -SO 3 -H + group can be introduced into substituted or unsubstituted 8-quinaldine by using one or more sulfonation agents. Examples of such sulfonating agents include, but are not limited to, sulfuric acid (including concentrated and regular sulfuric acid), fuming sulfuric acid, chlorosulfonic acid, sulfur trioxide, and amidosulfonic acid. The introduction of -COO -H + and -NO 2 groups can be carried out by formylation reaction and nitration reaction (eg using nitric acid), respectively. The reaction scheme for introducing several types of functional groups into substituted 8-quinaldine can be illustrated as follows, but the present invention is not limited thereto:
본 발명에 따른 화합물을 제조하는 방법은 상기 1종 이상의 관능화제와의 반응에 따라 관능기가 도입된 상기 치환 또는 비치환의 8-퀴날딘 화합물을 추가로 1종 이상의 치환 또는 비치환의 무수 프탈산과 이미드화 반응시켜 본 발명에 따른 화합물을 제조하는 것을 포함한다. 예시적인 반응식은 하기와 같으나, 본 발명은 이에 제한되지 않는다.The method for producing the compound according to the present invention is to imidize the substituted or unsubstituted 8-quinaldine compound into which a functional group is introduced through reaction with the at least one functionalizing agent with at least one substituted or unsubstituted phthalic anhydride. It involves producing a compound according to the present invention by reacting it. An exemplary reaction scheme is as follows, but the present invention is not limited thereto.
별법으로, 본 발명에 따른 화합물의 제조 방법은 먼저 1종 이상의 치환 또는 비치환의 무수 프탈산을 (상기 관능기(Y)가 도입되지 않은) 치환 또는 비치환의 8-퀴날딘, 특히 8-아미노퀴날딘과 반응시켜 하기 화학식 2의 화합물을 생성하고, 그 다음 상기 화학식 2의 화합물을 1종 이상의 관능화제와 반응시켜 의도하는 목적에 적합한 관능화제(Y)를 도입함으로써 수행될 수 있다:Alternatively, the method for preparing the compound according to the present invention first combines one or more substituted or unsubstituted phthalic anhydrides with substituted or unsubstituted 8-quinaldine (without said functional group (Y) introduced), especially 8-aminoquinaldine. This can be carried out by reacting to produce a compound of the following formula (2), and then reacting the compound of formula (2) with one or more functionalizing agents to introduce a functionalizing agent (Y) suitable for the intended purpose:
상기 화학식 2에서, 각 X 및 R1 내지 R8은 상기 설명된 바와 같다.In Formula 2, each of X and R1 to R8 is as described above.
따라서, 본 발명의 추가의 실시태양에서, 본 발명의 화합물의 제조 방법은 상기 화학식 2의 화합물 1종 이상과 1종 이상의 관능화제를 반응시키는 것을 포함한다.Accordingly, in a further embodiment of the present invention, the method for preparing the compounds of the present invention comprises reacting at least one compound of formula (2) above with at least one functionalizing agent.
본 발명의 화합물 또는 컴플렉스는 황색 착색제로서 유리하게 사용될 수 있으며, 이는 임의의 1종 이상의 염료 또는 안료와 조합하여 사용될 수도 있다. 본 발명의 화합물 또는 컴플렉스는 특히 디스플레이용 컬러필터 용도에서 조색제로서 1종 이상의 적색 또는 녹색 주색제(main colorant)와 조합하여 유리하게 사용될 수 있다. 따라서, 본 발명의 또 다른 측면은 본 발명에 따른 화합물, 및 임의로 1종 이상의 다른 염료 또는 안료를 포함하는 착색제 물질을 제공한다. 본 발명의 또 하나의 측면은 본 발명에 따른 컴플렉스, 및 임의로 1종 이상의 다른 염료 또는 안료를 포함하는 착색제 물질을 제공한다.The compounds or complexes of the present invention can be advantageously used as yellow colorants, which may be used in combination with any one or more dyes or pigments. The compounds or complexes of the present invention can be advantageously used in combination with one or more red or green main colorants as colorants, especially in color filter applications for displays. Accordingly, another aspect of the invention provides a colorant material comprising a compound according to the invention, and optionally one or more other dyes or pigments. Another aspect of the invention provides a colorant material comprising the complex according to the invention, and optionally one or more other dyes or pigments.
이러한 염료 및 안료의 예는 PCT 국제특허출원 공개공보 WO 2012/144521 A1호 및 일본 특허출원 공개공보 JP 2014-108975 A호 (그 개시내용이 각각 본원에 전체로서 참조로 포함됨)를 참조할 수 있다. 구체적으로는 본 발명의 화합물은 1종 이상의 녹색 착색제, 예컨대 할로겐화 금속 프탈로시아닌 염료 또는 안료, 예컨대 피그먼트 그린 58, 또는 1종 이상의 적색 착색제, 예컨대 피그먼트 레드 254 등과 조합되어 착색제 물질로서 사용될 수 있다. 또한, 본 발명의 컴플렉스는 1종 이상의 녹색 착색제, 예컨대 할로겐화 금속 프탈로시아닌 염료 또는 안료, 예컨대 피그먼트 그린 58, 또는 1종 이상의 적색 착색제, 예컨대 피그먼트 레드 254 등과 조합되어 착색제 물질로서 사용될 수 있다.For examples of such dyes and pigments, see PCT International Patent Application Publication WO 2012/144521 A1 and Japanese Patent Application Publication JP 2014-108975 A, the disclosures of which are each incorporated herein by reference in their entirety. . Specifically, the compounds of the present invention can be used as a colorant material in combination with one or more green colorants, such as halogenated metal phthalocyanine dyes or pigments, such as Pigment Green 58, or one or more red colorants, such as Pigment Red 254, etc. Additionally, the complex of the present invention can be used as a colorant material in combination with one or more green colorants, such as a halogenated metal phthalocyanine dye or pigment, such as Pigment Green 58, or one or more red colorants, such as Pigment Red 254, etc.
본 발명의 화합물은 컬러필터, 특히 디스플레이용 컬러필터를 형성하는 데 적절하게 사용될 수 있다. 또한, 본 발명의 컴플렉스는 컬러필터, 특히 디스플레이용 컬러필터를 형성하는 데 적절하게 사용될 수 있다. 따라서, 본 발명의 추가의 일 측면은 본 발명에 따른 화합물, 컴플렉스, 또는 착색제 물질을 포함하는, 컬리필터용 조성물에 관한 것이다. 상기 밀베이스 조성물은 임의로, 안료, 바인더, 분산조제 또는 분산제, 중합가능한 모노머, 용매, 억제제, 중합 개시제, 및 이들의 임의의 조합으로 구성되는 군으로부터 선택되는 1개 이상의 성분을 포함할 수 있다.The compounds of the present invention can be suitably used to form color filters, especially color filters for displays. Additionally, the complex of the present invention can be suitably used to form color filters, especially color filters for displays. Accordingly, a further aspect of the invention relates to a composition for a curlifilter comprising a compound, complex, or colorant material according to the invention. The millbase composition may optionally include one or more components selected from the group consisting of pigments, binders, dispersing aids or dispersants, polymerizable monomers, solvents, inhibitors, polymerization initiators, and any combinations thereof.
상기 안료, 바인더, 분산조제/분산제, 중합가능한 모노머, 용매, 억제제, 및 개시제를 비롯한, 상기 언급된 성분의 추가적인 세부사항은 예컨대 PCT 국제특허출원 공개공보 WO 2012/144521 A호, 일본 특허출원 공개공보 JP 2014-108975 A호, 및 PCT 국제특허출원 공개공보 WO 2013/050431호(이의 개시내용이 본원에 전체로서 참조로 포함됨)의 개시내용을 참조할 수 있다. 본 발명에 있어서, 빅케미사(BYK CHEMIE)로부터 구매 가능한 분산제들, 특히 BYK 시리즈, 및 오츠카 케미컬사(Otsuka Chemical Co., Ltd.)로부터 구매 가능한 분산제들, 특히 TERPLUS D 시리즈가 특히 유리하다.Additional details of the above-mentioned ingredients, including the pigments, binders, dispersing aids/dispersants, polymerizable monomers, solvents, inhibitors, and initiators, can be found in, for example, PCT International Patent Application Publication No. WO 2012/144521 A, Japanese Patent Application Publication No. Reference may be made to the disclosures of Publication No. JP 2014-108975 A, and PCT International Patent Application Publication No. WO 2013/050431, the disclosures of which are incorporated herein by reference in their entirety. For the present invention, dispersants commercially available from BYK CHEMIE, especially the BYK series, and dispersants commercially available from Otsuka Chemical Co., Ltd., especially the TERPLUS D series, are particularly advantageous.
본 발명에서, 컬러필터용 밀베이스 조성물은 특히 (A) 착색제 물질; (B) 용매; 및 (C) 분산제를 포함하고, 상기 착색제 물질 (A)는 본 발명의 화합물 또는 컴플렉스, 또는 본 발명의 착색제 물질을 포함한다.In the present invention, the mill base composition for a color filter particularly includes (A) a colorant material; (B) solvent; and (C) a dispersant, wherein the colorant material (A) comprises a compound or complex of the present invention, or a colorant material of the present invention.
본 발명은 또한 본 발명의 화합물 또는 착색제 물질을 포함하는 컬러필터에 관한 것이다. 이러한 컬러필터는 리소그래피 방법, 특히 이하의 단계들을 통해 제조될 수 있다: 본 발명에 따른 밀베이스 조성물에 추가적인 성분들을 조합하여 컬러필터 형성용 조성물을 조제, 이 조성물의 기재 상에의 도포, 건조, 노광, 및 현상. 상기 컬러필터는 디스플레이 장치, 예컨대 액정 디스플레이 장치, 발광 디스플레이 장치, 또는 고상 이미지 센서 장치(solid-state image sensing device), 예컨대 전하결합 장치(charge coupled device) 등의 제조에 적용될 수 있다. The present invention also relates to a color filter comprising the compound or colorant material of the present invention. Such a color filter can be manufactured through a lithographic method, especially through the following steps: preparing a composition for forming a color filter by combining the mill base composition according to the present invention with additional components, applying this composition to a substrate, drying, Exposure, and development. The color filter may be applied to the manufacture of display devices, such as liquid crystal display devices, light-emitting display devices, or solid-state image sensing devices, such as charge coupled devices.
따라서, 본 발명은 또한 본 발명의 화합물 또는 컴플렉스의 착색제로서의 용도, 바람직하게는 황색 착색제로서의 용도, 및 본 발명의 화합물, 컴플렉스, 또는 착색제 물질의 컬러필터 제조에서의 용도, 특히 컬러필터의 녹색 또는 적색부를 형성하는 데 있어서의 용도에 관한 것이다.Accordingly, the present invention also relates to the use of the compounds or complexes of the invention as colorants, preferably as yellow colorants, and to the use of the compounds, complexes or colorant materials of the invention in the production of color filters, especially as green or colorant materials in color filters. It relates to use in forming red areas.
본 발명의 추가적인 일 측면은 하기 화학식 3의 화합물에 관한 것이다:A further aspect of the invention relates to compounds of formula 3:
상기 화학식 3에서, Y는 상기 정의된 관능기이고, R9 내지 R14는 퀴놀린 골격 구조체의 치환기이며, 바람직하게는 독립적으로 수소, 할로겐, 알킬기, 아릴기, 알킬 에스테르, 아릴 에스테르, -SO3 -M+, -COO-M+, -COH, -C(O)NR'R", -S(O)2NR'R", -NO2, 및 -NR'R" (여기서 M+는 독립적으로 양이온이고, R' 및 R"는 독립적으로 수소, 알킬기 또는 아릴기로부터 선택되거나, R' 및 R"는 서로 결합하여 단환 또는 다환 구조를 형성할 수 있음)로 구성되는 군으로부터 선택될 수 있다. 특히 바람직한 실시태양에서, 상기 화학식 3 중 R14는 메틸기이고, R9는 아미노기 또는 니트로기이며, 나머지 R10, R11, R12 및 R13은 모두 수소이다.In Formula 3, Y is a functional group defined above, and R9 to R14 are substituents of the quinoline skeletal structure, preferably independently hydrogen, halogen, alkyl group, aryl group, alkyl ester, aryl ester, -SO 3 - M + , -COO - M + , -COH, -C(O)NR'R", -S(O) 2 NR'R", -NO 2 , and -NR'R" (where M + is independently a cation and , R' and R" may be independently selected from hydrogen, an alkyl group, or an aryl group, or R' and R" may be combined with each other to form a monocyclic or polycyclic structure. Particularly preferred are: In an embodiment, in Formula 3, R14 is a methyl group, R9 is an amino group or a nitro group, and the remaining R10, R11, R12, and R13 are all hydrogen.
본원에 참조로 통합된 모든 특허, 특허출원 및 공개문헌의 개시물이 용어를 불명확하게 만들 수 있는 범위까지 본 출원의 명세서와 대립되면, 본 명세서가 우선한다.To the extent that the disclosure of any patent, patent application, or publication incorporated herein by reference conflicts with the specification of this application to the extent that it may render terms unclear, this specification shall control.
하기 실시예를 들어 본 발명을 좀 더 구체적으로 설명하는 바, 이에 본 발명의 범주가 실시예의 특별한 형태에 한정되는 것은 아니며 명백한 형태 및 변형을 포함하는 것으로 해석되어야 한다.The present invention will be described in more detail with reference to the following examples, and the scope of the present invention is not limited to the specific form of the examples and should be construed to include obvious forms and modifications.
실시예Example
실시예 1: 술폰화된 8-아미노퀴날딘 중간체를 통한 화합물 1의 제조Example 1: Preparation of Compound 1 via Sulfonated 8-Aminoquinaldine Intermediate
8-니트로퀴날딘(1 g, 5.31 mmol)을 H2SO4(2.83 ml, 53.1 mmol)에 첨가하고, 70 ℃에서 8 시간 동안 교반하였다. 반응 후, 온도를 상온으로 내렸다. 얻어진 혼합물을 H2O(280 ml)에 천천히 첨가하였다. 침전된 물질을 여과하고 수세하여 술폰화된 8-니트로퀴날딘을 얻었다.8-Nitroquinaldine (1 g, 5.31 mmol) was added to H 2 SO 4 (2.83 ml, 53.1 mmol) and stirred at 70° C. for 8 hours. After reaction, the temperature was lowered to room temperature. The resulting mixture was slowly added to H 2 O (280 ml). The precipitated material was filtered and washed with water to obtain sulfonated 8-nitroquinaldine.
상기와 같이 하여 얻어진 술폰화된 8-니트로퀴날딘(1 g, 3.72 mmol)을 EtOH(10 ml) 중에 용해하고, 거기에 Fe(1.04 g, 18.63 mmol)을 첨가하였다. 농염산(10 ml)을 서서히 첨가하였다. 얻어진 혼합물을 2 시간 동안 환류하였다. 온도를 상온으로 되돌렸다. DCM(20 ml) 및 포화 NaHCO3(20 ml)를 서서히 도입하고, 셀라이트 필터로 여과하였다. 여과한 용액을 추출하였다. 유기층을 MgSO4로 건조시키고 여과하였다. 감압하에 농축하여 술폰화된 8-아미노퀴날딘을 얻었다.Sulfonated 8-nitroquinaldine (1 g, 3.72 mmol) obtained as above was dissolved in EtOH (10 ml), and Fe (1.04 g, 18.63 mmol) was added thereto. Concentrated hydrochloric acid (10 ml) was added slowly. The resulting mixture was refluxed for 2 hours. The temperature was returned to room temperature. DCM (20 ml) and saturated NaHCO 3 (20 ml) were slowly introduced and filtered through Celite filter. The filtered solution was extracted. The organic layer was dried with MgSO 4 and filtered. Concentration under reduced pressure gave sulfonated 8-aminoquinaldine.
화합물 1Compound 1
벤조산(9.22 g, 75.54 mmol)을 플라스크에 도입하고, 온도를 140 ℃로 승온하였다. 상기 술폰화된 8-아미노퀴날딘(1 g, 4.19 mmol) 및 4-tert-부틸 무수프탈산(1.71 g, 8.39 mmol)을 첨가하고, 28 시간 동안 교반하였다. 온도를 상온으로 낮추고 DCM(100 ml) 및 2N NaOH로 추출하였다. 유기층을 MgSO4로 건조시키고, 셀라이트를 이용하여 여과하였다. 감압하에 농축하고 SiO2 컬럼(Hex:EA=5:1 내지 2:1)으로 처리하여 상기 화합물 1을 얻었다.Benzoic acid (9.22 g, 75.54 mmol) was introduced into the flask, and the temperature was raised to 140°C. The sulfonated 8-aminoquinaldine (1 g, 4.19 mmol) and 4- tert -butyl phthalic anhydride (1.71 g, 8.39 mmol) were added and stirred for 28 hours. The temperature was lowered to room temperature and extracted with DCM (100 ml) and 2N NaOH. The organic layer was dried with MgSO 4 and filtered using Celite. Concentrated under reduced pressure and treated with SiO 2 column (Hex:EA=5:1 to 2:1) to obtain Compound 1.
실시예 2: 퀴노프탈론 구조체의 술폰화를 통한 화합물 1의 제조Example 2: Preparation of Compound 1 through sulfonation of quinophthalone structure
8-니트로퀴날딘(50 g, 256.7 mmol)을 EtOH(500 ml) 중에 용해하고, 거기에 Fe(74.19 g, 1328.5 mmol)을 첨가하였다. 농염산(100 ml)을 서서히 첨가하였다. 얻어진 혼합물을 2 시간 동안 환류하였다. 온도를 상온으로 되돌렸다. DCM(200 ml) 및 포화 NaHCO3(200 ml)를 서서히 도입하고, 셀라이트 필터로 여과하였다. 여과한 용액을 추출하였다. 유기층을 MgSO4로 건조시키고 여과하였다. 감압하에 농축하여 8-아미노퀴날딘을 얻었다.8-Nitroquinaldine (50 g, 256.7 mmol) was dissolved in EtOH (500 ml) and Fe (74.19 g, 1328.5 mmol) was added thereto. Concentrated hydrochloric acid (100 ml) was added slowly. The resulting mixture was refluxed for 2 hours. The temperature was returned to room temperature. DCM (200 ml) and saturated NaHCO 3 (200 ml) were slowly introduced and filtered through Celite filter. The filtered solution was extracted. The organic layer was dried with MgSO 4 and filtered. Concentrated under reduced pressure to obtain 8-aminoquinaldine.
벤조산(97 g, 796 mmol)을 플라스크에 도입하고, 온도를 140 ℃로 승온하였다. 8-아미노퀴날딘(7 g, 44.24 mmol) 및 4-tert-부틸 무수프탈산(18.07 g, 88.5 mmol)을 첨가하고, 28 시간 동안 교반하였다. 온도를 상온으로 낮추고 DCM(100 ml) 및 2N NaOH로 추출하였다. 유기층을 MgSO4로 건조시키고, 셀라이트를 이용하여 여과하였다. 감압하에 농축하고 SiO2 컬럼(Hex:EA=5:1 내지 2:1)으로 처리하여 하기 중간체 화합물을 얻었다.Benzoic acid (97 g, 796 mmol) was introduced into the flask, and the temperature was raised to 140°C. 8-Aminoquinaldine (7 g, 44.24 mmol) and 4- tert -butyl phthalic anhydride (18.07 g, 88.5 mmol) were added and stirred for 28 hours. The temperature was lowered to room temperature and extracted with DCM (100 ml) and 2N NaOH. The organic layer was dried with MgSO 4 and filtered using Celite. It was concentrated under reduced pressure and treated with a SiO 2 column (Hex:EA=5:1 to 2:1) to obtain the following intermediate compound.
상기 얻어진 중간체 화합물(1 g, 1.88 mmol)을 H2SO4(0.1 ml, 1.88 mmol)에 첨가하고, 70 ℃에서 8 시간 동안 교반하였다. 반응 후, 온도를 상온으로 내렸다. 얻어진 혼합물을 H2O(280 ml)에 천천히 첨가하였다. 침전된 물질을 여과하고 수세하여 상기 화합물 1을 얻었다.The obtained intermediate compound (1 g, 1.88 mmol) was added to H 2 SO 4 (0.1 ml, 1.88 mmol), and stirred at 70° C. for 8 hours. After reaction, the temperature was lowered to room temperature. The resulting mixture was slowly added to H 2 O (280 ml). The precipitated material was filtered and washed with water to obtain Compound 1.
실시예 3: 화합물 1과 중합체 분산제 간의 컴플렉스화Example 3: Complexation between Compound 1 and Polymeric Dispersant
상기 화합물 1(1 g)을 MeOH(10 ml) 중에 용해하였다. 분산제인 BYK-2000(1 g, BYK CHEMIE로부터 구매 가능)을 MeOH(1 ml) 중에 용해하여, 상기 화합물 1의 용액에 서서히 첨가하였다. 혼합물을 상온에서 1 시간 동안 교반하고, H2O(100 ml)에 서서히 첨가하였다. 침전된 물질을 여과하고 수세하고, 진공오븐에서 건조하여 컴플렉스화된 화합물을 얻었다.Compound 1 (1 g) was dissolved in MeOH (10 ml). The dispersant BYK-2000 (1 g, available from BYK CHEMIE) was dissolved in MeOH (1 ml) and slowly added to the solution of Compound 1 above. The mixture was stirred at room temperature for 1 hour and slowly added to H 2 O (100 ml). The precipitated material was filtered, washed with water, and dried in a vacuum oven to obtain a complexed compound.
실시예 4: 황색 착색제 밀베이스 1의 제조Example 4: Preparation of yellow colorant Millbase 1
실시예 1로부터 얻어진 상기 화합물 3 g, TERPLUS D1160 (오츠카케미컬사로부터 구매 가능함) 4 g, 및 PGME 43 g을 비드밀에 도입한 후, 지르코니아 비드 (크기: 0.05~2 mm)를 사용하여 40 ℃에서 6~8 시간 동안 교반하여 상기 황색 착색제 밀베이스 1을 얻었다.3 g of the above compound obtained from Example 1, 4 g of TERPLUS D1160 (available from Otsuka Chemical), and 43 g of PGME were introduced into a bead mill, and then milled at 40° C. using zirconia beads (size: 0.05 to 2 mm). The yellow colorant Millbase 1 was obtained by stirring for 6 to 8 hours.
실시예 5: 황색 착색제 밀베이스 2의 제조Example 5: Preparation of yellow colorant Millbase 2
실시예 3로부터 얻어진 상기 컴플렉스화된 화합물 3 g, TERPLUS D1160 (오츠카케미컬사로부터 구매 가능함) 4 g, 및 PGME 43 g을 비드밀에 도입한 후, 지르코니아 비드 (크기: 0.05~2 mm)를 사용하여 40 ℃에서 6~8 시간 동안 교반하여 상기 황색 착색제 밀베이스 2를 얻었다.3 g of the complexed compound obtained from Example 3, 4 g of TERPLUS D1160 (available from Otsuka Chemical), and 43 g of PGME were introduced into a bead mill, and then zirconia beads (size: 0.05 to 2 mm) were used. The mixture was stirred at 40°C for 6 to 8 hours to obtain the yellow colorant Millbase 2.
성능 테스트performance test
(1) 필름의 제조: 상기 황색 착색제 밀베이스를 스핀 코팅(200~300 rpm으로 15초)을 통해 유리 기판(EAGLE-XG FUSION GLASS; 코닝(CORNING)사로부터 구매 가능함)상에 코팅하여 약 2 마이크론 두께의 필름을 형성하고, 90 ℃에서 90초 동안 프리-베이킹(pre-baking)하였다. 그 후, 상기 필름을 230 ℃에서 20분 동안 1차 포스트 베이킹(post baking)하였다. 이어서, 상기 필름을 230 ℃에서 60분 동안 2차 포스트 베이킹하였다. 그 후, 상기 필름을 400 W/m2의 세기로 20시간 동안 광 조사(UV 조사)하였다.(1) Preparation of film: The yellow colorant mill base is coated on a glass substrate (EAGLE-XG FUSION GLASS; available from Corning) through spin coating (200-300 rpm for 15 seconds) to give about 2 A micron-thick film was formed and pre-baked at 90° C. for 90 seconds. Afterwards, the film was first post-baked at 230°C for 20 minutes. The film was then post-baked a second time at 230°C for 60 minutes. Afterwards, the film was irradiated with light (UV irradiation) at an intensity of 400 W/m 2 for 20 hours.
(2) 색 및 휘도(brightness)의 측정: 상기 필름에 대하여 Otsuka Photal MCPD 3000 색도계(colorimeter)를 이용하여 분광 측정하여 x 및 y 색좌표와 휘도(Y)를 얻었다. ΔE*ab는 각 포스트 베이킹 공정의 전후 값을 비교함으로써 측정하였다.(2) Measurement of color and brightness: The film was subjected to spectral measurement using an Otsuka Photal MCPD 3000 colorimeter to obtain x and y color coordinates and brightness (Y). ΔE*ab was measured by comparing the values before and after each post-baking process.
(3) 콘트라스트의 측정: 상기 1차 포스트 베이킹 공정 후 콘트라스트 테스터인 Tsubosaka CT-1 (30,000:1)을 사용하여 콘트라스트를 측정하였다.(3) Measurement of contrast: After the first post-baking process, the contrast was measured using a contrast tester, Tsubosaka CT-1 (30,000:1).
Claims (15)
<화학식 1>
(여기서
X는 독립적으로 수소 또는 할로겐이고;
Y는 -SO3 -M+ 이며, 여기서 M+는 독립적으로 양이온이고;
R1 내지 R8은 독립적으로 수소 또는 알킬기이고;
R1 내지 R8 중 적어도 하나 이상의 탄소수가 3개 이상임)A complex of a compound of formula (1) and one or more cationic polymer based dispersants:
<Formula 1>
(here
X is independently hydrogen or halogen;
Y is -SO 3 - M + , where M + is independently a cation;
R1 to R8 are independently hydrogen or an alkyl group;
At least one of R1 to R8 has 3 or more carbon atoms)
<화학식 1a>
<Formula 1a>
<화학식 2>
(여기서 각 X 및 R1 내지 R8은 상기 청구항 1에서와 동일한 의미를 가짐)According to any one of claims 1 and 3 to 5, comprising preparing the compound by reacting one or more substituted or unsubstituted 8-quinaldine or a compound of formula 2 below with one or more functionalizing agents. Preparation method of the complex according to:
<Formula 2>
(where each X and R1 to R8 have the same meaning as in claim 1 above)
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