KR101347850B1 - Pigment derivatives, pigment dispersion composition, color resist, and color filter - Google Patents
Pigment derivatives, pigment dispersion composition, color resist, and color filter Download PDFInfo
- Publication number
- KR101347850B1 KR101347850B1 KR1020110019250A KR20110019250A KR101347850B1 KR 101347850 B1 KR101347850 B1 KR 101347850B1 KR 1020110019250 A KR1020110019250 A KR 1020110019250A KR 20110019250 A KR20110019250 A KR 20110019250A KR 101347850 B1 KR101347850 B1 KR 101347850B1
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- KR
- South Korea
- Prior art keywords
- hetero
- substituted
- unsubstituted
- carbon atoms
- pigment
- Prior art date
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- 239000000049 pigment Substances 0.000 title claims abstract description 154
- 239000000203 mixture Substances 0.000 title claims abstract description 61
- 239000006185 dispersion Substances 0.000 title claims abstract description 52
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 98
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 72
- 239000012860 organic pigment Substances 0.000 claims abstract description 27
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims abstract description 20
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims abstract description 19
- 125000003277 amino group Chemical group 0.000 claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 9
- 239000000126 substance Substances 0.000 claims abstract description 7
- 239000003960 organic solvent Substances 0.000 claims description 11
- 239000000463 material Substances 0.000 claims description 8
- 238000003860 storage Methods 0.000 claims description 6
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 5
- 150000004056 anthraquinones Chemical class 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 150000001721 carbon Chemical class 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims description 3
- 125000005264 aryl amine group Chemical group 0.000 claims description 3
- FYNROBRQIVCIQF-UHFFFAOYSA-N pyrrolo[3,2-b]pyrrole-5,6-dione Chemical class C1=CN=C2C(=O)C(=O)N=C21 FYNROBRQIVCIQF-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000011521 glass Substances 0.000 abstract description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 22
- 229920005989 resin Polymers 0.000 description 21
- 239000011347 resin Substances 0.000 description 21
- 238000000034 method Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 230000015572 biosynthetic process Effects 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- 239000002270 dispersing agent Substances 0.000 description 13
- 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 description 11
- BCXSVFBDMPSKPT-UHFFFAOYSA-N 5-amino-1,3-dihydrobenzimidazol-2-one Chemical compound NC1=CC=C2NC(=O)NC2=C1 BCXSVFBDMPSKPT-UHFFFAOYSA-N 0.000 description 11
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 11
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 11
- MGNCLNQXLYJVJD-UHFFFAOYSA-N cyanuric chloride Chemical compound ClC1=NC(Cl)=NC(Cl)=N1 MGNCLNQXLYJVJD-UHFFFAOYSA-N 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 238000002156 mixing Methods 0.000 description 10
- 239000012467 final product Substances 0.000 description 9
- 239000002245 particle Substances 0.000 description 8
- 239000011324 bead Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 235000002639 sodium chloride Nutrition 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000003801 milling Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- -1 polypropylene chlorides Polymers 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 150000002430 hydrocarbons Chemical class 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 239000004925 Acrylic resin Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical class [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- 229920000178 Acrylic resin Polymers 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 125000004104 aryloxy group Chemical group 0.000 description 2
- 238000000889 atomisation Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000011247 coating layer Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 239000001056 green pigment Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- GWVMLCQWXVFZCN-UHFFFAOYSA-N isoindoline Chemical compound C1=CC=C2CNCC2=C1 GWVMLCQWXVFZCN-UHFFFAOYSA-N 0.000 description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- PGMYKACGEOXYJE-UHFFFAOYSA-N pentyl acetate Chemical compound CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 2
- 229920006122 polyamide resin Polymers 0.000 description 2
- 229920001721 polyimide Polymers 0.000 description 2
- 239000009719 polyimide resin Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011164 primary particle Substances 0.000 description 2
- 239000001057 purple pigment Substances 0.000 description 2
- 239000001054 red pigment Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 description 2
- 239000002966 varnish Substances 0.000 description 2
- 239000001052 yellow pigment Substances 0.000 description 2
- MJQHDSIEDGPFAM-UHFFFAOYSA-N (3-benzoylphenyl)-phenylmethanone Chemical compound C=1C=CC(C(=O)C=2C=CC=CC=2)=CC=1C(=O)C1=CC=CC=C1 MJQHDSIEDGPFAM-UHFFFAOYSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NBUKAOOFKZFCGD-UHFFFAOYSA-N 2,2,3,3-tetrafluoropropan-1-ol Chemical compound OCC(F)(F)C(F)F NBUKAOOFKZFCGD-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- PTTPXKJBFFKCEK-UHFFFAOYSA-N 2-Methyl-4-heptanone Chemical compound CC(C)CC(=O)CC(C)C PTTPXKJBFFKCEK-UHFFFAOYSA-N 0.000 description 1
- QEZGRWSAUJTDEZ-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperidine-1-carbonyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)C(=O)N1CCCCC1 QEZGRWSAUJTDEZ-UHFFFAOYSA-N 0.000 description 1
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- 150000001346 alkyl aryl ethers Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
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- PQJKLTRMSHJEEN-UHFFFAOYSA-N anthracene-1,5-dione Chemical compound O=C1C=CC=C2C=C3C(=O)C=CC=C3C=C21 PQJKLTRMSHJEEN-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
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- MYONAGGJKCJOBT-UHFFFAOYSA-N benzimidazol-2-one Chemical group C1=CC=CC2=NC(=O)N=C21 MYONAGGJKCJOBT-UHFFFAOYSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 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
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000001055 blue pigment Substances 0.000 description 1
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000005018 casein Substances 0.000 description 1
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0034—Mixtures of two or more pigments or dyes of the same type
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
-
- 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
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
- C09B67/0084—Dispersions of dyes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01G—CAPACITORS; CAPACITORS, RECTIFIERS, DETECTORS, SWITCHING DEVICES, LIGHT-SENSITIVE OR TEMPERATURE-SENSITIVE DEVICES OF THE ELECTROLYTIC TYPE
- H01G9/00—Electrolytic capacitors, rectifiers, detectors, switching devices, light-sensitive or temperature-sensitive devices; Processes of their manufacture
- H01G9/20—Light-sensitive devices
- H01G9/2059—Light-sensitive devices comprising an organic dye as the active light absorbing material, e.g. adsorbed on an electrode or dissolved in solution
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/542—Dye sensitized solar cells
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Physics & Mathematics (AREA)
- Power Engineering (AREA)
- Dispersion Chemistry (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Materials Engineering (AREA)
- Microelectronics & Electronic Packaging (AREA)
- Optical Filters (AREA)
Abstract
본 발명은 하기의 화학식 1로 표현되는 안료 유도체와 유리 안료를 포함한 안료 분산 조성물, 컬러 레지스트 조성물 및 컬러필터를 제공한다.
<화학식 1>
(상기 식에서, Q는 유기 색소 잔기이며, R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X1은 헤테로원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합되어 구성된다.)The present invention provides a pigment dispersion composition, a color resist composition, and a color filter including a pigment derivative represented by the following Chemical Formula 1 and a glass pigment.
≪ Formula 1 >
(Wherein Q is an organic pigment residue, and R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms) , A substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, X 1 is a hetero element, a substituted or unsubstituted (hetero) aromatic hydrocarbon having 1 to 60 carbon atoms, substituted or unsubstituted C 1 ~ Consisting of covalently bonded one or more combinations of 60 (hetero) aliphatic hydrocarbons.)
Description
본 발명은 안료 유도체, 안료 분산 조성물, 컬러 레지스트 및 이를 이용하여 제조된 컬러필터에 관한 것이다.
The present invention relates to a pigment derivative, a pigment dispersion composition, a color resist and a color filter prepared using the same.
액정컬러디스플레이, 촬상소자 등의 제조에 사용되는 컬러필터는 감광성 수지액 중에 적색(R), 녹색(G), 및 청색(B)의 삼색의 안료를 각각 분산시킨 컬러필터용 안료 분산 조성물을 도포하여 착색피막을 형성하고, 착색피막에 포토마스크를 이용하여 노광, 현상하여 착색피막을 패턴화하는 방식으로 원하는 화소를 형성하는 방법으로 제조된다.Color filters used in the manufacture of liquid crystal color displays, imaging devices, and the like are coated with a pigment dispersion composition for color filters in which three pigments of red (R), green (G), and blue (B) are respectively dispersed in the photosensitive resin liquid. It is manufactured by a method of forming a desired pixel by forming a colored film, and exposing and developing the colored film using a photomask to pattern the colored film.
컬러필터용 안료 분산 조성물에 요구되는 특성으로는 고휘도, 착색력 및 고명암비 등의 우수한 광학적 성질과 분산성, 저장안정성이 요구된다. 이러한 특성을 만족시키기 위한 안료 분산 조성물을 제조하기 위해서는 100nm 이하의 미세한 안료입자가 균일한 분포도를 가지며 분산되어야 한다.As the characteristics required for the pigment dispersion composition for color filters, excellent optical properties such as high brightness, color power, and high contrast ratio, dispersibility, and storage stability are required. In order to prepare a pigment dispersion composition for satisfying these characteristics, fine pigment particles of 100 nm or less should be dispersed with a uniform distribution.
컬러필터용 안료 분산 조성물에 적합한 미세 안료를 얻기 위한 종래의 주요 기술로 소금을 이용하여 안료 입자를 미세화시키는 솔트 밀링(salt milling)이 있으며, 이 방법을 이용하여 원하는 입도와 분포도를 갖는 미세 안료를 제조하여 고휘도, 착색력 및 고명암비 등의 광학적 성질을 향상시켜왔다. 그러나, 안료가 미세화되면 안료 입자 자체의 재응집력이 강해져, 안료의 분산성 및 분산 안정성이 나빠지게 되어 문제된다. 이를 해결하기 위해, 분산제 등을 사용한 기술도 알려져 있지만, 상기 용도에서 요구되는 특성을 얻기에는 아직 불충분하다. Conventional main techniques for obtaining fine pigments suitable for pigment dispersion compositions for color filters include salt milling, in which salt particles are refined using salt, and fine pigments having a desired particle size and distribution can be obtained using this method. To improve optical properties such as high brightness, coloring power and high contrast ratio. However, when the pigment becomes finer, the reagglomeration power of the pigment particles themselves becomes strong, and the dispersibility and dispersion stability of the pigment become poor, which is a problem. In order to solve this problem, a technique using a dispersant or the like is also known, but it is still insufficient to obtain the characteristics required for the above-mentioned use.
따라서, 고휘도, 착색력 및 고명암비 등의 광학적 성질을 만족할 뿐만 아니라 고분산성 및 분산 안정성을 충분히 만족시킬 수 있는 안료 분산 조성물의 개발이 요구된다.
Therefore, there is a need for the development of a pigment dispersion composition which not only satisfies optical properties such as high brightness, coloring power, and high contrast ratio, but also sufficiently satisfies high dispersion and dispersion stability.
상기의 과제를 해결하기 위해 본 발명은, 휘도, 명암비 등의 광학적 성질과 분산성 및 분산 안정성을 만족시킬 수 있는 안료 유도체, 안료 분산 조성물, 상기 안료 분산 조성물을 포함한 컬러 레지스트 조성물 및 상기 컬러 레지스트 조성물을 이용한 컬러필터를 제공하는 것을 목적으로 한다.
In order to solve the above problems, the present invention provides a pigment derivative, a pigment dispersion composition, a color resist composition including the pigment dispersion composition and the color resist composition capable of satisfying optical properties such as brightness, contrast ratio, and dispersibility and dispersion stability. It is an object to provide a color filter using.
상기의 과제를 해결하기 위한 수단으로서, As means for solving the above problem,
본 발명은 하기의 화학식 1로 표현되는 안료 유도체를 제공한다.The present invention provides a pigment derivative represented by the following formula (1).
<화학식 1>≪ Formula 1 >
(상기 식에서, Q는 유기 색소 잔기이며, R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X1은 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.)
(Wherein Q is an organic pigment residue, and R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms) , A substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, X 1 is a hetero element, a substituted or unsubstituted (hetero) aromatic hydrocarbon having 1 to 60 carbon atoms, substituted or unsubstituted C 1 ~ Consisting of covalently bonded one or more combinations of 60 (hetero) aliphatic hydrocarbons.)
또한, 하기의 화학식 2로 표현되는 안료 유도체를 제공한다.In addition, it provides a pigment derivative represented by the following formula (2).
<화학식 2>(2)
(상기 식에서, Q는 유기 색소 잔기이며, R4는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알콕시기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴록시기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬아민기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴아민기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로)지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.)
(Wherein Q is an organic pigment residue and R 4 is each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 60 carbon atoms, substituted or unsubstituted) A (hetero) aryl group having 3 to 60 carbon atoms, a substituted or unsubstituted (hetero) alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) aryloxy group having 3 to 60 carbon atoms, a substituted or unsubstituted carbon number A (hetero) alkylamine group of 1 to 60, a substituted or unsubstituted (hetero) arylamine group of 3 to 60 carbon atoms, X 2 is -NH-, -O-, or -SO 2 NH- or hetero And is covalently bonded to one or more combinations of an elemental, substituted or unsubstituted (hetero) aromatic hydrocarbon having 1 to 60 carbon atoms, or a substituted or unsubstituted (hetero) aliphatic hydrocarbon having 1 to 60 carbon atoms, X 3 is -NH- of, -O-, or -SO 2 NH- or a hetero atom, a substituted or unsubstituted 1 to 20 carbon atoms in the (hetero) Among hyangjok hydrocarbon, (hetero) aliphatic hydrocarbon group of the substituted or unsubstituted 1 to 30 carbon atoms consists of the covalent bond with one or more combination thereof.)
또한, 하기의 화학식 3으로 표현되는 안료 유도체를 제공한다.In addition, it provides a pigment derivative represented by the following formula (3).
<화학식 3><Formula 3>
(상기 식에서, R5, R6, R7은 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.
Wherein R 5 , R 6 , and R 7 each independently represent a halogen, an amine group, a cyano group, a nitro group, a substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted C 3 to Selected from 30 (hetero) aryl groups, X 2 is -NH-, -O-, or -SO 2 NH- or a hetero atom, a substituted or unsubstituted (hetero) aromatic hydrocarbon having 1 to 60 carbon atoms, substituted or It is composed of one or more combinations of unsubstituted (hetero) aliphatic hydrocarbons having 1 to 60 carbon atoms, covalently bonded, X 3 , X 4 are each independently -NH-, -O-, or -SO 2 NH- or a hetero element, Or a covalently bonded one or more combinations of substituted or unsubstituted (hetero) aromatic hydrocarbons having 1 to 20 carbon atoms and substituted or unsubstituted (hetero) aliphatic hydrocarbons having 1 to 30 carbon atoms.
또한, 하기의 화학식 4로 표현되는 안료 유도체를 제공한다.In addition, it provides a pigment derivative represented by the following formula (4).
<화학식 4>≪ Formula 4 >
(상기 식에서, R5, R6, R7, R8, R9는 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.)
(Wherein R 5 , R 6 , R 7 , R 8 , R 9 are each independently halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or An unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, and X 3 and X 4 are each independently -NH-, -O-, or -SO 2 NH- or a hetero atom, a substituted or unsubstituted carbon number 1 Composed of covalently bonded one or more combinations of (hetero) aromatic hydrocarbons of ˜20, substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 30 carbon atoms.)
또한, 상기 유기 색소 잔기는 안트라퀴논계, 디안트라퀴논계(Red 177을 포함), 디케토피롤로피롤계(Orange 71, Orange 73, Red 254, Red 255, Red 264, Red 272를 포함), 퀴노프탈론계(Yellow 138을 포함) 중에서 선택되는 것을 특징으로 하는 안료 유도체를 제공한다.
In addition, the organic pigment residue is an anthraquinone-based, dianthraquinone-based (including Red 177), diketopyrrolopyrrole-based (including Orange 71, Orange 73, Red 254, Red 255, Red 264, Red 272), It provides a pigment derivative characterized in that it is selected from nophthalone-based (including Yellow 138).
본 발명은 또한, 상기 안료 유도체 및 유기 안료를 포함하여 이루어진 안료 분산 조성물을 제공한다.
The present invention also provides a pigment dispersion composition comprising the pigment derivative and an organic pigment.
본 발명은 또한, 상기 안료 분산 조성물과 감광성 피막 형성 재료를 포함하는 것을 특징으로 하는 컬러 레지스트 조성물을 제공한다.
The present invention also provides a color resist composition comprising the pigment dispersion composition and a photosensitive film forming material.
본 발명은 또한, 상기 컬러 레지스트 조성물을 이용하여 화소가 형성되어 있는 것을 특징으로 하는 컬러필터를 제공한다.
The present invention also provides a color filter, wherein a pixel is formed using the color resist composition.
상기의 구성적 특징을 갖는 본 발명의 안료 유도체를 포함한 안료 분산 조성물은 휘도, 명암비 등의 광학적 성질을 우수하게 유지하면서 동시에 분산성 및 분산 안정성을 제공할 수 있다. 본 발명의 안료 분산 조성물은 컬러 레지스트 조성물 성분으로 포함되어 우수한 컬러필터를 제조할 수 있다.
The pigment dispersion composition including the pigment derivative of the present invention having the above-described structural characteristics can provide dispersibility and dispersion stability while maintaining excellent optical properties such as brightness and contrast ratio. The pigment dispersion composition of the present invention can be included as a color resist composition component to produce an excellent color filter.
이하에서는 실시예를 통해 본 발명을 보다 상세히 설명하기로 한다. 하기의 설명은 본 발명의 구체적 일례에 대한 것이므로, 비록 단정적, 한정적 표현이 있더라도 특허청구 범위로부터 정해지는 권리범위를 제한하는 것은 아니다.
Hereinafter, the present invention will be described in more detail with reference to Examples. The following descriptions are for specific examples of the present invention, but are not intended to limit the scope of the rights defined by the claims, even if there is an assertive or limited expression.
본 발명은 특수 화학구조의 안료 유도체를 제공한다. 또한, 안료 유도체와 유기 안료를 포함하는 것을 특징으로 하는 안료 분산 조성물을 제공한다. 안료 분산 조성물에는 분산제, 수지, 유기용매, 첨가제 등이 선택적으로 더 포함될 수 있다.The present invention provides pigment derivatives of special chemical structure. The present invention also provides a pigment dispersion composition comprising a pigment derivative and an organic pigment. The pigment dispersion composition may optionally further include a dispersant, a resin, an organic solvent, an additive, and the like.
이하 각 성분을 구체적으로 설명한다.
Each component is demonstrated concretely below.
<안료 유도체>Pigment Derivatives
미립화된 안료 입자는 열역학적으로 불안정한 상태이므로 비표면적을 줄이려는 방향으로 응집하려 하는 경향이 있으며, 특히 미립화 과정에서 과도하게 미립화된 초미세입자의 경우 응집하려는 경향이 더욱 크다. 본 발명의 안료 유도체는 특수한 화학구조로 이루어져 있어 미립화된 안료 입자의 재응집을 막는 효과를 나타내어 분산 안정성 및 저장 안정성을 향상시킨다.
Since the granulated pigment particles are thermodynamically unstable, they tend to agglomerate in a direction to reduce the specific surface area, particularly in the case of ultrafine particles that are excessively atomized during the atomization process. The pigment derivative of the present invention is composed of a special chemical structure to exhibit the effect of preventing reaggregation of the atomized pigment particles to improve dispersion stability and storage stability.
본 발명의 일실시예에 따른 안료 유도체는 하기의 화학식 1로 표현되는 화합물로부터 선택되는 적어도 1종의 안료 유도체를 포함하는 것을 특징으로 한다.
Pigment derivative according to an embodiment of the present invention is characterized in that it comprises at least one pigment derivative selected from compounds represented by the following formula (1).
<화학식 1>≪ Formula 1 >
화학식 1의 안료 유도체는 벤조이미다졸론기가 링크 구조를 통해 유기 색소 잔기 Q와 연결되는 것이 특징이다. The pigment derivative of the formula (1) is characterized in that the benzoimidazolone group is linked with the organic pigment residue Q through a linkage structure.
상기 화학식 1에서, Q는 유기 색소 잔기이며, 특별히 제한되지 않으며 일례로는 안트라퀴논계, 디안트라퀴논계(Red 177을 포함), 디케토피롤로피롤계(Orange 71, Orange 73, Red 254, Red 255, Red 264, Red 272를 포함), 퀴노프탈론계(Yellow 138을 포함) 중에서 선택될 수 있다. In Chemical Formula 1, Q is an organic pigment residue, and is not particularly limited. For example, anthraquinone-based, dianthraquinone-based (including Red 177), diketopyrrolopyrrole-based (Orange 71, Orange 73, Red 254, Red) 255, Red 264, Red 272), and quinophthalone-based (including Yellow 138).
R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X1은 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, substituted or unsubstituted having 3 to 30 carbon atoms Selected from a (hetero) aryl group, X 1 is a combination of one or more of hetero elements, substituted or unsubstituted (hetero) aromatic hydrocarbons having 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aliphatic hydrocarbons having 1 to 60 carbon atoms It is composed of covalently bonded.
한편,“(헤테로)”의 의미는 산소, 질소, 황 등의 헤테로 원소로 탄소가 치환되거나 무치환 되는 것을 의미한다.
On the other hand, "(hetero)" means that the carbon is substituted or unsubstituted by a hetero element such as oxygen, nitrogen, sulfur.
상기 화학식 1은 보다 바람직하기로는 하기 화학식 2로 표현되는 화합물인 것이 좋다.
Formula 1 is more preferably a compound represented by the following formula (2).
<화학식 2>(2)
상기 화학식 2에서, Q, R1, R2 및 R3는 화학식 1과 동일하며, R4는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알콕시기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴록시기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬아민기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴아민기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.
In Chemical Formula 2, Q, R 1 , R 2, and R 3 are the same as those of Chemical Formula 1, and R 4 is each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted C1-C60 (Hetero) alkyl group of substituted, unsubstituted or unsubstituted (hetero) aryl group having 3 to 60 carbon atoms, substituted or unsubstituted (hetero) alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted having 3 to 60 carbon atoms (hetero) ) Aryloxy group, a substituted or unsubstituted (hetero) alkylamine group having 1 to 60 carbon atoms, a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms, X 2 is -NH-,- O-, or -SO 2 NH- or a hetero element, covalently bonded in one or more combinations of (hetero) aromatic hydrocarbons of 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 60 carbon atoms, X 3 is —NH—, —O—, or —SO 2 NH— or a hetero atom, substituted or unsubstituted C 1-20 (hetero) Aromatic hydrocarbons, substituted or unsubstituted (hetero) aliphatic hydrocarbons having 1 to 30 carbon atoms are covalently bonded in one or more combinations.
상기 화학식 1은 또한, 하기 화학식 3으로 표현되는 화합물인 것이 좋다.
Formula 1 is also preferably a compound represented by the following formula (3).
<화학식 3><Formula 3>
상기 식에서, Q, R1, R2 및 R3는 화학식 1과 동일하며, R5, R6, R7은 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.
Wherein, Q, R 1 , R 2 and R 3 are the same as those of Formula 1, and R 5 , R 6 and R 7 are each independently halogen, amine group, cyano group, nitro group, substituted or unsubstituted carbon number 1 Or a (hetero) alkyl group of ˜20, a substituted or unsubstituted (hetero) aryl group of 3 to 30 carbon atoms, X 2 is —NH—, —O—, or —SO 2 NH— or a hetero element, substituted or Unsubstituted (hetero) aromatic hydrocarbons of 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 60 carbon atoms, covalently bonded to one or more combinations, each of X 3 and X 4 independently NH-, -O-, or -SO 2 NH- or a hetero atom, substituted or unsubstituted (hetero) aromatic hydrocarbons having 1 to 20 carbon atoms, substituted or unsubstituted (hetero) aliphatic hydrocarbons having 1 to 30 carbon atoms Combination is composed of the above combination.
상기 화학식 1은 또한, 하기 화학식 4로 표현되는 화합물인 것이 좋다. Formula 1 is also preferably a compound represented by the following formula (4).
<화학식 4>≪ Formula 4 >
상기 식에서, Q, R1, R2 및 R3는 화학식 1과 동일하며, R5, R6, R7, R8, R9는 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.
In the above formula, Q, R 1 , R 2 and R 3 are the same as in the general formula (1), R 5 , R 6 , R 7 , R 8 , R 9 are each independently halogen, amine group, cyano group, nitro group, substitution Or an unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, and X 3 and X 4 are each independently -NH-, -O-, Or -SO 2 NH- or a hetero atom, substituted or unsubstituted (hetero) aromatic hydrocarbon of 1 to 20 carbon atoms, covalently bonded in one or more combinations of substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 30 carbon atoms do.
본 발명의 일실시예에 따른 안료 분산 조성물에 있어서, 안료 유도체는 유기안료 100질량부에 대해서 0.1~30질량부의 배합 비율이 바람직하고, 더 바람직하게는 1~20질량부의 배합 비율이 좋다. 상기 안료 유도체의 배합 비율이 너무 적으면, 목적으로 하는 효과를 충분히 얻기 어려워진다. 또한, 상기의 배합 비율이 너무 많아도, 거기에 비례하는 효과는 얻지 못하고, 안료 조성물 및 이를 이용한 착색 조성물의 여러 가지 물성을 저하시켜, 본래의 색상을 크게 변화시켜 버리는 요인이 된다.
In the pigment dispersion composition according to the embodiment of the present invention, the blending ratio of the pigment derivative is preferably 0.1 to 30 parts by mass with respect to 100 parts by mass of the organic pigment, and more preferably 1 to 20 parts by mass. When the compounding ratio of the said pigment derivative is too small, it becomes difficult to fully acquire the target effect. Moreover, even if the said mixing | blending ratio is too much, the effect which is not proportional to it is not acquired, and it becomes a factor which reduces the various physical properties of a pigment composition and the coloring composition using the same, and changes the original color largely.
<안료><Pigment>
안료의 종류에는 특별히 제한되지 않는다. 적색, 녹색, 청색, 황색, 자색 안료 등이 단독 또는 혼합되어 사용될 수 있다. 유기안료로서는, 예를 들면, 아조계 안료, 프탈로시아닌계 안료, 퀴나크리돈계 안료, 페릴렌·페리논계 안료 (perylene/perinone pigments), 이소인돌리논계 안료(isoindolinone pigments), 이소인돌린계 안료(isoindoline pigments), 디옥사진계 안료(dioxazine pigments), 퀴노프탈론계 안료(quinophthalone pigments), 디케토피롤로피롤계 안료(diketopyrrolopyrole pigments), 안트라퀴논계 안료(anthraquinone pigments), 티오인디고계 안료(thioindigo pigments), 금속 착체계 안료(metal complex pigments) 등을 들 수 있지만, 이들에 한정되지 않는다.The kind of pigment is not particularly limited. Red, green, blue, yellow, purple pigments and the like may be used alone or in combination. Examples of the organic pigment include pigments such as azo pigments, phthalocyanine pigments, quinacridone pigments, perylene / perinone pigments, isoindolinone pigments, isoindoline pigments ( isoindoline pigments, dioxazine pigments, quinophthalone pigments, diketopyrrolopyrole pigments, anthraquinone pigments, thioindigo pigments, thioindigo pigments, , Metal complex pigments, and the like, but are not limited thereto.
상기 적색 안료의 경우 C.I. Pigment Red 7, 14, 48:1, 48:2, 48:3, 48:4, 81:1, 81:2, 81:3, 146, 177, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272 등을 사용할 수 있으며, 상기 녹색 안료의 경우 C.I. Pigment Green 7, 10, 36, 37등의 녹색 안료를 사용할 수 있고, 상기 청색 안료의 경우 C.I. Pigment Blue 15:1, 15:2, 15:3, 15:4, 15:6, 16, 80등의 청색 안료를 사용할 수 있으며, 상기 황색 안료의 경우 C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214 등을 사용할 수 있고, 상기 자색 안료의 경우 C.I. Pigment Violet 23, 34, 35, 37 등을 사용할 수 있으며, 이들은 단독으로 또는 2종 이상 혼합하여 사용할 수 있다.C.I. Pigment Red 7, 14, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 146, 177, 184, 185, 187, 200, 202, 208, 210, 246, 254, 255, 264, 270, 272, etc. may be used, and in the case of the green pigment CI Pigment Green 7, 10, 36, 37, such as green pigments can be used, and in the case of the blue pigment C.I. Pigment Blue 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 80 and the like can be used, and the yellow pigment, C.I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 199, 213, 214 and the like can be used, and in the case of the purple pigment CI Pigment Violet 23, 34, 35, 37, etc. can be used, These can be used individually or in mixture of 2 or more types.
특히, 적색 안료 분산 조성물의 경우에는 상기 유기안료가, C.I. 피그먼트 레드 122, C.I. 피그먼트 레드 177, C.I. 피그먼트 레드 254 및 C.I. 피그먼트 바이올렛 19로부터 적어도 하나 이상 선택되는 것이 좋다. In particular, in the case of a red pigment dispersion composition, the organic pigment is C.I. Pigment Red 122, C.I. Pigment Red 177, C.I. Pigment Red 254 and C.I. It is preferred to select at least one from pigment violet 19.
상술한 안료는 상기 안료 유도체로 표면이 개질되는 바, 이는 밀링 등과 같은 분쇄 및 분산 과정을 통해 상기 안료 유도체가 분쇄되어 미립화된 안료의 표면상에 결합하는 것을 의미하며, 이를 통해 상기 안료의 성질을 개선하는 것이 가능해진다. 즉, 상기 안료 유도체는 상기 안료의 표면상에 코팅층을 형성하게 되며, 이는 연속 또는 비연속상의 코팅층을 의미한다. 이와 같은 안료 유도체의 표면층을 통해 상기 안료의 분산 안정성, 저장 안정성 및 컬러특성을 개선하는 것이 가능해진다.The pigment described above is modified on the surface of the pigment derivative, which means that the pigment derivative is pulverized and bound on the surface of the atomized pigment through a grinding and dispersing process such as milling. It is possible to improve. That is, the pigment derivative forms a coating layer on the surface of the pigment, which means a continuous or discontinuous coating layer. Through the surface layer of such a pigment derivative, it becomes possible to improve the dispersion stability, storage stability and color characteristics of the pigment.
상기 안료 유도체의 안료 색소 잔기와 안료는 동일한 계열을 사용하는 것이 좋다. 다만, 반드시 동일할 필요는 없으며, 반드시 동일한 색상을 나타내는 것을 조합할 필요는 없으며, 필요에 따라서는 상이한 색상을 나타내는 물질을 사용하는 것도 가능하다. 즉 적색 안료에 황색 안료 유도체로 표면을 개질하고 색특성을 개선하는 것도 가능하며, 또한 동일한 색상을 갖는 안료 및 안료 유도체를 사용하여 색순도를 개선하는 것도 또한 가능해진다.
It is preferable to use the same series of the pigment coloring residue of the pigment derivative and the pigment. However, it is not always necessary to be the same, and it is not always necessary to combine those which exhibit the same hue, and it is also possible to use a material exhibiting a different hue if necessary. That is, it is possible to modify the surface of the red pigment with a yellow pigment derivative and to improve color characteristics, and also to improve color purity by using pigments and pigment derivatives having the same color.
<분산제><Dispersant>
상기 안료 등을 상기 유기 용매 내에서 분산시키기 위해서는 분산제를 사용하는 것이 바람직하며, 이와 같은 분산제로서는 제한되지 않으나 고분자량 분산제를 사용하는 것이 바람직하다.In order to disperse the pigment or the like in the organic solvent, it is preferable to use a dispersing agent. The dispersing agent is not limited, but it is preferable to use a high molecular weight dispersing agent.
상기 고분자량 분산제로서는 바람직하게는 1,000 내지 100,000 범위내의 중량평균 분자량을 가지는 것을 사용할 수 있으며, 더욱 바람직하게는 10,000 내지 30,000의 중량평균분자량을 갖는 고분자량 분산제를 사용하는 것이 좋다. 이와 같은 고분자량 분산제로서는 시판중인 제품, 예를 들어 상품명 EFKA4046(EFKA사 제조), PB-821(Ajinomoto Fine Techno사 제조), BYK사의 디스퍼빅(DISPERBIK) 160, 161, 162, 163, 164, 182, 184(상품명), 아비시아사(Avecia Limited)의 소르스파스(SOLSPERSE) 22000, 24000, 28000(상품명), 쿠스모토 화성사의 디스바론(DISPARLON) DA-234, 325, 375, 725(상품명) 등을 들 수 있지만, 이들에 한정되지 않는다.As the high molecular weight dispersant, preferably those having a weight average molecular weight in the range of 1,000 to 100,000 can be used, and more preferably, a high molecular weight dispersant having a weight average molecular weight of 10,000 to 30,000 is used. As such a high molecular weight dispersant, a commercially available product, for example, trade names EFKA4046 (manufactured by EFKA), PB-821 (manufactured by Ajinomoto Fine Techno), BYPER's DISPERBIK 160, 161, 162, 163, 164, 182 , 184 (brand name), SOLVESSE 22000, 24000, 28000 (brand name) of Avecia Limited, DISPARLON DA-234, 325, 375, 725 (brand name) of Kusumoto Kasei Corporation Although these etc. are mentioned, It is not limited to these.
이와 같은 고분자량 분산제는 제한되지 않으나 상기 안료 100중량부에 대하여 1 내지 30중량부의 함량으로 사용할 수 있다. 상기 분산제 함량이 1중량부 미만이면 충분한 분산 효과를 얻을 수 없고, 30중량부를 초과하는 경우 경제성이 저하되어 바람직하지 않다.
Such a high molecular weight dispersant is not limited but may be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the pigment. If the dispersant content is less than 1 part by weight, a sufficient dispersing effect cannot be obtained, and if it exceeds 30 parts by weight, economical efficiency is lowered, which is not preferable.
<수지><Resin>
안료 분산 조성물에는 수지가 더 포함될 수 있다. 일례로는 페트롤륨 수지, 카세인, 쉘락, 로진-변성 말레산 수지, 로진-변성페놀수지, 니트로셀룰로오스, 셀룰로오스아세테이트 부티레이트, 고리화 고무, 염소화 고무, 산화 고무, 염산 고무, 페놀 수지, 알키드 수지, 폴리에스테르 수지, 불포화 폴리에스테르 수지, 아미노 수지, 에폭시 수지, 비닐 수지, 염화 비닐, 염화비닐-비닐 아세테이트 공중합체, 아크릴 수지, 메타크릴 수지, 폴리우레탄 수지, 실리콘 수지, 플루오르 수지, 건성유, 합성건성유, 스티렌-변성 말레산 수지, 폴리아미드 수지, 폴리이미드 수지, 벤조구안아민 수지, 멜라민 수지, 우레아 수지 염화폴리프로필렌, 부티랄 수지 및 염화 비닐리덴 수지를 포함한다.The pigment dispersion composition may further include a resin. Examples include petroleum resin, casein, shellac, rosin-modified maleic acid resin, rosin-modified phenolic resin, nitrocellulose, cellulose acetate butyrate, cyclized rubber, chlorinated rubber, oxidized rubber, hydrochloric acid rubber, phenolic resin, alkyd resin, Polyester resin, unsaturated polyester resin, amino resin, epoxy resin, vinyl resin, vinyl chloride, vinyl chloride-vinyl acetate copolymer, acrylic resin, methacryl resin, polyurethane resin, silicone resin, fluorine resin, dry oil, synthetic dry oil , Styrene-modified maleic acid resins, polyamide resins, polyimide resins, benzoguanamine resins, melamine resins, urea resin polypropylene chlorides, butyral resins and vinylidene chloride resins.
나아가, 감광 수지가 수지로서 사용될 수 있다. 상기 감광수지로써, 예를 들어, 이소시아네이트기, 알데히드기 또는 에폭시기 또는 신남산 와 같은 반응성 치환체를 갖는 (메트)아크릴 화합물 및 상기 선형 중합체 사이의 반응에 의한 하이드록시기, 카르복시기 또는 아미노기와 같은 반응성 치환체를 갖는 선형 중합체에 (메트)아크릴로일기 또는 스티릴기와 같은 광가교성기를 도입하여 얻어지는 수지 및 스티렌-말레산 무수물 공중합체 또는 α-올레핀-말레산 무수물 공중합체와 같은 산 무수물을 함유하는 선형 중합체와 하이드록시알킬 (메트)아크릴레이트와 같은 하이드록시기를 갖는 (메트)아크릴 화합물의 반-에스테르화에 의해 얻어지는 수지가 사용될 수 있다. 이와 같은 수지는 상기 안료 100중량부에 대하여 1 내지 30중량부의 함량으로 사용하는 것이 가능하다.
Furthermore, a photosensitive resin can be used as the resin. As the photosensitive resin, for example, a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group by reaction between the linear polymer and a (meth) acryl compound having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group or cinnamic acid Linear polymer containing a resin obtained by introducing a photocrosslinkable group such as a (meth) acryloyl group or a styryl group and an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer And a resin obtained by semi-esterification of a (meth) acryl compound having a hydroxy group such as hydroxyalkyl (meth) acrylate can be used. Such a resin can be used in an amount of 1 to 30 parts by weight based on 100 parts by weight of the pigment.
<유기용매><Organic Solvents>
상기 안료 분산 조성물에 사용되는 유기 용매는, 상기 안료 등을 분산시킬 수 있는 것이라면 특별히 한정되지 않으며, 탄소 원자수 3 내지 12의 에스테르, 케톤, 에테르, 알콜, 탄화수소 등으로부터 선택된 용매가 바람직하다. 상기 에스테르, 케톤, 에테르 또는 알콜은 고리 구조를 가질 수 있다. 에스테르, 케톤 및 에테르와 같은 작용기(-O-, -CO- 및 -COO-)를 2개 이상 갖는 화합물도 용매로서 사용할 수 있으며, 알콜계 히드록시기와 같은 다른 작용기도 동시에 존재할 수 있다. 2개 이상의 작용기를 갖는 용매의 경우, 많은 탄소원자가 상기 작용기를 갖는 화합물에 대하여 정의된 범위 내에 존재할 수 있다. The organic solvent used in the pigment dispersion composition is not particularly limited as long as it can disperse the pigment and the like, and a solvent selected from esters of 3 to 12 carbon atoms, ketones, ethers, alcohols, hydrocarbons and the like is preferable. The ester, ketone, ether or alcohol may have a ring structure. Compounds having two or more functional groups (-O-, -CO- and -COO-) such as esters, ketones and ethers can also be used as solvents and other functional groups such as alcoholic hydroxyl groups can be present at the same time. In the case of a solvent having two or more functional groups, many carbon atoms may be present within the range defined for the compound having the functional group.
상기 탄소 원자수 3 내지 12개를 갖는 에스테르로서는 에틸 포르메이트, 프로필 포르메이트, 펜틸 포르메이트, 메틸 아세테이트, 에틸 아세테이트 또는 펜틸 아세테이트를 예로 들 수 있다. 상기 탄소 원자수 3 내지 12개를 갖는 케톤으로서는 아세톤, 메틸 이소부틸 케톤, 메틸 에틸 케톤, 디에틸 케톤, 디이소부틸 케톤, 시클로펜타논, 시클로헥사논 및 메틸시클로헥사논을 예로 들 수 있다. 상기 탄소 원자수 3 내지 12개를 갖는 에테르로서는 프로필렌 글리콜 모노메틸 에테르 아세테이트, 디이소프로필에테르, 디메톡시메탄, 디메톡시에탄, 1,4-디옥산, 1,3-디옥산, 테트라히드로퓨란, 아니솔 및 펜에톨을 예로 들 수 있다. 또한 2종 이상의 작용기를 갖는 유기 용매로서는 2-에톡시헥실 아세테이트, 2-메톡시에탄올 및 2-부톡시에탄올을 예로 들 수 있다. 또한 상기 염소화 유기 용매와 조합하여 사용가능한 알콜은 선형, 분지형 또는 고리형이 있으며, 이들 중에서 포화 지방족 탄화수소가 바람직하다. 상기 알콜의 히드록시기는 1가, 2가 또는 3가가 가능하다. 알콜로서는 메탄올, 에탄올, 1-프로판올, 2-프로판올, 1-부탄올, 2-부탄올, t-부탄올, 1-펜탄올, 2-메틸-2부탄올 및 시클로헥산올을 예로 들 수 있다. 또한 불소화 알콜로서는 2-플루오로에탄올, 2,2,2-트리플루오로에탄올 또는 2,2,3,3-테트라플루오로-1-프로판올을 예로 들 수 있다. 또한 상기 탄화수소는 선형, 분지형 또는 고리형이 가능하며, 방향족 탄화수소 또는 지방족 탄화수소를 사용할 수 있다. 지방족 탄화수소는 포화 또는 불포화 모두 사용할 수 있다. 이와 같은 탄화수소로서는 시클로헥산, 헥산, 벤젠, 에틸벤젠, 톨루엔 및 크실렌을 예로 들 수 있다.Examples of the ester having 3 to 12 carbon atoms include ethyl formate, propyl formate, pentyl formate, methyl acetate, ethyl acetate or pentyl acetate. Examples of the ketone having 3 to 12 carbon atoms include acetone, methyl isobutyl ketone, methyl ethyl ketone, diethyl ketone, diisobutyl ketone, cyclopentanone, cyclohexanone and methylcyclohexanone. Examples of the ether having 3 to 12 carbon atoms include propylene glycol monomethyl ether acetate, diisopropyl ether, dimethoxymethane, dimethoxyethane, 1,4-dioxane, 1,3-dioxane, tetrahydrofuran, Anisole and phenitol are exemplified. Moreover, 2-ethoxyhexyl acetate, 2-methoxyethanol, and 2-butoxyethanol are mentioned as an organic solvent which has 2 or more types of functional groups. Alcohols usable in combination with the chlorinated organic solvents are also linear, branched or cyclic, of which saturated aliphatic hydrocarbons are preferred. The hydroxy group of the alcohol may be monovalent, divalent or trivalent. Examples of the alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, t-butanol, 1-pentanol, 2-methyl-2butanol, and cyclohexanol. Examples of the fluorinated alcohols include 2-fluoroethanol, 2,2,2-trifluoroethanol or 2,2,3,3-tetrafluoro-1-propanol. In addition, the hydrocarbon may be linear, branched or cyclic, and an aromatic hydrocarbon or an aliphatic hydrocarbon may be used. Aliphatic hydrocarbons can be used both saturated and unsaturated. Examples of such hydrocarbons include cyclohexane, hexane, benzene, ethylbenzene, toluene and xylene.
이와 같은 유기용매는 상기 안료 분산 조성물에서 상기 안료 입자들을 분산시킬 수 있는 함량으로 사용될 수 있으며, 특별한 제한은 없으나, 상기 안료 100중량부에 대하여 100 내지 1,000중량부의 함량으로 사용할 수 있다. 상기 유기 용매의 함량이 100중량부 미만이면 충분한 안료 분산을 얻을 수가 없고 점도가 높아져 작업성 등이 저하되며, 1,000중량부를 초과하는 경우 안료 농도가 지나치게 낮아 목적하는 색상을 충분히 발현하기 곤란하다는 문제가 있다.
Such an organic solvent may be used in an amount capable of dispersing the pigment particles in the pigment dispersion composition, and is not particularly limited, but may be used in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the pigment. If the content of the organic solvent is less than 100 parts by weight, sufficient pigment dispersion cannot be obtained, the viscosity is high, and workability is lowered. If the content is more than 1,000 parts by weight, the pigment concentration is too low, making it difficult to sufficiently express a desired color. have.
<기타 첨가제><Other additives>
또한, 통상의 보조제 또는 첨가제, 예컨대, 계면활성제, 충전제, 표준화제, 소포제, 항분진제, 증진제, 정전기방지제, 보존제, 건조 지연제, 습윤화제, 항산화제 등을 바람직하게는 안료 분산 조성물 총 중량을 기준으로 0.01 내지 10중량%, 특히 0.5 내지 5중량%의 양으로 추가로 포함할 수 있다.
In addition, conventional auxiliaries or additives, such as surfactants, fillers, standardizers, antifoams, anti-dust agents, enhancers, antistatic agents, preservatives, drying retardants, wetting agents, antioxidants and the like, preferably the total weight of the pigment dispersion composition It may further comprise in an amount of 0.01 to 10% by weight, in particular 0.5 to 5% by weight.
한편, 안료 분산 조성물을 제조하기 위해서는, 유기안료는, 1차 입자 지름이 100㎚ 이하이거나, 미립화 처리에 의해 1차 입자 지름을 100㎚ 이하로 한 유기안료를 이용하는 것이, 얻어지는 안료 조성물의 투명성이나 선명성의 향상이라는 관점으로부터 바람직하다. 안료의 미립화 처리법으로서는, 예를 들면, 식염(common salt)의 존재하에서 밀링을 실시하는 솔트 밀링법(salt-milling method) 등(예를 들면, 일본 특개 2001-220520 공보 및 일본 특개 2001-264528 공보)을 들 수 있지만, 이들에 한정되지 않는다.On the other hand, in order to manufacture a pigment dispersion composition, it is transparency of the pigment composition obtained by using an organic pigment whose primary particle diameter is 100 nm or less, or using an organic pigment which made the primary particle diameter 100 nm or less by an atomization process. It is preferable from a viewpoint of the improvement of sharpness. As a method for atomizing the pigment, for example, a salt milling method for milling in the presence of a common salt, etc. (for example, JP-A-2001-220520 and JP-A-2001-264528) ), But is not limited to these.
본 발명의 일실시예에 따른 안료 분산 조성물은 각각 상기 유기안료와 상기 안료 유도체를 종래 공지의 방법(예를 들면, 일본 특개 2001-271004 공보 및 특개 2004-91497 공보)에 의해 혼합하여 제조할 수 있다. 예를 들면, 상기 유기안료와 상기 안료 유도체의 분말끼리 혼합하는 방법, 물이나 용해력이 있는 유기용매에 분산시킨 상기 유기안료와 상기 안료 유도체와의 서스펜션끼리 혼합하는 방법, 유기안료의 제조 공정 중의 임의의 공정에 상기 안료 유도체를 첨가하는 방법 등을 들 수 있지만, 제조 방법은 특별히 한정되지 않는다. 상기 유기안료 제조 공정중의 임의의 공정으로서는, 예를 들면, 솔트 밀링(salt milling)을 들 수 있지만, 이것에 한정되지 않는다. 상기 안료 유도체를 첨가할 때 상태로서는, 분말, 페이스트, 서스펜션의 형태를 들 수 있지만, 이에 한정되지 않는다.The pigment dispersion composition according to the embodiment of the present invention may be prepared by mixing the organic pigment and the pigment derivative, respectively, by a conventionally known method (for example, Japanese Patent Application Laid-Open No. 2001-271004 and 2004-91497). have. For example, the method of mixing the powder of the said organic pigment and the said pigment derivative, the method of mixing the suspension of the said organic pigment and the said pigment derivative disperse | distributed to the water or the solvent which is soluble, and the process of manufacturing an organic pigment Although the method of adding the said pigment derivative to the process of etc. is mentioned, a manufacturing method is not specifically limited. As arbitrary processes in the said organic pigment manufacturing process, salt milling is mentioned, for example, It is not limited to this. When adding the said pigment derivative, although a form of powder, paste, and suspension is mentioned, it is not limited to this.
일례로서, 본 발명의 안료 분산 조성물은 상기 각 성분을 적정량 투입한 후 교반기로 혼합하면서 안료 파우더를 습윤(wetting)시키는 습윤 분산 안정화 공정을 통해 제조될 수 있으며, 이렇게 제조된 조성물 내 안료는 20 내지 150 nm의 평균입자 크기를 갖게 된다. 이때, 안료 분산의 효율성을 고려하여, 물리적 충돌력을 극대화시키기 위해 0.05 내지 2.0mm 지름의 비드(beads)를 사용할 수 있으며, 이러한 비드는 글라스, 스테인레스 스틸 또는 지르코늄 등의 재질인 것일 수 있다.As an example, the pigment dispersion composition of the present invention may be prepared through a wet dispersion stabilization process of wetting the pigment powder while mixing a suitable amount of the above components and mixing with a stirrer, the pigment in the composition thus prepared is 20 to It has an average particle size of 150 nm. At this time, in consideration of the efficiency of the pigment dispersion, to maximize the physical impact force bead (beads) of 0.05 to 2.0mm diameter (beads) can be used, such beads may be a material such as glass, stainless steel or zirconium.
또한, 상기 교반 공정 시 사용되는 분산기로는 비드밀, 롤밀, 아트라이터, 수퍼밀, 디졸버, 호모믹서, 샌드밀, 3-롤밀, 디스크밀, 페인트세이커 및 스칸덱스 등이 있으며, 일반적으로 비드밀이 가장 많이 사용된다.In addition, dispersers used in the stirring process include bead mills, roll mills, attritors, super mills, dissolvers, homomixers, sand mills, 3-roll mills, disc mills, paintsakers, and scandex. Bead mills are the most used.
한편, 본 발명의 안료 분산 조성물은 도료, 인쇄잉크 등으로서도 이용할 수 있으며, 감광성 피막 형성 재료와 혼합하여 광조사에 의해 화상형성이 가능한 안료 분산 컬러 레지스트 조성물로서도 적용될 수 있다. 본 발명의 안료 분산 조성물이 포함된 컬러 레지스트 조성물을 이용하여 공지의 방법 및 구조로 화소를 형성하게 되면 우수한 특성의 컬러필터를 얻게 된다. 컬러 레지스트 조성물은 본 발명의 안료 분산 조성물과, 감광성 피막 형성 재료를 혼합하여 고분산되어 얻어진다. 감광성 피막 형성 재료는 특별히 제한되지 않는다. 일반적으로 감광성 폴리아크릴레이트계 수지, 감광성 아크릴계 수지, 감광성 폴리아미드계 수지, 감광성 폴리이미드계 수지, 혹은 감광성 불포화 폴리에스테르계 수지 등의 감광성 수지 바니스, 또는 그러한 수지 반응 희석제로서 모노머 또는 올리고머가 더 첨가된 바니스, 광개시제(필요에 따라서 증감제와 함께), 용제 등의 성분으로 이루어진다. 본 발명의 안료 분산 조성물을 이용함으로써, 분산성, 분산 안정성, 투명성 및 선명성이 뛰어난 컬러필터 화소 형성용 컬러 레지스트 조성물 및 컬러필터를 얻을 수 있다.On the other hand, the pigment dispersion composition of the present invention can also be used as a coating material, printing ink and the like, and can be applied as a pigment dispersion color resist composition which can be mixed with a photosensitive film forming material and capable of image formation by light irradiation. When the pixel is formed by a known method and structure using the color resist composition containing the pigment dispersion composition of the present invention, a color filter having excellent characteristics is obtained. A color resist composition is obtained by mixing and dispersing the pigment dispersion composition of this invention and the photosensitive film formation material. The photosensitive film forming material is not particularly limited. Generally, photosensitive resin varnishes, such as photosensitive polyacrylate resin, photosensitive acrylic resin, photosensitive polyamide resin, photosensitive polyimide resin, or photosensitive unsaturated polyester resin, or monomer or oligomer are further added as such a resin reaction diluent. Consisting of varnishes, photoinitiators (with sensitizers as necessary), solvents and the like. By using the pigment dispersion composition of this invention, the color resist composition for color filter pixel formation and color filter excellent in dispersibility, dispersion stability, transparency, and clarity can be obtained.
상기 모노머 또는 올리고머로서는, 예를 들면, (메타)아크릴산에스테르, (메타)아크릴산, (메타)아크릴아미드, 초산비닐, 스티렌, (메타)아크릴로니트릴, (메타)아크릴레이트 올리고머 등을 들 수 있지만, 이들에 한정되지 않는다. 상기 광개시제로서는, 예를 들면, 아세트페논계, 벤조인계, 벤조페논계, 티옥산톤계, 트리아진계, 카르바졸계, 이미다졸계 등을 들 수 있지만, 이들에 한정되지 않는다. 상기 증감제로서는, 예를 들면, 아실포스핀옥사이드(acylphosphine oxide), 메틸페닐글리옥실레이트(methylphenylglyoxylate), 퀴논계(quinone-based), 안트라퀴논계(anthraquinone-based), 이소프탈로페논계(isophthalo phenone-based), 에스테르계(ester-based), 벤질계(benzil-based), 벤조페논계 (benzophenone-based) 등을 들 수 있지만, 이들에 한정되지 않는다. 용제로서는, 예를 들면, (폴리)알킬렌글리콜모노알킬에테르, (폴리)알킬렌글리콜모노알킬 에테르아세테이트, 에테르, 케톤, 유산알킬에스테르, 그 외의 에스테르, 방향족 탄화수소, 아미드 등을 들 수 있지만, 이들에 한정되지 않는다.
As said monomer or oligomer, (meth) acrylic acid ester, (meth) acrylic acid, (meth) acrylamide, vinyl acetate, styrene, (meth) acrylonitrile, (meth) acrylate oligomer, etc. are mentioned, for example. It is not limited to these. Examples of the photoinitiator include, but are not limited to, acetphenone series, benzoin series, benzophenone series, thioxanthone series, triazine series, carbazole series, imidazole series, and the like. Examples of the sensitizer include acylphosphine oxide, methylphenylglyoxylate, quinone-based, anthraquinone-based, isophthalo phenone-based, -based, ester-based, benzyl-based, benzophenone-based, and the like. Examples of the solvent include (poly) alkylene glycol monoalkyl ether, (poly) alkylene glycol monoalkyl ether acetate, ether, ketone, fatty acid alkyl ester, other esters, aromatic hydrocarbons and amides. But are not limited thereto.
이하 구체적인 실시예를 통해 안료 유도체의 구체예 및 합성 방법 등을 설명한다. 하기 설명은 본 발명의 일례이므로 나열된 구조나 설명으로 한정되지 않는다.
Hereinafter, specific examples and synthesis methods of the pigment derivative will be described through specific examples. The following description is an example of the present invention and is not limited to the listed structures and descriptions.
<실시예><Examples>
<안료 유도체의 제조>Preparation of Pigment Derivatives
(1) 안료 유도체 A의 합성(1) Synthesis of Pigment Derivative A
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, 1,5-Anthraquinone과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of solvent, the product obtained by reacting ethylenediamine with 1,5-Anthraquinone and Chlorosulfonic acid / Thionyl chloride was added dropwise to react. The product was obtained.
(2) 안료 유도체 B의 합성(2) Synthesis of Pigment Derivative B
Cyanuric chloride 3g과 5-Amino-2-benzimidazolinone 4.9g을 용매 100ml에서 반응시킨 후, Red 177과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 3 g of cyanuric chloride with 4.9 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Red 177 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(3) 안료유도체 C의 합성(3) Synthesis of Pigment Derivative C
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Orange 71과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, the final product was obtained by dropping and reacting the product obtained by reacting ethylenediamine with Orange 71 and Chlorosulfonic acid / Thionyl chloride. It was.
(4) 안료유도체 D의 합성(4) Synthesis of Pigment Derivative D
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Orange 73과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone were reacted in 100 ml of solvent, and then a product obtained by reacting ethylenediamine with orange 73 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(5) 안료유도체 E의 합성(5) Synthesis of Pigment Derivative E
Cyanuric chloride 2g과 5-Amino-2-benzimidazolinone 3.2g을 용매 100ml에서 반응시킨 후, Orange 73과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 2 g of cyanuric chloride with 3.2 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Orange 73 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(6) 안료유도체 F의 합성(6) Synthesis of Pigment Derivative F
Cyanuric chloride 2g과 5-Amino-2-benzimidazolinone 3.2g을 용매 100ml에서 반응시킨 후, Yellow 138과 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After 2 g of cyanuric chloride and 3.2 g of 5-Amino-2-benzimidazolinone were reacted in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Yellow 138 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(7) 안료유도체 G의 합성(7) Synthesis of Pigment Derivative G
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Red 122와 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride with 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Red 122 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(8) 안료유도체 H의 합성(8) Synthesis of Pigment Derivative H
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Red 254와 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Red 254 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(9) 안료유도체 I의 합성(9) Synthesis of Pigment Derivative I
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Red 255와 Chlorosulfonic acid/Thionyl chloride의 반응 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride with 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, a product obtained by reacting ethylenediamine with Red 255 and Chlorosulfonic acid / Thionyl chloride was added dropwise to give a final product. It was.
(10) 안료유도체 J의 합성(10) Synthesis of Pigment Derivative J
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Red 264와 Chlorosulfonic acid/Thionyl chloride와 반응하여 얻어진 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, ethylenediamine was added dropwise to a product obtained by reacting Red 264 with Chlorosulfonic acid / Thionyl chloride to give a final product. Obtained.
(11) 안료유도체 K의 합성(11) Synthesis of Pigment Derivative K
Cyanuric chloride 4g과 5-Amino-2-benzimidazolinone 6.5g을 용매 100ml에서 반응시킨 후, Red 272와 Chlorosulfonic acid/Thionyl chloride와 반응하여 얻어진 수득물에 에틸렌디아민을 반응시켜 얻어진 생성물을 적하하여 반응시킴으로써 최종 생성물을 수득하였다.
After reacting 4 g of cyanuric chloride and 6.5 g of 5-Amino-2-benzimidazolinone in 100 ml of a solvent, the product obtained by reacting Red 272 with Chlorosulfonic acid / Thionyl chloride was added dropwise to the product obtained by reacting ethylenediamine. Obtained.
<안료 분산 조성물의 제조><Production of Pigment Dispersion Composition>
실시예Example 1~11 1 to 11
하기 표 1과 같은 조성비로 안료, 안료 유도체, 분산제, 분산용 수지, 용매를 혼합하여 0.5mm 지르코니아 비드(beads) 100g을 넣고 페인트 쉐이커(paint shaker)에서 5시간 동안 분산 후 안료 분산 조성물을 얻었다.
The pigment, pigment derivative, dispersant, resin for dispersing, and solvent were mixed in the composition ratio as shown in Table 1 below, and 100 g of 0.5 mm zirconia beads were added and dispersed for 5 hours in a paint shaker to obtain a pigment dispersion composition.
레드 177CI Pigment
177 red
C.I.
안료
레드
254
CI
Pigment
Red
254
<실시예 및 비교예의 평가><Evaluation of Examples and Comparative Examples>
실시예 1~11의 안료 분산 조성물을 이용하여 형성된 패턴을 이용하여 각각의 조성물에 대한 평가를 실시하여 그 결과를 표 2에 나타내었다(하기에 평가 방법이나 기준으로 특별히 기재되지 않은 사항은 본 기술분야에서 통상적으로 사용되는 평가규격 또는 통상의 방법에 따른다).
Each composition was evaluated using the pattern formed using the pigment dispersion composition of Examples 1-11, and the result is shown in Table 2 (The matter which is not specifically described as an evaluation method or a criterion below is the present technology. According to the evaluation standards or conventional methods commonly used in the field).
(1) 콘트라스트(1) Contrast
상기 실시예 1~11의 안료 분산 조성물을 판두께 0.5mm의 60mmⅹ60mm 사이즈(size)의 유리 기판에 경화후의 x=0.650이(C광원)이 되도록 스핀 코팅하고, 90℃로 100초 건조한 뒤 초고압 수은 램프를 이용, 적산 광량 60mJ/㎠로 자외선 노광을 행했으며 도포 유리 기판을 230℃ 90분 가열한 후 각 건조 코팅 필름에 대하여 휘도계 CT-1(쓰보사카) 및 편광 플래이트를 사용하여 평행인 경우의 휘도와 직교인 경우의 휘도의 비율로써 콘트라스트 값을 계산하였다.
The pigment dispersion composition of Examples 1 to 11 was spin coated onto a glass substrate having a plate thickness of 0.5 mm to 60 mm x 60 mm size so that x = 0.650 after curing (C light source) was dried at 90 ° C. for 100 seconds, and then ultrahigh pressure mercury. Ultraviolet exposure was performed using a lamp with a cumulative amount of light 60 mJ / cm 2, and the coated glass substrate was heated at 230 ° C. for 90 minutes, and then parallel to each dry coating film using a luminance meter CT-1 (Tsubosaka) and a polarizing plate. The contrast value was calculated as the ratio of the luminance in the orthogonal to the luminance.
(2) 휘도(2) luminance
휘도 측정기로서 색 휘도 측정기 MCPD 3000(오츠카사)을 사용하여 x=0.650(C광원)에서의 RY를 측정하였다. Dispaly 상에서 RGB 각각 성분의 x, y 좌표는 한 점으로 표시되며 여기서 말한 x는 Chromaticity diagram에서 레드 성분의 크기를, RY는 레드 성분의 명도를 나타낸다(y는 그린 성분의 크기, GY는 그린 성분의 명도, z는 블루 성분의 크기, BY는 블루 성분의 명도를 나타낸다).The RY at x = 0.650 (C light source) was measured using a color luminance meter MCPD 3000 (Otsuka Co., Ltd.) as the luminance meter. In Dispaly, the x and y coordinates of each RGB component are represented by one point, where x is the size of the red component in the chromatic diagram and RY is the brightness of the red component (y is the size of the green component, GY is the size of the green component). Brightness, z is the magnitude of the blue component, BY is the brightness of the blue component).
(3) 점도 측정(3) viscosity measurement
상기 실시예 1~11의 안료 분산 조성물을 DV-II + VISCOMETER(브룩필드)를 이용하여 30rpm에서 초기 점도(25℃ 기준)를 측정하였으며 25℃의 저온 배양기에 보관 후 10, 20일 후 점도(25℃ 기준)를 측정하여 경시적 점도 변화를 확인하였다.
The pigment dispersion composition of Examples 1 to 11 was measured at an initial viscosity of 25 ° C. at 30 rpm using DV-II + VISCOMETER (Brookfield), and after 10, 20 days of storage in a 25 ° C. low temperature incubator, 25 ℃ reference) to measure the change in viscosity over time.
<표 2> 실시예의 평가 결과Table 2 Evaluation Results of Examples
상기 표 2에서와 같이, 본 발명의 실시예에 따른 안료 분산 조성물은 시간에 따른 점도변화가 미미하여 저장 안정성이 우수한 것을 알 수 있다. As shown in Table 2, it can be seen that the pigment dispersion composition according to the embodiment of the present invention has excellent storage stability due to a slight change in viscosity with time.
특히 본 발명의 일실시예에 따른 안료 분산 조성물은 상기의 평가 방법에 따라 평가를 수행하면 초기 대비 20일 이후의 점도 변화는 4cps 이하로 매우 우수하다.
In particular, when the pigment dispersion composition according to an embodiment of the present invention is evaluated according to the above evaluation method, the viscosity change after 20 days compared to the initial stage is very excellent as 4 cps or less.
상기의 설명은 본 발명의 이해를 돕기 위한 일례이므로, 본 발명의 기술적 사상의 범위내에서 가할 수 있는 구성의 변형, 치환, 수정, 생략 등은 특허청구범위에 의해 정해지는 본 발명의 권리범위에 포함된다.Since the above description is an example for better understanding of the present invention, modifications, substitutions, modifications, omissions, and the like which can be added within the scope of the technical idea of the present invention are within the scope of the present invention defined by the claims. Included.
Claims (12)
<화학식 2>
(상기 식에서, Q는 유기 색소 잔기이며, R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, R4는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알콕시기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴록시기, 치환 또는 무치환의 탄소수 1~60의 (헤테로)알킬아민기, 치환 또는 무치환의 탄소수 3~60의 (헤테로)아릴아민기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로)지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.)
Pigment derivative represented by the following formula (2).
(2)
(Wherein Q is an organic pigment residue, and R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms) , A substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, R 4 is each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted carbon atoms having 1 to 60 ( Hetero) alkyl group, substituted or unsubstituted (hetero) aryl group having 3 to 60 carbon atoms, substituted or unsubstituted (hetero) alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aryl having 3 to 60 carbon atoms A hydroxy group, a substituted or unsubstituted (hetero) alkylamine group having 1 to 60 carbon atoms, or a substituted or unsubstituted (hetero) arylamine group having 3 to 60 carbon atoms, X 2 is -NH-, -O- , or -SO 2 NH-, or a hetero atom, a substituted or unsubstituted C 1 -C 60 (hetero) aromatic hydrocarbon, a substituted or muchi Of carbon atoms it is configured is covalently bonded to at least one combination among the (hetero) aliphatic hydrocarbon of 1 ~ 60, X 3 is -NH-, -O-, or -SO 2 NH- or a hetero atom, the substituted or unsubstituted C 1 Covalently bonded to one or more combinations of (hetero) aromatic hydrocarbons of ˜20, substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 30 carbon atoms.)
<화학식 3>
(상기 식에서, Q는 유기 색소 잔기이며, R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, R5, R6, R7은 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X2는 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~60의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~60의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.
The pigment derivative according to claim 1, which is represented by the following Chemical Formula 3.
(3)
(Wherein Q is an organic pigment residue, and R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms) , Substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, R 5 , R 6 , R 7 are each independently halogen, amine group, cyano group, nitro group, substituted or unsubstituted carbon number 1 Or a (hetero) alkyl group of ˜20, a substituted or unsubstituted (hetero) aryl group of 3 to 30 carbon atoms, X 2 is —NH—, —O—, or —SO 2 NH— or a hetero element, substituted or Unsubstituted (hetero) aromatic hydrocarbons of 1 to 60 carbon atoms, substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 60 carbon atoms, covalently bonded to one or more combinations, each of X 3 and X 4 independently NH-, -O-, or -SO 2 NH- or a hetero atom, substituted or unsubstituted (hetero) room of 1 to 20 carbon atoms It is composed of covalently bonded one or more combinations of aromatic hydrocarbons, substituted or unsubstituted (hetero) aliphatic hydrocarbons having 1 to 30 carbon atoms.
<화학식 4>
(상기 식에서, Q는 유기 색소 잔기이며, R1, R2 및 R3는 각각 독립적으로 수소, 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, R5, R6, R7, R8, R9는 각각 독립적으로 할로겐, 아민기, 시아노기, 니트로기, 치환 또는 무치환의 탄소수 1~20의 (헤테로)알킬기, 치환 또는 무치환의 탄소수 3~30의 (헤테로)아릴기 중 선택되며, X3, X4는 각각 독립적으로 -NH-, -O-, 또는 -SO2NH- 이거나 헤테로 원소, 치환 또는 무치환의 탄소수 1~20의 (헤테로)방향족 탄화수소, 치환 또는 무치환의 탄소수 1~30의 (헤테로) 지방족 탄화수소 중에서 하나 이상의 조합으로 공유결합 되어 구성된다.)
The pigment derivative according to claim 1, which is represented by the following formula (4).
≪ Formula 4 >
(Wherein Q is an organic pigment residue, and R 1 , R 2 and R 3 are each independently hydrogen, halogen, amine group, cyano group, nitro group, substituted or unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms) , A substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, R 5 , R 6 , R 7 , R 8 , R 9 are each independently halogen, amine group, cyano group, nitro group, substituted Or an unsubstituted (hetero) alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted (hetero) aryl group having 3 to 30 carbon atoms, and X 3 and X 4 are each independently -NH-, -O-, Or -SO 2 NH- or a hetero atom, substituted or unsubstituted (hetero) aromatic hydrocarbon of 1 to 20 carbon atoms, covalently bonded in one or more combinations of substituted or unsubstituted (hetero) aliphatic hydrocarbons of 1 to 30 carbon atoms do.)
The pigment derivative according to claim 1, wherein the organic pigment residue is selected from an anthraquinone series, dianthraquinone series, diketopyrrolopyrrole series, and quinophthalone series.
The pigment dispersion composition containing the pigment derivative and organic pigment of any one of Claims 1-5.
The pigment dispersion composition according to claim 6, wherein the series of organic pigment residues of the pigment derivative and the series of organic pigments are the same.
The pigment dispersion composition according to claim 6, wherein the pigment derivative is contained in an amount of 0.1 to 30 parts by weight based on 100 parts by weight of the organic pigment.
The pigment dispersion composition of claim 6, further comprising an organic solvent, wherein the organic solvent is included in an amount of 100 to 1,000 parts by weight based on 100 parts by weight of the organic pigment.
According to claim 6, using the DV-II + VISCOMETER (Brookfield) to measure the initial viscosity (at 25 ℃) at 30rpm, the viscosity (based on 25 ℃) 20 days after storage in a low temperature incubator at 25 ℃ When the viscosity change after 20 days compared to the initial stage, the pigment dispersion composition, characterized in that 4cps or less.
The pigment resist composition of Claim 6 and the photosensitive film forming material are included, The color resist composition characterized by the above-mentioned.
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| JP6630929B2 (en) * | 2015-07-31 | 2020-01-15 | 山陽色素株式会社 | Pigment derivative, pigment dispersion and colored photosensitive composition |
| JP7064090B2 (en) * | 2020-05-21 | 2022-05-10 | 東洋インキＳｃホールディングス株式会社 | Pigment compositions for color filters, coloring compositions, and color filters |
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