WO2016170828A1 - カラーフィルタ用緑色顔料組成物およびカラーフィルタ - Google Patents
カラーフィルタ用緑色顔料組成物およびカラーフィルタ Download PDFInfo
- Publication number
- WO2016170828A1 WO2016170828A1 PCT/JP2016/054400 JP2016054400W WO2016170828A1 WO 2016170828 A1 WO2016170828 A1 WO 2016170828A1 JP 2016054400 W JP2016054400 W JP 2016054400W WO 2016170828 A1 WO2016170828 A1 WO 2016170828A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- pigment
- green
- color filter
- composition
- phthalocyanine pigment
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 108
- 239000001056 green pigment Substances 0.000 title claims abstract description 50
- 239000000049 pigment Substances 0.000 claims abstract description 187
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 claims abstract description 154
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 50
- 125000005543 phthalimide group Chemical group 0.000 claims abstract description 50
- 125000000524 functional group Chemical group 0.000 claims abstract description 9
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 60
- 239000011701 zinc Substances 0.000 claims description 58
- 229910052725 zinc Inorganic materials 0.000 claims description 57
- 150000004820 halides Chemical class 0.000 claims description 54
- 238000004519 manufacturing process Methods 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
- 238000003801 milling Methods 0.000 claims description 12
- 239000001052 yellow pigment Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000001246 bromo group Chemical group Br* 0.000 claims description 8
- 150000003751 zinc Chemical class 0.000 abstract description 75
- -1 chlorinated zinc phthalocyanine derivative Chemical class 0.000 abstract description 17
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- 229910052794 bromium Inorganic materials 0.000 description 14
- 238000011156 evaluation Methods 0.000 description 14
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- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical class [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 3
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- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical class N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 3
- 230000019612 pigmentation Effects 0.000 description 3
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- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
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- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- XHPWRTXYJFNZAW-UHFFFAOYSA-N [[4-[2-(4-diazonioimino-2-sulfocyclohexa-2,5-dien-1-ylidene)ethylidene]-3-sulfocyclohexa-2,5-dien-1-ylidene]hydrazinylidene]azanide Chemical compound OS(=O)(=O)C1=CC(N=[N+]=[N-])=CC=C1C=CC1=CC=C(N=[N+]=[N-])C=C1S(O)(=O)=O XHPWRTXYJFNZAW-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000005054 agglomeration Methods 0.000 description 1
- 239000005456 alcohol based solvent Substances 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- APUPEJJSWDHEBO-UHFFFAOYSA-P ammonium molybdate Chemical compound [NH4+].[NH4+].[O-][Mo]([O-])(=O)=O APUPEJJSWDHEBO-UHFFFAOYSA-P 0.000 description 1
- 235000018660 ammonium molybdate Nutrition 0.000 description 1
- 239000011609 ammonium molybdate Substances 0.000 description 1
- 229940010552 ammonium molybdate Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 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
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QHIWVLPBUQWDMQ-UHFFFAOYSA-N butyl prop-2-enoate;methyl 2-methylprop-2-enoate;prop-2-enoic acid Chemical compound OC(=O)C=C.COC(=O)C(C)=C.CCCCOC(=O)C=C QHIWVLPBUQWDMQ-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 229940112021 centrally acting muscle relaxants carbamic acid ester Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000007822 coupling agent Substances 0.000 description 1
- 238000001723 curing Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- TXKMVPPZCYKFAC-UHFFFAOYSA-N disulfur monoxide Inorganic materials O=S=S TXKMVPPZCYKFAC-UHFFFAOYSA-N 0.000 description 1
- 238000009837 dry grinding Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 239000004210 ether based solvent Substances 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000000040 green colorant Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- ZKVLEFBKBNUQHK-UHFFFAOYSA-N helium;molecular nitrogen;molecular oxygen Chemical compound [He].N#N.O=O ZKVLEFBKBNUQHK-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000000016 photochemical curing Methods 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 230000000485 pigmenting effect Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920005575 poly(amic acid) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical compound S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- PUGUQINMNYINPK-UHFFFAOYSA-N tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(C(=O)CCl)CC1 PUGUQINMNYINPK-UHFFFAOYSA-N 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/10—Obtaining compounds having halogen atoms directly bound to the phthalocyanine skeleton
-
- 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
- C09B47/00—Porphines; Azaporphines
- C09B47/04—Phthalocyanines abbreviation: Pc
- C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
- C09B47/12—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton
- C09B47/16—Obtaining compounds having alkyl radicals, or alkyl radicals substituted by hetero atoms, bound to the phthalocyanine skeleton having alkyl radicals substituted by nitrogen atoms
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- 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
- 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
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
-
- 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
Definitions
- the present invention relates to a green pigment composition for a color filter and a color filter.
- a color filter used in a liquid crystal display arranges a plurality of colors regularly on a transparent glass substrate, and transmits only light in a necessary wavelength region from white light of a backlight that passes through the color filter. It is a member that realizes color display.
- the colors used there generally include the three primary colors of red, green, and blue, and improvements have been made with respect to color materials, resins, additives, and the like used to adjust the transmission spectrum. Among them, green colorants for color filters are required to have high brightness and an expanded color reproduction range from the viewpoint of improving the image quality of the display.
- a color filter coloring composition comprising a pigment and a phthalocyanine pigment having a substituent has been proposed as a color filter coloring composition excellent in contrast ratio, dispersion stability, and chemical resistance of the color filter (cited).
- Reference 2 a color filter coloring composition excellent in contrast ratio, dispersion stability, and chemical resistance of the color filter (cited).
- the present invention relates to a green pigment composition
- a green pigment composition comprising a halogenated zinc phthalocyanine pigment and a brominated chlorinated zinc phthalocyanine derivative having a phthalimide skeleton bonded with an alkylene group, capable of greatly improving contrast without reducing luminance and coloring power. And providing a color filter comprising the green pigment composition.
- the color filter pigment composition according to the present invention contains 0.1 to 10 parts of the pigment derivative represented by the general formula (1) per 100 parts of the halogenated zinc phthalocyanine pigment in terms of mass. Green pigment composition.
- Z1 to Z16 each independently represents a functional group having a phthalimide skeleton bonded by a bromine atom, a chlorine atom, a hydrogen atom or an alkylene group having 1 to 3 carbon atoms.
- the average number of bromine atoms in the molecule is 8 to 12
- the average number of chlorine atoms is 2 to 5
- the functional group having a phthalimide skeleton bonded by an alkylene group having 1 to 3 carbon atoms has an average number of substituents of 0.1. ⁇ 3, the rest are hydrogen atoms.
- the halogenated zinc phthalocyanine pigment has an average of 10 to 14 halogen atoms in one molecule, of which the average number of bromine atoms is 8 to 12, and the average number of chlorine atoms is 2 to 5 Green pigment composition for filters.
- a green pigment composition for a color filter further comprising a yellow pigment.
- Another object of the present invention is to provide a method for producing the above-described color filter pigment composition by solvent salt milling.
- the present invention relates to a halogenated zinc phthalocyanine pigment and a halogen having an average number of halogen atoms of 10 to 14 in one molecule, of which an average number of bromine atoms is 8 to 12 and an average number of chlorine atoms is 2 to 5.
- a pigment composition composed of a pigment derivative having a functional group composed of a phthalimide skeleton bonded to a zinc fluoride phthalocyanine pigment with an alkylene group having 1 to 3 carbon atoms, brightness and coloring power are not significantly reduced.
- a color filter capable of improving contrast can be provided.
- a pigment composition comprising a halogenated zinc phthalocyanine pigment and a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton, it is possible to significantly improve contrast without deteriorating luminance and coloring power. Turned out to be able to create.
- the halogenated zinc phthalocyanine pigment is a compound in which zinc metal is arranged at the center, and a phthalocyanine ring which may be substituted by a substituent other than halogen is substituted with at least one halogen atom selected from chlorine, bromine, fluorine or iodine The total number of each substituent is 16 at maximum.
- the portion not substituted with halogen and a substituent other than halogen is hydrogen.
- the halogenated zinc phthalocyanine pigment is a halogenated zinc phthalocyanine having an average primary particle size of 0.01 to 0.30 ⁇ m.
- brightness which is a desired optical characteristic
- It is a common pigment particle size to achieve a contrast ratio.
- the average primary particle diameter in the present invention refers to the halogenation constituting an aggregate on a two-dimensional image obtained by photographing particles in the field of view with a transmission electron microscope JEM-2010 (manufactured by JEOL Ltd.). For 50 primary particles of the zinc phthalocyanine pigment, the longer diameter (major diameter) is obtained and averaged. At this time, the sample zinc halide phthalocyanine pigment is ultrasonically dispersed in a solvent and then photographed with a microscope. A scanning electron microscope may be used instead of the transmission electron microscope.
- the green pigment composition for color filters of the present invention uses a halogenated zinc phthalocyanine pigment derivative whose hue is adjusted by adjusting the halogenation number and introducing a phthalimide skeleton bonded with a bulky alkylene group.
- a conventional green pigment having a higher halogenation number is more specific to a bluish hue than a yellowish hue.
- a zinc halide phthalocyanine pigment composition that is more bluish than the zinc halide phthalocyanine pigment composition of the present invention is not suitable as a color filter pigment composition because it cannot form a green pixel when mixed with a yellow pigment composition.
- the transmittance was low and the luminance of the display obtained was lowered. The luminance can be compensated for by increasing the amount of light from the backlight, but an improvement is required because of the new problem of increased power consumption.
- the zinc halide phthalocyanine pigment composition used in the present invention can be produced from a halogenated zinc phthalocyanine pigment.
- This halogenated zinc phthalocyanine pigment can be produced by a known production method such as a chlorosulfonic acid method, a halogenated phthalonitrile method, or a melting method.
- Examples of the chlorosulfonic acid method include a method in which zinc phthalocyanine is dissolved in a sulfur oxide solvent such as chlorosulfonic acid, and chlorine gas and bromine are added thereto to halogenate. The reaction at this time is carried out at a temperature of 20 to 120 ° C. for 3 to 20 hours.
- halogenated phthalonitrile method examples include, for example, phthalic acid or phthalodinitrile in which some or all of the hydrogen atoms of the aromatic ring are substituted with halogen atoms such as chlorine and fluorine in addition to bromine, and zinc metal or metal salt And a method of synthesizing a corresponding zinc halide phthalocyanine pigment using as a starting material.
- a catalyst such as ammonium molybdate may be used as necessary.
- the reaction at this time is carried out at a temperature of 100 to 300 ° C. for 7 to 35 hours.
- Melting methods include aluminum halides such as aluminum chloride and aluminum bromide, titanium halides such as titanium tetrachloride, alkali metal halides or alkaline earth metal halides such as sodium chloride and sodium bromide [ Hereinafter referred to as alkali (earth) metal halide], thionyl chloride, etc., in a melt of about 10 to 170 ° C. composed of one or a mixture of two or more kinds of compounds that serve as solvents during various halogenations.
- alkali (earth) metal halide alkali (earth) metal halide
- thionyl chloride etc.
- a suitable aluminum halide is aluminum chloride.
- the addition amount of the aluminum halide is usually 3 times mol or more, preferably 10 to 20 times mol with respect to zinc phthalocyanine.
- Aluminum halide may be used alone, but when an alkali (earth) metal halide is used in combination with aluminum halide, the melting temperature can be further lowered, which is advantageous in operation.
- a preferred alkali (earth) metal halide is sodium chloride.
- the amount of alkali (earth) metal halide to be added is preferably 5 to 15 parts by mass of alkali (earth) metal halide with respect to 10 parts by mass of aluminum halide within a range in which a molten salt is formed.
- examples of the halogenating agent include chlorine gas, sulfuryl chloride, bromine and the like.
- the halogenation temperature is preferably 10 to 170 ° C, more preferably 30 to 150 ° C. Furthermore, pressurization is possible to increase the reaction rate.
- the reaction time is 5 to 100 hours, preferably 30 to 45 hours.
- the melting method using two or more of the above-mentioned compounds in combination is possible by adjusting the ratio of chloride, bromide and iodide in the molten salt, or by changing the introduction amount and reaction time of chlorine gas, bromine and iodine.
- the content ratio of the halogenated zinc phthalocyanine pigment having a specific halogen atom composition can be arbitrarily controlled, which is preferable.
- the metal phthalocyanine that is a suitable raw material in the present invention is zinc phthalocyanine.
- the melting method is suitable because the raw material during the reaction is less decomposed, the yield from the raw material is better, and the reaction can be performed in an inexpensive apparatus without using a strong acid.
- a zinc halide phthalocyanine pigment having a halogen atom composition different from that of an existing zinc halide phthalocyanine pigment can be obtained by optimizing the raw material charging method, catalyst type and amount, reaction temperature and reaction time.
- the produced zinc halide phthalocyanine pigment is precipitated.
- the halogenated zinc phthalocyanine pigment it may be used as it is, but then filtered, washed with water or sodium hydrogen sulfate aqueous solution, sodium hydrogen carbonate aqueous solution, sodium hydroxide aqueous solution, if necessary acetone, toluene, methyl alcohol, It is preferably used after washing with an organic solvent such as ethyl alcohol or dimethylformamide and after-treatment such as drying.
- the pigment derivative of the present invention is a pigment derivative represented by the general formula (1)
- Z1 to Z16 each independently represents a functional group having a phthalimide skeleton bonded by a bromine atom, a chlorine atom, a hydrogen atom or an alkylene group having 1 to 3 carbon atoms.
- the average number of bromine atoms in the molecule is 8 to 12
- the average number of chlorine atoms is 2 to 5
- the functional group having a phthalimide skeleton bonded by an alkylene group having 1 to 3 carbon atoms has an average number of substituents of 0.1. ⁇ 3, the rest are hydrogen atoms.
- a zinc halide phthalocyanine pigment derivative having a phthalimide skeleton bonded by an alkylene group represented by the general formula (1) is obtained by dissolving a phthalocyanine compound in sulfuric acid as disclosed in JP-A-2-255863, It is obtained by adding paraformaldehyde and reacting at 80 ° C., and has a phthalimide skeleton bonded to a phthalocyanine skeleton by a bromine atom, chlorine atom, hydrogen atom or alkylene group, and at least a phthalimide skeleton bonded by an alkylene group
- the average number of substituents of the functional group is 0.1 to 3.
- a bromine atom and a chlorine atom are contained in a specific ratio.
- a halogenated zinc phthalocyanine pigment having an average number of bromine atoms of 8 to 12 and an average number of chlorine atoms of 2 to 5 in one molecule. More preferably, the number of halogen atoms in one molecule is 11 to 13 on average, among them, the average number of bromine atoms is 8 to 11 and the number of chlorine atoms is 2 to 3 on average in order to develop high color reproduction.
- a linking group having 1 to 3 carbon atoms is preferable, and among them, a compound having a methylene group having 1 carbon atom as a linking group is more preferable in that pigment aggregation can be efficiently suppressed.
- the number of substituents of the phthalimide group having an alkylene group can be substituted by 1 to 6 (since the halogen number is at least 10).
- the number of carbon atoms is 4 or more, it is considered that the alkylene skeleton becomes a long chain, the arrangement of the phthalimide groups cannot be adjusted, and the effect as a derivative cannot be obtained.
- the number of halogen atoms and the average composition of the zinc halide phthalocyanine pigment composition can be determined by fluorescent X-ray analysis.
- X-ray fluorescence analysis was performed using ZSX100E (manufactured by Rigaku Corporation) as the analyzer, and the content ratio of each element was determined from the K ⁇ -ray intensities of zinc, bromine and chlorine, and bromine and chlorine when zinc was 1. It can obtain
- a sample for infrared absorption spectrum is prepared by mixing a halogenated zinc phthalocyanine derivative with KBr and pressurizing it.
- the infrared absorption spectrum was measured with FT / IR-6100 (manufactured by JASCO Corporation), the absorption peak height of 1770 cm ⁇ 1 or 1720 cm ⁇ 1, which is the characteristic absorption of the phthalimide alkyl group, and the characteristics of phthalocyanine
- the calculation is performed by calculating the average number of substituents from the ratio of the peak height of absorption at 1390 cm ⁇ 1, which is absorption.
- a halogenated zinc phthalocyanine derivative having a phthalimide skeleton bonded with an alkylene group can be directly subjected to mass spectrometry to quantitatively analyze 1 to 4 substituents, and averaged to calculate the average number of substituents.
- the above-mentioned green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment can be used in a grinder such as an attritor, ball mill, vibration mill, vibration ball mill or the like.
- a grinder such as an attritor, ball mill, vibration mill, vibration ball mill or the like.
- the ratio of the halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment is not particularly limited, but the phthalimide skeleton bonded with an alkylene group per 100 parts of the halogenated zinc phthalocyanine pigment in terms of mass is not limited. It is preferable that the halogenated zinc phthalocyanine pigment derivative is contained in an amount of 0.1 to 10 parts because high contrast can be obtained while maintaining the luminance and coloring power when the pigment composition is used as a color filter.
- the pigmentation method of the green pigment composition comprising a halogenated zinc phthalocyanine pigment and a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded by an alkylene group.
- a halogenated zinc phthalocyanine pigment before pigmentation A green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group can be dispersed in a dispersion medium and pigmented at the same time, but a zinc halide phthalocyanine in a large amount of an organic solvent Compared with a solvent treatment in which a green pigment composition comprising a zinc halide phthalocyanine pigment derivative having a phthalimide skeleton bonded with a pigment and an alkylene group is heated and stirred, pigment growth can be easily suppressed and pigment particles having a large specific surface area can be obtained. Solvent solution It is preferable to employ a Tomiringu process.
- This solvent salt milling is a green pigment composition
- a zinc halide phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a non-pigmented zinc halide phthalocyanine pigment that has been ground immediately after synthesis or thereafter.
- a kneading machine at this time for example, a kneader, a mix muller, a trimix, a twin screw extruder or the like can be used.
- a water-soluble inorganic salt can be preferably used.
- an inorganic salt such as sodium chloride, potassium chloride, sodium sulfate is preferably used. It is more preferable to use an inorganic salt having an average particle size of 0.5 to 50 ⁇ m. Such an inorganic salt can be easily obtained by pulverizing a normal inorganic salt.
- a green pigment composition comprising a halogenated zinc phthalocyanine pigment having an average primary particle diameter of 0.01 to 0.10 ⁇ m and a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded by an alkylene group is used as a color filter. It is preferable to use for an application.
- an organic solvent capable of suppressing crystal growth it is preferable to use an organic solvent capable of suppressing crystal growth, and as such an organic solvent, a water-soluble organic solvent can be suitably used.
- a water-soluble organic solvent can be suitably used.
- a green pigment composition composed of a halogenated zinc phthalocyanine pigment and a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group is produced by solvent salt milling
- the zinc halide phthalocyanine pigment and the phthalocyanine are combined with an alkylene group.
- the zinc halide phthalocyanine pigment derivative having a phthalimide skeleton having a phthalimide skeleton bonded to the zinc halide phthalocyanine pigment and an alkylene group may be combined by solvent salt milling. Can be mixed in the apparatus at the same time for solvent salt milling.
- phthalocyanine derivative having a phthalimide skeleton bonded with an alkylene group any known and commonly used phthalocyanine derivatives can be used, but phthalocyanine pigment derivatives of the following general formula (1) or (2) are preferred.
- the phthalocyanine derivative is preferably a halogenated zinc phthalocyanine pigment or a phthalocyanine derivative corresponding to zinc phthalocyanine which is a raw material thereof.
- a halogenated copper phthalocyanine derivative or a copper phthalocyanine derivative is used. You can also
- P represents an unsubstituted or halogenated phthalocyanine ring-free residue having no central metal or having a central metal;
- Y represents a primary to tertiary amino group, a carboxylic acid group, Represents a sulfonic acid group or a salt thereof with a base or a metal,
- A represents a divalent linking group,
- Z represents a residue obtained by removing at least one hydrogen on the nitrogen atom of the primary or secondary amino group, or nitrogen. Represents a residue obtained by removing at least one of hydrogen atoms on the nitrogen atom of the heterocyclic ring, and n represents 1 to 4)
- the central metal is Zn, and examples of the primary or secondary amino group include a monomethylamino group, a dimethylamino group, and a diethylamino group.
- examples of the base or metal that forms a salt with the carboxylic acid group or sulfonic acid group include ammonia, organic bases such as dimethylamine, diethylamine, and triethylamine, and metals such as potassium, sodium, calcium, strontium, and aluminum.
- Examples of the divalent linking group of A include a divalent linking group such as an alkylene group having 1 to 3 carbon atoms, —CO 2 —, —SO 2 —, —SO 2 NH (CH 2 ) m—, etc. Groups.
- Examples of Z include a phthalimide group, a monoalkylamino group, and a dialkylamino group.
- the phthalocyanine derivative that can be included in the zinc halide phthalocyanine pigment during preparation of the halogenated zinc phthalocyanine pigment and / or during solvent salt milling is usually 0.01 to 0.3 parts by mass per 1 part by mass of the halogenated zinc phthalocyanine pigment. .
- the total amount of the crude pigment and the phthalocyanine derivative is regarded as the amount of the crude pigment used, and the amount of inorganic salt used is Select from the above-mentioned range.
- the temperature is preferably from 30 to 150 ° C., more preferably from 80 to 100 ° C. in order to suppress crystal growth during solvent salt milling and achieve a small particle size suitable for color filter applications.
- the solvent salt milling time is preferably 5 to 20 hours, more preferably 8 to 18 hours.
- a zinc halide phthalocyanine pigment composition having an average primary particle diameter of 0.01 to 0.10 ⁇ m, a mixture containing an inorganic salt and an organic solvent as main components can be obtained. From this mixture, the organic solvent and the inorganic salt are mixed.
- the powder of the halogenated zinc phthalocyanine pigment composition can be obtained by removing, if necessary, washing, filtering, drying, pulverizing, etc. the solid material mainly composed of the halogenated zinc phthalocyanine pigment composition.
- washing either water washing or hot water washing can be adopted.
- the number of washings can be repeated in the range of 1 to 5 times.
- the organic solvent and the inorganic salt can be easily removed by washing with water. If necessary, acid cleaning, alkali cleaning, and organic solvent cleaning may be performed so as not to change the crystal state.
- drying after filtration and washing described above examples include batch or continuous drying in which the pigment is dehydrated and / or desolventized by heating at 80 to 120 ° C. with a heating source installed in a dryer.
- the dryer generally include a box dryer, a band dryer, and a spray dryer.
- spray dry drying is preferable because it is easily dispersed during paste preparation.
- the pulverization after drying is not an operation for increasing the specific surface area or reducing the average particle size of the primary particles.
- the pigment is used as in the case of drying using a box dryer or a band dryer.
- a dry powder containing as a main component a green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention is obtained.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention has a primary particle agglomeration force as compared with a conventional copper halide phthalocyanine pigment. Is weak and easy to understand. From the electron micrograph, it is possible to observe individual pigment primary particles constituting the aggregate, which cannot be observed with a conventional pigment.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment according to the present invention can be used for any known and commonly used applications. Since the diameter is 0.01 to 0.10 ⁇ m, the aggregation of the pigment is relatively weak and the dispersibility in the synthetic resin to be colored becomes better.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention is used for a color filter when used in a color filter green pixel portion. It is easy to disperse the pigment in the photosensitive composition, the photocuring sensitivity to the 365 nm emission line often used when curing the photosensitive composition for color filters does not decrease, and film edge and pattern flow occur during development. It is preferable because it becomes difficult. A color filter green pixel portion having both high luminance and color reproducibility required in recent years can be more easily obtained.
- the primary particles of the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment according to the present invention have a longitudinal and lateral aspect ratio of 1 to 3, Viscosity characteristics are improved and fluidity is higher in the application field.
- the aspect ratio first, as in the case of obtaining the average particle diameter of the primary particles, the particles in the field of view are photographed with a transmission electron microscope or a scanning electron microscope. Then, an average value of the longer diameter (major axis) and the shorter diameter (minor axis) is obtained for 50 primary particles constituting the aggregate on the two-dimensional image, and the average value is calculated using these values. .
- the color of the present invention A filter can be obtained.
- a green pigment composition comprising a zinc halide phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention is a green pixel portion of a color filter. If necessary, a yellow pigment can be used in combination for toning.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment according to the present invention is 380 like the conventional zinc halide phthalocyanine pigment.
- the wavelength (Tmax) at which the transmittance of the spectral transmission spectrum at ⁇ 780 nm is maximum is 500 to 520 nm, and the half width of the transmission curve is 110 nm or less, which is very sharp. (This wavelength is not affected by the photosensitive resin as described later.)
- the spectral transmission spectrum in the color filter evaluation is obtained according to the first class spectrophotometer of Japanese Industrial Standard JIS Z 8722 (color measurement method-reflection and transmission object color).
- the resin film containing the pigment composition formed into a predetermined dry film thickness is obtained by plotting each transmittance value at each wavelength by scanning and irradiating light in a predetermined wavelength region.
- the transmittance as a color filter can be determined with higher accuracy by correcting (baseline correction or the like), for example, with a spectral transmission spectrum similarly determined for a film having the same dry film thickness only with a resin.
- the color filter containing a green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment according to the present invention in a green pixel portion is a light source such as white light, F10, etc. Can transmit the light in the green region of the light source well, and the spectral transmission spectrum of the zinc halide phthalocyanine pigment composition is sharp, so that the green color purity and coloring power are maximized. be able to.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention can be used as it is for the production of the green pixel portion of a color filter.
- a green halogenated metal phthalocyanine pigment such as a publicly known and commonly used green halogenated copper phthalocyanine or other green halogenated different metal phthalocyanine pigment may be used in combination.
- a yellow pigment may be used for toning to develop characteristics.
- yellow pigments that can be used here include C.I. I.
- yellow organic pigments such as CI Pigment Yellow 83, 110, 129, 138, 139, 150, 180, and 185.
- the combined proportion of the halogenated zinc phthalocyanine pigment composition of the present invention and the yellow pigment is 10 to 200 parts by mass of the yellow pigment per 100 parts by mass of the zinc halide phthalocyanine pigment composition.
- a green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention is used, even when a yellow pigment is used in combination for color matching, Compared with the conventional case where two or more kinds of pigments of different colors are mixed for toning, the color filter green pixel portion is less turbid, excellent in color purity and coloring power, and bright.
- the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment of the present invention is used for forming a pattern of a green pixel portion of a color filter by a known method. I can do it.
- a photosensitive composition for a color filter green pixel portion containing the zinc halide phthalocyanine pigment composition of the present invention and a photosensitive resin as essential components can be obtained.
- a method for producing a color filter for example, after dispersing this halogenated zinc phthalocyanine pigment composition in a dispersion medium made of a photosensitive resin, glass or the like by spin coating method, roll coating method, slit coating method, ink jet method or the like.
- a method called photolithography in which a green pattern is obtained by applying an ultraviolet ray through a photomask to the coated film and then washing the unexposed portion with a solvent or the like. Is mentioned.
- a color filter may be manufactured by forming a pattern of the green pixel portion by an electrodeposition method, a transfer method, a micellar electrolysis method, or a PVED (Photovoltaic Electrodeposition) method.
- the pattern of a red pixel part and the pattern of a blue pixel part can also be formed by the same method using a well-known pigment.
- a photosensitive composition for a color filter green pixel portion for example, a green pigment composition comprising a zinc halide phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a zinc halide phthalocyanine pigment of the present invention;
- a photosensitive resin, a photopolymerization initiator, and an organic solvent that dissolves the resin are mixed as essential components.
- a general method is to prepare a dispersion using a halogenated zinc phthalocyanine pigment composition, an organic solvent and, if necessary, a dispersant, and then add a photosensitive resin or the like to the dispersion. is there.
- a green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with a halogenated zinc phthalocyanine pigment and an alkylene group, and a yellow pigment can be used as necessary.
- Dispersants used as necessary include, for example, Big Chemie's DISPERBYK (registered trademark) 130, 161, 162, 163, 170, LPN-6919, LPN-21116, and Fuka 46 of Efka. Fka 47 and the like.
- a doctor bar rigging agent, a coupling agent, a cationic surfactant, and the like can be used together.
- organic solvent examples include aromatic solvents such as toluene, xylene, and methoxybenzene, acetate solvents such as ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and ethoxyethyl propionate.
- Propionate solvents such as alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, and fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, ⁇ -butyrolactam, N-methyl-2-pyrrolidone, a Phosphorus, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as ⁇ - butyrolactone, there are carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate.
- ether solvents such as butyl cellosolve
- propylene glycol monomethyl ether diethylene glycol ethyl ether
- the dispersion can be obtained by stirring and dispersing so as to be uniform.
- 3 to 20 parts by weight of the photosensitive resin per 1 part by weight of the zinc halide phthalocyanine pigment composition, 0.05 to 3 parts by weight of a photopolymerization initiator per 1 part by weight of the photosensitive resin are added to the dispersion.
- an organic solvent is further added, and the mixture is stirred and dispersed so as to be uniform, whereby a photosensitive composition for a color filter green pixel portion can be obtained.
- photosensitive resins examples include urethane resins, acrylic resins, polyamic acid resins, polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, and the like, Bifunctional monomers such as 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, Trimethylol propaton triacrylate, pentaerythritol triacrylate, tris (2-hydroxyethyl) isocyanate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate Photopolymerizable monomers such as polyfunctional monomers may be mentioned such as equal.
- photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4 ′ -Azidobenzal) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid, and the like.
- the thus-prepared photosensitive composition for green color pixel portion of the color filter becomes a color filter by performing pattern exposure with ultraviolet rays through a photomask and then washing the unexposed portion with an organic solvent or alkaline water. Can do.
- the zinc halide phthalocyanine pigment composition of the present invention develops a bright green color with high color purity and high contrast with bluish green color. Therefore, it is suitable for coloring paints, plastics, printing inks, rubber, leather, textile printing, electronic toners, jet inks, thermal transfer inks and the like in addition to the color filters described in detail.
- Zinc halide phthalocyanine (B) was obtained in the same manner as in Production Example 1 except that the amount of bromine used was changed to 30 g. It was confirmed by fluorescent X-ray analysis that the halogenated zinc phthalocyanine (B) had an average halogenation rate of 6.9 bromine and 3.1 chlorine.
- Zinc halide phthalocyanine (C) was obtained in the same manner as in Production Example 1 except that the amount of bromine used was changed to 60 g. It was confirmed by fluorescent X-ray analysis that the halogenated zinc phthalocyanine (C) had an average halogenation rate of 10.2 bromine and 2.5 chlorine.
- Example 1 2.48 g of the green pigment composition (F) is dispersed with BYK-LPN6919 (1.24 g), DIC Corporation Unidic ZL-295 (1.86 g), propylene glycol monomethyl ether acetate (10.92 g), 0.3- Using 0.4 mm zircon beads, the mixture was dispersed for 2 hours with a paint shaker manufactured by Toyo Seiki Co., Ltd. to obtain a green colored composition (a). 4.0 g of green coloring composition (a), 0.98 g of Unidic ZL-295, 0.22 g of propylene glycol monomethyl ether acetate were added and mixed with a paint shaker to obtain a green composition (1) for evaluation. .
- This evaluation green composition (1) was spin-coated on soda glass and dried at 90 ° C. for 3 minutes to obtain an evaluation glass substrate.
- the obtained glass substrate for evaluation was heated at 230 ° C. for 1 hour to cure the coating film, and then the contrast ratio was measured using a contrast tester (CT-1 manufactured by Aisaka Electric Co., Ltd.).
- CT-1 contrast tester manufactured by Aisaka Electric Co., Ltd.
- Example 1 and Comparative Examples 1 and 2 are shown in Table 1. From Table 1, a green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with a halogenated zinc phthalocyanine pigment and an alkylene group has a bromine atom number of 6.9 bromine having a halogenation rate outside the scope of the present invention, chlorine It can be seen that the contrast ratio is improved by 10% or more as compared with the case where the derivative having 3.1 atoms is used or the case where no derivative is used.
- Example 2 Pigment Yellow 129 (manufactured by BASF, Irgadine Yellow L0800) 16.5 g using DISPERBYK-161 (manufactured by BYK Chemie) 3.85 g, propylene glycol monomethyl ether acetate 11.00 g using 0.3 to 0.4 mm zircon beads Then, the mixture was dispersed with a paint shaker manufactured by Toyo Seiki Co., Ltd. for 2 hours to obtain a colored composition (b). Coloring composition (b) 4.0 g, DIC Corporation Unidic ZL-295 0.98 g, propylene glycol monomethyl ether acetate 0.22 g, and mixing with a paint shaker (4) )
- Example 3 Chromaticity in C light source by heating a glass plate obtained by mixing, film-forming and drying the composition for evaluation (4) prepared in Example 1 and heating to 230 ° C. for 1 hour.
- a coating film showing (x, y) (0.265, 0.690) was produced.
- the brightness of this coating film was measured with CM-3500d manufactured by Konica Minolta, and the film thickness was measured with a real color confocal microscope OPTELICS C130 manufactured by Lasertec.
- Luminance and film thickness were measured in the same manner as in Example 3 except that the evaluation composition (1) was replaced with the evaluation composition (3) in Example 3.
- Table 2 shows the results of the brightness and film thickness of each coating film in Example 3 and Comparative Example 3. From Table 2, the green pigment composition comprising a halogenated zinc phthalocyanine pigment derivative having a phthalimide skeleton bonded with an alkylene group and a halogenated zinc phthalocyanine pigment has a reduced brightness and a film thickness as compared with the case where the derivative of the present invention is not added. It can be seen that there is no increase.
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Abstract
Description
である。
300mlフラスコに、塩化スルフリル(和光純薬工業試薬) 90g、塩化アルミニウム(関東化学試薬) 105g、塩化ナトリウム(東京化成工業試薬) 14g、DIC株式会社製 亜鉛フタロシアニン 27g、臭素(和光純薬工業試薬) 45gを仕込んだ。130℃まで昇温し、水に取り出した後、ろ過することによりハロゲン化亜鉛フタロシアニン(A)を得た。ハロゲン化亜鉛フタロシアニン(A)について蛍光X線分析により平均ハロゲン化率が臭素8.6個、塩素2.5個であることを確認した。
用いた臭素量を30gに変えた以外は製造例1と同様にして、ハロゲン化亜鉛フタロシアニン(B)を得た。ハロゲン化亜鉛フタロシアニン(B)について蛍光X線分析より平均ハロゲン化率が臭素6.9個、塩素3.1個であることを確認した。
用いた臭素量を60gに変えた以外は製造例1と同様にしてハロゲン化亜鉛フタロシアニン(C)を得た。ハロゲン化亜鉛フタロシアニン(C)について蛍光X線分析より平均ハロゲン化率が臭素10.2個、塩素2.5個であることを確認した。
製造例1で作製したハロゲン化亜鉛フタロシアニン(A)3gを硫酸(和光純薬工業試薬)27gに溶解し、フタルイミド(関東化学試薬)5g、パラホルムアルデヒド(関東化学試薬)2gを加えて80℃で反応させた後、水に取り出し、ろ過、洗浄を経てフタルイミドメチル化ハロゲン化亜鉛フタロシアニン(D)を得た。生成物の赤外線吸収スペクトルよりフタルイミドメチル基の平均置換基数は0.6個であることを確認した。
製造例2で作製したハロゲン化フタロシアニン(B)を用いたこと以外は製造例4と同様にしてフタルイミドメチル化ハロゲン化亜鉛フタロシアニン(E)を得た。生成物の赤外線吸収スペクトルより、フタルイミドメチル基の平均置換基数は1.0個であることを確認した。
ハロゲン化亜鉛フタロシアニン(C)20g、フタルイミドメチル化ハロゲン化亜鉛フタロシアニン(D)1g、粉砕した塩化ナトリウム140g、ジエチレングリコール32gを双腕型ニーダーに仕込み100℃で6時間混練した。混練後80℃の温水2kgに取り出し、1時間撹拌後、ろ過、湯洗、乾燥、粉砕することで緑色顔料組成物(F)を得た。
製造例6においてフタルイミドメチル化ハロゲン化亜鉛フタロシアニン(D)をフタルイミドメチル化ハロゲン化亜鉛フタロシアニン(E)に代えた以外は同様にして、緑色顔料組成物(G)を得た。
製造例6においてフタルイミドメチル化ハロゲン化亜鉛フタロシアニン(D)を用いないこと以外は同様にして緑色顔料組成物(H)を得た。
緑色顔料組成物(F)2.48gをビックケミー社製分散剤 BYK-LPN6919 1.24g、DIC(株)製 ユニディック ZL-295 1.86g、プロピレングリコールモノメチルエーテルアセテート 10.92gと共に0.3~0.4mmのジルコンビーズを用いて、東洋精機(株)製ペイントシェーカーで2時間分散して、緑色着色組成物(a)を得た。緑色着色組成物(a) 4.0g、ユニディック ZL-295 0.98g、プロピレングリコールモノメチルエーテルアセテート 0.22gを加えて、ペイントシェーカーで混合することで評価用緑色組成物(1)を得た。この評価用緑色組成物(1)をソーダガラスにスピンコートし、90℃で3分間乾燥し評価用ガラス基板を得た。得られた評価用ガラス基板を230℃で1時間加熱することで塗膜を硬化させた後、コントラストテスター(壷坂電気(株)製、CT-1)を用いてコントラスト比の測定を行った。なお、硬化後の塗膜の色度がC光源でy=0.430になるようにスピンコートの回転数を調整して、評価用ガラス基板を作製した。
実施例1において緑色顔料組成物(F)を製造例7で作製した緑色顔料組成物(G)に代えた以外は実施例1と同様にして評価用緑色組成物(2)とその評価用ガラス基板を作製した。
実施例1において緑色顔料組成物(F)を製造例8で作製した緑色顔料組成物(H)に代えた以外は実施例1と同様にして評価用緑色組成物(3)とその評価用ガラス基板を作製した。
表1から、ハロゲン化亜鉛フタロシアニン顔料とアルキレン基で結合されたフタルイミド骨格を有するハロゲン化亜鉛フタロシアニン顔料誘導体からなる緑色顔料組成物はハロゲン化率が本願範囲からはずれる臭素原子数6.9個、塩素原子数3.1個からなる誘導体を使用した場合や誘導体を使用しない場合に比べて、コントラスト比が10%以上向上していることがわかる。
ピグメントイエロー129(BASF社製、イルガジンイエローL0800) 16.5gをDISPERBYK-161(ビックケミー社製) 3.85g、プロピレングリコールモノメチルエーテルアセテート 11.00gと共に0.3~0.4mmのジルコンビーズを用いて、東洋精機(株)製ペイントシェーカーで2時間分散して、着色組成物(b)を得た。着色組成物(b) 4.0g、DIC(株)製ユニディックZL-295 0.98g、プロピレングリコールモノメチルエーテルアセテート 0.22gを加えて、ペイントシェーカーで混合することで調色用組成物(4)を得た。
調色用組成物(4)と実施例1で作製した評価用組成物(1)を混合、製膜、乾燥して得たガラス板を230℃で1時間加熱する事でC光源における色度(x、y)=(0.265,0.690)を示す塗膜を作製した。この塗膜についてコニカミノルタ社製CM-3500dで輝度を測定し、レーザーテック社製リアルカラー共焦点顕微鏡OPTELICS C130で膜厚を測定した。
実施例3において評価用組成物(1)を評価用組成物(3)に代えた以外は実施例3と同様にして輝度及び膜厚を測定した。
表2からハロゲン化亜鉛フタロシアニン顔料とアルキレン基で結合されたフタルイミド骨格を有するハロゲン化亜鉛フタロシアニン顔料誘導体からなる緑色顔料組成物は、本願発明の誘導体を添加しない場合と比べて輝度の低下、膜厚の増大は無いことがわかる。
Claims (5)
- 前記ハロゲン化亜鉛フタロシアニン顔料が、1分子中にハロゲン原子を平均10~14個有し、そのうち臭素原子数が平均8~12個であり、塩素原子数が平均2~5個である請求項1に記載のカラーフィルタ用緑色顔料組成物。
- 更に黄色顔料を含有することを特徴とする請求項1または請求項2記載のカラーフィルタ用緑色顔料組成物。
- 請求項1~3いずれか一項記載のカラーフィルタ用顔料組成物を含有するカラーフィルタ。
- ソルベントソルトミリングによる請求項1~3いずれか一項記載のカラーフィルタ用顔料組成物の製造方法。
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