WO2013147422A1 - 크산텐계 자색 염료 화합물, 이를 포함하는 컬러필터용 착색 수지 조성물 및 이를 이용한 컬러필터 - Google Patents
크산텐계 자색 염료 화합물, 이를 포함하는 컬러필터용 착색 수지 조성물 및 이를 이용한 컬러필터 Download PDFInfo
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- WO2013147422A1 WO2013147422A1 PCT/KR2013/001565 KR2013001565W WO2013147422A1 WO 2013147422 A1 WO2013147422 A1 WO 2013147422A1 KR 2013001565 W KR2013001565 W KR 2013001565W WO 2013147422 A1 WO2013147422 A1 WO 2013147422A1
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- 0 CC*(CC)c(cc1)cc(O2)c1C(c1c(*C)cccc1)=C(C=C1)C2=CC1=*(CC)CC Chemical compound CC*(CC)c(cc1)cc(O2)c1C(c1c(*C)cccc1)=C(C=C1)C2=CC1=*(CC)CC 0.000 description 2
- CVAVMIODJQHEEH-UHFFFAOYSA-O CCN(CC)c(cc1O2)ccc1C(c(cccc1)c1C(O)=O)=C(C=C1)C2=CC1=[N+](CC)CC Chemical compound CCN(CC)c(cc1O2)ccc1C(c(cccc1)c1C(O)=O)=C(C=C1)C2=CC1=[N+](CC)CC CVAVMIODJQHEEH-UHFFFAOYSA-O 0.000 description 1
Classifications
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- 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
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
- C09B11/10—Amino derivatives of triarylmethanes
- C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- C08L33/04—Homopolymers or copolymers of esters
- C08L33/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur, or oxygen atoms in addition to the carboxy oxygen
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B57/00—Other synthetic dyes of known constitution
- C09B57/14—Benzoxanthene dyes; Benzothioxanthene dyes
-
- 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
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- 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
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
- C09B69/101—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing an anthracene dye
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/201—Filters in the form of arrays
-
- 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
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- 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
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- 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
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- 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
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/34—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate
- C08F220/36—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate
- C08F220/365—Esters containing nitrogen, e.g. N,N-dimethylaminoethyl (meth)acrylate containing oxygen in addition to the carboxy oxygen, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate containing further carboxylic moieties
Definitions
- the present invention relates to a purple dye compound for color filters and a colored resin composition for color filters comprising the same, and more particularly, a novel xanthene-based purple dye having excellent solubility, high heat resistance, light resistance and chemical resistance to an organic solvent. It relates to a compound or a polymer thereof, a color resin composition for a color filter comprising the same, and a color filter using the same.
- Liquid crystal displays display images using optical and electrical properties of liquid crystal materials.
- the liquid crystal display device has advantages such as light weight, low power, low driving voltage, and the like compared to a CRT, a plasma display panel, and the like.
- the liquid crystal display device includes a liquid crystal layer positioned between glass substrates. Light generated from the light source passes through the liquid crystal layer, and the liquid crystal layer controls light transmittance. The light passing through the liquid crystal passes through the color filter layer and implements a full color screen by additive mixing using light passing through the color filter layer.
- dyeing, printing, electrodeposition, and pigment dispersing methods are known as color filter manufacturing methods for liquid crystal display devices.
- methods of using dyes have been studied.
- heat resistance, light resistance, It is difficult to apply because of low chemical resistance, etc., compared to pigments, and the pigment dispersion method is generally applied at present because there is no economical efficiency due to a complicated process in the dyeing method.
- Pigments are less transparent than dyes but have been overcome by advances in pigment miniaturization and dispersion techniques. Since the color filter manufactured by the pigment dispersion method uses pigments, it is stable against light, heat, solvents, etc., and when patterned by photolithography, it is easy to manufacture color filters for large screens and high-precision color displays. have.
- Pigments used in the pigment-disperse color resists include red, green, and blue pigments, respectively, when forming an RGB color filter, and in general, yellow pigments, purple pigments, and the like may be further included in order to express colors more effectively.
- a color resist solution is first applied onto a substrate by a spin coater and dried to form a coating film. Subsequently, a color pixel is obtained by pattern exposure and development of a coating film, it heat-processes at high temperature, the pattern of a 1st color is obtained, and this operation is repeated according to the number of colors, and a color filter is produced.
- the most important factors influencing the performance of the color resist are the properties of the pigment used as the colorant, its dispersibility, and the dispersion state. Recently, with the increase in size and high definition of LCDs, the demand characteristics of color filters such as high transmittance of color layer, high contrast ratio, narrow black matrix width and high reliability are increasing every year. As a means for satisfying these requirements, color pigments such as brightness and contrast ratio have been satisfied by miniaturizing the pigment as far as possible.
- the pigment in the case of the pigment dispersion, the pigment is present in the form of particles, which not only scatters the light, but also causes the pigment surface area to increase rapidly due to the miniaturization of the pigment, resulting in uneven pigment particles due to deterioration of dispersion stability. It is recognized that it has reached the limit that is difficult to meet high quality requirements such as high brightness, high contrast ratio, and high resolution required.
- high quality requirements such as high brightness, high contrast ratio, and high resolution required.
- a pigmentation process such as salt milling is required, and such a post-treatment process may be undesirable in terms of environmental protection.
- many additives such as dispersants and pigment derivatives are required to stabilize the dispersion state, and production is possible only after a very difficult and cumbersome manufacturing process.
- pigment dispersions require difficult storage and transportation conditions in order to maintain optimal quality.
- the problem to be solved by the present invention is to solve the above problems, a novel xanthene violet having excellent solubility in organic solvents, especially propylene glycol monomethyl ether acetate, having heat resistance, light resistance, chemical resistance and high brightness It is to provide a dye compound and a colored resin composition for color filters comprising the same.
- the present invention to solve the above problems,
- xanthene-based purple dye compound represented by the following [Formula 1] which is a polymerizable monomer.
- X - is selected from a halogenide anion, a perhalogenate anion, a fluorine anion, an alkyl sulfate anion, a sulfonate anion and a sulfonimide anion,
- R 1 , R 2 , R 3 and R 4 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 48 carbon atoms, and a substituted or unsubstituted carbon atom 6
- aromatic hydrocarbons of 10 to 10
- R 5 is a substituted or unsubstituted saturated hydrocarbon having 1 to 10 carbon atoms
- R 6 is hydrogen or a methyl group.
- the purple dye polymer compound obtained by using the xanthene type compound represented by following [Formula 2] as a monomer is provided.
- X - is selected from a halogenide anion, a perhalogenate anion, a fluorine anion, an alkyl sulfate anion, a sulfonate anion and a sulfonimide anion,
- R 7 , R 8 , R 9 and R 10 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 48 carbon atoms, and a substituted or unsubstituted carbon atom 6 To aromatic hydrocarbons of 10 to 10,
- R 11 is a substituted or unsubstituted saturated hydrocarbon having 1 to 10 carbon atoms
- R 12 is hydrogen or a methyl group
- the polymer compound may have a weight average molecular weight (Mw) of 2,000-150,000.
- the purple dye compound is a purple dye compound represented by the above [Formula 1] according to claim 1; Or a purple dye polymer compound obtained by using the compound represented by the above [Formula 2] according to claim 2 as a monomer; it provides a colored resin composition for a color filter.
- the purple dye compound may be 0.01% by weight to 50% by weight relative to the total weight of the colored resin composition.
- the blue pigment may be a copper phthalocyanine-based blue pigment.
- the weight ratio of the blue pigment and the purple dye compound may be 99: 1-50: 50.
- the reactive unsaturated compound is a thermosetting monomer or oligomer; Photocurable monomers and oligomers; And it may be selected from the group consisting of a combination thereof.
- the polymerization initiator may be selected from the group consisting of a thermal polymerization initiator, a photopolymerization initiator and a combination thereof.
- the present invention to solve the above problems,
- It provides a color filter, characterized in that manufactured using the colored resin composition for color filters.
- the dye compound or polymer compound thereof according to the present invention has excellent solvent resistance and excellent mixing property with the pigment with respect to the organic solvent, and also has excellent heat resistance, chemical resistance, light resistance and brightness due to the polymer structure, It is possible to manufacture a color filter having excellent chemical resistance, light resistance and brightness.
- the present invention is characterized by improving the solvent resistance by introducing an anion having a high solubility to xanthene dyes, and includes a functional group capable of polymerizing in the molecule, that is, polymerizable, can be polymerized, the coloring composition comprising the same It is possible to realize a color filter having excellent heat resistance, less color change and excellent color characteristics.
- the purple dye compound according to the present invention may be a xanthene-based purple dye compound represented by the following [Formula 1] as a polymerizable monomer.
- X - is selected from a halide anion, a perhalogenate anion, a fluorine anion, an alkyl sulfate anion, a sulfonate anion and a sulfonimide anion, preferably trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion Can be.
- R 1 , R 2 , R 3 and R 4 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably a substituted or unsubstituted alkyl group having 1 to 10;
- it may be selected from a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- R 5 may be a substituted or unsubstituted saturated hydrocarbon having 1 to 10 carbon atoms, and R 6 may be hydrogen or a methyl group.
- the purple dye compound according to the present invention may be a purple dye polymer compound obtained by using a xanthene-based compound represented by the following [Formula 2] as a monomer.
- X ⁇ is selected from a halogenide anion, a perhalogenate anion, a fluorine anion, an alkyl sulfate anion, a sulfonate anion and a sulfonimide anion, preferably trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion Can be.
- R 7 , R 8 , R 9 and R 10 are each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, preferably a substituted or unsubstituted alkyl group having 1 to 10;
- it may be selected from a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms.
- R 11 may be a substituted or unsubstituted saturated hydrocarbon having 1 to 10 carbon atoms, and R 12 may be hydrogen or a methyl group.
- the polymer compound may have a weight average molecular weight (Mw) of 2,000-150,000, preferably 2,000-30,000.
- the colored resin composition for color filters according to the embodiment of the present invention includes a blue pigment, a binder resin, a reactive unsaturated compound, a polymerization initiator, an organic solvent, and an additive together with the purple dye compound.
- the purple dye compound may be a monomer compound according to [Formula 1] or a polymer compound according to [Formula 2], and may be included in an amount of 0.01 wt% to 50 wt% based on the total weight of the colored resin composition.
- the said purple dye compound is contained in the said range, it is excellent in solubility to a solvent, has high brightness, and is excellent in heat resistance and light resistance.
- the monomer compound according to [Formula 1] or the polymer compound according to [Formula 2], which is the purple dye compound may be used together with one or more blue pigments, and the blue pigments are generally used in colored resin compositions for color filters.
- One or more of the blue pigments used may be selected and used, and among them, a copper phthalocyanine-based blue pigment may be included.
- blue pigments include compounds classified as pigments in the Color Index, published by The Society of Dyers and Colourists. Specific examples include C.I. Color Index Pigment Blue 1, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 60 and the like.
- the weight ratio of the blue pigment and the purple dye compound may be 99: 1-50-50.
- the binder resin is not particularly limited as long as it is a resin capable of exhibiting binding force, and a known film-forming resin is particularly useful.
- cellulose resins in particular carboxymethylhydroxyethyl cellulose and hydroxyethyl cellulose, acrylic acid resins, alkyd resins, melamine resins, epoxy resins, polyvinyl alcohols, polyvinyl pyrrolidones, polyamides, polyamide-imines, Binders, such as polyimide, are useful.
- Useful binder resins also include resins having photopolymerizable unsaturated bonds, which may be, for example, acrylic resins.
- resins having photopolymerizable unsaturated bonds which may be, for example, acrylic resins.
- homopolymers and copolymers of polymerizable monomers such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, styrene and styrene derivatives, methacrylic acid, itaconic acid, maleic acid, male Copolymers between anhydrides, polymerizable monomers containing carboxyl groups such as monoalkyl maleates and polymerizable monomers such as methacrylic acid, styrene and styrene derivatives are useful.
- Examples include compounds containing an oxirane ring and an ethylenically unsaturated compound, for example, glycidyl (meth) acrylate, acryloyl glycidyl ether and monoalkylglycidyl itaconate and the like carboxyl- Reaction products of the containing polymerized compounds, and compounds each containing a hydroxyl group and an ethylenically unsaturated compound (unsaturated alcohol), for example, allyl alcohol, 2-butene-4-ol, oleyl alcohol, 2-hydroxyethyl
- reaction products of (meth) acrylate, N-methylolacrylamide and the like and a carboxyl-containing polymerized compound and such a binder may contain an unsaturated compound having no isocyanate group.
- the equivalent of the degree of unsaturation of the binder is generally 200 to 3,000, preferably 230 to 1,000, in order to provide film hardness as well as suitable photopolymerization.
- the acid value is generally 20 to 300, preferably 40 to 200.
- the average molecular weight of the binder is preferably 1,500 to 200,000, particularly 10,000 to 50,000 g / mol.
- the reactive unsaturated compound may be selected from the group consisting of a thermosetting monomer or oligomer, a photocurable monomer or oligomer, and a combination thereof, preferably the photocurable monomer, at least one reactive double bond and further reactive in the molecule It may contain a group.
- Useful photocurable monomers in this connection are in particular reactive solvents or reactive diluents, for example mono-, di-, tri- and polyfunctional acrylates and methacrylates, vinyl ethers, glycidyl ethers and the like. Additional reactive groups include aryl, hydroxyl, phosphate, urethanes, secondary amines, N-alkoxymethyl groups and the like.
- Monomers of this kind are known in the art and are described, for example, in Roempp, Lexikon, Lacke und Druckmaschine, Dr. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 491/492.
- the choice of monomer depends in particular on the type and intensity of irradiation used, the desired reaction by the photoinitiator and the film properties.
- These photocurable monomers can also be used individually or in combination of monomers.
- the polymerization initiator may be a thermosetting initiator, a photocuring initiator or a combination thereof, preferably a photocuring initiator, such a photocuring initiator, the absorption of visible or left ultraviolet light, for example the monomer and And / or a compound that forms a reaction intermediate capable of inducing a polymerization reaction of the binder.
- Photocuring initiators or are known in the art and described, for example, in Roempp, Lexikon, Lacke und Druckmaschine, Dr. Ulrich Zorll, Thimem Verlag Stuttgart-New York, 1998, p 445/446.
- the organic solvents are, for example, ketones, alkylene glycol ethers, alcohols and aromatic compounds.
- the ketone group includes acetone, methyl ethyl ketone, cyclohexanone and the like
- the alkylene glycol ether group includes methyl cellosolve (ethylene glycol monomethyl ether), butyl cellosolve (ethylene glycol monobutyl ether) and methyl solosolve acetate , Ethyl cellosolve acetate, butyl cellosolve acetate, ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol dimethyl ether, diethylene glycol ethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol Monopropyl ether, propylene glycol monobutyl ether, propylene glycol monomethyl ether acetate diethylene glycol methyl ether acetate,
- the aromatic compound group includes benzene, toluene, xylene, N-methyl-2-pyrrolidone, ethyl N-hydroxymethylpyrrolidone-2 acetate and the like.
- Further other solvents include 1,2-propanediol diacetate, 3-methyl-3-methyl-3methoxybutyl acetate, ethyl acetate, tetrahydrofuran and the like. The above organic solvents may be used alone or in a mixture.
- the additive may be used without limitation as long as it meets each purpose, and in order to improve the surface texture, fatty acids, fatty amines, alcohols, bean oils, waxes, rosins, resins, benzotriazole derivatives, and the like may be used.
- Stearic acid or Behenic acid may be used as the fatty acid, and more preferably Stearylamine or the like may be used as the fatty amine.
- PGMEA Propylene glycol monomethyl ether acetate
- the dye compounds of Synthesis Examples 1 to 4 according to the present invention exhibit high solubility in various solvents.
- the compounds of Synthesis Examples 1 and 2 exhibit very high solubility in all solvents.
- Each of the photosensitive resin compositions was applied to a glass substrate having a thickness of 1 mm at a thickness of 2 ⁇ m, and dried for 90 seconds on a hot plate at 80 ° C. to form a coating film. After the glass substrate was placed in a 230 ° C. hot air dryer, it was left for 30 minutes, 1 hour, and 2 hours, and then the absorbance change rate at the maximum absorption wavelength was measured using UV / VIS Spectrophotometer: Agilent 8453 (Agilent). Is shown in the following [Table 2].
- Examples 1 to 4 coated film according to the present invention can be seen that the change rate with time changes at high temperature is small and excellent in heat resistance and durability.
- the photosensitive blue resin composition was manufactured with the following composition.
- a colored resin composition was prepared in the same manner as in the compositions of Examples 1 to 4, except that the compounds of Comparative Examples 1 to 3 were added instead of the compounds of Synthesis Examples 1 to 4.
- the dye compound or polymer compound thereof according to the present invention has excellent solvent resistance and excellent mixing property with the pigment with respect to the organic solvent, and also has excellent heat resistance, chemical resistance, light resistance and brightness due to the polymer structure, Industrial applications are expected because color filters with excellent chemical properties, light resistance and brightness can be manufactured.
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Abstract
Description
용매 | 합성예 1 | 합성예 2 | 합성예 3 | 합성예 4 | 비교예 1 | 비교예 2 | 비교예 3 |
PGMEA | >10% | >10% | 0.6% | 0.8% | < 0.1% | < 0.1% | 0.4% |
PGME | >10% | >10% | 6.5% | 7.2% | 1.2% | 1.4% | 4.5% |
시클로헥사논 | >10% | >10% | >10% | >10% | 0.4% | 0.5% | 6.3% |
온도 | 평가 | 합성예1 | 합성예2 | 합성예3 | 합성예4 | 비교예1 | 비교예2 | 비교예3 |
80℃ | 초기 | 0.7023 | 0.6322 | 0.6394 | 0.7610 | 0.7821 | 0.7314 | 0.6058 |
230℃ | 30분 | 0.6789 | 0.6178 | 0.6049 | 0.5747 | 0.6212 | 0.6012 | 0.5498 |
변화율 | 96.7% | 97.7% | 94.6% | 94.4% | 79.4% | 82.2% | 90.8% | |
60분 | 0.6571 | 0.5947 | 0.5829 | 0.5642 | 0.4712 | 0.4481 | 0.5198 | |
변화율 | 93.6% | 94.1% | 91.2% | 92.7% | 60.2% | 61.3% | 85.8% | |
120분 | 0.6210 | 0.5690 | 0.5392 | 0.5186 | 0.3461 | 0.3661 | 0.4598 | |
변화율 | 88.4% | 90.0% | 84.3% | 85.2% | 44.3% | 50.1% | 75.9% |
구분 | 색좌표(x) | 색좌표(y) | 휘도(Y) |
실시예1 | 0.1350 | 0.113 | 13.59 |
실시예2 | 0.1360 | 0.113 | 13.61 |
실시예3 | 0.1359 | 0.113 | 13.57 |
실시예4 | 0.1364 | 0.113 | 13.65 |
비교예3 | 0.1365 | 0.113 | 13.36 |
Claims (12)
- 중합 가능한 단량체인 하기 [화학식 1]로 표시되는 크산텐계 자색 염료 화합물:[화학식 1]상기 [화학식 1]에서,상기 X-는 할론겐 음이온, 과할로겐산 음이온, 플루오르 착음이온, 알킬설페이트 음이온, 설폰산염 음이온 및 설폰 이미드 음이온 중에서 선택되고,상기 R1, R2, R3 및 R4는 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 48의 알케닐기 및 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소 중에서 선택되며,상기 R5는 치환 또는 비치환된 탄소수 1 내지 10의 포화 탄화수소이고,상기 R6은 수소 또는 메틸기이다.
- 하기 [화학식 2]로 표시되는 크산텐계 화합물을 단량체로 하여 얻어지는 자색 염료 폴리머 화합물:[화학식 2]상기 [화학식 2]에서,상기 X-는 할론겐 음이온, 과할로겐산 음이온, 플루오르 착음이온, 알킬설페이트 음이온, 설폰산염 음이온 및 설폰 이미드 음이온 중에서 선택되고,상기 R7, R8, R9 및 R10은 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 30의 알킬기, 치환 또는 비치환된 탄소수 2 내지 48의 알케닐기 및 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소 중에서 선택되며,상기 R11은 치환 또는 비치환된 탄소수 1 내지 10의 포화 탄화수소이고,상기 R12는 수소 또는 메틸기이다.
- 제2항에 있어서,상기 폴리머 화합물은 중량평균분자량(Mw)이 2,000-150,000인 것을 특징으로 하는 자색 염료 폴리머 화합물.
- 자색 염료 화합물; 청색 안료; 바인더 수지; 반응성 불포화 화합물; 중합 개시제; 유기용제; 및 첨가제;를 포함하고,상기 자색 염료 화합물은 제1항에 따른 상기 [화학식 1]로 표시되는 자색 염료 화합물; 또는 제2항에 따른 상기 [화학식 2]로 표시되는 화합물을 단량체로 하여 얻어지는 자색 염료 폴리머 화합물;인 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 있어서,상기 자색 염료 화합물은 상기 착색 수지 조성물 총중량에 대하여 0.01 중량% 내지 50 중량%인 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 있어서,상기 청색 안료는 구리프탈로시아닌계 청색 안료인 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 있어서,상기 청색 안료와 상기 자색 염료 화합물의 중량비가 99 : 1 - 50 : 50 인 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 있어서,상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머; 광경화성 단량체나 올리고머; 및 이들의 조합으로 이루어진 군에서 선택되는 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 있어서,상기 중합 개시제는 열중합 개시제, 광중합 개시제 및 이들의 조합으로 이루어진 군에서 선택되는 것을 특징으로 하는 컬러필터용 착색 수지 조성물.
- 제6항에 따른 컬러필터용 착색 수지 조성물을 이용하여 제조된 것을 특징으로 하는 컬러필터.
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KR20130111023A (ko) | 2013-10-10 |
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