WO2014196770A1 - 청색 염료 화합물, 이를 포함하는 컬러필터용 청색 수지 조성물 및 이를 이용한 컬러필터 - Google Patents
청색 염료 화합물, 이를 포함하는 컬러필터용 청색 수지 조성물 및 이를 이용한 컬러필터 Download PDFInfo
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- WO2014196770A1 WO2014196770A1 PCT/KR2014/004884 KR2014004884W WO2014196770A1 WO 2014196770 A1 WO2014196770 A1 WO 2014196770A1 KR 2014004884 W KR2014004884 W KR 2014004884W WO 2014196770 A1 WO2014196770 A1 WO 2014196770A1
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- color filter
- resin composition
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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
- C09B57/00—Other synthetic dyes of known constitution
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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
- C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
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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
- G02B5/22—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
- G03F7/0046—Photosensitive materials with perfluoro compounds, e.g. for dry lithography
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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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- 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
Definitions
- the present invention relates to a blue dye compound for color filters, and more particularly, to a novel triarylmethane dye compound having improved solubility and high heat resistance compared to a conventional dye, a blue resin composition for color filters including the same, and using the same It relates to a color filter.
- the liquid crystal display displays an image by using optical and electrical properties of the liquid crystal material.
- 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.
- the color filter produced by the pigment dispersion method is stable to light, heat, solvents, etc., because it uses pigment, and when used by photolithography, it is easy to manufacture color filters for large screens and high-precision color displays. .
- Pigments used in the pigment dispersion type color resist 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 to express colors more effectively.
- a color resist solution is first applied onto a substrate by a spin coater, and then 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 powder obtained by the synthesis cannot be used as it is in order to facilitate stable dispersion and miniaturization, and a micronization step such as salt milling is required, and such a post-treatment step is undesirable in terms of environmental protection.
- a micronization step such as salt milling is required, and such a post-treatment step is 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 optimum quality.
- 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, thereby producing color resists due to the generation of uneven pigment particles due to deterioration of dispersion stability. There is a difficulty.
- triarylmethane dye has a high transmittance at 420-450 nm of the color filter, and is excellent in color characteristics as a blue colorant for color filters, but is poor in solubility in solvents used in color compositions for color filters, and is poor in heat resistance. There is this.
- propylene glycol monomethyl ether acetate PGMEA
- propylene glycol monomethyl ether PGME
- cyclohexanone cyclohexanone, and the like are commonly used as the solvent used in the coloring composition for color filters.
- solubility in cyclohexanone is easy to secure, but solubility in PGMEA or PGME has a low problem.
- cyclohexanone is prohibited from being used as an environmentally harmful substance, which requires a dye having high solubility in PGMEA or PGME.
- the problem to be solved by the present invention is to solve the above problems, the blue compound of the triaryl methane dyes excellent in color characteristics, such as low solubility and heat resistance to PGMEA in blue solubility, heat resistance blue To provide a dye compound.
- the present invention also provides a blue resin composition for a color filter comprising the blue dye compound and a color filter using the same.
- the present invention provides a triarylmethane blue dye compound represented by the following [Formula 1] to solve the above problems.
- X ⁇ is trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion.
- R 1 to R 7 are the same as or different from each other, and are each independently selected from hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted aromatic hydrocarbon having 6 to 10 carbon atoms, and R 1 , R 2 , R 3, R 4 and R 7 are Each independently may be R 8 represented by the following [formula 1], and at least one of R 1 , R 2 , R 3, R 4, and R 7 is R 8 represented by [formula 1].
- n is an integer from 1 to 10 and R 9 is hydrogen or methyl.
- R 1 may be connected to R 2 and R 3 to R 4 to form a saturated or unsaturated ring.
- a, b and c are each independently an integer of 0 to 4, and m is an integer of 1 to 10.
- R 5 and R 6 may each independently be a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms or halogen.
- the present invention includes a blue dye compound, a binder resin, a reactive unsaturated compound, a polymerization initiator, an organic solvent and an additive, in order to solve the above problems, the blue dye compound is triaryl methane represented by the above [Formula 1] It is a blue dye compound, The blue resin composition for color filters is provided.
- the blue dye compound of the present invention may further include at least one selected from xanthene dyes, cyanine dyes and azapopyrine dyes together with the triarylmethane blue dye compound represented by the above [Formula 1].
- the blue dye compound of the present invention may be 0.01% to 50% by weight relative to the total weight of the blue resin composition.
- the blue resin composition for a color filter according to the present invention may further include a blue pigment as necessary, and the blue pigment may be a copper phthalocyanine-based blue pigment.
- the binder resin according to the present invention is not particularly limited as long as it is a resin capable of exhibiting a binding force, and may be a known film-forming resin.
- the reactive unsaturated compound of the present invention may be selected from the group consisting of a thermosetting monomer or oligomer, a photocurable monomer or oligomer and a combination thereof.
- the polymerization initiator of the present invention may be selected from the group consisting of a thermosetting initiator, a photocuring initiator and a combination thereof.
- the present invention provides a color filter, characterized in that it was manufactured using the blue resin composition for color filters in order to solve the above problems.
- the triarylmethane blue dye compound according to the present invention has excellent solubility and high heat resistance to propylene glycol monomethyl ether acetate (PGMEA). Therefore, when using the triarylmethane blue dye compound according to the present invention, it is possible to produce a color filter of high brightness, high contrast ratio compared to the color filter using a conventional pigment.
- PMEA propylene glycol monomethyl ether acetate
- a dye having a higher luminance than a pigment has been developed.
- a dye is generally inferior in heat resistance to a pigment and generally has low solubility in an organic solvent used in the color filter.
- the solubility in an organic solvent is high and it is difficult to satisfy high heat resistance and high brightness at the same time. Also, dyes satisfying reliability are rare.
- the blue dye compound according to the present invention is a blue colorant for color filters, which improves the solubility and heat resistance of triarylmethane having excellent color characteristics, and is suitable for use in the blue composition of color filters.
- the blue dye compound according to the present invention is characterized by being a triarylmethane compound represented by the following [Formula 1].
- X ⁇ is trifluoromethanesulfonic acid or bistrifluoromethanesulfonimide anion
- R 1 to R 7 are the same as or different from each other, and each independently hydrogen, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, substituted or unsubstituted Ring is one selected from aromatic hydrocarbons having 6 to 10 carbon atoms, R 1 , R 2 , R 3, R 4 and R 7
- R 8 represented by the following [formula 1]
- at least one of R 1 , R 2 , R 3, R 4, and R 7 is R 8 represented by [formula 1].
- n is an integer from 1 to 10 and R 9 is hydrogen or methyl.
- R 1 may be connected to R 2 and R 3 to R 4 to form a saturated or unsaturated ring.
- a, b and c are each independently an integer of 0 to 4, and m is an integer of 1 to 10.
- R 5 and R 6 may each independently be a substituted or unsubstituted alkoxy group having 1 to 10 carbon atoms or halogen.
- the blue resin composition for color filters according to the present invention includes the blue dye compound, a binder resin, a reactive unsaturated compound, a polymerization initiator, an organic solvent, and an additive, and may further include a blue pigment, if necessary.
- the blue dye compound may optionally further include one or more other dyes together with the triarylmethane compound represented by [Formula 1], and the other dyes to be additionally included are generally xanthenes used in the color filter blue resin composition. Dyes, cyanine dyes, azapopyrine dyes, and the like.
- the blue dye compound optionally comprising at least one other dye together with the compound according to [Formula 1] may be included in 0.01% to 50% by weight relative to the total weight of the blue resin composition, if the blue dye compound is included in the above range It is excellent in solubility in solvents and excellent in heat resistance.
- the blue pigment may be used by selecting one or more of the blue pigments generally used in the conventional colored resin composition for color filters, and may include a copper phthalocyanine-based blue pigment.
- the copper phthalocyanine-based 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 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.
- the binder includes a resin having a photopolymerizable unsaturated bond, and may be, for example, an acrylic resin.
- a resin having a photopolymerizable unsaturated bond may be, for example, an acrylic resin.
- 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 carboxylic 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 methacrylate, acryloyl glycidyl ether and monoalkylglycidyl itaconate and the like and carboxyl-containing polymerizations.
- Reaction products of the compounds also compounds containing hydroxyl groups and ethylenically unsaturated compounds (unsaturated alcohols), for example allyl alcohol, 2-butene-4-ol, oleyl alcohol, 2-hydroxyethyl methacryl Latex, N-methylolacrylamide and the like) and a carboxyl-containing polymerized compound, and such a binder may contain an unsaturated compound free of isocyanate groups.
- unsaturated alcohols for example allyl alcohol, 2-butene-4-ol, oleyl alcohol, 2-hydroxyethyl methacryl Latex, N-methylolacrylamide and the like
- the equivalent amount of unsaturation of the binder (molecular weight of binder per unsaturated compound) is generally in the range of 200 to 3,000, in particular in the range of 230 to 1,000, in order to provide not only suitable photopolymerization but also film hardness.
- the acid value is generally 20 to 300, in particular 40 to 200, to provide sufficient alkali developability after film exposure.
- 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 May contain groups.
- 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, urethane, 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, and such photocuring initiator may be a result of absorption of visible or ultraviolet light, for example, the monomer and / or A compound that forms a reaction intermediate capable of inducing a polymerization reaction of a binder.
- Photoinitiators or 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 445/446.
- Such 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 solosorbe acetate.
- aromatic solvent groups include 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. These solvents can be used alone or in mixtures.
- Such additional additives may be used without limitation as long as they meet the respective purpose.
- fatty acids, fatty amines, alcohols, bean oils, waxes, rosins, resins, benzotriazole derivatives, and the like may be used to improve surface texture. More preferably, as the fatty acid, Stearic acid or Behenic acid may be used, and as the fatty amine, Stearylamine may be used.
- N, N-diethylaminobenzoic acid and 100 g of toluene were added and stirred. Thereafter, 0.400 mol of thionyl chloride was added dropwise, and then heated to 80 ° C, followed by reaction for 1 hour. After the reaction, distillation under reduced pressure was carried out to remove thionyl chloride and toluene to obtain N, N-diethylaminobenzoyl chloride.
- the blue dye compounds of [Formula 2] to [Formula 7] of Synthesis Examples 1 to 6 according to the present invention can be confirmed to have a high solubility of 5% or more in PGMEA, Comparative Example In the case of 2, it can be seen that PGMEA ⁇ 1% solubility is quite low.
- Comparative Example 1 in which Comparative Example 2 was substituted with p-toluenesulfonic acid sodium salt the solubility was improved compared to Comparative Example 2, but it can be seen that it is considerably lower than the compound according to the present invention.
- the blue dye compound according to the present invention has excellent solubility in organic solvents such as PGMEA.
- the photosensitive blue resin composition was manufactured with the following composition.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of the compound of Synthesis Example 2 was used as a blue dye compound.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of the compound of Synthesis Example 3 was used as a blue dye compound.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of a compound of Synthesis Example 4 was used as a blue dye compound.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of a compound of Synthesis Example 5 was used as a blue dye compound.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of a compound of Synthesis Example 6 was used as a blue dye compound.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that Compound [Comparative Example 1] was used instead of Synthesis Example 1.
- a photosensitive blue resin composition was prepared in the same manner as in Example 1, except that 2.3 g of a Basic Blue 7 compound was added instead of Synthesis Example 1.
- the blue resin compositions for color filters prepared in Examples and Comparative Examples were spin-coated to a thickness of 2 ⁇ m on a 10 cm ⁇ 10 cm glass substrate, respectively, and prebaked for 3 minutes on a 90 ° C. hot plate. -bake) and then cooled at room temperature for 1 minute. This was exposed at an exposure amount (365 nm standard) of 100 mJ / cm 2 using an exposure machine.
- the triarylmethane blue dye compound according to the present invention has excellent solubility and high heat resistance to propylene glycol monomethyl ether acetate (PGMEA). Therefore, when using the triarylmethane blue dye compound according to the present invention, it is possible to produce a color filter of high brightness, high contrast ratio compared to the color filter using a conventional pigment.
- PMEA propylene glycol monomethyl ether acetate
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Abstract
Description
합성예 | 반응물 1 | 반응물 2 | 생성물 |
2 | 화학식 Ⅵ | (A) | 화학식 3 |
3 | 화학식 Ⅶ | (A) | 화학식 4 |
4 | 화학식 Ⅴ | (B) | 화학식 5 |
5 | 화학식 Ⅵ | (B) | 화학식 6 |
6 | 화학식 Ⅶ | (B) | 화학식 7 |
구분 | 합성예 | 비교예 | ||||||
1 | 2 | 3 | 4 | 5 | 6 | 1 | 2 | |
PGMEA | >5% | >5% | >5% | >5% | >5% | >5% | >1% | <1% |
구분 | 실시예 | 비교예 | ||||||
1 | 2 | 3 | 4 | 5 | 6 | 3 | 4 | |
Eab* | 2.25 | 2.07 | 2.54 | 2.60 | 2.54 | 2.78 | 17.84 | 31.69 |
Claims (11)
- 하기 [화학식 1] 표시되는 트리아릴메탄 청색 염료 화합물:[화학식 1]상기 [화학식 1]에서,X-는 트리플루오르메탄술폰산 또는 비스트리플루오르메탄술폰이미드 음이온이고,R1 내지 R7은 서로 동일하거나 상이하고, 각각 독립적으로 수소, 치환 또는 비치환된 탄소수 1 내지 10의 알킬기, 치환 또는 비치환된 탄소수 6 내지 10의 방향족 탄화수소 중에서 선택되는 하나이며, 상기 R1, R2, R3, R4 및 R7 중에서 적어도 하나는 [구조식 1]로 표시되는 R8이고,[구조식 1]상기 [구조식 1]에서,n은 1 내지 10의 정수이고, R9는 수소 또는 메틸이다.상기 [화학식 1]에서 a, b 및 c는 각각 독립적으로 0 내지 4의 정수이고, m은 1 내지 10의 정수이다.
- 제1항에 있어서,상기 R5 및 R6은 각각 독립적으로 치환 또는 비치환된 탄소수 1 내지 10의 알콕시기 또는 할로겐인 것을 특징으로 하는 트리아릴메탄 청색 염료 화합물.
- 제1항에 있어서,상기 R1은 R2와, 상기 R3는 R4와 서로 연결되어 포화 또는 불포화 고리를 형성하는 것을 특징으로 하는 트리아릴메탄 청색 염료 화합물.
- 청색 염료 화합물; 바인더 수지; 반응성 불포화 화합물; 중합 개시제; 유기용제; 및 첨가제;를 포함하고,상기 청색 염료 화합물은 제1항에 따른 상기 [화학식 1]로 표시되는 청색 염료 화합물인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 있어서,상기 청색 염료 화합물은 크산텐 염료, 시아닌 염료 및 아자포피린 염료 중에서 선택되는 1종 이상을 더 포함하는 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 있어서,상기 청색 염료 화합물은 청색 수지 조성물 총중량에 대하여 0.01 중량% 내지 50 중량%인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 있어서,상기 청색 수지 조성물은 청색 안료를 더 포함할 수 있고, 상기 청색 안료는 구리프탈로시아닌계 청색 안료인 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 있어서,상기 반응성 불포화 화합물은 열경화성 단량체나 올리고머; 광경화성 단량체나 올리고머; 및 이들의 조합으로 이루어진 군에서 선택되는 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 있어서,상기 중합 개시제는 열중합 개시제, 광중합 개시제 및 이들의 조합으로 이루어진 군에서 선택되는 것을 특징으로 하는 컬러필터용 청색 수지 조성물.
- 제5항에 따른 컬러필터용 청색 수지 조성물을 이용하여 제조된 것을 특징으로 하는 컬러필터.
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JP6166683B2 (ja) * | 2014-03-28 | 2017-07-19 | 富士フイルム株式会社 | 着色硬化性組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 |
JP6318920B2 (ja) * | 2014-07-01 | 2018-05-09 | 三菱ケミカル株式会社 | 着色樹脂組成物、カラーフィルタ、液晶表示装置及び有機el表示装置 |
JP2017090780A (ja) * | 2015-11-13 | 2017-05-25 | 東洋インキScホールディングス株式会社 | カラーフィルタ用着色組成物、およびカラーフィルタ |
KR102475604B1 (ko) * | 2016-08-25 | 2022-12-08 | 동우 화인켐 주식회사 | 착색 감광성 수지 조성물, 이를 이용하여 제조된 컬러필터 및 화상표시장치 |
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KR20140141969A (ko) | 2014-12-11 |
US9340673B1 (en) | 2016-05-17 |
US20160122545A1 (en) | 2016-05-05 |
JP2016527333A (ja) | 2016-09-08 |
KR101563131B1 (ko) | 2015-10-26 |
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