JP2012193318A - Method for producing pigment composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a pigment composition free from lowering of the contrast ratio even when a color filter formation process is carries out at high temperature; and to provide a method for producing the same.SOLUTION: This method for producing the pigment composition comprises mechanically kneading a dispersant expressed by formula, an organic pigment and a water-soluble inorganic salt together with a water-soluble organic solvent substantially not dissolving the water-soluble inorganic salt, where in formula, n is an integer of 1-5; R1 represents hydrogen or an alkyl group which may have a substituent; R2 to R4 each independently represent an alkyl group which may have a substituent.

Description

  The present invention relates to a method for producing a pigment composition capable of providing a high-quality color filter without reducing the contrast ratio after post-baking.

  A color filter is a surface of a transparent substrate such as glass, in which two or more kinds of fine band (striped) filter segments of different hues are arranged in parallel or intersecting, or fine filter segments are arranged vertically and horizontally. It is made up of those arranged in The filter segment is as fine as several microns to several hundred microns, and it is necessary to perform the color filter formation step in a predetermined arrangement for each hue at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher.

  For this reason, heat resistance is also required as a coloring composition required for a color filter, particularly as a pigment. Even if the contrast ratio of the glass substrate coated with the coloring composition is high, the contrast ratio is lowered by applying heat.

  Therefore, in the production of the filter segment, a coloring composition containing a dispersant is used. I. Pigment Yellow 138 (hereinafter referred to as PY138) is free of sulfonated products, or salts formed with sulfonated products of PY138, which is a salt formed by neutralization with a metal alkali aqueous solution or an amine aqueous solution (for example, patents). References 1, 2 and 3).

JP 2002-179799 A JP 2003-167112 A Japanese Patent No. 4585781

    An object of the present invention is to provide a pigment composition in which the contrast ratio does not decrease even when the color filter forming step is performed at a high temperature, and a method for producing the same.

  The present invention mechanically kneads PY138 and a dispersant represented by the following general formula 1 together with a water-soluble inorganic salt and a water-soluble organic solvent that does not substantially dissolve the water-soluble inorganic salt. The present invention relates to a method for producing a pigment composition.

General formula 1

(In General Formula 1, n is an integer of 1 to 5, R1 is hydrogen or an alkyl group that may have a substituent, and R2 to R4 each independently represents an alkyl group that may have a substituent. .)
Moreover, this invention relates to the manufacturing method of the said pigment composition whose at least one of R1-R4 is a C8-C30 alkyl group.

  Further, after kneading PY138, the dispersant represented by the general formula 1, the water-soluble inorganic salt and the water-soluble solvent at 20 to 60 ° C., the water-soluble inorganic salt and the water-soluble solvent are removed by washing with water. The present invention relates to a method for producing the above pigment composition.

  Moreover, it is related with the pigment composition manufactured by the said manufacturing method.

  According to the present invention, it was possible to provide a pigment composition that maintains a high contrast ratio without lowering the contrast ratio even after the substrate coated with the coloring composition is heat-treated.

  The dispersant represented by the general formula 1 used in the present invention is a salt formed with a sulfonated product of PY138 and a product having an amino group or an ammonium ion and serving as a cation counter.

  First, a method for producing a salted product of a sulfonated product of PY138 used as an anion portion will be described. For example, it is manufactured by the following method.

  PY138 is added with concentrated sulfuric acid, fuming sulfuric acid, chlorosulfonic acid, or a mixture thereof to carry out the sulfonation reaction. The reaction solution is dropped into a large amount of water or ice water, filtered and washed with water to obtain a paste. The paste is redispersed in water, an aqueous solution of various amines or quaternary ammonium salt compounds is added dropwise, and the resulting suspension is filtered, washed with water and dried.

  A preferred form of a product having an amino group or an ammonium ion and serving as a counter as a cation is a tertiary amine or quaternary ammonium salt compound having at least one long-chain alkyl group having 8 to 30 carbon atoms. .

  Specific examples of the tertiary amine include dimethyloctylamine (carbon number 8), dimethyldecylamine (carbon number 10), dimethyllaurylamine (carbon number 12), dimethylmyristylamine (carbon number 14), dimethyl palmitylamine ( It is preferable to use carbon number 16), dimethylstearylamine (carbon number 18), dimethylbehenylamine (carbon number 22), dilauryl monomethylamine, trioctylamine and the like.

  Specific examples of tertiary amines include Farmin DM24C, Farmin DM0898, Farmin DM1098, Farmin DM2098, Farmin DM4098, Farmin DM6098, Farmin DM8680, Farmin DM2285, and Farmin M2-2095 manufactured by Kao Corporation.

  Specific examples of the quaternary ammonium salt compound include monolauryl trimethyl ammonium chloride, dilauryl dimethyl ammonium chloride, trilauryl monomethyl ammonium chloride, monostearyl trimethyl ammonium chloride, distearyl dimethyl ammonium chloride, tristearyl monomethyl ammonium chloride, monocetyl trimethyl. Ammonium chloride (16 carbon atoms), dicetyldimethylammonium chloride, tricetylmonomethylammonium chloride, monostearyltrimethylammonium chloride, distearyldimethylammonium chloride, tristearylmonomethylammonium chloride, monobehenyltrimethylammonium chloride, dibehenyldimethylan Chloride, tri behenyl monomethyl ammonium chloride, it is preferable to use an alkyl benzyl dimethyl ammonium chloride and the like.

  Specific examples of quaternary ammonium chloride products include Cotamin 24P, Cotamin 86P Conch, Cotamin 60W, Cotamin 86W, Cotamin D86P, Sanizole C, Sanizole B-50 manufactured by Kao Corporation.

  As a use ratio of the pigment and the dispersant represented by the general formula 1, 1 to 80 parts by mass of the dispersant represented by the general formula 1 is used with respect to 100 parts of the pigment in any coloring composition. it can. Moreover, it is most preferable to use 1-20 mass% preferably in the range of 0.5-40 mass%.

  As the water-soluble inorganic salt used in the present invention, sodium chloride, potassium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of cost. The water-soluble inorganic salt is preferably used in an amount of 50 to 2000% by mass, and most preferably 300 to 1200% by mass, based on the total amount of the pigment composition (100% by mass) in terms of both processing efficiency and production efficiency.

  The water-soluble organic solvent used in the present invention functions to wet the pigment composition and the water-soluble inorganic salt, dissolves (mixes) in water, and does not substantially dissolve the water-soluble inorganic salt used. If it is a thing, it will not specifically limit. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during the salt milling process and these solvents are easily evaporated.

  Examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by weight, more preferably 50 to 500 parts by weight, based on 100 parts by weight of the pigment composition.

  Salt milling treatment is preferred as the method for producing the pigment composition of the present invention. Salt milling is a process of heating and cooling a mixture of a pigment composition, a water-soluble inorganic salt, and a water-soluble organic solvent using a kneader such as a kneader, two-roll mill, three-roll mill, ball mill, attritor, or sand mill. Then, after mechanically kneading, the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. A kneader having a high grinding effect (manufactured by Inoue Seisakusho Co., Ltd.) is desirable as the kneader. The water-soluble inorganic salt works as a crushing aid, and it is considered that the pigment composition is crushed using the high hardness of the inorganic salt during salt milling, resulting in an active surface and crystal growth. It has been. Therefore, the crushing and crystal growth of the pigment composition occur simultaneously during kneading, and the primary particle size of the pigment composition obtained varies depending on the kneading conditions.

  The internal temperature of the kneader can be operated at 20 to 150 ° C., but the internal temperature is preferably 20 to 60 ° C. from the viewpoint of fine primary particles. When the heating temperature exceeds 60 ° C., crystal growth proceeds excessively and the primary particle diameter of the pigment composition becomes large, which is not preferable as a colorant for a color filter. The kneading time for the salt milling treatment is preferably 2 to 24 hours from the viewpoint of the balance between the particle size distribution of the primary particles of the pigment composition subjected to the salt milling treatment and the cost required for the salt milling treatment.

  By optimizing the conditions for salt milling the pigment composition, it is possible to obtain a pigment composition having a sharp particle size distribution in which the primary particle size is very fine and the distribution range is wide.

  In the salt milling treatment, the above-mentioned dye derivative may be used in combination for improving the kneading efficiency, which is very effective for making the pigment composition finer and sized. The amount of the pigment derivative used is preferably an amount that does not affect the color tone, that is, a range of 0.5 to 40% by mass with respect to 100% by mass of the pigment composition.

  Moreover, when performing a salt milling process, you may add resin as needed. The type of resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. The resin used is solid at room temperature, preferably insoluble in water, and more preferably partially soluble in the organic solvent. It is preferable that the usage-amount of resin is the range of 5-200 mass parts with respect to 100 mass parts of pigment compositions.

  The pigment composition of the present invention can be used as a colored composition by forming a composition together with a binder resin and an organic solvent. In that case, you may use together colorants other than the pigment composition of this invention. Examples of the colorant include various pigments or dyes or dye salt forming compounds.

  When the color filter coloring composition produced using the pigment composition of the present invention is used as a red coloring composition, a red pigment can be added. Examples of the red pigment to be added include C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 122, 146, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 242, 246, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, Mention may be made of red pigments such as 280, 281, 282, 283, 284, 285, 286 or 287. Other red dyes that can be used in the colorant include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, anthraquinone series, and the like. Specifically, C.I. I. And salt forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338. Among them, C.I. I. It is preferable to use one or more selected from among CI Pigment Red 177, 242, and 254.

  The red coloring composition includes C.I. I. Pigment Orange 43, 71, or 73, and / or C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181 182,185,187,188,193,194,198,199,213,214,218,219,220, or a yellow pigment 221 and the like can be used in combination. Examples of the orange dye and / or yellow dye include quinoline series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and methine series. Among them, C.I. Pigment orange 43, 71 orange pigments, C.I. I. It is preferable to use one or more selected from yellow pigments of CI Pigment Yellow 138, 139, 150, and 185.

  Moreover, when using the coloring composition for color filters manufactured using the pigment composition of this invention as a green coloring composition, a green pigment can be added. Examples of the green pigment to be added include C.I. I. Pigment Green 2, 7, 10, 36, 37, 58, etc. are used. Among them, C.I. I. It is preferable to use one or more selected from among CI Pigment Green 7, 36, and 58.

  A yellow pigment can be used in combination with the green coloring composition. Examples of yellow pigments that can be used in combination include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 18 , Mention may be made of the 187,188,193,194,198,199,213,214,218,219,220,221 and the like. Further, a basic dye exhibiting yellow and a salt-forming compound of an acid dye can be used in combination. Among them, C.I. I. It is preferable to use one or more selected from CI Pigment Yellow 138, 139, 150, and 185.

(Binder resin)
Examples of the binder resin contained in the colored composition of the present invention include conventionally known thermoplastic resins and thermosetting resins.

  Examples of the thermoplastic resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane resin. Polyester resins, vinyl resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like.

  When used as a coloring composition for a color filter, the spectral transmittance is preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Moreover, when using with the form of an alkali image development type colored resist, it is preferable to use the alkali-soluble vinyl resin which copolymerized the acidic group containing ethylenically unsaturated monomer. In order to further improve the photosensitivity, an energy ray curable resin having an ethylenically unsaturated active double bond can also be used.

  Examples of the alkali-soluble resin obtained by copolymerizing an acidic group-containing ethylenically unsaturated monomer include resins having an acidic group such as a carboxyl group or a sulfone group. Specific examples of these alkali-soluble resins include acrylic resins having acidic groups, α-olefin / (anhydrous) maleic acid copolymers, styrene / styrene sulfonic acid copolymers, and ethylene / (meth) acrylic acid copolymers. Examples thereof include a polymer, an isobutylene / (anhydrous) maleic acid copolymer, and the like. Among these, at least one resin selected from an acrylic resin having an acidic group and a styrene / styrene sulfonic acid copolymer, particularly an acrylic resin having an acidic group, is preferably used because of its high heat resistance and transparency.

  Energy ray curable resins having ethylenically unsaturated active double bonds include reactive substitution of isocyanate groups, formyl groups, epoxy groups, etc. on polymers having reactive substituents such as hydroxyl groups, carboxyl groups, amino groups, etc. A resin in which a photo-crosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the polymer by reacting a (meth) acrylic compound having a group or cinnamic acid is used. In addition, polymers containing acid anhydrides such as styrene-maleic anhydride copolymer and α-olefin-maleic anhydride copolymer are half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. A modified version is also used.

  A thermoplastic resin having both alkali-soluble performance and energy ray curing performance is also preferable as the photosensitive coloring composition for color filters.

The following are mentioned as a monomer which comprises the said thermoplastic resin. For example, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (meth) Acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypoly Ji glycol (meth) acrylate of (meth) acrylates,
Alternatively, (meth) acrylamide (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, acryloylmorpholine, etc. Acrylamides, styrenes, styrenes such as α-methylstyrene, vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, isobutyl vinyl ether, fatty acid vinyls such as vinyl acetate or vinyl propionate Kind.

  Alternatively, cyclohexylmaleimide, phenylmaleimide, methylmaleimide, ethylmaleimide, 1,2-bismaleimide ethane 1,6-bismaleimidehexane, 3-maleimidopropionic acid, 6,7-methylenedioxy-4-methyl-3-maleimide Coumarin, 4,4′-bismaleimide diphenylmethane, bis (3-ethyl-5-methyl-4-maleimidophenyl) methane, N, N′-1,3-phenylenedimaleimide, N, N′-1,4- Phenylene dimaleimide, N- (1-pyrenyl) maleimide, N- (2,4,6-trichlorophenyl) maleimide, N- (4-aminophenyl) maleimide, N- (4-nitrophenyl) maleimide, N-benzyl Maleimide, N-bromomethyl-2,3-dichloromaleimide, N-sc N-imidyl-3-maleimidobenzoate, N-succinimidyl-3-maleimidopropionate, N-succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidohexanoate, N- [4- (2-benzimidazolyl) phenyl N-substituted maleimides such as maleimide and 9-maleimide acridine.

  On the other hand, examples of the thermosetting resin include epoxy resin, benzoguanamine resin, rosin-modified maleic acid resin, rosin-modified fumaric acid resin, melamine resin, urea resin, and phenol resin. Especially, an epoxy resin and a melamine resin are used more suitably from a viewpoint of heat resistance improvement.

  The weight average molecular weight (Mw) of the binder resin is preferably in the range of 5,000 to 80,000, more preferably in the range of 7,000 to 50,000 in order to disperse the colorant preferably. The number average molecular weight (Mn) is preferably in the range of 2,500 to 40,000, and the value of Mw / Mn is preferably 10 or less.

  Here, the weight average molecular weight (Mw) and the number average molecular weight (Mn) were determined by connecting four separation columns in series in the gel permeation chromatography “HLC-8120GPC” manufactured by Tosoh Corporation. This is a polystyrene-equivalent molecular weight measured using “TSK-GEL SUPER H5000”, “H4000”, “H3000”, and “H2000” manufactured by Corporation and using tetrahydrofuran as the mobile phase.

  When the binder resin is used as a coloring composition for a color filter, an aliphatic group and an aromatic group which act as an affinity group for a pigment adsorbing group and an alkali-soluble group during development, a pigment carrier and a solvent. The balance is important for pigment dispersibility, developability, and durability, and it is preferable to use a binder resin having an acid value of 20 to 300 mgKOH / g. When the acid value is less than 20 mgKOH / g, the solubility in the developer is poor, and it is difficult to form a fine pattern. On the contrary, if the acid value exceeds 300 mgKOH / g, a fine pattern does not remain by development, which is not preferable.

  The binder resin can be used in an amount of 20 to 500% by mass based on the total mass of the colorant. If it is less than 20% by mass, the film formability and various resistances are insufficient, and if it exceeds 500% by mass, the pigment concentration is low and color characteristics cannot be expressed.

(Organic solvent)
In the coloring composition of the present invention, the pigment composition is sufficiently dispersed in a pigment carrier and applied on a substrate such as a glass substrate so as to have a dry film thickness of 0.2 to 5 μm to form a filter segment. In order to facilitate this, an organic solvent is included. The organic solvent is selected in consideration of good applicability of the coloring composition, solubility of each component of the coloring composition, and safety.

  Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane. 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 3- Methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone, m-xylene, m-diethylbenzene, m-dichlorobenzene, N, N-dimethylacetamide, N, N- Dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, o-xylene, o-chlorotoluene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary butyl ether, Ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, ethylene glycol Monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate , Diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether , Dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol Monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, Louis Seo ketone, methyl cyclohexanol, acetic acid n- amyl acetate n- butyl, isoamyl acetate, isobutyl acetate, propyl acetate, and dibasic acid esters.

  Among them, since the solubility of each component in the coloring composition and the coating property of the coloring composition are good, ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol It is preferable to use glycol acetates such as monoethyl ether acetate, aromatic alcohols such as benzyl alcohol, and ketones such as cyclohexanone.

  These organic solvents can be used individually by 1 type or in mixture of 2 or more types. In addition, the organic solvent adjusts the colored composition to an appropriate viscosity and forms a filter segment having a desired uniform film thickness, with the total mass of the colorant as a reference (100% by mass). It is preferably used in an amount of 4000% by mass.

(Dispersion of pigment composition)
Further, the color filter coloring composition produced by using the pigment composition of the present invention includes a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal type in a colorant carrier composed of the binder resin and an organic solvent. It can be produced by finely dispersing using various dispersing means such as a sand mill, a vertical sand mill, an annular bead mill, or an attritor. Further, the color filter coloring composition produced using the pigment composition of the present invention may be prepared by dispersing the quinophthalone pigment composition and other colorants simultaneously in the colorant carrier, or separately. What was dispersed in the colorant carrier may be mixed.

  Further, when dispersing the colorant in the colorant carrier, a dispersion aid such as a pigment derivative, a resin-type dispersant, and a surfactant may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has a contrast and viscosity stability. Improvement can be expected.

(Resin type dispersant and surfactant)
The resin-type dispersant has a pigment affinity part having a property of adsorbing to the pigment composition and a part compatible with the pigment composition carrier, and adsorbs to the pigment composition to disperse in the coloring composition. It works to stabilize. Specific examples of the resin-type dispersant include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkyls. Amine salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkylene imines) and polyesters having free carboxyl groups, Oil-based dispersants such as salts thereof, (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone, etc. Water-soluble resin, water-soluble polymer compound, polyester, modified Li acrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more, not necessarily limited thereto.

  Commercially available resin-type dispersants include Disperbyk-101, 103, 107, 108, 110, 111, 116, 130, 140, 154, 161, 162, 163, 164, 165, 166, and 170 manufactured by Big Chemie Japan. 171, 174, 180, 181, 182, 183, 184, 185, 190, 2000, 2001, 2020, 2025, 2050, 2070, 2095, 2150, 2155, or Anti-Terra-U, 203, 204, or BYK -SOLPERSE-3000, 9000, 13000, 13240, 13650, 13940, 160 manufactured by Nippon Lubrizol Corporation, such as P104, P104S, 220S, 6919, or Lactimon, Lactimon-WS or Bykumen, etc. 0, 17000, 18000, 20000, 21000, 24000, 26000, 27000, 28000, 31845, 32000, 32500, 32550, 33500, 32600, 34750, 35100, 36600, 38500, 41000, 41090, 53095, 55000, 76500, etc. -EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, manufactured by Japan 4320, 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7 54,1101,120,150,1501,1502,1503, etc., Ajinomoto Fine-Techno Co., Ltd. of AJISPER PA111, PB711, PB821, PB822, PB824, and the like.

  Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfone. Anionic surface activity such as sodium lauryl sulfate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Agents: polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxye Nonionic surfactants such as lenalkyl ether phosphates, polyoxyethylene sorbitan monostearate, and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethyl Examples include amphoteric surfactants such as alkylbetaines such as aminoacetic acid betaine and alkylimidazolines, and these can be used alone or in admixture of two or more, but are not necessarily limited thereto.

  When adding a resin-type dispersant and a surfactant, the total amount of the colorant is preferably 0.1 to 55% by mass, more preferably 0.1 to 45% by mass, based on the total amount (100% by mass). . When the blending amount of the resin-type dispersant and the surfactant is less than 0.1% by mass, it is difficult to obtain the added effect. When the blending amount is more than 55% by mass, the dispersion is affected by an excessive dispersant. May affect.

  Furthermore, the coloring composition for color filters manufactured using the pigment composition of the present invention can be used as a coloring composition by further adding a photopolymerizable monomer and / or a photopolymerization initiator.

(Photopolymerizable monomer)
Furthermore, the photopolymerizable monomer used in the color composition for a color filter produced using the pigment composition of the present invention includes a monomer or oligomer that is cured by ultraviolet rays or heat to produce a transparent resin. These may be used alone or in combination of two or more. The blending amount of the monomer is preferably 5 to 400% by weight based on the total weight of the colored composition (100% by weight), and preferably 10 to 300% by weight from the viewpoint of photocurability and developability. More preferred.

  Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a transparent resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate. , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycy Luether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopentyl glycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, tricyclodeca Nyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate ester, epoxy (meth) acrylate, urethane acrylate and other acrylic esters and methacrylate esters, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl Examples include, but are not necessarily limited to, til (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.

(Photopolymerization initiator)
Further, the color filter coloring composition produced using the pigment composition of the present invention is cured by ultraviolet irradiation and a photopolymerization initiator is added when a filter segment is formed by a photolithographic method. By using a colored composition, it can be adjusted in the form of a solvent development type or alkali development type colored resist material.

  Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as dimethyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, or 3,3 ', 4 Benzophenone compounds such as 4,4'-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, 2,4-diethylthioxanthone, etc. 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxy) Phenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro) Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4-trichloromethyl- Triazine compounds such as (4′-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime) )], Or oxime ester compounds such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6- Phosphine compounds such as trimethylbenzoyl) phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole A imidazole compound; a titanocene compound, or the like.

  These photopolymerization initiators can be used alone or in combination of two or more at any ratio as required. These photopolymerization initiators are preferably 2 to 200% by mass based on the total amount of the colorant in the coloring composition (100% by mass), and 3 to 150% by mass from the viewpoint of photocurability and developability. % Is more preferable.

(Sensitizer)
Furthermore, the coloring composition for color filters produced using the pigment composition of the present invention can contain a sensitizer.

  Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', or 4,4'-tetra (t-butylperoxycarbonyl) benzophen Enone, 4,4'-diethylaminobenzophenone, and the like.

  More specifically, edited by Shin Okawara et al., “Dye Handbook” (1986, Kodansha), edited by Shin Okawara et al., “Chemistry of Functional Dye” (1981, CMC), edited by Tadasaburo Ikemori et al. Examples include, but are not limited to, sensitizers described in "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.

  Two or more kinds of sensitizers may be used in any ratio as required. The blending amount when using the sensitizer is preferably 3 to 60% by mass based on the total weight of the photopolymerization initiator contained in the colored composition (100% by mass), and is photocurable. From the viewpoint of developability, it is more preferably 5 to 50% by mass.

(Amine compounds)
Moreover, the coloring composition for color filters manufactured using the pigment composition of this invention can be made to contain the amine compound which has a function which reduces the dissolved oxygen.

  Such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminobenzoate. Examples include ethyl, 2-ethylhexyl 4-dimethylaminobenzoate, and N, N-dimethylparatoluidine.

(Leveling agent)
In order to improve the leveling property of the composition on the transparent substrate, it is preferable to add a leveling agent to the coloring composition for a color filter produced using the pigment composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferable. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning, BYK-333 manufactured by Big Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK Chemie. Dimethylsiloxane having a polyether structure in the main chain and dimethylsiloxane having a polyester structure in the main chain can be used in combination. The content of the leveling agent is usually preferably 0.003 to 0.5% by mass based on the total weight of the colored composition or the photosensitive colored composition (100% by mass).

  Particularly preferred as a leveling agent is a kind of so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, having a hydrophilic group but low solubility in water, and when added to a coloring composition, It has the characteristics of low surface tension reduction ability, and it is useful to have good wettability to the glass plate despite its low surface tension reduction ability. Those that can sufficiently suppress the chargeability can be preferably used. As a leveling agent having such preferable characteristics, dimethylpolysiloxane having a polyalkylene oxide unit can be preferably used. Examples of the polyalkylene oxide unit include a polyethylene oxide unit and a polypropylene oxide unit, and dimethylpolysiloxane may have both a polyethylene oxide unit and a polypropylene oxide unit.

  In addition, the bonding form of the polyalkylene oxide unit with dimethylpolysiloxane includes a pendant type in which the polyalkylene oxide unit is bonded in the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the end of dimethylpolysiloxane is bonded, and dimethylpolysiloxane. Any of linear block copolymer types in which they are alternately and repeatedly bonded may be used. Dimethylpolysiloxane having a polyalkylene oxide unit is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, FZ. -2207, but is not limited thereto.

  An anionic, cationic, nonionic or amphoteric surfactant can be supplementarily added to the leveling agent. Two or more kinds of surfactants may be mixed and used. Anionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, alkyl diphenyl ether disulfonic acid Sodium, lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Examples include esters.

  Examples of the chaotic surfactant that is supplementarily added to the leveling agent include alkyl quaternary ammonium salts and their ethylene oxide adducts. Nonionic surfactants added to the leveling agent as auxiliary agents include polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate And amphoteric surfactants such as alkyl dimethylamino acetic acid betaine and alkylimidazolines, and fluorine-based and silicone-based surfactants.

(Curing agent, curing accelerator)
The coloring composition for a color filter produced using the pigment composition of the present invention may contain a curing agent, a curing accelerator and the like as necessary in order to assist the curing of the thermosetting resin. . As the curing agent, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds and the like are effective, but are not particularly limited to these, and thermosetting resins. Any curing agent may be used as long as it can react with the. Among these, a compound having two or more phenolic hydroxyl groups in one molecule and an amine curing agent are preferable. Examples of the curing accelerator include amine compounds (for example, dicyandiamide, benzyldimethylamine, 4- (dimethylamino) -N, N-dimethylbenzylamine, 4-methoxy-N, N-dimethylbenzylamine, 4-methyl). -N, N-dimethylbenzylamine etc.), quaternary ammonium salt compounds (eg triethylbenzylammonium chloride etc.), blocked isocyanate compounds (eg dimethylamine etc.), imidazole derivative bicyclic amidine compounds and salts thereof (eg Imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyanoethyl-2-phenylimidazole, 1- (2-cyanoethyl) -2- Til-4-methylimidazole, etc.), phosphorus compounds (eg, triphenylphosphine, etc.), guanamine compounds (eg, melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (eg, 2,4-diamino-6) -Methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine isocyanuric acid adduct, 2,4-diamino-6 Methacryloyloxyethyl-S-triazine / isocyanuric acid adduct, etc.) can be used. These may be used alone or in combination of two or more. As content of the said hardening accelerator, 0.01-15 mass% is preferable with respect to thermosetting resin whole quantity (100 mass%).

(Other additive components)
The coloring composition for a color filter produced using the pigment composition of the present invention can contain a storage stabilizer in order to stabilize the viscosity with time. Moreover, in order to improve adhesiveness with a transparent substrate, adhesion improving agents, such as a silane coupling agent, can also be contained.

  Examples of storage stabilizers include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and methyl ethers thereof, t-butylpyrocatechol, tetraethylphosphine, and tetraphenylphosphine. Organic phosphines, phosphites and the like can be mentioned. The storage stabilizer can be used in an amount of 0.1 to 10% by mass based on the total amount of the colorant (100% by mass).

  Examples of the adhesion improver include vinyl silanes such as vinyltris (β-methoxyethoxy) silane, vinylethoxysilane and vinyltrimethoxysilane, (meth) acrylsilanes such as γ-methacryloxypropyltrimethoxysilane, β- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, β- (3,4-epoxycyclohexyl) methyltrimethoxysilane, β- (3,4-epoxycyclohexyl) ethyltriethoxysilane, β- (3,4-epoxycyclohexyl) Epoxysilanes such as methyltriethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropyltriethoxysilane, N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (amino Ethyl) γ-aminopropyltrie Xisilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, N-phenyl Examples include silane coupling agents such as aminosilanes such as -γ-aminopropyltriethoxysilane, and thiosilanes such as γ-mercaptopropyltrimethoxysilane and γ-mercaptopropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10% by mass, preferably 0.05 to 5% by mass, based on the total amount of the colorant in the coloring composition (100% by mass).

(Removal of coarse particles)
The coloring composition for a color filter produced by using the pigment composition of the present invention has a coarse particle of 5 μm or more, preferably a coarse particle of 1 μm or more, by means such as centrifugation, filtration with a sintered filter or a membrane filter. More preferably, it is preferable to remove coarse particles of 0.5 μm or more and mixed dust. Thus, it is preferable that a coloring composition does not contain a particle | grain of 0.5 micrometer or more substantially. More preferably, it is 0.3 μm or less.

(Color filter)
Next, the color filter manufactured using the pigment composition of this invention is demonstrated. The color filter includes a red filter segment, a green filter segment, and a blue filter segment, and is formed from a coloring composition containing a quinophthalone pigment composition in the red filter segment and the green filter segment therein.

  The blue filter segment can be formed using a normal blue coloring composition containing a blue pigment and a colorant carrier. Examples of blue pigments include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, etc. are used. A purple pigment can be used in combination with the blue coloring composition. Examples of purple pigments that can be used in combination include C.I. I. And violet pigments such as CI Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, and 50. In addition, a basic dye or a salt-forming compound of an acid dye exhibiting blue or purple can be used. When using a dye, a xanthene dye is preferable in terms of heat resistance and lightness.

(Color filter manufacturing method)
The color filter of the present invention can be produced by a printing method or a photolithography method.

  The formation of the filter segment by the printing method can be patterned simply by repeating the printing and drying of the coloring composition prepared as the printing ink. Therefore, the color filter manufacturing method is low in cost and excellent in mass productivity. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.

  When the filter segment is formed by photolithography, the colored composition prepared as a solvent developing type or alkali developing type colored resist material is applied on a transparent substrate by spray coating, spin coating, slit coating, roll coating or the like. By a method, it applies so that a dry film thickness may be set to 0.2-5 micrometers. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or alkali developer or spraying the developer by spraying or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
In order to increase the UV exposure sensitivity, after coating and drying the colored resist, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.

  The color filter of the present invention can be produced by an electrodeposition method, a transfer method, etc. in addition to the above method, but the colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. . The transfer method is a method in which a filter segment is formed in advance on the surface of a peelable transfer base sheet, and this filter segment is transferred to a desired substrate.

  A black matrix can be formed in advance before forming each color filter segment on a transparent substrate or a reflective substrate. As the black matrix, a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto. Further, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then each color filter segment may be formed. In addition, an overcoat film, a transparent conductive film, or the like is formed on the color filter of the present invention as necessary.

  EXAMPLES The present invention will be described in more detail with reference to the following examples. However, the following examples do not limit the scope of rights of the present invention. In the examples, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.

[Example 1]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
Quinophthalone yellow pigment C.I. I. 30 parts of Pigment Yellow 138 (manufactured by BASF <Pariol Yellow K0961-HD>) was dissolved in 214 parts of 98% sulfuric acid and 236 parts of 25% fuming sulfuric acid and stirred at 85 ° C. for 2 hours to carry out the sulfonation reaction. It was. Then, this reaction solution was dropped into 3000 parts of ice water, and the precipitated sulfonated PY138 was separated and washed with water to obtain a paste.

  The obtained paste of sulfonated PY138 was redispersed in 4000 parts of water. Next, the solution was adjusted to pH 10.5 to 10.6 with an aqueous sodium hydroxide solution and dissolved. Coatamine 24P (manufactured by Kao Corporation) was gradually added to this solution to cause a reaction. In order to confirm the end point of the reaction, it can be judged that the salt-forming dispersant was obtained as the end point when the reaction solution was dropped onto the filter paper and the bleeding disappeared. This precipitate was filtered, washed with water, dried and pulverized to obtain a dispersant (Y-1) formed by salt formation with a sulfonated product of PY138.

[Example of pigmentation]
15 parts of the dispersant (Y-1) obtained above and a quinophthalone yellow pigment C.I. I. Pigment Yellow 138 (manufactured by BASF <Pariotor Yellow K0961-HD>) and 1500 parts of dried sodium chloride were placed in a 3 L kneader (manufactured by Inoue Seisakusho). The internal temperature was controlled at 60 ° C. with a heating medium, 330 parts of diethylene glycol was added, and after forming a good dough state, kneading was started. After kneading for 10 hours, the mixture was added to 10 times the weight of water and stirred to dissolve sodium chloride and diethylene glycol, followed by filtration and washing with water to separate the pigment. The wet cake containing water was heat treated at 80 ° C. for 24 hours, dried to a moisture content of less than 1% by weight, and then pulverized through a 150 mesh wire mesh to obtain a pigment composition (YD-1).

[Example 2]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
The same procedure as in [Synthesis Example] in [Example 1] except that Cotamine 24P in [Synthesis Example] in [Example 1] was changed to Cotamin 60W (manufactured by Kao Corporation), and a dispersant (Y-2) was prepared. Obtained.

[Example of pigmentation]
A pigment was produced in the same manner as in [Pigmentation Example] in [Example 1] except that the dispersant (Y-1) in [Pigmentation Example] in [Example 1] was changed to the dispersant (Y-2). A composition (YD-2) was obtained.

[Example 3]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
The same procedure as in [Synthesis Example] in [Example 1] except that Cotamine 24P in [Synthesis Example] in [Example 1] was changed to Cotamine D86P (manufactured by Kao Corporation), and dispersant (Y-3) was prepared. Obtained.

[Example of pigmentation]
A pigment was produced in the same manner as in [Pigmentation Example] in [Example 1] except that the dispersant (Y-1) in [Pigmentation Example] in [Example 1] was changed to the dispersant (Y-3). A composition (YD-3) was obtained.

[Example 4]
[Example of pigmentation]
A pigment composition (YD-) was prepared in the same manner as [Pigmentation Example] in [Example 1] except that the internal temperature of [Pigmentation Example] in [Example 1] was changed from 60 ° C. to 20 ° C. dispersant. 4) was obtained.

[Example 5]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
The same procedure as in [Synthesis Example] in [Example 1] except that Cotamine 24P in [Synthesis Example] in [Example 1] was changed to Farmin DM2098 (manufactured by Kao Corporation), and dispersant (Y-4) was prepared. Obtained.

[Example of pigmentation]
A pigment was produced in the same manner as [Pigmentation Example] in [Example 1] except that the dispersant (Y-1) in [Pigmentation Example] in [Example 1] was changed to the dispersant (Y-4). A composition (YD-5) was obtained.

[Comparative Example 1]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
It was produced in the same manner as in [Synthesis Example] in [Example 1], up to a paste of PY138 sulfonated product.

  The obtained paste of sulfonated PY138 was redispersed in 4000 parts of water. Next, the solution was adjusted to pH 10.5 to 10.6 with an aqueous ammonia solution and dissolved. To this solution, ammonium chloride was gradually added to react. In order to confirm the end point of the reaction, it can be judged that the salt-forming dispersant was obtained as the end point when the reaction solution was dropped onto the filter paper and the bleeding disappeared. This precipitate was filtered, washed with water, dried and pulverized to obtain a dispersant (Y-5) formed by salt formation with a sulfonated product of PY138.

[Example of pigmentation]
A pigment was produced in the same manner as [Pigmentation Example] in [Example 1] except that the dispersant (Y-1) in [Pigmentation example] in [Example 1] was changed to the dispersant (Y-5). A composition (YD-6) was obtained.

[Comparative Example 2]
[Synthesis Example] (Method for producing dispersant formed by salt formation with sulfonated product of PY138)
The same procedure as in [Synthesis Example] in [Example 1] except that the aqueous solution of Cotamine 24P in [Synthesis Example] in [Example 1] was changed to a 10% acetamine 24 (manufactured by Kao Corporation) aqueous solution. 6) was obtained.

[Example of pigmentation]
A pigment was prepared in the same manner as in [Pigmentation Example] in [Example 1] except that the dispersant (Y-1) in [Pigmentation example] in [Example 1] was changed to the dispersant (Y-6). A composition (YD-7) was obtained.

[Comparative Example 3]
[Example of pigmentation]
Quinophthalone yellow pigment C.I. I. 150 parts of Pigment Yellow 138 (manufactured by BASF <Pariotor Yellow K0961-HD>) and 1500 parts of dried sodium chloride were placed in a 3 L kneader (manufactured by Inoue Seisakusho). The internal temperature was controlled at 60 ° C. with a heating medium, 330 parts of diethylene glycol was added, and after forming a good dough state, kneading was started. After kneading for 10 hours, the mixture was added to 10 times by weight of water and stirred to dissolve sodium chloride and diethylene glycol, followed by filtration and purification to separate the pigment. The wet composition containing water is heat-treated at 80 ° C. for 24 hours, dried to a moisture content of less than 1% by weight, and the pigment compositions obtained so far are listed in Table 1.

(Evaluation of color filter characteristics of pigment compositions obtained in Examples and Comparative Examples)
For the pigment compositions obtained in Examples and Comparative Examples, chromaticity and contrast ratio were measured. These evaluations initially produced a colored composition. The colored composition is applied to a glass substrate using a spin coater and heated. The chromaticity and contrast ratio of the subsequent coated substrate were measured. The evaluation method is described.

(Preparation of coloring composition 1)
The pigment compositions obtained in Examples 1 to 5 and Comparative Examples 1 and 2 were mixed with a resin type pigment dispersant, an acrylic resin for evaluation, and an organic solvent in the following composition, and a planetary ball mill (manufactured by Freche Japan) In a planetary ball mill P-5), 290 g of zirconia beads having a diameter of 0.5 mm was used and dispersed at 320 rpm for 4 hours to prepare colored compositions (YP-1 to 7).

(Mixed component) (Quantity)
10.8 g of pigment compositions obtained in Examples 1 to 5 and Comparative Examples 1 and 2
1.2 g of sulfonated aluminum salt of PY138
19% 30% Addisper PB821
/ Methoxypropyl acetate (PGMAc)
Acrylic resin for evaluation (solid content 30%) 19g
PGMAc 70g

(Method of synthesizing aluminum salt of sulfonated product of PY138)
[Synthesis example]
[Example 1] Except for changing from Cotamine 24P in [Synthesis Example] to an aqueous solution of aluminum sulfate (liquid sulfuric acid band), it was produced in the same manner as [Synthesis Example] in [Example 1], and an aluminum salt of a sulfonated product of PY138 Got.

(Coloring composition adjustment 2)
The pigment obtained in Comparative Example 3 was mixed with a resin-type pigment dispersant, an acrylic resin for evaluation, and an organic solvent in the following composition, and in a planetary ball mill (planet type ball mill P-5 manufactured by Freche Japan), A colored composition (YP-8) was prepared by dispersing 290 g of zirconia beads having a diameter of 0.5 mm at 320 rpm for 4 hours.

(Mixed component) (Quantity)
9.72 g of the pigment composition obtained in Comparative Example 3
1.80 g obtained in the synthesis example of Example 1
Salt salt of sulfonated derivative of PY138 Aluminum salt of sulfonated derivative of PY138 1.2 g
19% 30% Addisper PB821
/ Methoxypropyl acetate (PGMAc)
Acrylic resin for evaluation (solid content 30%) 19g
PGMAc 70g

(Coloring composition application and pre-baking treatment)
A colored film was prepared by the following method using the obtained colored composition. That is, the obtained colored composition was applied on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 0.7 mm using a spin coater at a rotation speed so as to sandwich the chromaticity (x) 0.420 of the colored film. Three glass substrates were obtained. This glass substrate was dried at 60 ° C./5 minutes as a pre-bake treatment.
(Evaluation of color filter characteristics of coating film)
The coated and dried glass substrate was measured with a microspectrophotometer ("OSP-SP200" manufactured by Olympus Optical Co., Ltd.) for chromaticity, and a contrast tester ("CT-1BF" manufactured by Aisaka Electric Co., Ltd.) for the contrast ratio. Measured with The contrast ratio for the chromaticity (x) 0.420 of the colored film was calculated by linear approximation from the three measured values.
(Post bake treatment and color filter characteristics evaluation)
The glass substrate after the pre-bake treatment was dried at 230 ° C./40 minutes as a post-bake treatment, and the chromaticity x and the contrast ratio were measured in the same manner as described above and the color filter characteristic evaluation. Further, the contrast ratio with respect to the chromaticity (x) 0.420 of the colored film was calculated by linear approximation from the measured values at three points.

  Table 2 shows the measurement results after the pre-bake treatment and after the post-bake treatment.

  As described in each example, after a glass substrate coated with a pigment composition obtained by kneading PY138 and a dispersant represented by the general formula 1 and a coloring composition using the same was heat-treated However, it can be seen that by maintaining a high contrast ratio without lowering the contrast ratio, it is excellent as a pigment composition for color filters.

Claims (4)

C. I. Pigment Yellow 138 and a dispersant represented by the following general formula 1 are mechanically kneaded together with a water-soluble inorganic salt and a water-soluble organic solvent that does not substantially dissolve the water-soluble inorganic salt. A method for producing a pigment composition.
General formula 1

(In General Formula 1, n is an integer of 1 to 5, R1 is hydrogen or an alkyl group that may have a substituent, and R2 to R4 each independently represents an alkyl group that may have a substituent. .) The method for producing a pigment composition according to claim 1, wherein at least one of R1 to R4 is an alkyl group having 8 to 30 carbon atoms. C. I. Pigment Yellow 138, the dispersant represented by the general formula 1, the water-soluble inorganic salt and the water-soluble organic solvent are kneaded at 20 to 60 ° C., and then the water-soluble inorganic salt and the water-soluble organic solvent are removed by washing with water. A process for producing a pigment composition according to claim 1 or 2. A pigment composition produced by the production method according to claim 1.