JP2018158962A - Method for producing diketopyrrolopyrrole pigment - Google Patents

Abstract

An object of the present invention is to provide a diketopyrrolopyrrole pigment suitable for the production of a color filter with high brightness and high contrast, a method for producing the same, and an organic solvent for milling and kneading. In the step of grinding and kneading a mixture comprising a diketopyrrolopyrrole pigment, a water-soluble inorganic salt and an organic solvent, the organic solvent satisfies the following (i) to (iii): This is solved by a method for producing ketopyrrolopyrrole pigments. (I) The flash point is 40 ° C. or higher. (Ii) Does not contain a hydroxyl group. (Iii) having at least one functional group selected from amide, sulfone, sulfoxide, ketone, ester, and two or more ether bonds. [Selection figure] None

Description

  The present invention relates to a color liquid crystal display device and a manufacturing method for a color filter used for manufacturing a color filter used for a color imaging device and the like. Furthermore, the present invention relates to a color filter coloring composition containing the pigment, and a color filter formed using the same.

  Generally, in a color liquid crystal display device, a transparent electrode for driving a liquid crystal is formed on a color filter by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon. Yes. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, a high temperature treatment of generally 200 ° C. or higher, preferably 230 ° C. or higher is required in the production process for forming the color filter. Therefore, at present, a method called a pigment dispersion method using a pigment having excellent light resistance and heat resistance as a colorant is mainly used for color filters.

  In the pigment dispersion method, it is common to use a pigment having excellent light resistance and heat resistance, such as a diketopyrrolopyrrole pigment, an anthraquinone pigment, a perylene pigment, and a disazo pigment, alone or in combination as a colorant in the red filter segment. It is.

  Among the diketopyrrolopyrrole pigments, C.I. I. Pigment Red 254 is well known as a colorant for red color filters. In recent years, brominated diketopyrrolopyrrole pigments, which are bromine analogs, have been disclosed in C.I. I. It has been reported that brightness higher than that of Pigment Red 254 is given (for example, Patent Document 1 and Patent Document 2).

  In order to increase the brightness and the contrast of color filters, a pigmentation process (also referred to as a conditioning or finishing process) is required to reduce the primary particle size of the diketopyrrolopyrrole pigment and adjust the crystal shape. . As the pigmentation step, a salt milling process in which a pigment is ground and kneaded by adding a water-soluble inorganic salt and a water-soluble organic solvent is widely used. In Patent Document 2 to Patent Document 4, a brominated diketopyrrolopyrrole pigment is subjected to a salt milling treatment, thereby finishing it in a preferable usage form as a color material for a color filter. However, the market demand for brightness improvement in recent years is remarkable, and further improvement in brightness and contrast is required.

JP 2011-523433 A JP 2012-155232 A JP 2006-180042 A International Publication No. 2015/083352

  An object of the present invention is to provide a diketopyrrolopyrrole pigment suitable for producing a color filter having high brightness and high contrast, a method for producing the same, and an organic solvent for milling and kneading.

  As a result of intensive studies, the present inventors have surprisingly found that the problems of the present invention can be solved in the following embodiments produced using an organic solvent satisfying all of (i) to (iii), The present invention has been completed.

That is, the present invention provides a diketopyrrolopyrrole in which the organic solvent satisfies the following (i) to (iii) in a step of grinding and kneading a mixture comprising a diketopyrrolopyrrole pigment, a water-soluble inorganic salt and an organic solvent. The present invention relates to a method for producing a pyrrole pigment.
(I) The flash point is 40 ° C. or higher.
(Ii) Does not contain a hydroxyl group.
(Iii) having at least one functional group selected from amide, sulfone, sulfoxide, ketone, ester, and two or more ether bonds.

  In the present invention, the organic solvent may be N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, sulfolane, dimethyl sulfoxide, glycol diether solvent, glycol diester solvent, and glycol. The present invention relates to a method for producing the diketopyrrolopyrrole pigment, which is at least one selected from ether ester solvents.

  The present invention also relates to a method for producing the diketopyrrolopyrrole pigment, wherein the diketopyrrolopyrrole pigment is a brominated diketopyrrolopyrrole pigment.

  Moreover, this invention relates to the coloring composition for color filters containing the diketopyrrolopyrrole pigment obtained by the said manufacturing method, binder resin, and the organic solvent.

  The present invention further relates to the coloring composition for a color filter further containing at least one selected from a photopolymerizable monomer and a photopolymerization initiator.

  Moreover, this invention relates to the color filter which comprises the filter segment formed from the said coloring composition for color filters.

  ADVANTAGE OF THE INVENTION According to this invention, the diketopyrrolopyrrole pigment suitable for manufacture of a high brightness and a high contrast color filter, its manufacturing method, and the organic solvent for grinding kneading | mixing can be provided.

  Hereinafter, the present invention will be described in detail. Note that “CI” described below means a color index (CI).

<Production method of diketopyrrolopyrrole pigment>
The grinding kneading of the present invention refers to a mixture obtained by adding at least a water-soluble inorganic salt and an organic solvent to a pigment, kneader, two roll mill, three roll mill, ball mill, attritor, horizontal sand mill, vertical sand mill or / And a so-called salt milling process in which a water-soluble inorganic salt and an organic solvent are washed and removed after mechanically kneading while heating using a kneader such as an annular bead mill. The water-soluble inorganic salt works as a grinding aid, and it is considered that the pigment is crushed using the high hardness of the water-soluble inorganic salt during salt milling, thereby generating an active surface and causing crystal growth. ing. Accordingly, since the crushing of the pigment and the crystal growth occur simultaneously during the kneading, the kneading conditions and the like can be appropriately adjusted according to the type of the pigment and the required degree of fineness.

  The heating temperature for the salt milling treatment is preferably 35 to 150 ° C. When the heating temperature is less than 35 ° C., crystal growth does not occur sufficiently, and the shape of the pigment particles becomes nearly amorphous, which is not preferable. On the other hand, when the heating temperature exceeds 150 ° C., crystal growth proceeds excessively and the primary particle diameter of the pigment becomes large, which may not be preferable as a color filter colorant. 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 salt milling treatment pigment and the cost required for the salt milling treatment.

  By optimizing the conditions for salt milling the pigment, a pigment having a very fine primary particle diameter, a narrow distribution width, and a sharp particle size distribution can be obtained.

  The diketopyrrolopyrrole pigment of the present invention is a pigment having a 1,4-diketopyrrolo [3,4-c] pyrrole-1,4-dione skeleton as a chromophore. I. Pigment red 254, 255, 264, 272, C.I. I. Pigment Orange 71, 73, 81, brominated diketopyrrolopyrrole pigment, and the like, but are not limited thereto. Examples of diketopyrrolopyrrole pigments having chromaticity suitable for color filters include C.I. I. Pigment Red 254 and a brominated diketopyrrolopyrrole pigment, more preferably a brominated diketopyrrolopyrrole pigment.

  As the water-soluble inorganic salt used in the salt milling treatment, sodium 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, more preferably 300 to 1200% by mass, based on the total amount of the pigment composition (100% by mass) from the viewpoint of both processing efficiency and production efficiency.

<Organic solvent for grinding and kneading>
The organic solvent used for the salt milling process must function to wet the pigment and the water-soluble inorganic salt, and should not substantially dissolve the water-soluble inorganic salt used. Furthermore, the organic solvent in the present invention satisfies the following (i) to (iii). That is,
(I) The flash point is 40 ° C. or higher.
(Ii) Does not contain a hydroxyl group.
(Iii) having at least one functional group selected from amide, sulfone, sulfoxide, ketone, ester, and two or more ether bonds.
It satisfies all the conditions. The organic solvent satisfying these (i) to (iii) (hereinafter also referred to as the organic solvent of the present invention) may be used alone or in combination of two or more. The organic solvent of the present invention is suitable as a solvent for milling and kneading, but a solvent other than the organic solvent of the present invention (including an organic solvent not satisfying any one or more of the above (i) to (iii)). The combined use is not excluded without departing from the scope of the present invention. However, it is preferable to use the organic solvent of the present invention substantially from the viewpoint of high brightness and high contrast. Hereinafter, the organic solvent of the present invention will be described.

  The flash point in (i) is the value of the flash point measured by a method according to the quick equilibrium sealing method defined in JIS standard K2265-2: 2007. From the viewpoint of safety during salt milling, the flash point needs to be 40 ° C or higher. In order to further improve safety, it is preferable to select an organic solvent having a flash point higher than the heating temperature of the salt milling treatment.

As specified in (ii) and (iii), the organic solvent does not contain a hydroxyl group in its molecule and is at least one selected from amides, sulfones, sulfoxides, ketones, esters, and two or more ether bonds. It has a functional group.
The organic solvents that satisfy (i), (ii), and (iii) are specifically listed below.
As a solvent having an amide, formamide, N-methylformamide, N, N-dimethylformamide, N, N-dimethylacetamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, ε-caprolactam, 1,3-dimethyl-2 -Imidazolidinone,
As a solvent having a sulfone, sulfolane, 3-methyl sulfolane, ethyl methyl sulfone, ethyl isopropyl sulfone, dimethyl sulfone, propane sultone,
As a solvent having sulfoxide, dimethyl sulfoxide,
As a solvent having a ketone, diisobutyl ketone, cyclohexanone, di-n-propyl ketone, methyl-n-hexyl ketone, diisopropylideneacetone, 1,5,5-trimethyl-3-cyclohexenone,
Examples of the solvent having an ester include benzyl formate, 2-ethylhexyl acetate, benzyl acetate, 2-ethylhexyl acetate, cyclohexyl acetate, methyl benzoate, ethyl benzoate, butyl benzoate, γ-butyrolactone, diethyl oxalate, dibutyl oxalate, Dipentyl oxalate, diethyl malonate, dimethyl malonate, dimethyl maleate, diethyl maleate, dibutyl maleate, dibutyl sebacate, dimethyl phthalate, diethyl phthalate, dibutyl phthalate, dioctyl phthalate, triacetin, diethyl adipate, Dioctyl adipate, triethyl acetyl citrate, tributyl acetyl citrate, allyl acetoacetate, ethyl acetoacetate, methyl acetoacetate, isoamyl propionate, butyl butyrate,
Examples of the solvent having an ester further include glycol diester solvents and glycol ether ester solvents. For example, ethylene glycol diacetate, diethylene glycol diacetate, 2-butoxyethyl acetate, 2-phenoxyethyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono Butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, 3-methoxy-3-methylbutyl acetate, 3-methoxybutyl acetate, ethyl 3-ethoxypropionate,

Examples of the solvent having two or more ether bonds include glycol diether solvents. Examples thereof include ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, diethylene glycol ethyl methyl ether, triethylene glycol dimethyl ether, and dipropylene glycol dimethyl ether.

From the viewpoint of brightness and contrast, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, sulfolane, dimethyl sulfoxide, glycol diether solvent, glycol diester solvent, and glycol ether ester solvent Is preferred. Among glycol diether solvents, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, and diethylene glycol dibutyl ether are more preferable. Among glycol diester solvents, ethylene glycol diacetate is more preferable. Among glycol ether ester solvents, ethylene glycol is used. Monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monoethyl ether acetate, and propylene glycol monomethyl ether acetate are more preferable.
Although the usage-amount of the organic solvent of this invention is not specifically limited, It is preferable to use 5-1000 mass parts with respect to 100 mass parts of pigments, and it is more preferable to use 50-500 mass parts. One kind or a plurality of kinds of organic solvents may be used in combination.

  By using an organic solvent having such a specific structure, it is possible to provide a diketopyrrolopyrrole pigment suitable for producing a color filter with high brightness and high contrast. The reason is not speculative, but organic solvents with functional groups that are less polar and less hydrogen-bonding than hydroxyl groups give better results in interaction with diketopyrrolopyrrole pigments. Think.

  The method for removing the water-soluble inorganic salt and the organic solvent used for the salt milling treatment is not particularly limited as long as it does not affect the pigment particles, and examples thereof include water washing and removal by filtration. At this time, the organic solvent of the present invention may be washed and removed using a water-soluble organic solvent such as methanol or acetone as long as it does not affect the pigment particles.

  The method for removing water from the water-containing cake of the diketopyrrolopyrrole pigment from which the water-soluble inorganic salt and organic solvent have been removed is not particularly limited, and examples thereof include atmospheric pressure drying, reduced pressure drying, freeze drying, and spray drying treatment. . The pigment may be pulverized simultaneously with the drying process or after the drying process.

<Additives>
When performing the salt milling treatment, additives such as a pigment derivative and a dispersant may be further included for the purpose of improving kneading efficiency and dispersibility. Examples of the dispersant include a resin and / or a low molecular weight surfactant.

  As a pigment derivative used as a dispersant, a compound having an organic pigment as a basic skeleton and having introduced a substituent imparting acidity or a substituent imparting basicity into the molecule is suitable. By adding an organic pigment derivative, it is considered that the pigment is adsorbed by the pigment to be dispersed and imparts polarity, thereby giving a dispersion effect from the interaction with the dispersant and the resin. In addition, an effect contributing to pigment crystal stabilization and dispersion stabilization can be expected. In order to exhibit the effect of suppressing crystal growth, it is required that the dye derivative is efficiently adsorbed on the surface of the diketopyrrolopyrrole pigment and is not easily desorbed. For this reason, the structure of the pigment derivative is often considered to have a partial chemical structure similar to the pigment used. For these reasons, when producing a diketopyrrolopyrrole pigment, a dye derivative having a diketopyrrolopyrrole structure, a thiazineindigo structure, a benzoisoindole structure, or a quinacridone structure is generally effective. is there.

  Moreover, when using a pigment derivative, it is required not to impair the color tone of the diketopyrrolopyrrole pigment as much as possible. From the viewpoint of hue, it is preferable to use a diketopyrrolopyrrole derivative, a benzoisoindole derivative, a thiazineindigo derivative, an azo dye derivative, or a quinophthalone derivative that exhibits yellow, orange, and red.

  The blending amount of the pigment derivative is preferably in the range of 0.5 to 40% by mass based on the total amount of the pigment composition (100% by mass). More preferably, it is the range of 3-35 mass%. When the amount is 0.5% by mass or less, the crystal growth suppressing effect is not sufficient, and when it is 40% by mass or more, the good color tone of the diketopyrrolopyrrole pigment is impaired.

  The type of resin used as the dispersant is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified with natural resins, and the like can be used. This resin is solid at room temperature, preferably insoluble in water, and more preferably soluble in the organic solvent of the present invention. It is preferable that the usage-amount of resin is the range of 5-100 mass parts with respect to 100 mass parts of pigments. One of the advantages of using the organic solvent of the present invention in carrying out the resin treatment is that the resin is dissolved. By using the organic solvent of the present invention, the resin can be uniformly coated on the pigment, and even when the pigment is dried, the coating resin suppresses aggregation of the pigments and contributes to improvement in dispersibility. I believe that.

  As preferable examples of the resin used as the dispersant, polyurethane, polyester, unsaturated polyamide, phosphate ester, polycarboxylic acid and its amine salt / ammonium salt / alkylamine salt, polycarboxylic acid ester, hydroxyl group-containing polycarboxylic acid ester, Oil-soluble dispersants such as polysiloxane and modified polyacrylate, water-soluble such as (meth) acrylic acid- (meth) acrylic acid ester copolymer, (meth) acrylic acid-styrene copolymer, styrene-maleic acid copolymer Examples include resins and water-soluble polymer compounds. Resin-type dispersants can be used alone or in admixture of two or more. The resin type dispersant preferably has a mass average molecular weight of about 1,000 to 30,000.

  Suitable examples of the surfactant used as the dispersant include naphthalene sulfonic acid formalin condensate salt, aromatic sulfonic acid formalin condensate, anionic surfactant such as polyoxyethylene alkyl phosphate ester, polyoxyethylene alkyl ether and the like. Nonionic activators, cation activators such as alkylamine salts, quaternary ammonium salts and the like.

  The diketopyrrolopyrrole pigment of the present invention can be used as a colored composition when used in combination with a binder resin and an organic solvent. Moreover, you may use together colorants other than the diketopyrrolopyrrole pigment of this invention.

<Other colorants>
The coloring composition of the present invention may be used in combination with other colorants such as pigments and dyes other than the diketopyrrolopyrrole pigment of the present invention in order to adjust the chromaticity. Specific examples of other colorants are shown below.

  For example, 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, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, Mention may be made of red pigments such as 279, 280, 281, 282, 283, 284, 285, 286 or 287. Examples of red dyes include xanthene series, azo series (pyridone series, barbituric acid series, metal complex series, etc.), disazo series, and anthraquinone series. Specifically, C.I. I. And salt forming compounds of xanthene acid dyes such as Acid Red 52, 87, 92, 289 and 338.

  In addition, 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.

  Preferred colorants to be used in combination are C.I. I. Pigment red 177, 254, 242, C.I. I. Pigment yellow 139, 150, and 185.

  When a colorant other than the diketopyrrolopyrrole pigment is used in combination, the diketopyrrolopyrrole pigment composition of the present invention is preferably in the range of 40% by mass to 100% by mass in the total amount of the colorant (100% by mass). . More preferably, it is the range of 60 mass%-100 mass%.

<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 the alkali-soluble resin include an acrylic resin having an acidic group, an α-olefin / (anhydrous) maleic acid copolymer, a styrene / styrene sulfonic acid copolymer, an ethylene / (meth) acrylic acid copolymer, or Examples include isobutylene / (anhydrous) maleic acid copolymer. 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, aldehyde 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 said thermoplastic resin consists of a polymer of a monomer, and the following are mentioned as the said monomer to comprise. 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 (Meth) acrylates such as tylene glycol (meth) acrylate, or (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, dye (Meth) acrylamides such as acetone (meth) acrylamide or acryloylmorpholine, styrenes such as styrene or α-methylstyrene, ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether Examples thereof include vinyl ethers, vinyl acetate, and fatty acid vinyls such as vinyl propionate.

  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.

  Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins. 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) are connected to 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 the company 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 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 developing solution is poor and it is difficult to form a fine pattern. When it exceeds 300 mgKOH / g, a fine pattern does not remain by development.

  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 colored composition of the present invention, the pigment is sufficiently dispersed in a pigment carrier, and applied to a glass substrate or the like so as to have a dry film thickness of 0.2 to 5 μm to form a filter segment. In order to facilitate, 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 of 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 monoethyl It is preferable to use glycol acetates such as 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. Moreover, since the organic solvent can adjust the coloring composition to an appropriate viscosity and can form a filter segment with a desired uniform film thickness, the total mass of the colorant is based on 100 mass%, and is 500 to 4000 mass. % Is preferably used.

<Pigment dispersion>
The coloring composition of the present invention comprises a diketopyrrolopyrrole pigment of the present invention in a colorant carrier composed of the binder resin and an organic solvent, a kneader, a two-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical type. It can be produced by finely dispersing using various dispersing means such as a sand mill, an annular bead mill, or an attritor. In addition, the coloring composition of the present invention may be obtained by simultaneously dispersing the diketopyrrolopyrrole pigment of the present invention and other colorants in a colorant carrier, or by separately mixing those dispersed in a colorant carrier. Also good.

  Further, when the colorant is dispersed in the colorant carrier, a dispersion aid such as the above-described dye derivative, resin-type dispersant, surfactant, or the like may be appropriately contained. Since the dispersion aid has a great effect of preventing re-aggregation of the colorant after dispersion, the color composition obtained by dispersing the colorant in the colorant carrier using the dispersion aid has contrast and viscosity stability. Become good.

<Resin type dispersant and surfactant>
The resin-type dispersant has a pigment-affinity part having a property of adsorbing to the colorant and a part compatible with the colorant carrier, and adsorbs to the colorant to disperse the colorant to the colorant carrier. It works to stabilize. Specific examples of resin-type dispersants 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 alkylamine salts. , Polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester, modified products thereof, amides formed by reaction of poly (lower alkyleneimine) and polyester having a free carboxyl group, and salts thereof Oil-soluble dispersants such as, (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone, etc. Resin, water-soluble polymer, polyester, modified poly Acrylate-based, 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., BASF EFKA-46, 47, 48, 452, 4008, 4009, 4010, 4015, 4020, 4047, 4050, 4055, 4060, 4080, 4400, 4401, 4402, 4403, 4406, 4408, 4300, 4310, 4320 , 4330, 4340, 450, 451, 453, 4540, 4550, 4560, 4800, 5010, 5065, 5066, 5070, 7500, 7554 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, sodium alkyl diphenyl ether disulfonate Anionic surfactants such as lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate; Polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene Nonionic surfactants such as alkyl ether phosphates, polyoxyethylene sorbitan monostearate and polyethylene glycol monolaurate; chaotic surfactants such as alkyl quaternary ammonium salts and their ethylene oxide adducts; alkyldimethylamino Examples include amphoteric surfactants such as alkylbetaines such as betaine acetate and alkylimidazolines, and these can be used alone or in admixture of two or more, but are not necessarily limited thereto.

  In the case of adding a resin-type dispersant and a surfactant, the total amount of the colorant is based on (100% by mass), preferably 0.1 to 55% by mass, more preferably 0.1 to 45% 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.

  The colored composition of the present invention can be used as a photosensitive colored composition by further adding a photopolymerizable monomer and / or a photopolymerization initiator.

<Photopolymerizable monomer>
Photopolymerizable monomers that may be used in the photosensitive coloring composition include monomers or oligomers that are cured by ultraviolet rays or heat to produce a transparent resin, which are used alone or in combination of two or more. Can be used. The amount of the monomer is preferably 5 to 400% by weight based on the total weight of the colorant (100% by weight), and more preferably 10 to 300% by weight from the viewpoint of photocurability and developability. preferable.

  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>
In the photosensitive coloring composition, when the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, a photopolymerization initiator is added in the form of a solvent development type or alkali development type colored resist material. Can be adjusted.

  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 photosensitive coloring composition (100% by mass), and 3 to 3 from the viewpoint of photocurability and developability. More preferably, it is 150 mass%.

<Sensitizer>
Furthermore, the photosensitive coloring composition 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) benzopheno And 4,4′-diethylaminobenzophenone.

  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 (100% by mass) of the photopolymerization initiator contained in the photosensitive coloring composition, and is photocured. Is more preferably 5 to 50% by mass from the viewpoint of the property and developability.

<Amine compound>
In addition, the coloring composition or the photosensitive coloring composition can contain an amine compound that functions to reduce 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 or the photosensitive coloring composition. 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>
In order to assist the curing of the thermosetting resin, the coloring composition or the photosensitive coloring composition may contain a curing agent, a curing accelerator, and the like as necessary. 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 or the photosensitive coloring composition may 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 is 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 colored composition or photosensitive coloring composition (100% by mass). be able to.

<Removal of coarse particles>
The coloring composition and the photosensitive coloring composition are 5 μm or more coarse particles, preferably 1 μm or more coarse particles, more preferably 0.5 μm or more by means of centrifugation, filtration with a sintered filter or a membrane filter, or the like. It is preferable to remove coarse particles 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 of the present invention will be described. The color filter of the present invention comprises a red filter segment, a green filter segment, and a blue filter segment, and the red filter segment therein contains the diketopyrrolopyrrole pigment composition of the present invention. Or it forms from the photosensitive coloring composition.

  The green filter segment can be formed using a conventional green coloring composition comprising a green pigment and a colorant carrier. Examples of the green pigment include C.I. I. Pigment Green 7, 10, 36, 37, 58, etc. are used.

  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, 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, Mention may be made of yellow pigments such as 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220, or 221. Further, a basic dye exhibiting yellow and a salt-forming compound of an acid dye can be used in combination.

  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, or the like in addition to the above method, but the coloring composition or the photosensitive coloring composition 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.

  Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In Examples and Comparative Examples, “parts” and “%” mean “parts by mass” and “% by mass”.

<Production of diketopyrrolopyrrole crude pigment>
[Production Example 1] (Production of Brominated Diketopyrrolopyrrole Crude Pigment Represented by Formula (1))
To a stainless steel reaction vessel equipped with a reflux tube, 200 parts of tert-amyl alcohol dehydrated with molecular sieves and 140 parts of sodium-tert-amyl alkoxide are added in a nitrogen atmosphere and heated to 100 ° C. with stirring to obtain an alcoholate solution. Prepared. On the other hand, 88 parts of diisopropyl succinate and 153.6 parts of 4-bromobenzonitrile were added to a glass flask and dissolved by heating to 90 ° C. with stirring to prepare a solution of these mixtures. The heated solution of the mixture was slowly dropped into the alcoholate solution heated to 100 ° C. at a constant rate over 2 hours with vigorous stirring. After completion of the dropwise addition, heating and stirring were continued for 2 hours at 90 ° C. to obtain an alkali metal salt of a diketopyrrolopyrrole compound. Furthermore, 600 parts of methanol, 600 parts of water and 304 parts of acetic acid were added to a reaction vessel with a glass jacket, and cooled to -10 ° C. While cooling this mixture with a high-speed stirring disperser and rotating a shear disk having a diameter of 8 cm at 4000 rpm, the alkali metal salt of the diketopyrrolopyrrole compound obtained above was cooled to 75 ° C. The solution was added in small portions. At this time, the rate of addition of the alkali metal salt of the diketopyrrolopyrrole compound at 75 ° C. while cooling so that the temperature of the mixture consisting of methanol, acetic acid and water is always kept at −5 ° C. or lower. Was added in small portions over approximately 120 minutes. After addition of the alkali metal salt, red crystals were precipitated to form a red suspension. Subsequently, the obtained red suspension was washed with an ultrafiltration device at 5 ° C. and then filtered to obtain a red paste. This paste was re-dispersed in 3500 parts of methanol cooled to 0 ° C. to obtain a suspension with a methanol concentration of about 90%, and stirred at 5 ° C. for 3 hours to perform particle sizing and washing with crystal transition. Subsequently, the resulting diketopyrrolopyrrole compound aqueous paste was separated by filtration using an ultrafiltration machine, dried at 80 ° C. for 24 hours, and pulverized to obtain a brominated diester represented by the formula (1). 150.8 parts of ketopyrrolopyrrole crude pigment was obtained.

[Production Example 2] (Production of CI Pigment Red 254 Crude Pigment Represented by Formula (2))
Except for changing 153.6 parts of 4-bromobenzonitrile to 117.4 parts of 4-chlorobenzonitrile, the same procedure as in Production Example 1 was carried out, and C.I. I. Pigment Red 254 crude pigment 120.7 parts was obtained.

<Production of resin solution>
[Production Example 3] (Preparation of Resin A)
A reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device was charged with 196 parts of cyclohexanone, heated to 80 ° C., and purged with nitrogen in the reaction vessel. From the tube, 37.2 parts of n-butyl methacrylate, 12.9 parts of 2-hydroxyethyl methacrylate, 12.0 parts of methacrylic acid, paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toagosei Co., Ltd.) 20.7 A mixture of 1.1 parts of 2,2′-azobisisobutyronitrile was added dropwise over 2 hours. After completion of the dropping, the reaction was continued for 3 hours to obtain a resin solution. After cooling to room temperature, about 2 parts of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. Propylene glycol monomethyl was added to the previously synthesized resin solution so that the nonvolatile content was 20% by mass. Resin A was prepared by adding ether acetate.

[Production Example 4] (Preparation of Resin B)
In a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device, 57.0 parts of a polycarbodiimide compound having an carbodiimide equivalent of 316 having an isocyanate group, 16.0 parts of methyldiethanolamine Was maintained at about 100 ° C. for 2 hours to react the isocyanate group with the hydroxyl group. Next, after 97.7 parts of propylene glycol monomethyl ether acetate was charged, 178.7 parts of a 12-hydroxystearic acid self-condensate having a carboxyl group at the terminal and having a molecular weight of 1,000 was charged and maintained at about 90 ° C. A carbodiimide group and a carboxyl group were reacted. After cooling to room temperature, about 2 parts of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. Propylene glycol monomethyl was added to the previously synthesized resin solution so that the nonvolatile content was 20% by mass. Ether B was added to prepare Resin B.

[Production Example 5] (Preparation of Resin C)
207 parts of cyclohexanone was charged into a reaction vessel equipped with a separable four-necked flask equipped with a thermometer, a cooling tube, a nitrogen gas introduction tube, a dropping tube and a stirring device, heated to 80 ° C., and the inside of the reaction vessel was purged with nitrogen. From the tube, 20 parts of methacrylic acid, 20 parts of paracumylphenol ethylene oxide modified acrylate (Aronix M110 manufactured by Toagosei Co., Ltd.), 45 parts of methyl methacrylate, 8.5 parts of 2-hydroxyethyl methacrylate, and 2,2′-azobis A mixture of 1.33 parts of isobutyronitrile was added dropwise over 2 hours. After completion of the dropwise addition, the reaction was further continued for 3 hours to obtain a copolymer resin solution. Next, after the nitrogen gas was stopped and stirred while injecting dry air for 1 hour with respect to the total amount of the copolymer solution obtained, the mixture was cooled to room temperature, and then 2-methacryloyloxyethyl isocyanate (Karenz manufactured by Showa Denko KK). MOI) A mixture of 6.5 parts, 0.08 part dibutyltin laurate and 26 parts cyclohexanone was added dropwise at 70 ° C. over 3 hours. After completion of the dropwise addition, the reaction was further continued for 1 hour to obtain a resin solution. After cooling to room temperature, sample 2 parts of the resin solution, heat dry at 180 ° C. for 20 minutes, measure the nonvolatile content, and add cyclohexanone to the previously synthesized resin solution so that the nonvolatile content is 20% by mass. Resin C was prepared.

  Hereinafter, the pigment derivatives used in Examples or Comparative Examples are listed in Table 1.

<Production of diketopyrrolopyrrole pigment>
[Example 1] (Production of diketopyrrolopyrrole pigment (R-1))
100 parts of diketopyrrolopyrrole pigment of the formula (1), 1000 parts of sodium chloride and 120 parts of formamide were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is poured into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed to remove salt and formamide, dried at 80 ° C. overnight, and pulverized As a result, 97.0 parts of a diketopyrrolopyrrole pigment (R-1) was obtained.

[Examples 2 to 25, Comparative Examples 1 to 7] (Production of diketopyrrolopyrrole pigment (R-2 to 32))
A diketopyrrolopyrrole pigment (R-2 to 32) was obtained in the same manner as in Example 1 except that the kneading composition shown in Table 2 was changed. However, the resin solution containing the solvent was used by appropriately replacing with a kneading solvent or used as a solid resin dried at 80 ° C. under reduced pressure. The mass parts of the resin described in Table 2 are mass parts of resin solids.

<Manufacture of coloring composition for color filter>
[Example 26] (Preparation of colored composition (RP-1))
The following mixture was stirred and mixed to be uniform, and then dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then a 5 μm filter. To prepare a colored composition (RP-1).
Diketopyrrolopyrrole pigment (R-1) 11.0 parts Dye derivative a 1.0 part Resin solution A 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts

[Examples 27 to 50, Comparative Examples 8 to 14] (Preparation of colored composition (RP-2 to 32))
A colored composition (RP-2 to 32) was obtained in the same manner as in Example 26 except that the composition was changed to the composition shown in Table 3. Examples 49 and 50 and Comparative Example 14 are coloring compositions to which no dye derivative and resin solution are added, as shown in the table.

<Other pigments, preparation method of coloring composition>
[Production Example 6] (Production of dianthraquinone pigment (PR177-1))
90 parts of a dianthraquinone pigment (CI Pigment Red 177), 900 parts of sodium chloride, and 150 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, the kneaded mixture is put into warm water, stirred for 1 hour while heating to about 80 ° C. to form a slurry, filtered and washed with water to remove salt and diethylene glycol, and then dried at 80 ° C. for one day and pulverized. As a result, 88.0 parts of a dianthraquinone pigment (PR177-1) was obtained.

[Production Example 7] (Preparation of colored composition (RP-33))
The mixture of the composition shown below is uniformly stirred and mixed, dispersed with picomil for 8 hours using zirconia beads having a diameter of 0.1 mm, and then filtered through a 5 μm filter to produce a colored composition (RP-33). did.
Dianthraquinone pigment (PR177-1) 12.0 parts Resin solution A 40.0 parts Propylene glycol monomethyl ether acetate 48.0 parts

<Preparation of photosensitive coloring composition>
[Example 51] (Preparation of photosensitive coloring composition (RR-1))
A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare photosensitive coloring composition 1 (RR-1).
Colored composition (RP-1) 38.4 parts Colored composition (RP-33) 3.6 parts Resin solution C 13.2 parts Photopolymerizable monomer ("Aronix M400" manufactured by Toagosei Co., Ltd.) 2.8 Part Photopolymerization initiator ("Irgacure 907" manufactured by BASF) 2.0 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 part Ethylene glycol monomethyl ether acetate 39.6 parts

[Examples 52 to 75, Comparative Examples 15 to 21] (Preparation of photosensitive coloring composition (RR-2 to 32))
The coloring composition (RP-1) is changed to the coloring composition (RP-2 to 32), and further the coloring composition (RP-2 to 32) and the coloring composition so as to have the same chromaticity as Example 51 A photosensitive colored composition (RR-2 to 32) was produced in the same manner as in Example 51 except that the ratio of (RP-33) was adjusted.

<Evaluation of photosensitive coloring composition>
The following evaluation was performed about the obtained photosensitive coloring composition (RR-1 to 32). The evaluation results are shown in Table 4.

(Color characteristic evaluation)
The obtained photosensitive coloring composition was applied on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 0.7 mm so that x = 0.640 and y = 0.328 in a C light source, and dried. Then, ultraviolet rays of 300 mJ / cm ² were irradiated using an ultra high pressure mercury lamp. Furthermore, the red coating film was obtained by heating at 230 degreeC for 60 minutes. Then, the brightness (Y) of the obtained coating film was measured with a microspectrophotometer (“OSP-SP200” manufactured by Olympus Optical Co., Ltd.).

(Evaluation of contrast ratio of coating film)
The obtained photosensitive coloring composition was applied on a 100 mm × 100 mm, 0.7 mm thick glass substrate to a thickness such that x = 0.640 using a C light source, and dried. Furthermore, the red coating film was obtained by heating at 230 degreeC for 60 minutes. About the obtained red coating film, the contrast was measured by the following method.

A method for measuring the contrast ratio of the coating film will be described. The light emitted from the backlight unit for liquid crystal display passes through the polarizing plate, is polarized, passes through the dry coating film of the photosensitive coloring composition applied on the glass substrate, and reaches the polarizing plate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, light is transmitted through the polarizing plate, but if the polarizing plane is perpendicular, the light is blocked by the polarizing plate. However, when light polarized by the polarizing plate passes through the dried coating film of the photosensitive coloring composition, scattering by pigment particles occurs, and when a part of the polarization plane is displaced, the polarizing plate is parallel. The amount of light transmitted through the polarizing plate is reduced, and when the polarizing plate is perpendicular, a part of the light is transmitted through the polarizing plate. This transmitted light was measured as the luminance on the polarizing plate, and the ratio (contrast ratio) between the luminance when the polarizing plate was parallel and the luminance when it was orthogonal was calculated.
(Contrast ratio) = (Luminance when parallel) / (Luminance when direct)
Accordingly, when scattering occurs due to the pigment in the coating film, the brightness when parallel is reduced and the brightness when perpendicular is increased, the contrast ratio is lowered. A color luminance meter ("BM-5A" manufactured by Topcon Corporation) was used as the luminance meter, and a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko Corporation) was used as the polarizing plate. In the measurement, a black mask with a 1 cm square hole was applied to the measurement portion in order to block unnecessary light.

  From the results shown in Table 4, it was found that the examples using the diketopyrrolopyrrole pigment obtained by the production method of the present invention were excellent in brightness and contrast ratio in forming color filters.

<Color filter manufacturing method>
[Production Example 8] (Preparation of green photosensitive coloring composition 1 (GR-1))
A mixture having the composition shown below is stirred and mixed uniformly, and dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then a 5 μm filter. To produce a green colored composition 1 (GP-1).
Green pigment (CI Pigment Green 36) 6.8 parts Yellow pigment (CI Pigment Yellow 150) 5.2 parts Resin type dispersant ("EFKA4300" manufactured by BASF) 1.0 part Resin solution A 35 0.0 part propylene glycol monomethyl ether acetate 52.0 parts

A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare green photosensitive coloring composition 1 (GR-1).
Green coloring composition 1 (GP-1) 42.0 parts Resin solution C 13.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator (manufactured by BASF “ Irgacure 907 ") 2.0 parts Sensitizer (" EAB-F "manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 39.6 parts

[Production Example 9] (Preparation of blue photosensitive coloring composition 1 (BR-1))
A mixture having the composition shown below is stirred and mixed uniformly, and dispersed with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) for 5 hours using zirconia beads having a diameter of 0.5 mm, and then a 5 μm filter. And blue colored composition 1 (BP-1) was produced.
Blue pigment (CI Pigment Blue 15: 6) 7.2 parts Purple Pigment (CI Pigment Violet 23) 4.8 parts Resin type dispersant ("EFKA4300" manufactured by BASF) 1.0 part Resin solution A 35.0 parts Propylene glycol monomethyl ether acetate 52.0 parts

A mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to prepare a blue photosensitive coloring composition 1 (BR-1).
Blue coloring composition 1 (BP-1) 34.0 parts Resin solution C 15.2 parts Photopolymerizable monomer (“Aronix M400” manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator (manufactured by BASF “ Irgacure 907 ") 2.0 parts Sensitizer (" EAB-F "manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Ethylene glycol monomethyl ether acetate 45.1 parts

(Production of color filter)
A black matrix is patterned on a glass substrate, and the photosensitive coloring composition (RR-14) of the present invention is formed on the substrate with a spin coater so that x = 0.640 and y = 0.328. It was applied to form a colored film. The coating was irradiated with 300 mJ / cm ² of ultraviolet rays through a photomask using an ultrahigh pressure mercury lamp. Next, spray development was performed with an alkaline developer composed of a 0.2% by weight sodium carbonate aqueous solution to remove the unexposed portion, and the substrate was washed with ion-exchanged water, and the substrate was heated at 230 ° C. for 20 minutes to obtain a red filter. A segment was formed. In the same manner, the green photosensitive coloring composition 1 (GR-1) was formed to a thickness such that x = 0.300 and y = 0.600, and the blue photosensitive coloring composition 1 (BR-1) was added. The film was applied to a thickness of x = 0.150 and y = 0.060, respectively, to form a green filter segment and a blue filter segment to obtain a color filter.

  By using the photosensitive coloring composition (RR-14) of the present invention, it was possible to produce a color filter excellent in brightness and contrast.

Claims (6)

A method for producing a diketopyrrolopyrrole pigment, wherein the organic solvent satisfies the following (i) to (iii) in a step of grinding and kneading a mixture comprising a diketopyrrolopyrrole pigment, a water-soluble inorganic salt and an organic solvent.
(I) The flash point is 40 ° C. or higher.
(Ii) Does not contain a hydroxyl group.
(Iii) having at least one functional group selected from amide, sulfone, sulfoxide, ketone, ester, and two or more ether bonds.   The organic solvent is N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, sulfolane, dimethyl sulfoxide, glycol diether solvent, glycol diester solvent, and glycol ether ester solvent. The method for producing a diketopyrrolopyrrole pigment according to claim 1, which is at least one selected.   The method for producing a diketopyrrolopyrrole pigment according to claim 1 or 2, wherein the diketopyrrolopyrrole pigment is a brominated diketopyrrolopyrrole pigment.   The coloring composition for color filters containing the diketopyrrolopyrrole pigment obtained by the manufacturing method as described in any one of Claims 1-3, binder resin, and the organic solvent.   Furthermore, the coloring composition for color filters of Claim 4 containing at least one selected from a photopolymerizable monomer and a photoinitiator. The color filter which comprises the filter segment formed from the coloring composition for color filters of Claim 4 or 5.