JP5856729B2 - Method for producing coloring composition - Google Patents

Description

  The present invention relates to a method for producing a colored composition.

In general, pixels of a color filter used in a liquid crystal display device, a solid-state image sensor, and the like are formed using, for example, a colored composition. Specifically, a coloring composition containing any one of three colors of red, green, and blue is applied onto a substrate using a coating apparatus, and volatile components are removed by heating or the like. Thereafter, exposure is performed through a mask, and then, in the case of the negative type, the unexposed portion is developed and removed with a developer such as an alkaline aqueous solution to form a colored pattern. The obtained colored pattern may be referred to as heat treatment (hereinafter referred to as post-bake).
) To form a pixel. The same operation is performed for the remaining two color pixels, and finally, a color filter having three color pixels of red, green, and blue is formed.
As the coloring composition, those containing a radical polymerizable monomer, a dye, a photopolymerization initiator and the like are usually used.

On the other hand, in recent years, there has been a demand for further high-definition color filters in various applications.
Therefore, a method for suppressing the generation and mixing of fine foreign substances by filtering the colored composition a plurality of times after preparation of the colored composition has been proposed (see Patent Document 1).

JP 2008-58642 A

  An object of this invention is to provide the manufacturing method of the coloring composition which can minimize presence of a micro foreign material.

The method for producing the colored composition of the present invention comprises:
A first step of passing the dye solution (A) through a first filter;
And a second step of passing the mixed solution containing the dye solution (A), the pigment or pigment dispersion (B), and the solvent (C) that has passed through the first filter through the second filter.

In the manufacturing method of this coloring composition,
The ratio of the hole diameter of the first filter to the hole diameter of the second filter is preferably 1: 1.1 to 1: 500.
Moreover, it is preferable that the hole diameter of a 1st filter is 0.01-0.5 micrometer, or the hole diameter of a 2nd filter is 0.5-5.0 micrometers.
The mixed solution is preferably a mixed solution further containing at least one selected from the group consisting of a resin (D), a photopolymerizable compound (E), and a photopolymerization initiator (F).

  According to the manufacturing method of the coloring composition of this invention, presence of a micro foreign material can be minimized. Thereby, in order to obtain a high-definition color filter with a uniform film thickness, it can be advantageously used.

The method for producing a colored composition of the present invention includes a first step of passing a dye solution (A) through a first filter, a dye solution (A) that has passed through the first filter, a pigment or a pigment dispersion (B), and And a second step of passing the liquid mixture containing the solvent (C) through the second filter.
First, in the first step, when the dye solution (A) is prepared, it is passed through a first filter.
Here, the dye solution (A) means a solution in which a solvent-soluble dye is used alone or in combination of two or more thereof and is dissolved in a solvent.

  It does not specifically limit as dye, It can select from a well-known dye etc. as a conventional color filter use. For example, Japanese Patent Application Laid-Open No. 64-90403, Japanese Patent Application Laid-Open No. 64-91102, Japanese Patent Application Laid-Open No. 1-94301, Japanese Patent Application Laid-Open No. 6-11614, No. 2592207, US Pat. No. 4,808,501. Specification, US Pat. No. 5,667,920, US Pat. No. 5,059,500, JP-A-5-333207, JP-A-6-35183, JP-A-6-51115 Among the dyes / pigments described in JP-A-6-194828, solvent-soluble dyes, in particular, acid dyes, basic dyes, direct dyes, sulfur dyes, vat dyes, naphthol dyes, reactive dyes, disperse dyes Etc.

  The chemical structure of the dye includes pyrazole azo, anilino azo, aryl azo, pyrazolo triazole azo, pyridone azo, triphenyl methane, anthraquinone, anthrapyridone, benzylidene, oxonol, cyanine, polymethine, Any of phenothiazine, pyrrolopyrazole azomethine, xanthene, phthalocyanine, quinophthalone, benzopyran, indigo, dioxazine, coumarin, squarylium, and the like may be used. Among them, pyrazole azo series, anilino azo series, pyrazolotriazole azo series, pyridone azo series, anthraquinone series, anthrapyridone series, phthalocyanine series, dioxazine series, quinophthalone series, and xanthene series are exemplified. In particular, pyrazole azo, pyridone azo, phthalocyanine, quinophthalone, xanthene, and the like are preferably used.

As a specific dye, for example,
Acid alizarin violet N;
C. I. Acid black 1, 2, 24, 48 etc .;
C. I. Acid blue 1, 7, 9, 120, 138, 335, 340, etc .;
C. I. Acid Chrome violet K etc .;
Acid Fuchsin;
C. I. Acid green 1, 3, 5, 58, 80, 106, 109 etc .;
C. I. Acid orange 6-8, 62-64, 169, 173 etc .;
C. I. Acid red 1, 4, 8, 50-52, 111, 257, 426, etc .;
C. I. Acid violet 6B, 7, 9, 17, 19 etc .;
C. I. Acid yellow 1, 3, 7, 123, 202-205, 251 etc .;
C. I. Direct Yellow 2, 33-35, 93-95, 141 etc .;
C. I. Direct Orange 34, 39, 41, 97, 106, 107 etc .;
C. I. Direct Red 79, 82-84, 96-99, 220-234 etc .;
C. I. Direct Violet 47, 52, 84, 103, 104 etc .;
C. I. Direct Blue 57, 97-101, 158-164, 275, 293, etc .;
C. I. Direct Green 25, 63, 77, 79, 82 etc .;
C. I. Modern Yellow 5, 8, 33, 50, 62, 65 etc .;
C. I. Modern Orange 3, 36, 47, 48 etc .;
C. I. Modern Red 1-4, 22-26, 63, 71, 88, 95 etc .;
C. I. Modern Violet 2, 4, 30-32, 53, 58 etc .;
C. I. Modern Blue 2, 30, 53, 61, 74, 84 etc .;
C. I. Modern Green 1, 26, 53, etc .;
C. I. Food Yellow 3 etc. and derivatives of these dyes;
C. I. Solvent Blue 44, 38;
C. I. Solvent Orange 45;
Rhodamine B,
Rhodamine 110,
Examples include 3-[(5-chloro-2-phenoxyphenyl) hydrazono] -3,4-dihydro-4-oxo-5-[(phenylsulfonyl) amino] -2,7-naphthalenedisulfonic acid and the like. .

  As the dye, a compound represented by the following formula (1) (sometimes referred to as “dye (1)”) can be used. In particular, the dye (1) has sufficient solubility in the solvent contained in the coloring composition, and also has sufficient solubility in the developer so that the pattern can be formed in the development step during pattern formation.

(In the formula (1), R _{1 to} R ₄ each independently represents a hydrogen atom, —R or an aromatic hydrocarbon group having 6 to 10 carbon atoms. The aromatic hydrocarbon group having 6 to 10 carbon atoms. A hydrogen atom contained in is a halogen atom, —R, —OH, —OR, —SO ₃ ^— , —SO ₃ Na, —CO ₂ H, —CO ₂ R, —SO ₃ H, —SO ₃ R or — It may be substituted with SO ₂ NHR ₈ .
R ₅ represents —SO ₃ ^— , —SO ₃ Na, —CO ₂ H, —CO ₂ R, —SO ₃ H or —SO ₂ NHR ₈ . m represents an integer of 0 to 5. When m is an integer of 2 or more, the plurality of R ₅ may be the same or different.
R represents each independently a saturated hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom or an alkoxy-substituted saturated hydrocarbon group having 1 to 10 carbon atoms which may be substituted with a halogen atom. Represent.
R ₈ represents a hydrogen atom, —R, —CO ₂ R, or an aromatic hydrocarbon group having 6 to 10 carbon atoms, and the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms is —R Alternatively, it may be substituted with -OR.
X represents a halogen atom. a represents an integer of 0 or 1. )

Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms include phenyl and naphthyl.
Examples of the halogen atom include fluorine, chlorine, bromine and iodine.

As —CO ₂ R, a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonyl group, a pentyloxycarbonyl group, an isopentyloxycarbonyl group, a neopentyloxycarbonyl group , Cyclopentyloxycarbonyl group, hexyloxycarbonyl group, cyclohexyloxycarbonyl group, heptyloxycarbonyl group, cycloheptyloxycarbonyl group, octyloxycarbonyl group, 2-ethylhexyloxycarbonyl group, cyclooctyloxycarbonyl group, nonyloxycarbonyl group, Decanyloxycarbonyl group, tricyclodecanyloxycarbonyl group, methoxypropyloxycarbonyl group, ethoxypropyloxy Aryloxycarbonyl group, a hexyloxy propyloxy group, 2-ethylhexyloxy propyloxy carbonyl group, such as methoxy hexyloxycarbonyl group.

Examples of —SO ₃ R include a methoxysulfonyl group, an ethoxysulfonyl group, a hexyloxysulfonyl group, and a decanyloxysulfonyl group.
—SO ₂ NHR ₈ includes sulfamoyl, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N-pentylsulfamoyl group, N-isopentylsulfamoyl group, N-neopentylsulfamoyl group, N-cyclopentylsulfamoyl group, N-hexylsulfamoyl group, N-cyclohexylsulfamoyl group, N-heptylsulfamoyl group, N-cycloheptylsulfamoyl group, N-octylsulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (1,5- Dimethylhexyl) sulfamoyl group, N-cyclooctylsulfamoyl group, N-nonylsulfur group Amoyl group, N-decanylsulfamoyl group, N-tricyclodecanylsulfamoyl group, N-methoxypropylsulfamoyl group, N-ethoxypropylsulfamoyl group, N-propoxypropylsulfamoyl group, N- Isopropoxypropylsulfamoyl group, N-hexyloxypropylsulfamoyl group, N- (2-ethylhexyloxypropyl) sulfamoyl group, N- (methoxyhexyl) sulfamoyl group, N- (3-phenyl-1-methyl) Propyl) sulfamoyl group and the like.

Saturated hydrocarbon groups include alkyl and cycloalkyl groups, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, pentyl, isopentyl, neopentyl, cyclopentyl, hexyl, and cyclohexyl. Group, heptyl group, cycloheptyl group, octyl group, 2-ethylhexyl group, cyclooctyl group, nonyl group, decanyl group, tricyclodecanyl group and the like are exemplified.
Examples of the alkoxy-substituted saturated hydrocarbon group include a methoxypropyl group, an ethoxypropyl group, a hexyloxypropyl group, a 2-ethylhexyloxypropyl group, a methoxyhexyl group, and an ethoxypropyl group.

In particular, as a substituent of an aromatic hydrocarbon group having 6 to 10 carbon atoms, a methyl group, an ethyl group, a propyl group, a phenyl group, —SO ₃ R, or —SO ₂ NHR ₈ is preferable.

  Specific examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms having a substituent include a methylphenyl group, a dimethylphenyl group, a trimethylphenyl group, an ethylphenyl group, a hexylphenyl group, a decanylphenyl group, a fluorophenyl group, Examples include chlorophenyl group, bromophenyl group, hydroxyphenyl group, methoxyphenyl group, dimethoxyphenyl group, ethoxyphenyl group, hexyloxyphenyl group, decanyloxyphenyl group, trifluoromethylphenyl group and the like.

At least one of R ₁ and R ₂ or at least one of R ₃ and R ₄ is an alkyl group having 1 to 4 carbon atoms or an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms. It is preferable that
At least one of R ₁ and R ₂ and at least one of R ₃ and R ₄ is an alkyl group having 1 to 4 carbon atoms or an optionally substituted aromatic carbon atom having 6 to 10 carbon atoms. More preferably, it is a hydrogen group.
More preferably, at least one of R ₁ and R ₂ and at least one of R ₃ and R ₄ is an optionally substituted aromatic hydrocarbon group having 6 to 10 carbon atoms.
In particular, R ₅ represents carboxy group, ethoxycarbonyl, sulfo group, N- (2-ethylhexyloxypropyl) sulfamoyl, N- (1,5-dimethylhexyl) sulfamoyl, N- (3-phenyl-1-methylpropyl). ) Sulfamoyl, N- (isopropoxypropyl) sulfamoyl and the like are preferable.

（式（１−１）中、Ｒ_１０及びＲ_１１は、それぞれ独立に、フェニル基を表す。該フェニル基に含まれる水素原子は、ハロゲン原子、−Ｒ、−ＯＲ、−ＣＯ_２Ｒ、−ＳＯ_３Ｒ又は−ＳＯ_２ＮＨＲ_８に置換されていてもよい。
Ｒ_１２は、−ＳＯ_３ ⁻又は−ＳＯ_２ＮＨＲ_８を表す。
Ｒ_１３は、水素原子、−ＳＯ_３ ⁻又は−ＳＯ_２ＮＨＲ_８を表す。
Ｒ及びＲ_８は、上記と同じ意味を表す。） Moreover, it is preferable that the compound represented by Formula (1) is a compound represented by Formula (1-1).

(In formula (1-1), R ₁₀ and R ₁₁ each independently represent a phenyl group. The hydrogen atom contained in the phenyl group is a halogen atom, —R, —OR, —CO ₂ R, — It may be substituted with SO ₃ R or —SO ₂ NHR ₈ .
R ₁₂ represents —SO ₃ ^— or —SO ₂ NHR ₈ .
R ₁₃ represents a hydrogen atom, —SO ₃ ^— or —SO ₂ NHR ₈ .
R and R ₈ represent the same meaning as described above. )

（式（１ａ）中、Ｒ_ｄは、それぞれ独立に、水素原子、−ＳＯ_３ ⁻、−ＣＯ_２Ｈ又は−ＳＯ_２ＮＨＲ_ａを表す。Ｒ_ａは、２−エチルヘキシル基を表す。Ｘ及びａは、上記と同じ意味を表す。） Examples of the compound represented by formula (1) include compounds represented by formula (1a) to formula (1f).

(In formula (1a), R _d independently represents a hydrogen atom, —SO ₃ ^— , —CO ₂ H, or —SO ₂ NHR _a . R _a represents _a 2-ethylhexyl group. X and a Represents the same meaning as above.)

（式（１ｂ）中、Ｒ_ｄは、上記と同じ意味を表す。）

(In formula (1b), R _d represents the same meaning as described above.)

（式（１ｂ−１）中、Ｒ_ｄ、Ｘ及びａは、上記と同じ意味を表す。） The compound represented by the formula (1b) is a tautomer of the compound represented by the formula (1b-1).

(In formula (1b-1), R _d , X and a represent the same meaning as described above.)

（式（１ｃ）及び式（１ｄ）中、Ｒ_ｂは、それぞれ独立に、−ＳＯ_３ ⁻、−ＳＯ_３Ｎａ又は−ＳＯ_２ＮＨＲ_ａを表す。Ｒ_ａは、２−エチルヘキシル基を表す。）

(In Formula (1c) and Formula (1d), R _b independently represents —SO ₃ ^— , —SO ₃ Na, or —SO ₂ NHR _a . R _a represents _a 2-ethylhexyl group.)

（式（１ｅ）及び式（１ｆ）中、Ｒ_ｃは、水素原子、−ＳＯ_３ ⁻、−ＳＯ_３Ｈ又は−ＳＯ_２ＮＨＲ_ａを表す。Ｒ_ａは、２−エチルヘキシル基を表す。）

(In Formula (1e) and Formula (1f), R _c represents a hydrogen atom, —SO ₃ ^— , —SO ₃ H, or —SO ₂ NHR _a . R _a represents _a 2-ethylhexyl group.)

The compound represented by the formula (1) is obtained by, for example, chlorinating a dye (pigment) or dye intermediate having —SO ₃ H by a conventional method, and obtaining the dye or dye intermediate having —SO ₂ Cl thus obtained. it can be prepared by reacting an amine represented by R ₈ -NH _2.
Moreover, it can manufacture by making the dye manufactured by the method of the upper right column-lower left column of Unexamined-Japanese-Patent No. 3-78702 3 pages react with an amine after chlorination similarly to the above.

The solvent for dissolving the dye in the dye solution (A) may be water, but is preferably an organic solvent.
Examples of the organic solvent include, but are not limited to, esters such as ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, alkyl esters, Methyl lactate, ethyl lactate, methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate, methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate and the like;

  3-oxypropionic acid alkyl esters such as methyl 3-oxypropionate and ethyl 3-oxypropionate, such as methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ethyl propionate, etc .; 2-oxypropionic acid alkyl esters such as methyl 2-oxypropionate, ethyl 2-oxypropionate, propyl 2-oxypropionate, such as methyl 2-methoxypropionate, 2-methoxypropion Acid ethyl, propyl 2-methoxypropionate, methyl 2-ethoxypropionate, ethyl 2-ethoxypropionate, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, 2-methoxy- 2-methylpropio Methyl acid, 2-ethoxy-2-methylpropionic acid ethyl, etc; methyl pyruvate, ethyl pyruvate, propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, methyl 2-oxobutanoate, 2-ethyl-oxobutanoic acid, and the like;

  Ethers such as diethylene glycol dimethyl ether, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl Ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, etc .;

Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone;
Aromatic hydrocarbons such as toluene and xylene are exemplified.
These can be used alone or in combination of two or more.

  In the dye solution (A), for example, the dye is usually dissolved at about 1 to 30% by weight with respect to the total weight of the dye solution.

  The 1st filter which lets a dye solution (A) pass can be used without being specifically limited if it is conventionally used for the filtration use etc. For example, a filter made of a fluororesin such as PTFE (polytetrafluoroethylene), a polyolefin resin (including high density and ultra high molecular weight) such as polyethylene and polypropylene (PP), and the like can be given.

  The pore size of the first filter is suitably about 0.01 to 0.5 μm, preferably about 0.01 to 0.2 μm, and more preferably about 0.01 to 0.1 μm. By setting it within this range, it is possible to surely remove fine foreign matters that are mixed in the dissolved dye and inhibit the preparation of a uniform and smooth coloring composition in the subsequent step.

  Note that the filtering by the first filter may be performed only once, or may be performed twice or more. Moreover, you may combine the 1st filter of a different hole diameter within the range mentioned above. The pore diameter here can refer to the nominal value of the filter manufacturer. As a commercially available filter, for example, it can be selected from various filters provided by Nippon Pole Co., Ltd., Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Japan Microlith Co., Ltd.) or KITZ Micro Filter Co., Ltd. .

  When passing the dye solution (A) through the first filter, for example, it is suitable to adjust the pressure to a range of about 0.01 to 1.0 MPa.

Next, the dye solution (A) that has passed through the first filter is mixed with the pigment or the pigment dispersion (B) and the solvent (C), and the resulting mixture is passed through the second filter.
As the second filter, a filter formed of the same material as the first filter described above can be used. The pore size of the second filter is suitably about 0.5 to 5.0 μm, preferably about 0.5 to 2.5 μm, and more preferably about 0.5 to 1.5 μm. By setting the amount within this range, the component particles contained in the mixed solution remain and are mixed in the mixed solution, and foreign matters that hinder the preparation of a uniform and smooth coloring composition in the subsequent process are removed. can do.

The pigment in the pigment or the pigment dispersion (B) is not particularly limited as long as it is used in the field, and any pigment can be used.
The pigment may be either an organic pigment or an inorganic pigment, and examples thereof include compounds classified as Pigment in the color index (published by The Society of Dyers and Colorists).

Specifically, C.I. I. Pigment Yellow 1, 3, 12-17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, 147, 148, 150, 153, Yellow pigments such as 154, 166, 173, 194, 214;
C. I. Orange pigments such as CI Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
C. I. Red pigments such as CI Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265;

C. I. Blue pigments such as CI Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60;
C. I. Violet color pigments such as CI Pigment Violet 1, 19, 23, 29, 32, 36, 38;
C. I. Green pigments such as CI Pigment Green 7, 36, 58;
C. I. Brown pigments such as CI Pigment Brown 23 and 25;
C. I. And black pigments such as CI Pigment Black 1 and 7.
These pigments may be used alone or in combination of two or more.

  Among these pigments, organic pigments are optionally rosin-treated, surface-treated with pigment derivatives or pigment dispersants introduced with acidic groups or basic groups, and grafted onto the pigment surface with polymer compounds. Treatment, atomization treatment by sulfuric acid atomization method or the like, cleaning treatment by an organic solvent or water for removing impurities, removal treatment by ion exchange method of ionic impurities, or the like may be performed.

The pigment is preferably dispersed in a dispersant because a colored composition in a uniform dispersion state can be easily prepared.
As a dispersant for dispersing the pigment, it is suitable to use a surfactant. Examples of the surfactant include silicone-based, fluorine-based, ester-based, cationic-based, anionic-based, nonionic-based, and amphoteric surfactants. These can be used alone or in combination of two or more.

  Specific examples of surfactants include polyoxyethylene alkyl ethers, polyoxyethylene alkyl phenyl ethers, polyethylene glycol diesters, sorbitan fatty acid esters, fatty acid-modified polyesters, tertiary amine-modified polyurethanes, and polyethyleneimines. The product names include KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), F-Top (Mitsubishi Materials Electronic Chemicals Co., Ltd.), MegaFuck (manufactured by DIC Corporation), and Florard. (Manufactured by Sumitomo 3M), Asahi Guard (manufactured by Asahi Glass Co., Ltd.), Surflon (manufactured by AGC Seimi Chemical Co., Ltd.), Solsperse (manufactured by Geneca Corporation), EFKA (manufactured by CIBA), Ajispur (Ajinomoto Fine) (Techno Co., Ltd.), Disperbyk (Bic Chemie) etc. It is below.

  The dispersant is suitably about 1 part by weight or less, preferably about 0.05 to 0.5 part by weight per part by weight of the pigment. By making the usage-amount of a dispersing agent into this range, the pigment dispersion liquid of a uniform dispersion state can be obtained.

Examples of the solvent (C) include the same water and organic solvents exemplified as the solvent for the dye solution (A).
In the mixed solution of the dye solution (A), the pigment or pigment dispersion (B), and the solvent (C), the total weight of the dye solution (A), the pigment or pigment dispersion (B), and the solvent (C). On the other hand, the total weight of the dye and the pigment is preferably adjusted to a range of 1 to 30% by weight. In this case, the dye and the pigment are preferably contained in a ratio of about 1:99 to 99: 1.
By adjusting to such a range, when the colored composition is used for the production of a color filter, it is possible to achieve high brightness and high contrast of the obtained color filter.

  It is suitable to adjust the pressure at the time of letting the liquid mixture mentioned above pass to the 2nd filter to the range of about 0.01-1.0 MPa similarly to passage of the 1st filter.

  It is preferable that the mixed solution further contains at least one selected from the group consisting of a resin (D), a photopolymerizable compound (E), and a photopolymerization initiator (F). Addition of these components to the mixed solution may be either before or after passing through the second filter, but in order to remove foreign matters effectively and simply, these components are added to the mixed solution to obtain a colored composition. It is preferable that the obtained mixed solution is passed through a second filter later.

The resin (D) does not necessarily mean only a polymer, but includes a copolymer, an oligomer, and / or a monomer such as a polymerizable or crosslinkable (except for the following photopolymerizable compound (E)). It may be a unit as long as it is a unit capable of constituting a resin.
As resin (D), what is alkali-soluble is preferable, for example. Moreover, what has heat resistance is preferable. Specific examples include (meth) acrylic resins, polyhydroxystyrene resins, polysiloxane resins, acrylamide resins, and copolymer resins thereof. Especially, what has an acidic functional group as an alkali-soluble resin is preferable, and resin etc. which have a structural unit derived from the unsaturated compound which has an acidic functional group as the resin which has an acidic functional group are mentioned, for example. In the present specification, (meth) acryl represents acryl and / or methacryl.

  A carboxy group is mentioned as an acidic functional group. For example, examples of the unsaturated compound having an acidic functional group include unsaturated carboxylic acids having one or more carboxy groups in the molecule, such as unsaturated monocarboxylic acids or unsaturated dicarboxylic acids. Specifically, crotonic acid, itaconic acid, maleic acid, fumaric acid, citraconic acid, mesaconic acid, cinnamic acid, succinic acid mono [2- (meth) acryloyloxyethyl] or ω-carboxypolycaprolactone mono (meth) acrylate Etc.

  Resin (D) is, for example, an aromatic vinyl compound, an unsaturated carboxylic acid ester, an unsaturated carboxylic acid aminoalkyl ester, or an unsaturated carboxylic acid glycidyl ester in addition to the unsaturated compound having an acidic functional group described above. Carboxylic acid vinyl esters, unsaturated ethers, vinyl cyanide compounds, unsaturated amides, unsaturated imides, aliphatic conjugated dienes, macros having a monoacryloyl group or a monomethacryloyl group at the end of the polymer molecular chain Monomers of monomers may be copolymerized.

  Examples of the aromatic vinyl compound include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o -Vinyl benzyl methyl ether, m-vinyl benzyl methyl ether, p-vinyl benzyl methyl ether, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, indene, etc. are mentioned. Styrene and p-vinyltoluene are preferred.

  As unsaturated carboxylic acid esters, methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, sec -Butyl (meth) acrylate, tert-butyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate , 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate Relate, 2-methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, diethylene glycol methyl ether mono (meth) acrylate, triethylene glycol methyl ether mono (meth) acrylate, propylene glycol methyl ether mono (meth) acrylate, Dipropylene glycol methyl ether mono (meth) acrylate, isobornyl (meth) acrylate, dicyclopentadienyl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, O- (meth) acryloylglycerin and the like It is done. Preferred are methyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, and dicyclopentadienyl (meth) acrylate.

  Examples of unsaturated carboxylic acid aminoalkyl esters include 2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate, 2-dimethylaminopropyl (meth) acrylate, 3 -Aminopropyl (meth) acrylate, 3-dimethylaminopropyl (meth) acrylate, etc. are mentioned. 2-Aminoethyl (meth) acrylate is preferred.

  Examples of unsaturated carboxylic acid glycidyl esters include glycidyl (meth) acrylate. Glycidyl methacrylate is preferred.

  Examples of the vinyl carboxylates include vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate and the like. Preferred is vinyl propionate.

  Examples of unsaturated ethers include vinyl methyl ether, vinyl ethyl ether, and allyl glycidyl ether. Allyl glycidyl ether is preferred.

  Examples of the vinyl cyanide compound include acrylonitrile, methacrylonitrile, α-chloroacrylonitrile and the like. Acrylonitrile is preferred.

  Examples of unsaturated amides include (meth) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide, and the like. N-2-hydroxyethyl (meth) acrylamide is preferred.

  Examples of unsaturated imides include maleimide, N-phenylmaleimide, N-cyclohexylmaleimide and the like. N-phenylmaleimide is preferred.

  Examples of the aliphatic conjugated dienes include 1,3-butadiene, isoprene, chloroprene and the like. Isoprene is preferred.

  Macromonomers having an acryloyl group or methacryloyl group at the end of the polymer molecular chain include an acryloyl group or a methacryloyl group at the end of polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, polysiloxane, etc. The macromonomer which has. Preferred is a macromonomer having an acryloyl group or a methacryloyl group at the end of polystyrene.

［式（Ｖ）および式（ＶＩ）中、Ｒ²¹およびＲ²²は、それぞれ独立に、水素原子または炭素数１〜６のアルキル基を表す。］ Further, for example, a unit represented by the formula (V) and a unit represented by the formula (VI) may be used.

[In Formula (V) and Formula (VI), R ²¹ and R ²² each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. ]

R ²¹ and R ²² include a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, tert-butyl group, n-pentyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 1-ethylpropyl group, 2-ethylpropyl group, n-hexyl group, 1-methylpentyl group, 2-methylpentyl group, 3-methylpentyl group, 4-methylpentyl group 1-ethylbutyl group, 2-ethylbutyl group, 3-ethylbutyl group and the like. Preferred are a hydrogen atom, methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group and tert-butyl group, and more preferred are a hydrogen atom, methyl group and ethyl group.

Specific examples of the resin (D) include methacrylic acid / benzyl methacrylate copolymer, methacrylic acid / benzyl methacrylate / styrene copolymer, methacrylic acid / benzyl methacrylate / isobornyl methacrylate copolymer, methacrylic acid / styrene. / Benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / constituent component represented by formula (V) (wherein, in formula (V), R ²¹ represents a methyl group and R ²² represents a hydrogen atom) / Benzyl methacrylate copolymer, a component represented by formula (V) (wherein, in formula (V), R ²¹ represents a methyl group and R ²² represents a hydrogen atom). / benzyl methacrylate copolymer, component represented by methacrylic acid / formula (VI) (However, in this case, the formula (VI), R ²¹ is methyl The stands, R ²² is. Represents a hydrogen atom) / styrene copolymer / tricyclodecanyl methacrylate copolymer and the like are preferable.

  Content of resin (D) is a weight fraction with respect to solid content of a coloring composition, Preferably it is 12-30 weight%, More preferably, it is 16-24 weight%, Especially preferably, 18-22 % By weight. When the content of the resin (D) is within this range, a pattern can be formed and the resolution and the remaining film ratio tend to be improved, which is preferable.

The resin having the structural component represented by the formula (V) is a compound represented by the formula (V-1) in the resin containing the structural unit derived from the unsaturated monocarboxylic acid or unsaturated dicarboxylic acid mentioned above. Can be obtained by reacting. For example, methacrylic acid / constituent component represented by formula (V) (wherein, in formula (V), R ²¹ represents a methyl group and R ²² represents the same meaning as described above) / benzyl methacrylate. The polymer is obtained by polymerizing methacrylic acid and benzyl methacrylate to obtain a two-component copolymer, and the obtained two-component copolymer and a compound represented by the formula (V-1) (here, the formula (V-1) can be obtained by reacting R ²² with the same meaning as described above.

Methacrylic acid / constituent component represented by formula (VI) (wherein, in formula (VI), R ²¹ represents a methyl group and R ²² represents a methyl group) / styrene copolymer / tricyclo The decanyl methacrylate copolymer can be obtained by reacting benzyl methacrylate, methacrylic acid, or a monomethacrylate copolymer having a tricyclodecane skeleton with glycidyl methacrylate.

  The polystyrene equivalent weight average molecular weight of the resin (D) is preferably 5,000 to 100,000, more preferably 6,000 to 90,000, and particularly preferably 7,000 to 80,000. When the molecular weight is in this range, the coating film hardness is improved, the residual film ratio is high, the solubility of the unexposed area in the developer is good, and the resolution tends to be improved, which is preferable.

  The photopolymerizable compound (E) is a compound that can be polymerized by an active radical, an acid, or the like generated from a photopolymerization initiator (F) described later when irradiated with light, for example, a polymerizable carbon- Examples thereof include compounds having a carbon unsaturated bond.

  The photopolymerizable compound (E) is preferably a trifunctional or higher polyfunctional photopolymerizable compound. Examples of the trifunctional or higher polyfunctional photopolymerizable compound include pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, and dipentaerythritol hexa (meth) acrylate. These may be used alone or in combination of two or more.

  The content of the photopolymerizable compound (E) is preferably 7 to 65% by weight, more preferably 13 to 60% by weight, based on the solid content of the coloring composition, and more preferably 13 to 60% by weight. Preferably it is 17 to 55% by weight. When the content of the photopolymerizable compound (E) is within this range, when the color filter is produced, the curing is sufficiently performed, the film thickness ratio before and after the development is improved, and the pattern is less likely to be undercut. It is preferable because the adhesiveness tends to be improved.

  The photopolymerization initiator (F) has a function of generating radicals when irradiated with ultraviolet rays such as g-line, i-line, and h-line, and is not particularly limited. For example, acetophenone Compounds, active radical generators, acid generators and the like.

  Examples of acetophenone compounds include diethoxyacetophenone, 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one, 2-hydroxy-2-methyl-1-phenylpropan-1-one , Benzyldimethyl ketal, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl] propan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2-hydroxy-2-methyl-1- [ An oligomer of 4- (1-methylvinyl) phenyl] propan-1-one and the like are preferable, and 2-methyl-2-morpholino-1- (4-methylthiophenyl) propan-1-one and the like are preferable.

The active radical generator generates an active radical when irradiated with light.
Examples of the active radical generator include benzoin compounds, benzophenone compounds, thioxanthone compounds, triazine compounds, and oxime compounds.

  Examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzoin isobutyl ether.

  Examples of the benzophenone compounds include benzophenone, methyl o-benzoylbenzoate, 4-phenylbenzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, 3,3 ′, 4,4′-tetra (tert-butylperoxy). Carbonyl) benzophenone, 2,4,6-trimethylbenzophenone and the like.

  Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.

  Examples of triazine compounds include 2,4-bis (trichloromethyl) -6- (4-methoxyphenyl) -1,3,5-triazine and 2,4-bis (trichloromethyl) -6- (4- Methoxynaphthyl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- (4-methoxystyryl) -1,3,5-triazine, 2,4-bis (trichloromethyl) -6 -[2- (5-methylfuran-2-yl) ethenyl] -1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (furan-2-yl) ethenyl]- 1,3,5-triazine, 2,4-bis (trichloromethyl) -6- [2- (4-diethylamino-2-methylphenyl) ethenyl] -1,3,5-triazine, 2,4-bis ( Trichloromethyl)- - such as [2- (3,4-dimethoxyphenyl) ethenyl] -1,3,5-triazine.

  Examples of oxime compounds include O-acyl oxime compounds. Specifically, 1- (4-phenylsulfanyl-phenyl) -butane-1,2-dione 2-oxime-O-benzoate, 1- (4-phenylsulfanyl-phenyl) -octane-1,2-dione 2-oxime-O-benzoate, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] ethanone 1-O-acetate, 1- [9-ethyl-6- ( 2-methyl-4- (3,3-dimethyl-2,4-dioxacyclopentanylmethyloxy) benzoyl) -9H-carbazol-3-yl] ethanone 1-O-acetate and the like.

  Furthermore, as an active radical generator, for example, 2,4,6-trimethylbenzoyldiphenylphosphine oxide, 2,2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2 '-Biimidazole, 10-butyl-2-chloroacridone, 2-ethylanthraquinone, benzyl, 9,10-phenanthrenequinone, camphorquinone, methyl phenylglyoxylate, titanocene compound and the like may be used.

  Examples of the acid generator include 4-hydroxyphenyldimethylsulfonium p-toluenesulfonate, 4-hydroxyphenyldimethylsulfonium hexafluoroantimonate, 4-acetoxyphenyldimethylsulfonium p-toluenesulfonate, 4-acetoxyphenyl methyl. Onium salts such as benzylsulfonium hexafluoroantimonate, triphenylsulfonium p-toluenesulfonate, triphenylsulfonium hexafluoroantimonate, diphenyliodonium p-toluenesulfonate, diphenyliodonium hexafluoroantimonate, nitrobenzyl tosylate, benzoin And tosylate.

  Among the compounds described above as active radical generators, there are compounds that generate acid simultaneously with active radicals. For example, triazine photopolymerization initiators are also used as acid generators.

  Content of a photoinitiator (F) is a weight fraction with respect to the total amount of resin (D) and a photopolymerizable compound (E), Preferably it is 0.1 to 30 weight%, More preferably 1 to 20% by weight. When the content of the photopolymerization initiator is within this range, it is preferable because the sensitivity is increased, the exposure time is shortened, and the productivity is improved.

The coloring composition of the present invention may further contain a photopolymerization initiation assistant.
The photopolymerization initiation assistant is usually used in combination with the photopolymerization initiator (F), and accelerates the polymerization of the photopolymerizable compound whose polymerization has been initiated by the photopolymerization initiator.
Examples of photopolymerization initiation assistants include amine compounds, alkoxyanthracene compounds, and thioxanthone compounds.

  Examples of amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, and 2-dimethylaminoethyl benzoate. 2-ethylhexyl 4-dimethylaminobenzoate, N, N-dimethylparatoluidine, 4,4′-bis (dimethylamino) benzophenone (commonly known as Michler's ketone), 4,4′-bis (diethylamino) benzophenone, 4,4 ′ -Bis (ethylmethylamino) benzophenone and the like. Of these, 4,4'-bis (diethylamino) benzophenone is preferable.

  Examples of the alkoxyanthracene compound include 9,10-dimethoxyanthracene, 2-ethyl-9,10-dimethoxyanthracene, 9,10-diethoxyanthracene, 2-ethyl-9,10-diethoxyanthracene, and 9,10. -Dibutoxyanthracene, 2-ethyl-9,10-dibutoxyanthracene, etc. are mentioned.

Examples of the thioxanthone compound include 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-diethylthioxanthone, 2,4-dichlorothioxanthone, 1-chloro-4-propoxythioxanthone, and the like.
The photopolymerization initiation assistant may be used alone or in combination of two or more.
As the photopolymerization initiation auxiliary agent, for example, a commercially available product such as a trade name “EAB-F” (Hodogaya Chemical Co., Ltd.) can be used.

  The photopolymerization initiation assistant is preferably used in an amount of 0.01 to 10 mol, particularly 0.01 to 5 mol, per 1 mol of the photopolymerization initiator (F).

  Hereinafter, the manufacturing method of the coloring composition of this invention is demonstrated in detail by an Example. Unless otherwise specified, “%” and “parts” in the examples are% by mass and parts by mass.

Synthesis example 1
A flask equipped with a condenser and a stirrer was charged with 15 parts of sulforhodamine B (manufactured by Kanto Chemical), 150 parts of chloroform and 9.8 parts of N, N-dimethylformamide, and while maintaining the temperature at 20 ° C. or lower with stirring, 12.0 parts of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and then cooled to 20 ° C. While maintaining the reaction solution after cooling at 20 ° C. or lower with stirring, a mixed solution of 13.9 parts of 2-ethylhexylamine and 24.5 parts of triethylamine was added dropwise. Then, it was made to react by stirring at the same temperature for 5 hours. Subsequently, after the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added and vigorously stirred. This mixture was added to a mixture of 375 parts of ion exchange water with stirring to precipitate crystals. The precipitated crystals were separated by filtration, washed thoroughly with ion exchange water, and dried under reduced pressure at 60 ° C. to obtain 14.7 parts of dye A1.

Synthesis example 2
A flask equipped with a condenser and a stirrer is charged with 15 parts of a dye represented by the formula A0-2 (manufactured by Chugai Kasei), 150 parts of chloroform and 7.1 parts of N, N-dimethylformamide, and is stirred at 20 ° C. or lower. While maintaining the above, 8.7 parts of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and then cooled to 20 ° C. While maintaining the reaction solution after cooling at 20 ° C. or lower with stirring, a mixed solution of 10 parts of 2-ethylhexylamine and 17.7 parts of triethylamine was added dropwise. Then, it was made to react by stirring at the same temperature for 5 hours. Subsequently, after the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added and vigorously stirred. This mixture was added to a mixture of 375 parts of ion exchange water with stirring to precipitate crystals. The precipitated crystals were separated by filtration, washed thoroughly with ion exchange water, and dried under reduced pressure at 60 ° C. to obtain 12.7 parts of dye A2 (mixed dye of dye A2-1 to dye A2-7).

（式（Ａ２）中、Ｒ_ｂは、それぞれ独立に、−ＳＯ_３ ⁻、−ＳＯ_３Ｎａ又は−ＳＯ_２ＮＨＲ_ａを表す。Ｒ_ａは、２−エチルヘキシル基を表す。）

(In Formula (A2), R _b independently represents —SO ₃ ^— , —SO ₃ Na, or —SO ₂ NHR _a . R _a represents _a 2-ethylhexyl group.)

Synthesis example 3
A flask equipped with a condenser and a stirrer is charged with 15 parts of a dye represented by formula A0-3 (manufactured by Chugai Kasei), 150 parts of chloroform and 8.9 parts of N, N-dimethylformamide, and is stirred at 20 ° C. or lower. While maintaining the above, 10.9 parts of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and then cooled to 20 ° C. While maintaining the reaction solution after cooling at 20 ° C. or lower with stirring, a mixed solution of 12.5 parts of 2-ethylhexylamine and 22.1 parts of triethylamine was added dropwise. Then, it was made to react by stirring at the same temperature for 5 hours. Subsequently, after the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added and vigorously stirred. This mixture was added to a mixture of 375 parts of ion exchange water with stirring to precipitate crystals. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 11.3 parts of dye A3 (mixed dye of dye A3-1 to dye A3-8).

（式（Ａ３）中、Ｒ_ｃは、それぞれ独立に、−ＳＯ_２ＮＨ−Ｒ_ａ、−ＳＯ_３Ｈ、−ＳＯ_３ ⁻又は−Ｈを表す。Ｒ_ａは、２−エチルヘキシル基を表す。）

(In formula (A3), each R _c independently represents —SO ₂ NH—R _a , —SO ₃ H, —SO ₃ ^— or —H. R _a represents _a 2-ethylhexyl group.)

Synthesis example 4
Nitrogen was flowed at a rate of 0.02 L / min into a 1 L flask equipped with a reflux condenser, a dropping funnel and a stirrer to form a nitrogen atmosphere, 100 parts by mass of ethyl lactate was added, and the mixture was heated to 70 ° C. with stirring. Subsequently, 60 parts by mass of methacrylic acid and 3,4-epoxytricyclo [5.2.1.0 ^2.6 ] decyl acrylate (a compound represented by the formula (B1-1-1) and a formula (B1-2) The compound represented by 1) was mixed at a molar ratio of 50:50) 200 parts by mass was dissolved in 100 parts by mass of ethyl lactate to prepare a solution. This solution was dropped into a flask kept at 70 ° C. for 4 hours using a dropping funnel. On the other hand, a solution obtained by dissolving 30 parts by mass of a polymerization initiator 2,2′-azobis (2,4-dimethylvaleronitrile) in 190 parts by mass of ethyl lactate was dropped into the flask using another dropping funnel over 4 hours. did. After completion of the dropwise addition of the polymerization initiator solution, the temperature was maintained at 70 ° C. for 4 hours, and then cooled to room temperature. The weight average molecular weight Mw was 7,700, the dispersity was 2.5, and the solid content was 40% by mass. A resin solution D1 having an acid value of 42 mg-KOH / g was obtained.

The polystyrene-reduced weight average molecular weight of the above resin was measured using the GPC method under the following conditions.
Apparatus: HLC-8120GPC (manufactured by Tosoh Corporation)
Column; TSK-GELG2000HXL
Column temperature: 40 ° C
Solvent: THF
Flow rate: 1.0 mL / min
Test liquid solid concentration: 0.001 to 0.01% by mass
Injection volume: 50 μL
Detector; RI
Reference material for calibration; TSK STANDARD POLYSTYRENE
F-40, F-4, F-1, A-2500, A-500
(Manufactured by Tosoh Corporation)

Synthesis example 5
To 100 parts of 2,2′-benzidine disulfonic acid (containing 30% water), 1000 parts of water was added. Thereafter, the solution was adjusted to pH 7 to 8 with a 30% aqueous sodium hydroxide solution under ice cooling, 56.1 parts of sodium nitrite was added, and the mixture was stirred for 30 minutes. 148 parts of 35% hydrochloric acid was added little by little to give a brown solution and stirred for 2 hours. An aqueous solution prepared by dissolving 38.3 parts of amidosulfuric acid in 383 parts of water was added to the reaction solution and stirred to obtain a suspension A0-4 containing a diazonium salt.
761 parts of water was added to 76.1 parts of 1-ethyl-3-cyano-4-methyl-6-hydroxypyrid-2-one. Thereafter, the solution was adjusted to pH 8-9 with a 30% aqueous sodium hydroxide solution under ice cooling and stirred to give a colorless solution. Furthermore, the suspension A0-4 containing a diazonium salt was dropped with a pump while adjusting the obtained solution to pH 8 to 9 with a 30% aqueous sodium hydroxide solution. After completion of dropping, the mixture was further stirred for 3 hours to obtain a yellow suspension. The yellow solid obtained by filtration was dried at 60 ° C. under reduced pressure to obtain 157 parts of a compound represented by the formula (A0-5).

A flask equipped with a condenser and a stirrer is charged with 5 parts of the compound represented by the formula (A0-5), 50 parts of chloroform, and 2.1 parts of N, N-dimethylformamide. While maintaining, 3 parts of thionyl chloride was added dropwise. After completion of the dropwise addition, the temperature was raised to 50 ° C., the reaction was continued for 5 hours at the same temperature, and the mixture was cooled to 20 ° C. While maintaining the cooled reaction solution at 20 ° C. or lower with stirring, a mixed solution of 4 parts of 2-ethylhexylamine and 14 parts of triethylamine was added dropwise. Thereafter, the reaction was carried out by stirring overnight at the same temperature. Subsequently, the solvent of the obtained reaction mixture was distilled off with a rotary evaporator, a small amount of methanol was added, and the mixture was vigorously stirred. This mixture was added to a mixed solution of 29 parts of acetic acid and 300 parts of ion-exchanged water with stirring to precipitate crystals. The precipitated crystals were separated by filtration, washed well with ion-exchanged water, and dried under reduced pressure at 60 ° C. to obtain 5.6 parts of Dye A5.

Example 1
Preparation of dye solution (A) 1
Dye A1 3.5 parts Ethyl lactate 35 parts are mixed and passed through a first filter (φ0.1 μm, manufactured by Microlith, model number: PTVW04700, material: polyethylene) with nitrogen pressure (0.3 MPa). Solution 1 was obtained.

Preparation 1 of pigment dispersion (B)
C. I. Pigment Blue 15: 6 20 parts Acrylic pigment dispersant 5 parts Propylene glycol monomethyl ether acetate 137 parts were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion Liquid 1.

Preparation of coloring composition 1 Dye solution (A): Dye solution 1 35 parts Pigment dispersion (B): Pigment dispersion 1 162 parts Solvent (C): Ethyl lactate 300 parts Resin (D): Resin solution D1 105 parts Light Polymerizable compound (E): dipentaerythritol hexaacrylate
(KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.)
50 parts Photopolymerization initiator (F): Irgacure OXE 01
(Ciba Japan Co., Ltd.) 15 parts were mixed and the liquid mixture 1 was obtained. The obtained mixed liquid 1 is passed through a second filter (φ4.5 μm, manufactured by Pall, model number: HDCII J045047100, material: polypropylene) at a nitrogen pressure (0.3 MPa) to obtain a colored composition 1. It was.

Example 2
A colored composition 2 was obtained in the same manner as in Example 1 except that the dye A1 was changed to the dye A2.

Example 3
A colored composition 3 was obtained in the same manner as in Example 1 except that the dye A1 was changed to the dye A3.

Example 4
A colored composition 4 was obtained in the same manner as in Example 1 except that the dye A1 was changed to rhodamine B (manufactured by Taoka Chemical).

Example 5
A colored composition 5 was obtained in the same manner as in Example 1 except that the dye A1 was changed to Rhodamine B base (manufactured by Aldrich).

Example 6
Preparation of dye solution (A) 6
Dye A5 5 parts Ethyl lactate 95 parts were mixed and passed through a first filter (φ0.45 μm, manufactured by Kanto Chemical Co., Inc., model number: HLC-DISK96911-00, material: polyvinyl difluoride) to obtain dye solution 6 .

Preparation 2 of pigment dispersion (B)
C. I. Pigment Red 177 31 parts C.I. I. Pigment Red 254 58 parts Acrylic pigment dispersant 5 parts Propylene glycol monomethyl ether acetate 137 parts were mixed and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion Liquid 2.

Preparation of coloring composition 6 Dye solution (A): Dye solution 6 190 parts Pigment dispersion (B): Pigment dispersion 2 384 parts Solvent (C): Propylene glycol monomethyl ether acetate 198 parts Resin (D): Resin solution D1 50 parts Photopolymerizable compound (E): Dipentaerythritol hexaacrylate
(KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 25 parts Photopolymerization initiator (F): Irgacure OXE 01 (manufactured by Ciba Japan) 10 parts were mixed to obtain a mixed solution 6. The obtained mixed liquid 6 was passed through a second filter (φ0.5 μm, manufactured by ADVANTEC, model number: LABODISC-50JP 50JP050AN, material: polytetrafluoroethylene) to obtain a colored composition 6.

Example 7
Preparation of dye solution (A) 7
Neozapon yellow073 (manufactured by BASF) 5 parts Ethyl lactate 95 parts are mixed and passed through the first filter (φ0.45 μm, manufactured by Kanto Chemical Co., model number: HLC-DISK96911-00, material: polyvinyl difluoride), dye Solution 7 was obtained.

Preparation of pigment dispersion (B) 3
C. I. Pigment Green 58 12 parts Acrylic pigment dispersant 5 parts Propylene glycol monomethyl ether acetate 128 parts were mixed, and the pigment was sufficiently dispersed using a bead mill to obtain Pigment Dispersion Liquid 3.

Preparation of coloring composition 7 Dye solution (A): Dye solution 7 255 parts Pigment dispersion (B): Pigment dispersion 3 271 parts Solvent (C): Propylene glycol monomethyl ether acetate 26 parts Solvent (C): Propylene glycol monomethyl Ether 66 parts Resin (D): Resin solution D1 50 parts Photopolymerizable compound (E): Dipentaerythritol hexaacrylate
(KAYARAD DPHA; manufactured by Nippon Kayaku Co., Ltd.) 25 parts Photopolymerization initiator (F): Irgacure OXE 01 (manufactured by Ciba Japan) 10 parts were mixed to obtain a mixed solution 7. The obtained mixed liquid 7 was passed through a second filter (φ0.5 μm, manufactured by ADVANTEC, model number: DISMIC-50JP, material: polytetrafluoroethylene) to obtain a colored composition 7.

Comparative Example 1
A colored composition H1 was obtained in the same manner as in Example 1 except that the dye solution (A) was not passed through the first filter and that the mixed solution 1 was passed twice through the second filter.

[Foreign matter observation]
A colored composition was applied by spin coating on a 2-inch square glass substrate (Eagle 2000; manufactured by Corning), and then pre-baked at 100 ° C. for 3 minutes. After cooling, the substrate coated with the coloring composition was irradiated with light using an exposure machine (TME-150RSK; manufactured by Topcon Corporation) at an exposure amount of 150 mJ / cm ² (based on 365 nm) in an air atmosphere, Post-baking was performed in an oven at 220 ° C. for 20 minutes.
About the coating film on the obtained glass substrate, it observed with the optical microscope (250 times (transmission measurement)), and counted the number of the micro foreign materials per fixed area visually. When the number is 10 or less, it is determined to be acceptable and indicated by a circle in the table.
The results are shown in Table 1.

  In the coating film formed using the coloring composition of Examples 1-7, there was little generation | occurrence | production of a foreign material and the favorable coating-film state was confirmed.

  The colored composition production method of the present invention is widely used in various film or film production methods using a composition solution containing a plurality of components, for example, soluble or insoluble components such as dyes and pigments. Can be used.

Claims (6)

A first step of passing the dye solution (A) through a first filter;
Dye solution (A), pigment or pigment dispersion (B) and solvent (C) that have passed through the first filter
A second step of passing the liquid mixture containing: through a second filter;
A method for producing a colored composition comprising:
The manufacturing method whose solvent of dye solution (A) is an organic solvent. A first step of passing the dye solution (A) through a first filter;
Dye solution (A), pigment or pigment dispersion (B) and solvent (C) that have passed through the first filter
A second step of passing the liquid mixture containing: through a second filter;
A method for producing a colored composition for a color filter comprising:
The manufacturing method of the coloring composition for color filters whose solvent of dye solution (A) is an organic solvent. The method for producing a colored composition according to claim 1 or 2, wherein the ratio of the pore diameter of the first filter to the pore diameter of the second filter is 1: 1.1 to 1: 500. The method for producing a colored composition according to any one of claims 1 to 3, wherein the pore size of the first filter is 0.01 to 0.5 µm. The pore diameter of a 2nd filter is 0.5-5.0 micrometers, The manufacturing method of the coloring composition in any one of Claims 1-4. The mixed liquid is a mixed liquid further containing at least one selected from the group consisting of a resin (D), a photopolymerizable compound (E), and a photopolymerization initiator (F). The manufacturing method of the coloring composition of description.