TWI603151B - Colored composition, color filter and display element - Google Patents

Description

Coloring composition, color filter, and display element

The present invention relates to a coloring composition, a color filter, and a display element, and more particularly to a color liquid crystal display element, a solid-state imaging element, an organic EL display element, an electronic paper for forming a pair for a transmissive or reflective type. A coloring composition used in a coloring layer useful for a color filter, a color filter including a coloring layer formed using the coloring composition, and a display element including the color filter.

When a color filter is produced using a coloring sensitizing radiation composition, there is known a method in which a colored radiation-sensitive composition is applied onto a substrate and dried, and then the dried coating film is irradiated with radiation in a desired pattern shape (hereinafter, In order to "exposure"), development is performed to obtain pixels of respective colors (Patent Documents 1 to 2). Further, a method of forming a black matrix by using a photopolymerizable composition in which carbon black is dispersed is also known (Patent Document 3).

[Previous Technical Literature] [Patent Literature]

[Patent Document 1] Japanese Patent Laid-Open No. 2-144502

[Patent Document 2] Japanese Patent Laid-Open No. 3-53201

[Patent Document 3] Japanese Patent Laid-Open No. Hei 6-35188

In recent years, in the technical field of color filters, the reduction of the exposure amount and the reduction of the tact time have become mainstream, and in order to cope with the demand for high color purity of color liquid crystal display elements, the coloring radiation is colored. The proportion of the pigment contained in the sexual composition tends to increase gradually. Under such circumstances, various problems have become apparent when manufacturing color filters. For example, there is a problem in that the pixel pattern is turbid after the development described above, and the inspection step performed after the development step is delayed, and the production efficiency is lowered. In addition, there is a problem that stain-like color unevenness (hereinafter referred to as "water spot") occurs on the pixel pattern after water washing after development, and the inspection step is delayed and the production efficiency is lowered. Further, if a high-temperature heating step (for example, post-baking after development) is performed, there is also a problem that the luminance of the pixel is lowered and foreign matter is generated in the pixel pattern.

Accordingly, an object of the present invention is to provide a coloring composition that solves various problems occurring in a developing step and a heating step in the production of a color filter. Further, an object of the present invention is to provide a color filter including a coloring layer containing the colored composition, and a display element including the color filter.

As a result of intensive studies, the present inventors have found that the above problems can be solved by combining a specific photopolymerization initiator and a polyfunctional thiol.

In other words, the present invention provides a coloring composition comprising (A) a colorant, (B) a binder resin, (C) a photopolymerization initiator represented by the following formula (1), and (D) having two or more A compound having a polymerizable unsaturated bond and (E) a polyfunctional thiol.

In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 4 to 20 carbon atoms or a phenyl group. Here, a part or all of the hydrogen atoms of the phenyl group may be substituted by an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms.

R ² represents a methylene group or an alkylene group having 2 to 20 carbon atoms.

R ³ represents an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a phenyl group or a naphthyl group.

R ⁵ represents a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 9-fluorenyl group, a 2-furyl group or a 2-thienyl group. Here, a part or all of the hydrogen atoms of these groups may be substituted by an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. ]

Further, the present invention provides a color filter including a coloring layer formed using the coloring composition, and a display element including the color filter. Here, the "colored layer" refers to each color pixel, black matrix, black spacer, or the like used for the color filter.

When the colored composition of the present invention is used, turbidity or water spots are less likely to occur in the pixel pattern after the development step, so that the color filter can be produced with high productivity. In addition, it is possible to suppress the accompanying high temperature heating step The brightness is reduced or foreign matter is generated, so that a high-quality color filter can be manufactured.

Therefore, the coloring composition of the present invention can be suitably used for producing a color filter for a color liquid crystal display element, a color filter for color decomposition of a solid-state image sensor, a color filter for an organic EL display element, and an electronic paper. Color filters are representative of various color filters.

[Formation of the Invention]

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the constituent components of the colored composition of the present invention will be described.

- (A) colorant -

The coloring agent (A) in the present invention is not particularly limited, and may be any of an organic pigment, an inorganic pigment, and a natural pigment. However, since color filters are required to have high color purity, brightness, contrast, and the like, It is preferably an organic pigment.

The colored composition of the present invention can be used to form a coloring layer of each color pixel, a black matrix, a black spacer, or the like constituting a color filter, and generally, as a green color for forming a tendency to increase the content of a coloring agent or The coloring composition of red pixels is particularly useful.

For the case of a colored composition for forming a green pixel, a green colorant can be used as the (A) colorant. Examples of the green colorant include a copper halide phthalocyanine, a zinc halide phthalocyanine, a magnesium halide phthalocyanine, an aluminum halide phthalocyanine, a titanium halide phthalocyanine, a palladium halide phthalocyanine, a manganese halide phthalocyanine, and an iron halide. Green pigments such as phthalocyanine, cobalt halide phthalocyanine, nickel halide phthalocyanine, tin halide phthalocyanine, halogenated phthalocyanine, and indium halide phthalocyanine. Further, examples of the halogen include a chlorine atom and a bromine atom.

Among them, from the viewpoint of obtaining a green pixel having high luminance, a zinc halide phthalocyanine is preferred, and zinc bromide phthalocyanine or zinc bromide phthalocyanine is particularly preferred. The zinc bromide phthalocyanine is a pigment classified into C.I. Pigment Green 58 in the color index (C.I.) name, and is preferably a structure represented by the following formula (2).

[In the formula (2), X represents a chlorine atom or a bromine atom independently of each other. 10 to 15 of all X are bromine atoms, and the rest are chlorine atoms. ]

In the formula (2), the chlorine atom in all of X is preferably from 1 to 6. The bromine atom can be appropriately selected in the range of 10 to 15 in such a manner that the total number of X is 16.

In the present invention, the green colorant can be used singly or in combination of two or more.

For the case of a colored composition for forming a green pixel, a yellow colorant is usually used together with the green colorant. As a yellow coloring agent, it is preferred to use quinacridone from the viewpoint of obtaining a green pixel having high luminance. At least one of a pigment or an azo barbituric acid metal complex compound pigment. As the quinophthalone pigment, C.I. Pigment Yellow 138 is preferred. In addition, as the barbituric acid metal complex compound pigment, a pigment described in JP-A-2001-354869 and JP-A-2006-16506 is preferably used in addition to C.I. Pigment Yellow 150. When C.I. Pigment Yellow 138 is used as the coloring composition of the present invention, it is preferable from the viewpoint of suppressing foreign matter generated by the high-temperature heating step.

On the other hand, in the case of a colored composition for forming a red pixel, a red coloring agent can be used as the (A) coloring agent. Examples of the red coloring agent include C.I. Pigment Red 166, C.I. Pigment Red 177, C.I. Pigment Red 224, C.I. Pigment Red 242, C.I. Pigment Red 254, and the like. Among them, from the viewpoint of obtaining a red pixel having a high luminance, it is preferred to use two or more selected from the group consisting of C.I. Pigment Red 177, C.I. Pigment Red 242, and C.I. Pigment Red 254.

In the case of a colored composition for forming a red pixel, a yellow colorant is sometimes used together with a red coloring agent for coloring. As the yellow coloring agent, in addition to the yellow pigment for forming the green pixel described above, C.I. Pigment Yellow 139 is preferred.

Further, in the case of the colored composition for forming a blue pixel, as the blue colorant, for example, C.I. Pigment Blue 15:6, C.I. Pigment Violet 23, or the like can be used.

When a pigment is used as the colorant in the present invention, a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or the like may be used as needed to purify the pigment. In addition, the pigment may be modified by using a resin to modify the surface of the particle as needed. . For example, a vehicle resin described in JP-A-2001-108817 or a commercially available resin for dispersing various pigments is used as the resin for modifying the surface of the particles of the pigment. Further, the pigment is preferably used by refining the primary particles by a so-called salt mill. As a method of salt milling, for example, a method disclosed in Japanese Laid-Open Patent Publication No. Hei 08-179111 can be employed.

The content ratio of the (A) colorant is usually from 5 to 70% by mass, based on the total solid content of the coloring composition, from the viewpoint of forming a pixel having high luminance and excellent color purity or forming a black matrix having excellent light shielding properties. 5 to 60% by mass. The term "solid content" as used herein means a component other than the solvent described later.

If the content ratio of the coloring agent is increased, there is a tendency that the pixel pattern is liable to cause turbidity or water spots, but if the coloring composition of the present invention is used, even if the content ratio of the coloring agent is in the total solid content of the coloring composition When the amount is 30% by mass or more, turbidity or water spots can be suppressed. Further, the range of the content ratio of the coloring agent is preferably from 30 to 60% by mass based on the total solid content of the coloring composition.

When a pigment is used as the colorant in the present invention, it can be used together with a dispersing agent as needed. As the dispersing agent, for example, a suitable dispersing agent such as a cationic type, an anionic type or a nonionic type can be used, but a polymer dispersing agent is preferable. Specific examples thereof include a polyurethane dispersant, a polyethyleneimine dispersant, a polyoxyethylene alkyl ether dispersant, a polyoxyethylene alkylphenyl ether dispersant, and a polyethylene glycol. An alcohol diester dispersing agent, a sorbitan fatty acid ester dispersing agent, a polyester dispersing agent, an acrylic dispersing agent, and the like.

Such a dispersing agent can be obtained commercially, for example, as an acrylic dispersing agent, Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYL-LPN21116, BYK-LPN21324 (above, BYK), as a poly Examples of the urethane-based dispersing agent include Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above, BYK), SOLSPERSE 76500 (Lubrizol) SOSPERSE 24000 (manufactured by Lubrizol Co., Ltd.), and polyester dispersant, AJISPER PB821, AJISPER PB822, AJISPER PB880, AJISPER PB881 (Ajinomoto) FINE TECHNO Co., Ltd.). Further, the content of the dispersant can be appropriately determined within the range not inhibiting the object of the present invention.

- (B) Adhesive Resin -

The (B) binder resin in the present invention is not particularly limited, but is preferably a resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group. In order to enhance the effect required by the present invention, it is further preferred to use a polymer having an acidic functional group and a polymerizable unsaturated group.

The acid functional group may, for example, be a carboxyl group or a phenolic hydroxyl group. From the viewpoint of alkali solubility and storage stability of the obtained coloring composition, a carboxyl group is preferred.

In addition, examples of the polymerizable unsaturated group include a vinyl aryl group, a (meth) acryl fluorenyl group, and an allyl group. However, from the viewpoint of improving the required effect, (meth) acrylonitrile is preferred. base. Further, the polymer having an acidic functional group and a polymerizable unsaturated group preferably has an acid The side chain of the functional group-containing polymer has a polymerizable unsaturated group.

The polymer having an acidic functional group and a polymerizable unsaturated group is not particularly limited as long as it satisfies the above conditions, and examples thereof include (b-1) a polymerizable unsaturated compound having an epoxy group and a carboxyl group. a polymer obtained by reacting a carboxyl group of a polymer of a polymerizable unsaturated compound (hereinafter also referred to as "adhesive resin (b-1)"); (b-2) a polymerizable unsaturated compound having an isocyanate group, and a polymer obtained by reacting a hydroxyl group of a copolymer of a polymerizable unsaturated compound having a hydroxyl group and a polymerizable unsaturated compound having an acidic functional group (hereinafter also referred to as "binder resin (b-2)"); (b- 3) a polymer obtained by reacting a polymerizable unsaturated compound having a carboxyl group with an epoxy group of a polymer having a polymerizable unsaturated compound having an epoxy group, and further reacting an acid anhydride with a hydroxyl group formed by the reaction ( Hereinafter, it is also referred to as "adhesive resin (b-3)"); (b-4) reacting a polymerizable unsaturated compound having a carboxyl group with an epoxy group of an epoxy resin to further form an acid anhydride and a hydroxyl group formed by the reaction. Polymer obtained by reaction Also referred to as "adhesive resin (b-4)"); (b-5) reacting a polymerizable unsaturated compound having a hydroxyl group with a copolymer of styrene or a derivative thereof and maleic anhydride or an ester thereof Polymer (hereinafter also referred to as "adhesive resin (b-5)").

The polymer of the polymerizable unsaturated compound having a carboxyl group for producing the binder resin (b-1) is not particularly limited as long as it has a carboxyl group, and can be obtained by polymerizing a polymerizable unsaturated compound having a carboxyl group.

Examples of the polymerizable unsaturated compound having a carboxyl group include, in addition to (meth)acrylic acid and maleic acid, an unsaturated compound obtained by adding a lactone to (meth)acrylic acid (for example, ω-carboxyl group). Inside An ester mono(meth)acrylate); an unsaturated compound obtained by adding a dibasic acid such as succinic acid, maleic acid or phthalic acid or an acid anhydride thereof to a hydroxyalkyl (meth)acrylate (for example: 2) -(Meth)acryloxyethyl succinic acid) and the like. A variety of these compounds can be used.

Among them, preferred are (meth)acrylic acid, 2-(meth)acryloxyethyl succinic acid, ω-carboxypolycaprolactone mono(meth)acrylate, and further preferably (meth)acrylic acid. .

Examples of the polymerizable unsaturated compound having an epoxy group for producing the binder resin (b-1) include glycidyl (meth)acrylate, allyl glycidyl ether, and glycidyl-α. - Ethyl acrylate, crotonyl glycidyl ether, glycidyl (isobutenoate), N-(3,5-dimethyl-4-glycidyl)benzyl acrylamide, 4-hydroxybutyrate An unsaturated compound having a glycidyl group such as a (meth) acrylate glycidyl ether or a p-vinylbenzyl glycidyl ether; having a 2,3-epoxycyclopentyl group and a 3,4-epoxycyclohexyl group; An unsaturated compound of a polymerizable unsaturated group such as an alicyclic epoxy group such as a 3,8-epoxy group [tricyclo[5.2.1.0]indol-2-yl] or a (meth)acryl fluorenyl group. A variety of these compounds can also be used.

The copolymer of the polymerizable unsaturated compound having a hydroxyl group and the polymerizable unsaturated compound having an acidic functional group for producing the binder resin (b-2) is not particularly limited as long as it has a hydroxyl group and an acidic functional group, but may be A polymerizable unsaturated compound having at least a hydroxyl group is obtained by polymerizing a polymerizable unsaturated compound having an acidic functional group.

As the polymerizable unsaturated compound having a hydroxyl group and a vinyl group, in addition to 4-hydroxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, glycerol Mono (meth) acrylate, etc. Examples of the hydroxyalkyl methacrylate include N-methylol acrylamide and allyl alcohol. In addition, as the polymerizable unsaturated compound having an acidic functional group, a polymerizable unsaturated compound having a carboxyl group which is exemplified in the above-mentioned binder resin (b-1), and the like can be given. A variety of these compounds can also be used.

Examples of the polymerizable unsaturated compound having an isocyanate group for producing the binder resin (b-2) include 2-(meth)acryloxyethyl isocyanate and (meth)acrylic acid-2-( 2-Iocyanate ethoxy)ethyl ester, 1,1-(bisacryloxymethyl)ethyl isocyanate, and the like. A variety of these compounds can also be used.

The polymer of the polymerizable unsaturated compound having an epoxy group for producing the binder resin (b-3) may be a polymer having an epoxy group, and examples thereof include a poly(ethylene group) having an epoxy group. A methyl acrylate copolymer, a polystyrene copolymer having an epoxy group, and the like. The poly(meth)acrylate copolymer having an epoxy group is a copolymer of a (meth) acrylate having an epoxy group and another polymerizable unsaturated compound. Examples of the (meth) acrylate having an epoxy group include glycidyl (meth)acrylate, 3,4-butylene butyl (meth)acrylate, and (3,4-epoxy ring). Hexyl) methyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, and the like. A variety of these compounds can also be used.

Further, examples of the styrene having an epoxy group constituting the styrene copolymer having an epoxy group include o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, and vinyl. Styrene having 1 to 3 glycidyl groups such as benzyl glycidyl ether, 2,4-diglycidyloxymethylstyrene, 3,4,5-triglycidylmethylstyrene . A variety of these compounds can also be used.

Examples of the polymerizable unsaturated compound having a carboxyl group for producing the binder resin (b-3) include (meth)acrylic acid, ω-carboxypolycaprolactone mono(meth)acrylate, and 2-(A). Base) acryloylethyl succinic acid or the like. A variety of these compounds can also be used.

Examples of the acid anhydride for producing the binder resin (b-3) include malonic anhydride, maleic anhydride, citraconic anhydride, succinic anhydride, glutaric anhydride, glutaconic anhydride, itaconic anhydride, and diethylene glycol. A polybasic acid anhydride such as an acid anhydride, phthalic anhydride, cyclohexane-1,2-dicarboxylic anhydride, 4-cyclohexene-1,2-dicarboxylic anhydride or phthalic anhydride. A variety of these compounds can also be used.

Further, a polymer having a carboxyl group-containing polymerizable unsaturated compound for producing a binder resin (b-1), a polymerizable unsaturated compound having a hydroxyl group for producing a binder resin (b-2), and A copolymer of a polymerizable unsaturated polymer having an acidic functional group, and a polymer of a polymerizable unsaturated compound having an epoxy group for producing a binder resin (b-3), capable of copolymerization and polymerizability Other polymerizable unsaturated compounds in which the unsaturated compound is copolymerized.

Examples of the other polymerizable unsaturated compound include an N-position substituted maleimide such as N-phenylmaleimide or N-cyclohexylmaleimide; styrene, α- An aromatic vinyl compound such as methyl styrene, p-hydroxy-α-methylstyrene or vinyl naphthalene; methyl (meth)acrylate, n-butyl (meth)acrylate, or (meth)acrylic acid-2- Ethylhexyl ester, benzyl (meth)acrylate, cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, tricyclo[5.2.1.0 ^2,6 ]decane-8-yl (methyl Acrylate, dicyclopentenyl (meth)acrylate, 4-hydroxyphenyl (meth)acrylate, ethylene oxide modified (meth) acrylate such as p-anisyl (meth)acrylate Ester and the like. Further, polymerization of a polymerizable unsaturated compound having a carboxyl group for producing a polymer (b-1), and a polymerizable unsaturated compound having an epoxy group for producing a polymer (b-3) A polymerizable unsaturated compound having a hydroxyl group such as 2-hydroxyethyl (meth)acrylate or glycerol mono(meth)acrylate can be copolymerized. A variety of these compounds can also be used.

Examples of the epoxy resin used for the production of the binder resin (b-4) include a bisphenol A epoxy resin and a reaction of an alcoholic hydroxyl group of a bisphenol A epoxy resin with epichlorohydrin. Epoxy resin, bisphenol F type epoxy resin, epoxy resin obtained by reaction of alcoholic hydroxyl group of bisphenol F type epoxy resin with epichlorohydrin, bisphenol S type epoxy resin, biphenyl glycidol Ether, phenol novolak type epoxy resin, cresol novolak type epoxy resin, triglycidyl isocyanurate, trisphenol methane type epoxy resin, fluorene epoxy resin, alicyclic epoxy resin, two A cyclopentadiene type epoxy resin or the like. Further, a copolymer type epoxy resin can also be used.

The polymerizable unsaturated compound and the acid anhydride having a carboxyl group for producing the binder resin (b-4) include the same compounds as those used in the production of the above-mentioned binder resin (b-3).

As a copolymer of styrene or a derivative thereof for producing a binder resin (b-5) and maleic anhydride or an ester thereof, for example, styrene or m-methoxystyrene or p-methoxystyrene may be mentioned. And other styrene derivatives with maleic anhydride or monomethyl maleate, monoethyl maleate, mono-n-propyl maleate, monoisopropyl maleate, mono-n-butyl maleate, Malay Copolymer of maleic acid mono-lower alkyl ester such as monoisobutyl acrylate or mono-butyl butyl maleate.

Examples of the polymerizable unsaturated compound having a hydroxyl group for producing the binder resin (b-5) include hydroxyalkyl (meth)acrylate, N-methylol acrylamide, allyl alcohol and the like.

In the present invention, as the binder resin, a polymer having an acidic functional group and having no polymerizable unsaturated group can be used alone. For example, JP-A-7-140654, JP-A-H09-311444, JP-A-10-31308, JP-A-10-300922, and Japan The copolymer disclosed in JP-A-H11-174224, JP-A-H11-258415, JP-A-2000-56118, JP-A-2002-296778, and JP-A-2004-101728. It is of course also possible to use a polymer having an acidic functional group without a polymerizable unsaturated group together with a polymer having an acidic functional group and a polymerizable unsaturated group.

The acid value of the binder resin in the present invention is preferably from 10 to 200 KOH/mg, more preferably from 20 to 150 KOH/mg, still more preferably from 30 to 150 KOH/mg. Here, the acid value means the number of mg of KOH required to neutralize 1 g of the nonvolatile component of the solvent in which the polymer solution is removed.

The polystyrene-equivalent weight average molecular weight (Mw) of the binder resin in the present invention measured by GPC (eluent solvent: tetrahydrofuran) is usually from 1,000 to 100,000, preferably from 3,000 to 50,000. When the Mw is too small, the residual film ratio of the obtained film may be lowered, or the pattern shape, heat resistance, or the like may be impaired, or the electrical properties may be deteriorated. On the other hand, if the Mw is too large, the resolution may be lowered or the pattern shape may be impaired. Or it is easy to produce dry foreign matter when coated by a slit nozzle method.

In addition, the weight average molecular weight of the binder resin in the present invention The ratio (Mw/Mn) of the polystyrene-equivalent number average molecular weight (Mn) measured by GPC (eluent solvent: tetrahydrofuran) is preferably 1.0 to 5.0, more preferably 1.0 to 3.0.

The binder resin in the present invention can be produced by a known method, and can be disclosed, for example, in JP-A-2003-222717, JP-A-2006-259680, and International Publication No. 07/029871. The method to control its structure, Mw, Mw / Mn.

In the present invention, the binder resin can be used singly or in combination of two or more.

In the present invention, the content of the binder resin is preferably from 10 to 1,000 parts by mass, particularly preferably from 20 to 500 parts by mass, per 100 parts by mass of the (A) colorant. If the content of the binder resin is too small, for example, the alkali developability may be lowered, or the storage stability of the obtained colored composition may be lowered. On the other hand, if the amount is too large, the concentration of the colorant may be relatively lowered, so that it may be difficult to form a film. Achieve the target color density.

-(C) Photopolymerization Initiator -

The (C) photopolymerization initiator used in the present invention is a compound which can emit a compound having two or more polymerizable unsaturated bonds (D) which will be described later by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam or X-ray. Polymeric active species of the compound. The colored composition of the present invention is characterized by containing the compound represented by the above formula (1) as (C) a photopolymerization initiator.

In the above formula (1), examples of the alkyl group having 1 to 12 carbon atoms represented by R ¹ or R ⁴ include a methyl group, an ethyl group, a n-propyl group, an isopropyl group, an n-butyl group and a different form. Butyl, tert-butyl, n-pentyl, n-hexyl and the like. Further, examples of the alicyclic hydrocarbon group having 4 to 20 carbon atoms represented by R ¹ or R ⁴ include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a borneol group, a norbornyl group, and a diamond. Alkyl and the like. In the present invention, R ^{1 is} preferably an alkyl group having 1 to 6 carbon atoms or a phenyl group, and particularly preferably a methyl group or a phenyl group. Further, R ^{4 is} preferably an alkyl group having 1 to 6 carbon atoms or a phenyl group, and particularly preferably an ethyl group or a phenyl group.

In the above formula (1), examples of the alkylene group having 2 to 20 carbon atoms represented by R ² include an exoethyl group, a propyl group, a butyl group, a pentyl group, and a hexyl group. In the present invention, R ^{2 is} preferably a methylene group or an alkylene group having 2 to 5 carbon atoms, particularly preferably a methylene group or an ethyl group.

In the above formula (1), examples of the alicyclic hydrocarbon group having 3 to 20 carbon atoms represented by R ³ include a cycloalkyl group having 3 to 8 carbon atoms, a borneol group, a norbornyl group, and a diamond. Alkyl and the like. In the present invention, R ^{3 is} preferably a cycloalkyl group having 3 to 8 carbon atoms, particularly preferably a cyclopentyl group or a cyclohexyl group.

In the above formula (1), R ^{5 is} preferably a tolyl group or a naphthyl group.

In the above formula (1), examples of the alkyl group having 1 to 12 carbon atoms which are a substituent represented by R ¹ or R ⁴ or a substituent of R ⁵ include methyl group, ethyl group and n-propyl group. Base, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and the like. The alkoxy group having 1 to 12 carbon atoms and having a substituent represented by R ¹ or R ⁴ or a substituent of R ⁵ may, for example, be a methoxy group, an ethoxy group or a propoxy group.

The photopolymerization initiator represented by the above formula (1) may, for example, be a compound represented by the following formulas (C-1) to (C-10).

In the present invention, the photopolymerization initiator represented by the above formula (1) can be used singly or in combination of two or more kinds.

In the present invention, other photopolymerization initiators can be used in combination with the photopolymerization initiator represented by the above formula (1). Examples of such a photopolymerization initiator include a thioxanthone photopolymerization initiator, an acetophenone photopolymerization initiator, a biimidazole photopolymerization initiator, and the like. A photopolymerization initiator, an O-fluorenyl-based photopolymerization initiator other than the above formula (1), a sulfonium-based photopolymerization initiator, a benzoin-based photopolymerization initiator, and a benzophenone-based photopolymerization initiator An α-diketone photopolymerization initiator, a polycyclic fluorene-based photopolymerization initiator, a diazo-based photopolymerization initiator, and a sulfhydrazine sulfonate-based photopolymerization initiator.

Among them, a thioxanthone photopolymerization initiator, an acetophenone photopolymerization initiator, a biimidazole photopolymerization initiator, and the like are preferable. The photopolymerization initiator or the O-fluorenyl fluorene-based photopolymerization initiator other than the above formula (1) is particularly preferably a biimidazole-based photopolymerization initiator from the viewpoint of improving the desired effect.

In the present invention, other photopolymerization initiators may be used singly or in combination of two or more.

Among the other photopolymerization initiators, specific examples of the thioxanthone-based photopolymerization initiator include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, and 2-isopropylthioxene. Ketone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropyl Ketyl ketone and the like.

Further, specific examples of the acetophenone-based photopolymerization initiator include 2-methyl-1-[4-(methylthio)phenyl]-2- Lolinylpropan-1-one, 2-benzyl-2-dimethylamino-1-(4- Polinylphenyl)butan-1-one, 2-(4-methylbenzyl)-2-(dimethylamino)-1-(4- Polinylphenyl)butan-1-one and the like.

Further, specific examples of the biimidazole-based photopolymerization initiator include 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'. -biimidazole, 2,2'-bis(2,4-dichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis ( 2,4,6-Trichlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole.

In addition, as the above three Specific examples of the photopolymerization initiator include 2,4,6-tris(trichloromethyl) symmetry III. 2-methyl-4,6-bis(trichloromethyl) symmetry three , 2-[2-(5-methylfuran-2-yl)vinyl]-4,6-bis(trichloromethyl) symmetric three 2-[2-(furan-2-yl)vinyl]-4,6-bis(trichloromethyl) symmetric three 2-[2-(4-Diethylamino-2-methylphenyl)vinyl]-4,6-bis(trichloromethyl)symmetric three 2-[2-(3,4-Dimethoxyphenyl)vinyl]-4,6-bis(trichloromethyl)symmetric three 2-(4-methoxyphenyl)-4,6-bis(trichloromethyl) symmetry three 2-(4-ethoxystyryl)-4,6-bis(trichloromethyl)symmetric three 2-(4-n-butoxyphenyl)-4,6-bis(trichloromethyl)symmetric three Three with a halogenated methyl group a compound.

In addition, specific examples of the O-fluorenyl fluorene-based photopolymerization initiator other than the above formula (1) include 1,2-octanedione-1-[4-(phenylthio)phenyl]-2 -(O-benzhydrazide), ethyl ketone-1-[9-ethyl-6-(2-methylbenzhydryl)-9H-indazol-3-yl]-1-(O-B醯肟), Ethyl Ketone-1-[9-Ethyl-6-(2-methyl-4-tetrahydrofurylmethoxybenzylidene)-9H-indazol-3-yl]-1-(O -acetamidine), ethyl ketone-1-[9-ethyl-6-{2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzene Mercapto}-9H-carbazol-3-yl]-1-(O-acetamidine) and the like. As a commercial item of the O-mercapto oxime compound, NCI-831, NCI-930 (above, ADEKA Co., Ltd.), etc. can also be used.

In the present invention, a sensitizer can also be used in combination with the above photopolymerization initiator. Examples of such a sensitizer include 4,4′-bis(dimethylamino)benzophenone, 4,4′-bis(diethylamino)benzophenone, and 4-diethylamine. Acetophenone, 4-dimethylaminopropiophenone, ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis(4-di Ethylaminobenzyl)cyclohexanone, 7-diethylamino-3-(4-diethylaminobenzimidyl)coumarin, 4-(diethylamino)chalcone, and the like.

In the present invention, the content of the photopolymerization initiator represented by the above formula (1) is preferably from 1 to 20 parts by mass, more preferably from 3 to 20 parts by mass, per 100 parts by mass of the compound having two or more polymerizable unsaturated bonds as described later (D). ~10 parts by mass. In this case, if the content of the photopolymerization initiator represented by the above formula (1) is too small, the desired effect may not be sufficiently obtained. On the other hand, if it is too large, the brightness and the solubility of the developer become easy. Reduced trend.

In addition, when the photopolymerization initiator represented by the above formula (1) is used in combination with another photopolymerization initiator, the content of the other photopolymerization initiator is preferably 10 parts by mass based on 100 parts by mass of the photopolymerization initiator represented by the above formula (1). ~300 parts by mass, particularly preferably 20 to 150 parts by mass.

- (D) a compound having two or more polymerizable unsaturated bonds -

The compound having two or more polymerizable unsaturated bonds in (D) in the invention is not particularly limited, but is preferably a compound having two or more (meth) acrylonitrile groups.

Examples of the compound having two or more (meth) acryloyl fluorenyl groups include polyfunctional (meth) acrylate obtained by reacting an aliphatic polyhydroxy compound with (meth)acrylic acid, and modified by caprolactone. Multifunctional a acrylate, an alkylene oxide-modified polyfunctional (meth) acrylate, a polyfunctional urethane (methyl) obtained by reacting a (meth) acrylate having a hydroxyl group with a polyfunctional isocyanate An acrylate, a polyfunctional (meth) acrylate having a carboxyl group obtained by reacting a (meth) acrylate having a hydroxyl group and an acid anhydride, or the like.

Here, examples of the aliphatic polyhydroxy compound include a divalent aliphatic polyhydroxy compound such as ethylene glycol, propylene glycol, polyethylene glycol, or polypropylene glycol; for example, glycerin, trimethylolpropane, and pentaerythritol. An aliphatic polyhydroxy compound having 3 or more yuan of dipentaerythritol. Examples of the (meth) acrylate having a hydroxyl group include 2-hydroxyethyl (meth)acrylate, trimethylolpropane di(meth)acrylate, and pentaerythritol tri(meth)acrylate. Dipentaerythritol penta (meth) acrylate, glycerol dimethacrylate, and the like. Examples of the polyfunctional isocyanate include toluene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, and isophorone diisocyanate. Examples of the acid anhydride include an acid anhydride such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, and hexahydrophthalic anhydride, such as pyromellitic dianhydride. And a tetrabasic acid dianhydride of biphenyltetracarboxylic dianhydride and benzophenone tetracarboxylic dianhydride.

In addition, the compound described in paragraphs [0015] to [0018] of JP-A-11-44955 is exemplified as the above-mentioned caprolactone-modified polyfunctional (meth) acrylate. The above-mentioned alkylene oxide-modified polyfunctional (meth) acrylate may be exemplified by at least one modified from ethylene oxide selected from bisphenol A and propylene oxide of bisphenol A. Methyl) acrylate, ethylene oxide selected from iso-cyanuric acid and iso-cyanuric acid At least one modified tri(meth)acrylate of propylene oxide, at least one modified from ethylene oxide selected from trimethylolpropane and propylene oxide of trimethylolpropane a tri(meth) acrylate, a tri(meth) acrylate modified with at least one selected from the group consisting of ethylene oxide selected from pentaerythritol and propylene oxide of pentaerythritol, ethylene oxide selected from pentaerythritol, and At least one modified tetra(meth)acrylate of pentylene oxide of pentaerythritol, at least one modified with at least one selected from ethylene oxide selected from dipentaerythritol and propylene oxide of dipentaerythritol An acrylate, a hexa(meth)acrylate modified with at least one selected from the group consisting of ethylene oxide of dipentaerythritol and propylene oxide of dipentaerythritol.

Among them, a polyfunctional (meth) acrylate obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth)acrylic acid, and a caprolactone-modified polyfunctional (meth)acrylic acid are preferred. Ester, polyfunctional urethane (meth) acrylate, polyfunctional (meth) acrylate having a carboxyl group. The strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and it is difficult to cause scum, residual film, etc. on the substrate of the unexposed portion and the light shielding layer, and the aliphatic polyhydroxy compound of 3 or more elements is Among the polyfunctional (meth) acrylates obtained by the reaction of (meth)acrylic acid, particularly preferred are trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, and dipentaerythritol hexaacrylate. Among the polyfunctional (meth) acrylates of a carboxyl group, a compound obtained by reacting pentaerythritol triacrylate with succinic anhydride, and a compound obtained by reacting dipentaerythritol pentaacrylate with succinic anhydride are particularly preferred.

In the present invention, (D) a compound having two or more polymerizable unsaturated bonds can be used singly or in combination of two or more.

The content of the compound (D) having two or more polymerizable unsaturated bonds in the present invention is preferably from 50 to 300 parts by mass, particularly preferably from 90 to 200 parts by mass, per 100 parts by mass of the (B) binder resin. In this case, if the content of the compound having two or more polymerizable unsaturated bonds is too small, the pixel tends to be turbid or watery. On the other hand, when the content of the compound having two or more polymerizable unsaturated bonds is too large, when the alkali developability is imparted to the colored composition of the present invention, the alkali developability is lowered, and the substrate is not exposed on the unexposed portion. There is a tendency that scum, residual film, and the like are likely to occur on the layer.

-(E) polyfunctional thiols -

The colored composition of the present invention is characterized by containing (E) a polyfunctional thiol, that is, a compound having two or more sulfanyl groups (-SH). By using a polyfunctional thiol in combination with the photopolymerization initiator represented by the above formula (1), it is possible to suppress turbidity of the pixel pattern or generation of water spots, and it is possible to suppress a decrease in luminance or a generation of foreign matter accompanying the high-temperature heating step.

The polyfunctional thiol is not particularly limited as long as it is a compound having two or more sulfanyl groups, and examples thereof include a hydrocarbon having two or more sulfanyl groups as a substituent, and a poly(mercaptoacetate) of a polyhydric alcohol. ), poly (3-mercaptopropionate) of polyhydric alcohol, poly(2-mercaptopropionate) of polyhydric alcohol, poly(3-mercaptobutyrate) of polyhydric alcohol, having two or more sulfur A heterocyclic group having an alkyl group as a substituent, a polyoxyalkylene having two or more sulfanyl groups, and the like.

Specific examples of the hydrocarbon having two or more sulfanyl groups as a substituent include 1,6-hexanedithiol, 1,10-decanedithiol, and 1,4-benzenedithiol. , 4-bis(decylmethyl)benzene, and the like.

Specific examples of the poly(mercaptoacetate) of the above-mentioned polyol include ethylene glycol bis(mercaptoacetate), propylene glycol bis(mercaptoacetate), glycerol tris(mercaptoacetate), and three Methylolpropane tris(mercaptoacetate), pentaerythritol tetrakis(mercaptoacetate), dipentaerythritol hexa(mercaptoacetate), and the like.

Specific examples of the poly(3-mercaptopropionate) of the above-mentioned polyol include ethylene glycol bis(3-mercaptopropionate), propylene glycol bis(3-mercaptopropionate), and glycerol tris(3). - mercaptopropionate), trimethylolpropane tris(3-mercaptopropionate), pentaerythritol tetrakis(3-mercaptopropionate), dipentaerythritol hexa(3-mercaptopropionate), and the like.

Specific examples of the poly(2-mercaptopropionate) of the above-mentioned polyol include ethylene glycol bis(2-mercaptopropionate), propylene glycol bis(2-mercaptopropionate), and diethylene glycol. Bis(2-mercaptopropionate), butanediol bis(2-mercaptopropionate), octanediol bis(2-mercaptopropionate), trimethylolpropane tris(2-mercaptopropionate) Pentaerythritol tetrakis(2-mercaptopropionate), dipentaerythritol hexakis(2-mercaptopropionate), and the like.

Specific examples of the poly(3-mercaptobutyrate) of the above-mentioned polyol include ethylene glycol bis(3-mercaptobutyrate), diethylene glycol bis(3-mercaptobutyrate), and butyl. Diol bis(3-mercaptobutyrate), trimethylolpropane tris(3-mercaptobutyrate), pentaerythritol tetrakis(3-mercaptobutyrate), dipentaerythritol hexa(3-mercaptobutyrate), Ethylene glycol bis(3-mercaptoisobutyrate), diethylene glycol bis(3-mercaptoisobutyrate), butanediol bis(3-mercaptoisobutyrate), trimethylolpropane tri 3-mercaptoisobutyrate), pentaerythritol tetrakis(3-mercaptoisobutyrate), dipentaerythritol hexa(3-mercaptoisobutyrate), octanediol bis(3-mercaptobutyrate), octanediol Bis(3-mercaptoisobutyrate) and the like.

Specific examples of the heterocyclic ring having two or more sulfanyl groups as a substituent include 2,4,6-trimethyl symmetrical three. , 2-(N,N-dibutylamino)-4,6-diindenyl symmetrical three And 2-mercapto-5-substituted thiadiazole described in JP-A-2-153353.

The polyoxyalkylene having two or more sulfanyl groups may, for example, be a polyoxyalkylene obtained by hydrolyzing and condensing a decane compound having a sulfanyl group and a hydrolyzable group. The specific description and the manufacturing method are described in Japanese Laid-Open Patent Publication No. 2008-242078, Japanese Patent Application Laid-Open No. 2011-128239, and the like. Further, a sesquioxane having two or more sulfanyl groups can be, for example, commercially available from Arakawa Chemical Industries Co., Ltd. as a COMPOCERAN SQ series.

Among these polyfunctional thiols, poly(mercaptoacetate) of polyhydric alcohol, poly(3-mercaptopropionate) of polyhydric alcohol, and polyhydric alcohol are preferable from the viewpoint of further improving the required effect. (2-mercaptopropionate), poly(3-mercaptobutyrate) of polyhydric alcohol, polyoxyalkylene having two or more sulfalkyl groups.

In the present invention, the (E) polyfunctional thiol can be used singly or in combination of two or more.

In the present invention, the content of the (E) polyfunctional thiol is preferably from 5 to 200 parts by mass, particularly preferably from 10 to 100 parts by mass, per 100 parts by mass of the photopolymerization initiator represented by the above formula (1). In this case, if the content of the (E) polyfunctional thiol is too small, there is a possibility that the desired effect cannot be obtained. On the other hand, if it is too much, there is a possibility that the pattern shape becomes a drape shape.

-(F) solvent -

The colored composition of the present invention contains the above components (A) to (E) and any other components which can be added, and is usually prepared by mixing a solvent to prepare a liquid composition.

The solvent is appropriately selected and used as long as it dissolves or dissolves the components (A) to (E) constituting the colored composition or other components and does not react with these components and has moderate volatility.

Examples of such a solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, and diethylene glycol monomethyl. Ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol Monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-n-butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol single (poly) olefinic diol monoalkyl ethers such as n-butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol monoethyl ether; alkyl lactate such as methyl lactate or ethyl lactate; methanol, ethanol, and c Alcohol, butanol, isopropanol, isobutanol, tertiary butanol, octanol, 2-ethylhexanol, cyclohexanol, etc. (cyclo)alkyl alcohols; ketone alcohols such as diacetone alcohol; Alcohol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether Acid ester, (poly)olefin group such as diol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, acetic acid-3-methoxybutyl ester, acetic acid-3-methyl-3-methoxybutyl ester Glycol monoalkyl ether acetate; diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene Other ethers such as alcohol diethyl ether and tetrahydrofuran; ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone and 3-heptanone; propylene glycol diacetate and 1,3-butylene glycol Diacetate such as acetate or 1,6-hexanediol diacetate; methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate , alkoxycarboxylates such as ethyl 3-ethoxypropionate, ethyl ethoxyacetate, 3-methyl-3-methoxybutylpropionate; ethyl acetate, n-propyl acetate , isopropyl acetate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, butyl Other esters such as n-butyl acrylate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetate, ethyl acetate, ethyl 2-oxobutyrate; toluene, xylene Other aromatic hydrocarbons; decylamines such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone or indoleamines.

Among these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, and propylene glycol monomethyl are preferable from the viewpoints of solubility, pigment dispersibility, coatability, and the like. Ether acetate, propylene glycol monoethyl ether acetate, acetic acid-3-methoxybutyl ester, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-glycol Ketone, 3-heptanone, 1,3-butanediol diacetate, 1,6-hexanediol diacetate, ethyl lactate, ethyl 3-methoxypropionate, 3-ethoxyl Methyl propionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutylpropionate, n-butyl acetate, isobutyl acetate, n-amyl formate, isoamyl acetate , n-butyl propionate, ethyl butyrate, isopropyl butyrate, n-butyl butyrate, ethyl pyruvate and the like.

In the present invention, the solvent can be used singly or in combination of two or more.

The content of the solvent is not particularly limited, and the total concentration of each component of the solvent from which the coloring composition is removed is preferably from 5 to 50% by mass, from the viewpoint of coating properties and stability of the obtained coloring composition. It is particularly good in an amount of 10 to 40% by mass.

-additive-

The colored composition of the present invention may further contain various additives as needed.

Examples of the additive include a filler such as glass or alumina; a polymer compound such as polyvinyl alcohol or poly(fluoroalkyl acrylate); a surfactant such as a fluorine-based surfactant or a lanthanoid surfactant; and ethylene. Trimethoxy decane, vinyl triethoxy decane, vinyl tris(2-methoxyethoxy) decane, N-(2-aminoethyl)-3-aminopropylmethyl dimethyl Oxydecane, N-(2-aminoethyl)-3-aminopropyltrimethoxydecane, 3-aminopropyltriethoxydecane, 3-glycidoxypropyltrimethoxy Decane, 3-glycidoxypropylmethyldimethoxydecane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxydecane, 3-chloropropylmethyldimethoxydecane , adhesion promoters such as 3-chloropropyltrimethoxydecane, 3-methylpropenyloxypropyltrimethoxydecane, 3-mercaptopropyltrimethoxydecane; 2,2-thiobis (4 -methyl-6-tertiary butyl phenol), 2,6-ditributyl phenol, pentaerythritol tetrakis[3-(3,5-ditributyl-4-hydroxyphenyl)propionate] And other antioxidants; 2-(3-tert-butyl-5-methyl-2-hydroxyphenyl)-5-chlorobenzotriazole, alkoxy Benzophenone ultraviolet absorbers; Deflocculants such as sodium polyacrylate; malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric Horse acid, mesaconic acid, 2-aminoethanol, 3-amino-1-propanol, 5-amino-1-pentanol, 3-amino-1,2-propanediol, 2-amino-1 , 3-propanediol, 4-amino-1,2-butanediol and other residue improvers; succinic acid mono [2-(methyl) propylene methoxyethyl] ester, phthalic acid mono [2- ( A developability improving agent such as methyl propylene oxy oxyethyl ester or ω-carboxy polycaprolactone mono (meth) acrylate.

The colored composition of the present invention can be produced by a suitable method, and can be produced, for example, by mixing the components (A) to (E) with (F) a solvent or any other component added arbitrarily. When a pigment is used as the (A) coloring agent, a method of preparing a pigment by using, for example, a bead mill, a roll mill or the like in a solvent (F) in the presence of a dispersing agent is preferred. A part of the component (B) used in the case is pulverized and mixed and dispersed to prepare a pigment dispersion liquid, and then the components (B) to (E) and the solvent or other components further added as needed are added to the pigment dispersion liquid and mixed.

Color filter and manufacturing method thereof

The color filter of the present invention comprises a coloring layer formed using the coloring composition of the present invention.

As a method of manufacturing a color filter, the following method can be mentioned first. First, on the surface of the substrate, a light shielding layer (black matrix) is formed in such a manner as to divide the portion where the pixels are formed. Next, a liquid composition of the radiation sensitive composition of the present invention containing, for example, a red coloring agent is applied onto the substrate, and then prebaked to evaporate the solvent to form a coating film. Next, after exposing the coating film through a photomask, development is carried out using an alkaline developing solution to dissolve and remove the unexposed portion of the coating film. Thereafter, by post-baking, a red pixel pattern is formed to define a pixel array arranged in an array.

Next, using the green or blue colored radiation-sensitive linear composition, the coating, prebaking, exposure, development, and post-baking of each coloring radiation composition are performed in the same manner as described above, sequentially on the same substrate. A green pixel array and a blue pixel array are formed. Thereby, a color filter in which a pixel array of three primary colors of red, green, and blue is disposed on the substrate is obtained. However, in the present invention, the order in which the pixels of the respective colors are formed is not limited to the above order. Further, in the first method of manufacturing a color filter, any one or more of the red, green, and blue pixel arrays may be a coloring layer formed using the coloring composition of the present invention.

Further, the black matrix can be formed by forming a metal film such as chromium formed by sputtering or vapor deposition into a desired pattern by photolithography, and a coloring radiation-containing linear composition containing a black colorant can also be used. The case of pixel formation is similarly formed. The colored composition of the present invention can also be suitably used to form the black matrix.

Examples of the substrate used in forming the color filter include glass, ruthenium, polycarbonate, polyester, aromatic polyamide, polyamidimide, and polyimine.

Further, for these substrates, an appropriate pretreatment such as pharmaceutical treatment, plasma treatment, ion plating, sputtering, gas phase reaction method, or vacuum vapor deposition using a decane coupling agent or the like may be performed as needed.

When the coloring sensitizing radiation composition is applied onto a substrate, an appropriate coating method such as a spray coating method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, or a bar coating method may be employed. In order to adopt a spin coating method or a slit die coating method.

Prebaking is usually carried out by combining vacuum drying and heat drying. stress reliever Drying usually proceeds to 50~200Pa. In addition, the conditions of heat drying are usually 70 to 110 ° C for about 1 to 10 minutes.

The coating thickness is usually 0.6 to 8 μm, preferably 1.2 to 5 μm, in terms of the film thickness after drying.

Examples of the light source used for forming the pixel and/or the black matrix include a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, and a low pressure mercury lamp. Or argon ion laser, YAG laser, XeCl excimer laser, nitrogen laser and other laser light sources. As the exposure light source, an ultraviolet LED can also be used. Radiation having a wavelength in the range of 190 to 450 nm is preferred.

The exposure amount of the radiation is generally preferably from 10 to 10000 J/m ² . Generally, the lower the amount of exposure, the more likely the turbidity or water spots are generated in the pixel pattern. However, when the coloring composition of the present invention is used, even if the exposure amount is 800 J/m ² or less, and further 600 J/m ² or less, turbidity is hard to occur. Or water spots.

Further, as the above alkaline developing solution, for example, sodium carbonate, sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline or 1,8-diazabicyclo[5.4.0 is preferred. An aqueous solution of -7-undecene and 1,5-diazabicyclo[4.3.0]-5-decene.

In the above alkaline developing solution, a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added in an appropriate amount. Also, it is usually washed with water after alkaline development.

As the development treatment method, a shower development method, a spray development method, a dip development method, a paddle type development method, or the like can be applied. The developing conditions are preferably 5 to 300 seconds at normal temperature.

Post-baking conditions are usually 10~60 minutes at 120~280°C. right. When the temperature of the post-baking becomes high, the brightness may be lowered due to the type of the pigment to be used, or foreign matter may be generated in the pixel pattern. However, if the colored composition of the present invention is used, the temperature is 200 ° C or higher and further 220 ° C or higher. The post-baking temperature can also suppress the problem.

The film thickness of the pixel thus formed is usually 0.5 to 5 μm, preferably 1 to 3 μm.

In addition, as a second method of producing a color filter, a method of obtaining pixels of respective colors by an inkjet method disclosed in Japanese Laid-Open Patent Publication No. Hei. No. Hei. In this method, first, a partition wall which also has a light blocking function is formed on the surface of the substrate. Next, a liquid composition of the thermosetting composition of the present invention containing, for example, a red coloring agent is ejected into the partition walls formed by an inkjet device, and then prebaked to evaporate the solvent. Next, the coating film is exposed as needed, and then post-baked to be cured to form a red pixel pattern.

Next, using the green or blue colored composition, a green pixel pattern and a blue pixel pattern are sequentially formed on the same substrate in the same manner as described above. Thereby, a color filter in which pixel patterns of three primary colors of red, green, and blue are arranged on the substrate is obtained. However, in the present invention, the order in which the pixels of the respective colors are formed is not limited to the above order. Further, in the second method of manufacturing the color filter, any one or more of the red, green, and blue pixel arrays may be a coloring layer formed using the coloring composition of the present invention.

Further, the partition wall not only realizes a light-shielding function, but also realizes a function of not color-mixing the coloring compositions discharged into the divided regions, and thus the film The thickness is thicker than the black matrix used in the first method described above. Therefore, the partition walls are usually formed using a black sensitizing radioactive composition.

The substrate used for forming the color filter, the light source of the radiation, and the method and conditions of the prebaking or postbaking are the same as those of the first method described above. The film thickness of the pixel formed by the inkjet method is the same as the height of the partition wall.

On the pixel pattern thus obtained, a protective film is formed as needed, and then a transparent conductive film is formed by sputtering. After the transparent conductive film is formed, a spacer may be further formed to form a color filter. The spacer is usually formed using a radiation-sensitive composition, and a spacer having a light-shielding property (black spacer) can also be formed. In this case, the colored composition of the present invention can also be suitably used to form the black spacer by using a color-sensitive radiation composition containing a black colorant.

The color filter of the present invention thus obtained is extremely high in brightness, and thus is extremely useful for a color liquid crystal display element, a color image pickup tube element, a color sensor, an organic EL display element, an electronic paper, and the like.

Display component

The display element of the present invention includes the color filter of the present invention. Examples of the display element include a color liquid crystal display element, an organic EL display element, and electronic paper.

The color liquid crystal display element having the color filter of the present invention may be of a transmissive type or a reflective type, and an appropriate structure may be employed. For example, a color filter may be formed on a substrate different from a driving substrate on which a thin film transistor (TFT) is disposed, and the driving substrate and the substrate on which the color filter is formed may be disposed to face each other via a liquid crystal layer; and also A structure in which a color filter is formed on a surface of a driving substrate on which a thin film transistor (TFT) is disposed, and an ITO (tin-doped indium oxide) electrode or IZO (indium oxide and zinc oxide) may be employed. The mixture of the electrodes is disposed opposite to each other across the liquid crystal layer. The structure of the latter can significantly increase the aperture ratio, and has the advantage of obtaining a bright and high-definition liquid crystal display element.

The color liquid crystal display element including the color filter of the present invention may include a backlight unit using a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As the white LED, for example, a white LED in which a red LED, a green LED, and a blue LED are combined to obtain white light by color mixing; a blue LED, a red LED, and a green phosphor are combined to obtain white light by color mixing. a white LED; a white LED that combines a blue LED, a red illuminating phosphor, and a green illuminating phosphor to obtain a white light by color mixing; and a white light by a color mixture of a blue LED and a YAG-based phosphor a white LED; a white LED that combines a blue LED, an orange illuminating phosphor, and a green illuminating phosphor to obtain a white light by mixing colors; an ultraviolet LED, a red luminescent phosphor, a green luminescent phosphor, and a blue illuminating The phosphor combines to obtain a white light white LED or the like by color mixing.

In the color liquid crystal display device including the color filter of the present invention, TN (Twisted Nematic) type, STN (Super Twisted Nematic) type, and IPS (In-Planes Switching type) can be applied. A suitable liquid crystal mode such as an internal electric field switching type, a VA (Vertical Alignment) type, or an OCB (Optically Compensated Birefringence) type.

In addition, the organic EL display element having the color filter of the present invention may have a suitable structure, and a structure disclosed in Japanese Laid-Open Patent Publication No. Hei 11-307242, for example.

In addition, the electronic paper including the color filter of the present invention may have a suitable structure, and a structure disclosed in Japanese Laid-Open Patent Publication No. 2007-41169, for example.

[Examples]

Hereinafter, embodiments of the present invention will be described more specifically by way of examples. However, the invention is not limited to the following examples.

<Synthesis of binder resin> Synthesis Example 1

In a flask equipped with a cooling tube and a stirrer, 100 parts by mass of propylene glycol monomethyl ether acetate was added and replaced with nitrogen. Heating to 80 ° C, adding 50 parts by mass of propylene glycol monomethyl ether acetate, 15 parts by mass of methacrylic acid, 3 parts by mass of styrene, and 5 mass of 2-hydroxyethyl methacrylate at the same temperature for 1 hour. Parts, 19 parts by mass of methyl methacrylate, 26 parts by mass of cyclohexyl methacrylate, 12 parts by mass of N-phenylmaleimide, and mono(2-methylpropenyloxyethyl) succinate 20 parts by mass and 6 parts by mass of 2,2'-azobis(2,4-dimethylvaleronitrile) were mixed and maintained at this temperature for 2 hours. Thereafter, the temperature of the reaction solution was raised to 90 ° C, and further polymerization was carried out for 1 hour, whereby a binder resin solution was obtained. The obtained binder resin Mw = 12,000, Mn = 7000, and solid content concentration = 40% by mass. The binder resin is "adhesive resin (B-1)".

Synthesis Example 2

In a flask equipped with a cooling tube and a stirrer, 100 parts by mass is added Propylene glycol monomethyl ether acetate was replaced with nitrogen. Heating to 80 ° C, 50 parts by mass of propylene glycol monomethyl ether acetate, 15 parts by mass of methacrylic acid, 12 parts by mass of styrene, 41 parts by mass of benzyl methacrylate, methacrylic acid-2- at the same temperature 15 parts by mass of hydroxyethyl ester, 2 parts by mass of n-butyl methacrylate, 15 parts by mass of N-phenylmaleimide, 0.5 parts by mass of 2,2'-azobisbutyronitrile, and pentaerythritol tetrakis(3-mercapto) Propionate) 2 parts by mass of the mixed solution was kept at 80 ° C for 4 hours. Thereafter, the temperature of the reaction solution was raised to 100 ° C, and further polymerization was carried out for 1 hour, whereby a binder resin solution (solid content concentration = 40% by mass) was obtained. The obtained binder resin Mw = 24000, Mn = 14800, and solid content concentration = 40% by mass. The binder resin is "binder resin (B-2)".

Synthesis Example 3

In a flask equipped with a cooling tube and a stirrer, 44 parts by mass of p-vinylbenzyl glycidyl ether, 40 parts by mass of N-phenylmaleimide, and 16 parts by mass of benzyl methacrylate were dissolved in propylene glycol monomethyl group. To 300 parts by mass of the ether acetate, 8.0 parts by mass of 2,2'-azobisisobutyronitrile and 8.0 parts by mass of α-methylstyrene dimer were further added, followed by nitrogen purge for 15 minutes. After the nitrogen purge, the reaction solution was stirred and heated to 80 ° C for 5 hours while bubbling with nitrogen.

Next, 17 parts by mass of methacrylic acid, 0.5 parts by mass of p-methoxyphenol and 4.4 parts by mass of tetrabutylammonium bromide were added to the reaction solution, and the mixture was reacted at 120 ° C for 9 hours. Further, 18.5 parts by mass of succinic anhydride was added, and after reacting at 100 ° C for 6 hours, the liquid temperature was maintained at 85 ° C for 2 times, and concentrated under reduced pressure to obtain a binder resin containing 40% by mass (B- 3) solution. The Mw of the binder resin (B-3) was 7,800.

<Preparation of Pigment Dispersion> Preparation Example 1

15 parts by mass of CI Pigment Green 58/CI Pigment Yellow 150/CI Pigment Yellow Y138=52/36/12 (mass ratio) mixture was used as (A) colorant, 11 parts by mass (solid content concentration = 40% by mass) BYK-LPN21116 (manufactured by BYK Co., Ltd.) as a dispersing agent, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, and mixed and dispersed by a bead mill. Thus, a pigment dispersion liquid (A-1) was produced.

Preparation Example 2

15 parts by mass of CI Pigment Green 58/CI Pigment Yellow Y138=47/53 (mass ratio) mixture was used as (A) colorant, and 11 parts by mass (solid content concentration = 40% by mass) of BYK-LPN21116 (manufactured by BYK Corporation) As a dispersing agent, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, the mixture was mixed and dispersed by a bead mill to prepare a pigment dispersion liquid ( A-2).

Preparation Example 3

15 parts by mass of a mixture of CI Pigment Red 254/CI Pigment Red 177/CI Pigment Yellow 150=23/70/7 (mass ratio) was used as (A) colorant, 11 parts by mass (solid content concentration = 40% by mass) BYK-LPN21116 (manufactured by BYK Co., Ltd.) as a dispersing agent, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, and mixed and dispersed by a bead mill. Thus, a pigment dispersion liquid (A-3) was produced.

Preparation Example 4

15 parts by mass of C.I. Pigment Red 254/C.I. Pigment Red 177/C.I. Pigment Yellow 139=15/77/8 (mass ratio) mixture was used as (A) colorant, 11 quality BYK-LPN21116 (manufactured by BYK Co., Ltd.) as a dispersing agent, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a dispersing agent (solid content concentration = 40% by mass) The solvent was mixed and dispersed by a bead mill to prepare a pigment dispersion liquid (A-4).

Preparation Example 5

15 parts by mass of CI Pigment Red 242/CI Pigment Red 177/CI Pigment Yellow 150=22/72/6 (mass ratio) mixture was used as (A) colorant, 11 parts by mass (solid content concentration = 40% by mass) BYK-LPN 21116 (manufactured by BYK Co., Ltd.) as a dispersant, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, and mixed and dispersed by a bead mill Thus, a pigment dispersion liquid (A-5) was produced.

Preparation Example 6

15 parts by mass of CI Pigment Red 254/CI Pigment Red 177=55/45 (mass ratio) mixture was used as (A) colorant, and 11 parts by mass (solid content concentration = 40% by mass) of BYK-LPN21116 (manufactured by BYK Corporation) As a dispersing agent, 14 parts by mass of a binder resin (B-1) solution, and 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, the mixture was mixed and dispersed by a bead mill to prepare a pigment dispersion liquid ( A-6).

Preparation Example 7

15 parts by mass of CI Pigment Blue 15:6/CI Pigment Violet 23=83/17 (mass ratio) mixture was used as (A) colorant, and 11 parts by mass (solid content concentration = 40% by mass) of BYK-LPN21116 (BYK) (manufactured by the company) as a dispersant, 14 parts by mass of a binder resin (B-1) solution, 60 parts by mass of propylene glycol monomethyl ether acetate as a solvent, mixed and dispersed by a bead mill to prepare a pigment dispersion Liquid (A-7).

<Preparation and evaluation of coloring composition> Example 1 Preparation of coloring composition

950 parts by mass of the pigment dispersion liquid (A-1), 95 parts by mass of the binder resin (B-2) solution as the (B) binder resin, and the above formula (C-1) as the (C) photopolymerization initiator 7 parts by mass of the compound shown, 70 parts by mass of caprolactone-modified dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., trade name KAYARAD DPCA-60) as the component (D), and (E) polyfunctional sulfur 4 parts by mass of pentaerythritol tetrakis(3-mercaptopropionate) of an alcohol (trade name: PEMP II-20P, manufactured by SC Organic Chemical Co., Ltd.), and 0.7 parts by mass of MEGAFAC F-554 manufactured by DIC Co., Ltd. as a fluorine-based surfactant. The mixture was mixed with 3-methoxybutyl acetate as a solvent to prepare a liquid colored composition (S-1) having a solid concentration of 20% by mass.

Water spot evaluation

The liquid colored composition (S-1) was applied onto a glass substrate by a spin coater, and then prebaked in a hot plate at 90 ° C for 4 minutes to form a coating film having a film thickness of 2.0 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to radiation including wavelengths of 365 nm, 405 nm, and 436 nm by a high-pressure mercury lamp through a photomask at an exposure amount of 400 J/m ² . Thereafter, a developing solution containing a 0.04% by mass aqueous solution of potassium hydroxide at 23° C. was sprayed onto the coating film on the substrate at a developing pressure of 1.5 kgf/cm ² (nozzle diameter: 1 mm) until the coating film of the unexposed portion was completely peeled off. 5 seconds, thereby performing spray development. Thereafter, ultrapure water was sprayed at a washing pressure of 1.5 kgf/cm ² (nozzle diameter: 1 mm) for 60 seconds, thereby performing a rinsing treatment to form a dot pattern of 200 μm × 200 μm.

After the moisture on the surface of the substrate on which the dot pattern was formed was removed by a gas flow, the 20 dot pattern was observed using an optical microscope. Among the 20 patterns, "x" was evaluated when water spots were observed in 10 or more patterns, "△" was observed when water spots were observed on 1 to 9 patterns, and "○" was evaluated when no water spots were observed at all. "." The evaluation results are shown in Table 2.

Turbidity evaluation

The liquid colored composition (S-1) was applied onto a glass substrate by a spin coater, and then prebaked for 1 minute on a hot plate at 90 ° C to form a coating film having a film thickness of 2.5 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to radiation having wavelengths of 365 nm, 405 nm, and 436 nm at a exposure amount of 600 J/m ² using a high-pressure mercury lamp without passing through a photomask. Thereafter, a developing solution containing a 0.04% by mass aqueous sodium carbonate solution at 23° C. was sprayed onto the coating film on the substrate at a developing pressure of 1 kgf/cm ² (nozzle diameter: 1 mm) to carry out shower development. The obtained substrate was lifted up with a sodium lamp to observe the presence or absence of turbidity. The substrate having no turbidity was evaluated as "○", and the substrate having turbidity was evaluated as "x". The evaluation results are shown in Table 2.

Evaluation of brightness reduction caused by post-baking

The liquid colored composition (S-1) was applied onto a glass substrate by a spin coater, and then prebaked for 1 minute on a hot plate at 90 ° C to form a coating film having a film thickness of 2.5 μm. Next, after the substrate was cooled to room temperature, the coating film on the substrate was exposed to radiation having wavelengths of 365 nm, 405 nm, and 436 nm at a exposure amount of 600 J/m ² using a high-pressure mercury lamp without passing through a photomask. Thereafter, a developing solution formed of a 0.04% potassium hydroxide aqueous solution at 23 ° C was sprayed onto the coating film on the substrate at a developing pressure of 1 kgf/cm ² (nozzle diameter: 1 mm) to carry out shower development. Thereafter, the substrates were washed with ultrapure water, air-dried, and further post-baked in a cleaning oven at 230 ° C for 20 minutes to prepare a green cured film.

For the cured film after development and after baking, a color analyzer (MCPD 2000 manufactured by Otsuka Electronics Co., Ltd.) was used, and the chromaticity in the CIE color system was measured with a C light source and a 2 degree field of view. As a result of the measurement, the case where the decrease in the luminance Y was less than 2.5% before and after the post-baking was evaluated as "○", and the case where 2.5% or more was evaluated as "x". Further, the lower the reduction rate of the luminance Y, the better. The evaluation results are shown in Table 2.

Evaluation of heat resistance

The substrate obtained in the above "Evaluation of brightness reduction by post-baking" was further heated at 250 ° C for 30 minutes. Then, the surface of the substrate was observed with an optical microscope having an eyepiece magnification of 10 times and an objective magnification of 10 times. The case where the foreign matter confirmed in one field of view is three or less is evaluated as "○", and the case where the foreign matter confirmed in one field of view is four to nine is evaluated as "△", and will be in one field of view. When the number of foreign substances confirmed in the middle is 10 or more, it is evaluated as "X". Also, the smaller the number of foreign objects, the better. The evaluation results are shown in Table 2.

Examples 2 to 32 and Comparative Examples 1 to 12

In the same manner as in Example 1, except that the pigment dispersion liquid, the binder resin, and the like shown in Table 1 were changed, the liquid coloring composition (S-2) to (S) was prepared. -44).

Each of the evaluations was carried out in the same manner as in Example 1 except that the liquid colored composition (S-2) to (S-44) was used instead of the liquid colored composition (S-1). The evaluation results are shown in Table 2.

In Table 1, each component is as follows.

C-1: a compound represented by the above formula (C-1)

C-2: Ethyl ketone-1-[9-ethyl-6-(2-methylbenzylidene)-9H-indazol-3-yl]-1-(O-acetamidine) (trade name) IRGACURE OX02, manufactured by BASF)

C-3: 2,2'-bis(2-chlorophenyl)-4,4',5,5'-tetraphenyl-1,2'-biimidazole (manufactured by Hodogaya Chemical Co., Ltd.)

C-4: 2-benzyl-2-dimethylamino-1-(4- Polinylphenyl)butan-1-one (trade name: IRGACURE 369, manufactured by BASF Corporation)

C-5: 2,4-diethylthioxanthone (manufactured by Nippon Kayaku Co., Ltd.)

C-6: 4,4'-bis(diethylamino)benzophenone (manufactured by Hodogaya Chemical Co., Ltd.)

D-1: caprolactone-modified dipentaerythritol hexaacrylate (trade name KAYARAD DPCA-60, manufactured by Nippon Kayaku Co., Ltd.)

D-2: a mixture of dipentaerythritol hexaacrylate and dipentaerythritol pentaacrylate (trade name KAYARAD MAX-3510, manufactured by Nippon Kayaku Co., Ltd.)

E-1: pentaerythritol tetrakis(3-mercaptopropionate) (trade name: PEMP II-20P, manufactured by SC Organic Chemical Co., Ltd.)

E-2: sesquioxane polyfunctional thiol (trade name: COMPOCERAN HBSQ105-9, manufactured by Arakawa Chemical Co., Ltd.)

Claims (8)

A coloring composition comprising (A) a colorant, (B) a binder resin, (C) a photopolymerization initiator represented by the following formula (1), and (D) having two or more polymerizable unsaturated bonds And (E) a polyfunctional thiol, (B) a binder resin containing a polymer having an acidic functional group and a (meth) acrylonitrile group, and is: (b-3) a polymerizable group having a carboxyl group a polymer obtained by reacting an unsaturated compound with an epoxy group of a polymer having an epoxy group-containing polymerizable unsaturated compound, and further reacting an acid anhydride with a hydroxyl group formed by the reaction; or (b-4) having a polymer obtained by reacting a carboxyl group-containing polymerizable unsaturated compound with an epoxy group of an epoxy resin, and further reacting an acid anhydride with a hydroxyl group formed by the reaction, In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 4 to 20 carbon atoms or a phenyl group, wherein the phenyl group has hydrogen A part or all of the atom may be substituted by an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and R ² represents a methylene group or an alkylene group having 2 to 20 carbon atoms. R ³ represents an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a phenyl group or a naphthyl group, and R ⁵ represents a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, and a 9-fluorenyl group (9). -fluorenyl), 2-furyl or 2-thienyl, wherein some or all of the hydrogen atoms of these groups may be an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. Replace. A coloring composition comprising (A) a colorant, (B) a binder resin, (C) a photopolymerization initiator represented by the following formula (1), and (D) having two or more polymerizable unsaturated bonds a compound and (E) a polyfunctional thiol, (E) a polyfunctional thiol containing a polyoxyalkylene having two or more sulfanyl groups, In the formula (1), R ¹ and R ⁴ each independently represent an alkyl group having 1 to 12 carbon atoms, an alicyclic hydrocarbon group having 4 to 20 carbon atoms or a phenyl group, wherein the phenyl group has hydrogen A part or all of the atom may be substituted by an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and R ² represents a methylene group or an alkylene group having 2 to 20 carbon atoms. R ³ represents an alicyclic hydrocarbon group having 3 to 20 carbon atoms, a phenyl group or a naphthyl group, and R ⁵ represents a phenyl group, a tolyl group, a xylyl group, a naphthyl group, an anthracenyl group, a phenanthryl group, a 9-fluorenyl group, and 2 a furyl group or a 2-thienyl group, wherein a part or all of the hydrogen atoms of these groups may be substituted by an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms. The coloring composition of claim 1 or 2, wherein the R ³ is a cycloalkyl group having 3 to 8 carbon atoms. A colored composition according to claim 1 or 2, which contains a zinc halide phthalocyanine pigment as the (A) colorant, and the content ratio of the (A) colorant is 30 to 60% by mass in the total solid content. . The coloring composition of the first or second aspect of the invention, which comprises two or more selected from the group consisting of CI Pigment Red 177, CI Pigment Red 242, and CI Pigment Red 254 as the (A) colorant, and The content ratio of the (A) colorant is 30 to 60% by mass based on the total solid content. The coloring composition of claim 1 or 2 further comprising a biimidazole photopolymerization initiator. A color filter comprising a coloring layer formed using the coloring composition according to any one of claims 1 to 6. A display element comprising the color filter of item 7 of the patent application.