KR20130034597A - Coloring composition, color filter and display device - Google Patents

Abstract

PURPOSE: A coloring composition, a color filter, and a display device are provided to offer a coloring composition of which problems in a photolithography process or a heating process manufacturing the color filter are solved and to offer a color filter and a display device equipped with the color filter comprises by equipping a chromatic layer including the coloring composition. CONSTITUTION: A coloring composition comprises a polymerization and a multi-functional thiol having the coloring agent, binder resin, photopolymerization initiator and more than two polymerizable unsaturated bonds. A color filter includes a chromatic layer formed by using the coloring composition. A display device includees the color filter.

Description

COLORING COMPOSITION, COLOR FILTER AND DISPLAY DEVICE,

This invention relates to a coloring composition, a color filter, and a display element, More specifically, formation of the colored layer useful for the color filter used for a transmissive or reflective color liquid crystal display element, a solid-state image sensor, an organic electroluminescent display element, an electronic paper, etc. It relates to a coloring composition used for the color filter, a color filter having a colored layer formed using the coloring composition, and a display element comprising the color filter.

In manufacturing a color filter using a colored radiation sensitive composition, after apply | coating a colored radiation sensitive composition on a board | substrate and drying, radiation of a dry coating film to a desired pattern shape (hereinafter, referred to as "exposure") And developing (patent documents 1-2) are known. Moreover, the method (patent document 3) which forms a black matrix using the photopolymerizable composition which disperse | distributed carbon black is also known.

Japanese Patent Laid-Open No. 2-144502 Japanese Patent Laid-Open No. 3-53201 Japanese Patent Publication No. 6-35188

In recent years, in the technical field of color filters, it has become mainstream to reduce the exposure time and shorten the tact time, and in order to meet the demand for high color purity for color liquid crystal display devices, colored radiation-sensitive compositions There exists a tendency for the content rate of the pigment to occupy to increase gradually. Under these circumstances, various problems are present in the production of color filters. For example, there is a problem that blur occurs in the pixel pattern after the development, causing the inspection process performed after the development step to stall, thereby lowering the production efficiency. In addition, after water washing performed following development, color unevenness (hereinafter, referred to as "water unevenness") in the form of spots is generated on the pixel pattern, and there is also a problem of stagnating the inspection process to lower the production efficiency. In addition, when a high temperature heating process (for example, post-baking process after development) is performed, there is a problem that luminance of the pixel is lowered or foreign matter is generated on the pixel pattern.

Therefore, the subject of this invention is providing the coloring composition which solved the various problem which arises in the image development process and heating process at the time of manufacturing a color filter. Moreover, the subject of this invention is providing the color filter which comprises the colored layer containing this coloring composition, and the display element provided with this color filter.

MEANS TO SOLVE THE PROBLEM As a result of earnestly examining, the present inventors discovered that the said subject can be solved by combining the specific photoinitiator and polyfunctional thiol in combination.

That is, this invention is a (A) coloring agent, (B) binder resin, (C) photoinitiator represented by following General formula (1), (D) the compound which has a 2 or more polymerizable unsaturated bond, and (E) polyfunctional thiol It is to provide a coloring composition comprising a.

In 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, provided that some or all of the hydrogen atoms of the phenyl group have May be substituted with 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, a phenyl group or a naphthyl group having 3 to 20 carbon atoms,

R ⁵ represents a phenyl group, tolyl group, xylyl group, naphthyl group, anthryl group, phenanthryl group, 9-fluorenyl group, 2-furyl group or 2-thienyl group, provided that some of the hydrogen atoms of these groups Or all may be substituted with an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms)

Moreover, this invention provides the color filter which comprises the colored layer formed using the said coloring composition, and the display element provided with the said color filter. Here, "colored layer" means each color pixel used for a color filter, a black matrix, a black spacer, etc.

When the coloring composition of this invention is used, since a blur and water spot hardly generate | occur | produce in the pixel pattern after a image development process, it becomes possible to manufacture a color filter with high production efficiency. Moreover, since the fall of the brightness | luminance accompanying a high temperature heating process and the generation of a foreign material can be suppressed, it becomes possible to manufacture a high quality color filter.

Therefore, the coloring composition of this invention is very preferable for preparation of various color filters, including the color filter for color liquid crystal display elements, the color filter for color separation of a solid-state image sensor, the color filter for organic electroluminescent display elements, and the color filter for electronic paper. Can be used.

Hereinafter, the present invention will be described in detail.

Coloring composition

Hereinafter, the structural component of the coloring composition of this invention is demonstrated.

- (A) Colorant -

In the present invention, the (A) colorant is not particularly limited, and any one of an organic pigment, an inorganic pigment, and a natural pigment may be used, but an organic pigment is preferable in that a color filter requires high color purity, brightness, contrast, and the like. .

The coloring composition of this invention can be used for formation of the coloring layer of each color pixel which comprises a color filter, a black matrix, a black spacer, etc., Generally, to form the green or red pixel in which the content rate of a coloring agent tends to become high. As a coloring composition for this, it is especially useful.

In the case of the coloring composition used for formation of a green pixel, a green coloring agent is used as (A) coloring agent. Examples of the green colorant include copper halide phthalocyanine, halogenated zinc phthalocyanine, magnesium halide phthalocyanine, aluminum halide phthalocyanine halide, titanium phthalocyanine halide, vanadium halide phthalocyanate, manganese halide phthalocyanine, halogenated iron phthalocyanine, halogenated cobalt phthalate And green pigments such as phthalocyanine, germanium halide phthalocyanine and indium phthalocyanide halide. Moreover, as a halogen, a chlorine atom, a bromine atom, etc. are mentioned.

Among these, zinc halide phthalocyanine, especially zinc bromide phthalocyanine and zinc chlorinated bromide phthalocyanine are preferable in that a green pixel with high luminance is obtained. Zinc chlorinated phthalocyanine is C.I. in color index (C.I.) name. It is a pigment classified into pigment green 58, and it is preferable that it is a structure represented by following General formula (2).

(In formula (2), X represents a chlorine atom or a bromine atom independently of each other, 10-15 of all X is a bromine atom, and remainder is a chlorine atom.)

In General formula (2), it is preferable that all the chlorine atoms of X are 1-6. The bromine atom can be appropriately selected within the range of 10 to 15 so that the sum of X is 16.

In this invention, a green coloring agent can be used individually or in mixture of 2 or more types.

In the case of the coloring composition used for formation of a green pixel, a yellow coloring agent is used normally with a green coloring agent. As the yellow colorant, it is preferable to use at least one of a quinophthalone pigment or an azobarbituric acid metal complex pigment in that a green pixel having high luminance is obtained. As a quinophthalone pigment, C.I. Pigment Yellow 138 is preferred. Moreover, as azobarbituric acid metal complex pigment, C.I. In addition to Pigment Yellow 150, those described in Japanese Patent Laid-Open No. 2001-354869 and Japanese Patent Laid-Open No. 2006-16506 are preferable. The coloring composition of this invention is C.I. When pigment yellow 138 is used, it is preferable at the point which can suppress the foreign material generate | occur | produced by a high temperature heating process.

On the other hand, in the case of the coloring composition used for formation of a red pixel, a red coloring agent is used as (A) coloring agent. As a red coloring agent, it is 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 these, C.I. Pigment Red 177, C.I. Pigment Red 242 and C.I. It is preferable to use two or more kinds selected from the group consisting of Pigment Red 254 in that a red pixel having high luminance is obtained.

Also in the case of the coloring composition used for formation of a red pixel, a yellow coloring agent may be used with a red coloring agent for coloring. As a yellow coloring agent, in addition to the yellow pigment used for formation of the said green pixel, C.I. Pigment Yellow 139 is preferred.

In addition, in the case of the coloring composition used for formation of a blue pixel, as a blue coloring agent, it is C.I. Pigment Blue 15: 6, C.I. Pigment Violet 23 and the like can be used.

When a pigment is used as a colorant in the present invention, the pigment may be purified and used by a recrystallization method, a reprecipitation method, a solvent cleaning method, a sublimation method, a vacuum heating method, or a combination thereof, if necessary. In addition, a pigment can also be used, modifying the particle surface with resin as needed. As resin which modifies the particle surface of a pigment, the vehicle resin of Unexamined-Japanese-Patent No. 2001-108817, or commercially available various pigment dispersion resin is mentioned, for example. In addition, the pigment is preferably used by miniaturizing the primary particles by so-called salt milling. As a method of salt milling, the method disclosed by Unexamined-Japanese-Patent No. 08-179111 can be employ | adopted, for example.

(A) The content rate of a coloring agent is 5-70 mass% normally in the total solid of a coloring composition from the point which forms the pixel which has high brightness | luminance and is excellent in color purity or excellent light-shielding property, Preferably it is 5-60 mass %to be. "Solid content" here is components other than the solvent mentioned later.

When the content rate of a coloring agent becomes high, there exists a tendency for a blur and water stain to arise easily in a pixel pattern, but when the coloring composition of this invention is used, when the content rate of a coloring agent becomes 30 mass% or more in the total solid of a coloring composition. Even if it is, it can suppress generation | occurrence | production of a blur and water stain. Moreover, as a range of the content rate of such a coloring agent, 30-60 mass% is preferable in the total solid of a coloring composition.

When using a pigment as a coloring agent in this invention, it can be used together with a dispersing agent as needed. As the dispersant, for example, suitable dispersants such as cationic, anionic and nonionic systems can be used, but a polymer dispersant is preferable. Specifically, urethane-based dispersants, polyethyleneimine-based dispersants, polyoxyethylene alkyl ether dispersants, polyoxyethylene alkyl phenyl ether dispersants, polyethylene glycol diester dispersants, sorbitan fatty acid ester dispersants, polyester dispersants, acrylic dispersants Etc. can be mentioned.

Such dispersants are commercially available, for example, as an acrylic dispersant, Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 (above, manufactured by BYK Corporation), urethane dispersants As Disperbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (above, manufactured by BYK Corporation), Solsperth 76500 (manufactured by Lubrizol) As a polyethyleneimine-based dispersant, Solsper Sper 24000 (manufactured by Lubrizol Co., Ltd.), a polyester-based dispersant, Azisper PB821, Azisper PB822, Azisper PB880, Azisper PB881 (Ajinomoto Fine Techno Co., Ltd.) Kaisha) etc. are mentioned. In addition, content of a dispersing agent can be suitably determined within the range which does not impair the objective of this invention.

(B) binder resin

Although it does not specifically limit as (B) binder resin in this invention, It is preferable that it is resin which has acidic functional groups, such as a carboxyl group and a phenolic hydroxyl group. In order to improve the effect which this invention wants, it is preferable to use the polymer which has an acidic functional group and also a polymerizable unsaturated group.

Although a carboxyl group, a phenolic hydroxyl group, etc. are mentioned as said acidic functional group, A carboxyl group is preferable from the point of alkali solubility and the storage stability of the coloring composition obtained.

Moreover, although a vinylaryl group, a (meth) acryloyl group, an allyl group, etc. are mentioned as said polymerizable unsaturated group, A (meth) acryloyl group is preferable at the point which raises a desired effect. Moreover, it is preferable that the polymer which has an acidic functional group and a polymerizable unsaturated group has a polymerizable unsaturated group in the side chain of the polymer which has an acidic functional group.

The polymer having an acidic functional group and a polymerizable unsaturated group is not particularly limited as long as the above requirements are satisfied. For example, (b-1) a polymerizable polymer having an oxiranyl group in the carboxyl group of the polymer of the polymerizable unsaturated compound having a carboxyl group The hydroxyl group of the copolymer of the polymer obtained by making an unsaturated compound react (henceforth "binder resin (b-1)"), and (b-2) the polymerizable unsaturated compound which has a hydroxyl group, and the polymerizable unsaturated compound which has an acidic functional group. A carboxyl group is used in an oxiranyl group of a polymer obtained by reacting a polymerizable unsaturated compound having an isocyanate group (hereinafter referred to as "binder resin (b-2)") and a polymer of a polymerizable unsaturated compound having an oxiranyl group (b-3). A polymer obtained by reacting a polymerizable unsaturated compound having a reaction with an acid anhydride in the hydroxyl group generated by the reaction ( Hereinafter, it is obtained by making a polymerizable unsaturated compound which has a carboxyl group react with the epoxy group of "binder resin (b-3)" and (b-4) epoxy resin, and making an acid anhydride react with the hydroxyl group produced by the said reaction. A polymerizable unsaturated compound having a hydroxyl group is reacted with a polymer (hereinafter referred to as "binder resin (b-4)"), (b-5) styrene or a derivative thereof and a copolymer of maleic anhydride or an ester thereof. The polymer obtained (henceforth "binder resin (b-5)") etc. are mentioned.

The polymer of the polymerizable unsaturated compound having a carboxyl group used for the manufacture of 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.

As a polymerizable unsaturated compound which has a carboxyl group, For example, Unsaturated compound (for example, (omega) -carboxypolycaprolactone mono (meth) acrylate which added lactones to (meth) acrylic acid other than (meth) acrylic acid and maleic acid) ); Unsaturated compounds (for example, 2- (meth) acryloyloxyethyl succinic acid) which added dibasic acids, such as succinic acid, maleic acid, and phthalic acid, or its anhydride to hydroxyalkyl (meth) acrylate, etc. are mentioned. have. These can also be used in multiple types.

Especially, (meth) acrylic acid, 2- (meth) acryloyloxyethyl succinic acid, (omega) -carboxypolycaprolactone mono (meth) acrylate is preferable, and (meth) acrylic acid is preferable.

As a polymerizable unsaturated compound which has an oxiranyl group used for manufacture of binder resin (b-1), for example, glycidyl (meth) acrylate, allyl glycidyl ether, glycidyl-alpha-ethyl acrylate, Crotonylglycidyl ether, (iso) crotonic acid glycidyl ether, N- (3,5-dimethyl-4-glycidyl) benzyl acrylamide, 4-hydroxybutyl (meth) acrylate glycidyl ether unsaturated compounds having glycidyl groups such as p-vinylbenzyl glycidyl ether; Alicyclic epoxy groups such as 2,3-epoxycyclopentyl group, 3,4-epoxycyclohexyl group, 7,8-epoxy [tricyclo [5.2.1.0] dec-2-yl] group, and (meth) acrylo And unsaturated compounds having a polymerizable unsaturated group such as a diary. These can also be used in multiple types.

Although the copolymer of the polymerizable unsaturated compound which has a hydroxyl group used for manufacture of binder resin (b-2), and the polymerizable unsaturated compound which has an acidic functional group will not be specifically limited if it has a hydroxyl group and an acidic functional group, Polymerization which has a hydroxyl group at least It is obtained by superposing | polymerizing the polymerizable unsaturated compound which has an acidic unsaturated compound and an acidic functional group.

As a polymerizable unsaturated compound which has a hydroxyl group and a vinyl group, 4-hydroxybutyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, glycerol mono (meth) acrylate, etc. In addition to the hydroxyalkyl (meth) acrylate, N-methylol acrylamide, allyl alcohol, etc. are mentioned. Moreover, as a polymerizable unsaturated compound which has an acidic functional group, the polymerizable unsaturated compound which has a carboxyl group mentioned by the said binder resin (b-1), etc. are mentioned. These can also be used in multiple types.

As a polymerizable unsaturated compound which has an isocyanate group used for manufacture of binder resin (b-2), it is 2- (meth) acryloyloxyethyl isocyanate, (meth) acrylic acid 2- (2-isocyanate ethoxy) ethyl, for example. And 1,1- (bisacryloyloxymethyl) ethyl isocyanate. These can also be used in multiple types.

The polymer of the polymerizable unsaturated compound having an oxiranyl group used in the preparation of the binder resin (b-3) may be a polymer having an oxiranyl group, but a poly (meth) acrylic acid ester copolymer having an oxiranyl group, having an oxiranyl group Polystyrene copolymers; and the like. The poly (meth) acrylic acid ester type copolymer which has an oxiranyl group is a copolymer of the (meth) acrylic acid ester which has an oxiranyl group, and another polymerizable unsaturated compound. Examples of the (meth) acrylic acid ester having an oxiranyl group include glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 4-hydride. Oxybutyl (meth) acrylate glycidyl ether, and the like. These can also be used in multiple types.

Moreover, as styrene which has the oxiranyl group which comprises the styrenic copolymer which has an oxiranyl group, o-vinyl benzyl glycidyl ether, m-vinyl benzyl glycidyl ether, p-vinyl benzyl glycidyl ether, 2,4 Styrene which has 1-3 glycidyl groups, such as diglycidyl oxymethyl styrene and 3,4, 5- triglycidyl methyl styrene, is mentioned. These can also be used in multiple types.

As a polymerizable unsaturated compound which has a carboxyl group used for manufacture of binder resin (b-3), (meth) acrylic acid, (omega)-carboxy- polycaprolactone mono (meth) acrylate, and 2- (meth) acryloyl ethyl succinic acid Etc. can be mentioned. These can also be used in multiple types.

As an acid anhydride used for manufacture of binder resin (b-3), for example, malonic anhydride, maleic anhydride, citraconic anhydride, succinic anhydride, glutaric anhydride, glutamic anhydride, itaconic anhydride, anhydrous And polybasic acid anhydrides such as diglycolic acid, phthalic anhydride, cyclohexane-1,2-dicarboxylic acid anhydride, 4-cyclohexene-1,2-dicarboxylic acid anhydride, and diphenic anhydride. These can also be used in multiple types.

Moreover, the polymer of the polymerizable unsaturated compound which has a carboxyl group used for manufacture of binder resin (b-1), and the polymerizable unsaturated compound which has a hydroxyl group used for manufacture of binder resin (b-2), and a polymerizable having an acidic functional group are used. In the polymer of the polymerizable unsaturated compound which has the oxiranyl group used for manufacture of the copolymer of an unsaturated compound and binder resin (b-3), the other polymerizable unsaturated compound copolymerizable with each polymerizable unsaturated compound can be copolymerized.

As such another polymerizable unsaturated compound, For example, N-substituted maleimide, such as N-phenylmaleimide and N-cyclohexyl maleimide; Aromatic vinyl compounds such as styrene, α-methylstyrene, p-hydroxy-α-methylstyrene, acenaphthylene and the like; Methyl (meth) acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, isobornyl (meth) acrylate, Ethylene Oxide Modification of Tricyclo [5.2.1.0 ^2,6 ] decane-8-yl (meth) acrylate, Dicyclopentenyl (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, Paracumylphenol ( (Meth) acrylic acid ester, such as meth) acrylate, etc. are mentioned.

Moreover, in the polymer of the polymerizable unsaturated compound which has a carboxyl group used for manufacture of a polymer (b-1), and the polymer of the polymerizable unsaturated compound which has an oxiranyl group used for manufacture of a polymer (b-3), 2-hydride The polymerizable unsaturated compound which has hydroxyl groups, such as oxyethyl (meth) acrylate and glycerol mono (meth) acrylate, can be copolymerized. These can also be used in multiple types.

As an epoxy resin used for manufacture of binder resin (b-4), the epoxy resin obtained by reaction of the alcoholic hydroxyl group and epichlorohydrin of bisphenol-A epoxy resin, bisphenol-A epoxy resin, bisphenol F-type epoxy resin, and bisphenol Epoxy resin obtained by reaction of alcoholic hydroxyl group and epichlorohydrin of F-type epoxy resin, bisphenol S-type epoxy resin, biphenylglycidyl ether, phenol novolak-type epoxy resin, cresol novolak-type epoxy resin, triglycidyl Isocyanurate, a trisphenol methane type epoxy resin, a fluorene epoxy resin, an alicyclic epoxy resin, a dicyclopentadiene type epoxy resin, etc. are mentioned. Copolymer type epoxy resins can also be used.

As a polymerizable unsaturated compound and acid anhydride which have a carboxyl group used for manufacture of binder resin (b-4), the thing similar to what is used in manufacture of the said binder resin (b-3) is mentioned.

As a copolymer of styrene or its derivative used for manufacture of binder resin (b-5), and maleic anhydride or its ester, For example, styrene, m-methoxy styrene, p-methoxy styrene, etc. Derivatives, maleic anhydride or monomethyl maleate, monoethyl maleate, mono-n-propyl maleate, mono-maleic acid-iso-propyl, mono-maleic acid-n-butyl, monomaleic acid-iso-butyl, And copolymers of maleic acid mono lower alkyl esters such as mono-tert-butyl maleate.

As a polymerizable unsaturated compound which has a hydroxyl group used for manufacture of binder resin (b-5), hydroxyalkyl (meth) acrylate, N-methylol acrylamide, allyl alcohol, etc. are mentioned.

In the present invention, as the binder resin, a polymer having an acidic functional group but no polymerizable unsaturated group can be used alone. As such binder resin, For example, Unexamined-Japanese-Patent No. 7-140654, Unexamined-Japanese-Patent No. 9-311444, Unexamined-Japanese-Patent No. 10-31308, Japan Patent Publication Japanese Patent Laid-Open No. 10-300922, Japanese Patent Laid-Open Japanese Patent Laid-Open No. 11-174224, Japanese Patent Laid-Open No. 11-258415, Japanese Patent Laid-Open No. 2000-56118 The copolymer disclosed in 2002-296778, Unexamined-Japanese-Patent No. 2004-101728, etc. are mentioned. Of course, the polymer which has an acidic functional group but does not have a polymerizable unsaturated group can also be used together with the polymer which has an acidic functional group and a polymerizable unsaturated group.

The acid value of binder resin in this invention becomes like this. Preferably it is 10-200KOH / mg, More preferably, it is 20-150KOH / mg, More preferably, it is 30-150KOH / mg. Here, the acid value represents the number of mg of KOH necessary to neutralize 1 g of nonvolatile matter excluding the solvent of the polymer solution.

As for binder resin in this invention, the weight average molecular weight (Mw) of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran) is 1,000-100,000 normally, Preferably it is 3,000-50,000. If Mw is too small, the remaining film ratio or the like of the resulting film may be lowered, the pattern shape, heat resistance, or the like may be damaged, or the electrical characteristics may be deteriorated. There exists a possibility that a dry foreign material may generate easily at the time of application | coating by a nozzle system.

Moreover, ratio (Mw / Mn) of the weight average molecular weight of binder resin in this invention, and the number average molecular weight (Mn) of polystyrene conversion measured by GPC (elution solvent: tetrahydrofuran) becomes like this. Preferably it is 1.0-5.0 More preferably, they are 1.0-3.0.

The binder resin in this invention can be manufactured by a well-known method, For example, Unexamined-Japanese-Patent No. 2003-222717, 2006-259680, International Publication 07/029871, etc. By the method disclosed, the structure, Mw, and Mw / Mn can also be controlled.

In this invention, binder resin can be used individually or in mixture of 2 or more types.

In this invention, 10-1,000 mass parts is preferable with respect to 100 mass parts of (A) coloring agents, and, as for content of binder resin, 20-500 mass parts is especially preferable. When content of binder resin is too small, alkali developability may fall, for example, there exists a possibility that the storage stability of the coloring composition obtained may fall, and when too much, when it is set as a thin film, since the coloring agent density | concentration falls relatively, There is a possibility that it will be difficult to achieve the desired color density.

- (C) Photopolymerization initiator -

The photopolymerization initiator (C) used in the present invention initiates polymerization of a compound having two or more polymerizable unsaturated bonds (D) described later by exposure to radiation such as visible light, ultraviolet ray, far ultraviolet ray, electron beam, and X-ray. It is a compound that generates active species. The coloring composition of this invention contains the compound represented by the said General formula (1) as (C) photoinitiator, It is characterized by the above-mentioned.

In the formula (1), examples of the alkyl group having 1 to 12 carbon atoms represented by R ¹ or R ⁴ include, for example, methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group and i-butyl group. , t-butyl group, n-pentyl group, n-hexyl group and the like. Moreover, as a C4-C20 alicyclic hydrocarbon group represented by R <^1> or R <^4> , for example, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a bornyl group, a norbornyl group, an adamantyl group Etc. can be mentioned. In this invention, it is preferable that R <^1> is a C1-C6 alkyl group or a phenyl group, and it is especially preferable that it is a methyl group or a phenyl group. Moreover, it is preferable that R <^4> is a C1-C6 alkyl group or a phenyl group, and it is especially preferable that it is an ethyl group or a phenyl group.

In the formula (1), examples of the alkylene group having 2 to 20 carbon atoms represented by R ² include an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, and the like. In this invention, it is preferable that R <^2> is a methylene group or a C2-C5 alkylene group, and it is especially preferable that it is a methylene group or ethylene group.

In said Formula (1), as a C3-C20 alicyclic hydrocarbon group represented by R <^3> , a C3-C8 cycloalkyl group, a bornyl group, a norbornyl group, an adamantyl group, etc. are mentioned, for example. . In this invention, it is preferable that R <^3> is a C3-C8 cycloalkyl group, and it is especially preferable that it is a cyclopentyl group or a cyclohexyl group. In the 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 phenyl group represented by R ¹ or R ⁴ or a substituent which R ⁵ has include methyl group, ethyl group, n-propyl group, i-propyl group, n -Butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc. are mentioned. As a C1-C12 alkoxy group which is a phenyl group represented by R <^1> or R <^4> or the substituent which R <^5> has, a methoxy group, an ethoxy group, a propoxy group, etc. are mentioned, for example.

As a photoinitiator represented by the said General formula (1), the compound etc. which are represented by following General formula (C-1)-(C-10) are mentioned, for example.

In this invention, the photoinitiator represented by the said General formula (1) can be used individually or in mixture of 2 or more types.

In this invention, another photoinitiator can be used together with the photoinitiator represented by the said General formula (1). As such a photoinitiator, a thioxanthone type photoinitiator, an acetophenone type photoinitiator, a biimidazole type photoinitiator, a triazine type photoinitiator, O-acyl oxime type photoinitiators other than the said Formula (1), an onium salt type, for example A photoinitiator, a benzoin type photoinitiator, a benzophenone type photoinitiator, the (alpha)-diketone type photoinitiator, a polynuclear quinone type photoinitiator, a diazo type photoinitiator, an imidosulfonate type photoinitiator, etc. are mentioned.

Of these, thioxanthone photopolymerization initiators, acetophenone photopolymerization initiators, biimidazole photopolymerization initiators, triazine photopolymerization initiators or O-acyl oxime photopolymerization initiators other than the formula (1) are preferable, and desired effects are improved. In particular, a biimidazole type photoinitiator is preferable at the point.

In this invention, another photoinitiator can be used individually or in mixture of 2 or more types.

As another example of a thioxanthone type photoinitiator among other photoinitiators, thioxanthone, 2-chloro thioxanthone, 2-methyl thioxanthone, 2-isopropyl thioxanthone, 4-isopropyl thioxanthone, 2 , 4-dichloro thioxanthone, 2,4-dimethyl thioxanthone, 2,4-diethyl thioxanthone, 2,4-diisopropyl thioxanthone, etc. are mentioned.

Moreover, as a specific example of the said acetophenone type photoinitiator, 2-methyl-1- [4- (methylthio) phenyl] -2- morpholino propane-1-one and 2-benzyl-2- dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, etc. are mentioned. .

Moreover, as a specific example of the said biimidazole type photoinitiator, 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-trichloro Phenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, etc. are mentioned.

Moreover, as a specific example of the said triazine photoinitiator, 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2 -[2- (5-methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl]- 4,6-bis (trichloromethyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-tri Azine, 2- [2- (3,4-dimethoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6- Bis (trichloromethyl) -s-triazine, 2- (4-ethoxystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) And triazine compounds having halomethyl groups, such as -4,6-bis (trichloromethyl) -s-triazine.

Moreover, as a specific example of O-acyl oxime system photoinitiators other than the said General formula (1), 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O- benzoyl oxime), eta Non, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- (2-Methyl-4-tetrahydrofuranylmethoxybenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyloxime), ethanone, 1- [9-ethyl-6- {2- Methyl-4- (2,2-dimethyl-1,3-dioxoranyl) methoxybenzoyl} -9H-carbazol-3-yl]-, 1- (O-acetyl oxime) and the like. As a commercial item of an O-acyl oxime type compound, NCI-831, NCI-930 (above, the product made from Adeka Corporation) etc. can also be used.

In this invention, a sensitizer can also be used together with the above photoinitiator. As such a sensitizer, 4,4'-bis (dimethylamino) benzophenone, 4,4'-bis (diethylamino) benzophenone, 4-diethylamino acetophenone, 4-dimethylamino propiophenone, for example. Ethyl 4-dimethylaminobenzoate, 2-ethylhexyl 4-dimethylaminobenzoic acid, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl ) Coumarin, 4- (diethylamino) chalcone, and the like.

In this invention, as for content of the photoinitiator represented by the said General formula (1), 1-20 mass parts is preferable with respect to 100 mass parts of compounds which have two or more polymerizable unsaturated bonds (D) mentioned later, Especially 3-3 10 mass parts is preferable. In this case, when there is too little content of the photoinitiator represented by the said General formula (1), there exists a possibility that a desired effect may not be fully acquired, and when too much, there exists a tendency for brightness and solubility of a developing solution to fall easily.

In addition, when using together the photoinitiator represented by the said General formula (1) with another photoinitiator, content of another photoinitiator becomes like this. Preferably it is 10-300 mass with respect to 100 mass parts of photoinitiators represented by the said General formula (1). Part, particularly preferably 20 to 150 parts by mass.

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

In this invention, although it does not specifically limit as a compound which has (D) two or more polymerizable unsaturated bonds, The compound which has two or more (meth) acryloyl groups is preferable.

As a compound which has two or more (meth) acryloyl groups, the polyfunctional (meth) acrylate obtained by making an aliphatic polyhydroxy compound and (meth) acrylic acid react, for example, the polyfunctional (meth) acrylate modified with caprolactone , Polyfunctional urethane (meth) acrylate obtained by reacting alkylene oxide-modified polyfunctional (meth) acrylate, (meth) acrylate having hydroxyl group and polyfunctional isocyanate, (meth) acrylate having hydroxyl group and acid anhydride The polyfunctional (meth) acrylate which has a carboxyl group obtained by making it react, etc. are mentioned.

Here, as said aliphatic polyhydroxy compound, For example, bivalent aliphatic polyhydroxy compounds, such as ethylene glycol, propylene glycol, polyethylene glycol, and a polypropylene glycol, glycerin, trimethylol propane, pentaerythritol, and dipentaerythritol, The same trivalent or more aliphatic polyhydroxy compound is mentioned. As (meth) acrylate which has the said hydroxyl group, 2-hydroxyethyl (meth) acrylate, trimethylolpropanedi (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol penta, for example (Meth) acrylate, glycerol dimethacrylate, etc. are mentioned. As said polyfunctional isocyanate, tolylene diisocyanate, hexamethylene diisocyanate, diphenylmethylene diisocyanate, isophorone diisocyanate, etc. are mentioned, for example. As the acid anhydride, for example, anhydrides of dibasic acids such as succinic anhydride, maleic anhydride, glutaric anhydride, itaconic anhydride, phthalic anhydride, hexahydro phthalic anhydride, pyromellitic anhydride, biphenyltetracarboxylic acid 2 Tetrabasic acid dianhydrides such as anhydride and benzophenone tetracarboxylic dianhydride.

Moreover, as said caprolactone modified polyfunctional (meth) acrylate, the compound of Paragraph [0015]-[0018] of Unexamined-Japanese-Patent No. 11-44955 is mentioned, for example. Examples of the alkylene oxide-modified polyfunctional (meth) acrylates include di (meth) acrylates modified with at least one selected from ethylene oxide of bisphenol A and propylene oxide of bisphenol A, and ethylene oxide of isocyanuric acid. And a tree modified by at least one selected from tri (meth) acrylates selected from propylene oxide of isocyanuric acid, ethylene oxide of trimethylolpropane and propylene oxide of trimethylolpropane ( Tri (meth) acrylate modified by at least one selected from meth) acrylate, ethylene oxide of pentaerythritol and propylene oxide of pentaerythritol, ethylene oxide of pentaerythritol and propylene oxide of pentaerythritol Denatured by at least one Penta (meth) acrylate modified with at least one selected from tri (meth) acrylate, ethylene oxide of dipentaerythritol and propylene oxide of dipentaerythritol, ethylene oxide and dipentaerythrate of dipentaerythritol Hexa (meth) acrylate etc. modified with at least 1 sort (s) chosen from the propylene oxide of a lititol are mentioned.

Of these, polyfunctional (meth) acrylates obtained by reacting a trivalent or higher aliphatic polyhydroxy compound with (meth) acrylic acid, caprolactone-modified polyfunctional (meth) acrylates, polyfunctional urethane (meth) acrylates, and carboxyl groups Preference is given to polyfunctional (meth) acrylates having In the polyfunctional (meth) acrylate obtained by making a trivalent or more aliphatic polyhydroxy compound and (meth) acrylic acid react, trimethylolpropane triacrylate, pentaerythritol triacrylate, dipentaerythritol pentaacrylate, and di In the polyfunctional (meth) acrylate which pentaerythritol hexaacrylate has a carboxyl group, the compound obtained by making pentaerythritol triacrylate and succinic anhydride react, and the compound obtained by making dipentaerythritol pentaacrylate and succinic anhydride react This is particularly preferable in that the strength of the colored layer is high, the surface smoothness of the colored layer is excellent, and it is difficult to generate background contamination, film residue, etc. on the substrate and the light shielding layer of the unexposed part.

In the present invention, the compound (D) having two or more polymerizable unsaturated bonds may be used alone or in combination of two or more thereof.

50-300 mass parts is preferable with respect to 100 mass parts of (B) binder resin, and, as for content of the compound which has (D) two or more polymerizable unsaturated bonds in this invention, 90-200 mass parts is especially preferable. In this case, when there is too little content of the compound which has two or more polymerizable unsaturated bonds, there exists a tendency for the pixel to become cloudy and water spots easily generate | occur | produce. On the other hand, when there is too much content of the compound which has two or more polymerizable unsaturated bonds, when alkali developability is provided to the coloring composition of this invention, alkali developability will fall and it will be based on the board | substrate on the unexposed part, or on the light shielding layer. There is a tendency for contamination, film residues, etc. to occur easily.

(E) polyfunctional thiols

The coloring composition of this invention contains (E) polyfunctional thiol, ie, the compound which has 2 or more sulfanyl group (-SH), It is characterized by the above-mentioned. By using a polyfunctional thiol and the photoinitiator represented by the said General formula (1) together, it becomes possible to suppress cloudiness of a pixel pattern, generation | occurence | production of water, a fall of the brightness | luminance accompanying a high temperature heating process, and generation | occurrence | production of a foreign material.

The polyfunctional thiol is not particularly limited as long as it is a compound having two or more sulfanyl groups, but for example, hydrocarbons having two or more sulfanyl groups as substituents, poly (mercaptoacetates) of polyhydric alcohols, and polyhydric alcohols. Poly (3-mercaptopropionate) s, poly (2-mercaptopropionate) s of polyhydric alcohols, poly (3-mercaptobutyrate) s of polyhydric alcohols, and complexes having two or more sulfanyl groups as substituents Reflux, polysiloxanes having two or more sulfanyl groups, and the like.

Specific examples of hydrocarbons having two or more sulfanyl groups as the substituent include hexane-1,6-dithiol, decan-1,10-dithiol, 1,4-benzenedithiol, 1,4-bis (mercapto Methyl) benzene etc. are mentioned.

As a specific example of the poly (mercapto acetate) of the said polyhydric alcohol, ethylene glycol bis (mercapto acetate), propylene glycol bis (mercapto acetate), glycerin tris (mercapto acetate), trimethylol propane tris (mercapto acetate) , Pentaerythritol tetrakis (mercaptoacetate), dipentaerythritol hexakis (mercaptoacetate), and the like.

Specific examples of the poly (3-mercaptopropionate) of the polyhydric alcohol include ethylene glycol bis (3-mercaptopropionate), propylene glycol bis (3-mercaptopropionate), and glycerin tris (3- Mercaptopropionate), trimethylolpropane tris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), dipentaerythritol hexakis (3-mercaptopropionate) ), And the like.

Specific examples of the poly (2-mercaptopropionate) of the polyhydric alcohol include ethylene glycol bis (2-mercaptopropionate), propylene glycol bis (2-mercaptopropionate), and diethylene glycol bis ( 2-mercaptopropionate), butanediolbis (2-mercaptopropionate), octanediolbis (2-mercaptopropionate), trimethylolpropane tris (2-mercaptopropionate), pentaeryte Lithol tetrakis (2-mercaptopropionate), dipentaerythritol hexakis (2-mercaptopropionate), etc. are mentioned.

Specific examples of the poly (3-mercaptobutyrate) of the polyhydric alcohol include ethylene glycol bis (3-mercaptobutyrate), diethylene glycol bis (3-mercaptobutyrate), butanediolbis (3-mercaptobutyrate), Trimethylolpropane tris (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), dipentaerythritol hexakis (3-mercaptobutyrate), ethylene glycol bis (3-mercaptoisobutyrate) , Diethylene glycol bis (3-mercaptoisobutyrate), butanediol bis (3-mercaptoisobutyrate), trimethylol propane tris (3-mercaptoisobutyrate), pentaerythritol tetrakis (3-mercaptoisobutyrate) ), Dipentaerythritol hexakis (3-mercaptoisobutyrate), octanediolbis (3-mercaptobutyrate), octanediolbis (3-mercaptoisobutyrate), and the like.

Specific examples of the heterocyclic ring having two or more sulfanyl groups as the substituent include 2,4,6-trimercapto-s-triazine and 2- (N, N-dibutylamino) -4,6-dimercapto-s In addition to triazine, the 2-mercapto-5-substituted thiadiazole of Unexamined-Japanese-Patent No. 2-153353, etc. are mentioned.

As polysiloxane which has the said 2 or more sulfanyl group, the polysiloxane obtained by hydrolytically condensing the silane compound which has a sulfanyl group and a hydrolysable group is mentioned. About the specific form and a manufacturing method, it describes in Unexamined-Japanese-Patent No. 2008-242078, Unexamined-Japanese-Patent No. 2011-128239, etc., These descriptions are integrated in this specification. Moreover, the silsesquioxane which has two or more sulfanyl groups can use what is marketed by the Confoseran SQ series by Arakawa Chemical Industries, Ltd., for example.

Among these polyfunctional thiols, poly (mercaptoacetate) s of polyhydric alcohols, poly (3-mercaptopropionate) s of polyhydric alcohols, and poly (2-mers of polyhydric alcohols) in terms of further improving a desired effect. Captopropionate), poly (3-mercaptobutyrate) of polyhydric alcohols, and polysiloxanes having two or more sulfanyl groups.

In this invention, (E) polyfunctional thiol can be used individually or in mixture of 2 or more types.

In this invention, 5-200 mass parts is preferable with respect to 100 mass parts of photoinitiators represented by the said General formula (1), and, as for content of (E) polyfunctional thiol, 10-100 mass parts is especially preferable. In this case, when there is too little content of (E) polyfunctional thiol, there exists a possibility that a desired effect may not be acquired, and when too much, there exists a possibility that a pattern shape may become overhang shape.

-(F) solvent-

Although the coloring composition of this invention contains the said (A)-(E) component and the other component added arbitrarily, it is normally manufactured as a liquid composition by mix | blending a solvent.

As said solvent, as long as it disperse | distributes or melt | dissolves or dissolves the component (A)-(E) which comprises a coloring composition, and does not react with these components, and has moderate volatility, it can select suitably and can use.

As such a solvent, for example,

Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono- -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- Dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether, tri (Poly) alkylene glycol monoalkyl ethers such as propylene glycol monoethyl ether;

Lactic acid alkyl esters such as methyl lactate and ethyl lactate;

(Cyclo) alkyl alcohols such as methanol, ethanol, propanol, butanol, isopropanol, isobutanol, t-butanol, octanol, 2-ethylhexanol and cyclohexanol;

Keto alcohols such as diacetone alcohol;

Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, dipropylene glycol monomethyl ether (Poly) alkylene glycol monoalkyl ether acetates such as acetate, 3-methoxybutyl acetate and 3-methyl-3-methoxybutyl acetate;

Other ethers such as diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, diethylene glycol diethyl ether and tetrahydrofuran;

Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone;

Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate;

Alkoxy carboxyl, such as 3-methoxy methyl propionate, 3-methoxy ethylpropionate, 3-ethoxy ethyl propionate, 3-ethoxy ethyl propionate, ethyl ethoxy acetate, and 3-methyl-3- methoxy butyl propionate Acid esters;

Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-amyl acetate, i-amyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate Other esters such as n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, and ethyl 2-oxobutanoate;

Aromatic hydrocarbons such as toluene and xylene;

Amides or lactams such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and the like.

Among these solvents, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, from the viewpoint of solubility, pigment dispersibility, coating properties, etc. 3-methoxybutyl acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 1,3-butylene glycol diacetate, 1,6-hexanediol Diacetate, ethyl lactate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methyl-3-methoxybutylpropionate, n-butyl acetate, i-butyl acetate, N-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate, ethyl pyruvate and the like are preferred.

In this invention, a solvent can be used individually or in mixture of 2 or more types.

Although content of a solvent is not specifically limited, From the viewpoint of the applicability | paintability, stability, etc. of the coloring composition obtained, the quantity by which the total concentration of each component except the solvent of the said coloring composition becomes 5-50 mass% is preferable, Especially 10 The amount which becomes 40 mass% is preferable.

-additive-

The coloring composition of this invention may contain various additives as needed.

As an additive, For example, fillers, such as glass and an alumina; High molecular compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylate); Surfactants such as fluorine-based surfactants and silicone-based surfactants; Vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclo Hexyl) ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, etc. Adhesion promoter; 2,2-thiobis (4-methyl-6-t-butylphenol), 2,6-di-t-butylphenol, pentaerythritol tetrakis [3- (3,5-di-t-butyl-4 -Hydroxyphenyl) propionate]; Ultraviolet absorbers such as 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenones; An anti-aggregation agent such as sodium polyacrylate; Amino-1-pentanol, 3-amino-1,2-propane, 3-amino-1-pentanol, Diol, 2-amino-1,3-propanediol, 4-amino-1,2-butanediol and the like; Developability improvement agents, such as succinic acid mono [2- (meth) acryloyl oxyethyl], mono phthalate mono [2- (meth) acryloyl oxyethyl], (omega) -carboxypolycaprolactone mono (meth) acrylate, etc. are mentioned. Can be.

The coloring composition of this invention can be manufactured by a suitable method, As a manufacturing method, it is manufactured by mixing (A)-(E) component with (F) solvent and the other component added arbitrarily, for example. can do. When the pigment is used as the (A) colorant, the pigment is ground in the (F) solvent in the presence of a dispersant, optionally with a part of the component (B), for example, using a bead mill, a roll mill, or the like. The method of mixing and disperse | distributing to make a pigment dispersion liquid, and then adding and mixing (B)-(E) component, the solvent further added as needed, and another component as needed to this pigment dispersion liquid is preferable.

Color filter and its manufacturing method

The color filter of this invention is equipped with the colored layer formed using the coloring composition of this invention.

As a method of manufacturing a color filter, the following method is mentioned first. First, on the surface of a board | substrate, a light shielding layer (black matrix) is formed so that the part which forms a pixel may be divided as needed. Subsequently, after apply | coating the liquid composition of the radiation sensitive composition of this invention containing a red coloring agent on this board | substrate, for example, prebaking is performed and the solvent is evaporated and a coating film is formed. Subsequently, after exposing this coating film through a photomask, it develops using alkaline developing solution and removes and removes the unexposed part of a coating film. Thereafter, post-baking forms a pixel array in which red pixel patterns are arranged in a predetermined arrangement.

Subsequently, using each green radiation-sensitive colored radiation-sensitive composition, coating, prebaking, exposure, development, and post-baking of each colored radiation-sensitive composition are performed in the same manner as described above, whereby a green pixel array and a blue pixel are used. Arrays are sequentially formed on the same substrate. Thereby, the color filter by which the pixel array of three primary colors of red, green, and blue is arrange | positioned on a board | substrate can be obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above. In the first method of manufacturing the color filter, at least one of the red, green, and blue pixel arrays may be a colored layer formed using the coloring composition of the present invention.

In addition, the black matrix can be formed by forming a metal thin film such as chromium formed by sputtering or vapor deposition into a desired pattern using a photolithography method, but using a colored radiation-sensitive composition containing a black colorant, It may be formed in the same manner as in the case of forming the pixel. The coloring composition of this invention can be used suitably also for formation of such a black matrix.

As a board | substrate used at the time of forming a color filter, glass, silicone, polycarbonate, polyester, aromatic polyamide, polyamideimide, polyimide, etc. are mentioned, for example.

In addition, these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, vapor phase reaction, vacuum deposition, or the like if desired.

When apply | coating colored radiation-sensitive composition to a board | substrate, although the appropriate coating methods, such as a spray method, the roll coating method, the spin coating method (spin coat method), the slit die coating method, the bar coating method, can be employ | adopted, especially spin It is preferable to adopt a coating method and a slit die coating method.

Prebaking is normally performed combining a reduced pressure drying and heat drying. Drying under reduced pressure is usually performed until it reaches 50-200 Pa. The conditions for heating and drying are usually about 70 to 110 DEG C for about 1 to 10 minutes.

The coating thickness is usually 0.6 to 8 탆, preferably 1.2 to 5 탆, as a film thickness after drying.

As a light source for radiation used when forming pixels and / or black matrices, for example, a lamp light source such as a xenon lamp, a halogen lamp, a tungsten lamp, a high pressure mercury lamp, an ultra high pressure mercury lamp, a metal halide lamp, a medium pressure mercury lamp, a low pressure mercury lamp, Laser light sources, such as an argon ion laser, a YAG laser, an XeCl excimer laser, and a nitrogen laser, etc. are mentioned. As the exposure light source, an ultraviolet LED can also be used. Preferably, the wavelength is in the range of 190 to 450 nm.

Generally, the exposure amount of radiation is preferably 10 to 10,000 J / m 2. In general, the lower the exposure amount, the easier the blurring or water spots occur in the pixel pattern. However, when the exposure amount is 800 J / m 2 or less, and even 600 J / m 2 or less, the blurring or water spots are less likely to occur when the coloring composition of the present invention is used. .

As the alkaline developer, for example, sodium carbonate, sodium bicarbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-unsene, Aqueous solutions, such as 1, 5- diazabicyclo- [4.3.0] -5-nonene, are preferable.

A suitable amount of water-soluble organic solvents, such as methanol and ethanol, surfactant, etc. can also be added to the said alkaline developing solution. After the alkali development, it is usually washed with water.

As the developing treatment method, a shower developing method, a spray developing method, a dip (immersion) developing method, a puddle (liquid pooling) developing method, and the like can be applied. The developing conditions are preferably 5 to 300 seconds at room temperature.

Post-baking conditions are about 10 to 60 minutes at 120-280 degreeC normally. When the temperature of post-baking becomes high, brightness may fall or a foreign material may generate | occur | produce depending on the pigment species to be used, but when using the coloring composition of this invention, 200 degreeC or more, Furthermore, 220 degreeC or more This problem can be suppressed even at the post baking temperature.

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

Further, as a second method of manufacturing a color filter, a method of obtaining pixels of each color by an inkjet method disclosed in Japanese Patent Laid-Open No. 7-318723, Japanese Patent Laid-Open No. 2000-310706, or the like is disclosed. It can be adopted. In this method, first, a partition having both light shielding functions is formed on the surface of the substrate. Next, after discharging the liquid composition of the thermosetting composition of the present invention containing, for example, a red colorant in the formed partition wall by an inkjet apparatus, the solvent is evaporated by prebaking. Subsequently, after exposing this coating film as needed, it hardens | cures by post-baking to form a red pixel pattern.

Then, using each colored thermosetting composition of green or blue, a green pixel pattern and a blue pixel pattern are sequentially formed on the same substrate as described above. Thereby, the color filter by which the pixel pattern of three primary colors of red, green, and blue is arrange | positioned on a board | substrate is obtained. However, in the present invention, the order of forming the pixels of each color is not limited to the above. Moreover, also in the 2nd method of manufacturing a color filter, any one or more of the said red, green, and blue pixel array may be the colored layer formed using the coloring composition of this invention.

In addition, the partition wall has a film thickness thicker than that of the black matrix used in the above-described first method because it achieves not only a light shielding function but also a function for preventing the colored compositions of each color discharged into the compartment from mixing. Therefore, a partition is normally formed using a black radiation sensitive composition.

The board | substrate used for forming a color filter, a radiation light source, and the method and conditions of prebaking or postbaking are the same as that of the said 1st method. Thus, the film thickness of the pixel formed by the inkjet system is about the same as the height of a partition.

After forming a protective film on the pixel pattern obtained in this way as needed, a transparent conductive film is formed by sputtering. After forming a transparent conductive film, a spacer can also be formed and it can be set as a color filter. Although a spacer is normally formed using a radiation sensitive composition, it can also be set as the spacer (black spacer) which has light shielding property. In this case, although the coloring radiation sensitive composition containing a black coloring agent is used, the coloring composition of this invention can be used suitably also for formation of such a black spacer.

Since the color filter of this invention obtained in this way is extremely high, it is extremely useful for a color liquid crystal display element, a color image tube element, a color sensor, an organic electroluminescence display element, an electronic paper, etc.

Display element

The display element of this invention is equipped with the color filter of this invention. As a display element, a color liquid crystal display element, an organic electroluminescent display element, an electronic paper, etc. are mentioned.

The color liquid crystal display element provided with the color filter of this invention may be a transmissive type or a reflective type, and can take an appropriate structure. For example, the color filter may be formed on a substrate separate from the driving substrate on which the thin film transistor TFT is disposed so that the driving substrate and the substrate on which the color filter is formed may face each other through the liquid crystal layer. And a substrate on which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, an ITO (indium oxide doped tin) electrode or an IZO (mixture of indium oxide and zinc oxide) electrode. The formed substrate may take the structure which opposes through the liquid crystal layer. The latter structure can remarkably improve the aperture ratio, and has the advantage that a bright and high precision liquid crystal display element is obtained.

The color liquid crystal display device having the color filter of the present invention may include a backlight unit having a white LED as a light source in addition to a cold cathode fluorescent lamp (CCFL). As a white LED, for example, a white LED which combines a red LED, a green LED, and a blue LED to obtain white light by mixing, and a white LED and a blue LED which combines a blue LED, a red LED and a green phosphor to obtain white light by mixing White LED that obtains white light by mixing by combining red light emitting phosphor and green light emitting phosphor, white LED which obtains white light by mixing of blue LED and YAG fluorescent material, and blue LED, orange light emitting phosphor and green light emitting phosphor in combination The white LED which obtains white light, the ultraviolet-ray LED, the red light emitting fluorescent substance, the green light emitting fluorescent substance, and the blue light emitting fluorescent substance are combined, and the white LED etc. which obtain white light by mixing are mentioned.

The color liquid crystal display device including the color filter of the present invention includes a twisted nematic (TN) type, a super twisted nematic (STN) type, an in-plane switching switching (IPS) type, a vertical alignment (VA) type, and an optically compensated birefringence (OCB) type. Appropriate liquid crystal modes such as) can be applied.

Moreover, the organic electroluminescent display element provided with the color filter of this invention can employ | adopt an appropriate structure, for example, can take the structure disclosed by Unexamined-Japanese-Patent No. 11-307242.

Moreover, the electronic paper provided with the color filter of this invention can employ | adopt an appropriate structure, for example, can take the structure disclosed by Unexamined-Japanese-Patent No. 2007-41169.

<Examples>

EMBODIMENT OF THE INVENTION Hereinafter, embodiment of this invention is described in more detail, taking an example as an example. However, the present invention is not limited to the following examples.

<Synthesis of Binder Resin>

Synthesis Example 1

100 mass parts of propylene glycol monomethyl ether acetates were thrown into the flask provided with the cooling tube and the stirrer, and nitrogen-substituted. It heats at 80 degreeC, and 50 mass parts of propylene glycol monomethyl ether acetates, 15 mass parts of methacrylic acid, 3 mass parts of styrene, 5 mass parts of 2-hydroxyethyl methacrylates, and 19 mass parts of methyl methacrylates , 26 parts by mass of cyclohexyl methacrylate, 12 parts by mass of N-phenylmaleimide, 20 parts by mass of mono (2-methacryloyloxyethyl) succinic acid and 2,2'-azobis (2,4-dimethylvalero Nitrile) 6 parts by mass of a mixed solution was added dropwise over 1 hour, and maintained at this temperature to polymerize for 2 hours. Then, the binder resin solution was obtained by heating up the temperature of reaction solution at 90 degreeC and superposing | polymerizing for 1 hour. Obtained binder resin was Mw = 12,000, Mn = 7,000 and solid content concentration = 40 mass%. This binder resin is referred to as "binder resin (B-1)".

Synthesis Example 2

100 mass parts of propylene glycol monomethyl ether acetates were thrown into the flask provided with the cooling tube and the stirrer, and nitrogen-substituted. It heats at 80 degreeC, and at the same temperature, 50 mass parts of propylene glycol monomethyl ether acetates, 15 mass parts of methacrylic acid, 12 mass parts of styrene, 41 mass parts of benzyl methacrylate, and 15 mass of 2-hydroxyethyl methacrylate Part, 2 parts by mass of n-butyl methacrylate, 15 parts by mass of N-phenylmaleimide, and 0.5 parts by mass of 2,2'-azobis butyronitrile, pentaerythritol tetrakis (3-mercaptopropionate) 2 The mass solution of mixed solution was kept at 80 ° C and polymerized for 4 hours. Then, the binder resin solution (solid content concentration = 40 mass%) was obtained by heating up the temperature of reaction solution at 100 degreeC, and also polymerizing for 1 hour. Obtained binder resin was Mw = 24,000, Mn = 14,800 and solid content concentration = 40 mass%. Let this binder resin be "binder resin (B-2)."

Synthesis Example 3

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

Subsequently, 17 mass parts of methacrylic acid, 0.5 mass part of p-methoxyphenols, and 4.4 mass parts of tetrabutylammonium bromide were added to this reaction solution, and it was made to react at 120 degreeC for 9 hours. Furthermore, after adding 18.5 mass parts of succinic anhydrides, and making it react at 100 degreeC for 6 hours, it washes twice, maintaining the liquid temperature at 85 degreeC, and concentrates under reduced pressure, 40 mass% of binder resins (B-3) are carried out. The solution containing was obtained. Mw of this binder resin (B-3) was 7,800.

Preparation of Pigment Dispersion

Production Example 1

(A) As a coloring agent, C.I. Pigment Green 58 / C.I. Pigment Yellow 150 / C.I. Pigment Yellow Y138 = 52/36/12 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by BICKEMICAL COMPANY) as a dispersant (solid content concentration = 40% by mass), binder resin (B-1) solution 60 mass parts of propylene glycol monomethyl ether acetates were used as 14 mass parts and a solvent, it mixed and disperse | distributed with the bead mill and the pigment dispersion liquid (A-1) was produced.

Production Example 2

(A) As a coloring agent, C.I. Pigment Green 58 / C.I. Pigment Yellow Y138 = 47/53 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by BIC Chemistry Co., Ltd.) as a dispersant (solid content concentration = 40% by mass), and 14 parts by mass of a binder resin (B-1) solution To 60 parts by weight of propylene glycol monomethyl ether acetate was used as a solvent, followed by mixing and dispersing with a bead mill to prepare a pigment dispersion (A-2).

Production Example 3

(A) As a coloring agent, C.I. Pigment Red 254 / C.I. Pigment Red 177 / C.I. Pigment Yellow 150 = 23/70/7 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by Vicchemy Co., Ltd.) as a dispersant (solid content concentration = 40 mass%), binder resin (B-1) solution 60 mass parts of propylene glycol monomethyl ether acetates were used as 14 mass parts and a solvent, it mixed and disperse | distributed with the bead mill and the pigment dispersion liquid (A-3) was produced.

Production Example 4

(A) As a coloring agent, C.I. Pigment Red 254 / C.I. Pigment Red 177 / C.I. Pigment Yellow 139 = 15/77/8 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by BICKEMICAL COMPANY) as a dispersant (solid content concentration = 40% by mass), binder resin (B-1) solution 60 mass parts of propylene glycol monomethyl ether acetates were used as 14 mass parts and a solvent, it mixed and disperse | distributed with the bead mill and the pigment dispersion liquid (A-4) was produced.

Production Example 5

(A) As a coloring agent, C.I. Pigment Red 242 / C.I. Pigment Red 177 / C.I. Pigment Yellow 150 = 22/72/6 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by BICKEMICAL COMPANY) as a dispersant (solid content concentration = 40% by mass), binder resin (B-1) solution 60 mass parts of propylene glycol monomethyl ether acetates were used as 14 mass parts and a solvent, it mixed and disperse | distributed with the bead mill and the pigment dispersion liquid (A-5) was produced.

Production Example 6

(A) As a coloring agent, C.I. Pigment Red 254 / C.I. Pigment Red 177 = 55/45 (mass ratio) 15 parts by mass of a mixture, 11 parts by mass of BYK-LPN21116 (manufactured by BICKEMICAL COMPANY) as a dispersant (solid content concentration = 40% by mass), binder resin (B-1) solution 14 parts by mass Using a bead mill, 60 parts by mass of propylene glycol monomethyl ether acetate was used as the solvent to disperse and disperse the pigment dispersion (A-6).

Production Example 7

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

&Lt; Preparation and evaluation of colored composition >

 Example 1

Preparation of Coloring Composition

 950 parts by mass of the pigment dispersion (A-1), 95 parts by mass of the binder resin (B-2) solution as the binder resin (B), 7 parts by mass of the compound represented by the above formula (C-1) as the photopolymerization initiator (C), 70 parts by mass of caprolactone-modified dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd., trade name KAYARAD DPCA-60), (E) pentaerythritol tetrakis (3-mer) as a polyfunctional thiol Captopropionate) (4 parts by mass of SC Yuki Chemical Co., Ltd., PEMP II-20P), 0.7 parts by mass of DIC Corporation Megaface F-554 as a fluorine-based surfactant, 3-methoxybutyl acetate as a solvent. Was mixed and liquid coloring composition (S-1) of 20 mass% of solid content concentration was manufactured.

Evaluation of water splash

After apply | coating a liquid coloring composition (S-1) on a glass substrate using a spin coater, it prebaked for 4 minutes on the 90 degreeC hotplate, and formed the coating film of 2.0 micrometers in film thickness. Subsequently, after cooling this board | substrate to room temperature, the high pressure mercury lamp was used for the coating film on the board | substrate, and the radiation containing each wavelength of 365 nm, 405 nm, and 436 nm was exposed through the photomask at the exposure amount of 400 J / m <2>. Thereafter, the developer containing the aqueous solution of 0.04% by mass potassium hydroxide at 23 ° C. was developed at a pressure of 1.5 kgf / cm 2 (nozzle diameter of 1 mm) with respect to the coating on the substrate. The shower phenomenon was performed by discharging until it passed. Subsequently, rinse treatment was performed by discharging ultrapure water at a rinse pressure of 1.5 kgf / cm 2 (nozzle diameter 1 mm) for 60 seconds to form a dot pattern of 200 μm × 200 μm.

After removing water on the surface of the substrate on which the dot pattern was formed by air blow, 20 dot patterns were observed using an optical microscope. The case where water stain was observed in 10 or more patterns among 20 patterns was evaluated as "(circle)" and the case where water stain was observed in 1-9 patterns as "(triangle | delta)" and the case where no water stain was observed at all as "(circle)". The evaluation results are shown in Table 2.

Cloudiness rating

After apply | coating a liquid coloring composition (S-1) on a glass substrate using a spin coater, it prebaked for 1 minute on the 90 degreeC hotplate, and formed the coating film of 2.5 micrometers in thickness. Subsequently, after cooling this board | substrate to room temperature, the radiation containing each wavelength of 365 nm, 405 nm, and 436 nm was exposed by the exposure amount of 600 J / m <2>, without passing through a photomask using the high pressure mercury lamp for the coating film on the board | substrate. Then, the shower image development was performed by discharging the developing solution containing the 0.04 mass% sodium carbonate aqueous solution of 23 degreeC with the developing pressure of 1 kgf / cm <2> (nozzle diameter 1mm) with respect to the coating film on a board | substrate. The obtained substrate was illuminated with a sodium lamp, and the presence or absence of clouding was observed. The thing with no blur was evaluated as "(circle)" and the thing with a blur as "x". The evaluation results are shown in Table 2.

Post On baking  Evaluation of luminance decrease by

After apply | coating a liquid coloring composition (S-1) on a glass substrate using a spin coater, it prebaked for 1 minute on a 90 degreeC hotplate, and formed the coating film of 2.5 micrometers in thickness. Subsequently, after cooling this board | substrate to room temperature, using the high pressure mercury lamp for the coating film on a board | substrate, the radiation containing each wavelength of 365 nm, 405 nm, and 436 nm was exposed by the exposure amount of 600 J / m <2>, without passing through a photomask. It was. Then, the shower image development was performed by discharging the developing solution containing the 0.04% potassium hydroxide aqueous solution of 23 degreeC with the developing pressure of 1 kgf / cm <2> (nozzle diameter 1mm) with respect to the coating film on a board | substrate. Then, after wash | cleaning these board | substrates with ultrapure water and air drying, the green cured film was produced by post-baking for 20 minutes in a 230 degreeC clean oven.

 About the cured film after image development and post-baking, the chromaticity in the CIE colorimeter was measured in C light source and 2 degree visual field using the color analyzer (MCPD2000 by Otsuka Denshi Co., Ltd.). From the measurement result, "(circle)" and the case where 2.5% or more of the case where the fall of the brightness | luminance Y before and after postbaking were less than 2.5% were evaluated as "x". In addition, it is meant that the lower the rate of decrease of luminance Y is better. The evaluation results are shown in Table 2.

Evaluation of heat resistance

The board | substrate obtained by said "evaluation of the brightness fall by post baking" was further heated at 250 degreeC for 30 minutes. And the surface of the board | substrate was observed with the optical microscope which the eyepiece magnification is 10 times, and the objective lens magnification is 10 times. "○" for the case of 3 or less foreign substances confirmed in 1 visual field, "△" for the case of 4 or more 9 foreign substances confirmed in 1 visual field, and "x" for the case of 10 or more foreign substances confirmed in 1 visual field. Evaluated. In addition, it means that the one with less number of a foreign material is favorable. The evaluation results are shown in Table 2.

Examples 2 to 32 and Comparative Examples 1 to 12

In Example 1, except having changed into the pigment dispersion liquid shown in Table 1, binder resin, etc., liquid coloring compositions (S-2)-(S-44) were produced like Example 1 similarly.

Next, each evaluation was performed like Example 1 except having used liquid coloring compositions (S-2)-(S-44) instead of liquid coloring composition (S-1), respectively. The evaluation results are shown in Table 2.

Each component in Table 1 is as follows.

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

 C-2: ethanone, 1- [9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl]-, 1- (O-acetyl oxime) (trade name IRGACURE OX02, BASF (BASF) Company production)

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

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

 C-5: 2, 4- diethyl thioxanthone (made by Nippon Kayaku Co., Ltd.)

 C-6: 4,4'-bis (diethylamino) benzophenone (made by Hodogaya Chemical Corporation)

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

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

 E-1: pentaerythritol tetrakis (3-mercaptopropionate) (brand name PEMP II-20P, product made by SC Yugaku Co., Ltd.)

 E-2: silsesquioxane polyfunctional thiol (trade name Conposeran HBSQ105-9, manufactured by Arakawa Chemical Industries, Ltd.)

Claims (8)

(A) a coloring agent, (B) binder resin, (C) photoinitiator represented by following General formula (1), (D) compound which has two or more polymerizable unsaturated bonds, and (E) polyfunctional thiol Coloring composition.

In 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, provided that some or all of the hydrogen atoms of the phenyl group have May be substituted with 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, a phenyl group or a naphthyl group having 3 to 20 carbon atoms,
R ⁵ represents a phenyl group, tolyl group, xylyl group, naphthyl group, anthryl group, phenanthryl group, 9-fluorenyl group, 2-furyl group or 2-thienyl group, provided that some of the hydrogen atoms of these groups Or all may be substituted with 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 whose R <^3> is a C3-C8 cycloalkyl group. The coloring composition of Claim 1 or 2 which contains a zinc halide phthalocyanine pigment as said (A) coloring agent, and the content rate of the said (A) coloring agent is 30-60 mass% in total solid. The C.I. method according to claim 1 or 2, wherein the colorant (A) is used. Pigment Red 177, C.I. Pigment Red 242 and C.I. The coloring composition containing 2 or more types chosen from the group which consists of Pigment Red 254, and the content rate of the said (A) coloring agent is 30-60 mass% in total solid. The coloring composition according to any one of claims 1 to 4, wherein the (B) binder resin contains a polymer having an acidic functional group and a polymerizable unsaturated group. The coloring composition of any one of Claims 1-5 which further contains a biimidazole type photoinitiator. The color filter provided with the colored layer formed using the coloring composition of any one of Claims 1-6. The display element provided with the color filter of Claim 7.