JP5196048B2 - Radiation-sensitive composition for forming colored layer, color filter, and color liquid crystal display element - Google Patents

Description

  The present invention relates to a radiation-sensitive composition for forming a colored layer, a color filter, and a color liquid crystal display element. More specifically, the present invention relates to a color filter used for a transmissive or reflective color liquid crystal display device, a color imaging tube element, and the like. The present invention relates to a radiation-sensitive composition used for forming a useful colored layer, a color filter including a colored layer formed using the radiation-sensitive composition, and a color liquid crystal display element including the color filter.

  As a method of forming a color filter using a colored radiation-sensitive resin composition, a coating film of a colored radiation-sensitive resin composition is formed on a substrate or a substrate on which a light-shielding layer having a desired pattern is formed in advance. Radiation is irradiated through a photomask having a desired pattern shape (hereinafter referred to as “exposure”), development with an alkali developer is performed to dissolve and remove unexposed portions, and then post is performed using a clean oven or a hot plate. A method of obtaining pixels of each color by baking (for example, see Patent Documents 1 and 2) is known.

In recent years, the concentration of pigments contained in colored radiation-sensitive compositions tends to become higher with the increase in color purity of color liquid crystal display devices, so that residues on unexposed substrates or light-shielding layers during development And the problem of soiling has become prominent. Furthermore, when the density | concentration of the pigment contained in a coloring radiation sensitive composition becomes high, there exists a tendency for the solubility with respect to the alkali developing solution of a coating film to fall remarkably. For this reason, during development by the shower development method, the unexposed coating film that has been peeled and removed once floats without completely dissolving in the developing tank, and reattaches as a foreign matter on the color filter, resulting in a product yield. This is a major factor of decline.
In addition, the pigment contained in the colored radiation-sensitive composition is becoming more and more finely divided as the color liquid crystal display device has a high contrast. However, in order to disperse the finely divided pigment stably, the amine value of It is becoming effective to use high dispersants. However, when a dispersant having a high amine value is used, development itself with an alkali developer becomes difficult, so that it has not been put into practical use.
Therefore, there is a strong demand for a radiation-sensitive resin composition for color filters that can cope with various problems that arise with the recent demands for higher color purity and higher contrast.

On the other hand, a polyfunctional monomer containing a carboxyl group is used, for example, as disclosed in Patent Document 3, for the problem of residue and background stains on the unexposed substrate or the light shielding layer during development. It is known to be effective. However, in the monoesterified product containing a free carboxyl group of pentaerythritol triacrylate and succinic acid disclosed in Patent Document 3, coloring at a high pigment concentration such that the pigment content is 30% by weight or more in the total solid content When applied to a radiation-sensitive composition, there has been a problem that the surface smoothness of the pattern is significantly impaired due to insufficient curing of the film, resulting in poor alignment of the liquid crystal.
Further, for example, as disclosed in Patent Document 4, a curable resin composition for a colored pattern is obtained by including a photocurable compound having one or more acidic functional groups and three or more photocurable functional groups. It is known that the developability of the product is improved. However, any effective solution is disclosed for the above problems of the red, green or blue pattern resin composition having a high pigment concentration such that the pigment content is 30% by weight or more in the total solid content. It has not been.
Thus, there is a strong demand for the development of a further improved colored radiation-sensitive resin composition that satisfies various requirements regarding developability and product yield during the manufacture of color filters in recent years, and also has good pattern surface smoothness. .

JP-A-2-144502 JP-A-3-53201 Japanese Patent Laid-Open No. 10-332929 JP 2004-287230 A

  An object of the present invention is to provide a colored layer capable of forming a color filter that does not cause residue or background staining even at a high pigment concentration with a high product yield, and can form a pattern having sufficient surface smoothness. It is providing the radiation sensitive resin composition for formation.

The present invention, first,
(A) At least one pigment selected from the group consisting of a red pigment, a green pigment and a blue pigment, (B) a dispersant, (C) an alkali-soluble resin, (D) a polyfunctional compound represented by the following formula (1) And (E) a radiation-sensitive resin composition for forming a colored layer containing a photopolymerization initiator, wherein (A) the content of the pigment is 30 to 60% by weight in the total solid content It consists of the radiation sensitive resin composition for colored layer formation characterized by the above-mentioned.

（式中、Ｒ₁は水素原子またはメチル基を示し、Ｒ₂はメチレン基、炭素数２〜８の直鎖または分岐鎖のアルキレン基、直鎖または分岐鎖のアルケニレン基、置換基を有していてもよいフェニレン基、置換基を有していてもよいシクロヘキシレン基および置換基を有していてもよいシクロヘキシレン基の一部が不飽和結合である基よりなる群から選ばれる基を示す。）

(Wherein R ₁ represents a hydrogen atom or a methyl group, R ₂ has a methylene group, a linear or branched alkylene group having 2 to 8 carbon atoms, a linear or branched alkenylene group, and a substituent. A group selected from the group consisting of a phenylene group that may be substituted, a cyclohexylene group that may have a substituent, and a group in which part of the cyclohexylene group that may have a substituent is an unsaturated bond; Show.)

The present invention secondly,
It comprises a color filter provided with a colored layer formed using the radiation-sensitive resin composition for forming the colored layer.

Third, the present invention
A color liquid crystal display device including the color filter;

  The radiation-sensitive resin composition for forming a colored layer according to the present invention does not produce residue or background stains and has sufficient surface smoothness even when the concentration of the pigment contained in the colored radiation-sensitive composition is high. A color filter having the same can be formed. Furthermore, the solubility of the coating film in an alkaline developer is high, and a high product yield can be achieved even for development by a shower development method.

Hereinafter, the present invention will be described in detail.
Radiation-sensitive resin composition for forming colored layer- (A) pigment-
The pigment in the present invention is not particularly limited as long as it contains at least one selected from a red pigment, a green pigment and a blue pigment, and may be an organic pigment or an inorganic pigment. Of these, organic pigments are particularly preferred because color filters are required to have high-purity and highly transparent color development and heat resistance.
Examples of the organic pigment include compounds classified as pigments in the color index, and specifically those having a color index (CI) number as shown below.

As a red pigment, C.I. I. Pigment red 1, C.I. I. Pigment red 2, C.I. I. Pigment red 5, C.I. I. Pigment red 17, C.I. I. Pigment red 31, C.I. I. Pigment red 32, C.I. I. Pigment red 41, C.I. I. Pigment red 122, C.I. I. Pigment red 123, C.I. I. Pigment red 144, C.I. I. Pigment red 149, C.I. I. Pigment red 166, C.I. I. Pigment red 168, C.I. I. Pigment red 170, C.I. I. Pigment red 171, C.I. I. Pigment red 175, C.I. I. Pigment red 176, C.I. I. Pigment red 177, C.I. I. Pigment red 178, C.I. I. Pigment red 179, C.I. I. Pigment red 180, C.I. I. Pigment red 185, C.I. I. Pigment red 187, C.I. I. Pigment red 202, C.I. I. Pigment red 206, C.I. I. Pigment red 207, C.I. I. Pigment red 209, C.I. I. Pigment red 214, C.I. I. Pigment red 220, C.I. I. Pigment red 221, C.I. I. Pigment red 224, C.I. I. Pigment red 242, C.I. I. Pigment red 243, C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 262, C.I. I. Pigment red 264, C.I. I. Pigment red 272;

As a green pigment, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 58;
As a blue pigment, C.I. I. Pigment blue 15, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 60, C.I. I. Pigment blue 80;
In preparing a radiation-sensitive resin composition for forming a colored layer of red, green or blue, it is common to adjust the color using a yellow pigment, a purple pigment or the like. Specific examples of organic pigments such as yellow and purple include those having the following color index (CI) numbers.

C. I. Pigment yellow 12, C.I. I. Pigment yellow 13, C.I. I. Pigment yellow 14, C.I. I. Pigment yellow 17, C.I. I. Pigment yellow 20, C.I. I. Pigment yellow 24, C.I. I. Pigment yellow 31, C.I. I. Pigment yellow 55, C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 93, C.I. I. Pigment yellow 109, C.I. I. Pigment yellow 110, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 153, C.I. I. Pigment yellow 154, C.I. I. Pigment yellow 155, C.I. I. Pigment yellow 166, C.I. I. Pigment yellow 168, C.I. I. Pigment yellow 211;
C. I. Pigment orange 5, C.I. I. Pigment orange 13, C.I. I. Pigment orange 14, C.I. I. Pigment orange 24, C.I. I. Pigment orange 34, C.I. I. Pigment orange 36, C.I. I. Pigment orange 38, C.I. I. Pigment orange 40, C.I. I. Pigment orange 43, C.I. I. Pigment orange 46, C.I. I. Pigment orange 49, C.I. I. Pigment orange 61, C.I. I. Pigment orange 64, C.I. I. Pigment orange 68, C.I. I. Pigment orange 70, C.I. I. Pigment orange 71, C.I. I. Pigment orange 72, C.I. I. Pigment orange 73, C.I. I. Pigment orange 74;

C. I. Pigment violet 1, C.I. I. Pigment violet 19, C.I. I. Pigment violet 23, C.I. I. Pigment violet 29, C.I. I. Pigment violet 32, C.I. I. Pigment violet 36, C.I. I. Pigment violet 38;
C. I. Pigment brown 23, C.I. I. Pigment brown 25;
C. I. Pigment black 1, C.I. I. Pigment Black 7.
These organic pigments can be used alone or in admixture of two or more.

  Among these organic pigments, C.I. I. Pigment red 177, C.I. I. Pigment red 242, C.I. I. Pigment red 254, C.I. I. Pigment green 7, C.I. I. Pigment green 36, C.I. I. Pigment green 58, C.I. I. Pigment blue 15: 3, C.I. I. Pigment blue 15: 4, C.I. I. Pigment blue 15: 6, C.I. I. Pigment blue 60, C.I. I. Pigment blue 80, C.I. I. Pigment yellow 83, C.I. I. Pigment yellow 138, C.I. I. Pigment yellow 139, C.I. I. Pigment yellow 150, C.I. I. Pigment yellow 180, C.I. I. At least one selected from the group of Pigment Violet 23 is preferred.

  In the present invention, the organic pigment can be purified and used by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof.

Examples of the inorganic pigment include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean curd (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, and chromium oxide. Examples include green, cobalt green, amber, titanium black, synthetic iron black, and carbon black.
These inorganic pigments can be used alone or in admixture of two or more.

  Furthermore, in the present invention, if necessary, one or more dyes or natural pigments can be used in combination with the pigment.

  In the present invention, the pigment can be used by modifying the particle surface with a polymer, if desired. Examples of the polymer that modifies the particle surface of the pigment include polymers described in JP-A-8-259876, various commercially available polymers or oligomers for dispersing pigments, and the like.

In the present invention, the (A) pigment is usually contained in an amount of 30 to 60% by weight, preferably 30 to 50% by weight, based on the total solid content of the composition of the present invention, from the viewpoint of obtaining sufficient color purity and developability. Here, solid content is components other than the solvent mentioned later.
-(B) Dispersant-

  As the dispersing agent (B) in the present invention, for example, an appropriate dispersing agent such as cationic, anionic, nonionic or amphoteric can be used, but a color having a high contrast ratio exceeding 1000: 1. In order to stably disperse the atomized pigment that realizes the liquid crystal display device, a dispersant having an amine value (unit: mgKOH / g; the same applies hereinafter) of 70 to 400 (hereinafter referred to as “high amine value dispersant”). .) Is preferable, and it is more preferable to include a dispersant of 70 to 200. Here, the amine value represents the number of mg of KOH equivalent to HCl required to neutralize 1 g of the solid content of the dispersant.

  Dispersbyk-106 (nonvolatile component = 85%, amine value = 74), Big Chemie (BYK), Disperbyk-108 (nonvolatile component = 97%, amine value = 71, big chemi ( BYK)), Disperbyk-140 (nonvolatile component = 52%, amine value = 76, manufactured by BYK Chemy (BYK)), Disperbyk-142 (nonvolatile component = 60%, amine value = 43, manufactured by BYK (BYK)) ), Disperbyk-145 (nonvolatile component = 100%, amine value = 71, manufactured by Big Chemie (BYK)), Disperbyk-2150 (nonvolatile component = 52%, amine value = 57, manufactured by Big Chemie (BYK)), Addisper PB -711 (nonvolatile component = 40%, amine value = 45, Ajinomoto Aintekuno Co., Ltd.), and the like.

Examples of the dispersant other than the high amine value dispersant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether; polyoxyethylene n-octylphenyl ether, polyoxy Polyoxyethylene alkyl phenyl ethers such as ethylene n-nonylphenyl ether; polyethylene glycol dilaurate, polyethylene glycol difatty acid ester such as polyethylene glycol distearate; sorbitan fatty acid ester; fatty acid modified polyester; tertiary amine modified polyurethane; In addition, the following product names are KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), F Top (Tochem Proda) Manufactured by Tsutsu Co., Ltd.), MegaFac (manufactured by Dainippon Ink & Chemicals, Inc.), Florard (manufactured by Sumitomo 3M), Asahi Guard, Surflon (manufactured by Asahi Glass Co., Ltd.) 103, -110, -111, -160, -161, -162, -163, -164, -165, -166, -170, -182, -2000, -2001, -2020 (above, manufactured by BYK), Solsperse S5000, 12000, 17000, 20000, 22000, 24000, 24000GR, 26000, 27000, 28000 (above, Louvre) Zole Co., Ltd.), EFKA 46, 47, (above, manufactured by EFKA Chemicals Co., Ltd.); Ajisper PB-821, B-822 (manufactured by Ajinomoto Fine-Techno Co.), and the like.
In this invention, a dispersing agent can be used individually or in mixture of 2 or more types.

  The content of the dispersant in the present invention (in terms of solid content) is preferably 1 to 60 parts by weight, more preferably 100 parts by weight of the pigment (A) from the viewpoint of storage stability and developability of the composition. 3 to 50 parts by weight.

-(C) Alkali-soluble resin-
As the (C) alkali-soluble resin in the present invention, (A) a developer that acts as a binder for the pigment and that is used in a developing step for producing a color filter, particularly preferably soluble in an alkali developer. If it has, it will not specifically limit. Among them, an alkali-soluble resin having a carboxyl group is preferable, and in particular, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter referred to as “carboxyl group-containing unsaturated monomer”) and other co-polymers. A copolymer (hereinafter referred to as “carboxyl group-containing copolymer”) with a polymerizable ethylenically unsaturated monomer (hereinafter referred to as “copolymerizable unsaturated monomer”) is preferred.

As the carboxyl group-containing unsaturated monomer, for example,
Unsaturated carboxylic acids such as (meth) acrylic acid, crotonic acid, α-chloroacrylic acid, cinnamic acid;
Unsaturated dicarboxylic acids such as maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride, mesaconic acid or the like;
A trivalent or higher unsaturated polycarboxylic acid or anhydride thereof;
Mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl];
Examples thereof include mono (meth) acrylates of polymers having a carboxy group and a hydroxyl group at both ends, such as ω-carboxypolycaprolactone mono (meth) acrylate.
Of these carboxyl group-containing unsaturated monomers, succinic acid mono (2-acryloyloxyethyl) and phthalic acid mono (2-acryloyloxyethyl) are respectively light ester HOA-MS and light ester HOA-MPE (above). , Manufactured by Kyoeisha Chemical Co., Ltd.).
The said carboxyl group-containing unsaturated monomer can be used individually or in mixture of 2 or more types.

Examples of the copolymerizable unsaturated monomer include:
Maleimide;
N-phenylmaleimide, N-o-hydroxyphenylmaleimide, Nm-hydroxyphenylmaleimide, Np-hydroxyphenylmaleimide, N-benzylmaleimide, N-cyclohexylmaleimide, N-succinimidyl-3-maleimidobenzoate, N- N-substituted maleimides such as succinimidyl-4-maleimidobutyrate, N-succinimidyl-6-maleimidocaproate, N-succinimidyl-3-maleimidopropionate, N- (acridinyl) maleimide;
Styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, p-hydroxy-α-methylstyrene Aromatic vinyl compounds such as o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether, p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether;
Indenes such as indene and 1-methylindene;

Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate, n-butyl (meth) acrylate, i-butyl (meth) acrylate, sec-butyl (meth) Acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl ( (Meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, phenyl (meth) acrylate 2-methoxyethyl (meth) acrylate, 2-phenoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytriethylene glycol (meth) acrylate, methoxypropylene glycol (meth) acrylate, methoxydi Propylene glycol (meth) acrylate, isobornyl (meth) acrylate, tricyclo [5.2.1.02,6] decan-8-yl (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, glycerol Unsaturated carboxylic esters such as mono (meth) acrylate, 4-hydroxyphenyl (meth) acrylate, EO-modified (meth) acrylate of paracumylphenol;

2-aminoethyl (meth) acrylate, 2-dimethylaminoethyl (meth) acrylate, 2-aminopropyl (meth) acrylate, 2-dimethylaminopropyl (meth) acrylate, 3-aminopropyl (meth) acrylate, 3-dimethyl Unsaturated carboxylic acid aminoalkyl esters such as aminopropyl (meth) acrylate;
Unsaturated carboxylic acid glycidyl esters such as glycidyl (meth) acrylate;
Carboxylic acid vinyl esters such as vinyl acetate, vinyl propionate, vinyl butyrate, vinyl benzoate;
Other unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether;
Vinyl cyanide compounds such as (meth) acrylonitrile, α-chloroacrylonitrile, vinylidene cyanide;
Unsaturated amides such as (meth) acrylamide, α-chloroacrylamide, N-2-hydroxyethyl (meth) acrylamide;
Aliphatic conjugated dienes such as 1,3-butadiene, isoprene, chloroprene;
Examples thereof include a macromonomer having a mono (meth) acryloyl group at the end of a polymer molecular chain such as polystyrene, polymethyl (meth) acrylate, poly-n-butyl (meth) acrylate, and polysiloxane.
These copolymerizable unsaturated monomers can be used alone or in admixture of two or more.

  The carboxyl group-containing copolymer in the present invention includes (c1) (meth) acrylic acid as an essential component, and optionally succinic acid mono [2- (meth) acryloyloxyethyl] and / or ω-carboxypolycacrolactone. Carboxyl group-containing unsaturated monomer containing mono (meth) acrylate, (c2) N-substituted maleimide, (c3) styrene, α-methylstyrene, p-hydroxy-α-methylstyrene, methyl (meta ) Acrylate, n-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, allyl (meth) acrylate, benzyl (meth) acrylate, glycerol mono (meth) acrylate, 4-hydroxy Phenyl (meth) acrylate, paracumyl fe Copolymer with at least one other copolymerizable unsaturated monomer selected from the group of EO-modified (meth) acrylate, polystyrene macromonomer and polymethylmethacrylate macromonomer (hereinafter referred to as “carboxyl group-containing”) Copolymer (C1) ”) is preferred.

As a preferable specific example of the carboxyl group-containing copolymer (C1),
(Meth) acrylic acid / N-phenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / Nm-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / Np-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-cyclohexylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / α-methylstyrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / n-butyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / 2-ethylhexyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / p-hydroxy-α-methylstyrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / n-butyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / 2-ethylhexyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / benzyl (meth) acrylate / glycerol mono (meth) acrylate copolymer,
(Meth) acrylic acid / Np-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate / glycerol mono (meth) acrylate copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / phenyl (meth) acrylate / 2-hydroxyethyl (meth) acrylate / polystyrene macromonomer copolymer,
(Meth) acrylic acid / N-phenylmaleimide / styrene / phenyl (meth) acrylate / 2-hydroxyethyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer,
(Meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / N-phenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / Np-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / N-phenylmaleimide / styrene / allyl (meth) acrylate copolymer,
(Meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / N-cyclohexylmaleimide / styrene / allyl (meth) acrylate copolymer,
(Meth) acrylic acid / succinic acid mono [2- (meth) acryloyloxyethyl] / N-cyclohexylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / ω-carboxypolycacrolactone mono (meth) acrylate / Nm-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / ω-carboxypolycacrolactone mono (meth) acrylate / Np-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / ω-carboxypolycacrolactone mono (meth) acrylate / N-phenylmaleimide / styrene / benzyl (meth) acrylate / glycerol mono (meth) acrylate copolymer,
(Meth) acrylic acid / ω-carboxypolycacrolactone mono (meth) acrylate / Np-hydroxyphenylmaleimide / styrene / benzyl (meth) acrylate / glycerol mono (meth) acrylate copolymer and the like.

Moreover, as a carboxyl group-containing copolymer other than the carboxyl group-containing copolymer (C1), for example,
(Meth) acrylic acid / methyl (meth) acrylate copolymer,
(Meth) acrylic acid / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate copolymer,
(Meth) acrylic acid / methyl (meth) acrylate / polystyrene macromonomer copolymer,
(Meth) acrylic acid / methyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer,
(Meth) acrylic acid / benzyl (meth) acrylate / polystyrene macromonomer copolymer,
(Meth) acrylic acid / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer,
(Meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polystyrene macromonomer copolymer,
(Meth) acrylic acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer and the like.

  In the carboxyl group-containing copolymer, the copolymerization ratio of the carboxyl group-containing unsaturated monomer is preferably 5 to 50% by weight, more preferably 10 to 40% by weight. In this case, when the copolymerization ratio is less than 5% by weight, the solubility of the resulting radiation-sensitive composition in an alkali developer tends to be reduced, whereas when it exceeds 50% by weight, the solubility in an alkali developer is low. When the development is performed with an alkaline developer, the pixel tends to drop off from the substrate or the surface of the pixel becomes rough.

  In the present invention, for example, an unsaturated isocyanate such as 2- (meth) acryloyloxyethyl isocyanate is added to a carboxyl group-containing copolymer obtained by copolymerizing an unsaturated compound having a hydroxyl group such as 2-hydroxyethyl (meth) acrylate. By reacting the narate compound, a polymerizable unsaturated bond can be introduced into the side chain of the carboxyl group-containing copolymer.

The weight average molecular weight in terms of polystyrene (hereinafter referred to as “Mw”) measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) of the carboxyl group-containing copolymer in the present invention is usually 1,000 to 45,000. 000, preferably 3,000 to 20,000.
In addition, the number average molecular weight in terms of polystyrene (hereinafter referred to as “Mn”) measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) of the carboxyl group-containing copolymer in the present invention is usually from 1,000 to 1,000. 45,000, preferably 3,000 to 20,000.
In this case, if the Mw is less than 1,000, the remaining film ratio of the resulting coating may be reduced, the pattern shape, heat resistance, etc. may be impaired, and electrical characteristics may be deteriorated. If it exceeds 000, the resolution may be reduced, the pattern shape may be impaired, and dry foreign matter may be easily generated during application by the slit nozzle method.

  The carboxyl group-containing copolymer may be prepared by, for example, combining a carboxyl group-containing unsaturated monomer and a copolymerizable unsaturated monomer with 2,2′-azobisisobutyronitrile, 2,2 ′ in a suitable solvent. -It can be produced by polymerization in the presence of a radical polymerization initiator such as azobis (2,4-dimethylvaleronitrile) or 2,2'-azobis (4-methoxy-2,4-dimethylvaleronitrile). .

The carboxyl group-containing copolymer can be purified through a reprecipitation method using two or more organic solvents having different polarities after radical polymerization of the unsaturated monomer as described above. That is, after removing insoluble impurities from the solution in a good solvent after polymerization by filtration or centrifugation as necessary, a large amount (usually 5 to 10 times the volume of the polymer solution) of a precipitant (poor) Purification by pouring into the solvent) and reprecipitation of the copolymer. At that time, of the impurities remaining in the polymer solution, impurities soluble in the precipitant remain in the liquid phase and are separated from the purified copolymer (B1) and the like.
Examples of the good solvent / precipitant combination used in this reprecipitation method include diethylene glycol monomethyl ether acetate / n-hexane, methyl ethyl ketone / n-hexane, diethylene glycol monomethyl ether acetate / n-heptane, methyl ethyl ketone / n-heptane, and the like. Can be mentioned.

  In addition, the carboxyl group-containing copolymer includes, for example, each unsaturated compound as a constituent component of 2,2′-azobisisobutyronitrile, 2,2′-azobis (2,4-dimethylvaleronitrile). , Radical polymerization initiators such as 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), and pyrazole-1-dithiocarboxylic acid cyano (dimethyl) methyl ester, pyrazole-1-dithiocarboxylate benzyl Ester, tetraethylthiuram disulfide, bis (pyrazol-1-ylthiocarbonyl) disulfide, bis (3-methyl-pyrazol-1-ylthiocarbonyl) disulfide, bis (4-methyl-pyrazol-1-ylthiocarbonyl) disulfide, Bis (5-methyl-pyrazol-1-ylthiocarbonyl) disulfur Bis (3,4,5-trimethyl-pyrazol-1-ylthiocarbonyl) disulfide, bis (pyrrol-1-ylthiocarbonyl) disulfide, bis (thiobenzoyl) disulfide, bis (n-octylsulfanylthiocarbonyl) ) In the presence of a molecular weight control agent that acts as an iniferter such as disulfide or bis (n-dodecylsulfanylthiocarbonyl) disulfide, the reaction temperature is usually 0 to 150 ° C., preferably 50 to 120 ° C. in an inert solvent. It can be produced by living radical polymerization.

In this invention, alkali-soluble resin can be used individually or in mixture of 2 or more types.
The content of the alkali-soluble resin in the present invention is preferably 10 to 1,000 parts by weight, more preferably 20 to 500 parts by weight with respect to 100 parts by weight of the (A) pigment. In this case, if the content of the alkali-soluble resin is less than 10 parts by weight, for example, the alkali developability may be reduced, or background stains or film residues may be generated on the unexposed part of the substrate or the light shielding layer. When the amount exceeds 1,000 parts by weight, the pigment concentration is relatively lowered, and it may be difficult to achieve the target color concentration as a thin film.

-(D) polyfunctional monomer-
The polyfunctional monomer in the present invention contains a polyfunctional monomer represented by the formula (1) (hereinafter referred to as “carboxyl group-containing pentafunctional monomer”).
In formula (1), examples of the linear or branched alkylene group having 2 to 8 carbon atoms represented by R ₂ include an ethylene group, a propylene group, a trimethylene group, a tetramethylene group, a pentamethylene group, and a hexamethylene group. Among them, an alkylene group having 2 to 4 carbon atoms is preferable. Examples of the linear or branched alkenylene group having 2 to 8 carbon atoms include a vinyl group and a 1-methylidene-ethylene group (—C (═CH ₂ ) CH ₂ —). Examples of the group in which a part of the cyclohexylene group is an unsaturated bond include a cyclohexenylene group. Examples of the group that can be substituted with a phenylene group, a cyclohexylene group, and an unsaturated cyclohexylene group include an alkyl group having 1 to 4 carbon atoms such as a methyl group and an ethyl group, a halogen atom, and an alkoxy group having 1 to 4 carbon atoms. Is mentioned.
In formula (1), R ₂ is preferably a methylene group or an alkylene group having 2 to 4 carbon atoms, particularly preferably an ethylene group.

Specific examples of the carboxyl group-containing pentafunctional monomer include dipentaerythritol penta (meth) acrylate, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, itaconic acid, terephthalic acid, hexahydro And monoesterified products with dicarboxylic acids such as phthalic acid.
Among these carboxyl group-containing pentafunctional monomers, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and a mixture of monoesterified products with dipentaerythritol pentaacrylate and succinic acid are TO-1382 (Toagosei ( (Commercially available) under the trade name.
The carboxyl group-containing pentafunctional monomer can be used alone or in admixture of two or more.

In the present invention, other polyfunctional monomers can be used in combination with the carboxyl group-containing pentafunctional monomer. Other polyfunctional monomers include, for example,
Di (meth) acrylates of alkylene glycols such as ethylene glycol and propylene glycol;
Di (meth) acrylates of polyalkylene glycols such as polyethylene glycol and polypropylene glycol;
Poly (meth) acrylates of trihydric or higher polyhydric alcohols such as glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol;
Oligo (meth) acrylates such as polyester, epoxy resin, urethane resin, alkyd resin, silicone resin, spirane resin;
Di (meth) acrylates of both terminal hydroxylated polymers such as both terminal hydroxypoly-1,3-butadiene, both terminal hydroxypolyisoprene and both terminal hydroxypolycaprolactone, and tris [2- (meth) acryloyloxyethyl] A phosphate etc. can be mentioned.

Among these other polyfunctional monomers, poly (meth) acrylates of trihydric or higher polyhydric alcohols, specifically, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, Pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, etc. are preferred, especially trimethylolpropane triacrylate, Pentaerythritol triacrylate and dipentaerythritol hexaacrylate Degree is high, excellent surface smoothness of the colored layer, and the substrate on and stain on the light-shielding layer in the unexposed portion, are unlikely to generate film residue and the like.
These other polyfunctional monomers can be used alone or in admixture of two or more.

  The total content of the (D) carboxyl group-containing pentafunctional monomer and other polyfunctional monomers in the present invention is usually 5 to 500 parts by weight per 100 parts by weight of the (C) alkali-soluble resin. The amount is preferably 20 to 300 parts by weight. In this case, if the content of the polyfunctional monomer is too small, the strength and surface smoothness of the colored layer may be lowered. On the other hand, if the content is too large, for example, alkali developability may be lowered, or unexposed areas. There is a risk that background contamination, film residue, etc. are likely to occur on the substrate or the light shielding layer.

  In the present invention, the content ratio of the carboxyl group-containing pentafunctional monomer is usually 20 to 80% by weight relative to the total of the carboxyl group-containing pentafunctional monomer and other polyfunctional monomers. It is preferably 30 to 70% by weight. In this case, if the content ratio of the carboxyl group-containing pentafunctional monomer is too small, the desired effect cannot be obtained. On the other hand, if the content ratio is too large, the surface smoothness of the resulting colored layer may be insufficient.

-(E) Photopolymerization initiator-
The photopolymerization initiator in the present invention generates an active species capable of initiating polymerization of the (D) polyfunctional monomer by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray. A compound.
Examples of such photopolymerization initiators include acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, onium salt compounds, benzoin compounds, benzophenone compounds, α-diketone compounds. , Polynuclear quinone compounds, xanthone compounds, diazo compounds, imide sulfonate compounds, and the like. These compounds are components that generate active radicals or active acids or both active radicals and active acids upon exposure.

  In the present invention, the photopolymerization initiator can be used alone or in admixture of two or more. As the photopolymerization initiator in the present invention, an acetophenone compound, a biimidazole compound, a triazine compound, At least one selected from the group of O-acyloxime compounds is preferred.

  In this invention, general content of a photoinitiator is 0.01-120 weight part normally with respect to 100 weight part of (D) polyfunctional monomers, Preferably it is 1-100 weight part. is there. In this case, if the content of the photopolymerization initiator is too small, curing by exposure may be insufficient, and it may be difficult to obtain a color filter in which the colored layer pattern is arranged according to a predetermined arrangement, while it is too much. Then, the formed colored layer may be easily detached from the substrate during development.

Among preferred photopolymerization initiators in the present invention, specific examples of acetophenone compounds include 2-hydroxy-2-methyl-1-phenylpropan-1-one and 2-methyl-1- [4- (methylthio) phenyl. ] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 1-hydroxycyclohexyl phenyl ketone, 2,2-dimethoxy- Examples include 1,2-diphenylethane-1-one and 1,2-octanedione.
Among these acetophenone compounds, in particular, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4-morpho Linophenyl) butan-1-one, 1,2-octanedione and the like are preferred.
The acetophenone compounds can be used alone or in admixture of two or more.

  In the present invention, the content when an acetophenone-based compound is used as the photopolymerization initiator is usually 0.01 to 80 parts by weight, preferably 1 with respect to 100 parts by weight of the (D) polyfunctional monomer. -70 weight part, More preferably, it is 1-60 weight part. In this case, if the content of the acetophenone-based compound is too small, curing by exposure becomes insufficient, and it may be difficult to obtain a color filter in which the colored layer pattern is arranged according to a predetermined arrangement. The formed colored layer may be easily removed from the substrate during development.

  Specific examples of the biimidazole compound include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-bi Imidazole, 2,2′-bis (2-bromophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2,2′-bis (2 -Chlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dichlorophenyl) -4,4', 5,5'-tetra Phenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2, 2'-bis (2-bromophenyl) -4,4 ', 5,5'-tetrafe 1,2′-biimidazole, 2,2′-bis (2,4-dibromophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2 ′ -Bis (2,4,6-tribromophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole and the like can be mentioned.

Among these biimidazole compounds, 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 and the like are preferable, and in particular, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2 '-Biimidazole is preferred.
These biimidazole compounds are excellent in solubility in solvents, do not generate foreign matters such as undissolved substances and precipitates, have high sensitivity, and sufficiently advance the curing reaction by exposure with a small amount of energy. Since no curing reaction occurs in the exposed area, the coated film after exposure is clearly divided into a cured area that is insoluble in the developer and an uncured area that has high solubility in the developer, Thereby, a high-definition color filter in which a colored layer pattern without an undercut is arranged according to a predetermined arrangement can be formed.
The biimidazole compounds can be used alone or in admixture of two or more.

  In the present invention, the content when a biimidazole compound is used as a photopolymerization initiator is usually 0.01 to 40 parts by weight, preferably 100 parts by weight of (D) polyfunctional monomer, 1 to 30 parts by weight, more preferably 1 to 20 parts by weight. In this case, if the content of the biimidazole compound is too small, curing due to exposure becomes insufficient, and it may be difficult to obtain a color filter in which the colored layer pattern is arranged according to a predetermined arrangement, while it is too much. When developing, there is a possibility that the formed colored layer may easily fall off from the substrate or the colored layer surface may come off.

In the present invention, when a biimidazole compound is used as a photopolymerization initiator, it is preferable to use a hydrogen donor described below in combination because the sensitivity can be further improved.
The “hydrogen donor” as used herein means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
As the hydrogen donor in the present invention, mercaptan compounds, amine compounds and the like defined below are preferable.

The mercaptan-based compound is a compound having a benzene ring or a heterocyclic ring as a mother nucleus and having one or more, preferably 1 to 3, more preferably 1 to 2, mercapto groups directly bonded to the mother nucleus (hereinafter referred to as “ Mercaptan-based hydrogen donor ").
The amine compound is a compound having a benzene ring or a heterocyclic ring as a mother nucleus and having 1 or more, preferably 1 to 3, more preferably 1 to 2 amino groups directly bonded to the mother nucleus (hereinafter referred to as “ Amine-based hydrogen donor ").
These hydrogen donors can also have a mercapto group and an amino group at the same time.

Hereinafter, the hydrogen donor will be described more specifically.
The mercaptan-based hydrogen donor can have one or more benzene rings or heterocyclic rings, and can have both a benzene ring and a heterocyclic ring. When two or more of these rings are present, It may or may not be formed.
In addition, when the mercaptan hydrogen donor has two or more mercapto groups, at least one of the remaining mercapto groups is substituted with an alkyl, aralkyl or aryl group as long as at least one free mercapto group remains. Furthermore, as long as at least one free mercapto group remains, a structural unit in which two sulfur atoms are bonded via a divalent organic group such as an alkylene group, or two sulfur atoms are It can have structural units linked in the form of disulfides.
Furthermore, the mercaptan-based hydrogen donor may be substituted with a carboxyl group, an alkoxycarbonyl group, a substituted alkoxycarbonyl group, a phenoxycarbonyl group, a substituted phenoxycarbonyl group, a nitrile group, or the like at a place other than the mercapto group.

Specific examples of such mercaptan hydrogen donors include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzoimidazole, 2,5-dimercapto-1,3,4-thiadiazole, 2-mercapto- 2,5-dimethylaminopyridine and the like can be mentioned.
Of these mercaptan-based hydrogen donors, 2-mercaptobenzothiazole and 2-mercaptobenzoxazole are preferable, and 2-mercaptobenzothiazole is particularly preferable.

In addition, the amine hydrogen donor can have one or more benzene rings or heterocyclic rings, and can have both a benzene ring and a heterocyclic ring. A ring may or may not be formed.
In addition, in the amine-based hydrogen donor, one or more of the amino groups may be substituted with an alkyl group or a substituted alkyl group, and a carboxyl group, an alkoxycarbonyl group, a substituted alkoxycarbonyl group, a phenoxy group may be substituted at a position other than the amino group. It may be substituted with a carbonyl group, a substituted phenoxycarbonyl group, a nitrile group or the like.

Specific examples of such amine-based hydrogen donors include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, Examples thereof include ethyl-4-dimethylaminobenzoate, 4-dimethylaminobenzoic acid, 4-dimethylaminobenzonitrile and the like.
Among these amine hydrogen donors, 4,4′-bis (dimethylamino) benzophenone and 4,4′-bis (diethylamino) benzophenone are preferable, and 4,4′-bis (diethylamino) benzophenone is particularly preferable.
The amine-based hydrogen donor has a function as a sensitizer even in the case of radical generators other than biimidazole compounds.

In the present invention, the hydrogen donor can be used alone or in admixture of two or more. However, one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. It is preferable that the formed colored layer does not easily fall off from the substrate during development, and the strength and sensitivity of the colored layer are high.
Specific examples of the combination of a mercaptan hydrogen donor and an amine hydrogen donor include 2-mercaptobenzothiazole / 4,4′-bis (dimethylamino) benzophenone, 2-mercaptobenzothiazole / 4,4′-bis. (Diethylamino) benzophenone, 2-mercaptobenzoxazole / 4,4′-bis (dimethylamino) benzophenone, 2-mercaptobenzoxazole / 4,4′-bis (diethylamino) benzophenone, and the like, and more preferred combinations 2-mercaptobenzothiazole / 4,4′-bis (diethylamino) benzophenone, 2-mercaptobenzoxazole / 4,4′-bis (diethylamino) benzophenone, and a particularly preferred combination is 2-mercaptobenzothiazole / , 4'-bis (diethylamino) benzophenone.
The weight ratio of mercaptan hydrogen donor to amine hydrogen donor in the combination of mercaptan hydrogen donor and amine hydrogen donor is usually 1: 1 to 1: 4, preferably 1: 1 to 1: 3.

  In the present invention, the content when the hydrogen donor is used in combination with the biimidazole compound is preferably 0.01 to 40 parts by weight, more preferably 100 parts by weight of the (D) polyfunctional monomer. 1 to 30 parts by weight, particularly preferably 1 to 20 parts by weight. In this case, if the content of the hydrogen donor is too small, the effect of improving the sensitivity tends to decrease. On the other hand, if the content is too large, the formed colored layer may be easily detached from the substrate during development.

  Specific examples of the triazine compound include 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 (trichloro Methyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxy) Phenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4- Triazine-based compounds having a halomethyl group such as xystyryl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-n-butoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine Can be mentioned.

Of these triazine compounds, 2- [2- (3,4-dimethoxyphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine is particularly preferable.
The triazine compounds can be used alone or in admixture of two or more.

  In the present invention, the content when using a triazine compound as a photopolymerization initiator is preferably 0.01 to 40 parts by weight, more preferably 100 parts by weight of (D) polyfunctional monomer. 1 to 30 parts by weight, particularly preferably 1 to 20 parts by weight. In this case, if the content of the triazine compound is too small, curing by exposure becomes insufficient, and it may be difficult to obtain a color filter in which the colored layer pattern is arranged according to a predetermined arrangement. The formed colored layer may be easily removed from the substrate during development.

Specific examples of the O-acyloxime compound include 1- [4- (phenylthio) phenyl] -heptane-1,2-dione 2- (O-benzoyloxime), 1- [4- (phenylthio). Phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [4- (benzoyl) phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [9 -Ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), 1- [9-ethyl-6- (3-methylbenzoyl) -9H-carbazole -3-yl] -ethanone 1- (O-acetyloxime), 1- (9-ethyl-6-benzoyl-9H-carbazol-3-yl) -ethanone 1- (O-acetyl) Oxime), ethanone-1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9 -Ethyl-6- (2-methyl-4-tetrahydropyranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2- Methyl-5-tetrahydrofuranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydropyranylbenzoyl) -9H-carbazol-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-) , 3-Dioxolanyl) benzoyl} -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-tetrahydropyranylmethoxybenzoyl) -9H-carbazol-3-yl ] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydrofuranylmethoxybenzoyl) -9H-carbazol-3-yl] -1- (O-acetyl) Oxime), ethanone-1- [9-ethyl-6- (2-methyl-5-tetrahydropyranylmethoxybenzoyl) -9H-carbazo -3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3-dioxolanyl) methoxybenzoyl } -9H-carbazol-3-yl] -1- (O-acetyloxime) and the like.

Of these O-acyloxime compounds, in particular, 1- [4- (phenylthio) phenyl] -octane-1,2-dione 2- (O-benzoyloxime), 1- [9-ethyl-6- ( 2-Methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime), ethanone-1- [9-ethyl-6- (2-methyl-4-tetrahydrofuranylmethoxybenzoyl) -9H -Carbazole-3-yl] -1- (O-acetyloxime), ethanone-1- [9-ethyl-6- {2-methyl-4- (2,2-dimethyl-1,3-dioxolanyl) methoxybenzoyl } -9H-carbazol-3-yl] -1- (O-acetyloxime) and the like are preferable.
The O-acyloxime compounds can be used alone or in admixture of two or more.

  In the present invention, when the O-acyloxime compound is used as a photopolymerization initiator, the amount used is preferably 0.01 to 80 parts by weight with respect to 100 parts by weight of the (D) polyfunctional monomer, More preferably, it is 1-70 weight part, Most preferably, it is 1-60 weight part. In this case, if the content of the O-acyloxime compound is too small, curing by exposure may be insufficient, and it may be difficult to obtain a color filter in which a colored layer pattern is arranged according to a predetermined arrangement. If the amount is too large, the formed colored layer may be easily removed from the substrate during development.

-Other additives-
The radiation-sensitive resin composition for forming a colored layer of the present invention contains the components (A) to (E) as essential components, but may further contain other additives as necessary. .
Examples of the other additives include fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); nonionic surfactants, cationic surfactants, anionic interfaces Surfactants such as activators; vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-amino Ethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl Trimethoxysilane, 3-chloropropylmethyldi Adhesion promoters such as toxisilane, 3-chloropropyltrimethoxysilane, 3-methacryloyloxypropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane; 2,2-thiobis (4-methyl-6-tert-butylphenol), Antioxidants such as 2,6-di-t-butylphenol; UV absorbers such as 2- (3-t-butyl-5-methyl-2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenones; poly Anticoagulation agents such as sodium acrylate; residue improvers such as malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, and mesaconic acid.

Preparation of Liquid Composition The radiation-sensitive resin composition for forming a colored layer of the present invention is usually prepared as a liquid composition by blending a solvent.
As said solvent, (A)-(E) component which comprises a radiation sensitive resin composition, and another additive component are disperse | distributed or melt | dissolved, and it does not react with these components, but has moderate volatility As long as it is, it can be appropriately selected and used.

As such a solvent, for example,
Propylene glycol monoalkyl ethers such as propylene glycol monomethyl ether and propylene glycol monoethyl ether;
Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol mono-n-butyl ether acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether acetate, propylene (Poly) alkylene glycol monoalkyl ether acetates such as glycol monoethyl ether acetate, dipropylene glycol monomethyl ether acetate, dipropylene glycol monoethyl ether acetate, 3-methoxybutyl acetate; diethylene glycol dimethyl ether, diethylene glycol methyl Ethyl ether, diethylene glycol diethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol methyl ethyl ether, dipropylene glycol diethyl ether of (poly) alkylene glycol diethers;
Other ethers such as tetrahydrofuran;
Ketones such as methyl ethyl ketone, cyclohexanone, 2-heptanone, 3-heptanone;
Ketoalcohols such as diacetone alcohol (ie 4-hydroxy-4-methylpentan-2-one), 4-hydroxy-4-methylhexan-2-one;

Lactic acid alkyl esters such as methyl lactate and ethyl lactate;
Ethyl 2-hydroxy-2-methylpropionate, ethyl hydroxyacetate, methyl 2-hydroxy-3-methylbutanoate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxypropion Ethyl acetate, ethyl ethoxy acetate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-acetate Butyl, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate , Methyl acetoacetate, ethyl acetoacetate, 2-oxobutanoic acid Other esters such as Le;
Aromatic hydrocarbons such as toluene and xylene;
Examples thereof include amides such as N-methylpyrrolidone, N, N-dimethylformamide, and N, N-dimethylacetamide.

Among these solvents, from the viewpoint of solubility, pigment dispersibility, coatability, etc., propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol mono-n-propyl ether acetate, ethylene glycol mono -N-butyl 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 acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, dipropylene glycol dimethyl ether Cyclohexanone, 2-heptanone, 3-heptanone, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutylpropionate, Preferred are n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyl butyrate, ethyl pyruvate and the like.
The said solvent can be used individually or in mixture of 2 or more types.

Further, together with the solvent, benzyl ethyl ether, di-n-hexyl ether, acetonyl acetone, isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate In addition, a high boiling point solvent such as diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol monophenyl ether acetate can be used in combination.
The high boiling point solvents can be used alone or in admixture of two or more.

  The amount of the solvent used is not particularly limited, but the total concentration of each component excluding the solvent of the composition is preferably 5 to 5 from the viewpoints of applicability, stability and the like of the obtained liquid composition. An amount of 50% by weight, particularly preferably 10 to 40% by weight, is desirable.

Method of forming a color filter Then, using a colored layer forming radiation sensitive resin composition of the present invention, a method for forming a color filter of the present invention.
The method for forming a color filter usually includes at least the following steps (1) to (4).
(1) The process of forming the coating film of the radiation sensitive resin composition for colored layer formation of this invention on a board | substrate.
(2) A step of exposing at least a part of the coating film.
(3) A step of developing the coated film after exposure.
(4) A step of heat-treating (hereinafter referred to as “post-bake”) the coated film after development.
Hereinafter, these steps will be sequentially described.

-(1) Process-
First, on the surface of the substrate, if necessary, a light shielding layer is formed so as to partition a portion where pixels are formed, and a radiation sensitive resin for forming a colored layer containing, for example, a red pigment is formed on the substrate. After applying the liquid composition, the composition is pre-baked to evaporate the solvent and form a coating film.
Examples of the substrate used in this step include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, polyimide, polyethersulfone, cyclic olefin ring-opening polymer, and hydrogenated products thereof. be able to.
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, gas phase reaction method, vacuum deposition, etc., if desired.
When the liquid composition is applied to the substrate, an appropriate application method such as spin coating, cast coating, roll coating, or slit nozzle coating can be employed. The resin composition has high solubility in a cleaning solvent even after drying, and is suitable for application by a slit nozzle.
The prebaking condition is usually about 2 to 4 minutes at 70 to 110 ° C.
The coating thickness is usually 0.1 to 10 μm, preferably 0.2 to 8.0 μm, and more preferably 0.2 to 6.0 μm as the film thickness after removal of the solvent.

-(2) Process-
Thereafter, at least a part of the formed coating film is exposed. When exposing a part of the coating film, it is usually exposed through a photomask having an appropriate pattern.
As the radiation used in this step, for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used, but radiation having a wavelength in the range of 190 to 450 nm is preferable.
Exposure of radiation is usually, 10~10,000J / m ² approximately.

-(3) Process-
Thereafter, the exposed coating film is preferably developed using an alkali developer, and an unexposed portion of the coating film is dissolved and removed to form a pattern.
Examples of the alkali developer include sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1,5- An aqueous solution of diazabicyclo- [4.3.0] -5-nonene is preferred.
An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline developer. In addition, it is usually washed with water after alkali development.
As the development processing method, a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid buildup) development method, and the like can be applied, but the radiation-sensitive resin composition in the present invention is an alkali development. It has high solubility in liquids and is suitable for development by shower development.
The development conditions are preferably about 5 to 300 seconds at room temperature.

-(4) Process-
Then, the post-baked coating film after development can provide a substrate on which pixel patterns made of a cured product of the radiation-sensitive resin composition are arranged in a predetermined arrangement.
The post-baking conditions are preferably 180 to 230 ° C. and about 20 to 40 minutes.
The film thickness of the pixel thus formed is usually 0.5 to 5.0 μm, preferably 1.5 to 3.0 μm.

  Further, by repeating the steps (1) to (4) using each liquid composition of the colored layer forming radiation-sensitive resin composition containing a green or blue pigment, a green pixel pattern and a blue color are obtained. By forming the pixel pattern on the same substrate, a colored layer in which the pixel patterns of the three primary colors of red, green, and blue are arranged in a predetermined arrangement can be formed on the substrate. However, the order of forming the pixel patterns of the respective colors in the present invention is not limited to the order described above.

Color filter The color filter of the present invention comprises a colored layer formed using the radiation-sensitive resin composition for forming a colored layer of the present invention.
The color filter of the present invention is extremely useful for, for example, a transmissive or reflective color liquid crystal display device, a color imaging tube element, a color sensor, and the like.

Color liquid crystal display device The color liquid crystal display device of the present invention comprises the color filter of the present invention.
The color liquid crystal display device of the present invention can have an appropriate structure. For example, the color filter is formed on a substrate different from the driving substrate on which the thin film transistor (TFT) is arranged, and the driving substrate and the substrate on which the color filter is formed are opposed to each other through the liquid crystal layer. Furthermore, a substrate in which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate in which an ITO (indium oxide doped with tin) electrode is formed include a liquid crystal layer. It is also possible to adopt a structure facing each other. The latter structure has the advantage that the aperture ratio can be remarkably improved and a bright and high-definition color liquid crystal display device can be obtained.

Hereinafter, the embodiment of the present invention will be described more specifically with reference to examples. However, the present invention is not limited to the following examples.
Mw and Mn of the resin obtained in each of the following synthesis examples were measured by gel permeation chromatography (GPC) according to the following specifications.
Apparatus: GPC-101 (manufactured by Showa Denko KK).
Column: GPC-KF-801, GPC-KF-802, GPC-KF-803 and GPC-KF-804 were used in combination.
Mobile phase: Tetrahydrofuran containing 0.5% by weight of phosphoric acid.

Synthesis of alkali-soluble resin Synthesis Example 1
A flask equipped with a condenser and a stirrer was charged with 3 parts by weight of 2,2′-azobisisobutyronitrile and 200 parts by weight of propylene glycol monomethyl ether acetate, followed by 15 parts by weight of methacrylic acid and ω-carboxypolycacrolactone. 5 parts by weight of monoacrylate, 22 parts by weight of N-phenylmaleimide, 13 parts by weight of styrene, 35 parts by weight of benzyl methacrylate, 10 parts by weight of glycerol mono (meth) acrylate, and 5 parts by weight of α-methylstyrene dimer as a molecular weight regulator And replaced with nitrogen. Thereafter, the reaction solution was gently stirred and heated to 80 ° C., and this temperature was maintained and polymerization was carried out for 5 hours to obtain a copolymer (S-1) solution. (Mw = 10,500, Mn = 5,200, solid content concentration 31.2 wt%)

Developer immersion test Example 1
(A) C.I. I. Pigment Green 36 and C.I. I. 40 parts by weight of a 50/50 (weight ratio) mixture with CI Pigment Yellow 150, 10 parts by weight (in terms of solid content) of Disperbyk 2001 (nonvolatile component = 46%, amine number = 29) as a dispersant, and propylene glycol monomethyl ether as a solvent A mixed liquid consisting of 100 parts by weight of acetate was mixed and dispersed for 12 hours with a diamond fine mill (trade name, manufactured by Mitsubishi Materials Corporation, bead mill (bead diameter: 1.0 mm)) to obtain a pigment dispersion (p-1). Prepared.
Next, 450 parts by weight of this pigment dispersion (p-1), (B) 90 parts by weight (in terms of solid content) of copolymer (S-1) as an alkali-soluble resin, and (C) as a polyfunctional monomer 60 parts by weight of TO-1382, (D) 15 parts by weight of 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one as a photopolymerization initiator and 1- [9-ethyl- 6- (2-Methylbenzoyl) -9H-carbazol-3-yl] -ethanone 1- (O-acetyloxime) 5 parts by weight and 800 parts by weight of ethyl 3-ethoxypropionate as a solvent were mixed to form a liquid composition A product (r-1) was prepared. In the liquid composition (r-1), the pigment content is 37.5% in the total solid content.
Next, the liquid composition (r-1) was spin-coated on a soda glass substrate having a diameter of 4 inches on which a SiO ₂ film for preventing elution of sodium ions was formed on the surface, and then in a clean oven at 80 ° C. Pre-baking was performed for 10 minutes to form a 3.0 μm coating film on the substrate.
The substrate was then immersed for 2 minutes in 1000 cc of a developer composed of a 0.04 wt% aqueous potassium hydroxide solution stirred with a magnetic stirrer, whereby the coating film was completely dissolved.

Example 2
A liquid composition (r-2) was prepared in the same manner as in Example 1 except that Disperbyk142 (nonvolatile component = 60%, amine value = 43) was used instead of Disperbyk2001 as a dispersant, and a soda glass substrate was prepared. A coating was formed on top.
Then, when this substrate was immersed in 1000 cc of a developer comprising a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was completely dissolved.

Example 3
A soda glass substrate was prepared by preparing a liquid composition (r-3) in the same manner as in Example 1 except that Dispersbyk 145 (nonvolatile component = 100%, amine value = 71) was used instead of Dispersbyk 2001 as a dispersant. A coating was formed on top.
Then, when this substrate was immersed in 1000 cc of a developer comprising a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was completely dissolved.

Example 4
A soda glass substrate was prepared by preparing a liquid composition (r-4) in the same manner as in Example 1, except that Dispersbyk 2150 (nonvolatile component = 52%, amine value = 57) was used instead of Dispersbyk 2001 as a dispersant. A coating was formed on top.
Then, when this substrate was immersed in 1000 cc of a developer comprising a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was completely dissolved.

Comparative Example 1
(C) Except for using TO-756 (manufactured by Toagosei Co., Ltd.) whose main component is a monoesterified product of pentaerythritol triacrylate and succinic acid instead of TO-1382 as a polyfunctional monomer. In the same manner as in Example 1, a liquid composition (r-5) was prepared, and a coating film was formed on a soda glass substrate.
Then, when this substrate was immersed in 1000 cc of a developer comprising a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was completely dissolved.

Comparative Example 2
(C) A liquid composition (r-6) was prepared in the same manner as in Example 1 except that dipentaerythritol hexaacrylate was used in place of TO-1382 as the polyfunctional monomer, and soda glass was prepared. A coating film was formed on the substrate.
Then, when this substrate was immersed in 1000 cc of a developer consisting of a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was not completely dissolved, and a large amount of insoluble matter was contained in the solution. Lump was observed.

Comparative Example 3
(C) A liquid composition (r-7) was prepared in the same manner as in Example 2 except that dipentaerythritol hexaacrylate was used in place of TO-1382 as the polyfunctional monomer, and soda glass was prepared. A coating film was formed on the substrate.
Then, when this substrate was immersed in 1000 cc of a developer consisting of a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was not completely dissolved, and a large amount of insoluble matter was contained in the solution. Lump was observed.

Reference example 1
The same procedure as in Comparative Example 1, except that the amount of the pigment dispersion (p-1) was changed from 450 parts by weight to 225 parts by weight and the amount of the solvent ethyl 3-ethoxypropionate was changed from 800 parts by weight to 600 parts by weight. Then, a liquid composition (r-8) was prepared, and a coating film was formed on the soda glass substrate.
In the liquid composition (r-8), the pigment content is 24.5% in the total solid content.
Then, when this substrate was immersed in 1000 cc of a developer comprising a 0.04 wt% aqueous potassium hydroxide solution for 2 minutes in the same manner as in Example 1, the coating film was completely dissolved.

Evaluation of developability Example 5
The liquid composition (r-1) was applied to a soda glass substrate having a diameter of 4 inches on the surface of which a SiO ₂ film for preventing elution of sodium ions was formed using a spin coater, and then applied to a hot plate at 90 ° C. Was pre-baked for 2 minutes to form a coating film having a thickness of 2.5 μm.
Next, after cooling the substrate to room temperature, the coating film was exposed to ultraviolet rays including 365 nm, 405 nm, and 436 nm through a photomask (slit width 90 μm) using a high pressure mercury lamp. The exposure amount at this time was 1000 J / m ² . Thereafter, a 0.04 wt% potassium hydroxide aqueous solution at 23 ° C. was discharged for 1 minute at a developing pressure of 1 kgf / cm ² (nozzle diameter 1 mm) to perform a shower development, and then at 220 ° C. for 30 minutes. By performing post-baking, a red stripe pixel pattern was formed on the substrate.
When the pixel array on the substrate was observed with an optical microscope, no development residue was observed on the unexposed portion of the substrate, and no chipping was observed on the edge of the pixel pattern.

Example 6
Except for using the liquid composition (r-2) instead of the liquid composition (r-1), the evaluation of developability was carried out in the same manner as in Example 5, and on the unexposed portion of the substrate. No development residue was observed, and no chipping was observed on the edge of the pixel pattern.

Example 7
Except for using the liquid composition (r-3) instead of the liquid composition (r-1), the evaluation of developability was carried out in the same manner as in Example 5, and on the unexposed portion of the substrate. No development residue was observed, and no chipping was observed on the edge of the pixel pattern.

Example 8
Except that the liquid composition (r-4) was used in place of the liquid composition (r-1), the developability was evaluated in the same manner as in Example 5, and on the unexposed portion of the substrate. No development residue was observed, and no chipping was observed on the edge of the pixel pattern.

Comparative Example 4
Except that the liquid composition (r-5) was used in place of the liquid composition (r-1), the developability was evaluated in the same manner as in Example 5, and on the unexposed substrate. No development residue was observed, and no chipping was observed on the edge of the pixel pattern.

Comparative Example 5
Except for using the liquid composition (r-6) in place of the liquid composition (r-1), the developability was evaluated in the same manner as in Example 5, and the edge of the pixel pattern was not chipped. Although not recognized, a slight development residue was observed on the unexposed substrate.

Comparative Example 6
Except for using the liquid composition (r-7) in place of the liquid composition (r-1), the developability was evaluated in the same manner as in Example 5. The pixel pattern could not be formed because it was not completely dissolved.

Reference example 2
Except for using the liquid composition (r-8) instead of the liquid composition (r-1), the evaluation of developability was carried out in the same manner as in Example 5 to find on the unexposed portion of the substrate. No development residue was observed, and no chipping was observed on the edge of the pixel pattern.

Evaluation of surface smoothness The surface roughness of the upper part of each pixel pattern obtained in the evaluation of adhesion was measured and evaluated using an atomic force microscope manufactured by Digital Instruments. Generally, when the surface roughness is 60 mm or less, it can be said that the surface smoothness is good.

Example 9
When the surface smoothness of the pattern prepared in Example 5 was measured, the surface roughness was 50 mm.

Example 10
When the surface smoothness of the pattern prepared in Example 6 was measured, the surface roughness was 40 mm.

Example 11
When the surface smoothness of the pattern prepared in Example 7 was measured, the surface roughness was 37 mm.

Example 12
When the surface smoothness of the pattern prepared in Example 8 was measured, the surface roughness was 44 mm.

Comparative Example 7
When the surface smoothness of the pattern prepared in Comparative Example 4 was measured, the surface roughness was 80 mm.

Comparative Example 8
When the surface smoothness of the pattern prepared in Comparative Example 5 was measured, the surface roughness was 40 mm.

Comparative Example 9
When the surface smoothness of the pattern prepared in Comparative Example 6 was measured, the surface roughness was 35 mm.

Reference example 3
When the surface smoothness of the pattern prepared in Reference Example 2 was measured, the surface roughness was 50 mm.

Claims (3)

(A) a pigment containing at least one selected from the group consisting of a red pigment, a green pigment and a blue pigment, (B) a dispersant having an amine value (unit mgKOH / g) of 57 / 0.52 to 200, A radiation-sensitive resin composition for forming a colored layer, comprising: C) an alkali-soluble resin, (D) a polyfunctional monomer represented by the following formula (1), and (E) a photopolymerization initiator, A) A radiation-sensitive resin composition for forming a colored layer, wherein the pigment content is 30 to 60% by weight in the total solid content.

(Wherein R ₁ represents a hydrogen atom or a methyl group, R ₂ has a methylene group, a linear or branched alkylene group having 2 to 8 carbon atoms, a linear or branched alkenylene group, and a substituent. A group selected from the group consisting of a phenylene group that may be substituted, a cyclohexylene group that may have a substituent, and a group in which part of the cyclohexylene group that may have a substituent is an unsaturated bond; Show.)   A color filter formed from the radiation-sensitive composition according to claim 1.   A color liquid crystal display device comprising the color filter according to claim 2.