JPH11100529A - Radiation-sensitive composition used for color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compsn. for an additive color mixing type application used for a reflection type color liq. crystal display by blending a colorant comprising a quinacridone type pigment, an alkali soluble resin, a multifunctional monomer and a photopolymerization initiator. SOLUTION: A colorant comprising a quinacridone type pigment having the formula (R<1> -R<8> are, each, H, methyl or chlorine) is employed. A mixture of a quinacridone type pigment and an orange pigment is esp. pref. The orange pigment is usually used at a concn. of <=40 wt.%. The alkali-soluble resin is usually used in an amt. of 10-1,000 pts.wt. based on 100 pts.wt. of the colorant. The multifunctional monomer is usually used in an amt. of 5-500 pts.wt. based on 100 pts.wt. of the alkali-soluble resin. The photopolymerization initiator is usually used in an amt. of 0.01-200 pts.wt. based on 100 pts.wt. of the whole monomer. This compsn. has excellent thermal resistance and weatherability as well as an optimized spectral transmittance suited for the peripheral light spectrum.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a radiation-sensitive composition for a color filter used for producing an additive color mixture type color filter used for a reflection type color liquid crystal display device.

[0002]

2. Description of the Related Art A color filter used in a color liquid crystal display device has two or more kinds of pixels having different color tones arranged on a transparent substrate such as a glass substrate in parallel or crosswise in a striped pixel. The rectangular pixels are arranged vertically and horizontally, and the pixel size is as fine as several tens μm to several hundred μm. Conventionally, when manufacturing a color filter in which such fine pixels are regularly arranged, a photosensitive resin is applied on a substrate, and the formed coating film is irradiated with radiation through a photomask to irradiate the radiation with a radiation irradiation unit. Is cured and then developed to remove the unirradiated portion of the coating film and pattern it. After that, a dyeing method of dyeing or a composition in which a coloring agent (dye or pigment) is dissolved or dispersed in a photosensitive resin is used. A method such as a photolithography method in which an object is used to form a pattern by performing coating film formation, radiation irradiation, and development processing in the same manner as described above, is employed. In addition, the color liquid crystal display device includes:
Generally, in order to drive the liquid crystal, a transparent electrode made of indium oxide, tin oxide, or the like is formed on the color filter by, for example, vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon. In order to obtain a high-performance transparent electrode and an alignment film, a high temperature of generally 200 ° C. or higher, preferably 250 ° C. or higher is required at the time of forming them. Among the color filters manufactured by the above method, a color filter using a dye has high transparency to radiation, but has insufficient heat resistance. Therefore, formation of a transparent electrode and an alignment film is performed at a temperature of less than 200 ° C. Inevitably, the performance of the transparent electrode and the alignment film cannot be sufficiently ensured. In addition, color filters using dyes also have poor light resistance, and are not suitable for outdoor use. Therefore, instead of dyes, pigments having excellent heat resistance and light resistance have come to be used, and most of currently manufactured color filters use organic pigments. By the way, a color liquid crystal display device is roughly divided into a light source (backlight) provided on the back surface of the device, and a transmission type color liquid crystal display device for displaying by the transmitted light and a light reflection plate such as an aluminum foil provided on the back surface of the device. There is a reflective color liquid crystal display device that is attached to the back of the transparent substrate and reflects and reflects the incident light from the front of the device.The reflective color liquid crystal display device has the advantage of low power consumption without requiring a separate light source. Has become widely adopted. Today, as a color filter used in a color liquid crystal display device, an additive color mixture type of three primary colors of red (R), green (G) and blue (B) is generally used. A reflective color liquid crystal display device using a subtractive color filter of three colors of C), magenta (M) and yellow (Y) has also been announced (see “Electronic Display Forum 97”). However, the additive color mixture type color filter used in the transmission type color liquid crystal display device is optimized for the spectrum of the three wavelength tube of the backlight which is the light source, and is not necessarily suitable for the reflection type color liquid crystal display device. I couldn't say. In addition, by using a pigment composed of a specific azo metal salt or a mixture of the pigment and a yellow pigment as a colorant of a coloring composition for a color filter used in a reflective color liquid crystal display device, heat resistance and light resistance are improved. Japanese Patent Application Laid-Open No. 9-6 / 1994 discloses that a color filter which is excellent and has a color purity equal to or higher than the color filter obtained by the dyeing method can be formed.
No. 8608 discloses this. However, in this coloring composition, the relationship between the spectral transmittance of the coloring agent used and the spectrum of ambient light (for example, sunlight, light of a fluorescent lamp, etc.) is not taken into consideration, and the reflection type color liquid crystal display device is not considered. Are still unsatisfactory as a coloring composition used for the formation of the color filter. Therefore, there is a strong demand for the development of a color filter of an additive color mixture type used in a reflective color liquid crystal display device, in which, in addition to heat resistance and light resistance, its spectral transmittance is optimized in accordance with the spectrum of ambient light. I was

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide an additive color liquid crystal display device which is excellent in heat resistance and light resistance and has a spectral transmittance optimized in accordance with the spectrum of ambient light. An object of the present invention is to provide a radiation-sensitive composition used for producing a color mixture type color filter.

[0004]

The present invention firstly provides:
In the radiation-sensitive composition for a color filter containing (A) a coloring agent, (B) an alkali-soluble resin, (C) a polyfunctional monomer, and (D) a photopolymerization initiator, the following (A) coloring agent is used. A radiation-sensitive composition for an additive color mixture type color filter for use in a reflective color liquid crystal display device, comprising a quinacridone pigment represented by the structural formula (1),

[0005]

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[In the structural formula (1), R ^{1 to} R ⁸ each independently represent a hydrogen atom, a methyl group or a chlorine atom. ].

The present invention relates to (A) a colorant, (B)
In the radiation-sensitive composition for a color filter containing an alkali-soluble resin, (C) a polyfunctional monomer and (D) a photopolymerization initiator, the colorant (A) is represented by the following structural formula (1)
Radiation-sensitive composition for an additive color mixture type color filter used in a reflective color liquid crystal display device, comprising a mixture of a quinacridone pigment and an orange pigment represented by

[0008]

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[In the structural formula (1), R ^{1 to} R ⁸ each independently represent a hydrogen atom, a methyl group or a chlorine atom. ]. The term “radiation” as used in the present invention includes visible light, ultraviolet light, far ultraviolet light, X-rays, electron beams and the like.

Hereinafter, the present invention will be described in detail. (A) Colorant The colorant in the present invention contains the quinacridone pigment represented by the structural formula (1) (hereinafter, referred to as “quinacridone pigment (1)”). Specific examples of the quinacridone pigment (1) are described in Color Index (C.
I .; published by The Society of Dyers and Colorists) When indicated by numbers and component names (in parentheses), CI Pigment Violet 19 (quinacridone), CI Pigment Red 122 (2,9-dimethylquinacridone), CI Pigment Red 202 ( 2,9-dichloroquinacridone), CI Pigment Red 206 (solid solution of quinacridone and 6,13-dioxoquinacridone), CI Pigment Red 207 (solid solution of quinacridone and 4,11-dichloroquinacridone), CI Pigment Red 209 ( 3,10-dichloroquinacridone), among which CI Pigment Violet 19 is preferred. Quinacridone includes α-form, β-form (purple) and γ-form (red) crystal forms, and a particularly preferred quinacridone-based pigment (1) in the present invention is γ-form quinacridone.

In the present invention, other pigments can be used together with the quinacridone pigment (1) as a colorant component within a range not to impair the intended effect of the present invention.
The other pigment can be appropriately selected according to the use of the color filter and the desired hue of the pixel, but an orange pigment is preferable because the hue of the pixel can be easily adjusted.
Specific examples of the orange pigment include CI Pigment Orange 36 and CI Color Index (CI) number.
Pigment Orange 64, CI Pigment Orange 71
Among them, CI Pigment Orange 71 is particularly preferable. As the colorant in the present invention, a mixture of a quinacridone pigment (1) and an orange pigment is particularly preferable. In this case, the proportion of the orange pigment used is usually 40% by weight or less, preferably 3% by weight of all the pigments.
It is at most 5% by weight, more preferably 5 to 30% by weight.

In the present invention, the surface of each of the pigments may be modified with a polymer before use. Examples of the polymer for modifying the pigment surface include, for example, JP-A-8-2598.
Examples of the polymer include a polymer described in JP-A-76-176 and various commercially available polymers or oligomers for dispersing a pigment. Further, each pigment in the present invention, if desired,
It can be used with dispersants. Examples of such a dispersant include cationic, anionic, nonionic, amphoteric, silicone-based, and fluorine-based surfactants. As a specific example of the surfactant,
Polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, and polyoxyethylene oleyl ether;
Polyoxyethylene alkyl phenyl ethers such as polyoxyethylene octyl phenyl ether and polyoxyethylene nonyl phenyl ether; polyethylene glycol diesters such as polyethylene glycol dilaurate and polyethylene glycol distearate; sorbitan fatty acid esters; fatty acid-modified polyesters;
Tertiary amine-modified polyurethanes; polyethyleneimines, etc., and KP (Shin-Etsu Chemical Co., Ltd.)
), Polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), F-Top (manufactured by Tochem Products), Megafac (manufactured by Dainippon Ink & Chemicals, Inc.), Florard (manufactured by Sumitomo 3M Limited), Asahi Guard, Surflon (all manufactured by Asahi Glass Co., Ltd.) and the like. These surfactants can be used alone or in combination of two or more. The amount of the surfactant to be used is generally 50 parts by weight or less, preferably 0 to 30 parts by weight, based on 100 parts by weight of the total pigment.

(B) Alkali-Soluble Resin Next, as the alkali-soluble resin in the present invention,
(A) When it acts as a binder for a colorant and is soluble in a developing solution used in the developing step, particularly preferably an alkali developing solution, in producing a color filter, Although not limited, a polymer containing a carboxyl group, in particular, an ethylenically unsaturated monomer having one or more carboxyl groups (hereinafter, simply referred to as “carboxyl group-containing unsaturated monomer”). Other copolymerizable ethylenically unsaturated monomers (hereinafter simply referred to as “copolymerizable unsaturated monomers”)
(Hereinafter, simply referred to as “carboxyl group-containing copolymer”). As the carboxyl group-containing unsaturated monomer, for example, acrylic acid, methacrylic acid,
Unsaturated monocarboxylic acids such as crotonic acid, α-chloroacrylic acid, and cinnamic acid; maleic acid, maleic anhydride, fumaric acid, itaconic acid, itaconic anhydride, citraconic acid,
Unsaturated dicarboxylic acids such as citraconic anhydride and mesaconic acid or anhydrides thereof; trivalent or higher unsaturated polycarboxylic acids or anhydrides thereof; monosuccinic acid (2-acryloyloxyethyl), monosuccinic acid ( 2-methacryloyloxyethyl), mono (2-acryloyloxyethyl) phthalate, mono (2-methacryloyloxyethyl) phthalate
Mono [(meth) acryloyloxyalkyl] esters of divalent or higher polyvalent carboxylic acids such as ω-carboxypolycaprolactone monoacrylate, ω-carboxypolycaprolactone monomethacrylate, etc. And acrylates. These carboxyl group-containing unsaturated monomers can be used alone or in combination of two or more.

Examples of the copolymerizable unsaturated monomer include, for example, styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene and p-vinyltoluene.
Chlorostyrene, o-methoxystyrene, m-methoxystyrene, p-methoxystyrene, o-vinylbenzyl methyl ether, m-vinylbenzyl methyl ether,
aromatic vinyl compounds such as p-vinylbenzyl methyl ether, o-vinylbenzyl glycidyl ether, m-vinylbenzyl glycidyl ether, p-vinylbenzyl glycidyl ether, indene; methyl acrylate,
Methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, n-propyl methacrylate, i-propyl acrylate, i-propyl methacrylate, n-butyl acrylate, n-
Butyl methacrylate, i-butyl acrylate, i-
Butyl methacrylate, sec-butyl acrylate,
sec-butyl methacrylate, t-butyl acrylate, t-butyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate,
2-hydroxypropyl acrylate, 2-hydroxypropyl methacrylate, 3-hydroxypropyl acrylate, 3-hydroxypropyl methacrylate, 2
-Hydroxybutyl acrylate, 2-hydroxybutyl methacrylate, 3-hydroxybutyl acrylate, 3-hydroxybutyl methacrylate, 4-hydroxybutyl acrylate, 4-hydroxybutyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate,
Cyclohexyl acrylate, cyclohexyl methacrylate, phenyl acrylate, phenyl methacrylate, 2-methoxyethyl acrylate, 2-methoxyethyl methacrylate, 2-phenoxyethyl acrylate, 2-phenoxyethyl methacrylate, methoxydiethylene glycol acrylate, methoxydiethylene glycol methacrylate, methoxy triacrylate Ethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate, isobornyl methacrylate, dicyclo Pentadieni Unsaturated carboxylic esters such as acrylate, dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, -Dimethylaminoethyl acrylate, 2-dimethylaminoethyl methacrylate, 2
-Aminopropyl acrylate, 2-aminopropyl methacrylate, 2-dimethylaminopropyl acrylate, 2-dimethylaminopropyl methacrylate, 3-
Unsaturated carboxylic acid aminoalkyl esters such as aminopropyl acrylate, 3-aminopropyl methacrylate, 3-dimethylaminopropyl acrylate, and 3-dimethylaminopropyl methacrylate; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; acetic acid Carboxylic acid vinyl esters such as vinyl, vinyl propionate, vinyl butyrate and vinyl benzoate; unsaturated ethers such as vinyl methyl ether, vinyl ethyl ether and allyl glycidyl ether; acrylonitrile, methacrylonitrile, α
Vinyl cyanide compounds such as chloroacrylonitrile and vinylidene cyanide; unsaturated amides such as acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide and N-2-hydroxyethylmethacrylamide; maleimide, N Unsaturated imides such as -phenylmaleimide and N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene and chloroprene; polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate and poly And macromonomers having a monoacryloyl group or a monomethacryloyl group at a terminal of a polymer molecular chain such as -n-butyl methacrylate and polysiloxane. These copolymerizable unsaturated monomers can be used alone or in combination of two or more.

As the carboxyl group-containing copolymer in the present invention, acrylic acid and / or methacrylic acid are essential, and in some cases, mono (2-acryloyloxyethyl) succinate and / or mono (2-methacrylic acid) are used. Carboxyl group-containing unsaturated monomer component further containing (loiroxyethyl), styrene, methyl acrylate, methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate , A copolymer with at least one selected from the group consisting of N-phenylmaleimide, polystyrene macromonomer and polymethyl methacrylate macromonomer (hereinafter referred to as “carboxyl group-containing copolymer (I)”) Say.) It is preferred.

Specific examples of the carboxyl group-containing copolymer (I) include (meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / benzyl (meth) acrylate copolymer, and (meth) acrylic acid. ) 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) acryl Acid / 2-hydroxyethyl (meth) acrylate / benzyl (meth) acrylate / polymethyl methacrylate macromonomer copolymer, methacrylic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / succinic acid mono (2 -Acryloyloxyethyl) / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / mono (2-acryloyloxyethyl succinate) / styrene / allyl methacrylate / N-phenylmer It can be mentioned imide copolymers.

The copolymerization ratio of the carboxyl group-containing unsaturated monomer in the carboxyl group-containing copolymer is usually 5
５０50% by weight, preferably 10-40% by weight. In this case, if the copolymerization ratio is less than 5% by weight, the solubility of the obtained radiation-sensitive composition in an alkali developer tends to decrease, while if it exceeds 50% by weight, the solubility in an alkali developer becomes poor. When developed with an alkali developing solution, the pixel tends to easily fall off from the substrate or become rough on the pixel surface. Gel permeation chromatography of the alkali-soluble resin in the present invention (GPC, elution solvent: tetrahydrofuran)
Weight average molecular weight in terms of polystyrene (hereinafter, referred to as
It is called "Mw". ) Is usually 3,000 to 300,0
00, preferably 5,000 to 100,000.
By using such an alkali-soluble resin having a specific Mw, a radiation-sensitive composition excellent in developability can be obtained, whereby a pixel having a sharp pattern edge can be formed, and Occasionally background dirt in areas other than the areas where pixels are formed on the substrate,
Film residue and the like hardly occur. In the present invention, the alkali-soluble resins can be used alone or in combination of two or more. The amount of the alkali-soluble resin used in the present invention is usually based on 100 parts by weight of the colorant (A).
It is 10 to 1000 parts by weight, preferably 20 to 500 parts by weight. In this case, the amount of the alkali-soluble resin used is 10
If the amount is less than 10 parts by weight, for example, the alkali developability may be reduced, or background contamination or film residue may occur in a region other than the portion where the pixels are formed on the substrate. Since the pigment concentration decreases, it may be difficult to achieve the color concentration required for the color filter.

(C) Polyfunctional Monomer The polyfunctional monomer in the present invention is a monomer having two or more polymerizable unsaturated bonds, and examples thereof include ethylene glycol and propylene glycol. Diacrylates or dimethacrylates of alkylene glycols such as polyethylene glycol, polypropylene glycol and the like; diacrylates or dimethacrylates of polyalkylene glycols such as glycerin, trimethylolpropane, pentaerythritol and dipentaerythritol; Polyacrylates or polymethacrylates of alcohols and their dicarboxylic acid modified products; oligoacrylates or oligomethacrylates such as polyester, epoxy resin, urethane resin, alkyd resin, silicone resin, and spirane resin Diacrylates or dimethacrylates of hydroxyl-terminated polymers such as hydroxypoly-1,3-butadiene at both ends, hydroxypolyisoprene at both ends, hydroxypolycaprolactone at both ends, and tris (2-acryloyloxyethyl) Phosphate, tris (2-methacryloyloxyethyl) phosphate and the like can be mentioned.

Among these polyfunctional monomers, polyacrylates or polymethacrylates of trihydric or higher polyhydric alcohols and modified products of dicarboxylic acids thereof, specifically, trimethylolpropane triacrylate, trimethylolpropane Trimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate, the following formula ( The compounds represented by 2) are preferred, and particularly, trimethylolpropane triacrylate, pentaerythr Tall triacrylate and dipentaerythritol hexaacrylate, high pixel intensities, excellent smoothness of the pixel surface, and are unlikely to generate scumming and film remaining in the region other than a portion where pixels are formed.

[0020]

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The above-mentioned polyfunctional monomers can be used alone or in combination of two or more. The amount of the polyfunctional monomer used in the present invention is usually 5 to 500 parts by weight, preferably 20 to 300 parts by weight, based on 100 parts by weight of the alkali-soluble resin (B). In this case, if the used amount is less than 5 parts by weight, the strength and surface smoothness of the obtained pixels tend to decrease, while if it exceeds 500 parts by weight, for example, the alkali developability decreases, There is a tendency for background contamination and film residue to occur easily in a region other than the portion where the pixels are formed. In the present invention,
If necessary, a monofunctional monomer may be used in combination with the polyfunctional monomer. Specific examples of such a monofunctional monomer include carboxyl group-containing unsaturated monomers and copolymerizable unsaturated monomers exemplified for the carboxyl group-containing copolymer, and commercially available M −53
00 (trade name, manufactured by Toagosei Co., Ltd.) and the like. These monofunctional monomers can be used alone or in combination of two or more. The use ratio of the monofunctional monomer is usually 90% by weight or less, preferably 0 to 0% by weight, based on the total of the polyfunctional monomer and the monofunctional monomer.
50% by weight. In this case, if the use ratio exceeds 90% by weight, the strength and surface smoothness of the obtained pixels may be insufficient.

(D) Photopolymerization initiator The photopolymerization initiator in the present invention includes visible light, ultraviolet light,
Irradiation of radiation such as far ultraviolet rays, electron beams and X-rays (hereinafter referred to as "exposure") causes decomposition or cleavage of bonds, and polymerization of the (C) polyfunctional monomers such as radicals, cations and anions. Means a compound that generates an active species capable of initiating Examples of such a photopolymerization initiator include imidazole compounds having at least one main skeleton represented by the following formula (3), formula (4) or formula (5), benzoin compounds, acetophenone compounds, Benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, xanthone compounds, diazo compounds,
Triazine compounds and the like can be mentioned.

[0023]

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Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,
4 ′, 5,5 ′ {tetrakis (4-methoxycarbonylphenyl) -1,2′-biimidazole, 2,2′-
Bis (2-chlorophenyl) -4,4 ', 5,5'
Tetrakis (4-ethoxycarbonylphenyl) -1,
2′-biimidazole, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) -1,2′-biimidazole, 2,2′- Bis (2,4-dichlorophenyl)-
4,4 ′, 5,5′-tetrakis (4-methoxycarbonylphenyl) -1,2′-biimidazole, 2,2 ′
-Bis (2,4-dichlorophenyl) -4,4 ', 5
5'-tetrakis (4-ethoxycarbonylphenyl)
-1,2'-biimidazole, 2,2'-bis (2,4
-Dichlorophenyl) -4,4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) -1,2'-
Biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4 ', 5,5'-tetrakis (4
-Methoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl)- 1,2′-biimidazole,
2,2'-bis (2,4,6-trichlorophenyl)-
4,4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) -1,2′-biimidazole, 2,
2'-bis (2-bromophenyl) -4,4 ', 5
5′──tetrakis (4-methoxycarbonylphenyl) -1,2′-biimidazole, 2,2′-bis (2
-Bromophenyl) -4,4 ', 5,5' {tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-bromophenyl)
-4,4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) -1,2'-biimidazole, 2,
2′-bis (2,4-dibromophenyl) -4,4 ′,
5,5'-tetrakis (4-methoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2,4-dibromophenyl) -4,4 ', 5,5'-
Tetrakis (4-ethoxycarbonylphenyl) -1,
2'-biimidazole, 2,2'-bis (2,4-dibromophenyl) -4,4 ', 5,5'-tetrakis (4
-Phenoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2,4,6-tribromophenyl) -4,4 ', 5,5'-tetrakis (4-methoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2,4,6-tribromophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2' -Biimidazole,
2,2'-bis (2,4,6-tribromophenyl)-
4,4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) -1,2′-biimidazole, 2,
2'-bis (2-cyanophenyl) -4,4 ', 5.
5'-tetrakis (4-methoxycarbonylphenyl)
-1,2'-biimidazole, 2,2'-bis (2-cyanophenyl) -4,4 ', 5.5'-tetrakis (4
-Ethoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-bis (2-cyanophenyl) -4,
4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-
Bis (2-methylphenyl) -4,4 ′, 5,5′-tetrakis (4-methoxycarbonylphenyl) -1,
2′-biimidazole, 2,2′-bis (2-methylphenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2,2 ′ -Bis (2-methylphenyl) -4,
4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-
Bis (2-ethylphenyl) -4,4 ′, 5,5′-tetrakis (4-methoxycarbonylphenyl) -1,
2′-biimidazole, 2,2′-bis (2-ethylphenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2,2 ′ -Bis (2-ethylphenyl) -4,
4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) -1,2'-biimidazole, 2,2'-
Bis (2-phenylphenyl) -4,4 ', 5,5'-
Tetrakis (4-methoxycarbonylphenyl) -1,
2′-biimidazole, 2,2′-bis (2-phenylphenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2,2 ′ -Bis (2-phenylphenyl) -4,
4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) -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′-tetraphenyl-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'-tetraphenyl -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, 2,2'-bis (2-cyanophenyl) -4,
4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-dicyanophenyl)
-4,4 ', 5,5'-Tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-tricyanophenyl) -4,4', 5,5'- Tetraphenyl-
1,2′-biimidazole, 2,2′-bis (2-methylphenyl) -4,4 ′, 5,5′-tetraphenyl-
1,2′-biimidazole, 2,2′-bis (2,4-
Dimethylphenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2,4,6-trimethylphenyl) -4,4 ′, 5
5′-tetraphenyl-1,2′-biimidazole,
2,2′-bis (2-ethylphenyl) -4,4 ′,
5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4-diethylphenyl)-
4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-triethylphenyl) -4,4', 5,5'-tetraphenyl −
1,2′-biimidazole, 2,2′-bis (2-phenylphenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2′-bis (2 , 4
-Diphenylphenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-triphenylphenyl) -4,4',
5,5′-tetraphenyl-1,2′-biimidazole and the like can be mentioned.

Of these biimidazole compounds,
In particular, 2,2'-bis (2-chlorophenyl) -4,
4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole, 2,2′-bis (2-bromophenyl) -4,4 ′, 5,5′-tetrakis ( 4-ethoxycarbonylphenyl) -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, 2,2'-bis (2,4-dibromophenyl) -4,4', 5,5 '
-Tetraphenylbi-1,2'-imidazole and 2,2'-bis (2,4,6-tribromophenyl)-
4,4 ', 5,5'-Tetraphenyl-1,2'-biimidazole is preferred. The biimidazole-based compound is excellent in solubility in a solvent, does not generate foreign matters such as undissolved substances and precipitates, and has high sensitivity. Since the curing reaction is high and no curing reaction occurs in the unexposed area, the coated film after exposure is clearly divided into a cured area insoluble in the developer and an uncured area having a high solubility in the developer. As a result, a pixel pattern without undercuts can be obtained, and a high-definition pixel array in which the pixels are arranged according to a predetermined arrangement can be formed.

Specific examples of the benzoin compound include benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin isobutyl ether, and methyl-2-benzoylbenzoate. Specific examples of the acetophenone-based compound include 2,2-dimethoxy-2-phenylacetophenone and 2-hydroxy-
2-methyl-1-phenylpropan-1-one, 1-
(4-i-propylphenyl) -2-hydroxy-2-
Methylpropan-1-one, 4- (2-hydroxyethoxy) phenyl- (2-hydroxy-2-propyl) ketone, 2,2-dimethoxyacetophenone, 2,2-diethoxyacetophenone, 2-methyl- (4- Methylthiophenyl) -2-morpholino-1-propane-1-
On, 2-benzyl-2-dimethylamino-1- (4-
Morpholinophenyl) butan-1-one, 1-hydroxycyclohexylphenyl ketone, 2,2'-dimethoxy-1,2-diphenylethan-1-one, 4-azidoacetophenone, 4-azidobenzalacetophenone, and the like. Can be. Specific examples of the benzophenone-based compound include benzophenone, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and 3,3′-dimethyl-4-methoxybenzophenone. Can be. Specific examples of the α-diketone compound include diacetyl, dibenzoyl, methylbenzoyl formate and the like. Specific examples of the polynuclear quinone compound include anthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone, and 1,4-naphthoquinone. Specific examples of the xanthone-based compound include xanthone, thioxanthone,
Examples thereof include 4-diethylthioxanthone and 2-chlorothioxanthone. Specific examples of the diazo compound include 4-diazodiphenylamine, 4-diazo-4′-methoxydiphenylamine, 4-diazo-3-
Methoxydiphenylamine and the like can be mentioned. Specific examples of the triazine-based compound include 2- (2′-
Furylethylidene) -4,6-bis (trichloromethyl) -s-triazine, 2- (3 ′, 4′-dimethoxystyryl) -4,6-bis (trichloromethyl) -s-
Triazine, 2- (4'-methoxynaphthyl) -4,6
-Bis (trichloromethyl) -s-triazine, 2-
(2′-bromo-4′-methylphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (2 ′
-Thiophenylethylidene) -4,6-bis (trichloromethyl) -s-triazine and the like.
Further, as other photopolymerization initiators, 4-azidobenzaldehyde, azidopyrene, bis (2,6-dimethoxybenzoyl) -2,4,4-trimethylpentylphosphine oxide, N-phenylthioacridone,
Triphenylpyrylium perchlorate and the like can also be used.

These photopolymerization initiators can be used alone or
A mixture of more than one species can be used. The amount of the photopolymerization initiator used in the present invention is usually 0.01 to 200 parts by weight based on 100 parts by weight of the total of the polyfunctional monomer (C) and the optionally used monofunctional monomer. It is preferably 1 to 120 parts by weight, particularly preferably 1 to 50 parts by weight. In this case, if the use amount of the photopolymerization initiator is less than 0.01 part by weight, curing by exposure becomes insufficient, and it may be difficult to obtain a pixel array arranged according to a predetermined arrangement. When the amount is more than the weight part, the formed pixels are likely to fall off the substrate during development, and background contamination or a film residue is more likely to occur in a region on the substrate other than the portion where the pixels are formed.

Further, in the present invention, if necessary, a sensitizer, a curing accelerator or a polymer photocrosslinking / sensitizer (hereinafter, these components are collectively referred to as “curing agent”) together with the photopolymerization initiator. ) May be used in combination. Specific examples of the sensitizer include 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, ethyl-4-dimethylaminobenzoate,
Ethylhexyl-1,4-dimethylaminobenzoate, 2,5-bis (4'-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, and the like. it can. These sensitizers can be used alone or in combination of two or more. Specific examples of the curing accelerator include 2-mercaptobenzimidazole, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2,5
-Dimercapto-1,3,4-thiadiazole, 2-mercapto-4,6-dimethylaminopyridine, 1-phenyl-5-mercapto-1H-tetrazole, 3-mercapto-4-methyl-4H-1,2,4 A chain transfer agent such as triazole. These curing accelerators can be used alone or in combination of two or more. Further, the polymer photocrosslinking / sensitizer is a polymer compound having at least one kind of functional group capable of acting as a crosslinking agent and / or a sensitizer upon exposure in a main chain and / or a side chain, Specific examples thereof include a condensate of 4-azidobenzaldehyde and polyvinyl alcohol, a condensate of 4-azidobenzaldehyde and a phenol novolak resin, and a homopolymer or copolymer of 4-acryloylphenylcinnamoyl ester; −
Examples thereof include polybutadiene and 1,2-polybutadiene. These polymer photocrosslinking / sensitizers can be used alone or in combination of two or more. The amount of the curing aid used is usually 300 parts by weight or less, preferably 5-200 parts by weight, per 100 parts by weight of the photopolymerization initiator (D).
Parts by weight, more preferably 10 to 100 parts by weight.
In the present invention, the use of a combination of a biimidazole-based compound and a benzophenone-based compound and / or a thiazole-based curing accelerator as the photopolymerization initiator makes it difficult for the formed pixels to fall off the substrate during development. This is preferable in that the pixel intensity and sensitivity are also increased. In the present invention, when a biimidazole-based compound is used in combination with another component as a photopolymerization initiator, the proportion of the other component used is preferably 80% by weight or less of the entire photopolymerization initiator.

Here, a particularly preferred photopolymerization initiator in the present invention is shown as a combination of its components.
The following can be mentioned. That is, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'
-Biimidazole / 4,4'-bis (diethylamino)
Benzophenone, 2,2'-bis (2-chlorophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole /
4,4'-bis (diethylamino) benzophenone / 2
-Benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2,2'-bis (2
-Chlorophenyl) -4,4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) -1,2'-biimidazole / 4,4'-bis (diethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone, , 2'-bis (2-chlorophenyl) -4,
4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) -1,2′-biimidazole / 4,4′-bis (dimethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone / 2-mercaptobenzothiazole, 2,2'-bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'
-Biimidazole / 4,4'-bis (diethylamino)
Benzophenone, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,
2'-biimidazole / 4,4'-bis (diethylamino) benzophenone / 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 2,2'-bis (2 4-dichlorophenyl)-
4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole / 4,4'-bis (diethylamino) benzophenone / 2-benzyl-2-dimethylamino-1-
(4-morpholinophenyl) butan-1-one / 2-
Mercaptobenzothiazole, 2,2′-bis (2,4
-Dibromophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole / 4,4'-bis (diethylamino) benzophenone / 2-benzyl-2
-Dimethylamino-1- (4-morpholinophenyl)
Butan-1-one, 2,2'-bis (2,4-dibromophenyl) -4,4 ', 5,5'-tetraphenyl-
1,2′-biimidazole / 4,4′-bis (diethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone, 2,2′-bis (2,4,6-trichlorophenyl) -4,4 ′, 5 5'-tetraphenyl-1,2'-biimidazole / 4,4'-bis (dimethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone / 2-mercaptobenzothiazole.

Other Additives The radiation-sensitive composition for a color filter of the present invention may contain an organic acid in order to further improve its solubility in an alkali developing solution and to further suppress remaining undissolved matter after development. Can be contained. As such an organic acid, an aliphatic carboxylic acid or a phenyl group-containing carboxylic acid having a molecular weight of 1,000 or less is preferable. Specific examples of the aliphatic carboxylic acid, formic acid, acetic acid, propionic acid, butyric acid,
Monocarboxylic acids such as valeric acid, pivalic acid, caproic acid, diethylacetic acid, enanthic acid, caprylic acid; oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, Dicarboxylic acids such as brassic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid, cyclohexanedicarboxylic acid, itaconic acid, citraconic acid, maleic acid, fumaric acid and mesaconic acid; tricarballylic acid And tricarboxylic acids such as aconitic acid and camphoronic acid.

Examples of the phenyl group-containing carboxylic acid include an aromatic carboxylic acid having a carboxyl group directly bonded to a phenyl group, and a carboxylic acid having a carboxyl group bonded to a phenyl group via a carbon chain. Specific examples thereof include aromatic monocarboxylic acids such as benzoic acid, toluic acid, cumic acid, hemelitic acid, and mesitylene acid; aromatic dicarboxylic acids such as phthalic acid, isophthalic acid, and terephthalic acid; trimellitic acid and trimesin Trivalent or higher aromatic polycarboxylic acids such as acid, melophanic acid and pyromellitic acid, phenylacetic acid, hydroatropic acid, hydrocinnamic acid, mandelic acid, phenylsuccinic acid, atropic acid, cinnamic acid, cinnamylidenic acid and coumaric acid Acids, umbellic acid, and the like. Of these organic acids,
Aliphatic dicarboxylic acids and aromatic dicarboxylic acids such as malonic acid, adipic acid, itaconic acid, citraconic acid, fumaric acid, mesaconic acid, and phthalic acid are alkali-soluble, soluble in solvents, and pixels on the substrate are formed. It is preferable from the viewpoint of prevention of background contamination and film residue in a region other than the portion. The organic acids can be used alone or in combination of two or more. The amount of the organic acid to be used is generally 10% by weight or less, preferably 5% by weight or less, more preferably 1% by weight or less, based on the whole radiation-sensitive composition.
In this case, if the amount of the organic acid used exceeds 10% by weight, the adhesion of the formed pixel to the substrate tends to decrease.

Further, the radiation-sensitive composition for a color filter of the present invention may contain various additives other than the organic acid, if necessary. Examples of such additives include dispersing aids such as blue pigment derivatives and yellow pigment derivatives such as copper phthalocyanine derivatives; fillers such as glass and alumina; polyvinyl alcohol, polyethylene glycol monoalkyl ethers, and poly (fluoroalkyl). High molecular compounds such as acrylates); vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2
-Methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N
-(2-aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane,
3-glycidoxypropyltrimethoxysilane, 3-glycidylpropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane,
Adhesion promoters such as -chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane and 3-mercaptopropyltrimethoxysilane; 2,2-thiobis (4
-Methyl-6-t-butylphenol), 2,6-di-
an antioxidant such as t-butylphenol; 2- (3-t-
Butyl-5-methyl-2-hydroxyphenyl) -5
UV absorbers such as chlorobenzotriazole and alkoxybenzophenones; aggregation inhibitors such as sodium polyacrylate; and thermal crosslinking agents such as epoxy compounds, melamine compounds and bisazide compounds.

Solvent The radiation-sensitive composition for a color filter of the present invention contains the above-mentioned components (A) to (D) as essential components and optionally contains other additives. It is prepared as a composition. As the solvent, dissolve or disperse each component constituting the radiation-sensitive composition, and do not react with these components, as long as it has a moderate volatility,
It can be appropriately selected and used. Specific examples of such a solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and diethylene glycol mono-ethyl. n-propyl ether, diethylene glycol mono-n-butyl ether, triethylene glycol monomethyl ether,
Triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n
-Propyl ether, propylene glycol mono-n-
Butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether,
Dipropylene glycol mono-n-propyl ether,
(Poly) alkylene glycol monoalkyl ethers such as dipropylene glycol mono-n-butyl ether, tripropylene glycol monomethyl ether and tripropylene glycol monoethyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, propylene glycol monomethyl ether (Poly) alkylene glycol monoalkyl ether acetates such as acetate and propylene glycol monoethyl ether 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; methyl 2-hydroxypropionate and ethyl 2-hydroxypropionate Lactic acid alkyl esters; 2-hydroxy-2
-Ethyl methyl propionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, ethyl ethoxyacetate, ethyl hydroxyacetate,
Methyl-hydroxy-3-methylbutanoate, 3-methyl-3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl acetate, n-butyl acetate, i-butyl acetate, n-amyl formate; I-Amyl acetate, n-butyl propionate, i-propyl butyrate, ethyl butyrate, n-butyl butyrate, methyl pyruvate, ethyl pyruvate, n-propyl pyruvate, methyl acetoacetate, ethyl acetoacetate, 2-oxobutanoic acid Other esters such as ethyl; aromatic hydrocarbons such as toluene and xylene; amides such as N-methylpyrrolidone, N, N-dimethylformamide and N, N-dimethylacetamide. Of these solvents, solubility,
From the viewpoint of pigment dispersibility, coatability, etc., ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether,
Cyclohexanone, 2-heptanone, 3-heptanone,
Ethyl 2-hydroxypropionate, 3-methyl-3-
Methoxybutyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, n-butyl acetate, i-acetate
Butyl, n-amyl formate, i-amyl acetate, n-butyl propionate, ethyl butyrate, i-propyl butyrate, n-butyrate
-Butyl, ethyl pyruvate and the like are preferred. The solvents can be used alone or in combination of two or more.

Further, benzyl ethyl ether, dihexyl ether, acetonylacetone,
Isophorone, caproic acid, caprylic acid, 1-octanol, 1-nonanol, benzyl alcohol, benzyl acetate, ethyl benzoate, diethyl oxalate, diethyl maleate, γ-butyrolactone, ethylene carbonate, propylene carbonate, phenyl cellosolve acetate, etc. A boiling point solvent can be used in combination. Of these high boiling solvents,
γ-butyrolactone is preferred. The high boiling solvent,
They can be used alone or in combination of two or more. The amount of the solvent used is not particularly limited,
In light of the applicability and stability of the obtained radiation-sensitive composition, the total concentration of components excluding the solvent in the composition is usually 5 to 50% by weight, and preferably 10 to 40% by weight. A ratio is desirable.

[0036]

Embodiments of the present invention will be described below more specifically with reference to examples. However, the present invention is not limited to the following examples.

EXAMPLES Example 1 (A) CI Pigment Violet 19 as Colorant
100 parts by weight of a mixture having a weight ratio of 75/25 with CI Pigment Orange 71; (B) a methacrylic acid / 2-hydroxyethyl methacrylate / benzyl methacrylate copolymer (copolymer weight ratio = 15 /
15/70, Mw = 28,000) 60 parts by weight, (C)
40 parts by weight of dipentaerythritol hexaacrylate as a polyfunctional monomer, (D) 2,2 as a photopolymerization initiator
2'-bis (2,4-dichlorophenyl) -4,4 ',
A mixture of 10 parts by weight of 5,5 ′ イ tetraphenyl-1,2′-biimidazole, 10 parts by weight of 4,4′-bis (diethylamino) benzophenone, and 1000 parts by weight of ethyl 3-ethoxypropionate as a solvent is mixed. A liquid composition of a radiation-sensitive composition was prepared. [Manufacture of Color Filter] Using the above liquid composition, a red striped color filter was manufactured on a transparent substrate as follows. The liquid composition is applied using a spin coater on the surface of a soda glass substrate on which a SiO ₂ film for preventing sodium ions from being eluted is formed, and then prebaked in a clean oven at 80 ° C. for 10 minutes. Was performed to form a coating film having a thickness of 0.8 μm. Then, after cooling the substrate to room temperature, the coating film was coated with 365 n using a high pressure mercury lamp through a photomask.
m, 405 nm and 436 nm were exposed at an exposure dose of 200 mJ / cm ² . Next, the substrate was immersed in a 0.04% by weight aqueous solution of potassium hydroxide at 23 ° C. for 1 minute, developed, washed with ultrapure water,
Dried. Then, in a 230 ° C. clean oven,
Post baking was performed for 0 minutes to produce a red striped color filter on a soda glass substrate. [Evaluation of Color Filter] The obtained color filters were evaluated as follows. Heat resistance immediately after production of the color filter chromaticity (alpha) and the chromaticity after 1 hour heat treatment at 250 ° C. of the color filter (beta)
Using a microanalyzer ("TC-1" manufactured by Tokyo Denshoku Co., Ltd.)
800M ”), and the heat resistance was evaluated based on the color difference (ΔEab) between chromaticity (β) and chromaticity (α). As a result, ΔEab was 1.75. Light resistance A color filter manufactured in the same manner as described above was exposed to ultraviolet light using an ultraviolet long life fade meter (manufactured by Suga Test Instruments Co., Ltd.), and chromaticity (γ) after 90 hours of exposure was measured.
Using a microanalyzer ("TC-1" manufactured by Tokyo Denshoku Co., Ltd.)
800M ”), and the light resistance was evaluated based on the color difference (ΔEab) between the chromaticity (γ) and the chromaticity (α) of the color filter immediately after production. As a result, ΔEab was 1.85. Spectral transmittance The spectral transmittance of the color filter was measured using a microanalyzer ("TC-1800M" manufactured by Tokyo Denshoku Co., Ltd.). FIG. 1 shows the measurement results. This color filter has a transmittance at a wavelength of 500 nm or less and 610
The transmittance at the wavelength of nm was maintained at a high level.

Comparative Example 1 (A) CI Pigment Red 177 and CI
Preparation of a liquid composition, production of a color filter, and evaluation of a color filter were performed in the same manner as in Example 1 except that 100 parts by weight of a mixture having a weight ratio of 70/30 with Pigment Violet 23 was used. As a result, the heat resistance ΔEab of this color filter was 2.10, and the light resistance ΔEab was 2.31, and the heat resistance and light resistance were insufficient. FIG. 2 shows the measurement results of the spectral transmittance of the color filter. This color filter had low transmittance at a wavelength of 500 nm or less and transmittance at a wavelength of 610 nm.

Comparative Example 2 (A) CI Pigment Red 177 and CI
Pigment Yellow 83, except that 100 parts by weight of a mixture having a weight ratio of 90/10 was used.
Preparation of a liquid composition, production of a color filter, and evaluation of the color filter were performed. As a result, the heat resistance ΔEab of this color filter was 2.05, and the light resistance ΔEab was 2.
12, which was insufficient in heat resistance and light resistance. FIG. 3 shows the measurement results of the spectral transmittance of the color filter. This color filter had particularly low transmittance at a wavelength of 500 nm or less.

[0039]

The radiation-sensitive composition for a color filter of the present invention has excellent heat resistance and light resistance, and has a spectral transmittance optimized in accordance with the spectrum of ambient light. An additive color mixture type color filter optimal for a liquid crystal display device can be provided.

[Brief description of the drawings]

FIG. 1 is a diagram illustrating a measurement result of a spectral transmittance of a color filter manufactured using the radiation-sensitive composition for a color filter of the present invention.

FIG. 2 is a diagram illustrating a measurement result of a spectral transmittance of a color filter manufactured using a radiation-sensitive composition for comparison.

FIG. 3 is a diagram illustrating a measurement result of a spectral transmittance of a color filter manufactured using another comparative radiation-sensitive composition for comparison.

Claims (2)

[Claims] 1. A radiation-sensitive composition for a color filter comprising (A) a colorant, (B) an alkali-soluble resin, (C) a polyfunctional monomer, and (D) a photopolymerization initiator.
(A) A radiation-sensitive composition for an additive color mixture type color filter for use in a reflective color liquid crystal display device, wherein the colorant contains a quinacridone pigment represented by the following structural formula (1). Embedded image [In the structural formula (1), R ^{1 to} R ⁸ each independently represent a hydrogen atom, a methyl group or a chlorine atom. ] 2. A radiation-sensitive composition for a color filter, comprising (A) a colorant, (B) an alkali-soluble resin, (C) a polyfunctional monomer, and (D) a photopolymerization initiator.
(A) A radiation sensitivity for an additive color mixture type color filter used in a reflective color liquid crystal display device, wherein the colorant comprises a mixture of a quinacridone pigment represented by the following structural formula (1) and an orange pigment. Composition. [In the structural formula (1), R ^{1 to} R ⁸ each independently represent a hydrogen atom, a methyl group or a chlorine atom. ]