JPH1144815A - Radiation sensitive composition for color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a compsn. having excellent white balance and excellent heat resistance and light resistance by incorporating an org. pigment containing a specified quinacridone pigment, alkali soluble resin, polyfunctional monomers and photopolymn. initiator. SOLUTION: The compsn. contains an org. pigment containing a quinacridone pigment expressed by formula I, alkali soluble resin, polyfunctional monomers and photopolymn. initiator. In formula I, R<1> to R<8> are independently hydrogen atoms, methyl groups or chlorine atoms. As for an example of the quinacridone pigment, compds. expressed by formula II or the like with a specified color index as classified as a pigment in a color index can be used. Thereby, the obtd. radiation sensitive compsn. has excellent heat resistance, light resistance and shows excellent white balance and is to be used for the production of a color-reducing mixing type color filter for a reflection type color liquid crystal display device.

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 which contains a quinacridone pigment and is used for producing a subtractive color filter used in 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 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. Further, as a color filter used in a color liquid crystal display device today, an additive color mixture type of three primary colors of general red (R), green (G) and blue (B) is generally used. As a composition for forming a red color used for producing a color filter used in a liquid crystal display device, JP-A-9-68608 discloses a CI pigment red 48: 1, 48: 2, 48: 3 having a color index number. It is disclosed that a coloring composition having excellent heat resistance, light resistance and color purity can be obtained by using a chelated azo pigment such as 48: 4. On the other hand, a subtractive color filter using three colors of cyan (C), magenta (M), and yellow (Y), which are complementary colors, has been announced for the reflective color liquid crystal display device. However, the organic pigment used in the additive color mixture type color filter used in the transmission type color liquid crystal display device and the reflection type color liquid crystal display device is replaced with the subtractive color mixture type color filter used in the reflection type color liquid crystal display device. If used for
Inferior in white balance, as disclosed in JP-A-9-68608
The coloring composition used in the additive color mixture type color filter disclosed in Japanese Patent Application Laid-Open No. H10-158400 is also insufficient in terms of white balance. Accordingly, there has been a strong demand for the development of a subtractive color filter used in a reflective color liquid crystal display device having excellent white balance in addition to heat resistance and light resistance.

[0003]

SUMMARY OF THE INVENTION An object of the present invention is to provide a subtractive color filter used in a reflective color liquid crystal display device having excellent heat resistance and light resistance and having an excellent white balance. To provide a radiation-sensitive composition.

[0004]

The present invention provides (A) an organic pigment containing a quinacridone pigment represented by the following structural formula (1), (B) an alkali-soluble resin,
It comprises a subtractive color mixing type radiation-sensitive composition for a color filter, which comprises (C) a polyfunctional monomer and (D) a photopolymerization initiator.

[0005]

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. ]

(A) Organic Pigment The organic pigment of the present invention contains at least one quinacridone pigment represented by the structural formula (1) (hereinafter, referred to as “quinacridone pigment (A1)”). It is. Specific examples of the quinacridone pigment (A1) include a color index (CI; The Society of Dyers).
and Colorists).
The following color index (CI) numbers classified into t) are given, and examples thereof include compounds represented by the following structural formulas (2) to (5). In addition, following each color index (CI) number, a compound name and a color tone are also described in parentheses.

CI Pigment Violet 19 (quinacridone; purple-β form, red-γ form)

Embedded image

CI Pigment Red 122 (2,9-dimethylnacridone; magenta)

Embedded image ,

CI Pigment Red 202 (2,9-dichloronacridone; purple red)

Embedded image ,

[0011] CI Pigment Red 209 (3, 10-
Dichloronacridone; red)

Embedded image .

The quinacridone pigment (A1) can be used as a mixture or solid solution of two or more thereof, or a mixture or solid solution of one or more thereof and one or more other organic pigments. Among such mixtures or solid solutions, specific examples of pigments with color index numbers include CI Pigment Red 207.
(Yellow red) (solid solution of quinacridone and a compound represented by the following structural formula (6)), CI Pigment Red 206
(Red-brown) (solid solution of quinacridone and a compound represented by the following structural formula (7)).

[0013]

Embedded image ,

[0014]

Embedded image ,

Further, the quinacridone pigment (A1) in the present invention is used for adjusting the color tone of the obtained pixel.
The yellow organic pigment may be contained in a proportion of 20% by weight or less, preferably 0 to 10% by weight of the total pigment component. Examples of the yellow organic pigments include those having the following color index (CI) numbers. CI Pigment Yellow 1, CI Pigment Yellow 3, CI Pigment Yellow 12, CI
Pigment Yellow 13, CI Pigment Yellow 1
4, CI Pigment Yellow 16, CI Pigment Yellow 17, CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 31, CI Pigment Yellow 55, CI Pigment Yellow 60,
CI Pigment Yellow 65, CI Pigment Yellow 73, CI Pigment Yellow 74, CI Pigment Yellow 81, CI Pigment Yellow 83, CI Pigment Yellow 93, CI Pigment Yellow 95, CI
Pigment Yellow 97, CI Pigment Yellow 9
8, CI Pigment Yellow 100, CI Pigment Yellow 101, CI Pigment Yellow 104, CI Pigment Yellow 106, CI Pigment Yellow 10
8, CI Pigment Yellow 109, CI Pigment Yellow 110, CI Pigment Yellow 113, CI Pigment Yellow 114, CI Pigment Yellow 11
6, CI Pigment Yellow 117, CI Pigment Yellow 119, CI Pigment Yellow 120, CI Pigment Yellow 126, CI Pigment Yellow 12
7, CI Pigment Yellow 128, CI Pigment Yellow 129, CI Pigment Yellow 138, CI Pigment Yellow 139, CI Pigment Yellow 15
0, CI Pigment Yellow 151, CI Pigment Yellow 152, CI Pigment Yellow 153, CI Pigment Yellow 154, CI Pigment Yellow 15
6, CI Pigment Yellow 166, CI Pigment Yellow 168, CI Pigment Yellow 175, and the like. These yellow organic pigments can be used alone or in combination of two or more.

In the present invention, the surface of each of the organic pigments can be modified with a polymer before use. Examples of the polymer for modifying the surface of the organic pigment include, for example, JP-A-8-
Examples thereof include polymers described in JP-A-259876 and various commercially available polymers or oligomers for dispersing pigments. Further, the organic pigment in the present invention can be used together with a dispersant, if desired. Examples of such a dispersant include cationic, anionic, nonionic, amphoteric, silicone-based, and fluorine-based surfactants. Specific examples of the surfactant include polyoxyethylene alkyl ethers such as polyoxyethylene lauryl ether, polyoxyethylene stearyl ether and polyoxyethylene oleyl ether; polyoxyethylene octyl phenyl ether, polyoxyethylene nonyl phenyl ether and the like. Polyoxyethylene alkyl phenyl ethers; polyethylene glycol diesters such as polyethylene glycol dilaurate and polyethylene glycol distearate; sorbitan fatty acid esters; fatty acid-modified polyesters; tertiary amine-modified polyurethanes; KP (Shin-Etsu Chemical Co., Ltd.), Polyflow (Kyoeisha Chemical Co., Ltd.),
F-top (manufactured by Tochem Products), Megafac (manufactured by Dainippon Ink and Chemicals, Inc.), Florard (manufactured by Sumitomo 3M Limited), Asahi Guard, Surflon (above, manufactured by Asahi Glass Co., Ltd.), etc. be able to. These surfactants can be used alone or in combination of two or more. The amount of the surfactant used is the amount of the organic pigment 1
It is usually 50 parts by weight or less, preferably 0 to 30 parts by weight, based on 00 parts by weight.

(B) Alkali-Soluble Resin Next, the alkali-soluble resin in the present invention includes:
(A) as long as it acts as a binder for the organic pigment and is soluble in a developing solution used in the developing step, particularly preferably an alkali developing solution, when 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”) and another copolymerizable ethylenically unsaturated monomer (hereinafter, referred to as “monomer”) (Hereinafter simply referred to as “carboxyl group-containing copolymer”) is preferable. Examples of the carboxyl group-containing unsaturated monomer include, for example, unsaturated monocarboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, α-chloroacrylic acid, and cinnamic acid; maleic acid, maleic anhydride, fumaric acid, Unsaturated dicarboxylic acids such as itaconic acid, itaconic anhydride, citraconic acid, citraconic anhydride and mesaconic acid or anhydrides thereof; trivalent or higher unsaturated polycarboxylic acids or anhydrides thereof; 2-acryloyloxyethyl Mono [(meth) acryloyloxyalkyl] esters of divalent or higher polycarboxylic acids such as succinic acid and 2-methacryloyloxyethyl succinic acid; ω-carboxypolycaprolactone monoacrylate, ω-carboxypolycaprolactone monomethacrylate Mono (meth) acrylates of dicarboxy polymer at both ends such as It is possible. These carboxyl group-containing unsaturated monomers can be used alone or in combination of two or more.

Examples of the copolymerizable unsaturated monomer include styrene, α-methylstyrene, o-vinyltoluene, m-vinyltoluene, p-vinyltoluene, p-chlorostyrene, and o-methoxystyrene. , M-
Methoxystyrene, p-methoxystyrene, indene,
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, 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, methoxytriethylene glycol acrylate, methoxytriethylene glycol methacrylate, methoxypropylene glycol acrylate, methoxypropylene glycol methacrylate, methoxydipropylene glycol acrylate, methoxydipropylene glycol methacrylate, isobornyl acrylate , Isobornyl methacrylate, dicyclopentadienyl acrylate,
Unsaturated carboxylic esters such as dicyclopentadienyl methacrylate, 2-hydroxy-3-phenoxypropyl acrylate, 2-hydroxy-3-phenoxypropyl methacrylate; 2-aminoethyl acrylate, 2-aminoethyl methacrylate, 2-amino Unsaturated carboxylic acid aminoalkyl esters such as propyl acrylate, 2-aminopropyl methacrylate, 3-aminopropyl acrylate and 3-aminopropyl methacrylate; unsaturated carboxylic acid glycidyl esters such as glycidyl acrylate and glycidyl methacrylate; vinyl acetate and propion Vinyl carboxylate such as vinyl acrylate, vinyl butyrate, vinyl benzoate; vinyl methyl ether, vinyl ethyl ether, allyl glycidyl ether, meta Unsaturated ethers such as glycidyl ethers; acrylonitrile, methacrylonitrile,
vinyl cyanide compounds such as α-chloroacrylonitrile and vinylidene cyanide; acrylamide, methacrylamide, α-chloroacrylamide, N-2-hydroxyethylacrylamide, N-2-hydroxyethylmethacrylamide, maleimide, N-phenylmaleimide,
Unsaturated amides or unsaturated imides such as N-cyclohexylmaleimide; aliphatic conjugated dienes such as 1,3-butadiene, isoprene, chloroprene; polystyrene, polymethyl acrylate, polymethyl methacrylate, poly-n-butyl acrylate, 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.

The carboxyl group-containing copolymer of the present invention essentially contains acrylic acid and / or methacrylic acid, and may further contain 2-acryloyloxyethyl succinic acid and / or 2-methacryloyloxyethyl succinic acid. Carboxyl group-containing unsaturated monomer component, styrene, methyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, allyl acrylate, allyl methacrylate, benzyl acrylate, benzyl methacrylate, N-phenylmaleimide, polystyrene macromonomer and Copolymer with at least one selected from the group of polymethyl methacrylate macromonomers (hereinafter, referred to as
It is referred to as “carboxyl group-containing copolymer (I)”. 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 / methyl (meth) acrylate / polystyrene macromonomer copolymer, (meth) acrylic acid / methyl (meth) acrylate / polymethylmethacrylate 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 / 2-acryloyloxy Ethyl succinic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / 2-acryloyloxyethylsuccinic acid / styrene / allyl methacrylate / N-phenylmaleimide copolymer It can be mentioned.

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 proportion of the alkali-soluble resin used in the present invention is usually 10 to 1000 parts by weight, preferably 20 to 500 parts by weight, based on 100 parts by weight of the organic pigment (A). In this case, if the use ratio is less than 10 parts by weight, for example, alkali developability may be reduced, and background contamination or a film residue may occur in a region other than a portion on which a pixel is formed on the substrate. If the amount exceeds the above range, the pigment concentration relatively decreases, so that 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 polyglycols; diacrylates or dimethacrylates of polyalkylene glycols such as polyethylene glycol and polypropylene glycol; trivalent or higher polyvalent such as glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol, etc. 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 Classes; diacrylate or dimethacrylates of hydroxyl-terminated polymers such as hydroxypolybutadiene, hydroxypolyisoprene, hydroxypolycaprolactone at both ends, trisacryloyloxyethyl phosphate, and trismethacryloyloxyethyl phosphate And the like.

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 hexaacrylate, dipentaerythritol hexamethacrylate, a compound represented by the following formula (8), and the like, are particularly preferable. Trimethylolpropane triacrylate, pentaerythritol triacrylate and dipentaerythritol hexaacrylate have higher pixel strength 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.

[0024]

Embedded image

The polyfunctional monomers can be used alone or in combination of two or more. In the present invention, if necessary, a monofunctional monomer may be used together 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 -5300 (trade name, manufactured by Toagosei Co., Ltd.). These monofunctional monomers can be used alone or in combination of two or more. The proportion of the monofunctional monomer used is usually 90% by weight or less, preferably 0 to 50% by weight, based on the total of the polyfunctional monomer and the monofunctional monomer. In this case, if the use ratio exceeds 90% by weight, the strength and surface smoothness of the obtained pixels may be insufficient. The total use ratio of the polyfunctional monomer and the monofunctional monomer in the present invention,
(B) The amount 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. In this case, if the use ratio is less than 5 parts by weight,
When the strength and surface smoothness of the obtained pixel tend to decrease, on the other hand, when the amount exceeds 500 parts by weight, for example, alkali developability decreases or background contamination in a region other than the portion where the pixel is formed on the substrate. And film residues tend to occur easily.

(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 (9), formula (10) or formula (11), benzoin compounds, acetophenone compounds,
Examples thereof include benzophenone compounds, α-diketone compounds, polynuclear quinone compounds, xanthone compounds, diazo compounds, and triazine compounds.

[0027]

Embedded image

Specific examples of the imidazole compound include 2,2'-bis (2-chlorophenyl) -4,
4 ′, 5,5 ′ {tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetrakis (4
-Phenoxycarbonylphenyl) biimidazole,
2,2′-bis (2,4-dichlorophenyl) -4,
4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2'-bis (2,4-
Dichlorophenyl) -4,4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4', 5,5 ' -Tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4,4 ', 5
5′-tetrakis (4-phenoxycarbonylphenyl) biimidazole, 2,2′-bis (2-cyanophenyl) -4,4 ′, 5.5′-tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2′-bis (2-cyanophenyl) -4,4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) biimidazole, 2,2′-bis (2-methylphenyl) -4,
4 ', 5,5'-tetrakis (4-methoxycarbonylphenyl) biimidazole, 2,2'-bis (2-methylphenyl) -4,4', 5,5'-tetrakis (4-
Ethoxycarbonylphenyl) biimidazole, 2,
2'-bis (2-methylphenyl) -4,4 ', 5
5′-tetrakis (4-phenoxycarbonylphenyl) biimidazole, 2,2′-bis (2-ethylphenyl) -4,4 ′, 5,5′-tetrakis (4-methoxycarbonylphenyl) biimidazole, 2, 2′-bis (2-ethylphenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2′-bis (2-ethylphenyl) -4,
4 ', 5,5'-tetrakis (4-phenoxycarbonylphenyl) biimidazole, 2,2'-bis (2-phenylphenyl) -4,4', 5,5'-tetrakis (4-methoxycarbonylphenyl) Biimidazole,
2,2′-bis (2-phenylphenyl) -4,4 ′,
5,5′-tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2′-bis (2-phenylphenyl) -4,4 ′, 5,5′-tetrakis (4-phenoxycarbonylphenyl) biimidazole,

2,2'-bis (2-chlorophenyl)-
4,4 ', 5,5' {tetraphenylbiimidazole, 2,2'-bis (2,4-dichlorophenyl)-
4,4 ′, 5,5′-tetraphenylbiimidazole,
2,2'-bis (2,4,6-trichlorophenyl)-
4,4 ′, 5,5′-tetraphenylbiimidazole,
2,2′-bis (2-bromophenyl) -4,4 ′,
5,5′-tetraphenylbiimidazole, 2,2′-
Bis (2,4-dibromophenyl) -4,4 ′, 5
5'-tetraphenylbiimidazole, 2,2'-bis (2,4,6-tribromophenyl) -4,4 ', 5
5'-tetraphenylbiimidazole, 2,2'-bis (2-cyanophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4-dicyanophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4,6-tricyanophenyl) -4,4', 5,5'-tetraphenylbiimidazole, , 2'-bis (2-methylphenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4-dimethylphenyl)-
4,4 ′, 5,5′-tetraphenylbiimidazole,
2,2'-bis (2,4,6-trimethylphenyl)-
4,4 ′, 5,5′-tetraphenylbiimidazole,
2,2′-bis (2-ethylphenyl) -4,4 ′,
5,5′-tetraphenylbiimidazole, 2,2′-
Bis (2,4-diethylphenyl) -4,4 ′, 5
5′-tetraphenylbiimidazole, 2,2′-bis (2,4,6-triethylphenyl) -4,4 ′, 5
5′-tetraphenylbiimidazole, 2,2′-bis (2-phenylphenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,4-
Diphenylphenyl) -4,4 ', 5,5'-tetraphenylbiimidazole, 2,2'-bis (2,4,6-
Triphenylphenyl) -4,4 ', 5,5'-tetraphenylbiimidazole and the like.

Of these biimidazole compounds,
In particular, 2,2'-bis (2-chlorophenyl) -4,
4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2'-bis (2-bromophenyl) -4,4', 5,5'-tetrakis (4-
Ethoxycarbonylphenyl) biimidazole, 2,
2'-bis (2-chlorophenyl) -4,4 ', 5
5′──tetraphenylbiimidazole, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5 ′
-Tetraphenylbiimidazole, 2,2'-bis (2,4-dibromophenyl) -4,4 ', 5,5'-
Tetraphenylbiimidazole, 2,2′-bis (2,
4,6-trichlorophenyl) -4,4 ', 5,5'-
Tetraphenylbiimidazole and 2,2′-bis (2,4,6-tribromophenyl) -4,4 ′, 5
5′-Tetraphenylbiimidazole 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. high,
Since the curing reaction does not occur in the unexposed area, the exposed coating film is clearly divided into a cured area insoluble in the developer and an uncured area having a high solubility in the developer. Accordingly, a pixel pattern without undercut 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 i-propyl ether, benzoin i-butyl ether, 4,4'-bis (dimethylamino) benzophenone, methyl- 2-benzoylbenzoate and the like can be mentioned. 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, 4-azidoacetophenone, 4-azidobenzalacetophenone and the like. 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. it can. 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, 2,4-diethylthioxanthone, and 2-chlorothioxanthone. Specific examples of the diazo compound include 4
-Diazodiphenylamine, 4-diazo-4'-methoxydiphenylamine, 4-diazo-3-methoxydiphenylamine and the like. 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 can be mentioned. Further, as a photopolymerization initiator other than the above, 4-azidobenzaldehyde,
Azidopyrene, bis (2,6-dimethoxybenzoyl)
It is also possible to use -2,4,4-trimethylpentylphosphine oxide, N-phenylthioacridone, triphenylpyrylium perchlorate and the like.

These photopolymerization initiators can be used alone or
A mixture of more than one species can be used. The proportion 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, when the use ratio 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, while the amount exceeds 200 parts by weight. In such a case, the formed pixels are likely to fall off the substrate during development, and background contamination and film residue are 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”) 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- A chain transfer agent such as dimethylaminopyridine can be used. These curing accelerators can be used alone or in combination of two or more. Also,
The polymer photocrosslinking / sensitizer is a polymer compound having at least one functional group capable of acting as a crosslinking agent and / or a sensitizer upon exposure in a main chain and / or a side chain. Examples include condensates of 4-azidobenzaldehyde and polyvinyl alcohol, condensates of 4-azidobenzaldehyde and phenol novolak resins,
A homopolymer or a copolymer of 4-acryloylphenylcinnamoyl ester, 1,4-polybutadiene,
Examples thereof include 1,2-polybutadiene. These polymer photocrosslinking / sensitizers can be used alone or in combination of two or more. The proportion of the curing aid used is usually based on 100 parts by weight of the photopolymerization initiator (D).
It is 300 parts by weight or less, preferably 5-200 parts by weight, more preferably 10-100 parts by weight. In the present invention, the use of a combination of a biimidazole compound and a benzophenone compound and / or a thiazole curing accelerator, in particular, as a photopolymerization initiator makes it difficult for 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) biimidazole / 4,4'-bis (diethylamino) benzophenone, 2,2' -Bis (2-chlorophenyl) -4,
4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) biimidazole / 4,4'-bis (diethylamino) benzophenone / 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butane- 1
-One, 2,2'-bis (2-chlorophenyl) -4,
4 ', 5,5'-tetrakis (4-ethoxycarbonylphenyl) biimidazole / 4,4'-bis (diethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone, 2,2'-bis (2-chlorophenyl) -4 , 4 ', 5,5'-Tetrakis (4-ethoxycarbonylphenyl) biimidazole / 4,4'-bis (dimethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone / 2-mercaptobenzothiazole, 2,2'- Bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole / 4,4'-bis (diethylamino) benzophenone, 2,2'-bis (2,4-dibromophenyl)-
4,4 ', 5,5'-tetraphenylbiimidazole /
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'-
Tetraphenylbiimidazole / 4,4'-bis (diethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone, 2,2'-bis (2,4,6-
(Trichlorophenyl) -4,4 ', 5,5'-tetraphenylbiimidazole / 4,4'-bis (dimethylamino) benzophenone / 1-hydroxycyclohexylphenyl ketone / 2-mercaptobenzothiazole.

Other Additives The radiation-sensitive composition for a color filter of the present invention contains an organic acid in order to further improve its solubility in an alkali developing solution and to suppress the remaining of undissolved material 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 , Aconitic acid, camphoronic acid and the like.

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 proportion of the organic acid used is usually 10% by weight or less, preferably 0.001 to 10% by weight, more preferably 0.01% by weight, based on the whole radiation-sensitive composition.
１1% by weight. In this case, when the use ratio exceeds 10% by weight, the adhesion of the formed pixels 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 fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol, polyethylene glycol monoalkyl ethers and poly (fluoroalkyl acrylate); vinyl trimethoxysilane and vinyl triethoxysilane , Vinyl tris (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)
Adhesion promoters such as ethyltrimethoxysilane, 3-chloropropylmethyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, and 3-mercaptopropyltrimethoxysilane; 2,2-thiobis (4 Antioxidants such as -methyl-6-t-butylphenol) and 2,6-di-t-butylphenol; 2- (3-t-butyl-5-methyl-
UV absorbers such as 2-hydroxyphenyl) -5-chlorobenzotriazole and alkoxybenzophenones;
Aggregation inhibitors such as sodium polyacrylate; 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 may contain other additives as the case may be. 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 viewpoints of pigment dispersibility and coatability, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, cyclohexanone, 2-heptanone, 3-heptanone, 2- Ethyl hydroxypropionate, 3-methyl-3-methoxybutyl propionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, n-butyl acetate, i-butyl acetate, formic acid Preferred are n-amyl, i-amyl acetate, n-butyl propionate, i-propyl butyrate, ethyl butyrate, n-butyl butyrate, ethyl pyruvate and the like. 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 use ratio of the solvent is not particularly limited, but from the viewpoint of the applicability and stability of the obtained radiation-sensitive composition, the total concentration of components excluding the solvent in the composition is usually, A ratio of 5 to 50% by weight, preferably 10 to 40% by weight is desirable.

[0040]

DETAILED DESCRIPTION OF THE INVENTION The radiation-sensitive composition for a color filter of the present invention comprises (A) an organic pigment, (B) an alkali-soluble resin, (C) a polyfunctional monomer, and (D) a photopolymerization initiator. Is contained as an essential component, and particularly preferred examples of the composition include the following (a) to (g). (A) (A) The organic pigments are CI Pigment Violet 19, CI Pigment Red 122, CI Pigment Red 202, CI Pigment Red 206, CI Pigment Red 207 and CI Pigment Red 209.
A radiation-sensitive composition for a color filter, comprising at least one member selected from the group consisting of: (B) A radiation-sensitive composition for a color filter, wherein (A) the organic pigment further contains 20% by weight or less of a yellow organic pigment of the total pigment component. (C) The above (A) or (B) wherein (B) the alkali-soluble resin contains a carboxyl group-containing copolymer (I).
Radiation-sensitive composition for color filters. (D) When the (D) photopolymerization initiator is 2,2′-bis (2-
Chlorophenyl) -4,4 ′, 5,5′-tetrakis (4-ethoxycarbonylphenyl) biimidazole,
2,2′-bis (2-chlorophenyl) -4,4 ′,
5,5′──tetraphenylbiimidazole, 2,2 ′
-Bis (2-bromophenyl) -4,4 ', 5,5'-
Tetrakis (4-ethoxycarbonylphenyl) biimidazole, 2,2′-bis (2,4-dichlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (2,4 -Dibromophenyl)-
4,4 ′, 5,5′-tetraphenylbiimidazole,
2,2'-bis (2,4,6-trichlorophenyl)-
From the group of 4,4 ', 5,5'-tetraphenylbiimidazole and 2,2'-bis (2,4,6-tribromophenyl) -4,4', 5,5'-tetraphenylbiimidazole The radiation-sensitive composition for a color filter according to the above (A), (B) or (C), comprising one or more selected biimidazole compounds. (E) The photopolymerization initiator of (D), (B), (C) or (D), wherein the photopolymerization initiator further contains at least one member selected from the group consisting of a benzophenone-based compound and a thiazole-based curing accelerator. Radiation-sensitive composition for color filters. (F) (B) the carboxyl group-containing copolymer (I) is
(Meth) acrylic acid / methyl (meth) acrylate copolymer, (meth) acrylic acid / 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 Coalescing,
Methacrylic acid / styrene / benzyl methacrylate / N
-Phenylmaleimide copolymer, methacrylic acid / 2-acryloyloxyethyl succinic acid / styrene / benzyl methacrylate / N-phenylmaleimide copolymer, methacrylic acid / 2-acryloyloxyethyl succinic acid / styrene / allyl methacrylate / N -The radiation-sensitive composition for a color filter according to the above (a), (b), (c), (d) or (e), comprising at least one member selected from the group of phenylmaleimide copolymers. (G) (C) The polyfunctional monomer is at least one selected from the group consisting of trimethylolpropane triacrylate, pentaerythritol triacrylate and dipentaerythritol hexaacrylate, (A), (B) and (C) above. , (D), (e) or (f)
Radiation-sensitive composition for color filters.

[0041]

EXAMPLES Hereinafter, embodiments of the present invention will be described more specifically with reference to examples of the present invention, but the present invention is not limited to these examples. Example 1 (A) CI Pigment Red 122 as an organic pigment,
(B) Methacrylic acid / benzyl methacrylate / 2-hydroxyethyl methacrylate copolymer (copolymer weight ratio = 15/75/15, Mw =
28,000) 60 parts by weight, (C) 40 parts by weight of dipentaerythritol hexaacrylate as a polyfunctional monomer, and (D) 2,2′-bis (2-chlorophenyl) -4,4 as a photopolymerization initiator. ', 5,5''Tetraphenylbiimidazole (10 parts by weight), 4,4'-bis (diethylamino) benzophenone (10 parts by weight), and a solvent, ethyl 3-ethoxypropionate (1000 parts by weight), were mixed. A liquid composition of the composition was prepared. This liquid composition is referred to as composition (R1).

Reference Example 1 A liquid composition of a radiation-sensitive composition was prepared in the same manner as in Example 1 except that CI Pigment Yellow 110 / CI Pigment Yellow 83 was used instead of CI Pigment Red 122. This liquid composition was treated with the composition (Y
1).

Reference Example 2 The liquid composition of the radiation-sensitive composition was the same as in Example 1 except that a cyan pigment (CI Pigment Blue 15: 4 / CI Pigment Green 36) was used instead of CI Pigment Red 122. Was prepared. This liquid composition is referred to as composition (C1).

[Preparation of Color Filter] The composition (R
1) Using the composition (Y1) and the composition (C1), a color filter was produced by forming each pixel array of red, yellow, and cyan on a transparent substrate as follows. First, the composition (R1) 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 applied in a clean oven at 80 ° C. Pre-baking was performed for 10 minutes 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, was exposed at an exposure amount of 200 mJ / cm ² ultraviolet including each wavelength of 405nm and 436 nm. 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,
Perform post-baking for 0 minutes, and place 20 μm × 2 on the substrate.
A pixel array on which a red pixel pattern having a size of 0 μm was formed. Thereafter, the composition (Y1) and the composition (C) were applied to the substrate on which the red pixel array was formed.
Using 1), the process of forming the red pixel array is repeated, and a pixel array in which a yellow pixel pattern of 20 μm × 20 μm is arranged and a cyan pixel pattern of 20 μm × 20 μm are arranged. By sequentially forming the pixel arrays, a subtractive color mixture type color filter in which red, yellow, and cyan pixel arrays were stacked in three layers was produced.

[Evaluation of Color Filter] The color filter was evaluated as follows. Chromaticity (I) of the color filter immediately after heat resistance and chromaticity (II) after heating the color filter at 250 ° C. for 1 hour.
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 the chromaticity (II) and the chromaticity (I). As a result, ΔEab was 1.26. Light resistance The color filter produced in the same manner as above was irradiated with light using an ultraviolet long life fade meter (manufactured by Suga Test Instruments Co., Ltd.), and the chromaticity 90 hours after irradiation was measured using a microanalyzer (Tokyo Denshoku). (“TC-1800M” manufactured by Co., Ltd.)
The light fastness was evaluated by the color difference (ΔEab) between the chromaticity and the chromaticity (I) of the color filter immediately after production. As a result, ΔEab was 1.95. White Balance For the color filter produced in the same manner as described above, the formation process of the red pixel pattern was repeated using the composition (Y1) or the composition (C1) to obtain 20 μm × 20
A pixel array having a yellow pixel pattern having a size of μm or a pixel array having a cyan pixel pattern having a size of 20 μm × 20 μm is overlaid, and then a microanalyzer (Tokyo Denshoku Co., Ltd.) "TC-1
800M ”), the spectral transmittance of each color filter was measured, and the white balance was simulated. The result is shown in FIG.

Comparative Example 1 As an organic pigment, CI Pigment Red 122 was used in place of CI Pigment Red 122.
Example 1 except that CI Pigment Red 254 was used.
In the same manner as in the above, a liquid composition of a radiation-sensitive composition in which a red pigment was dispersed was prepared. This liquid composition is referred to as composition (r1). This composition (r1) and composition (Y1)
And a composition (C1), a color filter was produced in the same manner as described above, and then evaluated in the same manner as above. As a result, the heat resistance Δ
Eab was 1.54 and ΔEab of light resistance was 2.15.
FIG. 2 shows a simulation result of the white balance of the color filter.

[0047]

The radiation-sensitive composition for a color filter of the present invention is excellent in heat resistance and light resistance, has an excellent white balance, and is a subtractive color mixture type used in a reflection type color liquid crystal display device. It can be used very suitably for the production of color filters.

[Brief description of the drawings]

FIG. 1 is a diagram illustrating a simulation result of a white balance of a color filter produced using the radiation-sensitive composition for a color filter of the present invention.

FIG. 2 is a diagram illustrating a simulation result of white balance of a color filter prepared using a radiation-sensitive composition for a color filter for comparison.

Claims (2)

[Claims] 1. An organic pigment containing (A) a quinacridone pigment represented by the following structural formula (1), (B) an alkali-soluble resin, (C) a polyfunctional monomer, and (D) photopolymerization initiation. A radiation-sensitive composition for a color filter of a subtractive color mixture type characterized by containing an agent. 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. [Chemical formula 2] 2. The radiation-sensitive composition for a color filter according to claim 1, wherein the organic pigment (A) further contains 20% by weight or less of a yellow organic pigment based on all pigment components.