JP2001051112A - Photosensitive coloring composition for color filter and color filter using it - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a coloring composition for a color filter using a pigment, excellent in heat resistance and in light resistance, having color purity equal to or higher than that of a color filter by a dyeing method, by containing a specific pigment dispersant. SOLUTION: This photosensitive coloring composition for a color filter includes a monomer and/or a photosensitive resin, a pigment and a pigment dispersant shown by a formula I. In the formula I, DPP shows a residue of diketopyrrolo pyrrole, and R1-R5 show independently a hydrogen atom, a halogen atom or the like respectively. At least, one of R1-R5 is a bonding hand of E. (m) shows an integer of 1-2, and (p) shows an integer of 1-4. E shows a formula II or a formula III. In the formulas II, III, X shows a direct bond, -SO2NH- or the like, and Z shows -SO2-, -CO- or the like. (n) shows an integer of 1-20. R16 and R17 show a saturated or unsaturated alkyl group or the like, and R18-R21 show independently a hydrogen atom or the like respectively. R22 shows a saturated or unsaturated aryl group or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a coloring composition used for producing a color filter used in a color liquid crystal display device, a video camera, and the like, and a color filter using the coloring composition.

[0002]

2. Description of the Related Art A color filter is one in which two or more types of fine bands (stripe) of different hues are arranged in parallel or intersecting on the surface of a transparent substrate such as glass or the like, and fine pixels are arranged in a constant vertical and horizontal direction. It consists of those arranged in. Since the pixel size is as fine as several tens to several hundreds of μm and is arranged in a predetermined arrangement for each hue, various methods have been conventionally proposed for producing color filters. Conventionally, a color filter is required to have high transparency, and thus has been manufactured by a method of coloring using a dye, which is generally called a dyeing method. For example, a photosensitive material to be dyed is applied to a substrate such as glass, followed by pattern exposure of one filter color, and then the unexposed portion is removed in a developing step, and the remaining pattern portion is removed by the filter color. It was manufactured by sequentially repeating the operation of dyeing with a dye for all filter colors.

A transparent electrode for driving a liquid crystal is generally formed on a color filter used in a color liquid crystal display device by vapor deposition or sputtering, and an alignment film for aligning the liquid crystal in a certain direction is further formed thereon. Are formed. In order to sufficiently obtain the performance of these transparent electrodes and alignment films, their formation is generally performed at 200 ° C.
As described above, it is necessary to carry out at a high temperature of preferably 250 ° C. or higher.

A color filter using a dye is excellent in transparency, but inferior in heat resistance. Therefore, formation of a transparent electrode and an alignment film on the color filter is required.
It must be performed at a temperature lower than ℃, the performance of the transparent electrode and the alignment film was inferior, and the display performance was limited. In addition, color filters using dyes have poor light fastness and are not suitable for use outdoors. Therefore, instead of dyes, pigments having excellent light resistance and heat resistance have come to be used, and most of currently manufactured color filters use organic pigments.

[0005]

However, color filters using pigments are generally inferior in transparency and color purity to those using dyes, and improvements have been strongly desired. The present invention provides a coloring composition and a color filter which are excellent in heat resistance and light resistance and have a color purity equal to or higher than that of a color filter manufactured by a dyeing method, and which are used for manufacturing a color filter using a pigment. Aim.

[0006]

SUMMARY OF THE INVENTION The present invention relates to a photosensitive coloring composition for a color filter, comprising a monomer and / or a photosensitive resin, a pigment, and a pigment dispersant represented by the following formula (1). . In addition, the present invention relates to a color filter comprising a transparent substrate and a color material layer formed on the transparent substrate using the photosensitive coloring composition. Equation (1)

Embedded image (However, DPP represents a diketopyrrolopyrrole residue represented by the following formula (2). Formula (2)

Embedded image

E represents the following equation (3) or the following equation (4). Equation (3)

Embedded image Equation (4)

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R _{1 to} R ₁₅ each independently represent a hydrogen atom,
Halogen atom, or alkyl, alkoxy, cyano,
R represents a sulfonyl, carboxyl, dialkylamino, halogenoalkyl, alkoxycarbonyl, alkylmercapto, carbamoyl, or sulfamoyl group;
₁ at least one of to R ₁₅ is a bond of E, R ₆ ~
_At least one of R ₁₅ is

Embedded image Is a bond.

M: represents an integer of 1 to 2. p: represents an integer of 1 to 4. X: direct bond, -SO_TwoNH-, -CONH-, -CH
_TwoNHCOCH_TwoNH- or-(CH_Two) QNH-
(Where q represents an integer of 1 to 10). n: represents an integer of 1 to 20. However, if X is a direct bond
In the case, it represents an integer of 1 to 10. R₁₆, R₁₇: Each independently may be substituted
A sum or unsaturated alkyl group, or R₁₆, R₁₇In
May be substituted containing an oxygen, oxygen or sulfur atom
Represents a heterocyclic ring. Z: -SO_Two-, -CO-, -CH_TwoNHCOCH
_Two-,-(CH_Two) Q-, -SO_TwoNH-, -CONH
-, -CH_TwoNHCOCH_TwoNH- or-(C
H _Two) Represents qNH- (where q is an integer of 1 to 10)
Represent. ). R₁₈, R₁₉, R₂₀, R_{twenty one}: Each independently a hydrogen atom,
Optionally substituted saturated or unsaturated alkyl
Represents a group or an aryl group. R_{twenty two}: Saturated or unsaturated alkyl which may be substituted
Represents a kill group or an aryl group.

The above-mentioned pigment dispersant functions to prevent the aggregation of the pigment in the photosensitive coloring composition and to maintain the finely dispersed state of the pigment, and to provide a color filter having high transmittance and high color purity. Important for manufacturing.
The specific structure of the pigment dispersant is shown below. Note that the number, position, and the like of the substituents vary depending on the reaction conditions.

Embedded image

[0011]

Embedded image

[0012]

Embedded image

Pigment dispersant (11)

Embedded image

An outline of a typical method for producing the above-mentioned pigment dispersant is shown below by taking pigment dispersant (11) as an example. First,
A compound represented by the formula (5) is produced by a conventional method. Equation (5)

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Next, the compound represented by the formula (5) is chlorosulfonated by a conventional method to produce a compound represented by the formula (6). The pigment dispersant (11) is produced by reacting piperazine. Equation (6)

Embedded image

In E, the amine component used to form the substituent represented by the formula (3) includes, for example,
Dimethylamine, diethylamine, N-ethylisopropylamine, N-methylbutylamine, N-methylisobutylamine, N-butylethylamine, N-tert-butylethylamine, diisopropylamine, dipropylamine, N-sec-butylpropylamine, Butylamine, di-sec-butylamine, diisobutylamine,
N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-
Ethylhexyl) amine, dioctylamine, N-methyloctadecylamine, didecylamine, diallylamine, N-ethyl-1,2-dimethylpropylamine, N
-Methylhexylamine, 2-hydroxymethylaminomethanol, dioleylamine, distearylamine,
N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminopropylamine, N, N-dimethylaminoamylamine,
N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N
-Diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutylaminopropylamine, N, N
-Dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N-methyl-laurylaminopropylamine, N, N-ethyl-hexylaminoethylamine,
N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine and the like can be mentioned.

In E, the amine component used for forming the substituent represented by the formula (4) includes, for example, piperidine, 2-pipecholine, 3-pipecholine,
4-Pipecoline, 2,4-Lupetidine, 2,6-Lupetidine, 3,5-Lupetidine, 3-Piperidinemethanol, Pipecolic acid, Isonipecotic acid, Methyl isonicopetinate, Ethyl isonicopetinate, 2-Piperidineethanol, Pyrrolidine, 3- Hydroxypyrrolidine, N
-Aminoethylpiperidine, N-aminoethyl-4-pipecholine, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecholine, N-aminopropyl-4-pipecholine, N-aminopropylmorpholine , N-methylpiperazine, N-butylpiperazine, N-tylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine and the like.

Since the above-mentioned pigment dispersant exerts an excellent dispersing effect on almost all pigments, a coloring material for a color filter is prepared using the photosensitive coloring composition of the present invention obtained by dispersing a pigment with the above-mentioned pigment dispersant. When a layer is formed, the color purity of the color material layer is higher than that of a conventional color material layer. In particular, diketopyrrolopyrrole-based pigments are extremely difficult to disperse, and thus could not be conventionally used in a photosensitive coloring composition for producing a color filter. It can be used for a photosensitive coloring composition for production. Diketopyrrolopyrrole pigments are excellent as pigments constituting the color material layer of the color filter in terms of heat resistance, chemical resistance, and vivid color development, and the color purity using the diketopyrrolopyrrole pigment is high. It is significant that high color filters can be obtained.

Examples of the pigment other than the diketopyrrolopyrrole pigment used in the photosensitive coloring composition of the present invention include azo pigments such as soluble and insoluble azo pigments and condensed azo pigments, phthalocyanine pigments, and quinacridone pigments. ,
Isoindolinone pigments, isoindoline pigments, quinophthalone pigments, perylene / perinone pigments, dioxazine pigments, anthraquinone pigments, dianthraquinonyl pigments, anthrapyrimidine pigments, anthanthrone pigments, indanthrone pigments Organic pigments such as pigments, flavanthrone pigments, pyranthrone pigments, vat dye pigments, and basic dye pigments.

The pigment dispersant is preferably added in a proportion of 2 to 40 parts by weight, particularly 5 to 20 parts by weight, based on 100 parts by weight of the pigment. If the amount of the pigment dispersant is less than 2 parts by weight, the dispersing effect becomes insufficient. If the amount is more than 40 parts by weight, the excess pigment dispersant may adversely affect the dispersion.

The monomer used in the photosensitive coloring composition of the present invention is a compound whose polymerization is induced by a radical, and is a compound having at least one ethylenically unsaturated double bond (hereinafter referred to as "ethylenically unsaturated compound"). Is preferably used. The ethylenically unsaturated compound may be either a monomer or a low polymer having an ethylenically unsaturated double bond in a side chain or a main chain. Examples of the monomer include (meth) acrylic acid, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, (meth) acrylate, and vinyl compound. Further, the low polymer having an ethylenically unsaturated double bond is a polymer having a weight average molecular weight of less than 1000, and specifically, epoxy (meth) acrylate, urethane (meth) acrylate, polyester (meth) acrylate, and the like. Is mentioned.

Specific examples of the (meth) acrylate include 2-hydroxyethyl (meth) acrylate, 2
-Hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, polyethylene glycol di (meth) acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, dipenta Hexa (meth) acrylate which is a caprolactone adduct of erythritol hexa (meth) acrylate is exemplified. Further, specific examples of the vinyl compound include styrene, divinylbenzene, vinyl acetate, and vinyl acetate.

The photosensitive resin used in the photosensitive coloring composition of the present invention is a resin which is crosslinked by radicals, and has a weight average molecular weight of at least one ethylenically unsaturated double bond of from 1,000 to 500,000, more preferably 5000-1
100,000 resins are preferably used. As photosensitive resin,
(Meth) acrylic compound, linear polymer having a reactive functional group such as a hydroxyl group, a carboxyl group, or an amino group via an isocyanate group, an aldehyde group, an epoxy group, or the like which can react with the reactive functional group. A resin into which an ethylenically unsaturated double bond is introduced by reacting with an acid or the like is used. Also used is a half ester of a (meth) acrylic compound having a hydroxyl group such as a hydroxyalkyl (meth) acrylate of a linear polymer containing an acid anhydride such as a styrene maleic anhydride copolymer or an α-olefin maleic anhydride copolymer. Can be

The photosensitive coloring composition of the present invention preferably contains an alkylene oxide polymer for the purpose of further improving the function of the pigment dispersant.
The alkylene oxide polymer is a polymer containing an ethylene oxide and / or propylene oxide unit in a molecule, and has a surface property of a pigment and / or a pigment dispersant due to amphiphilic property caused by a hydrophilic group and a hydrophobic group. By adsorbing on the pigment, the dispersion stability of the pigment in the obtained photosensitive coloring composition is improved, and the flow characteristics of the obtained photosensitive coloring composition are improved.

The alkylene oxide polymer has a weight average molecular weight of 1,000 to 100,000, especially 1,000 to 50.
000 is preferred. If the weight average molecular weight of the alkylene oxide polymer is less than 1,000, sufficient orientation and adsorption effects cannot be obtained, and the contribution to dispersion stability is small. On the other hand, if it exceeds 100,000, steric hindrance of the alkylene oxide polymer molecules and interaction between the molecules become too large, and the viscosity of the oriented coloring composition becomes too high, which is not preferable.

When forming a color filter pattern by alkali development, the photosensitive coloring composition of the present invention preferably contains an alkali-soluble non-photosensitive resin. The alkali-soluble non-photosensitive resin is a resin that is dissolved in an alkaline aqueous solution and is not crosslinked by radicals, for example, a carboxyl group, a weight average molecular weight having an acidic functional group such as a sulfone group of 1,000 to 500,000,
Preferably, 5,000 to 100,000 resins are used. Specific examples of the alkali-soluble non-photosensitive resin include acrylic resin, α-olefin / (anhydride) maleic acid copolymer, styrene / (anhydride) maleic acid copolymer, styrene / styrene sulfonic acid copolymer, Ethylene / (meth)
Acrylic acid copolymer, isobutylene / (anhydrous) maleic acid copolymer, and the like can be mentioned. Among them, acrylic resin, α-olefin / (maleic anhydride) maleic acid copolymer, styrene / (maleic anhydride) maleic acid copolymer and styrene /
At least one selected from styrene sulfonic acid copolymers
Kinds of resins, particularly acrylic resins, are preferably used because of their high heat resistance and high transparency.

Further, the photosensitive coloring composition of the present invention includes:
When the composition is cured by ultraviolet light, a photoinitiator is contained. As the photoinitiator, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropane-
Acetophenone photoinitiators such as 1-one, 1-hydroxycyclohexylphenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin Benzoin-based, benzophenone-based photoinitiators such as ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4 ' Benzophenone photoinitiators such as -methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone,
Methylthioxanthone, isopropylthioxanthone,
Thioxanthone-based photoinitiators such as 2,4-diisopropylthioxanthone, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p -Methoxyphenyl)
-4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-pipenyl-4,6-bis (trichloromethyl) -S-triazine, 2,4-bis (trichloromethyl) -6-styryl s-triazine,
2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl)-
triazine photoinitiators and carbazole photoinitiators such as s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, A compound such as an imidazole-based photoinitiator is used.

The above photoinitiators may be used alone or as a mixture of two or more. As sensitizers, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrene Quinone, camphorquinone, ethylanthraquinone,
4,4′-diethylisophthalophenone, 3,3 ′,
4,4'-tetra (t-butylperoxycarbonyl)
Compounds such as benzophenone and 4,4'-diethylaminobenzophenone can also be used. Further, in the photosensitive coloring composition of the present invention, in order to sufficiently disperse the pigment,
In addition, water or an organic solvent may be used in order to apply the film uniformly and thinly on the transparent substrate. The organic solvents can be used alone or as a mixture.

The photosensitive coloring composition of the present invention can be produced, for example, by the following method. 1. A pigment and a pigment composition obtained by previously mixing a pigment and a pigment dispersant are added to a monomer and / or a photosensitive resin or an organic solvent solution or an aqueous solution thereof, and dispersed. 2. A pigment and a pigment dispersant are separately added and dispersed in a monomer and / or a photosensitive resin or an organic solvent solution or an aqueous solution thereof. 3. A pigment and a pigment dispersant are separately dispersed in a monomer and / or a photosensitive resin or an organic solvent solution or an aqueous solution thereof, and then mixed. In this case, the pigment dispersant may be dispersed only with the solvent. 4. After dispersing the pigment in the monomer and / or photosensitive resin or its organic solvent solution or aqueous solution, a pigment dispersant is added.

Monomers of pigments and pigment dispersants and / or
Alternatively, the photosensitive resin or its dispersion in an organic solvent solution or aqueous solution can be performed using various dispersing devices such as a three-roll mill, a two-roll mill, a sand mill, a kneader, a dissolver, a high-speed mixer, a homomixer, and an attritor. it can. Further, at the time of dispersion, various surfactants can be added in order to perform the dispersion well. In the method (1), even if the pigment composition is prepared by simply mixing the pigment powder and the pigment dispersant powder, the desired effect can be sufficiently obtained. However, a solution containing a pigment dispersant is added to a dispersion obtained by dispersing a pigment in water or an organic solvent, or mechanically mixed by various pulverizers such as a kneader, a roll, an attritor, and a super mill. A better mixing method such as adsorbing the pigment dispersant on the solvent or co-precipitating the pigment and the pigment dispersant in a solvent having a strong dissolving power such as sulfuric acid and coprecipitating with a poor solvent such as water is preferred. The result can be obtained.

The photosensitive coloring composition of the present invention can be obtained by centrifugation,
5μm by means such as sintering filter, membrane filter
The above coarse particles, preferably 1 μm or more coarse particles, more preferably 0.5 μm or more coarse particles and mixed dust are removed. The production of a color filter using the photosensitive coloring composition of the present invention is performed by uniformly applying the photosensitive coloring composition of the present invention on a transparent substrate, and then applying an active energy ray such as an ultraviolet ray or an electron beam through a photomask. Is performed by a method called so-called photolithography, in which a pattern is exposed and an unexposed portion is washed away with a solvent or an aqueous alkali solution to obtain a desired pattern. The photosensitive coloring composition of the present invention is applied on a transparent substrate by an application method such as spray coating, spin coating, or roll coating. As the transparent substrate, a glass plate or a resin plate of polycarbonate, polymethyl methacrylate, polyethylene phthalate, or the like is used.

Solvents are rarely used for development due to environmental problems, and alkali development is now mainstream. As the alkali developer, an aqueous solution such as sodium carbonate or caustic soda is used, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added. In order to increase exposure sensitivity, the photosensitive coloring composition of the present invention is applied and dried, and then a water-soluble or alkali-water-soluble resin,
For example, exposure can be performed after coating and drying a polyvinyl alcohol or a water-soluble acrylic resin to form a film for preventing polymerization inhibition by oxygen.

[0033]

The present invention will be described in more detail with reference to the following examples. In the following, “parts” means “parts by weight”. Prior to the examples, the synthesis of the acrylic resin used as the alkali-soluble non-photosensitive resin in the examples will be described.

(Synthesis of Acrylic Resin) A reaction vessel is charged with 800 parts of cyclohexanone, heated to 100 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator is added at the same temperature for 1 hour. The polymerization reaction was performed by dropping. 60.0 parts of styrene 60.0 parts of methacrylic acid 65.0 parts of methyl methacrylate 65.0 parts of butyl methacrylate 10.0 parts of azobisisobutyronitrile 10.0 parts After dropping, the mixture was further reacted at 100 ° C. for 3 hours, and then reacted with azobis. A solution prepared by dissolving 2.0 parts of isobutyronitrile in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour to synthesize a resin solution. After cooling to room temperature,
About 2 g of the resin solution was sampled, dried by heating at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20% to prepare an acrylic resin solution. . When the molecular weight of the obtained acrylic resin was measured by GPC, the weight average molecular weight was 40,000.

Example 1 A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali-developable photosensitive coloring composition. Diketopyrrolopyrrole pigment 4.5 parts (“Chromophthal DPP Red BP” manufactured by Ciba Specialty Co.) Pigment dispersant (1) 0.5 part The acrylic resin solution 24.0 parts Trimethylolpropane triacrylate 5.4 parts ( "NK ester ATMPT" manufactured by Shin-Nakamura Chemical Co., Ltd.) Photoinitiator ("Irgacure 907" manufactured by Ciba-Geigy) 0.3 part Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 part Cyclohexanone 65.1 Department

Example 2 A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali-developable photosensitive coloring composition. Diketopyrrolopyrrole pigment 4.0 parts ("Chromophthal DPP Red BP" manufactured by Ciba Specialty Co.) Pigment dispersant (2) 1.0 part Polyoxyalkyleneamine 1.0 part (Texaco Chemical Company "Jeffamine M" -3000 ", weight average molecular weight 3000) Above acrylic resin solution 24.0 parts Trimethylolpropane triacrylate 5.4 parts (" NK ester ATMPT "manufactured by Shin-Nakamura Chemical Co., Ltd.) Photoinitiator (" Irgacure "manufactured by Ciba Geigy) 907 ") 0.3 parts Sensitizer (" EAB-F "manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 64.1 parts

Example 3 A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali-developable photosensitive coloring composition. 4.5 parts of anthraquinone pigment (“Chromophthal Red A2B” manufactured by Ciba Specialty) 0.5 parts of pigment dispersant (2) 1.0 part of polyoxyalkyleneamine (“Jeffamine M-3000” manufactured by Texaco Chemical Company) , Weight average molecular weight 3000) The above acrylic resin solution 24.0 parts Dipentaerythritol hexaacrylate 5.4 parts ("Aronix M-400" manufactured by Toagosei Co., Ltd.) Photoinitiator ("Irgacure 907" manufactured by Ciba Geigy) 0.3 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 parts Cyclohexanone 65.1 parts

Example 4 A mixture having the following composition was uniformly stirred and mixed, and then filtered through a 1 μm filter to prepare an alkali-developable photosensitive coloring composition. Diketopyrrolopyrrole-based pigment 4.5 parts ("Chromophthal DPP Red BP" manufactured by Ciba Specialty Co.) Pigment dispersant (3) 0.5 part Polyoxyalkyleneamine 1.0 part (Texaco Chemical Company "Jeffamine M" -1000 ", weight average molecular weight 1000) Above acrylic resin solution 20.0 parts Photosensitive resin 4.0 parts (Daicel Co., Ltd." Cyclomer P ACA200 ", weight average molecular weight 13200) Dipentaerythritol hexaacrylate 5.4 Part ("DPHA" manufactured by Nippon Kayaku Co., Ltd.) Photoinitiator ("Irgacure 907" manufactured by Ciba Geigy) 0.3 part Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.2 part Cyclohexanone 64.1 Department

Comparative Example 1 An alkaline development type photosensitive coloring composition was prepared in the same manner as in Example 1 except that the pigment dispersant (1) was omitted. Comparative Example 2 An alkali-developable photosensitive coloring composition was prepared in the same manner as in Example 2 except that the pigment dispersant (2) was omitted. Comparative Example 3 An alkali-developable photosensitive coloring composition was prepared in the same manner as in Example 3 except that the pigment dispersant (2) was changed to a glycerin fatty acid ester (“Ajispar PN411” manufactured by Ajinomoto Co.).

Using the photosensitive coloring compositions obtained in Examples and Comparative Examples, a coloring material layer was formed on a transparent substrate by the following method, and the chromaticity was measured. 100 mm x 100 mm;
The obtained photosensitive coloring composition was coated on a glass substrate having a thickness of 1 mm using a spin coater at 500 rpm and 1000 rpm.
m, 1500 rpm, and 2000 rpm to obtain four types of coated substrates having different color material layer thicknesses. Next, after drying at 70 ° C. for 20 minutes, ultraviolet exposure was performed using an ultra-high pressure mercury lamp with an integrated light amount of 150 mJ. After exposure, the film was heated at 200 ° C. for 1 hour and allowed to cool, and then C was detected using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.).
The chromaticity (Y, x, y) at the light source was measured. X and y when the Y value is 20.0 are determined from the four sets of chromaticity measurement results,
Further, the dominant wavelength and the color stimulus purity at this time were determined from the xy chromaticity diagram of the CIE color system. Table 1 shows the results.

Table 1 Example Yxy Dominant Wavelength Color Stimulation Purity (----) nm) (%)-----------------------------Example 1 20 0.646 0.339 608.2 96.0 Example 2 20 0.647 0.340 608.1 96.4 Example 3 20 0.541 0.281 -494.0 59.2 Example 4 20 0.646 0.340 608 .1 96.2 Comparative Example 1 20 0.574 0.300 637.0 64.7 Comparative Example 2 20 0.601 0.310 622.4 75.0 Comparative Example 3 20 0.505 0.277 -495. 354.5

The coloring material layers formed using the photosensitive coloring compositions of Examples 1 to 4 containing the pigment dispersant represented by the formula (1) have a good dispersion state of the pigment. The main wavelength is small and the color purity is high. It is known that the better the dispersion state of the diketopyrrolopyrrole-based pigment is, the more the hue becomes bluish, that is, the smaller the main wavelength is, and the smaller the main wavelength is, the more the dispersibility is improved. Further, the coloring material layers formed using the photosensitive coloring compositions of Examples 2 and 4 containing the alkylene oxide polymer were prepared using the photosensitive coloring composition of Example 1 containing no alkylene oxide polymer. The color stimulus purity is further higher than that of the formed color material layer. Further, the coloring material layer formed using the photosensitive coloring composition of Examples 1, 2 and 4 containing the diketopyrrolopyrrole-based pigment was the photosensitive coloring composition of Example 3 containing the anthraquinone-based pigment. The effect of improving the color stimulus purity is higher than that of the color material layer formed by using the pigment, and the diketopyrrolopyrrole-based pigment is extremely dispersed by using the pigment dispersant represented by the formula (1). It is shown that a color material layer having high color purity can be formed.

On the other hand, Comparative Examples 1 and 2, which contain a diketopyrrolopyrrole pigment and do not contain the pigment dispersant represented by the formula (1), have a large dominant wavelength and low color stimulus purity. Also,
In Comparative Example 2, which does not contain the pigment dispersant represented by the formula (1) but contains the alkylene oxide polymer, the dominant wavelength is smaller and the color stimulation purity is lower than Comparative Example 1 which does not contain the alkylene oxide polymer. Although it is slightly higher,
It is far from Example 1 containing the pigment dispersant represented by the formula (1). Further, in Example 3 containing an anthraquinone pigment and Comparative Example 3, Example 3 containing the pigment dispersant represented by the formula (1) has higher color stimulation purity at substantially the same dominant wavelength. It has been shown that a color material layer having high color purity can be formed by dispersing using a pigment dispersant represented by Formula (1).

[0044]

According to the present invention, a color filter having high color purity can be produced by using the photosensitive coloring composition of the present invention containing the diketopyrrolopyrrole derivative represented by the formula (1) as a pigment dispersant. Now you can. In particular, a color filter produced using the photosensitive coloring composition of the present invention in which a diketopyrrolopyrrole-based pigment is dispersed with a diketopyrrolopyrrole-based derivative represented by the formula (1) has extremely high color purity. High and very good for practical use.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C08L 71/02 C08L 71/02 101/16 G03F 7/004 505 G03F 7/004 505 C08L 101/00 (72 ) Inventor Jun Kanada F-term (reference) 2H025 AB13 AC01 AD01 BC43 CA04 CB14 CC12 CC20 2H048 BA45 BA47 BB14 BB41 4J002 AA031 BB083 BB093 BB173 BC011 BC031 BC043 BC123 BF021 BG011 BG031 BG071 BG131 BH023 CD201 CF271 CH022 CH051 EA067 ED088 EE038 EE057 EF098 EH128 EQ017 ET007 EU116 EU146 EU188 EU236 EU238 EV026 EV068 EV216 EV266 EV308 FD097 FD148 GH01 GP00 HA05

Claims (6)

[Claims] A face and a monomer and / or a photosensitive resin.
And a pigment dispersant represented by the following formula (1).
Photosensitive coloring composition for color filters. Formula (1)(However, DPP is a diketopyro represented by the following formula (2).
Represents a ropyrrole residue. Formula (2)E represents the following formula (3) or the following formula (4). Formula (3)Formula (4)R₁~ R_Fifteen: Independently, hydrogen atom, halogen atom
Or alkyl, alkoxy, cyano, sulfoni
, Carboxyl, dialkylamino, halogenoalkyl
, Alkoxycarbonyl, alkyl mercapto, cal
Represents a bamoyl or sulfamoyl group;₁~ R_Fifteen
At least one is a bond of E, and R₆~ R_FifteenLittle
At least one isIs a bond. m: represents an integer of 1 to 2. p: represents an integer of 1 to 4. X: direct bond, -SO_TwoNH-, -CONH-, -CH
_TwoNHCOCH_TwoNH- or-(CH_Two) QNH-
(Where q represents an integer of 1 to 10). n: represents an integer of 1 to 20. However, if X is a direct bond
In the case, it represents an integer of 1 to 10. R₁₆, R₁₇: Each independently may be substituted
A sum or unsaturated alkyl group, or R₁₆, R₁₇In
May be substituted containing an oxygen, oxygen or sulfur atom
Represents a heterocyclic ring. Z: -SO_Two-, -CO-, -CH_TwoNHCOCH
_Two-,-(CH_Two) Q-, -SO_TwoNH-, -CONH
-, -CH_TwoNHCOCH_TwoNH- or-(C
H _Two) Represents qNH- (where q is an integer of 1 to 10)
Represent. ). R₁₈, R₁₉, R₂₀, R_{twenty one}: Each independently a hydrogen atom,
Optionally substituted saturated or unsaturated alkyl
Represents a group or an aryl group. R_{twenty two}: Saturated or unsaturated alkyl which may be substituted
Represents a kill group or an aryl group. 2. The photosensitive coloring composition for a color filter according to claim 1, further comprising an alkylene oxide polymer. 3. The photosensitive coloring composition for a color filter according to claim 1, further comprising an alkali-soluble non-photosensitive resin. 4. An alkali-soluble non-photosensitive resin is an acrylic resin, an α-olefin / (anhydride) maleic acid copolymer,
The photosensitive coloring composition for a color filter according to claim 3, which is at least one resin selected from a styrene / (anhydride) maleic acid copolymer and a styrene / styrene sulfonic acid copolymer. 5. The photosensitive coloring composition for a color filter according to claim 1, wherein the pigment is a diketopyrrolopyrrole-based pigment. 6. A color filter comprising: a transparent substrate; and a color material layer formed on the transparent substrate by using the photosensitive coloring composition according to any one of claims 1 to 5.