JP2010277093A - Red colored composition for color filter, and color filter - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a colored composition for a color filter excellent in color characteristics, and to provide a color filter in a thin film state excellent in color characteristics. <P>SOLUTION: A red colored composition for a color filter is provided, which contains a pigment carrier comprising a transparent resin, a precursor thereof or a mixture of those, an anthraquinone pigment expressed by general formula (1) or (2), a diketopyrrolopyrrole pigment expressed by general formula (3), and an anthraquinone pigment derivative and a diketopyrrolopyrrole pigment derivative having a specific basic group. The color filter includes filter segments formed of the red colored composition. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

The present invention relates to a red coloring composition for a color filter used for manufacturing a color filter used for a color liquid crystal display device, a color image pickup tube element, and the like, and a color filter formed using the same.

In recent years, liquid crystal display devices have been applied to TV monitor applications. For color filters, the transmittance, that is, the lightness and color purity, coating uniformity when forming pixels, sensitivity, developability, pattern shape, etc. Demand levels for various characteristics are increasing. Among these, a bright color filter is required to produce a panel with low power consumption, and the required characteristic of improving brightness has been regarded as important.
In order to improve the color characteristics and brightness of the color filter, conventionally, a method of toning a red coloring composition with a red pigment and a yellow pigment has been employed. However, in addition to the above required characteristics, when trying to expand the color reproduction region of the color filter and reduce the film thickness, there is a limit to the color matching with one type of red pigment and one type of yellow pigment.

Japanese Patent Laid-Open No. 10-148712

The objective of this invention is providing the coloring composition for color filters excellent in the color characteristic, and the color filter excellent in a color characteristic, and a thin film.

式（２）

式（３）

（上記式（１）、（２）において、Ａは、それぞれ独立に、水素原子または置換基を有してもよいアルキル基もしくはアリール基を表す。上記式（３）において、Ｂは、それぞれ独立に、水素原子、置換されてもよい飽和もしくは不飽和のアルキル基、シアノ基、置換されてもよいアリール基、またはハロゲン原子を示す。）
式（４）

式（５）

式（６）

式（７）

（上記式（４）〜（７）において、Ｘは、−ＳＯ₂−、−ＣＯ−、−ＣＨ₂ＮＨＣＯＣＨ₂−、−ＣＨ₂−または直接結合を表し、ｎは、１〜１０の整数を表し、Ｒ₁およびＲ₂は、それぞれ独立に、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基もしくは置換されていてもよいフェニル基を表すか、またはＲ₁とＲ₂とが結合して更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を形成し、Ｒ₃は、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表し、Ｒ₄、Ｒ₅、Ｒ₆およびＲ₇は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表し、Ｙは、−ＮＲ₈−Ｚ−ＮＲ₉−または直接結合を表し、Ｒ₈およびＲ₉は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基または置換されていてもよいフェニル基を表し、Ｚは、炭素数１〜３６の置換されていてもよいアルキレン基、炭素数２〜３６の置換されていてもよいアルケニレン基、または置換されていてもよいフェニレン基を表し、Ｒは、式（８）で示される置換基、または式（９）で示される置換基を表し、Ｑは、水酸基、アルコキシル基、式（８）で示される置換基または式（９）で示される置換基を表す。）
式（８）

式（９）

また、本発明のカラーフィルタは、上記赤色着色組成物から形成されるフィルタセグメントを具備することを特徴とする。 The red coloring composition for a color filter of the present invention comprises a pigment carrier comprising a transparent resin, a precursor thereof or a mixture thereof, an anthraquinone pigment represented by the following general formula (1) or (2), and the following general formula: The diketopyrrolopyrrole pigment represented by (3), the basic group of the following formula (4), the basic group of the following formula (5), the basic group of the following formula (6), and the following formula (7) And an anthraquinone pigment derivative having at least one basic group selected from the group consisting of basic groups and a diketopyrrolopyrrole pigment derivative.
Formula (1)

Formula (2)

Formula (3)

(In the above formulas (1) and (2), A each independently represents a hydrogen atom or an alkyl group or aryl group which may have a substituent. In the above formula (3), B represents each independently. Represents a hydrogen atom, a saturated or unsaturated alkyl group which may be substituted, a cyano group, an aryl group which may be substituted, or a halogen atom.)
Formula (4)

Formula (5)

Formula (6)

Formula (7)

(In the above formulas (4) to (7), X represents —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ — or a direct bond, and n represents an integer of 1-10. R ₁ and R ₂ each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Represents a group, or R ₁ and R ₂ are combined to form an optionally substituted heterocycle containing an additional nitrogen, oxygen or sulfur atom, and R ₃ is substituted with 1 to 36 carbon atoms. Represents an optionally substituted alkyl group, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group, and R ₄ , R ₅ , R ₆ and R ₇ are each independently Hydrogen atom, optionally substituted alkyl having 1 to 36 carbon atoms Group, a optionally substituted alkenyl or optionally substituted phenyl group having 2 to 36 carbon atoms, Y is, -NR ₈ -Z-NR ₉ - or a direct bond, R ₈ and R ₉ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. , Z represents an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group, and R represents a formula Represents a substituent represented by (8) or a substituent represented by formula (9), and Q represents a hydroxyl group, an alkoxyl group, a substituent represented by formula (8) or a substituent represented by formula (9). To express.)
Formula (8)

Formula (9)

Moreover, the color filter of this invention comprises the filter segment formed from the said red coloring composition.

Since the red coloring composition for a color filter of the present invention contains two specific types of red pigment, an anthraquinone pigment derivative having a basic group, and a diketopyrrolopyrrole pigment derivative having a basic group, The characteristics are adjusted efficiently, and it is possible to reduce the thickness of the color filter by forming a red filter segment using the red coloring composition.

First, the red coloring composition for color filters of the present invention will be described.
The red coloring composition for a color filter of the present invention comprises a pigment carrier comprising a transparent resin, a precursor thereof, or a mixture thereof, an anthraquinone pigment represented by the general formula (1) or (2), and a general formula (3 ), A basic group of the following formula (4), a basic group of the following formula (5), a basic group of the following formula (6), and a base of the following formula (7) An anthraquinone pigment derivative having at least one basic group selected from the group consisting of a functional group and a diketopyrrolopyrrole pigment derivative are included. The reason for combining two specific red pigments is to effectively match the transmission spectrum of each pigment and to maximize performance. By combining two specific types of red pigments, the spectral spectrum transmission region is expanded, and at the same time, pigments of the same color are used, so that a color filter having a higher concentration as a red coloring composition and a thinner film than before can be obtained. it can.

Examples of the anthraquinone pigment represented by the general formula (1) or (2) include C.I. I. Pigment Red 89, 177 and the like, but C.I. I. Pigment Red 177 is preferred.
Examples of the diketopyrrolopyrrole pigment represented by the general formula (3) include C.I. I. Pigment Red 254, 264 and the like, but C.I. I. Pigment Red 254 is preferred.

The anthraquinone pigment represented by the general formula (1) or (2) and the diketopyrrolopyrrole pigment represented by the general formula (3) are preferably 1:99 to 40:60, more preferably, by weight ratio. It is contained in a ratio of 1:99 to 30:70. If the amount of the anthraquinone-based compound represented by the general formula (1) or (2) is larger than the above range, the brightness will not be sufficiently increased due to the spectral characteristics of the anthraquinone-based pigment. Due to the spectral characteristics of the ketopyrrolopyrrole pigment, yellowishness becomes strong, and deviation from the target chromaticity (x, y) becomes large.

The red coloring composition for color filters of the present invention includes C.I. I. Pigment Red 7, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 81: 4, 146, 184, 185, 187, 200, Red pigments such as 202, 208, 210, 246, 255, 270, 272, and 279; I. Orange pigments such as Pigment Orange 36, 43, 51, 55, 59, 61, 71, 73 can be used in combination.
For chromaticity toning, C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180 It can be used in combination with the yellow pigments such as 181,182,185,187,188,193,194,198,199,213,214.
In this case, the anthraquinone pigment of the present invention and the diketopyrrolopyrrole based on the total amount of the pigment (the total amount of the anthraquinone pigment, diketopyrrolopyrrole pigment, other red pigment, orange pigment and yellow pigment of the present invention). The content of the system pigment varies depending on the required color characteristics, but is preferably 60 to 100% by weight, particularly 90 to 99% by weight from the viewpoint of obtaining sufficient brightness.

The red coloring composition for a color filter of the present invention has titanium oxide, barium sulfate, zinc white, lead sulfate, yellow in order to ensure good coatability, sensitivity, developability, etc. while balancing saturation and lightness. Inorganic pigments such as lead, zinc yellow, red rose (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, chromium oxide green, cobalt green, amber, titanium black, synthetic iron black, carbon black can be included. .
The red coloring composition for a color filter of the present invention is prepared by mixing several kinds of pigments including the anthraquinone pigment and diketopyrrolopyrrole pigment of the present invention, and finely mixing the resulting pigment mixture in a pigment carrier by a known method. It can be dispersed and manufactured. The red coloring composition can also be produced by mixing each pigment separately finely dispersed in a pigment carrier.

In the red coloring composition for a color filter of the present invention, the pigment is prevented from agglomerating, the pigment is kept in a finely dispersed state, has both good fluidity and stability, and has excellent film thickness uniformity. In order to obtain a composition, an anthraquinone pigment derivative and a diketopyrrolopyrrole pigment derivative, which are a basic group of the following formula (4), a basic group of the formula (5), a basic group of the formula (6), and Those having at least one basic group selected from the basicity of formula (7) (hereinafter sometimes referred to as “specific basic group”) are included. Furthermore, it is at least one derivative selected from other pigment derivatives, anthraquinone derivatives, acridone derivatives or diketopyrrolopyrrole derivatives, and includes a basic group of the following formula (4), a basic group of the formula (5), a formula ( Those having at least one basic group selected from the basic group of 6) and the basic group of formula (7) (hereinafter sometimes referred to as “specific basic group”) may also be included.

式（５）

式（６）

式（７）

（上記式（４）〜（７）において、Ｘは、−ＳＯ₂−、−ＣＯ−、−ＣＨ₂ＮＨＣＯＣＨ₂−、−ＣＨ₂−または直接結合を表し、ｎは、１〜１０の整数を表し、Ｒ₁およびＲ₂は、それぞれ独立に、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基もしくは置換されていてもよいフェニル基を表すか、またはＲ₁とＲ₂とが結合して更なる窒素、酸素または硫黄原子を含む置換されていてもよい複素環を形成し、Ｒ₃は、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表し、Ｒ₄、Ｒ₅、Ｒ₆およびＲ₇は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、炭素数２〜３６の置換されていてもよいアルケニル基または置換されていてもよいフェニル基を表し、Ｙは、−ＮＲ₈−Ｚ−ＮＲ₉−または直接結合を表し、Ｒ₈およびＲ₉は、それぞれ独立に、水素原子、炭素数１〜３６の置換されていてもよいアルキル基、置換されていてもよい炭素数２〜３６のアルケニル基または置換されていてもよいフェニル基を表し、Ｚは、炭素数１〜３６の置換されていてもよいアルキレン基、炭素数２〜３６の置換されていてもよいアルケニレン基、または置換されていてもよいフェニレン基を表し、Ｒは、式（８）で示される置換基、または式（９）で示される置換基を表し、Ｑは、水酸基、アルコキシル基、式（８）で示される置換基または式（９）で示される置換基を表す。）
式（８）

式（９）

Formula (4)

Formula (5)

Formula (6)

Formula (7)

(In the above formulas (4) to (7), X represents —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ — or a direct bond, and n represents an integer of 1-10. R ₁ and R ₂ each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Represents a group, or R ₁ and R ₂ are combined to form an optionally substituted heterocycle containing an additional nitrogen, oxygen or sulfur atom, and R ₃ is substituted with 1 to 36 carbon atoms. Represents an optionally substituted alkyl group, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group, and R ₄ , R ₅ , R ₆ and R ₇ are each independently Hydrogen atom, optionally substituted alkyl having 1 to 36 carbon atoms Group, a optionally substituted alkenyl or optionally substituted phenyl group having 2 to 36 carbon atoms, Y is, -NR ₈ -Z-NR ₉ - or a direct bond, R ₈ and R ₉ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. , Z represents an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group, and R represents a formula Represents a substituent represented by (8) or a substituent represented by formula (9), and Q represents a hydroxyl group, an alkoxyl group, a substituent represented by formula (8) or a substituent represented by formula (9). To express.)
Formula (8)

Formula (9)

The pigment derivative used for the anthraquinone pigment used in the red coloring composition for a color filter of the present invention is particularly preferably one having an anthraquinone skeleton from the viewpoint of the fluidity and stability of the pigment dispersion. Further, the pigment derivative used for the diketopyrrolopyrrole pigment preferably has a diketopyrrolopyrrole skeleton from the viewpoint of the fluidity and stability of the pigment dispersion.
The content of the derivative having the specific basic group is preferably 0.001 to 40% by weight, more preferably 1 to 20% by weight, based on the pigment.

Examples of the organic pigment constituting the pigment derivative having a specific basic group include diketopyrrolopyrrole pigments, azo pigments such as azo, disazo, polyazo, phthalocyanine pigments, diaminodianthraquinone, anthrapyrimidine, and flavantrons. Anthraquinone pigments such as anthrone, indanthrone, pyranthrone, violanthrone, quinacridone pigment, dioxazine pigment, perinone pigment, perylene pigment, thioindigo pigment, isoindoline pigment, isoindolinone pigment, quinophthalone pigment Selenium pigments and metal complex pigments. Moreover, the pigment used for the red coloring composition of this invention shown previously may be sufficient.

Anthraquinone and acridone constituting an anthraquinone derivative having a specific basic group and an acridone derivative having a specific basic group are an alkyl group such as a methyl group, an ethyl group, an amino group, a nitro group, a hydroxyl group, or a methoxy group. Anthraquinone and acridone which may have a substituent such as an alkoxy group such as ethoxy group or a halogen such as chlorine.
In addition, diketopyrrolopyrrole constituting a diketopyrrolopyrrole derivative having a specific basic group is a saturated or unsaturated alkyl group that may be substituted, a cyano group, an aryl group that may be substituted, a halogen group, etc. It is diketopyrrolopyrrole which may have the following substituents.

Pigment derivatives, anthraquinone derivatives and acridone derivatives having a specific basic group can be synthesized by various synthetic routes. For example, after introducing a substituent represented by the following formulas (11) to (14) into an organic pigment, anthraquinone or acridone, it reacts with the substituent and is represented by general formulas (4) to (7). Amine components that form substituents such as N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3 It can be obtained by reacting 5-triazin-2-ylamino] aniline or the like.

Formula (11) -SO ₂ Cl
Formula (12) -COCl
Equation (13) -CH ₂ NHCOCH ₂ Cl
Equation (14) -CH ₂ Cl
When the organic pigment is an azo pigment, the basic group is introduced by introducing the substituent represented by the general formulas (4) to (7) into the diazo component or the coupling component in advance and then performing a coupling reaction. An azo pigment derivative having the same can also be produced.

In addition, diketopyrrolopyrrole derivatives having a specific basic group can also be synthesized by various synthetic routes. For example, an amine component starting from cyanuric chloride and forming a substituent represented by the general formulas (4) to (7) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N It is obtained by reacting methylpiperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.

Examples of the amine component used for forming a specific basic group include dimethylamine, diethylamine, N, N-ethylisopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N-tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, dibutylamine, disec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, dihexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N-methyloctadecylamine, didecylamine, diallylamine, N, N-ethyl- 1,2- Methylpropylamine, N, N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethyl Aminobutylamine, 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- Tylhexylaminoethylamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecoline, 3-pipecholine, 4-pipecholine, 2,4- Lupetidine, 2,6-lupetidine, 3,5-lupetidine, 3-piperidinemethanol, pipecolic acid, isonipecotic acid, methyl isonipecotate, ethyl isonipecotate, 2-piperidineethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine N-aminoethyl-4-pipecoline, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecoline, N-aminopropyl-4-pipecoline, N-aminopropylmorpholine, N -Methylpiperazine, N-butylpiperazine, N-methylhomopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, 1-cyclopentylpiperazine and the like.

Specific examples of the derivative having a specific basic group are shown below, but are not limited thereto. Among these derivatives, anthraquinone pigment derivatives include derivatives 1 to 7, and diketopyrrolopyrrole pigment derivatives include derivative 53. In the present invention, anthraquinone pigment derivatives and diketopyrrolopyrrole pigment derivatives And at least one each. Furthermore, the derivative | guide_body which can be used together can be used individually or in mixture of 2 or more types.

The pigment carrier in which the pigment contained in the red coloring composition of the present invention is dispersed is composed of a transparent resin, a precursor thereof, or a mixture thereof. The transparent resin is a resin having a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Transparent resins include thermoplastic resins, thermosetting resins, and active energy ray curable resins, and precursors thereof include monomers or oligomers that are cured by irradiation with active energy rays to form transparent resins. These can be used alone or in admixture of two or more.
When the composition is cured by ultraviolet irradiation, a photopolymerization initiator or the like is added to the red coloring composition.

Examples of the thermoplastic resin include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, and polyester resin. Acrylic resins, alkyd resins, polystyrene resins, polyamide resins, rubber resins, cyclized rubber resins, celluloses, polyethylene (HDPE, LDPE), polybutadiene, polyimide resins, and the like. Examples of the thermosetting resin include epoxy resins, benzoguanamine resins, rosin-modified maleic acid resins, rosin-modified fumaric acid resins, melamine resins, urea resins, and phenol resins.

As the active energy ray-curable resin, a (meth) acryl having a reactive substituent such as an isocyanate group, an aldehyde group or an epoxy group on a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group or an amino group. A resin in which a photocrosslinkable group such as a (meth) acryloyl group or a styryl group is introduced into the linear polymer by reacting a compound or cinnamic acid is used. Further, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified products are also used.

The pigment carrier preferably contains a transparent resin obtained by copolymerizing the compound (a) represented by the general formula (10) and another compound (b) having an ethylenically unsaturated double bond. Since the transparent resin exhibits an excellent dispersion effect for almost all pigments, it functions to prevent the pigments from agglomerating in the coloring composition and to maintain a finely dispersed state of the pigments. Therefore, when the filter segment is formed using the red coloring composition of the present invention obtained by dispersing the pigment in the pigment carrier containing the transparent resin, a filter segment with few pigment aggregates can be formed. A color filter having high transmittance and brightness can be manufactured.

（Ｒ₁₀は、水素原子またはメチル基、Ｒ₁₁はアルキレン基、Ｒ₁₂は水素原子またはベンゼン環などの置換基を含んでもよい炭素数１〜２０のアルキル基を表す。ｍは１〜１５の整数を表す。） Formula (10)

(R ₁₀ represents a hydrogen atom or a methyl group, R ₁₁ represents an alkylene group, R ₁₂ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may contain a substituent such as a benzene ring. Represents an integer.)

The compound (a) represented by the general formula (10) which is a constituent component of the transparent resin has good adsorption / orientation on the pigment surface due to the effect of π electrons of the benzene ring. In particular, when (a) is paracumylphenol ethylene oxide or propylene oxide modified (meth) acrylate, its steric effect is added and a better adsorption / orientation plane can be formed on the pigment, which is more effective. . Although the carbon number of the alkyl group of R ₁₂ is from 1 to 20, preferably 1 to 10. When the number of carbon atoms is from 1 to 10, the alkyl group becomes an obstacle to suppress the approach between the resins and promote the adsorption / orientation to the pigment. Even the adsorption / orientation to the pigment surface is hindered. This becomes more prominent as the chain length becomes longer, and when the carbon number exceeds 20, the adsorption / orientation of the benzene ring is extremely lowered.

Examples of the compound (a) include phenol ethylene oxide modified (meth) acrylate, paracumylphenol ethylene oxide modified (meth) acrylate, nonylphenol ethylene oxide modified (meth) acrylate, nonylphenol propylene oxide modified (meth) acrylate and the like.

As the compound (b), (meth) acrylic acid, methyl (meth) acrylate, ethyl (meth) acrylate, (iso) propyl (meth) acrylate, (iso) butyl (meth) acrylate, (iso) pentyl (meth) Acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, benzyl (meth) acrylate, cyclohexyl (meth) acrylate, glycidyl (meth) acrylate, isobornyl (meth) acrylate acid phosphooxyethyl (meth) Examples thereof include acrylate, acid phosphooxypropyl (meth) acrylate, 3 chloro 2-acid phosphooxyethyl (meth) acrylate, and acid phosphooxypolyethylene glycol mono (meth) acrylate.

The proportion of the compound (a) in the compound constituting the transparent resin is preferably 0.1 to 50% by weight, more preferably 10 to 35% by weight. When the proportion of the compound (a) is less than 0.1% by weight, a sufficient pigment dispersion effect cannot be obtained, and when it is more than 50% by weight, the compatibility with other components in the coloring composition is lowered. In some cases, precipitation of the monomer or photopolymerization initiator may occur.
The weight average molecular weight (Mw) of the transparent resin is preferably 5,000 to 100,000, more preferably 10,000 to 50,000.

As monomers and oligomers, methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate , Polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di (meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol Tri (meth) acrylate, 1,6-hexanediol diglycidyl ether di (meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, neopen Tylglycol diglycidyl ether di (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate, epoxy (meth) acrylate, urethane Various acrylates and methacrylates such as acrylates, (meth) acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide , N-vinylformamide, acrylonitrile and the like, and these can be used alone or in admixture of two or more.

Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropane Acetophenone photopolymerization initiators such as -1-one, benzoin photopolymerization initiators such as benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, and benzyldimethyl ketal, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4 Benzophenone photopolymerization initiators such as phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2 Thioxanthone photopolymerization initiators 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-piperonyl-4,6-bis (Trichloromethyl) -s-triazine, 2,4-bis (trick (Romethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4 , 6-Bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine, etc. A polymerization initiator, a borate photopolymerization initiator, a carbazole photopolymerization initiator, an imidazole photopolymerization initiator, or the like is used.

The above photopolymerization initiators are used alone or in combination of two or more. As sensitizers, α-acyloxy ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone. , Camphorquinone, ethylanthraquinone, 4,4′-diethylisophthalophenone, 3,3 ′, 4,4′-tetra (t-butylperoxycarbonyl) benzophenone, 4,4′-diethylaminobenzophenone, etc. It can also be used together.

The red coloring composition of the present invention can be adjusted in the form of a solvent developing type or alkali developing type colored resist. The colored resist is obtained by dispersing a pigment in a pigment carrier containing a thermoplastic resin, a thermosetting resin or an active energy ray curable resin and a monomer, and a pigment composition composed of several or more types of pigments, if necessary. In addition to the photopolymerization initiator, it can be produced by finely dispersing in a pigment carrier using various dispersing means such as a three roll mill, a two roll mill, a sand mill, a kneader, and an attritor. The red coloring composition of the present invention can also be produced by mixing several pigments separately dispersed on a pigment carrier.

When dispersing the pigment in the pigment carrier, a dispersion aid such as a resin-type pigment dispersant and a surfactant can be appropriately used. The dispersion aid is excellent in dispersing the pigment and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, when a coloring composition obtained by dispersing the pigment in the pigment carrier using the dispersion aid is used. Provides a color filter excellent in transparency.

The resin-type pigment dispersant has a pigment affinity part that has the property of adsorbing to the pigment and a part that is compatible with the pigment carrier, and acts to stabilize the dispersion of the pigment on the pigment carrier by adsorbing to the pigment. It is something to do. Specific examples of resin-type pigment dispersants include polycarboxylic acid esters such as polyurethane and polyacrylate, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salts, polysiloxanes, long-chain polyaminoamide phosphates, hydroxyl group-containing polycarboxylic acid esters, their modified products, amides formed by the reaction of poly (lower alkyleneimines) with polyesters having free carboxyl groups, and the like Water-based dispersants such as oily dispersants such as salts, (meth) acrylic acid-styrene copolymers, (meth) acrylic acid- (meth) acrylic acid ester copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinylpyrrolidone Resin, water-soluble polymer, polyester Modified polyacrylate, ethylene oxide / propylene oxide addition compound, phosphate ester-based and the like are used, they can be used alone or in admixture of two or more.

Surfactants include sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate. , Lauryl sulfate monoethanolamine, lauryl sulfate triethanolamine, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate Anionic surfactants such as: polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene Nonionic surfactants such as nylphenyl ether, polyoxyethylene alkyl ether phosphate ester, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; chaotic properties such as alkyl quaternary ammonium salts and their ethylene oxide adducts Surfactants: Examples include amphoteric surfactants such as alkylbetaines such as alkyldimethylaminoacetic acid betaine and alkylimidazolines, and these can be used alone or in admixture of two or more.

In the red coloring composition of the present invention, a pigment is sufficiently dispersed in a pigment carrier, and applied to a transparent substrate such as a glass substrate so as to have a dry film thickness of 0.5 to 3 μm to form a filter segment. In order to facilitate this, a solvent can be included. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether toluene, methyl ethyl ketone. , Ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent and the like, and these are used alone or in combination.

In addition, the red coloring composition of the present invention may contain a storage stabilizer in order to stabilize the viscosity with time of the composition. Examples of the storage stabilizer include quaternary ammonium chlorides such as benzyltrimethyl chloride and diethylhydroxyamine, organic acids such as lactic acid and oxalic acid, and organic acids such as methyl ether, t-butylpyrocatechol, triethylphosphine, and triphenylphosphine. Examples thereof include phosphine and phosphite.
The pigment is preferably contained in the red coloring composition in a proportion of 1.5 to 12% by weight in total. In addition, the pigment is preferably contained in the final filter segment in a proportion of preferably 10 to 40% by weight, more preferably 20 to 40% by weight, with the remainder being substantially from the resinous binder provided by the pigment carrier. Become.

The red coloring composition of the present invention is prepared by means of centrifugal separation, sintering filter, membrane filter or the like, coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more and coarse particles It is preferable to remove the dust.

Next, the color filter will be described.
In the color filter of the present invention, three color filter segments of R (red), G (green), and B (blue) are formed on a transparent or reflective substrate. The red filter segment is formed by using the coloring composition of the present invention by a printing method or a photolithography method.
The green filter segment can be formed using a normal green coloring composition. The green coloring composition can be replaced with, for example, C.I. I. This is a composition obtained using a green pigment such as Pigment Green 7, 10, 36, 37. The yellow pigment can be used in combination with the green coloring composition.

The blue filter segment can be formed using a normal blue coloring composition. Instead of the red pigment, the blue coloring composition is, for example, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, and the like. Blue coloring compositions include C.I. I. Pigment Violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, and other purple pigments can be used in combination.

As the transparent substrate, a glass plate such as quartz glass, borosilicate glass, alumina silicate glass, soda lime glass whose surface is coated with silica, or a resin plate such as polycarbonate, polymethyl methacrylate, or polyethylene terephthalate is used.
As the reflective substrate, silicon or a substrate in which an aluminum, silver, silver / copper / palladium alloy thin film or the like is formed on the transparent substrate is used.

The formation of each color filter segment by the printing method can be patterned simply by repeating the printing and drying of the colored composition prepared as the above various printing inks. Therefore, the color filter manufacturing method is low-cost and excellent in mass productivity. ing. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In order to perform printing, it is preferable that the ink does not dry and solidify on the printing plate or on the blanket. Control of ink fluidity on a printing press is also important, and ink viscosity can be adjusted with a dispersant or extender pigment.

When forming each color filter segment by a photolithography method, the colored composition prepared as the solvent developing type or alkali developing type colored resist material is applied on a transparent substrate, such as spray coating, spin coating, slit coating, roll coating, etc. It is applied by a coating method so that the dry film thickness is 0.5 to 3 μm. If necessary, the dried film is exposed to ultraviolet light through a mask having a predetermined pattern provided in contact with or non-contact with the film. Then, after immersing in a solvent or an alkaline developer, or spraying the developer with a spray or the like to remove the uncured portion to form a desired pattern, the same operation is repeated for other colors to produce a color filter. be able to. Furthermore, in order to accelerate the polymerization of the colored resist material, heating can be performed as necessary. According to the photolithography method, a color filter with higher accuracy than the above printing method can be manufactured.

In development, an aqueous solution such as sodium carbonate or sodium hydroxide is used as an alkali developer, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added to a developing solution.
In order to increase the UV exposure sensitivity, after coating and drying the colored resist material, a water-soluble or alkali-soluble resin such as polyvinyl alcohol or a water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Thereafter, ultraviolet exposure can also be performed.

The color filter of the present invention can be produced by an electrodeposition method, a transfer method, or the like in addition to the above method, but the colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a transparent substrate and forming each color filter segment on the transparent conductive film by electrophoresis of colloidal particles. is there.
The transfer method is a method in which a color filter layer is formed in advance on the surface of a peelable transfer base sheet, and this color filter layer is transferred to a desired transparent substrate.

If a black matrix is formed in advance before forming the filter segment on the transparent substrate or the reflective substrate, the contrast ratio of the liquid crystal display panel can be further increased. As the black matrix, a chromium, chromium / chromium oxide multilayer film, an inorganic film such as titanium nitride, or a resin film in which a light-shielding agent is dispersed is used, but is not limited thereto. In addition, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then a filter segment may be formed. By forming the filter segment on the TFT substrate, the aperture ratio of the liquid crystal display panel can be increased and the luminance can be improved.

On the color filter of the present invention, an overcoat film, a columnar spacer, a transparent conductive film, a liquid crystal alignment film, and the like are formed as necessary.
The color filter is bonded to the counter substrate using a sealant, and after injecting liquid crystal from the injection port provided in the seal part, the injection port is sealed, and if necessary, a polarizing film or a retardation film is placed outside the substrate. A liquid crystal display panel is manufactured by bonding.
Such liquid crystal display panels include twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertical alignment (VA), and optically convented bend (OCB). It can be used for a liquid crystal display mode in which colorization is performed using a color filter.

Hereinafter, the present invention will be described by way of examples. In the examples, “parts” and “%” represent “parts by weight” and “% by weight”, respectively.
(Preparation of acrylic resin solution 1)
Place 800 parts of cyclohexanone in a reaction vessel equipped with a thermometer, cooling tube, nitrogen gas inlet tube, and stirrer in a separable four-necked flask, and heat to 100 ° C. while injecting nitrogen gas into the vessel. A mixture of 60.0 parts of styrene, 60.0 parts of methacrylic acid, 65.0 parts of methyl methacrylate, 65.0 parts of butyl methacrylate, and 10.0 parts of azobisisobutyronitrile was added dropwise over 1 hour to polymerize the reaction. Went.
After the dropwise addition, the mixture was further reacted at 100 ° C. for 3 hours, and then 2.0 parts of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour to obtain a weight average molecular weight. Of about 40000 (measured by GPC).
After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried 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%. Acrylic resin solution 1 was prepared.

(Preparation of acrylic resin solution 2)
In a reaction vessel similar to the preparation of the acrylic resin solution 1, 70.0 parts of cyclohexanone was charged, the temperature was raised to 80 ° C., and the inside of the reaction vessel was purged with nitrogen, then 13.3 parts of n-butyl methacrylate, 2- 4.6 parts of hydroxyethyl methacrylate, 4.3 parts of methacrylic acid, 7.4 parts of paracumylphenol ethylene oxide modified acrylate (“Aronix M110” manufactured by Toa Gosei Co., Ltd.), 2,2′-azobisisobutyronitrile 0 4 parts of the mixture were added dropwise over 2 hours. After completion of the dropwise addition, the reaction was continued for 3 hours to obtain an acrylic resin solution having a solid content of 30% and a weight average molecular weight of 26000.
After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried 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%. Acrylic resin solution 2 was prepared.

[Examples 1 to 6, Comparative Examples 1 and 2]
(Preparation of red treated pigment 1)
Anthraquinone red pigment C.I. I. Pigment Red 177 (“Chromophthalred A2B” manufactured by Ciba Specialty Chemicals): 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged in a stainless steel 1 gallon kneader (Inoue Seisakusho) at 120 ° C. for 8 hours. Kneaded. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, red-treated pigment 1 was obtained.

(Preparation of red treated pigment 2)
Diketopyrrolopyrrole red pigment C.I. I. Pigment Red 254 (“Irgazine diketopyrrolopyrrole RED BO” manufactured by Ciba Specialty Chemicals): 500 parts, sodium chloride: 500 parts, and diethylene glycol: 250 parts were charged in a stainless steel 1 gallon kneader (Inoue Seisakusho) at 120 ° C. For 8 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, red-treated pigment 2 was obtained.

(Method for producing pigment dispersion)
15.0 parts of a mixture of pigments and derivatives having the composition shown in Table 1, 50.0 parts of the acrylic resin solution 1 (the acrylic resin solution 2 was used in Examples 2 and 3), and 60.0 parts of cyclohexanone were uniformly stirred. After mixing, using a zirconia bead having a diameter of 1 mm, the mixture was dispersed for 3 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan), and then filtered with a 5 μm filter to prepare a pigment dispersion.

* 1 PY139: C.I. I. Pigment Yellow 139
("Irgafore Yellow 2R-CF" manufactured by Ciba Specialty Chemicals)
PO71: C.I. I. Pigment Orange 71
("Chromophthal Diketopyrrolopyrrole Orange TR" manufactured by Ciba Specialty Chemicals)
* 2 A pigment derivative means a derivative shown in [Mode for Carrying Out the Invention].

(Method for producing resist material)
Next, the mixture having the following composition was stirred and mixed so as to be uniform, and then filtered through a 1 μm filter to obtain an alkali developing red resist material.
Pigment dispersion of mixture shown in Table 1 60.0 parts Photopolymerization initiator 1.2 parts ("Irgacure 907" manufactured by Ciba Specialty Chemicals)
Trimethylolpropane triacrylate 4.2 parts (“NK ESTER ATMPT” manufactured by Shin-Nakamura Chemical Co., Ltd.)
Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 1.4 parts acrylic resin solution 1 11.0 parts cyclohexanone 23.2 parts

(Preparation of coating film)
The viscosity of the obtained resist material at 20 rpm and 25 ° C. was measured with an E-type viscometer (ELD viscometer: manufactured by Toki Sangyo Co., Ltd.) and evaluated. Further, the obtained resist material was spin-coated on a 360 mm × 465 mm size substrate having a plate thickness of 0.7 mm so that the average film thickness was 1.8 μm, dried at 70 ° C. for 30 minutes, and then the film thickness in the center portion. The average value of four film thicknesses (referred to as B) in a 200 mm portion from the center on the diagonal line (measured as A) was measured, and the film thickness uniformity was evaluated by the following formula. The evaluation results are shown in Table 2.
(A−B) × 100 / {(A + B) / 2} [%]
Further, the obtained resist material was applied on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.3 mm using a spin coater so that x = 0.640 and y = 0.330 were obtained. . Next, after drying at 70 ° C. for 20 minutes, ultraviolet exposure was performed with an integrated light amount of 150 mJ using an ultrahigh pressure mercury lamp. The coated substrate was heated at 230 ° C. for 1 hour and allowed to cool, and then the brightness (Y) of the obtained red coating film with a C light source using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.) Asked. Moreover, the film thickness of the cured coating film was measured with a stylus type surface shape measuring instrument (“Dektak 8” manufactured by Veeco). The evaluation results are shown in Table 2.

As shown in Table 2, compared with Comparative Example 1, in Examples 1 to 6, a low-viscosity and stable resist material can be obtained by optimizing the derivative species combined with each of the two types of red pigments. A uniform coating cured film can be obtained.

Claims (7)

A pigment carrier comprising a transparent resin, a precursor thereof or a mixture thereof, an anthraquinone pigment represented by the following general formula (1) or (2), and a diketopyrrolopyrrole type represented by the following general formula (3) At least one selected from the group consisting of a pigment, a basic group of the following formula (4), a basic group of the following formula (5), a basic group of the following formula (6), and a basic group of the following formula (7) A red coloring composition for a color filter, comprising an anthraquinone pigment derivative and a diketopyrrolopyrrole pigment derivative having two basic groups.
Formula (1)

Formula (2)

Formula (3)

(In the above formulas (1) and (2), A each independently represents a hydrogen atom or an alkyl group or aryl group which may have a substituent. In the above formula (3), B represents each independently. Represents a hydrogen atom, a saturated or unsaturated alkyl group which may be substituted, a cyano group, an aryl group which may be substituted, or a halogen atom.)
Formula (4)

Formula (5)

Formula (6)

Formula (7)

(In the above formulas (4) to (7), X represents —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ — or a direct bond, and n represents an integer of 1-10. R ₁ and R ₂ each independently represents an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. Represents a group, or R ₁ and R ₂ are combined to form an optionally substituted heterocycle containing an additional nitrogen, oxygen or sulfur atom, and R ₃ is substituted with 1 to 36 carbon atoms. Represents an optionally substituted alkyl group, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group, and R ₄ , R ₅ , R ₆ and R ₇ are each independently Hydrogen atom, optionally substituted alkyl having 1 to 36 carbon atoms Group, a optionally substituted alkenyl or optionally substituted phenyl group having 2 to 36 carbon atoms, Y is, -NR ₈ -Z-NR ₉ - or a direct bond, R ₈ and R ₉ each independently represents a hydrogen atom, an optionally substituted alkyl group having 1 to 36 carbon atoms, an optionally substituted alkenyl group having 2 to 36 carbon atoms, or an optionally substituted phenyl group. , Z represents an optionally substituted alkylene group having 1 to 36 carbon atoms, an optionally substituted alkenylene group having 2 to 36 carbon atoms, or an optionally substituted phenylene group, and R represents a formula Represents a substituent represented by (8) or a substituent represented by formula (9), and Q represents a hydroxyl group, an alkoxyl group, a substituent represented by formula (8) or a substituent represented by formula (9). To express.)
Formula (8)

Formula (9)

  The red coloring composition for a color filter according to claim 1, wherein the total content of the basic group-containing derivative is 0.001 to 40% by weight based on the total amount of the pigment.   Anthraquinone pigments are C.I. I. Pigment Red 177 and the diketopyrrolopyrrole pigment is C.I. I. The red coloring composition for a color filter according to claim 1, wherein the red coloring composition is Pigment Red 254.   Furthermore, C.I. I. Pigment Yellow 139 is included, The red coloring composition for color filters of any one of Claim 1 thru | or 3 characterized by the above-mentioned.   C. I. Pigment Red 177 and C.I. I. The red coloring composition for a color filter according to claim 3 or 4, wherein the ratio to Pigment Red 254 is from 1:99 to 40:60 by weight. The pigment carrier contains a transparent resin obtained by copolymerizing the compound (a) represented by the following general formula (10) and another compound (b) having an ethylenically unsaturated double bond. The red coloring composition for color filters according to any one of claims 1 to 5.
Formula (10)

(R ₁₀ represents a hydrogen atom or a methyl group, R ₁₁ represents an alkylene group, R ₁₂ represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms which may contain a substituent such as a benzene ring. Represents an integer.)   A color filter comprising a filter segment formed from the red coloring composition according to any one of claims 1 to 6.