JP6371652B2 - Red pigment dispersed resist composition for color filter - Google Patents

Description

  The present invention relates to a red pigment-dispersed resist composition for a color filter for a color filter used for a color liquid crystal display device, an image sensor, or the like.

  A color filter used in a color liquid crystal display device or the like has two or more kinds of fine bands (stripes) of different hues arranged in parallel on the surface of a transparent substrate such as glass, or fine pixels are fixed vertically and horizontally. It consists of things arranged in an array. The pixel size is as small as several tens to several hundreds of micrometers, and is arranged regularly in a predetermined order for each hue.

The color liquid crystal display device colors white light from the backlight through the color filter as described above, and displays a color image on the screen. Therefore, high transparency is required as the basic performance of the color filter. Therefore, conventionally, the dye has been manufactured by using a so-called dyeing method in which a dye excellent in color characteristics is dispersed in a resin in a molecular state and dyed. However, in recent years, with the diversification of applications, when it is required to improve reliability for long-term use such as heat resistance and light resistance, organic pigments are used in place of dyes whose reliability improvement is limited. It became so. Various methods such as a printing method, an ink jet method, and a photolithography method have been proposed as a method for producing a color filter.
More recently, in order to promote the power saving of liquid crystal display devices for portable devices in particular, the visible light transmission is increased, and a bright display screen can be obtained more efficiently with limited power consumption. There is a demand for a color filter having pixels that enable high contrast leading to high definition of the overall image.

The above visible light transmission and contrast performance greatly depend on the performance of the pigment dispersed in each color pixel of the color filter, but the performance required by using only one type of pigment in the red pixel. It is difficult to realize, and it has been proposed to use other toning pigments together.
For example, a system (for example, see Patent Document 1) in which a toned red pigment is used in combination with Pigment Red 177 as a main red pigment has been proposed. Here, Pigment Red 5, 9, 10, 17, 48: 1, 48: 2, 48: 3, 48, which are red pigments having a maximum absorption peak in the wavelength region of 535 to 555 nm as the toned red pigment. : 4, 52: 2, 119, 166, 216, 224, 226. However, the combination system of these red pigments has limitations in improving the transmittance and contrast performance.

Furthermore, a system in which Pigment Red 177 or 254 as a toning red pigment is used in combination with Pigment Red 242 as a main red pigment (see, for example, Patent Document 2) has been proposed. Also proposed is a system in which red pigments such as Pigment Red 177, 207, 209, 224, 242 and the like are used in combination with Pigment Red 254 as the main red pigment (see, for example, Patent Document 3 and Patent Document 4). Has been.
However, when Pigment Red 242 is used as the main pigment, there arises a problem that the color tone is biased to yellow. On the other hand, when Pigment Red 254 is used, the transmittance increases, but the contrast decreases as the thickness of the colored coating increases. Furthermore, due to the characteristics of the pigment, there are problems that the solvent resistance deteriorates and the heat resistance deteriorates (sublimates are generated).

  In recent years, the color reproduction region of the color filter has been expanded by adopting a backlight using an LED as a light source. However, since the wavelength of the light irradiated to each differs, the color pigment which can be utilized is limited. For example, in the case of a backlight using an LED as a light source, the above-described pigment combinations as described above require that the pixel pigment density be further increased due to the relationship of the light absorption wavelength range. Therefore, it is necessary to increase the concentration of the red pigment dispersed resist composition, and there is a problem that it is difficult to produce the composition itself and to stably store it over time. On the other hand, if the pigment concentration is set to a conventional general concentration, the pixel film thickness for obtaining the necessary color concentration becomes too thick, making it difficult to manufacture a color filter. Will occur.

To solve this problem, using Pigment Red 179 and Pigment Red 208 that match the wavelength of the light emitted from the LED, color density can be obtained without increasing the pixel pigment density, and the film thickness can be controlled. Although within the possible range, this system has the problem of inherently low brightness.
Furthermore, as a method for maintaining high coloring power and increasing the luminance with respect to the wavelength of light emitted from the LED, it is conceivable to use a red pigment such as Pigment Red 221 (for example, see Patent Document 5). ).
However, since Pigment Red 221 has a large viscosity increase in the dispersion process and it is difficult to ensure the stability of the dispersion over time, the known method can obtain appropriate fluidity and stability over time of the dispersion. could not.

Japanese Patent Laid-Open No. 10-148712 Japanese Patent Laid-Open No. 11-014824 JP 2002-372618 A JP 2003-248115 A JP2012-208329A

  The subject of this invention is providing the red pigment dispersion resist composition for color filters which is excellent in dispersion stability, coloring power, contrast, brightness, heat resistance, and solvent resistance.

The main pigment is C.I. I. Pigment Red 221, and the toning pigment is C.I. I. By using Pigment Red 177, there is a possibility of obtaining a red pixel that can have high luminance and high coloring power even if various backlight devices are used. For that purpose, it is necessary to make these pigments into fine particles and stably disperse them in the red pigment dispersion resist composition for color filters. I. The dispersion stability of the fine particles of the pigment containing Pigment Red 221 cannot be sufficiently obtained.
Therefore, the applicant of the present application I. As a result of intensive studies on a technique for improving the dispersion stability of fine particles of pigment containing Pigment Red 221, C.I. I. The pigment dispersion aid specified in the present invention, an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group, and an organic solvent are added to the fine particles obtained by making the pigment containing Pigment Red 221 into fine particles. In addition, after obtaining a pigment dispersion by dispersion, a method for forming a red pigment dispersion resist composition for a color filter was found. In the red pigment dispersion resist composition for a color filter obtained from this method, C.I. I. The dispersion stability of the fine particles of the pigment containing Pigment Red 221 is significantly improved even when compared with the prior art, so that all the problems of the present invention can be solved, and thus the present invention has been completed. .

That is, the present invention
1. C. I. Pigment red 221, C.I. I. Pigment Red 177, a pigment dispersion aid represented by the general formula (1) and / or (2), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment for a color filter Dispersed resist composition.
[Wherein X and Y are the same or different and each represents a phenyl group which may be substituted with F, Cl, Br, NO ₂ , CH ₃ or OCH ₃ . M is H, Na, K, NH ₄ or NR ₁ R ₂ R ₃ R ₄ (R ₁ , R ₂ , R ₃ and R ₄ are the same or different and may be substituted with other substituents. Represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. m represents an integer of 1 or more. ]

2. C. I. Pigment Red 221 pigment dispersion, C.I. I. Pigment Red 177 pigment dispersion, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment dispersion resist composition for a color filter,
C. above. I. Pigment Red 221 pigment dispersion is C.I. I. Pigment Red 221 is made into fine particles, and the pigment dispersion aid represented by the general formula (1) and / or (2) is combined with an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (1) and / or (2) is added to a fine particle obtained by making Pigment Red 177 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by dispersing a polymer and an organic solvent.
A red pigment-dispersed resist composition for a color filter.
[Wherein X and Y are the same or different and each represents a phenyl group which may be substituted with F, Cl, Br, NO ₂ , CH ₃ or OCH ₃ . M is H, Na, K, NH ₄ or NR ¹ R ² R ³ R ⁴ (R ¹ , R ² , R ³ and R ⁴ are the same or different and may be substituted with other substituents. Represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. m represents an integer of 1 or more. ]

3. C. I. Pigment Red 221 pigment dispersion, C.I. I. Pigment Red 177 pigment dispersion, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment dispersion resist composition for a color filter,
C. above. I. Pigment Red 221 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 221 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. The pigment dispersion aid represented by the general formula (3) and / or (4) is added to the fine particles obtained by making Pigment Red 177 into fine particles, an acrylic block copolymer having a quaternary ammonium group, and an organic solvent. In addition, it is a pigment dispersion obtained by dispersing.
A red pigment-dispersed resist composition for a color filter.
[Wherein M is H, Na, K, NH ₄ or NR ¹ R ² R ³ R ⁴ (R ¹ , R ² , R ³ and R ⁴ are the same or different and are substituted with other substituents; A saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with another substituent). Represent. m represents an integer of 1 or more. ]

4). C. above. I. Pigment Red 221 pigment dispersion is C.I. I. The red pigment dispersion resist composition for color filters according to any one of 1 to 3, which contains a sulfonated compound having the same skeleton as that of Pigment Red 221.

5. Pigment Red 221 pigment dispersion is C.I. I. In the presence of a sulfonated compound having the same skeleton as CI Pigment Red 221, C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 221 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 177 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent and dispersing the polymer,
4. A red pigment-dispersed resist composition for color filters according to 4.

6). C. above. I. Pigment Red 221 Pigment Dispersion contains barium sulfate having a primary particle size of 5 to 20 nm, the C.I. I. The red pigment-dispersed resist composition for color filters according to any one of 1 to 5, which is contained in an amount of 5 to 15 parts by mass with respect to 100 parts by mass of the total mass of CI Pigment Red 221.

A color filter obtained by using the red pigment dispersed resist composition for color filter according to any one of 7.1 to 3 and having a color filter contrast (Bare: 1000) of 700 or more.

According to the present invention, the following effects can be obtained.
By using it as a pigment-dispersed resist composition for a color filter, a red filter having an appropriate chromaticity x and y is obtained, and thus a bright display with higher luminance Y is obtained.
The viscosity of the pigment-dispersed resist composition can be adjusted to an appropriate range, the film thickness can be reduced, and the production of the color filter does not become difficult.
The pigment dispersion resist composition for color filters can have excellent dispersion stability.
A red filter excellent in solvent resistance and heat resistance can be provided.

Hereinafter, the red pigment dispersion resist composition for color filters of the present invention (hereinafter also referred to as “pigment dispersion resist composition”) will be described in more detail.
(Pigment)
The red pigment dispersion resist composition for a color filter of the present invention includes C.I. I. Pigment red 221 and C.I. I. It is a composition containing CI Pigment Red 177, and these pigments may be directly added to form a red pigment dispersion resist composition for a color filter, or these pigments may have general formulas (1) and / or (2) in advance. A pigment dispersing aid represented by the formula (3), an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group, an organic solvent, and, if necessary, an alkali-soluble resin are added and dispersed. I. Pigment red 221 pigment dispersion, and C.I. I. After preparing Pigment Red 177 pigment dispersions, these pigment dispersions may be contained.
By obtaining a color filter using a pigment-dispersed resist composition containing this pigment dispersion, the color filter can have high contrast, high brightness, high heat resistance, and high solvent resistance.

C. above. I. The content of Pigment Red 221 is preferably 30% by mass or more and less than 100% by mass, more preferably 40% by mass or more and less than 60% by mass, based on the total mass of these pigments. I. Pigment Red 177 is preferably less than 70% by mass, more preferably 40% by mass or more and less than 60% by mass. C. above. I. When the content of Pigment Red 221 is less than 30% by mass, appropriate chromaticity x and y as a red filter may not be obtained.
C. above. I. Pigment red 221 and C.I. I. It is preferable that each pigment red 177 has an average primary particle diameter of 30 to 50 nm. By having an average particle diameter in the above range, the image projected by the obtained color filter has a higher contrast.
In addition, in this invention, the said average particle diameter means the volume average particle diameter measured with the laser diffraction type particle size measuring method and the measuring apparatus: Nanotrack (UPA-EX150, Nikkiso Co., Ltd. make).
In the present invention, in addition to the above color pigment, other pigments can be added and mixed within a range not impairing the effects of the present invention. Examples of the other pigments include yellow pigments and orange pigments.
The amount of the pigment used in the present invention is preferably 5 to 80% by mass, more preferably 20 to 50% by mass, based on the total amount of the pigment used, as a mass fraction based on the total solid content of the pigment-dispersed resist composition. is there.

(Pigment dispersion aid)
The pigment dispersion aid contained in the pigment dispersion resist composition of the present invention is a pigment dispersion aid (A) (hereinafter simply referred to as “pigment”) which is a compound represented by the following general formula (1) and / or general formula (2). Dispersion aid (A) "), and C.I. I. Both of two types of pigment dispersion aids, pigment dispersion aid (B) (hereinafter also simply referred to as “pigment dispersion aid (B)”), which is a sulfonated product of a compound having the same skeleton as Pigment Red 221, Although it is preferable to contain, it is not necessary to contain only a pigment dispersion aid (A) and a pigment dispersion aid (B).
Preferably, both the pigment dispersion aid (A) and the pigment dispersion aid (B) are included.

As the pigment dispersion aid (A) used in the present invention, a compound represented by the above general formula (1) and / or general formula (2) is used.
In the general formulas (1) and (2), X and Y are the same or different and each represents a phenyl group which may be substituted with F, Cl, Br, NO ₂ , CH ₃ or OCH ₃ . M represents H, Na, K, NH ₄ or NR ¹ R ² R ³ R ⁴ .
When M in the general formulas (1) and (2) is NR ¹ R ² R ³ R ⁴ , each R ¹ , R ² , R ³ and R ⁴ are the same or different and are substituted with other substituents. Represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with another substituent.
Here, as the saturated or unsaturated aliphatic hydrocarbon group, methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, s-butyl group, t-butyl group, pentyl group, hexyl group Alkyl groups such as octyl group and decyl group; alkenyl groups such as vinyl group, allyl group and 1-butenyl group; alkynyl groups such as ethynyl group and propynyl group. Examples of the aromatic hydrocarbon group include a phenyl group and a naphthyl group.
Moreover, as said other substituent, a hydroxyl group, a halogen, a carboxyl group, an amino group, a lower alkyl group (C1-C5) etc. are mentioned. In addition, as for said R < ¹ > R < ² > R < ³ > and R < ⁴ >, one may be substituted by the other substituent, or two or more may be substituted by the other substituent. Furthermore, “m” in the general formulas (1) and (2) is an integer of 1 or more.

In the pigment dispersion aid (A), the compound represented by the general formula (1) is an enol type, and the compound represented by the general formula (2) is a keto type tautomer. The pigment-dispersed resist composition can contain both compounds. That is, the pigment dispersion aid (A) in the present invention is represented by the compound represented by the general formula (1) or the general formula (2), and the general formula (1) or the general formula (2). And the case of consisting of both compounds.
Preferable examples of the pigment dispersion aid (A) include a pigment dispersion that has good fluidity and dispersion stability, and has a higher level of transparency and coloring power even when the organic pigment is finely dispersed. From the point that C. can be obtained. I. A sulfonated product of Pigment Red 2 (the following general formula (3) and / or general formula (4)) is preferable.

  The pigment dispersion aid (A) is used in an amount of 0.5 to 30 parts by weight, preferably 3 to 15 parts by weight, and the pigment dispersion aid (B) based on 100 parts by weight of each pigment. . I. The used amount of the sulfonated product of Pigment Red 221 is 0.5 to 30 parts by mass, preferably 3 to 15 parts by mass with respect to a total of 100 parts by mass of each pigment.

(Acrylic block copolymer having tertiary amino group and / or quaternary ammonium group)
The pigment-dispersed resist composition of the present invention contains an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group.
Examples of the acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group in the present invention include DISPERBYK-2000, DISPERBYK-2001, DISPERBYK-2020, DISPERBYK-2025, BYK-LPN21116, and BYK-LPN22102. (Above, manufactured by BYK Corporation).

  In the pigment-dispersed resist composition of the present invention, the content of the acrylic block copolymer having the tertiary amino group and / or quaternary ammonium group is usually 1 to 100 parts by mass of the total organic pigment used. It is preferable that it is 200 mass parts, More preferably, it is 1-60 mass parts. When the content of the acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is less than 1 part by mass, the pigment dispersibility may be lowered. There is a risk that the performance will be reduced.

(Alkali-soluble resin)
The pigment-dispersed resist composition of the present invention contains an alkali-soluble resin.
The alkali-soluble resin is not particularly limited as long as it is soluble in a developing solution used in the development processing step, particularly preferably an alkali developing solution, when producing a color filter. Among these, as the alkali-soluble resin, an alkali-soluble resin having a carboxyl group is preferable, and in particular, an ethylenically unsaturated monomer having one or more carboxyl groups and another copolymerizable ethylenically unsaturated monomer. A copolymer with the body is preferred.
Specific examples of the copolymer of the ethylenically unsaturated monomer having one or more carboxyl groups and other copolymerizable ethylenically unsaturated monomers include acrylic acid and methacrylic acid. Ethylenically unsaturated monomer having carboxyl group, styrene, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, allyl acrylate, allyl methacrylate, benzyl copolymerizable with ethylenically unsaturated monomer having carboxyl group Selected from the group consisting of acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, glycerol monoacrylate, glycerol methacrylate, N-phenylmaleimide, polystyrene macromonomer and polymethylmethacrylate macromonomer Even without mention may be made of a copolymer of one ethylenically unsaturated monomer.

The acid value of the alkali-soluble resin is preferably 50 to 300 mgKOH / g. In this case, if the acid value is less than 50 mgKOH / g, the solubility of the resist composition in an alkaline developer may be lowered. On the other hand, if it exceeds 300 mgKOH / g, the solubility in an alkali developer becomes excessive, and when developing with an alkali developer, the colored layer may fall off the substrate or the colored layer surface may become rough.
In the present invention, the acid value is a theoretical acid value, and is a value obtained arithmetically based on the ethylenically unsaturated monomer having a carboxyl group and its content.

The pigment-dispersed resist composition of the present invention contains an alkali-soluble resin, but the content thereof is preferably a small amount from the viewpoint of dispersibility and dispersion stability during pigment dispersion described later.
Therefore, C.I. I. Pigment red 221 pigment dispersion, and C.I. I. It is preferably contained in at least one of the pigment dispersions of Pigment Red 177, and may be added separately from these pigment dispersions to obtain a red pigment dispersion resist composition for a color filter.
In general, the mass average molecular weight of the alkali-soluble resin in the present invention is preferably 1,000 to 100,000. If the mass average molecular weight of the alkali-soluble resin is less than 1,000, the solubility in an alkali developer may increase and the development characteristics may deteriorate. On the other hand, when it exceeds 100,000, the solubility in an organic solvent may decrease, and the viscosity of the resist composition may increase.
In the present invention, the mass average molecular weight of the alkali-soluble resin is a polystyrene equivalent mass average molecular weight obtained based on GPC. In the present invention, Water 2690 (manufactured by Waters) is used as the apparatus, and PLgel 5μ MIXED-D (manufactured by Polymer Laboratories) is used as the column.
In the pigment dispersion resist composition of the present invention, the content of the alkali-soluble resin is usually preferably 10 to 1,000 parts by mass, more preferably 100 parts by mass of the total organic pigment contained. 20 to 500 parts by mass.
When the content of the alkali-soluble resin is less than 10 parts by mass, for example, alkali developability may be lowered, or background stains or film residues may be generated on the substrate or the light shielding layer in the unexposed area. On the other hand, when the amount exceeds 1,000 parts by mass, the concentration of the organic pigment is relatively lowered, so that it may be difficult to achieve the target color density as a thin film.

(Photopolymerizable compound)
The pigment-dispersed resist composition of the present invention contains a photopolymerizable compound.
Examples of the photopolymerizable compound in the present invention include monomers and oligomers having one or more photopolymerizable unsaturated bonds in the molecule. The photopolymerizable unsaturated bond is an unsaturated bond that can be polymerized by the action of radicals or cations generated when a photopolymerization initiator described later is decomposed by active energy rays such as ultraviolet rays and electron beams. .
Monomers having one photopolymerizable unsaturated bond in the molecule include alkyl methacrylates or acrylates such as methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, methyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate; benzyl Aralkyl methacrylate or acrylate such as methacrylate or benzyl acrylate; Alkoxyalkyl methacrylate or acrylate such as butoxyethyl methacrylate or butoxyethyl acrylate; Aminoalkyl methacrylate or acrylate such as N, N-dimethylaminoethyl methacrylate or N, N-dimethylaminoethyl acrylate Diethylene glycol ethyl ether, triethylene glycol butyl ether, dipropy Methacrylic acid ester or acrylic acid ester of polyalkylene glycol alkyl ether such as polyglycol glycol ether; Methacrylic acid ester or acrylic acid ester of polyalkylene glycol aryl ether such as hexaethylene glycol phenyl ether; Isobonyl methacrylate or acrylate; Acrylate; 2-hydroxyethyl methacrylate or acrylate can be exemplified.

In addition, monomers having two or more photopolymerizable unsaturated bonds in the molecule include bisphenol A dimethacrylate, 1,4-butanediol dimethacrylate, 1,3-butylene glycol dimethacrylate, diethylene glycol dimethacrylate, glycerol. Dimethacrylate, Neopentyl glycol dimethacrylate, Polyethylene glycol dimethacrylate, Polypropylene glycol dimethacrylate, Tetraethylene glycol dimethacrylate, Trimethylolpropane trimethacrylate, Pentaerythritol trimethacrylate, Pentaerythritol tetramethacrylate, Dipentaerythritol tetramethacrylate, Di Pentaerythritol hexamethacrylate, dipentaerythritol pentamethacrylate Bisphenol A diacrylate, 1,4-butanediol diacrylate, 1,3-butylene glycol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, neopentyl glycol diacrylate, polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene Examples include glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol triacrylate, pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, and dipentaerythritol pentaacrylate. These monomers can be used alone or in combination of two or more.
In the present invention, the content of the photopolymerizable compound is preferably in the range of 3 to 50% by mass with respect to the total solid content in the pigment-dispersed resist composition.

(Photopolymerization initiator)
The pigment dispersion resist composition of the present invention contains a photopolymerization initiator.
The photopolymerization initiator in the present invention is not particularly limited as long as it can generate radicals and cations when irradiated with active energy rays such as ultraviolet rays and electron beams. For example, benzophenone, N, N′-tetraethyl-4,4′-diaminobenzophenone, 4-methoxy-4′-dimethylaminobenzophenone, benzyl, 2,2-diethoxyacetophenone, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzyldimethyl ketal, α- Hydroxyisobutylphenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, t-butylanthraquinone, 1-chloroanthraquinone, 2,3-dichloroanthraquinone, 3-chloro-2-methylanthra Non, 2-ethylanthraquinone, 1,4-naphthoquinone, 1,2-benzoanthraquinone, 1,4-dimethylanthraquinone, 2-phenylanthraquinone, 2-methyl-1 [4- (methylthio) phenyl] -2-morpholinopro Pan-1-one, a triazine photopolymerization initiator, etc. are mentioned. These photoinitiators are used individually or in combination of 2 or more types.
In the present invention, the content of the photopolymerization initiator is preferably in the range of 1 to 20% by mass with respect to the total solid content in the pigment-dispersed resist composition.

(Organic solvent)
The pigment dispersion of the present invention contains an organic solvent.
Examples of the organic solvent in the present invention include organic solvents suitably used in the fields of ink, paint, liquid crystal color filter resist, and ink jet. Specifically, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono Ether organic solvents such as butyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether; ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene group Ether ester organic solvents such as coal monomethyl ether acetate and propylene glycol monoethyl ether acetate; ketone organic solvents such as methyl isobutyl ketone, cyclohexanone, 2-heptanone and δ-butyrolactone; methyl 2-hydroxypropionate and 2-hydroxypropion Ethyl acetate, ethyl 2-hydroxy-2-methylpropionate, 3-methyl-3-methoxybutylpropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, 3-ethoxy Ester organic solvents such as ethyl propionate, ethyl ethoxyacetate, ethyl hydroxyacetate and formic acid-n-amyl; alcoholic solvents such as methanol, ethanol, isopropyl alcohol and butanol; N Examples thereof include nitrogen-containing organic solvents such as methylpyrrolidone, N, N-dimethylformamide, and N, N-dimethylacetamide. These can be used individually or in mixture of 2 or more types.

Among these organic solvents, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, ethylene glycol monomethyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, cyclohexanone, 2 in terms of solubility, dispersibility, coatability, etc. -Heptanone, ethyl 2-hydroxypropionate, 3-methyl-3-methoxybutylpropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, n-amyl formate, etc. are preferred, propylene glycol monomethyl ether acetate It is more preferable that
Furthermore, these organic solvents are preferably contained in an amount of 50% by mass or more in the red pigment dispersion resist composition from the viewpoint of solubility, pigment dispersibility, coatability and the like of the alkali-soluble resin, and 70% by mass. It is more preferable that it is contained above.

(Other ingredients)
The pigment dispersion of the present invention preferably contains barium sulfate for the purpose of improving heat resistance and brightness. In this invention, content of barium sulfate is 0-15 mass parts with respect to 100 mass parts of said each pigment, Preferably it is 5-12 mass parts. When the said barium sulfate exceeds 15 mass parts, coloring power will fall significantly. The barium sulfate preferably has a primary particle size of 5 to 20 nm. When the primary particle diameter of the barium sulfate exceeds 20 nm, the contrast may decrease and foreign matter may tend to be generated. The barium sulfate is used during or after the dispersion of the finely divided pigment.
Moreover, the pigment dispersion resist composition of this invention can also use suitably various additives, such as a thermal-polymerization inhibitor, a ultraviolet absorber, and antioxidant, as needed.

(Method for producing pigment dispersion)
From the above constituent materials, the pigment dispersion in the present invention can be produced, for example, by the following production method.
First, each untreated pigment is subjected to a micronization process (salt milling process) to obtain a micronized pigment. More preferably, the micronization treatment is performed in the presence of a pigment dispersion aid that is a sulfonated product of a compound having the same skeleton as each pigment. By performing the micronization treatment in the presence of a pigment dispersing aid that is a sulfonated compound having the same skeleton as each pigment, uniform pulverization can be achieved while suppressing crystallization of the pigment. The particle diameter of the dispersion liquid composed of the refined pigment is about 50 to 70 nm.
The amount of the pigment dispersing aid used is 0.5 to 30 parts by mass, preferably 3 to 10 parts by mass with respect to 100 parts by mass of the pigment.
As the fine particle treatment, the pigment is ground with an inorganic salt in the presence of a sulfonated compound having the same skeleton as the pigment by using a kneader or a kneading device that revolves while rotating the three stirring blades. A salt milling treatment that crushes and further refines the primary particle diameter of the pigment is exemplified. The pigment obtained by the salt milling treatment in the presence of a sulfonated compound having the same skeleton as that of the pigment is finely divided so that the primary particle diameter becomes finer and uniform. In addition, the salt milling process using the kneading apparatus in which the three stirring blades revolve while rotating, respectively, is also referred to as a trimix process.

Hereinafter, the trimix process will be described in more detail.
The trimix treatment includes a pigment, a water-soluble inorganic salt (hereinafter also simply referred to as “inorganic salt”), and a water-soluble dispersion medium that does not substantially dissolve the inorganic salt (hereinafter also simply referred to as “dispersion medium”). Is mixed by a kneading apparatus that revolves while rotating three stirring blades, and then the inorganic salt and the dispersion medium are removed.
In this process, a kneading device in which three stirring blades move in a planetary motion, that is, a revolving motion while rotating, is used. As a result, the dead space between the stirring blades and between the stirring blade and the inner surface of the apparatus is greatly reduced, and a stronger and uniform shearing force can be obtained. The particle diameter of the pigment ground by the inorganic salt under the shearing force is finer and more uniform than the primary particle diameter, and a color filter having higher transparency and contrast ratio than the conventional one can be obtained. .
Here, “revolution motion” refers to a motion in which the stirring blade revolves within the tank. The “kneading device that revolves the stirring blade” means a kneading device that moves the stirring blade itself so that it moves around the tank. However, in this specification, if the relative motion of the tank and the stirring blade is the same (for example, the tank is rotated), the kneading device is also included in the “kneading device for rotating the stirring blade”.

Furthermore, as a structure of the kneading apparatus, it is preferable that the following conditions (1) and (2) are satisfied.
(1) A triangle obtained by using a point where the three rotation axes intersect with respect to a plane orthogonal to the rotation axis of the three stirring blades is an equilateral triangle.
(2) The revolution axis intersects the position of the center of gravity of the equilateral triangle.
The stirring blade preferably has a length extending from the bottom of the tank to the liquid level and a width from the inner wall of the tank to the center. Examples of such a kneading apparatus include Trimix (manufactured by Inoue Seisakusho Co., Ltd.).
In this treatment, a wet treatment method in which a pigment, an inorganic salt, and a dispersion medium are charged into a tank and kneaded can be used.
The inorganic salt is not particularly limited as long as it is water-soluble, but sodium chloride (sodium chloride) is preferably used from the viewpoint of cost.
Moreover, the particle diameter of the inorganic salt is preferably 200 μm or less, more preferably 50 μm or less. Thereby, the particle diameter of the color pigment can be made finer and uniform than the primary particle diameter.
In addition, in this invention, the particle diameter of the said inorganic salt means the volume average particle diameter measured with the laser diffraction type particle size measuring method and the measuring apparatus: Nanotrack (UPA-EX150, Nikkiso Co., Ltd. make).

The dispersion medium is not particularly limited as long as it is a water-soluble dispersion medium having both conditions of being water-soluble and not dissolving an inorganic salt. Among them, a high boiling point solvent having a boiling point of 120 ° C. or more is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent easily evaporates.
Examples of such a water-soluble dispersion medium include 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, 1-methoxy-2-propanol, and 1-ethoxy. Alkoxy alcohols such as 2-propanol; glycols such as diethylene glycol, triethylene glycol, liquid polyethylene glycol, dipropylene glycol, and low molecular weight polypropylene glycol; diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl And ethers such as ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether It is.

The following method etc. are mentioned as a method of performing a trimix process using the above material and apparatus.
A pigment, a pigment dispersion aid, an inorganic salt, and a dispersion medium, which are sulfonated compounds having the same skeleton as each pigment, are charged into a tank. Next, the three stirring blades of the kneading apparatus are revolved while rotating, and the pigment is ground with an inorganic salt. Thereafter, warm water is added to form a slurry, and the remaining inorganic salt and dispersion medium are removed by washing with water. In this pigment grinding treatment, it is preferable to appropriately adjust the amount of material charged (viscosity), the inner diameter of the tank, and the like so that sufficient stress for kneading is applied. For example, it is preferable to mix and process using the above trimix so that the load ampere at the time of processing is in the range of 50% to 85% of the rated current value of the motor.
Next, each finely divided product, the acrylic block copolymer having the tertiary and / or quaternary ammonium group, the pigment dispersion aid (A), the alkali-soluble resin, the organic solvent, and sulfuric acid as necessary. Each mixture containing barium is obtained. Each obtained mixture is kneaded and dispersed using various dispersers such as a roll mill, a kneader, a high-speed agitator, a bead mill, a ball mill, a sand mill, an ultrasonic disperser, and a high-pressure disperser. obtain. The pigment dispersion can also contain a photopolymerizable compound in advance.

(Method for producing pigment-dispersed resist composition)
A method for obtaining the pigment dispersion resist composition of the present invention from each pigment dispersion will be described.
About the method of obtaining the pigment dispersion resist composition of this invention from each pigment dispersion, it can obtain by following (1) and (2), for example.
(1) C.I. I. Pigment Red 221 pigment dispersion and C.I. I. After mixing each pigment dispersion of Pigment Red 177 pigment dispersion so as to have a predetermined pigment ratio, a photopolymerizable compound, a photopolymerization initiator, the remaining alkali-soluble resin, an organic solvent, and barium sulfate as necessary. Is added to obtain a pigment-dispersed resist composition.
(2) A photopolymerizable compound, a photopolymerization initiator, the remaining alkali-soluble resin, an organic solvent, and barium sulfate as necessary are added to each pigment dispersion to obtain each pigment-dispersed resist composition. I. Pigment Red 264 pigment-dispersed resist composition and C.I. I. Pigment Red 177 Pigment Dispersion Resist Composition is mixed so as to have a predetermined pigment ratio to obtain a Pigment Dispersion Resist Composition.

A color filter having a contrast (Bare: 1000) of 700 or more is obtained by producing a color filter using the pigment-dispersed resist composition obtained by the above method so as to have a predetermined method and film thickness. Can do.
In the present invention, the contrast is measured under the condition that the film thickness of the color filter is 1.0 μm, and the color characteristics (x, y, Y) of each resist are spectrophotometers (manufactured by Shimadzu Corporation, UV-2500PC, C This is the contrast (Bare: 1000) when the values measured at the light source (2 ° field of view) are chromaticity x = 0.6730 and y = 0.3200.
In the present invention, the contrast is more preferably 700 or more (Bare: 1000), and even more preferably 705 or more.

  The present invention will be described in more detail with reference to examples below, but the present invention is not limited to these examples. Unless otherwise specified, “%” means “mass%” and “part” means “part by mass”. Further, in this specification, “Trimix” is a registered trademark of Inoue Seisakusho Co., Ltd., and “Irgacure” is a registered trademark of Ciba Specialty Chemicals, Inc.

<Pigment dispersion aid>
(C.I. Pigment Red 221 sulfonated product)
A 100 ml Erlenmeyer flask was charged with 30 ml of concentrated sulfuric acid and stirred with a magnetic stirrer. I. 10 g of Pigment Red 221 was added and stirred at room temperature for 30 minutes. A mixture of 50 g of water and 50 g of ice was placed in a 1 L beaker, and the reaction product was poured into this ice water and stirred for 30 minutes with a magnetic stirrer. This was filtered and washed under reduced pressure, and the resulting solid was dried. I. 12 g of a sulfonated product of Pigment Red 221 was obtained.
(Sulfonated product of CI Pigment Red 2)
A 100 ml Erlenmeyer flask was charged with 30 ml of concentrated sulfuric acid and stirred with a magnetic stirrer. I. 10 g of Pigment Red 2 was added and stirred at room temperature for 30 minutes. A mixture of 50 g of water and 50 g of ice was placed in a 1 L beaker, and the reaction product was poured into this ice water and stirred for 30 minutes with a magnetic stirrer. This was filtered and washed under reduced pressure, and the resulting solid was dried. I. 12 g of a sulfonated product of Pigment Red 2 was obtained.
(C.I. Pigment Orange 71 sulfonated product)
A 100 ml Erlenmeyer flask was charged with 30 ml of concentrated sulfuric acid and stirred with a magnetic stirrer. I. 10 g of Pigment Orange 71 was added and stirred at room temperature for 30 minutes. A mixture of 50 g of water and 50 g of ice was placed in a 1 L beaker, and the reaction product was poured into this ice water and stirred for 30 minutes with a magnetic stirrer. This was filtered and washed under reduced pressure, and the resulting solid was dried. I. 12 g of a sulfonated product of Pigment Orange 71 was obtained.

<Particulate treatment>
Preparation Example 1 (Particulate Treatment PR221 (Pigment Red 221))
In the tank of Trimix TX-15 (trade name, manufactured by Inoue Seisakusho), C.I. I. 800 parts of Pigment Red 221, 8000 parts of sodium chloride having a particle size of 20 μm, and 1920 parts of diethylene glycol were added. The mixture was kneaded for 3 hours at 45 ° C. within a range of 70% of the rated current value of 9.3 A and subjected to salt milling. Next, 1300 parts of the obtained kneaded material was put into 3 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying overnight at 40 ° C. to obtain 720 parts of a micronized treatment PR221.

Preparation Example 2 (Pigment Dispersion Aid-Containing Fine Particle Treatment PR221 (Pigment Red 221))
In the tank of Trimix TX-15 (trade name, manufactured by Inoue Seisakusho), C.I. I. 800 parts of Pigment Red 221, C.I. I. 40 parts of a sulfonated product of Pigment Red 221, 8000 parts of sodium chloride having a particle size of 20 μm, and 1920 parts of diethylene glycol were added. The mixture was kneaded for 3 hours at 45 ° C. within a range of 70% of the rated current value of 9.3 A and subjected to salt milling. Next, 1300 parts of the obtained kneaded material was put into 3 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying overnight at 40 ° C. to obtain 740 parts of a pigment dispersion aid-containing micronized treatment PR221.

Preparation Example 3 (Pigment Red 254) Pigment Dispersing Aid Containing Fine Particle Treatment PR254
In the tank of Trimix TX-15 (trade name, manufactured by Inoue Seisakusho Co., Ltd.) I. 800 parts of Pigment Red 254, C.I. I. 40 parts of a sulfonated product of Pigment Orange 71, 8000 parts of sodium chloride having a particle diameter of 20 μm, and 1920 parts of diethylene glycol were added. The mixture was kneaded for 3 hours at 45 ° C. within a range of 70% of the rated current value of 9.3 A and subjected to salt milling. Next, 1300 parts of the obtained kneaded material was put into 3 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated until sodium chloride and diethylene glycol were removed, followed by drying overnight at 40 ° C. to obtain 740 parts of a pigment dispersion aid-containing micronized treatment PR254.

Preparation Example 4 (Particulate Treatment PR177 (Pigment Red 177))
In the tank of Trimix TX-15 (trade name, manufactured by Inoue Seisakusho Co., Ltd.) I. 800 parts of Pigment Red 177, 8000 parts of sodium chloride having a particle size of 20 μm, and 1920 parts of diethylene glycol were added. The mixture was kneaded for 3 hours at 45 ° C. within a range of 70% of the rated current value of 9.3 A and subjected to salt milling. Next, 1300 parts of the obtained kneaded material was put into 3 liters of warm water and stirred for 1 hour while heating to 70 ° C. to form a slurry. Filtration and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying overnight at 40 ° C. to obtain 720 parts of a micronized treatment PR177.

<Acrylic block copolymer having tertiary amino group and / or quaternary ammonium group>
BYK-LPN22102 (manufactured by BYK Corporation), solid content concentration 40% by mass
<Alkali-soluble resin>
BzMA / MAA copolymer (benzyl methacrylate / methacrylic acid copolymer, theoretical acid value: 120 mgKOH / g, mass average molecular weight: 25,000)
<Photopolymerizable compound>
DPEHA (dipentaerythritol hexaacrylate)
<Photopolymerization initiator>
Irgacure 369 (Ciba Specialty Chemicals, 2-benzyl 2-dimethylamino-1- (4-morpholinophenyl) -butanone-1)
<Organic solvent>
PGMEA (propylene glycol monomethyl ether acetate)
<Barium sulfate>
BF-40 (average primary particle size 0.01 μm, manufactured by Sakai Chemical Industry Co., Ltd.)

(Manufacture of dispersion and resist composition)
<Red pigment dispersion>
Each finely divided product for each dispersion is mixed with each other component so as to have the composition shown in Table 1, and kneaded at a temperature of 40 to 50 ° C. for 3 hours by a bead mill to obtain each red pigment dispersion. It was.
<Pigment-dispersed resist composition for color filter>
After uniformly mixing each pigment dispersion composition obtained in the above process and other materials (BzMA / MAA copolymer, DPHA, Irgacure, PGMEA) using a high-speed stirrer so as to have the composition shown in Table 1. The solution was filtered through a filter having a pore size of 3 μm to obtain a red pigment dispersed resist composition for each color filter.

<Red pigment dispersion resist composition for color filter of Examples and Comparative Examples>
The red pigment-dispersed resist compositions for color filters of Examples 1 to 9 and Comparative Examples 1 to 3 were obtained by combining the red pigment-dispersed resist compositions for color filters so as to have the formulations shown in Table 2.

Evaluation method The following evaluation is performed, and the evaluation results are shown in Tables 1 and 2.
<Viscosity>
About the pigment dispersion resist compositions for color filters of Examples and Comparative Examples, each was taken in a glass bottle, sealed, and stored at room temperature for 1 day, and then an E-type viscometer (R100-type viscometer model RE100L manufactured by Toki Sangyo Co., Ltd.) Was used to measure the viscosity at 25 ° C. The lower the viscosity, the better the fluidity and the better the pigment dispersion.

<Dispersion stability>
The pigment-dispersed resist compositions for color filters of Examples and Comparative Examples were each taken in glass bottles, sealed and stored at room temperature for 7 days, and evaluated according to the following evaluation criteria.
○: Neither thickening nor precipitate is observed △: Thickening or sedimenting enough to return to the original when lightly shaken is observed ×: Thickening or sedimenting enough to return to the original even when shaken strongly is recognized

<Evaluation of color characteristics of pigment dispersed resist composition for color filter>
The color characteristics (x, y, Y) of the resists of Examples and Comparative Examples having a film thickness of 1.0 μm were measured with a spectrophotometer (manufactured by Shimadzu Corporation, UV-2500PC, C light source 2 ° visual field). Here, in Examples 1 to 3 and Comparative Example 1, the contrast, luminance Y, and film thickness at chromaticity x = 0.6730 and y = 0.3200 were obtained. In Examples 4 to 6 and Comparative Example 2, the contrast, luminance Y, and film thickness were determined at chromaticity x = 0.6700 and y = 0.3122. In Examples 7 to 9 and Comparative Example 3, the contrast, luminance Y, and film thickness at chromaticity x = 0.6800 and y = 0.3150 were obtained.

<Heat resistance>
The pigment dispersed resist compositions for color filters of Examples and Comparative Examples were applied on a glass substrate using a spin coater so that the film thickness was 1.0 μm, prebaked at 100 ° C. for 3 minutes, and then with a high pressure mercury lamp. The film was exposed and further post-baked at 270 ° C. for 60 minutes. Thereafter, the surface of the obtained resist coating film was observed with a microscope (manufactured by Keyence Corporation, VHS-500, magnification 500 times), and the degree of surface roughness accompanying pigment sublimation during post-baking was observed. Evaluated according to.
○: Surface roughness is not recognized ×: Surface roughness is recognized

<Solvent resistance>
The test substrate used in the evaluation of the color characteristics was immersed in N-methylpyrrolidone for 30 minutes. After taking out the substrate, it was evaluated according to the following evaluation criteria.
○: Elution of coating film is not recognized ×: Elution of coating film is observed

According to the examples of Examples 1 to 3, the luminance when the required chromaticity x = 0.6730 and y = 0.3200 as a color filter was as bright as 15.90 to 16.00. In addition, the contrast at that time was high at 730 in Examples 1 and 2 compared to 1000 at Bare and sufficiently high at 530 according to Example 3. In addition, the color filters of Examples 1 to 3 all had good heat resistance and solvent resistance.
In contrast, C.I. I. According to Comparative Example 1 in which Pigment Red 221 was not used, the brightness of the obtained color filter was good, but the contrast, heat resistance, and solvent resistance were poor.
The same tendency was confirmed in the combination of Examples 4 to 6 and Comparative Example 2 and also in the combination of Examples 7 to 9 and Comparative Example 3.
As is apparent from these results, C.I. I. Rather than using Pigment Red 254, C.I. I. By adopting Pigment Red 221, a remarkable effect can be exhibited.

Claims (7)

C. I. Pigment red 221, C.I. I. Pigment Red 177, a pigment dispersion aid represented by the general formula (1) and / or (2), an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment for a color filter Dispersed resist composition.
[Wherein X and Y are the same or different and each represents a phenyl group which may be substituted with F, Cl, Br, NO ₂ , CH ₃ or OCH ₃ . M is H, Na, K, NH ₄ or NR ₁ R ₂ R ₃ R ₄ (R ₁ , R ₂ , R ₃ and R ₄ are the same or different and may be substituted with other substituents. Represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. m represents an integer of 1 or more. ] C. I. Pigment Red 221 pigment dispersion, C.I. I. Pigment Red 177 pigment dispersion, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment dispersion resist composition for a color filter,
C. above. I. Pigment Red 221 pigment dispersion is C.I. I. Pigment Red 221 is made into fine particles, and the pigment dispersion aid represented by the general formula (1) and / or (2) is combined with an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (1) and / or (2) is added to a fine particle obtained by making Pigment Red 177 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by dispersing a polymer and an organic solvent.
A red pigment-dispersed resist composition for a color filter.
[Wherein X and Y are the same or different and each represents a phenyl group which may be substituted with F, Cl, Br, NO ₂ , CH ₃ or OCH ₃ . M is H, Na, K, NH ₄ or NR ¹ R ² R ³ R ⁴ (R ¹ , R ² , R ³ and R ⁴ are the same or different and may be substituted with other substituents. Represents a saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with other substituents. m represents an integer of 1 or more. ] C. I. Pigment Red 221 pigment dispersion, C.I. I. Pigment Red 177 pigment dispersion, an alkali-soluble resin, a photopolymerizable compound, a photopolymerization initiator, and an organic solvent, a red pigment dispersion resist composition for a color filter,
C. above. I. Pigment Red 221 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 221 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. The pigment dispersion aid represented by the general formula (3) and / or (4) is added to the fine particles obtained by making Pigment Red 177 into fine particles, an acrylic block copolymer having a quaternary ammonium group, and an organic solvent. In addition, it is a pigment dispersion obtained by dispersing.
A red pigment-dispersed resist composition for a color filter.
[Wherein M is H, Na, K, NH ₄ or NR ¹ R ² R ³ R ⁴ (R ¹ , R ² , R ³ and R ⁴ are the same or different and are substituted with other substituents; A saturated or unsaturated aliphatic hydrocarbon group having 1 to 10 carbon atoms which may be substituted, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted with another substituent). Represent. m represents an integer of 1 or more. ]   C. above. I. Pigment Red 221 pigment dispersion is C.I. I. The red pigment dispersion resist composition for a color filter according to any one of claims 1 to 3, comprising a sulfonated compound having the same skeleton as that of Pigment Red 221. Pigment Red 221 pigment dispersion is C.I. I. In the presence of a sulfonated compound having the same skeleton as CI Pigment Red 221, C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 221 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent to disperse,
C. above. I. Pigment Red 177 pigment dispersion is C.I. I. A pigment dispersion aid represented by the general formula (3) and / or (4) is added to a fine particle obtained by making Pigment Red 177 into a fine particle, and an acrylic block copolymer having a tertiary amino group and / or a quaternary ammonium group is used. It is a pigment dispersion obtained by adding a polymer and an organic solvent and dispersing the polymer,
The red pigment dispersion resist composition for color filters according to claim 4.   C. above. I. Pigment Red 221 Pigment Dispersion contains barium sulfate having a primary particle size of 5 to 20 nm, the C.I. I. The red pigment-dispersed resist composition for a color filter according to any one of claims 1 to 5, wherein the composition is contained in an amount of 5 to 15 parts by mass with respect to 100 parts by mass of the total mass of Pigment Red 221.   A color filter obtained by using the red pigment-dispersed resist composition for a color filter according to claim 1, wherein the color filter has a contrast (Bare: 1000) of 700 or more.