WO2022102367A1 - Polymerizable polymer dispersant, pigment dispersion composition, and photosensitive coloring composition - Google Patents

Abstract

Provided are a polymerizable polymer dispersant having good pigment dispersibility and storage stability and a pigment dispersion composition that uses the polymerizable polymer dispersant. Also provided are a photosensitive coloring composition capable of obtaining a cured product having excellent solvent resistance, a color filter having the cured product, and an image display element equipped with the color filter. The polymerizable polymer dispersant includes an amino group (g-1) having an ethylenic unsaturated group. The amino group (g-1) is at least one amino group selected from the group consisting of secondary amino groups and tertiary amino groups.　

Description

Polymerizable polymer dispersants, pigment dispersion compositions, and photosensitive coloring compositions

The present invention relates to a polymerizable polymer dispersant, a pigment dispersion composition, a photosensitive coloring composition using the pigment dispersion composition, a color filter using the photosensitive coloring composition, and an image display element.
This application claims priority based on Japanese Patent Application No. 2020-189474 filed in Japan on November 13, 2020, the contents of which are incorporated herein by reference.

Currently, from the viewpoint of resource saving and energy saving, photosensitive resin compositions that can be cured by active energy rays such as ultraviolet rays and electron beams are widely used in various fields such as coatings, printing, paints, and adhesives. The photosensitive resin composition is used as a solder resist, a resist for a color filter, and the like in the field of electronic materials such as printed wiring boards.
The color filter is generally formed on a transparent substrate such as a glass substrate, red, green and blue pixels formed on the transparent substrate, a black matrix formed at the boundary of the pixels, and the pixels and the black matrix. It is composed of a protective film. A color filter having such a configuration is usually manufactured by sequentially forming a coloring pattern such as a black matrix or a pixel or a pattern such as a protective film on a transparent substrate. Various methods have been proposed as methods for forming various patterns. Among them, the pigment / dye dispersion method produced by a photolithography method in which a photosensitive resin composition is used as a resist and repeated coating, exposure, development and baking is excellent in durability and coloring with few defects such as pinholes. It is the current mainstream to give patterns.

Generally, the photosensitive resin composition used in the photolithographic method contains an alkali-soluble resin, a reactive diluent, a photopolymerization initiator, a pigment / dye dispersion composition (also referred to as a colorant), and a solvent. While the pigment / dye dispersion method has the above advantages, it repeatedly forms black matrix, red, green, and blue patterns, so it has heat resistance that can withstand high baking temperatures and is exposed during the manufacturing process. Resistance to various solvents is required.

In recent years, displays such as liquid crystals and organic EL are required to have high image quality and high definition, and color filters are also required to be designed to achieve high brightness and expansion of color reproduction range. In some cases, dyes are used instead of pigments as colorants for colorants in order to increase the brightness and expand the color reproduction range. Due to the limitation, the coloring material often contains a pigment. When forming a color filter using a pigment, uniform miniaturization of the pigment is indispensable. By making the pigment finer, the scattering of light transmitted through the color filter by the pigment particles is reduced, the contribution to the transmittance is high, and high brightness is achieved.
However, the finely divided pigment particles tend to aggregate, and there is a problem that the pigment dispersibility and the storage stability of the pigment dispersion composition tend to decrease. As a method for improving the dispersibility of the finely divided pigment, it is effective to use the pigment and the dispersant in combination.

Furthermore, in order to expand the color reproduction range, efforts are being made to increase the concentration of the coloring material of the colorant. As the concentration of the coloring material increases, the concentration of the dispersant and the concentration of other compositions decrease. Therefore, with a smaller amount of dispersant or other composition, the pigment dispersibility and the storage stability of the pigment dispersion composition, It is required to exhibit various resist properties such as heat resistance, solvent resistance, and pattern adhesion.

Generally, the dispersant has a portion that is adsorbed on the pigment and a moiety that has a high affinity with the solvent or other resin composition. The optimum structure of the portion adsorbed on the pigment changes according to the surface condition of the pigment. For example, a dispersant having a basic adsorption site is used for a pigment having an acid-biased surface, and in many cases, an amino group is used for the basic adsorption site as in Patent Document 1.
Further, in recent years, as in Patent Documents 2 and 3, a dispersant having a (meth) acryloyl group introduced into a dispersant having a basic adsorption site and having new functions such as adhesion and rubbing resistance has also been developed. Has been done.

Japanese Unexamined Patent Publication No. 2020-59821 Japanese Unexamined Patent Publication No. 2013-71973 Japanese Unexamined Patent Publication No. 2019-183051

However, when the dispersants disclosed in Patent Documents 1 to 3 are used, the pigment dispersibility is insufficient, and the storage stability of the pigment dispersion composition also needs to be improved. Further, since the dispersibility of the finely divided pigment is insufficient, there is a problem that the pigment particles aggregate and the brightness is lowered when used as a material for a color filter, and improvement has been sought.

The present invention has been made to solve the above-mentioned problems, and is a polymerizable polymer dispersant having good pigment dispersibility and storage stability, and a pigment dispersion composition using the polymerizable polymer dispersant. The purpose is to provide things.
Further, it is an object of the present invention to provide a photosensitive coloring composition capable of obtaining a cured product having excellent solvent resistance by using the pigment dispersion composition, a color filter having the cured product, and an image display element provided with the photosensitive coloring composition. The purpose.

The present invention includes the following aspects.
[1] Containing an amino group (g-1) having an ethylenically unsaturated group,
A polymerizable polymer dispersant, wherein the amino group (g-1) is at least one amino group selected from the group consisting of a secondary amino group and a tertiary amino group.
[2] The polymerizable polymer dispersant according to [1], wherein the amino group (g-1) has a (meth) acryloyloxy group.
[3] The polymerizable polymer dispersant according to [1] or [2], wherein the amino group (g-1) has a group represented by the following formula (1).
-CH ₂ -CH (OH) -R ¹ -O- (CO) -CR ² = CH ₂ (1)
(In the formula (1), R ¹ is a divalent linking group having 1 to 20 carbon atoms, and R ² represents a hydrogen atom or a methyl group.)
[4] Polymer dispersant (A) and
Pigment (B) and
A pigment dispersion composition containing a solvent (C-1).
The polymer dispersant (A) contains a polymerizable polymer dispersant (A-1) and a non-polymerizable polymer dispersant (A-2).
The polymerizable polymer dispersant (A-1) is the polymerizable polymer dispersant according to any one of [1] to [3].
The non-polymerizable polymer dispersant (A-2) does not have an ethylenically unsaturated group and is at least one substituent (g) selected from the group consisting of a tertiary amino group and a quaternary ammonium cation group. -2) A pigment dispersion composition comprising.
[5] Claimed that the content ratio (mass ratio) of the polymerizable polymer dispersant (A-1) and the non-polymerizable polymer dispersant (A-2) is 1:99 to 80:20. Item 4. The pigment dispersion composition according to Item 4.
[6] The non-polymerizable polymer dispersant (A-2) is
At least one monomer selected from the group consisting of a monomer having a tertiary amino group and an ethylenically unsaturated group, and a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group.
The pigment dispersion composition according to [4] or [5], which is a block polymer with another monomer having an ethylenically unsaturated group.

[7] The pigment dispersion composition according to any one of [4] to [6], wherein the pigment (B) contains a pigment having a halogenated phthalocyanine skeleton.
[8] The pigment dispersion composition according to any one of [4] to [7], which further contains a binder resin (D-1).
[9] With respect to 100 parts by mass of the pigment (B)
The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
The pigment dispersion composition according to [8], which contains 10 to 80 parts by mass of the binder resin (D-1).
[10] The pigment dispersion composition according to any one of [4] to [7] and
Binder resin (D-2) and
Reactive diluent (E) and
A photosensitive coloring composition comprising a photopolymerization initiator (F).
[11] With respect to 100 parts by mass of the pigment (B)
The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
The binder resin (D-2) is contained in an amount of 50 to 280 parts by mass.
40 to 200 parts by mass of the reactive diluent (E) is contained.
The photosensitive coloring composition according to [10], which contains 0.1 to 10 parts by mass of the photopolymerization initiator (F).
[12] The pigment dispersion composition according to [8] or [9] and
Binder resin (D-2) and
Reactive diluent (E) and
A photosensitive coloring composition comprising a photopolymerization initiator (F).
[13] With respect to 100 parts by mass of the pigment (B)
The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
A total of 50 to 280 parts by mass of the binder resin (D-1) and (D-2) is contained.
40 to 200 parts by mass of the reactive diluent (E) is contained.
The photosensitive coloring composition according to [12], which contains 0.1 to 10 parts by mass of the photopolymerization initiator (F).
[14] A resin-cured film obtained by curing the photosensitive coloring composition according to any one of [10] to [13].
[15] A color filter having a cured product of the photosensitive coloring composition according to any one of [10] to [13].
[16] An image display element including the color filter according to [15].

According to the present invention, it is possible to provide a polymerizable polymer dispersant having good pigment dispersibility and storage stability, and a pigment dispersion composition using the polymerizable polymer dispersant. Further, by using the pigment dispersion composition, it is possible to provide a photosensitive coloring composition capable of obtaining a cured product having excellent solvent resistance. Further, it is possible to provide a color filter having a cured product of the photosensitive coloring composition and an image display element provided with the color filter.

Hereinafter, embodiments of the present invention will be described in detail. However, the present invention is not limited to the embodiments shown below. In addition, in this specification, "(meth) acryloyloxy group" represents one or more selected from a methacryloyloxy group and an acryloyloxy group. The same applies to "(meth) acrylic acid".

<Polymerizable polymer dispersant (A-1)>
The polymerizable polymer dispersant (A-1) contains an amino group (g-1) having an ethylenically unsaturated group, and the amino group (g-1) is composed of a secondary amino group and a tertiary amino group. It is at least one amino group selected from the group consisting of. As used herein, the secondary amino group refers to a group in which two carbon atoms and one hydrogen atom are bonded to a nitrogen atom, and does not include an amide bond or a urea bond. Similarly, the tertiary amino group refers to a group in which three carbon atoms are bonded to a nitrogen atom, and does not include those having an amide bond or a urea bond. Since the pigment dispersion composition described later contains the polymerizable polymer dispersant (A-1), the pigment dispersibility is good, and when the photosensitive coloring composition is photocured, the polymerizable polymer is obtained. A cured film having good developability because the ethylenically unsaturated group of the dispersant (A-1) is polymerized and incorporated into the cured product, and has good various performances such as heat resistance, solvent resistance, and pattern adhesion. Can be obtained. Further, the ethylenically unsaturated group contained in the polymerizable polymer dispersant (A-1) is polymerized and incorporated into the cured product, so that the effect of preventing the bleed-out of the pigment can be expected.

In particular, it is important that the polymerizable polymer dispersant (A-1) has an amine structure from the viewpoint of ensuring the storage stability and pigment dispersibility of the pigment dispersion composition. Therefore, when the following polymer dispersant is used in place of the polymerizable polymer dispersant (A-1), the storage stability and pigment dispersibility of the pigment dispersion composition are significantly reduced. The above-mentioned polymer dispersant is, for example, an ethylenically unsaturated group formed by reacting an amino group of a polymer dispersant with a (meth) acrylic acid halide or a (meth) acrylic acid anhydride to form an amide bond. The introduced polymer dispersant or the polymer dispersant into which an ethylenically unsaturated group is introduced by reacting the amino group of the polymer dispersant with an ethylenically unsaturated compound having an isocyanato group to form a urea bond. Can be mentioned.

The ethylenically unsaturated group is not particularly limited, but is preferably an ethylenically unsaturated group possessed by the (meth) acryloyloxy group from the viewpoint of having good curability when made into a photosensitive composition. That is, it is preferable that the amino group (g-1) contained in the polymerizable polymer dispersant (A-1) has a (meth) acryloyloxy group.

The ethylenically unsaturated group is preferably an ethylenically unsaturated group having a group represented by the following formula (1) from the viewpoint of having an affinity with the pigment (B) described later. That is, it is preferable that the amino group (g-1) contained in the polymerizable polymer dispersant (A-1) has a group represented by the following formula (1).

-CH ₂ -CH (OH) -R ¹ -O- (CO) -CR ² = CH ₂ (1)
(In the formula (1), R ¹ is a divalent linking group having 1 to 20 carbon atoms, and R ² represents a hydrogen atom or a methyl group.)
The divalent linking group indicated by R ¹ has 1 to 20 carbon atoms, preferably 1 to 10 carbon atoms, and more preferably 1 to 6 carbon atoms. R ¹ may contain an ether bond or an ester bond, but is preferably an alkylene group.

The amino group (g-1) contained in the polymerizable polymer dispersant (A-1) is a secondary or tertiary amino group having an ethylenically unsaturated group. The structure of this amino group (g-1) is such that the amino group (g-0) of the polymer compound (a) having a primary and / or secondary amino group (g-0) is an ethylenically unsaturated monomer. It is obtained by adding (b).

Examples of the polymer compound (a) include a monomer having a primary amino group and an ethylenically unsaturated group, and a polymer compound obtained by homopolymerizing or copolymerizing a monomer having a secondary amino group and an ethylenically unsaturated group. Be done. For example, polyamine which is a polymer of vinylamine or allylamine, polyamine obtained by copolymerizing these monomers with other monomers having an ethylenically unsaturated group, polyalkyleneimine obtained by ring-opening polymerization of ethyleneimine, 2-oxazoline, etc., ethylenediamine. And polyalkyleneimine obtained by polycondensing a polyfunctional amine compound such as hexamethylenediamine with haloalkane and the like. Further, a graft polymer obtained by ring-opening polymerization of ethyleneimine, 2-oxazoline or the like to a copolymer having an electron-withdrawing functional group can be mentioned. Examples of the copolymer having an electron-withdrawing functional group include a copolymer of an acid group-containing monomer such as (meth) acrylic acid. In addition to the primary and / or secondary amino group (g-0), the polymer compound (a) includes a tertiary amino group, a quaternary ammonium cation group, and amides and imides as long as the effects are not impaired. , Urea, urethane and the like may be contained. Further, it does not prevent the ethylenically unsaturated monomer (b) from being added to these. As described above, since it is the amine structure that greatly contributes to the dispersibility of the pigment, it is preferable that the amide, imide, urea, and urethane bond are not substantially contained.

The amine content of the polymer compound (a) can be quantitatively determined by measuring the amine value (value measured according to the standard shown in JIS K7237 or the like). The amine content of the polymer compound (a) of the present embodiment is not particularly limited, but is preferably 10 mgKOH / g to 300 mgKOH / g, and more preferably 20 mgKOH / g to 200 mgKOH / g. When the amine value is 10 mgKOH / g or more, the ethylenically unsaturated monomer (b) described later can be added in a mild environment. As a result, it is possible to provide the polymer dispersant (A) having improved heat resistance, solvent resistance, and pattern adhesion of the colored pattern. At the same time, the affinity with the pigment (B) described later is enhanced, and sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained. On the other hand, when the amine value is 300 mgKOH / g or less, yellowing of the coloring pattern caused by amine can be suppressed.

Further, the molecular weight (weight average molecular weight in terms of polystyrene) of the polymer compound (a) of the present embodiment is not particularly limited, but is preferably 1000 to 200,000, more preferably 3000 to 100,000. When the molecular weight of the polymer compound (a) is within the above range, the viscosity of the pigment dispersion composition can be controlled within an appropriate range. As a result, sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained, and excellent heat resistance, solvent resistance, pattern adhesion, developability and the like can be ensured.

The polymer compound (a) may be a commercially available product or may be prepared by itself. When prepared by oneself, the polyamines, polyalkyleneimines and the like shown above are synthesized by using a known production method. When using commercially available products, examples of suitable polymer compounds include the Sol Spurs series manufactured by Lubrizol, the DISPERBYK series manufactured by Big Chemie, the Ajinomoto Fine Techno Co., Ltd. Azisper series, and the Epomin series manufactured by Nippon Shokubai. Polyment series and the like can be mentioned. These polymer compounds may be used alone or in combination of two or more, if necessary.

The ethylenically unsaturated monomer (b) is a compound having an ethylenically unsaturated group and added to a primary and / or a secondary amino group to form a secondary and / or a tertiary amino group. If there is, it is not particularly limited. Examples thereof include an ethylenically unsaturated monomer having a highly electrophilic substituent such as an epoxy group and a xetanyl group, and an ethylenically unsaturated monomer having a leaving group such as a halogen, azide and a sulfonic acid ester. Be done. Specifically, from the viewpoint of easy availability and good reactivity, it is preferable to use a monomer having an epoxy group or an oxetaneyl group, and in particular, glycidyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate glycidyl ether, 3 , 4-Epoxide cyclohexylmethyl (meth) acrylate, (3-ethyloxetane-3-yl) methyl (meth) acrylate are preferred.

Known as a method for adding a monomer having an epoxy group or an oxetanyl group as an ethylenically unsaturated monomer (b) to the primary and / or secondary amino group (g-0) of the polymer compound (a). It is preferable to utilize the ring-opening reaction of the epoxy group or oxetanyl group of. Specifically, the polymer compound (a), the ethylenically unsaturated monomer (b), and a solution are mixed at an arbitrary ratio, and if necessary, a catalyst or a polymerization inhibitor is added, and then the room temperature is maintained. It is obtained by reacting under the conditions of ~ 150 ° C., preferably 50 ° C. to 130 ° C.
The catalyst is not particularly limited as long as it enhances the nucleophilicity of the primary and / or secondary amine, or enhances the electrophilicity of the epoxy group or the oxetanyl group. Specific examples thereof include tertiary amines such as triethylamine, quaternary ammonium salts such as triethylbenzylammonium chloride, phosphorus compounds such as triphenylphosphine, and organometal compounds such as chromium and tin. Further, a polymerization inhibitor is added to prevent the ethylenically unsaturated group from polymerizing and gelling at a high temperature when the ethylenically unsaturated monomer (b) is added. The type is not particularly limited, and specific examples thereof include hydroquinone, methylhydroquinone, hydroquinone monomethyl ether, and dibutylhydroxytoluene.

The amount of the ethylenically unsaturated monomer (b) added to the primary and / or secondary amino group (g-0) of the polymer compound (a) is not particularly limited, but the polymer compound (a). When the total amount of amine is 1 equivalent, it is preferably 0.1 equivalent or more and 1 equivalent or less, more preferably 0.3 equivalent or more and 1 equivalent or less, and further preferably 0.6 equivalent or more and 1 equivalent or less. When 0.1 equivalent or more is added, the polymer dispersant (A) having improved heat resistance, solvent resistance, and pattern adhesion of the colored pattern can be provided, and the desired performance is obtained as the added amount increases. Can be granted.
In addition, the polymerizable polymer dispersant (A-1) in which the ethylenically unsaturated monomer (b) is added to the polymer compound (a) is not used as an index showing the amount of the ethylenically unsaturated group added. A saturated group equivalent (a value measured according to a standard shown in JIS K0070 or the like or a calculated value calculated based on an actual amount of a compound used) is widely used. The unsaturated group equivalent can be controlled by the addition amount of the ethylenically unsaturated monomer (b), and the unsaturated group equivalent of the polymerizable polymer dispersant (A-1) is not particularly limited, but is preferably 200 g / mol or more. It is 10000 g / mol or less, more preferably 300 g / mol or more and 5000 g / mol or less, and further preferably 500 g / mol or more and 2000 g / mol or less. Also here, when the unsaturated group equivalent is 10,000 g / mol or less, it is possible to provide the polymer dispersant (A) having improved heat resistance, solvent resistance and pattern adhesion of the coloring pattern, and the addition amount can be increased. The desired performance can be imparted as the amount of unsaturated group increases increases and the amount of unsaturated group becomes smaller. On the other hand, when the unsaturated group equivalent is 200 g / mol or more, it is possible to provide a practical polymer dispersant (A) that can guarantee stability during production.

Further, the amine content of the polymerizable polymer dispersant (A-1) of the present embodiment is preferably 10 mgKOH / g to 300 mgKOH / g as the amine value, similar to the amine content of the polymer compound (a). More preferably, it is 20 mgKOH / g to 200 mgKOH / g. When the amine value is 10 mgKOH / g or more, the affinity with the pigment (B) described later is enhanced, and sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained. On the other hand, when the amine value is 300 mgKOH / g or less, the yellowing of the coloring pattern caused by the amine can be suppressed.

Further, the molecular weight (weight average molecular weight in terms of polystyrene) of the polymerizable polymer dispersant (A-1) of the present embodiment is not particularly limited, but is preferably 1000 to 200,000, more preferably 3000 to 100,000. When the molecular weight of the polymerizable polymer dispersant (A-1) is within the above range, the viscosity of the pigment dispersion composition can be controlled within an appropriate range. As a result, sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained, and excellent heat resistance, solvent resistance, pattern adhesion, developability and the like can be ensured.

<Pigment dispersion composition>
The pigment dispersion composition of the present embodiment contains a polymer dispersant (A), a pigment (B), and a solvent (C-1). The pigment dispersion composition contains a binder resin (D-1), if necessary.

[Polymer dispersant (A)]
The polymer dispersant (A) of the present embodiment contains the polymerizable polymer dispersant (A-1) and the non-polymerizable polymer dispersant (A-2). The polymerizable polymer dispersant (A-1) contains an amino group (g-1) having an ethylenically unsaturated group, and the amino group (g-1) is a secondary amino group and a tertiary amino group. It is at least one amino group selected from the group consisting of. The non-polymerizable polymer dispersant (A-2) does not have an ethylenically unsaturated group and is at least one substituent (g) selected from the group consisting of a tertiary amino group and a quaternary ammonium cation group. -2) It is a compound having. Since the polymer dispersant (A) has an amine structure, excellent pigment dispersibility and storage stability can be obtained particularly when used in combination with a pigment (B) having an acid-biased surface.

[Polymerizable Polymer Dispersant (A-1)]
As the polymerizable polymer dispersant (A-1), the above-mentioned ones can be used.

[Non-polymerizable polymer dispersant (A-2)]
The non-polymerizable polymer dispersant (A-2) does not have an ethylenically unsaturated group and is at least one substituent (g-) selected from the group consisting of a tertiary amino group and a quaternary ammonium cation group. It is a compound having 2). The tertiary amino group and the quaternary ammonium cation group particularly contribute to the improvement of the dispersibility of the pigment (B). Therefore, by containing the non-polymerizable polymer dispersant (A-2) in the pigment dispersion composition of the present embodiment, the preservation is superior to that containing the polymerizable polymer dispersant (A-1) alone. Stability and pigment dispersibility can be ensured. Further, when the photosensitive coloring composition of the present embodiment contains the non-polymerizable polymer dispersant (A-2), it is possible to provide a color filter having high brightness and a wide color reproduction range.
The non-polymerizable polymer dispersant (A-2) is selected from the group consisting of a monomer having a tertiary amino group and an ethylenically unsaturated group and a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group. It is preferably a block polymer of at least one monomer and another monomer having an ethylenically unsaturated group. Examples of the other monomer having an ethylenically unsaturated group include (meth) acrylates having an alkyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylene glycol group and the like.

Specific examples of the non-polymerizable polymer dispersant (A-2) include the following compounds.
Polyamines (or polyammonium cationic salts) obtained by homopolymerizing or copolymerizing a monomer having a tertiary amino group and an ethylenically unsaturated group or a monomer having a quaternary ammonium cationic group and an ethylenically unsaturated group.
Polyamines (or polyammonary cationic salts) copolymerized with these monomers and other monomers having ethylenically unsaturated groups,
A compound obtained by alkylating a polymer compound containing one or more primary and / or secondary amino groups to form a tertiary amino group.
A compound obtained by further reacting an acidic compound or an alkyl halide compound on a tertiary amino group to form a quaternary ammonium cation salt.

Examples of the non-polymerizable polymer dispersant (A-2) include a monomer having a tertiary amino group and an ethylenically unsaturated group and / or a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group, and the like. A polyamine (or polyammonium cation salt) obtained by block-polymerizing a monomer having an ethylenically unsaturated group is preferable. By using a block-polymerized polyamine (or polyammonium cation salt) as the non-polymerizable polymer dispersant (A-2), tertiary amino groups and / or quaternary ammonium cation groups are unevenly distributed in one terminal region. The affinity with the pigment (B) described later is improved. Further, the other end region has an increased affinity with another pigment dispersion composition, specifically, a solvent (C-1) or a binder resin (D-1) described later, thereby improving the pigment dispersibility. The storage stability of the pigment dispersion composition can be dramatically improved.
As an example of a monomer having another ethylenically unsaturated group whose affinity with other pigment dispersion compositions can be enhanced, it has an alkyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylene glycol group and the like (meth). Examples include acrylate.

The amine content of the non-polymerizable polymer dispersant (A-2) is quantitatively determined by measuring the amine value (value measured according to the standard shown in JIS K7237 or the like). be able to. The amine content of the non-polymerizable polymer compound (A-2) of the present embodiment is not particularly limited, but is preferably 10 mgKOH / g to 200 mgKOH / g, and more preferably 30 mgKOH / g to 160 mgKOH / g. When the amine value is 10 mgKOH / g or more, the affinity with the pigment (B) described later is enhanced, and sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained. On the other hand, when the amine value is 200 mgKOH / g or less, the yellowing of the coloring pattern caused by the amine can be suppressed.
Further, the molecular weight (weight average molecular weight in terms of polystyrene) of the non-polymerizable polymer dispersant (A-2) of the present embodiment is not particularly limited, but is preferably 1000 to 50,000, more preferably 3000 to 30,000. Further, the molecular weight distribution (value obtained by dividing the polystyrene-equivalent weight average molecular weight by the number average molecular weight) of the non-polymerizable polymer dispersant (A-2) is preferably 1.0 to 2.0, more preferably 1. It is in the range of 0 to 1.7. When the molecular weight and molecular weight distribution of the non-polymerizable polymer dispersant (A-2) are within the above ranges, the viscosity of the pigment dispersion composition can be controlled within an appropriate range, and sufficient pigment dispersibility and pigment dispersion can be achieved. The storage stability of the composition is obtained. In particular, the narrower the molecular weight distribution, the more effectively the pigment dispersibility and the storage stability of the pigment dispersion composition can be obtained with a smaller amount of dispersant.

The non-polymerizable polymer dispersant (A-2) may be a commercially available product or may be prepared by itself. When a commercially available product is used, examples of suitable polymer compounds include DISPERBYK series manufactured by Big Chemie, Solspers series manufactured by Lubrizol, and EFKA-PX series manufactured by BASF. These polymer compounds may be used alone or in combination of two or more, if necessary.

When the non-polymerizable polymer dispersant (A-2) is prepared by itself, the polyamine shown above is synthesized by using a known method for producing a block polymer. Specific examples of the monomer having a tertiary amino group and an ethylenically unsaturated group include dimethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylate, dimethylaminobutyl (meth) acrylate, diethylaminoethyl (meth) acrylate, and the like. Diethylaminopropyl (meth) acrylate, diethylaminobutyl (meth) acrylate, pentamethylpiperidyl (meth) acrylate, tetramethylpiperidyl (meth) acrylate, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, Examples thereof include (meth) acrylamides such as N-isopropyl (meth) acrylamide, dimethylaminoethyl (meth) acrylamide, dimethylaminopropyl (meth) acrylamide, diacetone (meth) acrylamide, and acryloylmorpholin. These monomers may be used alone or in combination of two or more.
Specific examples of the monomer having a quaternary ammonium cation group and an ethylenically unsaturated group include an organic halogen compound salt of the monomer having a tertiary amino group and an ethylenically unsaturated group. The organic halogen compound salt is not particularly limited, but from the viewpoint of availability, specific examples thereof include methyl chloride, ethyl chloride, propyl chloride, butyl chloride, benzyl chloride, ethyl alcohol chloride, methyl bromide, and ethyl bromide. , Propyl bromide, butyl bromide, benzyl bromide, ethyl bromide alcohol, methyl iodide, ethyl iodide, propyl iodide, butyl iodide, benzyl iodide, ethyl iodide alcohol and the like. To introduce a quaternary ammonium cation group, block-polymerize a monomer having a tertiary amino group and another monomer having an ethylenically unsaturated group without using the above-mentioned monomer, and then use a tertiary amine as an organic halogen compound salt. It may be introduced by adding it to a quaternary amine in the presence of a catalyst at an arbitrary temperature and replacing a part or all of the tertiary amine with a quaternary ammonium cation group.
On the other hand, examples of the monomer having an ethylenically unsaturated group whose affinity with other pigment dispersion compositions can be enhanced include an alkyl group, an aryl group, an aralkyl group, a cycloalkyl group, an alkylene glycol group and the like (as an example). Meta) acrylate can be mentioned, but there is no particular limitation as long as it does not impair the affinity with other pigment dispersion compositions. Specific examples include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, and t-butyl (meth) acrylate. ) Acrylate, 2-ethylhexyl (meth) acrylate, cyclohexyl (meth) acrylate, stearyl (meth) acrylate, lauryl (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, isobornyl (meth) acrylate, phenyl (meth) acrylate, benzyl (Meta) acrylates such as (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, methoxypolypropylene glycol (meth) acrylate, or ethoxypolyethylene glycol (meth) acrylate; styrene or α-methylstyrene and the like. Styrenes; vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, or isobutyl vinyl ether; fatty acid vinyls such as vinyl acetate or vinyl propionate. These monomers may be used alone or in combination of two or more.

In the polymer dispersant (A) in the present embodiment, the content ratio of the polymerizable polymer dispersant (A-1) and the non-polymerizable polymer dispersant (A-2) contained in the polymer dispersant (A). The (mass ratio) is preferably (A-1) / (A-2) = 1/99 to 80/20. Any ratio may be taken within this range, but from the viewpoint of storage stability of the pigment dispersion composition, it is preferably in the range of 5/95 to 50/50, more preferably 10/90 to 40/60. Is within the range of. When the polymerizable polymer dispersant (A-1) is 10% by mass or more, the heat resistance, solvent resistance, and pattern adhesion of the colored pattern can be improved. The higher the ratio of (A-1), the more heat resistance, solvent resistance, and pattern adhesion of the desired coloring pattern can be imparted. On the other hand, by setting the ratio of (A-1) to 80% by mass or less and containing the ratio of (A-2) to 20% by mass or more, the desired pigment dispersibility and storage stability of the pigment dispersion composition are ensured. Can be done. As a result, it is possible to provide the polymer dispersant (A) having both desired various performances.

The unsaturated group equivalent of the entire polymer dispersant (A) in the present embodiment is not particularly limited, but a suitable unsaturated group equivalent of the polymerizable polymer dispersant (A-1) and a polymerizable polymer dispersant ( Based on the preferable ratio of A-1) and the non-polymerizable polymer dispersant (A-2), it is preferably 2000 g / mol or more and 20000 g / mol or less, and more preferably 3000 g / mol or more and 10000 g / mol or less. When the unsaturated group equivalent of the entire polymer dispersant (A) is 20000 g / mol or less, it is possible to provide the polymer dispersant (A) having improved heat resistance, solvent resistance and pattern adhesion of the coloring pattern. can. If it is 2000 g / mol or more, the storage stability of the pigment dispersion composition is not impaired.

The content of the polymer dispersant (A) in the pigment dispersion composition is preferably 10 to 80 parts by mass, preferably 12 to 60 parts by mass with respect to 100 parts by mass of the pigment (B) described later. It is more preferably 15 to 40 parts by mass, further preferably 15 to 40 parts by mass.

[Pigment (B)]
The pigment (B) in the present embodiment is not particularly limited as long as it can be uniformly dispersed with other compositions to form the pixels of the color filter. Pigments of each color such as pigments of the three primary colors of light such as red, green and blue, pigments such as yellow, orange and purple that can be used as complementary colors, and pigments such as black and brown used in the black matrix can be used. can. The chemical structure of the pigment (B) includes isoindoleinone, isoindoline, azomethin, anthraquinone, antron, xanthene, diketopyrrolopyrrole, perylene, perinone, quinacridone, indigoid, dioxazine, indigoid, phthalocyanine, anthocyanine, and azo. All organic pigments such as; inorganic pigments such as carbon black, titanium black, titanium dioxide and the like.

Above all, the pigment (B) in the present embodiment preferably contains a green pigment having a halogenated phthalocyanine skeleton represented by the following formula (1).

In formula (1), M represents a divalent or tetravalent metal atom. From the viewpoint of color reproducibility, zinc or copper is preferable, and zinc is particularly preferable. X represents any one of a hydrogen atom, a chlorine atom and a bromine atom, and contains at least one chlorine atom or a bromine atom. The addition ratio of chlorine atom and bromine atom changes according to the brightness and color reproducibility. The more chlorine atom and less bromine atom, the higher the brightness, and conversely, the more bromine atom and less chlorine atom, the better the color reproducibility tends to be. be. The chlorine atom is preferably 1 or more and 10 or less, and more preferably 1.5 or more and 8 or less. The number of bromine atoms is preferably 5 or more and 15 or less, and more preferably 7 or more and 14 or less.

By using a green pigment having a halogenated phthalocyanine skeleton and the polymer dispersant (A), sufficient pigment dispersibility and storage stability of the pigment dispersion composition can be obtained. As a result, it is possible to provide a color filter having high brightness and a wide color reproduction range. At the same time, it is possible to impart heat resistance, solvent resistance, and pattern adhesion of the colored pattern.

As the halogenated phthalocyanine pigment, a commercially available product may be used, or the pigment may be prepared by itself. As an example of a commercially available product, C.I. I. Pigment Green 7, 36, 58, 59, etc., among which C.I. I. The use of Pigment Greens 58 and 59 is preferred.
When preparing by yourself, use a known manufacturing method. For example, a method of forming a phthalocyanine skeleton under a catalyst such as ammonium molybdate using phthaloic acid, phthalonitrile, or the like in which a part or all of hydrogen atoms of the aromatic ring is substituted with a halogen atom as a starting material can be mentioned. Further, a method of halogenating phthalocyanine with chlorine gas or bromine gas can be mentioned. A desired green pigment can be obtained by dry-grinding the crude pigment obtained by these methods in a pulverizer such as a ball mill or a vibration mill and treating with a known solvent salt milling method or the like.

Regarding the pigment (B) in the present embodiment, the green pigment having a halogenated phthalocyanine skeleton may be used alone or in combination of two or more. Further, other pigments other than the green pigment having a halogenated phthalocyanine skeleton may be used in combination.
Specific examples of other pigments include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, 137, 138, 139, Yellow pigments such as 147, 148, 150, 153, 154, 166, 173, 194, 214; C.I. I. Pigment Orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73 and the like; C.I. I. Pigment Red 9, 97, 105, 122, 123, 144, 149, 166, 168, 176, 177, 180, 192, 209, 215, 216, 224, 242, 254, 255, 264, 265 and other red pigments; C. I. Pigment Blue 15, 15: 3, 15: 4, 15: 6, 60 and other blue pigments; C.I. I. Pigment Violet 1, 19, 23, 29, 32, 36, 38 and other purple pigments; C.I. I. Pigment Brown 23, 25 and other brown pigments; C.I. I. Pigment Blacks 1 and 7, carbon black, titanium black, black pigments such as iron oxide and the like can be mentioned. These pigments may be used alone or in combination of two or more, depending on the color of the target pixel.

Further, regarding the pigment (B) in the present embodiment, not only the pigment but also a dye may be used in combination. When a dye is used in combination, higher brightness, a wider color reproduction range, and better developability can be expected as compared with the case where a pigment is used. On the other hand, when a pigment is used in combination, the heat resistance is superior to that of a dye, and the color change after forming a coloring pattern is small. Dyes and pigments may be used in combination depending on the required performance and the target pixel color.

The dyes include acid dyes having an acidic group such as a carboxy group and acid dyes from the viewpoints of solubility in the solvent (C) and an alkaline developing solution, interaction with other components in the resin composition, heat resistance, and the like. It is preferable to use a salt with a nitrogen compound, a sulfonamide of an acid dye, or the like. Specific examples of such dyes include acid alizarin violet N; acid black1, 2, 24, 48; acid blue1, 7, 9, 25, 29, 40, 45, 62, 70, 74, 80, 83, 90. , 92, 112, 113, 120, 129, 147; acid chrome violet K; acid fuchsin; acid green1, 3, 5, 25, 27, 50; acid orange 6, 7, 8, 10, 12, 50, 51, 52 , 56, 63, 74, 95; acid red1, 4, 8, 14, 17, 18, 26, 27, 29, 31, 34, 35, 37, 42, 44, 50, 51, 52, 57, 69, 73, 80, 87, 88, 91, 92, 94, 97, 103, 111, 114, 129, 133, 134, 138, 143, 145, 150, 151, 158, 176, 183, 198, 211, 215, 216, 217, 249, 252, 257, 260, 266, 274; acid violet 6B, 7, 9, 17, 19; acid chrome 1, 3, 9, 11, 17, 23, 25, 29, 34, 36, 42. , 54, 72, 73, 76, 79, 98, 99, 111, 112, 114, 116; hood hello 3 and derivatives thereof and the like. Among these, azo-based, xanthene-based, anthraquinone-based or phthalocyanine-based acid dyes are preferable. These dyes may be used alone or in combination of two or more.

<Solvent (C-1)>
The solvent (C-1) is not particularly limited as long as it is a solvent that does not react with each component contained in the pigment dispersion composition of the present embodiment or the photosensitive coloring composition and can dissolve or disperse them. As the solvent (C-1), the same solvent as that used for producing the polymer dispersant (A) can be used, and the solvent contained after the reaction can be used as it is, and further added. You can also. Further, when other components are added, they may coexist there. Specific examples of the solvent (C-1) include propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, dipropylene glycol monomethyl ether acetate, ethyl acetate, butyl acetate, isopropyl acetate, propylene glycol monomethyl ether, and dipropylene glycol monomethyl ether. Examples thereof include tripropylene glycol monomethyl ether, ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, ethylene glycol monoethyl ether acetate and diethylene glycol ethyl ether acetate. These may be used alone or in combination of two or more. Among these, glycol ether solvents such as propylene glycol monomethyl ether and propylene glycol monomethyl ether acetate, which are preferably used in the production of color filters, are preferable.

<Binder resin (D-1)>
The binder resin (D-1) is not particularly limited, but resins such as (meth) acrylic resin, epoxy (meth) acrylic resin, and vinyl ester resin generally used for negative resists are preferable. Further, a resin containing an ethylenically unsaturated double bond such as a vinyl group and a (meth) acryloyl group and a substituent contributing to alkali solubility such as a carboxylic acid, a phosphoric acid and a sulfonic acid is preferable. By using these resins, it is possible to provide a photosensitive coloring composition having excellent pattern adhesion and developability. The above-mentioned polymer dispersants (A-1) and (A-2) do not correspond to the binder resin.

Among these resins, it is preferable to use a (meth) acrylic resin having a (meth) acryloyl group and a carboxy group, particularly from the viewpoint of easily providing a resin having a wide range of properties. This resin may be a commercially available product or may be prepared by itself. In the case of self-preparation, one or more kinds of polymerizable monomers in the art are polymerized by a radical polymerization method known in the art, and then a (meth) acryloyl group and / or a carboxylic acid is added to the base polymer. This makes it possible to synthesize the binder resin (D-1).
As a method for adding a (meth) acryloyl group, a base polymer is polymerized using a polymerizable monomer having a reactive group such as a hydroxy group, an amino group, a carboxy group, an epoxy group, or an isocyanato group, and then a polymerization inhibitor and a catalyst. After that, a (meth) acryloyl group-containing monomer having a functional group capable of binding to these reactive groups is added, and the reaction is carried out under the condition of 50 to 150 ° C. Moreover, the following method is mentioned as a method of adding a carboxy group.
A method of reacting a base polymer having a hydroxy group with a polybasic acid anhydride such as succinic anhydride to generate a carboxy group.
A method of reacting a base polymer having a carboxy group with a (meth) acryloyl group-containing monomer having an epoxy group and then reacting with a polybasic acid anhydride such as succinic anhydride to generate a carboxy group.
A method in which a (meth) acryloyl group-containing monomer having a carboxy group is reacted with a base polymer having an epoxy group, and then a polybasic acid anhydride such as succinic anhydride is reacted to generate a carboxylic acid.
Alternatively, a method of retaining the carboxy group in the base polymer can be mentioned.
The solvent (C-1) contained in the pigment dispersion composition may be added in order to appropriately control the molecular weight during the synthesis and to appropriately adjust the viscosity after the synthesis.

The physical properties of the binder resin (D-1) are not particularly limited, but from the viewpoint of ease of production of the photosensitive coloring composition and compatibility with other compositions, the weight average molecular weight: 1000 to 50,000, solid. The acid fraction is preferably in the range of 10 to 200 mgKOH / mg, unsaturated group equivalent: 100 to 3000 g / mol, and viscosity: 0.1 to 1000 dPa · s.

When the pigment dispersion composition of the present embodiment contains the binder resin (D-1), the content is preferably 10 to 80 parts by mass, preferably 12 to 80 parts by mass with respect to 100 parts by mass of the pigment (B). It is more preferably 50 parts by mass, and even more preferably 15 to 40 parts by mass.

<Photosensitive coloring composition>
The photosensitive coloring composition of the present embodiment contains the pigment dispersion composition, a binder resin (D-2), a reactive diluent (E), and a photopolymerization initiator (F). The photosensitive coloring composition of the present embodiment may contain a solvent (C-2). In the photosensitive coloring composition of the present embodiment, the total amount of the binder resin (D) of the binder resin (D-1) and (D-2) is 50 to 280 parts by mass with respect to 100 parts by mass of the pigment (B). , 40 to 200 parts by mass of the reactive diluent (E) and 0.1 to 10 parts by mass of the photopolymerization initiator (F) are preferable.
As the solvent (C-2), the same solvent as the solvent (C-1) contained in the pigment dispersion composition may be used, or a different solvent may be added.

<Binder resin (D-2)>
The binder resin (D-2) may be the same as or different from the binder resin (D-1) contained in the pigment dispersion composition.
The total content of the binder resin (D) of the binder resin (D-1) and (D-2) is preferably 50 to 280 parts by mass with respect to 100 parts by mass of the pigment (B), 75. It is more preferably to 230 parts by mass, and further preferably 100 to 200 parts by mass.

<Reactive diluent (E)>
The reactive diluent (E) is not particularly limited as long as it is a low molecular weight compound containing an ethylenically unsaturated double bond such as a vinyl group and a (meth) acryloyloxy group. Specific examples of the reactive diluent (C) include aromatic vinyl-based monomers such as styrene, α-methylstyrene, α-chloromethylstyrene, vinyltoluene, divinylbenzene, diallylphthalate, and diallylbenzenephosphonate; vinyl acetate, Polycarboxylic acid monomers such as vinyl adipine; methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, butyl (meth) acrylate, β-hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate , Ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, ethylene glycol di (meth) acrylate, trimerol propanedi (meth) acrylate, trimerol propanetri (meth) acrylate, Examples thereof include (meth) acrylic monomers such as pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and tri (meth) acrylate of tris (hydroxyethyl) isocyanurate; triallyl cyanurate and the like. These may be used alone or in combination of two or more. Among these, compounds having a plurality of (meth) acryloyloxy groups are preferable, and trimethylolpropane tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, and tris (hydroxyethyl) isocyanurate. A compound having three or more (meth) acryloyloxy groups, such as tri (meth) acrylate, is more preferable.

The content of the reactive diluent (E) is preferably 40 to 200 parts by mass, more preferably 60 to 180 parts by mass, and 80 to 160 parts by mass with respect to 100 parts by mass of the pigment (B). It is more preferable to be a part.

<Photopolymerization initiator (F)>
The photopolymerization initiator (F) is preferably a photoradical generator, and specific examples thereof include benzophens such as benzoin, benzoin methyl ether, and benzoin ethyl ether and their alkyl ethers; acetophenone, 2,2-dimethoxy-2-phenyl. Acetophenones such as acetophenone, 1,1-dichloroacetophenone, 4- (1-t-butyldioxy-1-methylethyl) acetophenone; 2-methylanthraquinone, 2-amylanthraquinone, 2-t-butylanthraquinone, 1-chloroanthraquinone And other anthraquinones; thioxanthones such as 2,4-dimethylthioxanthone, 2,4-diisopropylthioxanthone, 2-chlorothioxanthone; ketals such as acetophenone dimethyl ketal, benzyl dimethyl ketal; benzophenone, 4- (1-t-butyldioxy). Benzophenones such as -1-methylethyl) benzophenone, 3,3', 4,4'-tetrakis (t-butyldioxycarbonyl) benzophenone; 2-methyl-1- [4- (methylthio) phenyl] -2- Examples thereof include morpholino-propane-1-one; 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butanone-1; acylphosphine oxides; and xanthones. These may be used alone or in combination of two or more.

The content of the photopolymerization initiator (F) is preferably 0.1 to 10 parts by mass, more preferably 1 to 9 parts by mass, and 2 to 2 to 9 parts by mass with respect to 100 parts by mass of the pigment (B). It is more preferably 8 parts by mass.

In addition to the above components, the photosensitive coloring composition of the present embodiment has known additives and fillers such as a photoacid generator, a photobase generator, a coupling agent, and a leveling agent in order to impart predetermined properties. Etc. may be blended. The blending amount of these components is not particularly limited as long as it does not impair the effects of the present invention.

<Manufacturing method of pigment dispersion composition>
In the pigment dispersion composition of the present embodiment, a predetermined amount of a polymer dispersant (A), a pigment (B), a solvent (C-1) and a binder resin (D-1) as an optional component is weighed, and a known dispersion treatment is performed. The pigment (B) is refined and dispersed using a step. In this dispersion processing step, devices such as a paint shaker, a bead mill, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, a planetary mixer, and a rotation / revolution mixer are often used. Further, in this dispersion treatment step, if beads having a diameter of 0.01 to 10 mm are used, uniform miniaturization of the pigment (B) can be efficiently performed. Although the material of the beads is not limited, it is preferable to use glass beads or zirconia beads in consideration of hardness, contamination with the pigment dispersion composition, and the like. Appropriate conditions for the suitable time, temperature, bead diameter, and amount used for the dispersion treatment differ depending on the composition of the pigment dispersion composition, the size of the apparatus, and the like, and may be appropriately adjusted.
Finally, it is preferable to filter the pigment dispersion composition with a glass filter or the like for the purpose of removing fine dust and coarse particles and aggregates of the pigment (B) from the pigment dispersion composition.

<Manufacturing method of photosensitive coloring composition>
The photosensitive coloring composition of the present embodiment can be produced by mixing each of the above components using a known mixing device. For example, it can be produced by first preparing a pigment dispersion composition and then mixing a binder resin (D-2), a reactive diluent (E), a photopolymerization initiator (F), and the like in this order. Further, if necessary, a solvent (C-2) may be added in addition to the solvent (C-1) contained in the pigment dispersion composition. In that case, the solvent (C) contained in the photosensitive coloring composition contains the solvent (C-1) and the solvent (C-2). The solvent (C-2) may be the same as that of the solvent (C-1), or may be different from the solvent (C-1).

The photosensitive coloring composition obtained as described above has sufficient pigment dispersibility and storage stability of the pigment dispersion composition, can achieve high luminance, and is excellent in suppressing bleed-out of the colorant. Various resist properties such as heat resistance, solvent resistance, pattern adhesion, and developability can be exhibited. As a result, a highly reliable coloring pattern can be formed. That is, by using the photosensitive coloring composition, it is possible to provide a highly reliable color filter.

<Color filter>
Next, a color filter having a coloring pattern made of a cured product of the photosensitive coloring composition of the present invention will be described. The color filter of the present invention has a coloring pattern formed by using the above-mentioned photosensitive coloring composition. The color filter is usually composed of a substrate, RGB pixels formed on the substrate, a black matrix formed at the boundary of each pixel, and a protective film formed on the pixels and the black matrix. In this configuration, known configurations can be adopted except that the pixels and the black matrix (coloring pattern) are formed by using the above-mentioned photosensitive coloring composition.

Next, an embodiment of a method for manufacturing a color filter will be described. First, a coloring pattern is formed on the substrate. Specifically, a black matrix and RGB pixels are sequentially formed on the substrate. The material of the substrate is not particularly limited, and a glass substrate, a silicon substrate, a polycarbonate substrate, a polyester substrate, a polyamide substrate, a polyamide-imide substrate, a polyimide substrate, an aluminum substrate, a printed wiring board, an array substrate, or the like may be appropriately used. can.

The coloring pattern can be formed by a photolithography method. Specifically, after the above-mentioned photosensitive coloring composition is applied onto a substrate to form a coating film, the coating film is exposed through a photomask having a predetermined pattern to photo-cure the exposed portion. Then, the unexposed portion is developed with an alkaline aqueous solution and then baked to form a predetermined coloring pattern.

The method for applying the photosensitive coloring composition is not particularly limited, but a screen printing method, a roll coating method, a curtain coating method, a spray coating method, a spin coating method, or the like can be used. Further, after the photosensitive coloring composition is applied, the solvent (C) may be volatilized by heating using a heating means such as a circulating oven, an infrared heater, or a hot plate, if necessary. The heating conditions are not particularly limited and may be appropriately set according to the type of the photosensitive coloring composition used. Generally, it may be heated at a temperature of 50 ° C. to 120 ° C. for 30 seconds to 30 minutes.

Next, the formed coating film is partially exposed by irradiating it with active energy rays such as ultraviolet rays and excimer laser light through a negative mask. The energy dose to be irradiated may be appropriately selected depending on the composition of the photosensitive coloring composition, and is preferably 30 to 2000 mJ / cm ² , for example. The light source used for exposure is not particularly limited, but a low-pressure mercury lamp, a medium-pressure mercury lamp, a high-pressure mercury lamp, a xenon lamp, a metal halide lamp, or the like can be used.

The alkaline aqueous solution used for development is not particularly limited, but is an aqueous solution of sodium carbonate, potassium carbonate, calcium carbonate, sodium hydroxide, potassium hydroxide or the like; an amino group system such as an ethylamino group, a diethylamino group or a dimethylethanolamino group. Aqueous compound; tetramethylammonium, 3-methyl-4-amino-N, N-diethylaniline, 3-methyl-4-amino-N-ethyl-N-β-hydroxyethylaniline, 3-methyl-4-amino -N-ethyl-N-β-methanesulfonamide ethylaniline, 3-methyl-4-amino-N-ethyl-N-β-methoxyethylaniline and sulfates, hydrochlorides or p-toluenesulfonates thereof, etc. An aqueous solution of the p-phenylenediamino group compound of the above can be used. A defoaming agent or a surfactant may be added to these aqueous solutions as needed. Further, it is preferable to wash with water and dry after developing with the above alkaline aqueous solution.

The baking conditions are not particularly limited, and the heat treatment may be performed according to the type of the photosensitive coloring composition used. Generally, it may be heated at 130 to 250 ° C. for 10 to 60 minutes.

The above coating, exposure, development and baking are sequentially repeated using the photosensitive coloring composition for black matrix and the photosensitive coloring composition for red, green and blue pixels to obtain a desired coloring pattern. Can be formed. After that, a protective film is formed on the colored pattern (each pixel of RGB and the black matrix), but the protective film is not particularly limited and may be formed by using a known one.

The color filter manufactured in this way has excellent pigment dispersibility by realizing uniform miniaturization of the pigment, achieves high brightness, suppresses bleed-out of the colorant, and has excellent heat resistance and resistance. Has solvent properties and adhesion.

<Image display element>
The image display element of the present embodiment is an image display element provided with the above color filter, and specific examples thereof include a liquid crystal display element, an organic EL display element, a solid-state image pickup element such as a CCD element and a CMOS element, and the like. .. The image display element of the present embodiment may be manufactured according to a conventional method other than using the above color filter. For example, in the case of manufacturing a liquid crystal display element, the color filter is formed on a substrate, and then electrodes, spacers, and the like are sequentially formed. Then, an electrode or the like may be formed on another substrate, the two may be bonded together, and a predetermined amount of liquid crystal may be injected and sealed.

Hereinafter, the present invention will be described in detail with reference to Examples, but the present invention is not limited to these Examples. In this embodiment, parts and percentages are all based on mass unless otherwise specified.

<Measurement method of weight average molecular weight>
The weight average molecular weight described below means a standard polystyrene-equivalent weight average molecular weight measured under the following conditions using gel permeation chromatography (GPC).
Column: Showdex (registered trademark) LF-804 + LF-804 (manufactured by Showa Denko KK)
Column temperature: 40 ° C
Sample: 0.2% Tetrahydrofuran solution of the object to be measured Developing solvent: Tetrahydrofuran Detector: Differential refractometer (SHODEX RI-71S) (manufactured by Showa Denko KK)
Flow velocity: 1 mL / min

<Measuring method of amine value of polymerizable polymer dispersant (A-1)>
The amine value of the polymerizable polymer dispersant (A-1) excluding the solvent, which is the amine value of the catalog value of the polymer compound (a), and the polymer compound (a) and the ethylenically unsaturated monomer ( It is a calculated value calculated based on the usage amount of b).

<Measuring method of amine value of non-polymerizable polymer dispersant (A-2)>
It is the mass of the non-polymerizable polymer dispersant (A-2) per number of moles of the tertiary amino group and the quaternary ammonium cation group, and is a calculated value calculated based on the amount of the monomer used. The calculation follows the definition of amine value (value measured according to the standard shown in JIS K7237 etc.) and neutralizes the amine component contained in 1 g of the solid content of the non-polymerizable polymer dispersant (A-2). It was expressed as the number of mg of potassium hydroxide required for this.

<Measuring method of unsaturated group equivalent of polymerizable polymer dispersant (A-1)>
It is the mass of the solid content of the polymerizable polymer dispersant (A-1) excluding the solvent per number of moles of the ethylenically unsaturated group, and is the actual polymer compound (a) and the ethylenically unsaturated monomer ( It is a calculated value calculated based on the usage amount of b).

An example of production of the polymerizable polymer dispersant (A-1) is shown below.

<Synthesis example 1>
In a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, the raw material No. 1 was used as the polymer compound (a). As 1, Polyment NK-380 (manufactured by Nippon Catalyst Co., Ltd., solid content 30%, amine value 56 mgKOH / g, weight average molecular weight 100,000, primary and secondary amino group-containing dispersants) was 86.7 g, ethylenically unsaturated single amount. 3.7 g of glycidyl methacrylate as the body (b) (1.0 equivalent to 1.0 equivalent of the total amino group amount of the polymer compound (a)) and 89 mg of 4-methoxyphenol as a polymerization inhibitor (polymer compound (polymer compound (a)). 0.3 part) was added to 100 parts of the solid content of a) and the ethylenically unsaturated monomer (b), and the inside of the flask was stirred while being replaced with dry air, and the temperature was raised from room temperature to 120 ° C. The mixture was stirred until the disappearance of the epoxy group of glycidyl methacrylate was confirmed by the NMR spectrum. Then, the temperature was lowered to room temperature, and 8.6 g of propylene glycol monomethyl ether acetate was added as a solvent to prepare the solid content (total amount of components excluding the solvent) to be 30%, and the polymerizable polymer dispersant (A-1) was prepared. As sample No. I got 1.

<Synthesis example 2>
Polymerization was carried out according to the same method as in Synthesis Example 1 except that glycidyl methacrylate was added as an ethylenically unsaturated monomer (b) in an amount of 0.6 equivalent to 1.0 equivalent of the total amino group amount of the polymer compound (a). Sample No. as the sex polymer dispersant (A-1). I got 2.

<Synthesis example 3>
Polymerization was carried out according to the same method as in Synthesis Example 1 except that glycidyl methacrylate was added as an ethylenically unsaturated monomer (b) in an amount of 0.3 equivalent to 1.0 equivalent of the total amino group amount of the polymer compound (a). Sample No. as the sex polymer dispersant (A-1). I got 3.

<Synthesis example 4>
Similar to Synthesis Example 1 except that 4-hydroxybutyl acrylate glycidyl ether was added as the ethylenically unsaturated monomer (b) in an amount of 0.3 equivalent to 1.0 equivalent of the total amino group amount of the polymer compound (a). As the polymerizable polymer dispersant (A-1), the sample No. I got 4.

<Synthesis Example 5>
In a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, the raw material No. 1 was used as the polymer compound (a). As 2, 74.3 g of Polyment NK-350 (manufactured by Nippon Catalyst Co., Ltd., solid content 35%, amine value 45 mgKOH / g, weight average molecular weight 100,000, primary amino group-containing dispersant), ethylenically unsaturated monomer (b) ), 0.9 g of glycidyl methacrylate (0.3 equivalents based on 1.0 equivalent of the total amino group of the polymer compound (a)), 81 mg of 4-methoxyphenol as a polymerization inhibitor (polymer compound (a) and 0.3 part) was added to 100 parts of the solid content of the ethylenically unsaturated monomer (b), and the inside of the flask was stirred while being replaced with dry air, and the temperature was raised from room temperature to 120 ° C. The mixture was stirred until the disappearance of the epoxy group of glycidyl methacrylate was confirmed by the NMR spectrum. Then, the temperature was lowered to room temperature, 14.5 g of propylene glycol monomethyl ether acetate was added as a solvent to prepare the solid content to 30%, and the sample No. was used as a polymerizable polymer dispersant (A-1). I got 5.

<Synthesis example 6>
As the polymer compound (a), the raw material No. Same as Synthesis Example 5 except that Polyment NK-100PM (manufactured by Nippon Catalyst Co., Ltd., solid content 49%, amine value 143 mgKOH / g, weight average molecular weight 20000, primary and secondary amino group-containing dispersants) was added as 3. As the polymerizable polymer dispersant (A-1), the sample No. I got 6.

<Comparative synthesis example 1>
In a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, the raw material No. 1 was used as the polymer compound (a). As 1, Polyment NK-380 (manufactured by Nippon Catalyst Co., Ltd., solid content 30%, amine value 56 mgKOH / g, weight average molecular weight 100,000) was 86.7 g, and methacryloyl chloride as an ethylenically unsaturated monomer (b) was 4.5 g. (1.0 equivalent to 1.0 equivalent of the total amino group amount of the polymer compound (a)), 92 mg of 4-methoxyphenol as a polymerization inhibitor (polymer compound (a) and ethylenically unsaturated monomer (polymer compound (a)) and ethylenically unsaturated monomer ( 0.3 part) was added to 100 parts of the solid content of b). The inside of the flask was stirred while being replaced with dry air, and the mixture was stirred at room temperature until the disappearance of the acid chloride was confirmed by IR spectra. Then, 10.5 g of propylene glycol monomethyl ether acetate was added as a solvent to prepare the solid content to 30%, and the amino group to which the ethylenically unsaturated monomer (b) was added became an amide as a polymer dispersant. , Sample No. I got 7.

<Comparative synthesis example 2>
6.2 g of 2-isocyanatoethylacryllate (1.0 equivalent to 1.0 equivalent of the total amino group of the polymer compound (a)) was added as the ethylenically unsaturated monomer (b) at room temperature. As a polymer dispersant in which the amino group to which the ethylenically unsaturated monomer (b) is added becomes urea according to the same method as in Comparative Synthesis Example 1 except that the mixture was stirred until the disappearance of the isocyanato group was confirmed by the IR spectrum. , Sample No. I got 8.

<Comparative synthesis example 3>
Instead of the ethylenically unsaturated monomer (b), 3.0 g of glycidyl isopropyl ether having no ethylenically unsaturated group (1.0 equivalent with respect to 1.0 equivalent of the total amino group amount of the polymer compound (a)). ) Was added, and the sample No. 1 was used as the polymer dispersant according to the same method as in Synthesis Example 1. I got 9.

Types of polymer compounds (a) and ethylenically unsaturated monomers (b) of Synthesis Examples 1 to 6 and Comparative Synthesis Examples 1 to 3, polymer compounds (a) of ethylenically unsaturated monomers (b) The input amount with respect to the total amino group amount of 1.0 equivalent, and the sample No. Table 1 shows the amine values of 1 to 9, the unsaturated group equivalent, and the weight average molecular weight.

An example of production of the non-polymerizable polymer dispersant (A-2) is shown below.

<Synthesis example 7>
In a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, 133 g of propylene glycol monomethyl ether acetate, 80.5 g of isobornyl methacrylate and 13.2 g of tetramethylethylenediamine as a catalyst were placed in the flask. The inside was stirred at 50 ° C. for 1 hour while replacing the inside with nitrogen. Then, 9.3 g of ethyl bromoisobutyrate and 5.6 g of cuprous chloride were added as catalysts, the temperature of the flask was raised to 110 ° C., and then the polymerization reaction was carried out for 4 hours. After the reaction, the solution was sampled to measure the non-volatile content, and after confirming that the polymerization conversion was 98% or more in terms of the non-volatile content, 61 g of propylene glycol monomethyl ether acetate and a monomer having a tertiary amino group were used. 5 g of dimethylaminoethyl methacrylate was added, and the reaction was further carried out at 110 ° C. for 2 hours. After the reaction, the solution was sampled again to measure the non-volatile content, converted from the non-volatile content, and after confirming that the polymerization conversion rate was 98% or more, the solution was cooled. Finally, propylene glycol monomethyl ether acetate was added as a solvent so that the solid content was 40.0%, and the sample No. was used as a solution of the non-heavy synthetic polymer dispersant (A-2) having a tertiary amino group. 10 (amine value 70 mgKOH / g, weight average molecular weight 5500) was obtained.

<Synthesis Example 8>
In a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, 133 g of propylene glycol monomethyl ether acetate, 70.0 g of isobornyl methacrylate and 13.2 g of tetramethylethylenediamine as a catalyst were placed in the flask. The inside was stirred at 50 ° C. for 1 hour while replacing the inside with nitrogen. Then, 9.3 g of ethyl bromoisobutyrate and 5.6 g of cuprous chloride were added as catalysts, the temperature of the flask was raised to 110 ° C., and then the polymerization reaction was carried out for 4 hours. After the reaction, the solution was sampled to measure the non-volatile content, and after confirming that the polymerization conversion was 98% or more in terms of the non-volatile content, 61 g of propylene glycol monomethyl ether acetate and quaternary ammonium cation group were used as a monomer 30. .0 g of methacryloyloxyethylbenzyldimethylammonium chloride was added, and the reaction was further carried out at 110 ° C. for 2 hours. After the reaction, the solution was sampled again to measure the non-volatile content, converted from the non-volatile content, and after confirming that the polymerization conversion rate was 98% or more, the solution was cooled. Finally, propylene glycol monomethyl ether acetate is added as a solvent so that the solid content is 40.0%, and the sample No. becomes a solution of the non-polymerizable polymer dispersant (A-2) having a quaternary ammonium cationic group. .. 11 (amine value 60 mgKOH / g, weight average molecular weight 5000) was obtained.

An example of manufacturing the binder resin (D-1) or (D-2) is shown below.

<Synthesis example 9>
After putting 67.2 g of propylene glycol monomethyl ether acetate in a flask equipped with a stirrer, a dropping funnel, a condenser, a thermometer and a gas introduction tube, the mixture was stirred while being replaced with nitrogen gas, and the temperature was raised to 120 ° C. Next, 8.0 g of t-butylperoxy-2-ethylhexa as a polymerization initiator was added to a monomer mixture consisting of 16.2 g of dicyclopentanyl methacrylate, 51.8 g of benzyl methacrylate and 26.5 g of acrylic acid. The product to which the monomer was added was dropped from the dropping funnel into the flask. After completion of the dropping, the copolymerization reaction was carried out by stirring at 120 ° C. for 2 hours.
Next, after replacing the inside of the flask with dry air, 15.7 g of glycidyl methacrylate, 0.3 g of triphenylphosphine as a catalyst and 0.2 g of hydroquinone monomethyl ether as a polymerization inhibitor were added, and the temperature was 120 ° C. for 5 hours. The reaction was carried out. Then, 74.8 g of propylene glycol monomethyl ether acetate was added as a solvent to prepare the solid content to 40%. As the binder resin (D-1) or (D-2) having an ethylenically unsaturated double bond and a carboxylic acid as alkali-soluble, the sample No. 12 (solid acid value 135 mgKOH / g, unsaturated group equivalent 1100 g / mol, weight average molecular weight 10000) were obtained.

<Synthesis Example 10>
To a monomer mixture consisting of 11.9 g of dicyclopentanyl methacrylate, 42.7 g of benzyl methacrylate and 20.9 g of methacrylic acid, 1.6 g of t-butylperoxy-2-ethylhexanoate as a polymerization initiator was added. After the copolymerization reaction was carried out by adding the sample, the sample was prepared as a binder resin (D-1) or (D-2) according to the same method as in Synthesis Example 8 except that 11.5 g of glycidyl methacrylate was added and the reaction was carried out. No. 13 (solid acid value 104 mgKOH / g, unsaturated group equivalent 1100 g / mol, weight average molecular weight 32000) was obtained.

An example of manufacturing a pigment dispersion composition is shown below.

<Examples 1 to 11 and Comparative Examples 1 to 10>
C.I. I. Pigment Green 58 (Fastogen Green A110 manufactured by DIC) was used as 7.5 g (100 parts by mass) of the above-mentioned sample No. as a polymerizable polymer dispersant (A-1). 1-9 or raw material No. Sample No. 1 to any one of 1 to 3 having a tertiary amino group as the non-polymerizable polymer dispersant (A-2). Sample No. having a 10 or quaternary ammonium cation group. No. 11 as the binder resin (D-1). 12 was mixed with the composition shown in Table 2. Propylene glycol monomethyl ether acetate was added as a solvent (C-1) to adjust the solid content to 24% excluding zirconia beads, and the mixture was mixed with a paint shaker (Red Devil 5400 manufactured by Red Devil Appliance) at room temperature for 2 hours. And dispersed. Then, the content was suction-filtered with a glass filter to obtain the pigment dispersion composition No. Obtained 1-21.

<Evaluation of pigment dispersibility>
The viscosity of the pigment dispersion composition immediately after preparation was evaluated by measuring with an E-type viscometer (RE-80L manufactured by Toki Sangyo Co., Ltd., measuring temperature 25 ° C.). Further, from the measurement result of the viscosity, the pigment dispersibility and the storage stability of the pigment dispersion composition were evaluated in 4 stages of 1 to 4 according to the following criteria, and 3 or more were accepted. The evaluation results are shown in Table 2.
"4": less than 6.0 mPa · s "3": 6.0 mPa · s or more and less than 10.0 mPa · s "2": 10.0 mPa · s or more "1": no liquidity

<Evaluation of storage stability of pigment dispersion composition>
The viscosity of the pigment dispersion composition after storing the prepared pigment dispersion composition at room temperature for 2 weeks was evaluated by measuring with an E-type viscometer (RE-80L manufactured by Toki Sangyo Co., Ltd., measurement temperature 25 ° C.). The rate of increase in viscosity of the pigment dispersion composition after storage at room temperature for 2 weeks was evaluated on a scale of 1 to 4 according to the following criteria, as compared with immediately after preparation. The evaluation results are shown in Table 2.
"4": less than 10% "3": 10% or more and less than 20% "2": 20% or more "1": the pigment dispersion composition immediately after preparation has no fluidity and cannot be measured.

An example of manufacturing a photosensitive coloring composition is shown below.

<Examples 12 to 22, Comparative Examples 11 to 20>
The pigment dispersion composition No. When the solid content of 1 to 21 (total amount of components other than the solvent) is 100 parts by mass, the sample No. 1 is used as the binder resin (D-2). 80 parts by mass of 13 as a solid content, 80 parts by mass of dipentaerythritol hexaacrylate as a reactive diluent (E), 1- [9-ethyl-6- (2-methylbenzoyl) as a photopolymerization initiator (F)) -9H-carbazole-3-yl-]-, -1- (O-acetyloxime) was mixed in an amount of 4 parts by mass, and propylene glycol monomethyl ether acetate was added as a solvent (C-2) to make the total solid content 30%. By mixing so as to be, the photosensitive coloring composition No. 1 to 21 were prepared. The blending amount of each component with respect to 100 parts by mass of the pigment (B) was 128 parts by mass for the binder resin (D-2), 128 parts by mass for the reactive diluent (E), and 6 parts by mass for the photopolymerization initiator (F). .4 parts by mass.

<Preparation of green resist>
The photosensitive coloring compositions 1 to 21 are spin-coated on a 5 cm square glass substrate (non-alkali glass substrate) so that the average thickness of the final cured coating film is 1.5 μm, and then the temperature is 100 ° C. for 3 minutes. The solvent was volatilized by heating. Next, the entire surface of the coating film is exposed (USH-250BY manufactured by Ushio, Inc. is used as a lamp, the exposure amount is 40 mJ / cm ² ), and then the coating film is further baked at 230 ° C. for 30 minutes to obtain a green coating film. I got a resist.

<Solvent resistance test>
The entire surface of the green resist was immersed in N-methylpyrrolidone at 80 ° C. for 3 minutes. Then, the green resist was taken out and air-dried. The solvent resistance of the photosensitive coloring composition was evaluated by visually confirming the peeling condition of the entire surface of the green resist. From the measurement results, the solvent resistance of the photosensitive coloring composition was evaluated on a scale of 1 to 4 according to the following criteria, and 3 or more was accepted. The evaluation results are shown in Table 3.
"4": Peeled part is less than 5% "3": Peeled part is less than 20% in area ratio "2": Peeled part is 20% or more in area ratio "1": Measurement without fluidity of pigment dispersion composition Impossible

As can be seen from the results of Tables 2 and 3, in Examples 1 to 22, excellent pigment dispersibility and storage stability of the pigment dispersion composition were obtained, and excellent solvent resistance of the photosensitive coloring composition was obtained. Obtained.
On the other hand, in Comparative Examples 1 and 2 and 11 to 12, the pigment dispersity of the pigment dispersion composition was extremely poor, and the pigment dispersion composition could not be used as the pigment dispersion composition and the photosensitive coloring composition. Further, in Comparative Examples 3 to 5 and 13 to 15, peeling of the photosensitive coloring composition was not confirmed and the solvent resistance was good, but the pigment dispersity and storage stability of the pigment dispersion composition were poor. Further, in Comparative Examples 6 to 10 and 16 to 20, the pigment dispersion composition had good pigment dispersibility and storage stability, but peeling of the photosensitive coloring composition was confirmed, and the solvent resistance was poor.

Based on the above, the present invention comprises a pigment dispersion composition having excellent pigment dispersibility and storage stability, a photosensitive coloring composition containing the pigment dispersion composition, and the photosensitive coloring composition thereof, and the solvent resistance is increased. An excellent color filter can be provided.

According to the present invention, it is possible to provide a pigment dispersion composition having good pigment dispersibility and storage stability. Further, by using the pigment dispersion composition, it is possible to provide a photosensitive coloring composition capable of obtaining a cured product having excellent solvent resistance. Further, it is possible to provide a color filter having a cured product of the photosensitive coloring composition and an image display element provided with the color filter.

Claims (16)

1. Contains an amino group (g-1) with an ethylenically unsaturated group
   A polymerizable polymer dispersant, wherein the amino group (g-1) is at least one amino group selected from the group consisting of a secondary amino group and a tertiary amino group.
2. The polymerizable polymer dispersant according to claim 1, wherein the amino group (g-1) has a (meth) acryloyloxy group.
3. The polymerizable polymer dispersant according to claim 1 or 2, wherein the amino group (g-1) has a group represented by the following formula (1).
   -CH ₂ -CH (OH) -R ¹ -O- (CO) -CR ² = CH ₂ (1)
   (In the formula (1), R ¹ is a divalent linking group having 1 to 20 carbon atoms, and R ² represents a hydrogen atom or a methyl group.)
4. Polymer dispersant (A) and
   Pigment (B) and
   A pigment dispersion composition containing a solvent (C-1).
   The polymer dispersant (A) contains a polymerizable polymer dispersant (A-1) and a non-polymerizable polymer dispersant (A-2).
   The polymerizable polymer dispersant (A-1) is the polymerizable polymer dispersant according to any one of claims 1 to 3.
   The non-polymerizable polymer dispersant (A-2) does not have an ethylenically unsaturated group and is at least one substituent (g) selected from the group consisting of a tertiary amino group and a quaternary ammonium cation group. -2) A pigment dispersion composition comprising.
5. According to claim 4, the content ratio (mass ratio) of the polymerizable polymer dispersant (A-1) and the non-polymerizable polymer dispersant (A-2) is 1:99 to 80:20. The pigment dispersion composition according to the above.
6. The non-polymerizable polymer dispersant (A-2)
   At least one monomer selected from the group consisting of a monomer having a tertiary amino group and an ethylenically unsaturated group, and a monomer having a quaternary ammonium cation group and an ethylenically unsaturated group.
   The pigment dispersion composition according to claim 4 or 5, which is a block polymer with another monomer having an ethylenically unsaturated group.
7. The pigment dispersion composition according to any one of claims 4 to 6, wherein the pigment (B) contains a pigment having a halogenated phthalocyanine skeleton.
8. The pigment dispersion composition according to any one of claims 4 to 7, further comprising a binder resin (D-1).
9. With respect to 100 parts by mass of the pigment (B)
   The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
   The pigment dispersion composition according to claim 8, which contains 10 to 80 parts by mass of the binder resin (D-1).
10. The pigment dispersion composition according to any one of claims 4 to 7.
    Binder resin (D-2) and
    Reactive diluent (E) and
    A photosensitive coloring composition comprising a photopolymerization initiator (F).
11. With respect to 100 parts by mass of the pigment (B)
    The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
    The binder resin (D-2) is contained in an amount of 50 to 280 parts by mass.
    40 to 200 parts by mass of the reactive diluent (E) is contained.
    The photosensitive coloring composition according to claim 10, which contains 0.1 to 10 parts by mass of the photopolymerization initiator (F).
12. The pigment dispersion composition according to claim 8 or 9,
    Binder resin (D-2) and
    Reactive diluent (E) and
    A photosensitive coloring composition comprising a photopolymerization initiator (F).
13. With respect to 100 parts by mass of the pigment (B)
    The polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass, and the polymer dispersant (A) is contained in an amount of 10 to 80 parts by mass.
    A total of 50 to 280 parts by mass of the binder resin (D-1) and (D-2) is contained.
    40 to 200 parts by mass of the reactive diluent (E) is contained.
    The photosensitive coloring composition according to claim 12, which contains 0.1 to 10 parts by mass of the photopolymerization initiator (F).
14. A resin-cured film obtained by curing the photosensitive coloring composition according to any one of claims 10 to 13.
15. A color filter having a cured product of the photosensitive coloring composition according to any one of claims 10 to 13.
16. An image display element comprising the color filter according to claim 15.