TWI872215B - Diketopyrrolopyrrole pigment dispersing agent, pigment composition, colored composition, and color filter - Google Patents

Abstract

The object of the present invention is to provide a diketopyrrolopyrrole pigment dispersant, a pigment composition, a coloring composition and a color filter with high brightness and high contrast, wherein the diketopyrrolopyrrole pigment will not be crystallized even in the heating step. The above problem can be solved by the diketopyrrolopyrrole pigment dispersant and the pigment composition represented by the following general formula (1).

Description

Diketopyrrolopyrrole pigment dispersant, pigment composition, coloring composition and color filter

The present invention relates to a color filter pigment composition and a coloring composition for manufacturing a color filter used in a color liquid crystal display device and a color camera tube element, and a color filter formed using the same.

Liquid crystal display devices are display devices that control the polarization degree of light passing through the first polarizer by a liquid crystal layer sandwiched between two polarizers to control the amount of light passing through the second polarizer, and the type using twisted nematic (TN) liquid crystals has become the mainstream. Color display can be achieved by arranging a color filter between the two polarizers. In recent years, it has been used in televisions and personal computer monitors, etc. Therefore, the requirements for high brightness, high contrast, and high color reproduction of color filters have increased.

Color filters include: filters that are formed by arranging two or more fine stripe-shaped filter segments of different hues in parallel or crosswise on the surface of a transparent substrate such as glass; or filters that are formed by arranging fine filter segments in a certain arrangement vertically and horizontally. Generally speaking, most of them are formed by three color filter segments of red, green and blue, each of which is fine to several microns to hundreds of microns, and each hue is neatly arranged in a prescribed arrangement.

Generally speaking, in a color liquid crystal display device, a transparent electrode for driving the liquid crystal is formed on the color filter by evaporation or sputtering, and then an alignment film for aligning the liquid crystal in a certain direction is formed on the transparent electrode. In order to fully obtain the performance of these transparent electrodes and alignment films, a high temperature treatment of usually 200°C or more, preferably 230°C or more is required in the manufacturing step of forming the color filter. Therefore, at present, regarding color filters, a method called a pigment dispersion method that uses a pigment with excellent light resistance and heat resistance as a colorant has become the mainstream.

In the pigment dispersion method, a pigment with excellent light resistance and heat resistance such as a diketopyrrolopyrrole pigment, anthraquinone pigment, perylene pigment or disazo pigment is usually used as a colorant in the red filter segment alone or in combination.

C.I. Pigment Red 254 and C.I. Pigment Red 291, which are diketopyrrolopyrrole pigments, are pigments with particularly excellent brightness. However, in recent years, there has been a strong desire for high contrast in color filters, and therefore, the primary particle size of diketopyrrolopyrrole pigments needs to be miniaturized as much as possible. However, the miniaturized diketopyrrolopyrrole pigments have the property of easily crystallizing and growing due to the hydrogen bonds between their molecules, and therefore there is a problem that crystallization occurs during the heating step when forming a color filter, resulting in the generation of foreign matter.

Patent document 1 discloses a diketopyrrolopyrrole pigment derivative that can inhibit the crystallization of diketopyrrolopyrrole pigments, but the brightness reduction caused by the pigment derivative is large and the viscosity stability and solvent resistance are also issues, and further improvement is required. [Prior art document]

[Patent document] [Patent document 1] Japanese Patent Publication No. 2017-31330

[Problem to be solved by the invention] The problem to be solved by the present invention is to provide a color filter pigment composition, a coloring composition and a color filter using the same which have high brightness and high contrast and do not cause crystallization of diketopyrrolopyrrole pigments even in the heating step. [Technical means to solve the problem]

The inventors of the present invention have made repeated efforts to study and found that by using a specific diketopyrrolopyrrole pigment dispersant, a color filter with high brightness and high contrast and in which crystal precipitation caused by the heating step is suppressed can be obtained, thereby completing the present invention.

That is, the present invention relates to a diketopyrrolopyrrole pigment dispersant represented by the following general formula (1).

General formula (1) [Chemistry 5] [In the general formula (1), R ₁ to R ₁₀ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a phenyl group which may have a substituent, -CF ₃ , -OR ₁₁ , -SR ₁₂ , -N(R ₁₃ )R ₁₄ , -SO ₃ M, -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; R ₁₁ to R ₁₇ are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, a phenyl group which may have a substituent or an aralkyl group which may have a substituent; at least one of R ₁ to R ₁₀ is -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; -SO ₃ M represents a sulfo group or a metal salt of a sulfo group or an alkylammonium salt]

In addition, the present invention relates to the diketopyrrolopyrrole pigment dispersant, which is represented by the following general formula (2), general formula (3) or general formula (5).

General formula (2) [Chemistry 6] General formula (3) [Chemistry 7]

General formula (5) [Chemical 8] [In the general formula (2), the general formula (3) and the general formula (5), _R21 to _R24 , _R27 and _R28 are independently fluorine atoms, chlorine atoms, bromine atoms, cyano groups, alkyl groups having 1 to 20 carbon atoms or phenyl groups; _X1 to _X4 , _X7 and _X8 are independently hydrogen atoms, alkyl groups having 1 to 20 carbon atoms which may have a substituent, phenyl groups which may have a substituent or aralkyl groups which may have a substituent; wherein _X1 and _X2 are not hydrogen atoms at the same time, _X3 and _X4 are not hydrogen atoms at the same time, and _X7 and _X8 are not hydrogen atoms at the same time; _-SO3M represents a sulfo group or a metal salt or an alkylammonium salt of a sulfo group]

In addition, the present invention relates to a pigment composition, which is characterized by containing a pigment and the diketopyrrolopyrrole pigment dispersant.

In addition, the present invention relates to a pigment composition, wherein the pigment contains a diketopyrrolopyrrole red pigment.

In addition, the present invention relates to a coloring composition, which is characterized by containing the pigment composition, a binder resin and an organic solvent.

In addition, the present invention relates to a coloring composition, characterized in that it further contains a photopolymerizable monomer and/or a photopolymerization initiator.

In addition, the present invention relates to a color filter, characterized in that it includes a filter segment formed by the coloring composition. [Effect of the invention]

According to the present invention, a color filter pigment composition, a coloring composition and a color filter using the same can be provided, which have high brightness and high contrast and do not cause crystal precipitation of diketopyrrolopyrrole pigment even in a heating step.

The present invention is described in detail below. Furthermore, the "C.I." listed below refers to the Colour Index (C.I.).

(Diketopyrrolopyrrole pigment dispersant) The present invention is a diketopyrrolopyrrole pigment dispersant represented by the following general formula (1). General formula (1)

[Chemistry 9] [In the general formula (1), R ₁ to R ₁₀ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a phenyl group which may have a substituent, -CF ₃ , -OR ₁₁ , -SR ₁₂ , -N(R ₁₃ )R ₁₄ , -SO ₃ M, -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; R ₁₁ to R ₁₇ are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, a phenyl group which may have a substituent or an aralkyl group which may have a substituent; at least one of R ₁ to R ₁₀ is -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; -SO ₃ M represents a sulfo group or a metal salt of a sulfo group or an alkylammonium salt]

As the alkyl group having 1 to 20 carbon atoms which may have a substituent, there are unsubstituted or ether-bonded oxyalkylene groups, which may be linear or branched. Specifically, there may be methyl, ethyl, propyl, isopropyl, butyl, sec-butyl, tert-butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, octadecyl, 1,5-dimethylhexyl, 1,6-dimethylheptyl, 2-ethylhexyl, 2-methoxyethyl, 2-ethoxyethyl, 3-ethoxypropyl, polyoxyethylene, etc., but are not limited thereto. In addition, from the viewpoint of crystallization suppression and ease of synthesis, the alkyl group having 3 to 20 carbon atoms is preferred, and the alkyl group having 4 to 18 carbon atoms is more preferred.

Examples of the phenyl group which may have a substituent include a phenyl group having a substituent such as an alkyl group having 1 to 20 carbon atoms, a trifluoromethyl group, a halogen atom, a nitro group, a cyano group, a carbamoyl group, a sulfamoyl group, an alkoxy group having 1 to 4 carbon atoms. More specifically, examples include a phenyl group, a p-methylphenyl group, a 4-tert-butylphenyl group, a p-nitrophenyl group, a p-methoxyphenyl group, a p-chlorophenyl group, a 2,4-dichlorophenyl group, and a 3-carbamoylphenyl group. The present invention is not limited to these.

Specific examples of the aralkyl group which may have a substituent include benzyl, 4-methylbenzyl, 4-t-butylbenzyl, 4-methoxybenzyl, 4-nitrobenzyl, and 2,4-dichlorobenzyl, but are not limited thereto.

Examples of the metal that forms a metal salt with the sulfonic group in the above-mentioned -SO ₃ M include sodium, potassium, magnesium, calcium, manganese, iron, cobalt, nickel, copper, zinc, silver, and aluminum, but the metal is not limited to these.

Examples of the amine that forms an alkylammonium salt with the sulfonic group in the -SO ₃ M include, but are not limited to, lower amines such as dimethylamine, trimethylamine, diethylamine, triethylamine, hydroxyethylamine, dihydroxyethylamine, 2-ethylhexylamine, N,N-dimethylaminopropylamine, N,N-diethylaminopropylamine, and N,N-dibutylaminopropylamine; long-chain alkylamines having an alkyl group with 2 or more carbon atoms such as laurylamine, oleylamine, palmitylamine, stearylamine, and dimethyllaurylamine; and long-chain alkyl quaternary ammonium ions having an alkyl group with 12 or more carbon atoms such as laurylammonium, stearylammonium, lauryltrimethylammonium, dilauryldimethylammonium, stearyltrimethylammonium, and distearyldimethylammonium.

In addition, as the diketopyrrolopyrrole pigment dispersant of the present invention, from the viewpoint of hue, contrast, and ease of synthesis, the structures represented by the following general formulas (2) to (5) are preferred, and the structures represented by general formula (2), general formula (3) or general formula (5) are particularly preferred.

General formula (2) [Chemical 10]

General formula (3) [Chemical 11]

General formula (4) [Chemical 12]

General formula (5) [Chemical 13]

[In general formulae (2) to (5), _R21 to _R28 are independently fluorine, chlorine, bromine, cyano, alkyl or phenyl groups having 1 to 20 carbon atoms; _X1 to _X8 are independently hydrogen, alkyl or phenyl groups having 1 to 20 carbon atoms; _X1 and _X2 are not simultaneously hydrogen, _X3 and _X4 are not simultaneously hydrogen, _X5 and _X6 are not simultaneously hydrogen, and _X7 and _X8 are not simultaneously hydrogen; _-SO3M is a sulfonic group or a metal salt or alkylammonium salt of a sulfonic group]

From the viewpoint of the crystallization suppression effect, _X1 to _X8 are preferably an alkyl group having 3 or more carbon atoms which may be substituted, a phenyl group having 3 or more carbon atoms which may be substituted, or an aralkyl group having 4 or more carbon atoms which may be substituted, and more preferably a branched alkyl group.

Specific examples of the diketopyrrolopyrrole pigment dispersant that can be used in the present invention are listed below, but are not limited to these.

General formula (2) [Chemical 14]

Table 1 shows specific examples of R ₂₁ , R ₂₂ , X ₁ and X ₂ in the general formula (2).

[Table 1] Table 1 Pigment dispersant R ₂₁ R ₂₂ X ₁ X ₂ (2-1) CH ₃ CH ₃ -(CH ₂ ) ₂ CH ₃ H (2-2) CH ₃ CH ₃ -CH ₂ CH(CH ₃ ) ₂ H (2-3) CH ₃ CH ₃ -C(CH ₃ ) ₃ H (2-4) CH ₃ CH ₃ -(CH ₂ ) ₇ CH ₃ H (2-5) CH ₃ CH ₃ -(CH ₂ ) ₁₇ CH ₃ H (2-6) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ H (2-7) CH ₃ CH ₃ -CH ₂ CH{(CH ₂ ) ₃ CH ₃ }{(CH ₂ ) ₅ CH ₃ } H (2-8) CH ₃ CH ₃ -CH ₂ CH ₃ -CH ₂ CH ₃ (2-9) CH ₃ CH ₃ -(CH ₂ ) ₂ CH ₃ -(CH ₂ ) ₂ CH ₃ (2-10) CH ₃ CH ₃ -(CH ₂ ) ₄ CH ₃ -(CH ₂ ) ₄ CH ₃ (2-11) CH ₃ CH ₃ -(CH ₂ ) ₅ CH ₃ -(CH ₂ ) ₅ CH ₃ (2-12) CH ₃ CH ₃ -(CH ₂ ) ₉ CH ₃ -(CH ₂ ) ₉ CH ₃ (2-13) CH ₃ CH ₃ -(CH ₂ ) ₂ CH(CH ₃ ) ₂ -(CH ₂ ) ₂ CH(CH ₃ ) ₂ (2-14) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ (2-15) CH ₃ CH ₃ -CH ₂ CH ₃ -(CH ₂ ) ₃ CH ₃ (2-16) CH ₃ CH ₃ (2-17) CH ₃ CH ₃ (2-18) CH ₃ CH ₃ -(CH ₂ CH ₂ O) ₄ CH ₃ H

[Table 1] (Continued) Table 1 continued Pigment dispersant R ₂₁ R ₂₂ X ₁ X ₂ (2-19) H H -CH ₂ CH(CH ₃ ) ₂ H (2-20) H H -(CH ₂ ) ₄ CH ₃ -(CH ₂ ) ₄ CH ₃ (2-21) Cl Cl _{-CH2CH ( CH3} ) _CH2CH3 H (2-22) Cl Cl H (2-23) -(CH ₂ ) ₂ CH(CH ₃ ) ₂ H (2-24) H (2-25) Br Br -CH{(CH ₂ ) ₂ CH ₃ } ₂ H (2-26) Br Br H (2-27) -(CH ₂ ) ₅ CH ₃ -(CH ₂ ) ₅ CH ₃ (2-28) -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ (2-29) -O(CH ₂ ) ₄ CH ₃ -O(CH ₂ ) ₄ CH ₃ -(CH ₂ ) ₁₁ CH ₃ H (2-30) -S(CH ₂ ) ₇ CH ₃ -S(CH ₂ ) ₇ CH ₃ H (2-31) -N(CH ₂ CH ₃ ) ₂ -N(CH ₂ CH ₃ ) ₂

General formula (3) [Chemical 15]

Table 2 shows specific examples of R ₂₃ , R ₂₄ , X ₃ and X ₄ in the general formula (3).

[Table 2] Table 2 Pigment dispersant R ₂₃ R ₂₄ X ₃ X ₄ (3-1) -CN -CN -(CH ₂ ) ₇ CH ₃ -(CH ₂ ) ₇ CH ₃ (3-2) -CN -CN -(CH ₂ ) ₂ OCH ₃ -(CH ₂ ) ₂ OCH ₃

General formula (4) [Chemical 16]

Table 3 shows specific examples of R ₂₅ , R ₂₆ , X ₅ and X ₆ in the general formula (4).

[Table 3] Table 3 Pigment dispersant R ₂₅ R ₂₆ X ₅ X ₆ (4-1) CF ₃ CF ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ (4-2) F F -(CH ₂ ) ₉ CH ₃ -(CH ₂ ) ₉ CH ₃

Table 4 shows specific examples of R ₂₇ , R ₂₈ , X ₇ , X ₈ and -SO ₃ M in the general formula (5).

General formula (5) [Chemical 17]

[Table 4] Table 4 Pigment dispersant R ₂₇ R ₂₈ X ₇ X ₈ -SO ₃ M (5-1) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -SO ₃ H (5-2) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -SO ₃ Na (5-3) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -SO ₃ Zn _1/2 (5-4) CH ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -SO ₃ Al _1/3 (5-5) -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -CH ₂ CH(CH ₂ CH ₃ )(CH ₂ ) ₃ CH ₃ -SO ₃ H

Among the above structures, (2-5 to 2-7, 2-10 to 2-14, 2-27, 2-28), (3-1, 3-2), (5-1), (5-2), etc. are particularly preferred from the viewpoints of brightness, contrast, and the effect of suppressing crystal precipitation.

(Method for producing diketopyrrolopyrrole pigment dispersant) There are several methods for producing the diketopyrrolopyrrole pigment dispersant of the present invention, and there are no particular limitations. However, the most convenient method is to synthesize the diketopyrrolopyrrole pigment by sulfonating the diketopyrrolopyrrole pigment synthesized by the succinic acid diester synthesis method with fuming sulfuric acid, and then using a chlorinating agent to produce sulfonyl chloride, and then reacting with any amine to perform sulfonyl amination.

(Method for producing diketopyrrolopyrrole) Diketopyrrolopyrrole can be produced by the succinic acid diester synthesis method. That is, 1 mol of succinic acid diester and 2 mol of benzonitrile compound represented by the following formula (A) are subjected to condensation reaction in an inert organic solvent such as tertiary amyl alcohol, in the presence of an alkali metal or an alkali metal alkoxide, at a high temperature of 80°C to 110°C to produce an alkali metal salt of the diketopyrrolopyrrole compound. Subsequently, the alkali metal salt of the diketopyrrolopyrrole compound is protonated using water, alcohol, acid, etc., thereby obtaining various diketopyrrolopyrrole pigments. At this time, the size of the primary particle obtained can be controlled by the temperature, type, ratio or amount of water, alcohol or acid during protonation. The method for producing diketopyrrolopyrrole is not limited to the above method.

General formula (A) [Chemical 18]

[In the general formula (A), R ₃₁ to R ₃₅ are each independently a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, a cyano group, an alkyl group having 1 to 20 carbon atoms, a phenyl group which may have a substituent, -CF ₃ , -OR ₁₁ , -SR ₁₂ , -N(R ₁₃ )R ₁₄ , -SO ₃ M, -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; R ₁₁ to R ₁₇ are each independently an alkyl group having 1 to 20 carbon atoms which may have a substituent, a phenyl group which may have a substituent or an aralkyl group which may have a substituent; at least one of R ₁ to R ₁₀ is -SO ₂ NHR ₁₅ or -SO ₂ N(R ₁₆ )R ₁₇ ; -SO ₃ M represents a sulfo group or a metal salt of a sulfo group or an alkylammonium salt]

In addition, in the succinic acid diester synthesis method, at least two benzonitrile compounds having different structures can be used to produce diketopyrrolopyrroles having a plurality of structures mixed therein.

Diketopyrrolopyrrole can be sulfonated by reacting with fuming sulfuric acid. In the diketopyrrolopyrrole pigment dispersant of the present invention, the sulfonic acid group can be 1 or 2 equivalents relative to one molecule of diketopyrrolopyrrole, and can also be mixed.

The sulfonated diketopyrrolopyrrole can be easily sulfonated by reacting with a primary or secondary amine by sulfonyl chlorination using a chlorinating agent such as thionyl chloride.

As the amine used to prepare the diketopyrrolopyrrole pigment dispersant of the present invention, there can be mentioned methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, octylamine, decylamine, dodecylamine, hexadecylamine, octadecylamine, dimethylamine, N-ethylisopropylamine, N-methylbutylamine, N-methylisobutylamine, N-butylethylamine, N-tert-butylethylamine, diisopropylamine, dipropylamine, N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N-isobutyl-sec-butylamine, dipentylamine, diisopropylamine, diisopropylamine, diisopropylamine, diisopropylamine, diisopropylamine, diisobutylamine, diisobutylamine, diisobutylamine, diisobutylamine, diisobutylamine, diisobutylamine, diisobutylamine, diisopropyl ... Amylamine, dihexylamine, di(2-ethylhexyl)amine, dioctylamine, N-methyloctadecylamine, didecylamine, diallylamine, N-ethyl-1,2-dimethylpropylamine, N-methylhexylamine, dioleylamine, distearylamine, aniline, 2-methylaniline, 3-methylaniline, 4-methylaniline, 4-ethylaniline, 4-propylaniline, 4-butylaniline, 4-pentylaniline, 4-decylaniline, 3,4-dimethylaniline, bis(4-tert-butylphenyl)amine, etc., but are not limited to these.

<Pigment composition> Next, the pigment composition of the present invention is described. The pigment composition of the present invention contains a pigment and the diketopyrrolopyrrole pigment dispersant of the present invention.

As the pigment contained in the pigment composition, various commercially available organic pigments or inorganic pigments can be used.

Examples of organic pigments include azo pigments, anthranthrone pigments, anthrapyrimidine pigments, anthraquinone pigments, isoindolinone pigments, isoindolinone pigments, indanthrone pigments, quinacridone pigments, quinophthalone pigments, dioxazine pigments, diketopyrrolopyrrole pigments, thiazine indigo pigments, thioindigo pigments, pyranthrone pigments, phthalocyanine pigments, flavanthrone pigments, perinone pigments, perylene pigments, and benzimidazolone pigments. Inorganic pigments include, for example, carbon black, titanium oxide, chromium yellow, cadmium yellow, cadmium red, iron oxide red, iron black, zinc white, Prussian blue, ultramarine blue, etc. These pigments may also be used in combination.

If the diketopyrrolopyrrole pigment dispersant is used in a pigment having the same or similar chemical structure, it can effectively improve non-aggregation, non-crystallization, fluidity, etc. In addition, in terms of hue, it is preferably used in yellow to red pigments, and more preferably in orange to red pigments.

In particular, the diketopyrrolopyrrole pigment dispersant is preferably used for red pigments represented by diketopyrrolopyrrole red pigments, quinacridone red pigments, thiazine indigo red pigments, anthraquinone red pigments, and azo red pigments, among which diketopyrrolopyrrole red pigments are particularly preferred.

The amount of the diketopyrrolopyrrole pigment dispersant contained in the pigment composition is preferably 0.1 to 30 parts by weight, more preferably 1 to 20 parts by weight, relative to 100 parts by weight of the pigment. If the content of the diketopyrrolopyrrole pigment dispersant is less than 0.1 parts by weight, it is difficult to obtain the effect of the added diketopyrrolopyrrole pigment dispersant, and if it is more than 30 parts by weight, the diketopyrrolopyrrole pigment dispersant has a great influence on the hue, sometimes resulting in a decrease in brightness.

Regarding the pigment composition, a sufficient dispersion effect can be obtained even if the pigment powder and the powder of the diketopyrrolopyrrole pigment dispersant are simply mixed to prepare the pigment composition. However, the pigment composition can also be obtained by the following methods: a method of mechanically mixing the pigment powder and the powder of the pigment dispersant using a dissolver, a high-speed mixer, a homogenizer, a kneader, a roller mill, an attritor, a sand mill, various pulverizers, etc.; a method of adding a solution containing the pigment dispersant to a suspension system of the pigment based on water or an organic solvent to deposit the pigment dispersant on the surface of the pigment; a method of co-dissolving an organic pigment and a pigment dispersant in a solvent having a strong dissolving power such as sulfuric acid and co-precipitating them using a poor solvent such as water, etc.

(Other pigment dispersants) The pigment composition of the present invention may contain pigment dispersants other than the diketopyrrolopyrrole pigment dispersant of the present invention. As the pigment dispersant that can be used in the present invention, a known pigment dispersant having an acidic group, an alkaline group, a neutral group, etc. in the organic pigment residue can be used. For example, compounds having acidic functional groups such as sulfonic groups, carboxyl groups, and phosphoric acid groups and their amine salts, compounds having alkaline functional groups such as sulfonamide groups or tertiary amino groups at the ends, and compounds having neutral functional groups such as phenyl or o-phthalimidoalkyl groups can be listed. Examples of organic pigments include: diketopyrrolopyrrole pigments; phthalocyanine pigments such as copper phthalocyanine, zinc phthalocyanine, aluminum phthalocyanine, copper phthalocyanine halides, zinc phthalocyanine halides, aluminum phthalocyanine halides, and metal-free phthalocyanine; anthraquinone pigments such as aminoanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavonol, anthraquinone, indanthrone, pyranthrone, and violanthrone; quinacridone pigments; di- Oxazine pigments; perinone pigments; perylene pigments; thiazine indigo pigments; triazine pigments; benzimidazolone pigments; indole pigments such as benzisoindole; isoindoline pigments; isoindoline ketone pigments; quinoline yellow pigments; naphthol pigments; threne pigments; metal complex pigments; azo pigments such as azo, disazo, and polyazo pigments, etc. More specifically, Japanese Patent Laid-Open No. 61-246261, Japanese Patent Laid-Open No. 63-264674, Japanese Patent Laid-Open No. 09-272812, Japanese Patent Laid-Open No. 10-245501, Japanese Patent Laid-Open No. 10-265697, Japanese Patent Laid-Open No. 11-199796, Japanese Patent Laid-Open No. 2001-172520, Japanese Patent Laid-Open No. 2001-220520, Japanese Patent Laid-Open No. 2001-272813, Japanese Patent Laid-Open No. 2001-272814, Japanese Patent Laid-Open No. 2001-272815, Japanese Patent Laid-Open No. 2001-272816, Japanese Patent Laid-Open No. 2001-272817, Japanese Patent Laid-Open No. 2001-272818, Japanese Patent Laid-Open No. 2001-272819, Japanese Patent Laid-Open No. 2001-272810, Japanese Patent Laid-Open No. 2001-272813, Japanese Patent Laid-Open No. 2001-272817, Japanese Patent Laid-Open No. 2001-272819, Japanese Patent Laid-Open No. 2001-272818 Japanese Patent Application Publication No. 2002-201377, Japanese Patent Application Publication No. 2003-165922, Japanese Patent Application Publication No. 2003-168208, Japanese Patent Application Publication No. 2003-171594, Japanese Patent Application Publication No. 2004-217842, Japanese Patent Application Publication No. 2005-213404, Japanese Patent Application Publication No. 2006-291194, Japanese Patent Application Publication No. 2007-079094, Japanese Patent Application Publication No. 200 7-226161, Japanese Patent Publication No. 2007-314681, Japanese Patent Publication No. 2007-314785, Japanese Patent Publication No. 2008-31281, Japanese Patent Publication No. 2009-57478, WO2009/025325, WO2009/081930, Japanese Patent Publication No. 2011-162662, WO2011/052617, Japanese Patent Publication No. 20 Known pigment dispersants described in WO2012-172092, Japanese Patent Laid-Open No. 2012-208329, Japanese Patent Laid-Open No. 2012-226110, WO2012/102399, Japanese Patent Laid-Open No. 2014-5439, WO2016/163351, Japanese Patent Laid-Open No. 2017-156397, Japanese Patent No. 5753266, etc., can be used alone or in combination of two or more. Furthermore, in these documents, the pigment dispersant is described as a derivative, a pigment derivative, a dye derivative, or simply as a compound, but the compound having a functional group such as an acidic group, an alkaline group, or a neutral group in the organic dye residue has the same meaning as the pigment dispersant.

When the pigment dispersant is used in the present invention, it is preferably derived from a diketopyrrolopyrrole pigment, anthraquinone pigment, quinoline yellow pigment or azo pigment as an organic pigment residue from the viewpoint of hue or contrast ratio.

(Pigment micronization) The pigment used in the pigment composition of the present invention is preferably used after micronization. The micronization method is not particularly limited, and for example, any of wet milling, dry milling, and dissolution separation methods may be used. As exemplified in the present invention, the pigment may be micronized by salt milling using a kneader method, which is a type of wet milling. The average primary particle size of the pigment measured by a transmission electron microscope (TEM) is preferably in the range of 5 nm to 90 nm. If the particle size is less than 5 nm, it is difficult to disperse in an organic solvent, and if the particle size is greater than 90 nm, a sufficient contrast ratio cannot be obtained. For this reason, a more preferred average primary particle size is in the range of 10 nm to 70 nm.

The so-called salt milling treatment is the following treatment: using a batch or continuous mixer such as a kneader, two-rod roll mill, three-rod roll mill, ball mill, grinder, sand mill, planetary mixer, etc., the mixture of pigment, water-soluble inorganic salt and water-soluble organic solvent is mechanically mixed while heating, and then the water-soluble inorganic salt and water-soluble organic solvent are removed by washing. The water-soluble inorganic salt acts as a crushing aid, and the high hardness of the inorganic salt is used to crush the pigment during salt milling. By optimizing the conditions for the salt milling of the pigment, it is possible to obtain a pigment with extremely fine primary particles, a narrow distribution range, and a sharp particle size distribution.

As the water-soluble inorganic salt, sodium chloride, potassium chloride, sodium sulfate, etc. can be used. In terms of price, sodium chloride (salt) is preferably used. In terms of processing efficiency and production efficiency, the water-soluble inorganic salt is preferably used in an amount of 50 to 2000 parts by mass, and most preferably 300 to 1000 parts by mass, relative to 100 parts by mass of the pigment.

The water-soluble organic solvent plays a role in moistening the pigment and the water-soluble inorganic salt. If it is an organic solvent that is dissolved (mixed) in water and does not substantially dissolve the inorganic salt used, it is not particularly limited. Wherein, due to the temperature rise during salt grinding, the solvent is easily evaporated, so in terms of safety, it is preferably a high boiling point solvent with a boiling point of more than 120°C. For example, 2-methoxyethanol, 2-butoxyethanol, 2-(isopentyloxy)ethanol, 2-(hexyloxy)ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. can be used. The water-soluble organic solvent is preferably used in an amount of 5 to 1000 parts by mass, and most preferably 50 to 500 parts by mass, based on 100 parts by mass of the pigment.

During the salt milling process, the diketopyrrolopyrrole pigment dispersant or/and pigment dispersant of the present invention may be added to improve the mixing efficiency, which is very effective for the refinement and granulation of the pigment. The amount of the diketopyrrolopyrrole pigment dispersant or/and pigment dispersant used is preferably such that the color tone is not affected, i.e., in the range of 5% to 40% by mass relative to 100% by mass of the pigment.

In addition, when the salt milling treatment is performed, a resin may be added as needed. The type of the resin used is not particularly limited, and natural resins, modified natural resins, synthetic resins, synthetic resins modified from natural resins, etc. may be used. The resin used is preferably solid and water-insoluble at room temperature, and further preferably partially soluble in the organic solvent. The amount of the resin used is preferably in the range of 5 to 200 parts by mass relative to 100 parts by mass of the pigment.

(Coloring composition) The pigment composition of the present invention can be used as a coloring composition by using it together with a binder resin and an organic solvent.

(Other coloring agents) In order to adjust the chromaticity, etc., the coloring composition of the present invention may also be used in combination with pigments or dyes other than the pigment composition within a range that does not impair the effects of the present invention.

For example, one can cite the following red pigments: C.I. pigment red 7, 14, 41, 48:1, 48:2, 48:3, 48:4, 57:1, 81, 81:1, 81:2, 81:3, 81:4, 122, 146, 168, 169, 176, 177, 178, 179, 184, 185, 187, 200, 202, 208, 210, 242, 246, 254, 255, 264, 270, 272, 273, 274, 276, 277, 278, 279, 280, 281, 282, 283, 284, 285, 286, 287 or 291. Examples of red dyes include oxyanthracene dyes, azo dyes (pyridone dyes, barbituric acid dyes, metal complex dyes, etc.), disazo dyes, and anthraquinone dyes. Specifically, examples include salt compounds of oxyanthracene dyes such as C.I. acid red 52, 87, 92, 289, and 338.

In addition, orange pigments such as C.I. pigment orange 43, 71 or 73 and/or C.I. pigment yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120 , 123, 126, 127, 128, 129, 138, 139, 147, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, 198, 199, 213, 214, 218, 219, 220, 221 or 231 yellow pigment. In addition, examples of orange dyes and/or yellow dyes include quinoline-based dyes, azo-based dyes (pyridone-based dyes, barbituric acid-based dyes, metal complex-based dyes, etc.), disazo-based dyes, and methine-based dyes.

Preferred coloring agents used in combination include: C.I. Pigment Red 177, 254, 242, 291, C.I. Pigment Yellow 139, 150, 185.

When a colorant other than the diketopyrrolopyrrole pigment composition is used in combination, the diketopyrrolopyrrole pigment composition of the present invention is preferably in the range of 40% to 100% by mass of the total amount of the colorant (100% by mass). More preferably, it is in the range of 60% to 100% by mass. When the diketopyrrolopyrrole pigment composition of the present invention is less than 40% by mass, the excellent effect of brightness and contrast ratio cannot be fully exerted.

<Resin-type dispersant> The coloring composition of the present invention may contain a resin-type dispersant. The dispersant includes a coloring agent affinity site having the property of being adsorbed to the added coloring agent and a site having compatibility with the coloring agent carrier, and plays a role in stabilizing the dispersion of the coloring agent in the coloring agent carrier by being adsorbed to the added coloring agent. As the resin type dispersant, specifically, polycarboxylic acid esters such as polyurethane and polyacrylate; unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, polycarboxylic acid alkylamine salts, polysiloxanes, long-chain polyaminoamide phosphates, polycarboxylic acid esters containing hydroxyl groups or modified products thereof; amides or their salts formed by the reaction of poly(lower alkylene imine) with polyesters having free carboxyl groups; dispersants; water-soluble resins or water-soluble polymers such as (meth)acrylic acid-styrene copolymers, (meth)acrylic acid-(meth)acrylate copolymers, styrene-maleic acid copolymers, polyvinyl alcohol, polyvinyl pyrrolidone, etc.; polyester series, modified polyacrylate series, ethylene oxide/propylene oxide addition compounds, phosphate series, etc., which can be used alone or in combination of two or more, but are not necessarily limited to these.

Among the resin type dispersants, graft copolymers containing nitrogen atoms, acrylic block copolymers containing nitrogen atoms and having functional groups such as tertiary amino groups, quaternary ammonium alkalis, and nitrogen-containing heterocyclic rings on the side chains, and urethane polymer dispersants are well known because they can reduce the viscosity of the dispersion and show a high contrast ratio even with a small amount of addition.

When a resin dispersant is used in the present invention, a resin dispersant having an acidic substituent is preferred, and a resin dispersant having an aromatic carboxyl group is particularly preferred because it has a particularly large effect of preventing the re-agglomeration of the coloring agent after dispersion. As resin dispersants having an aromatic carboxyl group, resin dispersants described in WO2008/007776, Japanese Patent Laid-Open No. 2008-029901, Japanese Patent Laid-Open No. 2009-155406, Japanese Patent Laid-Open No. 2009-155406, Japanese Patent Laid-Open No. 2010-185934, and Japanese Patent Laid-Open No. 2011-157416 can be cited, but the present invention is not limited to these.

The resin dispersant is preferably used in an amount of about 5 to 200 parts by mass based on the total amount of the colorant, and more preferably about 5 to 100 parts by mass from the viewpoint of film-forming properties.

<Binder resin> The binder resin used in the coloring composition of the present invention allows the coloring agent to be dispersed, dyed or impregnated, and thermoplastic resins and the like can be cited. In addition, when used in the form of an alkali-developable coloring anti-etching agent, it is preferred to use an alkali-soluble vinyl resin obtained by copolymerizing an ethylenically unsaturated monomer containing an acidic group. In addition, in order to further improve the photosensitivity, an active energy ray-curable resin having an ethylenically unsaturated double bond can also be used.

In particular, when an active energy ray-curable resin having an ethylenically unsaturated double bond in the side chain is used in an alkali-developable coloring resist material, the resin undergoes three-dimensional crosslinking when a coating film is formed by exposure to active energy rays, thereby fixing the coloring agent, improving heat resistance, and suppressing fading (deterioration of spectral characteristics) of the coloring agent due to heat. In addition, it also has the effect of suppressing aggregation and precipitation of coloring agent components in the developing step.

The resin is preferably a resin having a spectral transmittance of preferably 80% or more, more preferably 95% or more in all wavelength regions of 400 nm to 700 nm in the visible light region.

In order to disperse the colorant preferably, the weight average molecular weight (Mw) of the resin is preferably in the range of 2,000 to 80,000, more preferably in the range of 3,000 to 40,000. In addition, the number average molecular weight (Mn) is preferably in the range of 3,000 to 40,000, and the value of Mw/Mn is preferably 10 or less.

When a resin is used as a coloring composition for a color filter, the balance between the carboxyl group that functions as a colorant adsorption group and an alkali-soluble group during development, and the aliphatic group and aromatic group that function as an affinity group for the colorant carrier and solvent is important for the dispersibility, permeability, development, and durability of the colorant, and it is preferred to use a resin with an acid value of 20 mgKOH/g to 300 mgKOH/g. If the acid value is less than 20 mgKOH/g, the solubility in the developer is poor and it is difficult to form a fine pattern. If it exceeds 300 mgKOH/g, there is a situation where no fine pattern is left.

The resin is preferably used in an amount of 20 parts by mass or more based on 100 parts by mass of the total mass of the colorant in terms of good film-forming properties and various resistances, and is preferably used in an amount of 1000 parts by mass or less in terms of high colorant concentration and good color properties.

Examples of the thermoplastic resin used in the resin include acrylic resin, butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, polyurethane resin, polyester resin, vinyl resin, alkyd resin, polystyrene resin, polyamide resin, rubber resin, cyclized rubber resin, cellulose, polyethylene (high-density polyethylene (HDPE), low-density polyethylene (LDPE)), polybutadiene, and polyimide resin. Among them, acrylic resin is preferably used.

As ethylene-based alkali-soluble resins obtained by copolymerizing ethylene unsaturated monomers containing acidic groups, for example, resins having acidic groups such as carboxyl groups and sulfonic groups can be cited. As alkali-soluble resins, specifically, acrylic resins having acidic groups, α-olefin/maleic acid (anhydride) copolymers, styrene/styrene sulfonic acid copolymers, ethylene/(meth)acrylic acid copolymers, or isobutylene/maleic acid (anhydride) copolymers can be cited. Among them, at least one resin selected from acrylic resins having acidic groups and styrene/styrene sulfonic acid copolymers, especially acrylic resins having acidic groups, have high heat resistance and transparency, and can therefore be suitably used.

Examples of the active energy ray-curable resin having an ethylenically unsaturated double bond include a resin into which an ethylenically unsaturated double bond is introduced by the following method (i) or (ii).

[Method (i)] As method (i), for example, there is a method in which a carboxyl group of an unsaturated monobasic acid having an unsaturated ethylenic double bond is subjected to an addition reaction with a side chain ethylenic group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having an ethylenic group and one or more other monomers, and the generated hydroxyl group is reacted with a polyacid anhydride to introduce an unsaturated ethylenic double bond and a carboxyl group.

Examples of the unsaturated ethylenic monomer having an epoxy group include glycidyl (meth)acrylate, methylglycidyl (meth)acrylate, 2-glycidyloxyethyl (meth)acrylate, 3,4-epoxybutyl (meth)acrylate, and 3,4-epoxycyclohexyl (meth)acrylate, and these may be used alone or in combination of two or more. Glycidyl (meth)acrylate is preferred from the viewpoint of reactivity with the unsaturated monobasic acid in the next step.

Examples of the unsaturated monobasic acid include (meth)acrylic acid, crotonic acid, o-vinylbenzoic acid, m-vinylbenzoic acid, p-vinylbenzoic acid, and monocarboxylic acids such as α-halogenated alkyl, alkoxy, halogen, nitro, and cyano-substituted (meth)acrylic acid. These may be used alone or in combination of two or more.

Examples of the polyacid anhydride include tetrahydrophthalic anhydride, phthalic anhydride, hexahydrophthalic anhydride, succinic anhydride, and maleic anhydride. These may be used alone or in combination of two or more. The number of carboxyl groups may be increased by hydrolyzing the remaining anhydride groups using tricarboxylic anhydride such as trimellitic anhydride or tetracarboxylic dianhydride such as pyromellitic dianhydride as needed. In addition, if tetrahydrophthalic anhydride or maleic anhydride having an unsaturated ethylenic double bond is used as the polyacid anhydride, the unsaturated ethylenic double bond may be further increased.

As a similar method to method (i), for example, there is a method in which an unsaturated ethylenic monomer having an epoxy group is added to a part of the side chain carboxyl groups of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a carboxyl group with one or more other monomers, thereby introducing an unsaturated ethylenic double bond and a carboxyl group.

[Method (ii)] As method (ii), there is a method of reacting an isocyanate group of an unsaturated ethylenic monomer having an isocyanate group with a side chain hydroxyl group of a copolymer obtained by copolymerizing an unsaturated ethylenic monomer having a hydroxyl group with another monomer of an unsaturated monobasic acid having a carboxyl group or other monomers.

Examples of the unsaturated ethylenic monomer having a hydroxyl group include hydroxyalkyl (meth)acrylates such as 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 3-hydroxypropyl (meth)acrylate, 2-hydroxybutyl (meth)acrylate, 3-hydroxybutyl (meth)acrylate, 4-hydroxybutyl (meth)acrylate, glycerol (meth)acrylate, and cyclohexanedimethanol mono(meth)acrylate. These may be used alone or in combination of two or more. In addition, polyether mono(meth)acrylates obtained by addition-polymerizing ethylene oxide, propylene oxide and/or butylene oxide, or (poly)ester mono(meth)acrylates obtained by addition-polymerizing (poly)γ-valerolactone, (poly)ε-caprolactone and/or (poly)12-hydroxystearic acid, etc., to the above-mentioned hydroxyalkyl (meth)acrylates may be used. From the viewpoint of suppressing foreign matter in the coating film, 2-hydroxyethyl (meth)acrylate or glycerol (meth)acrylate is preferred.

Examples of the unsaturated ethylenic monomer having an isocyanate group include 2-(meth)acryloyloxyethyl isocyanate and 1,1-bis[(meth)acryloyloxy]ethyl isocyanate, but the present invention is not limited thereto and two or more thereof may be used in combination.

<Thermosetting compound> The coloring composition of the present invention may contain a thermosetting compound. Examples of thermosetting compounds include epoxy compounds and/or resins, benzoguanamine compounds and/or resins, rosin-modified maleic acid compounds and/or resins, rosin-modified fumaric acid compounds and/or resins, melamine compounds and/or resins, urea compounds and/or resins, and phenolic compounds and/or resins, but the present invention is not limited thereto. When a thermosetting compound is used in the present invention, an epoxy compound is preferred from the viewpoint of heat resistance, solvent resistance, and the like. The epoxy compound is not particularly limited as long as it has an epoxy group, and may be a low molecular weight compound or a high molecular weight compound such as a resin. In particular, a polyfunctional epoxy compound is preferred in order to obtain a coating film with a high crosslinking density.

The weight average molecular weight of the epoxy compound is preferably 200 or more and 100,000 or less, more preferably 300 or more and 10,000 or less, and further preferably 500 or more and 5,000 or less.

As the epoxy compound, bisphenol A type epoxy compounds, bisphenol F type epoxy compounds, cresol novolac type epoxy compounds, biphenyl type epoxy compounds, alicyclic epoxy compounds, etc. can be used. Novolac type epoxy compounds and alicyclic epoxy compounds are preferred, and alicyclic epoxy compounds are particularly preferred. The functional group is preferably difunctional or higher, and is more preferably trifunctional or higher in terms of excellent thermal crosslinking properties.

Examples of difunctional epoxy compounds include EPICLON 830, 840, 850, 860, 1050, 2050, 3050, 4050, 7050, HM-091, and 101 manufactured by DIC; and Denacol EX-211, 212, 252, 711, and 721 manufactured by Nagase ChemteX.

As polyfunctional epoxy compounds having three or more functions, there are novolac epoxy compounds, and EHPE3150 (manufactured by Daicel Chemical Industries) as a high molecular weight alicyclic main chain epoxy compound. Specifically, novolac epoxy compounds include: EOCN-1020, EOCN-102S, EOCN-103S, EOCN-104S, EOCN-4500, EOCN-4600, XD-1000, XD-1000-L, XD-1000-2L, NC-3000, NC-3000-H (all manufactured by Nippon Kayaku Co., Ltd.); YDPN-638, YDCN-700-2, YDCN-700-3 , YDCN-700-5, YDCN-700-7, YDCN-700-10, YDCN-704, YDCN-704A (all manufactured by Nippon Steel Chemical Co., Ltd.); N-660, N-665, N-670, N-673, N-680, N-690, N-695, N-665-EXP, N-672-EXP, N-655-EXP-S, N-662-EXP-S (all manufactured by DIC Corporation), etc. In addition, as a trifunctional epoxy compound, Techmore VG3101 (manufactured by Printec), as a tetrafunctional epoxy compound, TETRAD-C, TETRAD-X (manufactured by Mitsubishi Gas Chemical Co., Ltd.), etc. can also be cited. In addition, Denacol EX-313, 314, 321, 411, 421, 512, 521, 611, 612, 614, 614B, 622, etc. manufactured by Nagase ChemteX can also be cited. In addition, JER1031S, 1302H60, 604, 630, 630LSD, etc. manufactured by Mitsubishi Chemical can also be cited.

<Organic solvent> The coloring composition of the present invention contains an organic solvent in order to facilitate the following operation: the coloring agent is fully dispersed and impregnated in the coloring agent carrier, and is applied on a substrate such as a glass substrate in a manner such that the dry film thickness becomes 0.2 μm to 5 μm to form a colored film. In addition to considering the good coating properties of the coloring composition, the organic solvent is selected in consideration of the solubility and safety of each component of the coloring composition.

Examples of the organic solvent include ethyl lactate, benzyl alcohol, 1,3-butanediol, 1,3-butylene glycol, 1,3-butanediol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3-propanediol, 3,5,5-trimethyl-2-cyclohexene-1-one, 3,3,5-trimethylcyclohexanone, 3-ethoxyethyl propionate, 3-methyl-1,3-butanediol, 3-methoxy-3-methyl-1-butanol, 3-methoxy-3-methylbutyl acetate, 3-methoxybutanol, 3-methoxybutyl acetate, 4-heptanone. , m-xylene, m-diethylbenzene, N,N-dimethylacetamide, N,N-dimethylformamide, n-butanol, n-butylbenzene, n-propyl acetate, o-xylene, o-diethylbenzene, p-diethylbenzene, 2-butylbenzene, 3-butylbenzene, γ-butyrolactone, isobutanol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotert-butyl ether, ethylene glycol monobutyl ether, ethylene glycol monobutyl ether acetate, Ethylene glycol monopropyl ether, ethylene glycol monohexyl ether, ethylene glycol monomethyl ether, ethylene glycol monomethyl ether acetate, diisobutyl ketone, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol monoisopropyl ether, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether, diethylene glycol monobutyl ether acetate, diethylene glycol monomethyl ether, cyclohexanol, cyclohexanol acetate, cyclohexanone, dipropylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, di Propylene glycol monomethyl ether, diacetone alcohol, triacetin, tripropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, propylene glycol diacetate, propylene glycol phenyl ether, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether, propylene glycol monopropyl ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monomethyl ether propionate, benzyl alcohol, methyl isobutyl ketone, methyl cyclohexanol, n-amyl acetate, n-butyl acetate, isoamyl acetate, isobutyl acetate, propyl acetate, dibasic acid esters, etc. These solvents may be used alone or two or more may be mixed in any ratio as needed.

Among them, in terms of good dispersibility and permeability of the colorant and good coating properties of the coloring composition, it is preferred to use ethylene glycol acetates such as ethyl lactate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, alcohols such as benzyl alcohol, diacetone alcohol, 3-methoxybutanol, propylene glycol monomethyl ether, or ketones such as cyclohexanone.

The organic solvent is preferably used in an amount of 500 to 4000 parts by mass based on 100 parts by mass of the coloring agent in order to adjust the coloring composition to an appropriate viscosity and form a colored film of the desired uniform film thickness.

<Photopolymerizable monomer> The coloring composition of the present invention contains a photopolymerizable monomer as an essential component. The photopolymerizable monomer includes a monomer or oligomer that is cured by ultraviolet light or heat to generate a transparent resin.

Examples of monomers and oligomers that are cured by ultraviolet light or heat to form a transparent resin include methyl (meth)acrylate, ethyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, cyclohexyl (meth)acrylate, β-carboxyethyl (meth)acrylate, polyethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate, triethylene glycol di(meth)acrylate, tripropylene glycol di(meth)acrylate, trihydroxymethylpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, and 1,6-hexanediol diglycidyl ether di(meth)acrylate. , bisphenol A diglycidyl ether di(meth)acrylate, neopentyl glycol diglycidyl ether di(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, tricyclodecyl (meth)acrylate, ester acrylate, hydroxymethylated melamine (meth)acrylate, epoxy (meth)acrylate, urethane acrylate and other acrylates and methacrylates, (meth)acrylic acid, styrene, vinyl acetate, hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth)acrylamide, N-hydroxymethyl (meth)acrylamide, N-vinylformamide, acrylonitrile, etc., but not necessarily limited to these. These photopolymerizable compounds can be used alone or two or more can be mixed in any ratio as needed.

The amount of the photopolymerizable monomer to be added is preferably 5 to 400 parts by mass based on the total mass of the colorant (100 parts by mass), and more preferably 10 to 300 parts by mass from the viewpoint of photocurability and developing properties.

<Photopolymerization initiator> The coloring composition of the present invention contains a photopolymerization initiator in order to harden the composition by ultraviolet irradiation and form a filter segment by photodevelopment. In addition, it can be prepared in the form of a solvent-developable or alkali-developable photosensitive coloring composition.

As the photopolymerization initiator, acetophenone compounds such as 4-phenoxydichloroacetophenone, 4-tert-butyl-dichloroacetophenone, diethoxyacetophenone, 1-(4-isopropylphenyl)-2-hydroxy-2-methylpropane-1-one, 1-hydroxycyclohexylphenyl ketone, 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinopropane-1-one, 2-(dimethylamino)-2-[(4-methylphenyl)methyl]-1-[4-(4-morpholino)phenyl]-1-butanone or 2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butane-1-one can be used; benzoin, benzoin methyl ester ... Benzoin compounds such as benzoyl ether, benzoin ethyl ether, benzoin isopropyl ether or benzyl dimethyl ketal; benzophenone compounds such as benzoylbenzoic acid, benzoylbenzoic acid methyl ester, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4'-methyldiphenyl sulfide or 3,3',4,4'-tetra(tert-butylperoxycarbonyl)benzophenone; thioxanthrone compounds such as 2-chlorothioxanthrone, 2-methylthioxanthrone, isopropylthioxanthrone, 2,4-diisopropylthioxanthrone or 2,4-diethylthioxanthrone; 2,4,6-trichloro-s-triazine , 2-phenyl-4,6-bis(trichloromethyl)-s-triazine, 2-(p-methoxyphenyl)-4,6-bis(trichloromethyl)-s-triazine, 2-(p-tolyl)-4,6-bis(trichloromethyl)-s-triazine, 2-piperonyl-4,6-bis(trichloromethyl)-s-triazine, 2,4-bis(trichloromethyl)-6-phenylvinyl-s-triazine, 2-(naphthalen-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2-(4-methoxy-naphthalen-1-yl)-4,6-bis(trichloromethyl)-s-triazine, 2,4-trichloromethyl-(piperonyl)-6-triazine or 2,4-trichloromethyl-(4' -methoxyphenylvinyl)-6-triazine and other triazine compounds; oxime ester compounds such as 1,2-octanedione, 1-[4-(phenylthio)-, 2-(O-benzoyl oxime)] or O-(acetyl)-N-(1-phenyl-2-oxo-2-(4'-methoxy-naphthyl)ethylidene)hydroxylamine; phosphine compounds such as bis(2,4,6-trimethylbenzyl)phenylphosphine oxide or 2,4,6-trimethylbenzyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone, ethylanthraquinone; borate ester compounds; oxazole compounds; imidazole compounds; or titanocene compounds, etc. These photopolymerization initiators can be used alone or two or more can be mixed in any ratio as needed.

The content of the photopolymerization initiator is preferably 2 to 200 parts by mass based on 100 parts by mass of the coloring agent, and more preferably 3 to 150 parts by mass from the viewpoint of photocurability and developing properties.

<Sensitizer> Furthermore, the coloring composition of the present invention may contain a sensitizer. As sensitizers, there can be listed: chalcone derivatives, unsaturated ketones represented by dibenzalacetone, 1,2-diketone derivatives represented by benzoyl or camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives, oxanthracene derivatives, thioanthracene derivatives, oxanthrone derivatives, thioanthrone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxocyanine derivatives and other polymethine pigments, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, azulene derivatives, azulenium derivatives, squarylium derivatives, porphyrin derivatives a tetraphenylporphyrin derivative, a triarylmethane derivative, a tetrabenzoporphyrin derivative, a tetrapyrazinoporphyrazine derivative, a phthalocyanine derivative, a tetraazaporphyrazine derivative, a tetraquinoporphyrazine derivative, a naphthalocyanine derivative, a subphthalocyanine derivative, a pyrylium derivative, a thiopyrylium derivative, a tetraphyrin derivative, an annulene derivative, a spiropyran derivative, a spirooxazine derivative, a thiospiropyran derivative, a metal aromatic complex, an organic ruthenium complex or Michler's ketone. ketone derivatives, biimidazole derivatives, α-acyloxy esters, acylphosphine oxides, methyl phenyl glyoxylate, benzoyl, 9,10-phenanthrenequinone, camphorquinone, ethyl anthraquinone, 4,4'-diethyl isophthalophenone, 3,3'-tetra(tert-butylperoxycarbonyl)benzophenone or 4,4'-tetra(tert-butylperoxycarbonyl)benzophenone, 4,4'-diethylaminobenzophenone, etc. These sensitizers can be used alone or in combination of two or more in any ratio as needed.

Furthermore, specifically, the sensitizers described in "Pigment Handbook" (1986, Kodan Co., Ltd.) compiled by Ohkawara Nobuyuki et al., "Chemistry of Functional Pigments" (1981, CMC) compiled by Ohkawara Nobuyuki et al., and "Special Functional Materials" (1986, CMC) compiled by Ikemori Tadazaburō et al. can be cited, but the present invention is not limited to these. In addition, a sensitizer that shows absorption to light in the ultraviolet to near-infrared region may also be contained.

The content of the sensitizer is preferably 3 to 60 parts by mass based on 100 parts by mass of the photopolymerization initiator contained in the coloring composition, and more preferably 5 to 50 parts by mass from the viewpoint of photocurability and developing properties.

<Thiol compound> The coloring composition of the present invention may contain a thiol compound that functions as a chain transfer agent. As the thiol compound, a polyfunctional thiol compound having two or more thiol groups is preferred, for example, hexane dithiol, decanedithiol, 1,4-butanediol bisthiopropionate, 1,4-butanediol bisthioglycolate, ethylene glycol bisthioglycolate, ethylene glycol bisthiopropionate, trihydroxymethylpropane trithioglycolate, trihydroxymethylpropane trithiopropionate, trihydroxymethylpropane tris(3-butylbutyrate), pentaerythritol tetrathioglycolate, pentaerythritol tetrathiopropionate, tris(2-hydroxyethyl) isocyanurate of tris(butylene)propionate, 1,4-dimethylbutylbenzene, 2,4,6-tris(butylene)-s-triazine, 2-(N,N-dibutylamino)-4,6-dibutyl-s-triazine, etc. These polyfunctional thiol compounds may be used alone or in combination of two or more at any ratio as required.

The content of the thiol compound is preferably 0.1% to 30% by mass, and more preferably 0.1% to 20% by mass, based on the total solid content of the color filter coloring composition (100% by mass). If the content of the thiol compound is less than 0.1% by mass, the effect of adding the thiol compound is insufficient, and if it exceeds 30% by mass, the following situation may occur: the sensitivity is too high, and the resolution is reduced.

<Antioxidant> The coloring composition of the present invention may contain an antioxidant. The antioxidant prevents the photopolymerization initiator or thermosetting compound contained in the coloring composition from being oxidized and yellowed during the heat step of heat curing or annealing of indium tin oxide (ITO), thereby improving the transmittance of the coating film. Therefore, by including an antioxidant, yellowing caused by oxidation during the heating step can be prevented and a high transmittance of the coating film can be obtained.

The so-called "antioxidant" in the present invention is any compound that has ultraviolet absorption function, free radical scavenging function or peroxide decomposition function. Specifically, as antioxidants, hindered phenol-based, hindered amine-based, phosphorus-based, sulfur-based, benzotriazole-based, benzophenone-based, hydroxylamine-based, salicylic acid ester-based and triazine-based compounds can be listed. Well-known ultraviolet absorbers, antioxidants, etc. can be used.

Among these antioxidants, from the viewpoint of achieving both permeability and sensitivity of the coating, preferred antioxidants include hindered phenol antioxidants, hindered amine antioxidants, phosphorus antioxidants, and sulfur antioxidants. In addition, hindered phenol antioxidants, hindered amine antioxidants, and phosphorus antioxidants are more preferred.

These antioxidants may be used alone or in combination of two or more at any ratio as needed.

When the content of the antioxidant is 0.1 mass % to 5.0 mass % based on the solid content mass of the coloring composition for a color filter (100 mass %), brightness and sensitivity are good, which is more preferred.

<Amine compounds> In addition, the coloring composition of the present invention may contain an amine compound having the function of reducing dissolved oxygen. Examples of such amine compounds include triethanolamine, methyldiethanolamine, triisopropanolamine, methyl 4-dimethylaminobenzoate, ethyl 4-dimethylaminobenzoate, isoamyl 4-dimethylaminobenzoate, 2-dimethylaminoethyl benzoate, 2-ethylhexyl 4-dimethylaminobenzoate, and N,N-dimethyl-p-toluidine.

<Leveling agent> In order to improve the leveling property of the composition on the transparent substrate, a leveling agent may be added to the coloring composition of the present invention. As the leveling agent, dimethylsiloxane having a polyether structure or a polyester structure in the main chain is preferred. Specific examples of dimethylsiloxane having a polyether structure in the main chain include FZ-2122 manufactured by Toray Dow Corning and BYK-333 manufactured by BYK-Chemie. Specific examples of dimethylsiloxane having a polyester structure in the main chain include BYK-310 and BYK-370 manufactured by BYK-Chemie. Dimethylsiloxane with a polyether structure in the main chain and dimethylsiloxane with a polyester structure in the main chain can also be used together. Based on the total mass of the coloring composition (100 mass%), the content of the leveling agent is usually preferably 0.003 mass% to 0.5 mass%.

A particularly preferred leveling agent is a so-called surfactant having a hydrophobic group and a hydrophilic group in the molecule, and a useful leveling agent has the characteristics of low solubility in water despite containing a hydrophilic group, low surface tension reduction ability when added to a coloring composition, and good wettability to a glass plate even with low surface tension reduction ability. A leveling agent that can sufficiently suppress charging at an addition amount that does not cause coating defects due to bubbling can be preferably used. As a leveling agent having such preferred characteristics, dimethyl polysiloxane having a polyalkylene oxide unit can be preferably used. The polyalkylene oxide unit includes a polyethylene oxide unit and a polypropylene oxide unit. Dimethylpolysiloxane may contain both polyethylene oxide units and polypropylene oxide units.

In addition, the bonding form of the polyoxyalkylene unit with dimethylpolysiloxane may be any of a pendant type in which the polyoxyalkylene unit is bonded to the repeating unit of dimethylpolysiloxane, a terminal-modified type in which the polyoxyalkylene unit is bonded to the terminal of dimethylpolysiloxane, and a linear block copolymer type in which the polyoxyalkylene unit is alternately and repeatedly bonded to dimethylpolysiloxane. Dimethylpolysiloxane having polyoxyalkylene units is commercially available from Toray Dow Corning Co., Ltd., for example, FZ-2110, FZ-2122, FZ-2130, FZ-2166, FZ-2191, FZ-2203, and FZ-2207, but is not limited thereto.

Anionic, cationic, nonionic or amphoteric surfactants can also be added to the leveling agent as an auxiliary agent. Two or more surfactants can be mixed and used. Anionic surfactants added to the leveling agent as an auxiliary agent include: polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium alkyl naphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, sodium stearate, sodium lauryl sulfate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate, etc.

As cationic surfactants added to the leveling agent as an auxiliary, alkyl quaternary ammonium salts or ethylene oxide adducts thereof can be listed. As nonionic surfactants added to the leveling agent as an auxiliary, polyoxyethylene oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate and other polyoxyalkylene surfactants; alkyl betaines such as alkyl dimethylaminoacetic acid betaine, alkyl imidazoline and other amphoteric surfactants; and fluorine or silicone surfactants.

<Hardener, Hardening Accelerator> In addition, in order to assist the hardening of the thermosetting resin, the coloring composition of the present invention may also contain a hardener, a hardening accelerator, etc. as needed. As a hardener, phenolic resins, amine compounds, acid anhydrides, active esters, carboxylic acid compounds, sulfonic acid compounds, etc. are effective, but are not particularly limited to these. As long as it is a hardener that can react with the thermosetting resin, any hardener can be used. In addition, among these, compounds having two or more phenolic hydroxyl groups in one molecule and amine hardeners can be preferably listed. As the hardening accelerator, for example, amine compounds (e.g., dicyandiamide, benzyldimethylamine, 4-(dimethylamino)-N,N-dimethylbenzylamine, 4-methoxy-N,N-dimethylbenzylamine, 4-methyl-N,N-dimethylbenzylamine, etc.), quaternary ammonium salt compounds (e.g., triethylbenzylammonium chloride, etc.), blocked isocyanate compounds (e.g., dimethylamine, etc.), imidazole derivatives, bicyclic amidine compounds and their salts (e.g., imidazole, 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-phenylimidazole, 4-phenylimidazole, 1-cyano ethyl-2-phenylimidazole, 1-(2-cyanoethyl)-2-ethyl-4-methylimidazole, etc.), phosphorus compounds (such as triphenylphosphine, etc.), guanamine compounds (such as melamine, guanamine, acetoguanamine, benzoguanamine, etc.), S-triazine derivatives (such as 2,4-diamino-6-methacryloyloxyethyl-S-triazine, 2-vinyl-2,4-diamino-S-triazine, 2-vinyl-4,6-diamino-S-triazine·isocyanuric acid adduct, 2,4-diamino-6-methacryloyloxyethyl-S-triazine·isocyanuric acid adduct, etc.). These may be used alone or in combination of two or more. The content of the curing accelerator is preferably 0.01 to 15 parts by mass relative to 100 parts by mass of the thermosetting resin.

<Other additive components> In order to stabilize the viscosity over time, the coloring composition of the present invention may contain a storage stabilizer. In addition, in order to improve the adhesion with the transparent substrate, it may also contain an adhesion enhancer such as a silane coupling agent.

Examples of the storage stabilizer include quaternary ammonium chlorides such as benzyltrimethylammonium chloride and diethylhydroxylamine; organic acids such as lactic acid and oxalic acid and their methyl ethers; tert-butyl catechol; organic phosphines such as tetraethylphosphine and tetraphenylphosphine; phosphites, etc. The storage stabilizer can be used in an amount of 0.1 to 10 parts by mass relative to 100 parts by mass of the coloring agent.

Examples of the adhesion enhancer include vinyl silanes such as vinyl tri(β-methoxyethoxy) silane, vinyl ethoxy silane, and vinyl trimethoxy silane; (meth) acrylic silanes such as γ-methacryloyloxypropyl trimethoxy silane; β-(3,4-epoxycyclohexyl)ethyl trimethoxy silane, β-(3,4-epoxycyclohexyl)methyl trimethoxy silane, β-(3,4-epoxycyclohexyl)ethyl triethoxy silane, β-(3,4-epoxycyclohexyl)methyl triethoxy silane, γ-glycidyloxypropyl trimethoxy silane, γ-glycidyloxypropyl trimethoxy silane, and γ-glycidyloxypropyl trimethoxy silane. Silane coupling agents include thiosilanes such as γ-butyltriethoxysilane and γ-butyltriethoxysilane; aminosilanes such as N-β (aminoethyl) γ-aminopropyltrimethoxysilane, N-β (aminoethyl) γ-aminopropyltriethoxysilane, N-β (aminoethyl) γ-aminopropylmethyldiethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane, and N-phenyl-γ-aminopropyltriethoxysilane; silane coupling agents such as thiosilanes such as γ-butylpropyltrimethoxysilane and γ-butylpropyltriethoxysilane. The adhesion improver can be used in an amount of 0.01 to 10 parts by mass, preferably 0.05 to 5 parts by mass, based on 100 parts by mass of the coloring agent in the coloring composition.

<Method for producing coloring composition> The coloring composition of the present invention is preferably produced by finely dispersing the coloring agent [A] together with a dispersing aid such as a pigment dispersant or a resin type dispersant in a coloring agent carrier such as a resin and/or a solvent using various dispersing means such as a kneader, a double-roll mill, a three-roll mill, a ball mill, a horizontal sand mill, a vertical sand mill, a ring-shaped bead mill or a grinding mill (coloring agent dispersion). At this time, two or more coloring agents may be dispersed in the coloring agent carrier at the same time, or the coloring agents dispersed in the coloring agent carriers may be mixed. When the solubility of a coloring agent such as a dye is high, specifically, when it is highly soluble in the solvent used and is dissolved by stirring without foreign matter being observed, it is not necessary to produce it by fine dispersion as described above.

In addition, when used as a photosensitive coloring composition (anti-corrosion material), it can be prepared as a solvent-developable or alkali-developable coloring composition. The solvent-developable or alkali-developable coloring composition can be prepared by mixing the coloring agent dispersion, photopolymerizable monomer and/or photopolymerization initiator, a solvent as required, other dispersing aids and additives, etc. The photopolymerization initiator can be added during the preparation of the coloring composition, or can be added to the prepared coloring composition afterwards.

<Dispersing aid> When dispersing the colorant in the colorant carrier, a dispersing aid such as a pigment dispersant, a resin dispersant, or a surfactant may be appropriately contained. The dispersing aid has a great effect of preventing the re-aggregation of the dispersed colorant, so the coloring composition obtained by dispersing the colorant in the colorant carrier using the dispersing aid has good brightness and viscosity stability. The pigment dispersant and the resin dispersant are as described above.

＜Surfactant＞ As surfactants, there are anionic surfactants such as sodium lauryl sulfate, polyoxyethylene alkyl ether sulfate, sodium dodecylbenzene sulfonate, alkali salt of styrene-acrylic acid copolymer, sodium stearate, sodium alkylnaphthalene sulfonate, sodium alkyl diphenyl ether disulfonate, monoethanolamine lauryl sulfate, triethanolamine lauryl sulfate, ammonium lauryl sulfate, monoethanolamine stearate, monoethanolamine of styrene-acrylic acid copolymer, polyoxyethylene alkyl ether phosphate ester, etc.; polyoxyethylene Nonionic surfactants such as oleyl ether, polyoxyethylene lauryl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene alkyl ether phosphate, polyoxyethylene sorbitan monostearate, polyethylene glycol monolaurate; cationic surfactants such as alkyl quaternary ammonium salts or ethylene oxide adducts thereof; alkyl betaines such as alkyl dimethylaminoacetic acid betaine, amphoteric surfactants such as alkyl imidazolines, these may be used alone or in combination of two or more, but are not necessarily limited to these.

When a surfactant is added, the amount is preferably 0.1 to 55 parts by mass, and more preferably 0.1 to 45 parts by mass, relative to 100 parts by mass of the coloring agent. If the amount of the surfactant is less than 0.1 parts by mass, it is difficult to obtain the effect after addition, and if the content is more than 55 parts by mass, there is a situation in which the dispersion is affected by the excess dispersant.

<Removal of coarse particles> The color filter of the present invention preferably removes coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, and preferably coarse particles of 0.5 μm or more, and the dust mixed therein by centrifugal separation, filtering using a sintered filter or a membrane filter, etc. As described above, the coloring composition preferably does not substantially contain particles of 0.5 μm or more. More preferably, it is 0.3 μm or less.

<Color filter> Next, the color filter of the present invention is described. The color filter of the present invention includes a red filter segment, a green filter segment, and a blue filter segment. In addition, the color filter may also include a magenta filter segment, a cyan filter segment, and a yellow filter segment. Regarding the color filter of the present invention, at least one of the red filter segment, the green filter segment, and the yellow filter segment is formed by the pigment composition of the present invention. It is particularly preferred that the red filter segment is formed by the pigment composition of the present invention.

<Method for manufacturing color filters> Color filters can be manufactured by printing or photodevelopment. Regarding the formation of filter segments by printing, patterning can be achieved by simply repeating the printing and drying of a coloring composition prepared as printing ink, so it is a low-cost and mass-productive method for manufacturing color filters. Furthermore, due to the development of printing technology, fine patterns with high dimensional accuracy and smoothness can be printed. In order to print, it is preferable to use a composition that does not dry or solidify the ink on the printing plate or blanket. In addition, it is also important to control the fluidity of the ink on the printing machine, and the viscosity of the ink can be adjusted by using a dispersant or a body pigment.

When the filter segment is formed by the optical development method, the coloring composition prepared as the solvent-developable or alkali-developable coloring resist is applied to the transparent substrate by a coating method such as spray coating, rotary coating, slit coating, roll coating, etc., so that the dry film thickness becomes 0.2 μm to 5 μm. The film dried as necessary is exposed (irradiated with radiation) through a mask having a predetermined pattern placed in contact with or not in contact with the film. After that, the uncured part is removed by immersing in a solvent or alkaline developer, or spraying the developer by spraying, etc., to form a desired pattern, and then the same operation is repeated for other colors to produce a color filter. Furthermore, in order to promote the polymerization of the colored anti-etching agent material, heating may be applied as needed. According to the optical development method, a color filter with higher precision can be produced than the above-mentioned printing method.

During development, an aqueous solution of sodium carbonate, sodium hydroxide, etc., or an organic base such as dimethylbenzylamine, triethanolamine, etc. may be used as an alkaline developer. In addition, a defoamer or a surfactant may be added to the developer. Furthermore, in order to improve the exposure sensitivity, after the colored anti-etching agent is applied and dried, a water-soluble or alkaline water-soluble resin, such as polyvinyl alcohol or a water-soluble acrylic resin, may be applied and dried to form a film to prevent polymerization hindrance caused by oxygen, and then exposure may be performed.

In addition to the above methods, the color filter of the present invention can also be manufactured by electroplating, transfer, inkjet, etc., and the coloring composition of the present invention can also be used in any of the methods. Furthermore, the electroplating method is a method in which a transparent conductive film formed on a substrate is used to electroplating and forming filter segments of various colors on the transparent conductive film by electrophoresis of colloidal particles, thereby manufacturing a color filter. In addition, the transfer method is a method in which filter segments are preliminarily formed on the surface of a releasable transfer base sheet, and the filter segments are transferred to a desired substrate.

Before forming the color filter segments on the transparent substrate or the reflective substrate, a black matrix may be formed in advance. As the black matrix, a multi-layer film of chromium or chromium/chromium oxide, an inorganic film such as titanium nitride, or a resin film dispersed with a light shielding agent may be used, but it is not limited to these. In addition, a thin film transistor (TFT) may be formed in advance on the transparent substrate or the reflective substrate, and then the color filter segments may be formed. In addition, an overcoat film or a transparent conductive film may be formed on the color filter of the present invention as needed.

The color filter of the present invention is bonded to the opposite substrate using a sealant, and liquid crystal is injected from an injection port provided in the sealing portion, and then the injection port is sealed, and a polarizing film or a phase difference film is bonded to the outer side of the substrate as needed, thereby manufacturing a color liquid crystal display device. The color liquid crystal display device can be used in a liquid crystal display mode that uses a color filter to perform colorization, such as twisted nematic (TN), super twisted nematic (STN), in-plane switching (IPS), vertically aligned (VA), optically compensated bend (OCB), etc.

In addition, the color filter of the present invention can be used not only for manufacturing color liquid crystal display devices, but also for manufacturing color imaging elements, organic EL display devices, electronic paper, etc. [Example]

Hereinafter, the present invention will be described based on the examples, but the present invention is not limited thereto. In the examples and comparative examples, the so-called "parts" refers to "parts by mass".

(Weight average molecular weight (Mw) of resin) The weight average molecular weight (Mw) of the resin is the weight average molecular weight (Mw) in terms of polystyrene measured using a TSKgel column (manufactured by Tosoh Corporation) and a gel permeation chromatograph (GPC) (manufactured by Tosoh Corporation, HLC-8120GPC) equipped with an RI detector, and using tetrahydrofuran (THF) as a developing solvent.

Next, the production methods of the resin solutions, resin dispersant solutions, pigment dispersants, and pigment compositions used in the Examples and Comparative Examples are described.

<Production of acrylic resin solution> (Preparation of acrylic resin solution 1) Into a reaction container equipped with a thermometer, a cooling tube, a nitrogen inlet tube, and a stirring device in a separable four-necked flask, 100 parts of propylene glycol monomethyl ether acetate were placed, and while nitrogen was injected into the container, it was heated to 120°C. At the above temperature, a mixture of 16.2 parts of styrene, 35.5 parts of glycidyl methacrylate, 25.0 parts of dicyclopentyl methacrylate, 16 parts of methyl methacrylate, and 1.0 part of azobisisobutyronitrile as a catalyst required for the reaction of the precursors in this stage was dripped from the dripping tube over 2.5 hours to carry out a polymerization reaction. Next, the atmosphere in the flask was replaced with air, and 17.0 parts of acrylic acid and 0.3 parts of tris-dimethylaminomethylphenol and 0.3 parts of hydroquinone as catalysts required for the reaction of the precursor in this stage were added, and the reaction was carried out at 120°C for 5 hours to obtain a resin solution with a weight average molecular weight of about 12,000 (measured by GPC). The acrylic acid added was ester-bonded with the epoxide terminal of the glycidyl methacrylate constituent unit, so no carboxyl group was generated in the resin structure. Furthermore, 30.4 parts of tetrahydrophthalic anhydride and 0.5 parts of triethylamine as a catalyst required for the reaction of the precursor in this stage were added, and the reaction was carried out at 120°C for 4 hours. One of the two carboxyl groups generated by the cleavage of the carboxylic anhydride site of the added tetrahydrophthalic anhydride forms an ester bond with the hydroxyl group in the resin structure, and the other forms a carboxyl terminal. Propylene glycol monomethyl ether acetate is added so that the non-volatile component becomes 20%, thereby obtaining an acrylic resin solution 1.

(Preparation of acrylic resin solution 2) Into a separable flask equipped with a cooling tube, 100 parts by mass of propylene glycol monomethyl ether acetate was placed, the atmosphere was replaced with nitrogen, and the temperature was raised to 90°C. On the other hand, in the dropping tank 1, 10.0 parts of dimethyl-2,2'-[oxybis(methylenebis)]-2-propionate, 40.1 parts of cyclohexyl methacrylate, 24.2 parts of tetrahydrofurfuryl methacrylate, 24.7 parts of methacrylic acid, 2.0 parts of tert-butyl peroxy-2-ethylhexanoate, and 80 parts of propylene glycol monomethyl ether acetate were mixed. In addition, 3.1 parts of β-butyl propionic acid and 6 parts of propylene glycol monomethyl ether acetate were mixed in the dropping tank 2. While the reaction temperature was maintained at 90°C, the reaction was dripped from the dripping tank 1 and the dripping tank 2 into the reaction tank at a constant rate over 2.5 hours. After the dripping was completed, the temperature was maintained at 90°C for 30 minutes, and then 0.5 parts of tert-butyl peroxy-2-ethylhexanoate was added, and the reaction was continued at 90°C for 30 minutes. Thereafter, the reaction temperature was raised to 115°C, and the reaction was continued for 1.5 hours. After temporarily cooling to room temperature, 24.7 parts of glycidyl methacrylate, 0.038 parts of 6-tert-butyl-2,4-dimethylphenol, and 0.38 parts of dimethylbenzylamine were added, and a nitrogen-air mixed gas adjusted to an oxygen concentration of 7% was bubbled, and the temperature was raised to 110°C, and the reaction was carried out for 6 hours. Thereafter, the temperature was raised to 115°C and the reaction was carried out for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, and about 2 g of the resin solution was sampled and dried by heating at 180°C for 20 minutes. The non-volatile components were measured, and propylene glycol monomethyl ether acetate was added to the previously synthesized resin solution in such a manner that the non-volatile components became 40% by mass, thereby obtaining an acrylic resin solution 2. The weight average molecular weight of the resin was 9000, and the acid value per unit solid component was 70 mgKOH/g.

<Preparation of resin dispersant solution> (Preparation of resin dispersant solution 1) Into a flask equipped with a cooling tube and a stirrer, 1.0 parts by mass of 2,2'-azobisisobutyronitrile (AIBN) and 186 parts by mass of propylene glycol monomethyl ether acetate were charged, followed by 27 parts by mass of methyl methacrylate, 27 parts by mass of butyl methacrylate, 21 parts by mass of 2-ethylhexyl methacrylate, 18 parts by mass of benzyl methacrylate, and 3.6 parts by mass of cumyl dithiobenzoate, and nitrogen substitution was performed for 30 minutes. Thereafter, the temperature of the reaction solution was raised to 60°C while stirring slowly, and the temperature was maintained for 24 hours to perform living radical polymerization. Next, a solution prepared by dissolving 1.0 parts by mass of AIBN and 35 parts by mass of dimethylaminoethyl methacrylate in 70 parts by mass of propylene glycol monomethyl ether acetate and replacing the atmosphere with nitrogen for 30 minutes was added to the reaction solution, and living radical polymerization was performed at 60° C. for 24 hours to obtain a block copolymer solution. 25 parts by mass of benzyl chloride and 50 parts by mass of propylene glycol monomethyl ether were added to the obtained block copolymer solution, and the reaction was performed at 80° C. for 2 hours to adjust the solid content concentration to 40%, thereby obtaining a resin-type dispersant solution 1. Resin-type dispersant 1 is a block copolymer including an A block and a B block, wherein the A block has repeating units derived from methacryloyloxyethylbenzyldimethylammonium chloride and dimethylaminoethyl methacrylate, and the B block has repeating units derived from methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, and benzyl methacrylate. As a result of proton nuclear magnetic resonance (NMR) measurement, the copolymerization ratio of each repeating unit is methacryloyloxyethylbenzyldimethylammonium chloride/dimethylaminoethyl methacrylate/methyl methacrylate/butyl methacrylate/2-ethylhexyl methacrylate/benzyl methacrylate = 34/4/18/18/14/12 (mass ratio).

(Preparation of resin dispersant solution 2) Into a reaction vessel including a gas inlet tube, a thermometer, a condenser, and a stirrer, 6.5 parts of 3-hydroxy-1,2-propanediol, 4.0 parts of pyromellitic anhydride, 0.01 parts of dimethylbenzylamine, and 41.8 parts of methoxypropyl acetate were placed, and replaced with nitrogen. The reaction vessel was heated to 100°C and reacted for 7 hours. The acid value was measured to confirm that more than 98% of the anhydride was half-esterified, and then the temperature in the system was cooled to 70°C, and 67 parts of methyl methacrylate, 5.0 parts of methacrylic acid, 16.0 parts of tert-butyl acrylate, 10.0 parts of (3-ethyloxycyclobutane-3-yl)methyl methacrylate, and 2.0 parts of ethyl acrylate were added, and 0.10 parts of 2,2'-azobisisobutyronitrile and 60.0 parts of methoxypropyl acetate were added, and the reaction was carried out for 10 hours. The solid content was measured to confirm that 95% of the polymerization was carried out, and the reaction was terminated, thereby obtaining a polyester dispersant with an acid value of 47 mgKOH/g and a number average molecular weight of 15,000. Methoxypropyl acetate was added thereto so that the solid content became 40% as determined by solid content measurement, thereby obtaining a resin-type dispersant solution 2 having an aromatic carboxyl group.

＜Manufacturing of pigment dispersion＞

(Manufacturing of Pigment Dispersant A) Pigment dispersant A represented by the following structure was manufactured with reference to Synthesis Example 3 of Japanese Patent No. 5748665.

Pigment dispersant A [Chemical 19]

(Manufacturing of Pigment Dispersant B) Pigment dispersant B having the following structure was manufactured with reference to Manufacturing Example 6 of Japanese Patent No. 4983061.

Pigment dispersant B [Chemical 20]

(Manufacturing of Pigment Dispersant C) Pigment dispersant C having the following structure was manufactured with reference to Manufacturing Example 2 of Japanese Patent Publication No. 2017-31330.

Pigment dispersant C [Chemical 21]

<Production of pigment composition> (Preparation of red pigment composition (P-1)) A mixture of 300 parts of diketopyrrolopyrrole red pigment (C.I. Pigment Red 254, BASF's "Irgazin RED L3630"), 1500 parts of sodium chloride and 150 parts of diethylene glycol was kneaded at 60°C for 6 hours using a 1-gallon stainless steel kneader (Inoue Seisakusho). The mixture was then poured into 5 liters of warm water and stirred for 1 hour while heating to 70°C to form a slurry. Filtering and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying and pulverization to obtain 290 parts of a red pigment composition P-1.

(Preparation of red pigment composition (P-2)) A mixture of 300 parts of diketopyrrolopyrrole red pigment (C.I. Pigment Red 291, Cinilex DPP MT-CF from CINIC) and 150 parts of diethylene glycol was kneaded at 60°C for 6 hours using a 1-gallon stainless steel kneader (Inoue Seisakusho). The mixture was then added to 5 liters of warm water and stirred for 1 hour while being heated to 70°C to form a slurry. Filtration and water washing were repeated to remove sodium chloride and diethylene glycol, followed by drying and pulverization to obtain 290 parts of red pigment composition P-2.

<Production of Pigment Dispersant of General Formula (1)> [Example 1] (Synthesis of Pigment Dispersant (2-1)) At room temperature, 30 parts of C.I. Pigment Red 272 ("Irgazin RED K3800" manufactured by BASF) were added to 300 parts of 102% fuming sulfuric acid. The mixture was stirred at room temperature for 3 hours and then added dropwise to 1500 parts of cold methyl ethyl ketone over 30 minutes. The precipitated disulfonic acid was filtered, washed with 3000 parts of ice methyl ethyl ketone, and dried at 80°C to obtain a disulfonic acid. 10 parts of the disulfonic acid were added to 100 parts of N,N-dimethylformamide, and 10 parts of sulfinyl chloride were slowly added dropwise. The reaction solution was heated to 60 degrees and stirred for 6 hours. The reaction solution was poured into 250 parts of ice and 250 parts of water, the precipitate was filtered, and washed three times with 500 parts of ice water to obtain a filter cake of chlorosulfonyl diketo pyrrolopyrrole. The filter cake was added into 300 parts of N,N-dimethylformamide and 5.6 parts of propylamine (manufactured by Tokyo Chemical Industry Co., Ltd.) and stirred for 3 hours. The mixed solution was poured into 1500 parts of methanol, the precipitate was filtered, washed with methanol and water, and dried at 80°C. Thus, a pigment dispersant (2-1) (10.8 parts) was obtained. The purity was determined by high performance liquid chromatography and was 98%.

The conditions for high performance liquid chromatography are shown below. Column: Symmetry C18 5micron (Waters, Japan) Eluent: (A) 0.05 mol/l CH ₃ COONH ₄ aqueous solution/N,N-dimethylformamide (DMF) = 7/1 (volume ratio) (B) N,N-dimethylformamide/water = 95/5 (volume ratio) Gradient conditions: After maintaining (A): (B) = 80/20 (volume ratio) for 5 minutes, it was changed from (A): (B) = 80/20 (volume ratio) to (A): (B) = 0/100 (volume ratio) over 20 minutes, and then maintained at (A): (B) = 0/100 (volume ratio) for 15 minutes. Flow rate: 0.300 ml/min Injection volume: 5 μl Column temperature: 35°C

[Example 2 to Example 35] (Synthesis of pigment dispersants (2-2 to 2-31), pigment dispersants (3-1, 3-2), and pigment dispersants (4-1, 4-2)) Pigment dispersants (2-2 to 2-31), pigment dispersants (3-1, 3-2), and pigment dispersants (4-1, 4-2) were obtained by the same method as in Example 1, except that C.I. Pigment Red 272 and 5.6 parts of propylamine were replaced with diketopyrrolopyrrole pigments and amines listed in Table 5 below.

In Examples 29 to 31, 34 and 35, diketopyrrolopyrrole (16) to diketopyrrolopyrrole (20) represented by the following formulae were used to obtain pigment dispersants (2-29 to 2-31) and pigment dispersants (4-1 and 4-2).

Formula (16) [22]

Formula (17) [Chemical 23]

Formula (18) [24]

Formula (19) [Chemical 25]

Formula (20) [Chemical 26]

[Table 5] Table 5 Pigment dispersant Diketopyrrolopyrrole amine Molecular weight Product Name Quantity (serving) Embodiment 1 (2-1) CI Pigment Red 272 Propylamine 5.6 558.7 Embodiment 2 (2-2) CI Pigment Red 272 Isobutylamine 6.9 586.8 Embodiment 3 (2-3) CI Pigment Red 272 tert-Butylamine 6.9 586.8 Embodiment 4 (2-4) CI Pigment Red 272 Octylamine 12.2 699.0 Embodiment 5 (2-5) CI Pigment Red 272 Stearylamine 25.5 979.5 Embodiment 6 (2-6) CI Pigment Red 272 2-Ethylhexylamine 12.2 699.0 Embodiment 7 (2-7) CI Pigment Red 272 2-Butyl-n-octan-1-amine 17.5 811.2 Embodiment 8 (2-8) CI Pigment Red 272 Diethylamine 6.9 586.8 Embodiment 9 (2-9) CI Pigment Red 272 Dipropylamine 9.6 642.9 Embodiment 10 (2-10) CI Pigment Red 272 Diamylamine 14.9 755.1 Embodiment 11 (2-11) CI Pigment Red 272 Dihexylamine 17.5 811.2 Embodiment 12 (2-12) CI Pigment Red 272 Didecylamine 28.1 1035.6 Embodiment 13 (2-13) CI Pigment Red 272 Diisoamylamine 14.9 755.1 Embodiment 14 (2-14) CI Pigment Red 272 Di(2-ethylhexyl)amine 22.8 923.4 Embodiment 15 (2-15) CI Pigment Red 272 N-ethylbutylamine 9.6 642.9 Embodiment 16 (2-16) CI Pigment Red 272 Bis(4-tert-butylphenyl)amine 26.6 1003.4 Embodiment 17 (2-17) CI Pigment Red 272 Dibenzylamine 18.6 835.0 Embodiment 18 (2-18) CI Pigment Red 272 3,6,9,12-Tetraoxatridecanamine 19.6 855.0 Embodiment 19 (2-19) CI Pigment Red 255 Isobutylamine 7.3 558.9 Embodiment 20 (2-20) CI Pigment Red 255 Diamylamine 15.8 727.2 Embodiment 21 (2-21) CI Pigment Red 254 2-Methylbutylamine 7.6 655.7 Embodiment 22 (2-22) CI Pigment Red 254 3-Isopropylaniline 11.8 751.7 Embodiment 23 (2-23) CI Pigment Red 264 Isoamylamine 6.5 739.0 Embodiment 24 (2-24) CI Pigment Red 264 4-Amylaniline 12.2 891.1 Embodiment 25 (2-25) CI Pigment Red 291 4-Heptylamine 8.6 800.7 Embodiment 26 (2-26) CI Pigment Red 291 3,4-Dimethylaniline 9.0 812.6 Embodiment 27 (2-27) CI pigment orange 73 Dihexylamine 14.9 895.4 Embodiment 28 (2-28) CI pigment orange 73 Di(2-ethylhexyl)amine 19.4 1007.6 Embodiment 29 (2-29) Diketopyrrolopyrrole (16) Dodecylamine 13.4 955.4 Embodiment 30 (2-30) Diketopyrrolopyrrole (17) 2-Phenylethylamine 7.4 943.4 Embodiment 31 (2-31) Diketopyrrolopyrrole (18) Dibenzylamine 15.0 949.2 Embodiment 32 (3-1) CI pigment orange 71 Di-n-octylamine 21.8 945.4 Embodiment 33 (3-2) CI pigment orange 71 Bis(2-methoxyethyl)amine 12.0 728.8 Embodiment 34 (4-1) Diketopyrrolopyrrole (19) Di(2-ethylhexyl)amine 18.6 1031.4 Embodiment 35 (4-2) Diketopyrrolopyrrole (20) Didecylamine 27.6 1043.6

[Example 36] (Synthesis of pigment dispersant (5-1)) At room temperature, add 30 parts of C.I. Pigment Red 272 ("Irgazin RED K3800" produced by BASF) to 300 parts of 102% fuming sulfuric acid. Stir at room temperature for 3 hours, and then add dropwise to 1500 parts of cold methyl ethyl ketone over 30 minutes. Filter the precipitated disulfonic acid, wash with 3000 parts of ice methyl ethyl ketone, and dry at 80°C to obtain the disulfonic acid. Add 10 parts of the disulfonic acid to 100 parts of N,N-dimethylformamide, and slowly add dropwise 10 parts of sulfinyl chloride. Heat the reaction solution to 60 degrees and stir for 6 hours. The reaction solution was poured into 250 parts of ice and 250 parts of water, and the precipitate was filtered and washed three times with 500 parts of ice water to obtain a filter cake of chlorosulfonyl diketo pyrrolopyrrole. The filter cake was put into 300 parts of water and 8.0 parts of di(2-ethylhexyl)amine (manufactured by Tokyo Chemical Industry Co., Ltd.) and stirred for 3 hours. The mixed solution was filtered and washed with water to obtain a filter cake. Furthermore, the filter cake was put into 300 parts of methanol and stirred for 3 hours, and then the mixed solution was filtered and the filtrate was recovered, and the solvent was distilled off by a rotary evaporator. Thus, a pigment dispersant (5-1) (12.8 parts) was obtained.

Pigment dispersant (5-1)

[Chemistry 27]

[Example 37] (Preparation of red pigment composition (P-3)) A mixture of 270 parts of diketopyrrolopyrrole red pigment C.I. Pigment Red 254 ("Irgazin RED L3630" produced by BASF), 30 parts of pigment dispersant (2-7), 1500 parts of sodium chloride and 150 parts of diethylene glycol was kneaded at 60°C for 6 hours using a 1-gallon stainless steel kneader (Inoue Seisakusho). The mixture was then added to 5 liters of warm water and stirred for 1 hour while being heated to 70°C to prepare a slurry. Filtering and washing were repeated to remove sodium chloride and diethylene glycol, followed by drying and pulverization to obtain 290 parts of red pigment composition P-3.

[Example 38] (Preparation of red pigment composition (P-4)) Red pigment composition P-4 was obtained by the same method as in Example 37 except that pigment dispersant (2-7) was replaced with pigment dispersant (2-12).

[Example 39] (Preparation of red pigment composition (P-5)) Red pigment composition P-5 was obtained by the same method as in Example 37 except that pigment dispersant (2-7) was replaced with pigment dispersant (2-14).

[Example 101] (Preparation of coloring composition (RP-1)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-1). Pigment composition (P-1) 10.8 parts Pigment dispersant formula (2-1) 0.3 parts Pigment dispersant A 0.3 parts Pigment dispersant B 0.6 parts Resin type dispersant solution 2 12.0 parts Acrylic resin solution 2 16.0 parts Propylene glycol monomethyl ether acetate 60.0 parts

[Example 102 to Example 144] (Preparation of coloring compositions (RP-2 to RP-44)) Coloring compositions (RP-2 to RP-44) were prepared in the same manner as the coloring composition (RP-1), except that the pigment composition (P-1) and the pigment dispersant (2-1) were changed to the pigment composition and the pigment dispersant listed in Table 6.

[Table 6] Table 6 Coloring composition Pigment composition Pigment dispersant Embodiment 101 RP-1 P-1 (2-1) Embodiment 102 RP-2 P-1 (2-2) Embodiment 103 RP-3 P-1 (2-3) Embodiment 104 RP-4 P-1 (2-4) Embodiment 105 RP-5 P-1 (2-5) Embodiment 106 RP-6 P-1 (2-6) Embodiment 107 RP-7 P-1 (2-7) Embodiment 108 RP-8 P-1 (2-8) Embodiment 109 RP-9 P-1 (2-9) Embodiment 110 RP-10 P-1 (2-10) Embodiment 111 RP-11 P-1 (2-11) Embodiment 112 RP-12 P-1 (2-12) Embodiment 113 RP-13 P-1 (2-13) Embodiment 114 RP-14 P-1 (2-14) Embodiment 115 RP-15 P-1 (2-15) Embodiment 116 RP-16 P-1 (2-16) Embodiment 117 RP-17 P-1 (2-17) Embodiment 118 RP-18 P-1 (2-18) Embodiment 119 RP-19 P-1 (2-19) Embodiment 120 RP-20 P-1 (2-20) Embodiment 121 RP-21 P-1 (2-21) Embodiment 122 RP-22 P-1 (2-22) Embodiment 123 RP-23 P-1 (2-23) Embodiment 124 RP-24 P-1 (2-24) Embodiment 125 RP-25 P-1 (2-25) Embodiment 126 RP-26 P-1 (2-26) Embodiment 127 RP-27 P-1 (2-27) Embodiment 128 RP-28 P-1 (2-28) Embodiment 129 RP-29 P-1 (2-29) Embodiment 130 RP-30 P-1 (2-30) Embodiment 131 RP-31 P-1 (2-31) Embodiment 132 RP-32 P-1 (3-1) Embodiment 133 RP-33 P-1 (3-2) Embodiment 134 RP-34 P-1 (4-1) Embodiment 135 RP-35 P-1 (4-2) Embodiment 136 RP-36 P-1 (5-1) Embodiment 137 RP-37 P-2 (2-2) Embodiment 138 RP-38 P-2 (2-4) Embodiment 139 RP-39 P-2 (2-8) Embodiment 140 RP-40 P-2 (2-10) Embodiment 141 RP-41 P-2 (2-11) Embodiment 142 RP-42 P-3 - Embodiment 143 RP-43 P-4 - Embodiment 144 RP-44 P-5 -

[Example 145] (Preparation of coloring composition (RP-45)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-45). Pigment composition (P-1)               11.0 parts Pigment dispersant formula (2-14)                 0.1 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Example 146] (Preparation of coloring composition (RP-46)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-46). Pigment composition (P-1)               10.6 parts Pigment dispersant formula (2-14)                 0.5 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Example 147] (Preparation of coloring composition (RP-47)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-47). Pigment composition (P-1)               10.1 parts Pigment dispersant formula (2-14)                 1.0 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Example 148] (Preparation of coloring composition (RP-48)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-48). Pigment composition (P-1) 8.1 parts Pigment dispersant formula (2-14) 3.0 parts Pigment dispersant A 0.3 parts Pigment dispersant B 0.6 parts Resin type dispersant solution 2 12.0 parts Acrylic resin solution 2 16.0 parts Propylene glycol monomethyl ether acetate 60.0 parts

[Example 149] (Preparation of coloring composition (RP-49)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-49). Pigment composition (P-1)               10.8 parts Pigment dispersant formula (2-14)                 0.3 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 1               6.0 parts Resin type dispersant solution 2               6.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 55.0 parts Propylene glycol monomethyl ether                       5.0 parts

[Example 150] (Preparation of coloring composition (RP-50)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-50). Pigment composition (P-1)               10.8 parts Pigment dispersant formula (2-14)                 0.2 parts Pigment dispersant formula (5-1)                0.1 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2                 12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Example 151] (Preparation of coloring composition (RP-51)) The following mixture was stirred and mixed in a uniform manner, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-51). Pigment composition (P-1)               10.8 parts Pigment dispersant formula (2-14)                 0.1 parts Pigment dispersant formula (5-1)                0.2 parts Pigment dispersant A                   0.3 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2                 12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Comparative Example 1] (Preparation of coloring composition (RP-52)) The following mixture was stirred and mixed to be uniform, and then dispersed for 5 hours using zirconia beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-52). Pigment composition (P-1)               10.8 parts Pigment dispersant A                   0.6 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate              60.0 parts

[Comparative Example 2] (Preparation of coloring composition (RP-53)) The following mixture was stirred and mixed to be uniform, and then dispersed for 5 hours using zirconia beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-53). Pigment composition (P-1)               10.6 parts Pigment dispersant A                   0.8 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate              60.0 parts

[Comparative Example 3] (Preparation of coloring composition (RP-54)) The following mixture was stirred and mixed until uniform, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan) and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-54). Pigment composition (P-1)                   10.8 parts Pigment dispersant B                        0.6 parts Pigment dispersant C                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 60.0 parts

[Comparative Example 4] (Preparation of coloring composition (RP-55)) The following mixture was stirred and mixed to be uniform, and then dispersed for 5 hours using zirconia beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a 5.0 μm filter to prepare a coloring composition (RP-55). Pigment composition (P-2)               10.8 parts Pigment dispersant A                   0.6 parts Pigment dispersant B                    0.6 parts Resin type dispersant solution 2               12.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate              60.0 parts

<Evaluation of coloring composition> (Preparation of contrast measurement substrate) The coloring composition (RP-1 to RP-55) was applied to a 100 mm × 100 mm, 1.1 mm thick glass substrate at a film thickness of x = 0.660 under light source C and dried. Then, it was heated at 230°C for 60 minutes to obtain a red coating.

(Evaluation of contrast ratio of coating) The method for measuring contrast ratio of coating is described. Light emitted from the backlight unit for liquid crystal display is polarized by passing through the polarizing plate, and reaches the polarizing plate through the dry coating of the coloring composition applied on the glass substrate. If the polarizing planes of the polarizing plate and the polarizing plate are parallel, the light passes through the polarizing plate, but when the polarizing planes are orthogonal, the light is blocked by the polarizing plate. However, when the light polarized by the polarizing plate passes through the dry coating of the coloring composition, scattering is caused by pigment particles, and if a part of the polarization plane is offset, the amount of light passing through the polarizing plate is reduced when the polarizing plates are parallel, and a part of the light passes through the polarizing plate when the polarizing plates are orthogonal. The brightness of the transmitted light on the polarizing plate is measured, and the ratio of the brightness when the polarizing plates are parallel to the brightness when the polarizing plates are orthogonal (contrast ratio) is calculated. (Contrast ratio) = (Brightness when parallel) / (Brightness when orthogonal) The contrast ratio is evaluated in the following 4 stages. ◎: 5500 or more (extremely good) ○: 4500 or more, less than 5500 (good) △: 3500 or more, less than 4500 (poor) ×: less than 3500 (extremely poor)

Therefore, if scattering occurs due to the pigment in the coating, the brightness when parallel is reduced and the brightness when orthogonal is increased, so the contrast ratio is reduced.

In addition, a colorimeter ("BM-5A" manufactured by Topcon) was used as a luminance meter, and a polarizing plate ("NPF-G1220DUN" manufactured by Nitto Denko) was used as a polarizing plate. In addition, a black mask with a 1 cm square hole was placed in the measurement part to block excess light during the measurement.

<Evaluation of viscosity stability> (Measurement of initial viscosity and viscosity increase rate over time) Regarding the viscosity of the coloring composition, the initial viscosity at 25°C was measured using an E-type viscometer ("ELD type viscometer" manufactured by Toki Sangyo Co., Ltd.) on the day the coloring composition was prepared. Then, for the coloring composition that had been left at 40°C for 7 days from the day the coloring composition was prepared, the sample temperature was returned to 25°C, and the viscosity over time was measured according to the viscosity measurement method described above, and the viscosity increase rate over time was calculated according to the following formula. Vast increase rate over time = (viscosity over time) / (initial viscosity) × 100 (%)

(Evaluation of initial viscosity and viscosity increase rate over time) Viscosity stability is evaluated by viscosity increase rate over time. If the viscosity increase rate over time is 80% or more and less than 120%, it is durable in practical use. If the viscosity is reduced or increased beyond the above range, the coloring composition cannot be applied to the glass substrate under the same application conditions, which will cause problems in productivity. A range of 90% or more and less than 110% is more preferred. ○: Viscosity increase rate over time is 90% or more and less than 110% △: Viscosity increase rate over time is 80% or more and less than 90%, or 110% or more and less than 120% ×: Viscosity increase rate over time is less than 80%, or 120% or more

[Table 7] Table 7 Coloring composition Evaluation results Contrast ratio Viscosity stability Embodiment 101 RP-1 △ △ Embodiment 102 RP-2 ◎ ○ Embodiment 103 RP-3 ◎ ○ Embodiment 104 RP-4 ○ ○ Embodiment 105 RP-5 ○ ○ Embodiment 106 RP-6 ◎ ○ Embodiment 107 RP-7 ◎ ○ Embodiment 108 RP-8 ○ △ Embodiment 109 RP-9 ○ ○ Embodiment 110 RP-10 ◎ ○ Embodiment 111 RP-11 ◎ ○ Embodiment 112 RP-12 ◎ ○ Embodiment 113 RP-13 ◎ ○ Embodiment 114 RP-14 ◎ ○ Embodiment 115 RP-15 ○ ○ Embodiment 116 RP-16 ◎ ○ Embodiment 117 RP-17 ○ ○ Embodiment 118 RP-18 ◎ ○ Embodiment 119 RP-19 ◎ ○ Embodiment 120 RP-20 ◎ ○ Embodiment 121 RP-21 ○ ○ Embodiment 122 RP-22 ○ ○ Embodiment 123 RP-23 ◎ ○ Embodiment 124 RP-24 ◎ ○ Embodiment 125 RP-25 ○ ○ Embodiment 126 RP-26 ◎ ○ Embodiment 127 RP-27 ◎ ○ Embodiment 128 RP-28 ◎ ○ Embodiment 129 RP-29 ◎ ○ Embodiment 130 RP-30 ○ ○ Embodiment 131 RP-31 ○ ○ Embodiment 132 RP-32 ◎ ○ Embodiment 133 RP-33 ○ ○ Embodiment 134 RP-34 ◎ ○ Embodiment 135 RP-35 ◎ ○ Embodiment 136 RP-36 ◎ ○ Embodiment 137 RP-37 ○ ○ Embodiment 138 RP-38 ◎ ○ Embodiment 139 RP-39 ◎ ○ Embodiment 140 RP-40 ◎ ○ Embodiment 141 RP-41 ◎ ○ Embodiment 142 RP-42 ◎ ○ Embodiment 143 RP-43 ◎ ○ Embodiment 144 RP-44 ◎ ○ Embodiment 145 RP-45 ◎ ○ Embodiment 146 RP-46 ◎ ○ Embodiment 147 RP-47 ◎ ○ Embodiment 148 RP-48 ◎ △ Embodiment 149 RP-49 ○ ○ Embodiment 150 RP-50 ◎ ○ Embodiment 151 RP-51 ◎ ○ Comparison Example 1 RP-52 △ △ Comparison Example 2 RP-53 △ × Comparison Example 3 RP-54 × × Comparison Example 4 RP-55 × ×

The coloring composition using the diketopyrrolopyrrole pigment dispersant of the present invention has good contrast and viscosity stability.

<Method for preparing other coloring compositions> (Preparation of coloring composition (RP-56)) The following mixture was stirred and mixed until uniform, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan) and then filtered using a filter with a pore size of 5.0 μm to prepare a coloring composition (RP-56). Anthraquinone pigment ("Cinilex RED SR3C" manufactured by CINIC)                     12.0 parts Resin type dispersant solution 1               6.0 parts Resin type dispersant solution 2               6.0 parts Acrylic resin solution 2             16.0 parts Propylene glycol monomethyl ether acetate                 55.0 parts Propylene glycol monomethyl ether                       5.0 parts

<Method for producing photosensitive coloring composition> [Example 201] (Production of photosensitive coloring composition (RR-1)) The mixture of the following composition was uniformly stirred and mixed, and then filtered using a filter with a pore size of 1.0 μm to obtain a red photosensitive coloring composition (RR-1). Coloring composition (RP-1) 16.28 parts Coloring composition (RP-56) 33.72 parts Acrylic resin solution 1 3.60 parts Epoxy compound (EHPE-3150 manufactured by Daicel) 0.16 parts Photopolymerizable monomer (Aronix M402 manufactured by Toagosei) 1.10 parts Photopolymerizable monomer (Aronix M350 manufactured by Toagosei) 1.45 parts Photopolymerization initiator (IRGACURE OXE02 manufactured by BASF) 0.15 parts Photopolymerization initiator ("IRGACURE 369" manufactured by BASF)                     0.30 parts Sensitizer ("KAYACURE DETX-S" manufactured by Nippon Kayaku)                               0.05 parts Mercapto compound (pentaerythritol tetrathiopropionate)  0.20 parts Leveling agent ("BYK-330" manufactured by BYK-Chemie)                             0.05 parts Antioxidant ("IRGANOX 1010" manufactured by BASF)                        0.10 parts Propylene glycol monomethyl ether acetate            32.84 parts 3-ethoxypropionic acid ethyl ester             10.00 parts

[Example 202 to Example 251, Comparative Example 5 to Comparative Example 8] (Preparation of photosensitive coloring compositions (RR-2 to RR-55)) Photosensitive coloring compositions (RR-2 to RR-55) were prepared in the same manner as in Example 201, except that the coloring composition (RP-1) was replaced with the coloring composition (RP-2 to RP-55) and the ratio of the coloring composition (RP-2 to RP-55) to the coloring composition (RP-56) was adjusted so as to obtain the same chromaticity as in Example 201.

<Evaluation of photosensitive coloring composition> The obtained photosensitive coloring composition was evaluated by the following method. The results are shown in Table 8. (Evaluation of brightness) The photosensitive coloring composition (RR-1 to RR-55) was applied on a 100 mm × 100 mm, 1.1 mm thick glass substrate using a rotary coater, and the solvent was removed by heating at 70°C for 15 minutes in a clean oven to obtain a coating film. Then, ultraviolet light exposure was performed using an ultrahigh pressure mercury lamp with a cumulative light amount of 100 mJ/ ^cm2 , and development was performed using an alkaline developer at 23°C to obtain a coated substrate. Then, the substrate was heated at 230°C for 30 minutes in a clean oven, left to cool, and the lightness Y (C) of the obtained coated substrate was measured using a microspectrophotometer ("OSP-SP100" manufactured by Olympus Optics). Furthermore, the chromaticity of the red coated substrate after heat treatment at 230°C was (x=0.660, y=0.324) under the C light source. As an alkaline developer, a developer containing 1.5% by mass of sodium carbonate, 0.5% by mass of sodium bicarbonate, 8.0% by mass of anionic surfactant ("Pelex NBL" manufactured by Kao Corporation) and 90% by mass of water was used. The evaluation of lightness was performed in the following three stages. ◎: 18.5 or more (extremely good) ○: 18.3 or more, less than 18.5 (good) △: 18.1 or more, less than 18.3 (poor) ×: less than 18.1 (extremely poor)

(Evaluation of contrast ratio) The contrast ratio is measured using the substrate used in the brightness evaluation. The contrast ratio is evaluated in the following 4 stages. ◎: 6500 or more (extremely good) ○: 5500 or more, less than 6500 (good) △: 4500 or more, less than 5500 (poor) ×: less than 4500 (extremely poor)

(Evaluation of crystallization on the coating surface) The photosensitive coloring composition (RR-1 to RR-55) was applied to a 100 mm × 100 mm, 1.1 mm thick glass substrate using a rotary coater, and the solvent was removed in a clean oven at 70°C for 15 minutes to obtain a coating. Then, ultraviolet exposure was performed using an ultra-high pressure mercury lamp with a cumulative light amount of 100 mJ/ ^cm2 , and development was performed using an alkaline developer at 23°C to obtain a coated substrate. Then, a heat treatment was performed at 230°C for 60 minutes, and then a heat treatment was further performed at 240°C for 60 minutes, and a heat treatment was performed at 280°C for 60 minutes. The coated surface of the substrate after heat treatment was observed using an optical microscope, and the presence or absence of crystal precipitation was determined according to the following criteria. ◎…No crystal precipitation was observed after heat treatment at 230°C for 60 minutes, after further heat treatment at 240°C for 60 minutes, and after further heat treatment at 280°C for 60 minutes. ○…No crystal precipitation was observed after heat treatment at 230°C for 60 minutes and after further heat treatment at 240°C for 60 minutes, but crystal precipitation was observed after further heat treatment at 280°C for 60 minutes. △…No crystal precipitation was observed after heat treatment at 230°C for 60 minutes, but crystal precipitation was observed after further heat treatment at 240°C for 60 minutes. ×…Crystal precipitation was observed after heat treatment at 230°C for 60 minutes.

(Evaluation of solvent resistance) A photosensitive coloring composition (RR-1 to RR-55) was applied to a 100 mm × 100 mm, 1.1 mm thick glass substrate using a rotary coater, and the solvent was removed in a clean oven at 70°C for 15 minutes to obtain a dry coating. At this time, the coating was performed in such a way that the dry coating became 2.5 μm. Next, a photoresist with a 100 μm wide (200 μm pitch) stripe pattern was exposed to ultraviolet light at a cumulative light dose of 100 mJ/cm ² using an ultra-high pressure mercury lamp, and developed using an alkaline developer at 23°C to obtain a stripe-shaped coated substrate. Next, the coating was heated in a clean oven at 230°C for 30 minutes. Here, the chromaticity (L*(1), a*(1), b*(1)) was measured under illuminant C. The coating was then immersed in N-methyl pyrrolidone (NMP) at 40°C for 30 minutes, and the chromaticity (L*(2), a*(2), b*(2)) was further measured under illuminant C. The chromaticity values before and after NMP immersion were used to calculate the color difference ΔE*ab according to the following calculation formula, and the solvent resistance of the coating was evaluated in the following four stages. Calculation formula: ΔE*ab=[[L*(2)-L*(1)]2+[a*(2)-a*(1)]2+[b*(2)-b*(1)]2]1/2 ◎: ΔE*ab is less than 0.7 (extremely good) ○: ΔE*ab is 0.7 or more and less than 1.0 (good) △: ΔE*ab is 1.0 or more and less than 3.0 (fair) ×: ΔE*ab is 3.0 or more (poor)

(Evaluation of dye migration) The photosensitive coloring composition (RR-1 to RR-55) was applied to a glass substrate using a slot die coater, and then pre-baked for 2 minutes using a 90°C hot plate to form a coating with a thickness of 2.4 μm. The substrate with the coating was then cooled to room temperature, and then exposed to radiation of wavelengths of 365 nm, 405 nm, and 436 nm at an exposure dose of 1,000 J/m ² using a high-pressure mercury lamp through a stripe resist. Alkaline development was performed, followed by washing with ultrapure water, and post-baking was performed at 230°C for 20 minutes to form red stripe pixels on the substrate. Next, the transmittance (T1) at 520 nm on a glass substrate 8 μm away from the red stripe pixel was measured. Furthermore, the acrylic resin solution 2 was applied to the substrate using a slot die coater, and then pre-baked for 2 minutes using a 90°C heating plate to form a coating with a film thickness of 2.5 μm. Furthermore, post-baking was performed at 230°C for 20 minutes. Next, the transmittance (T2) at 520 nm on a glass substrate 8 μm away from the red stripe pixel was measured. The numerical difference between T1 and T2 was taken as ΔT (%) and evaluated in the following three stages. The smaller the ΔT value, the less the reduction in brightness caused by color migration to the adjacent filter segments of other colors, and it can be said that the color migration is suppressed. ○: ΔT less than 0.9% (good) △: ΔT 0.9% or more and less than 3.0% (fair) ×: ΔT 3.0% or more (poor)

[Table 8] Table 8 Photosensitive coloring composition Coloring composition Evaluation results Brightness Contrast ratio Crystallization Solvent resistance Transferability Embodiment 201 RR-1 RP-1 ○ △ △ △ ○ Embodiment 202 RR-2 RP-2 ○ ◎ ○ ○ ○ Embodiment 203 RR-3 RP-3 ◎ ◎ ◎ ○ ○ Embodiment 204 RR-4 RP-4 ○ ○ ○ ○ ○ Embodiment 205 RR-5 RP-5 ○ ○ ◎ ○ ○ Embodiment 206 RR-6 RP-6 ○ ◎ ◎ ○ ○ Embodiment 207 RR-7 RP-7 ◎ ◎ ◎ ○ ○ Embodiment 208 RR-8 RP-8 ○ ○ △ △ ○ Embodiment 209 RR-9 RP-9 ○ ○ ○ ○ ○ Embodiment 210 RR-10 RP-10 ◎ ◎ ◎ ◎ ○ Embodiment 211 RR-11 RP-11 ◎ ◎ ◎ ◎ ○ Embodiment 212 RR-12 RP-12 ◎ ◎ ◎ ◎ ○ Embodiment 213 RR-13 RP-13 ◎ ◎ ◎ ◎ ○ Embodiment 214 RR-14 RP-14 ◎ ◎ ◎ ◎ ○ Embodiment 215 RR-15 RP-15 ○ ○ ◎ ○ ○ Embodiment 216 RR-16 RP-16 ○ ◎ ◎ ○ ○ Embodiment 217 RR-17 RP-17 ○ ○ ○ ○ ○ Embodiment 218 RR-18 RP-18 ○ ◎ ◎ ○ ○ Embodiment 219 RR-19 RP-19 ○ ◎ ○ ○ △ Embodiment 220 RR-20 RP-20 ◎ ◎ ◎ ○ △ Embodiment 221 RR-21 RP-21 ○ ○ ◎ ○ ○ Embodiment 222 RR-22 RP-22 ○ ○ ○ ○ ○ Embodiment 223 RR-23 RP-23 ○ ◎ ○ ○ ○ Embodiment 224 RR-24 RP-24 ○ ◎ ◎ ○ ○ Embodiment 225 RR-25 RP-25 ◎ ○ ◎ ○ ○ Embodiment 226 RR-26 RP-26 ○ ◎ ○ ○ ○ Embodiment 227 RR-27 RP-27 ◎ ◎ ◎ ◎ ○ Embodiment 228 RR-28 RP-28 ◎ ◎ ◎ ◎ ○ Embodiment 229 RR-29 RP-29 ○ ◎ ◎ ○ ○ Embodiment 230 RR-30 RP-30 ○ ○ ◎ ○ ○ Embodiment 231 RR-31 RP-31 ○ ○ ○ ○ ○ Embodiment 232 RR-32 RP-32 ◎ ◎ ◎ ○ ○ Embodiment 233 RR-33 RP-33 ◎ ○ ◎ ○ ○ Embodiment 234 RR-34 RP-34 ◎ ◎ ◎ ○ ○ Embodiment 235 RR-35 RP-35 ○ ◎ ◎ ○ ○ Embodiment 236 RR-36 RP-36 ◎ ◎ ◎ ◎ ○ Embodiment 237 RR-37 RP-37 ○ ○ ○ ○ ○ Embodiment 238 RR-38 RP-38 ○ ◎ ◎ ○ ○ Embodiment 239 RR-39 RP-39 ◎ ◎ ◎ ◎ ○ Embodiment 240 RR-40 RP-40 ◎ ◎ ◎ ◎ ○ Embodiment 241 RR-41 RP-41 ◎ ◎ ◎ ◎ ○ Embodiment 242 RR-42 RP-42 ◎ ◎ ◎ ○ ○ Embodiment 243 RR-43 RP-43 ◎ ◎ ◎ ◎ ○ Embodiment 244 RR-44 RP-44 ◎ ◎ ◎ ◎ ○ Embodiment 245 RR-45 RP-45 ◎ ◎ ○ ◎ ○ Embodiment 246 RR-46 RP-46 ◎ ◎ ◎ ◎ ○ Embodiment 247 RR-47 RP-47 ◎ ◎ ◎ ◎ ○ Embodiment 248 RR-48 RP-48 ○ ◎ ◎ ○ ○ Embodiment 249 RR-49 RP-49 ○ ○ ◎ ○ ○ Embodiment 250 RR-50 RP-50 ◎ ◎ ◎ ◎ ○ Embodiment 251 RR-51 RP-51 ◎ ◎ ◎ ◎ ○ Comparison Example 5 RR-52 RP-52 △ △ × △ △ Comparison Example 6 RR-53 RP-53 × △ × × × Comparative Example 7 RR-54 RP-54 × × × × × Comparative Example 8 RR-55 RP-55 △ × × × △

According to the results in Table 8, the use of the diketopyrrolopyrrole pigment dispersant of the present invention can achieve high brightness and high contrast, inhibit crystallization after heat treatment, and achieve good solvent resistance and migration properties.

Comparison of RR-1 to RR-14 shows that the more carbon atoms in the alkyl group of the raw material amine, the higher the effect of suppressing crystallization, and the results show high brightness and high contrast, and excellent solvent resistance. Similarly, the results of the secondary amine are better than those of the primary amine, and the results of the branched alkyl group are better than those of the linear alkyl group.

According to the comparison of RR-45 to RR-48, from the viewpoint of the balance between brightness and contrast and inhibition of crystallization, the amount of the pigment dispersant of the present invention added is preferably 0.1% by mass to 30% by mass, more preferably 1% by mass to 20% by mass, relative to the pigment.

<Preparation of color filter> A green photosensitive coloring composition and a blue photosensitive coloring composition for preparing a color filter were prepared. In addition, for red, the photosensitive coloring composition (RR-14) of the present invention was used.

(Preparation of green coloring composition (GP-1)) The mixture of the following composition was stirred and mixed to be uniform, and then dispersed for 5 hours using zirconia beads with a diameter of 0.5 mm and an Eiger-mill ("mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a filter with a pore size of 5.0 μm to prepare a green coloring composition (GP-1). Green pigment (C.I. Pigment Green 58)         8.6 parts Yellow pigment (C.I. Pigment Yellow 138)        3.4 parts Resin type dispersant ("EFKA 4300" manufactured by BASF)                    3.0 parts Acrylic resin solution 1             25.0 parts Propylene glycol monomethyl ether acetate              52.0 parts

(Preparation of green photosensitive coloring composition (GR-1)) The mixture of the following composition was stirred and mixed until it became uniform, and then filtered through a filter with a pore size of 1.0 μm to prepare a green photosensitive coloring composition (GR-1). Green coloring composition (GP-1) 42.0 parts Acrylic resin solution 1 13.2 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toagosei Co., Ltd.) 2.8 parts Photopolymerization initiator ("IRGACURE 907" manufactured by BASF) 2.0 parts Sensitizer ("EAB-F" manufactured by Hodoko Chemical Co., Ltd.) 0.4 parts Propylene glycol monomethyl ether acetate 39.6 parts

(Preparation of blue coloring composition (BP-1)) The mixture of the following composition was stirred and mixed to be uniform, and then dispersed for 5 hours using zirconium oxide beads with a diameter of 0.5 mm and an Eiger mill ("Mini model M-250 MKII" manufactured by Eiger Japan Co., Ltd.), and then filtered using a filter with a pore size of 5.0 μm to prepare a blue coloring composition (BP-1). Blue pigment (C.I. Pigment Blue 15:6)         7.2 parts Purple pigment (C.I. Pigment Purple 23)         4.8 parts Resin type dispersant ("EFKA 4300" manufactured by Ciba Japan)                         1.0 parts Acrylic resin solution 1             35.0 parts Propylene glycol monomethyl ether acetate              52.0 parts

(Preparation of blue photosensitive coloring composition (BR-1)) The mixture of the following composition was stirred and mixed until it became uniform, and then filtered through a filter with a pore size of 1.0 μm to prepare a blue photosensitive coloring composition (BR-1). Blue coloring composition (BP-1) 34.0 parts Acrylic resin solution 2 15.2 parts Photopolymerizable monomer ("Aronix M402" manufactured by Toagosei Co., Ltd.) 3.3 parts Photopolymerization initiator ("IRGACURE 907" manufactured by BASF) 2.0 parts Sensitizer ("EAB-F" manufactured by Hodoko Chemical Co., Ltd.) 0.4 parts Propylene glycol monomethyl ether acetate 45.1 parts

A black matrix is patterned on a glass substrate, and the red photosensitive coloring composition (RR-14) of the present invention is applied to the substrate using a rotary coater to form a colored film. The film is irradiated with 200 mJ/ ^cm2 of ultraviolet light using an ultrahigh pressure mercury lamp through a photoresist. Subsequently, an alkaline developer containing a 0.2 mass% sodium carbonate aqueous solution is sprayed to remove the unexposed portion, and then the substrate is washed with ion exchange water, and the substrate is heated at 230°C for 30 minutes to form a red filter segment. Here, the red filter segment is set to meet the chromaticity of x=0.660 under C light source after heat treatment at 230°C. In addition, using the same method, a green filter segment is formed using a green photosensitive coloring composition (GR-1) in a manner that conforms to a chromaticity of y=0.570, and a blue filter segment is formed using a blue photosensitive coloring composition (BR-1) in a manner that conforms to a chromaticity of y=0.045, and each filter segment is formed to obtain a color filter.

By using the photosensitive coloring composition (RR-14) of the present invention in forming the red filter segment, the color filter can achieve high brightness and high contrast, and can be suitably used without problems in other physical properties.

without.

without.

without.

Claims (6)

A diketopyrrolopyrrole pigment dispersant represented by the following general formula (2), general formula (3) or general formula (5);

In the general formula (2), the general formula (3) and the general formula (5), _R21 to _R24 , _R27 and _R28 are independently fluorine atoms, chlorine atoms, bromine atoms, cyano groups or alkyl groups having 1 to 20 carbon atoms; _X1 to _X4 , _X7 and _X8 are independently hydrogen atoms, alkyl groups having 1 to 20 carbon atoms which may have a substituent, phenyl groups which may have a substituent or aralkyl groups which may have a substituent, wherein the phenyl groups which may have a substituent are phenyl groups having alkyl groups having 1 to 20 carbon atoms, trifluoromethyl groups, halogen atoms, nitro groups, cyano groups, carbamoyl groups, sulfamoyl groups or alkoxy groups having 1 to 4 carbon atoms as substituents; wherein one of _X1 and _X2 , one of _X3 and _X4 , _X7 and X8 are independently substituted. One of ₈ is an unsubstituted linear or branched alkyl group having 3 to 20 carbon atoms, an unsubstituted oxyalkyl group having 3 to 20 carbon atoms and having an ether bond, an optionally substituted phenyl group, or an optionally substituted aralkyl group; -SO ₃ M represents a sulfo group or a metal salt or alkylammonium salt of a sulfo group. A pigment composition characterized by containing a pigment and a diketopyrrolopyrrole pigment dispersant as described in claim 1. The pigment composition as described in claim 2, wherein the pigment contains a diketopyrrolopyrrole red pigment. A coloring composition characterized by comprising a pigment composition as described in claim 2 or claim 3, a binder resin and an organic solvent. The coloring composition as described in claim 4 further contains at least one of a photopolymerizable monomer and a photopolymerization initiator. A color filter, comprising a filter segment formed by the coloring composition as described in claim 4 or claim 5.