JP2014202774A - Color filter coloring composition and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide: a color filter coloring composition which offers superior dispersibility and high brightness; and a highly bright color filter produced using the same.SOLUTION: A color filter coloring composition comprises a pigment (A), an absorbent (B) having a pigment absorbing group, and a dispersant (C), where content of the absorbent (B) is 8 pts.wt. or less per 100 pts.wt. of the pigment (A), and the dispersant (C) comprises a linear dispersant (C1) which has a site (x) for forming salt with the pigment absorbing group at one terminal end and a number average molecular weight of 5000 or more and/or a comb-shaped dispersant (C2) which has a site (x) for forming salt with the pigment absorbing group on the main chain and a side chain having a number average molecular weight of 5000 or more.

Description

  An object of this invention is to provide the coloring composition for color filters which is excellent in a dispersibility, fluidity | liquidity, and storage stability, and has high brightness | luminance, and a color filter using the same.

In recent years, as a coloring composition for a color filter, a pigment using an adsorbent adsorbed on the pigment surface and a dispersant having a steric hindrance site having a salt-forming site with the adsorbent at one end and having an affinity for a solvent. A composition has been reported, and Patent Documents 1 to 4 describe a dispersant for obtaining a pigment dispersion that is excellent in dispersibility, fluidity, and storage stability at a low use amount.
In this case, the adsorbent adsorbed on the pigment surface has a basic group such as an amino group, and the salt forming site has an acidic group, and the adsorbent adsorbed on the pigment surface has an acidic group such as a sulfonic acid group. The group which has a group and forms a salt with the group may have a basic group such as an amino group.

The pigment used in the color filter is very fine, and in particular, recently, high contrast is required. For this purpose, it is necessary to use a finer pigment.
On the other hand, the adsorbent is very important in obtaining a pigment dispersion, and if it is not used to some extent, the dispersibility is lowered, and a pigment dispersion excellent in fluidity and storage stability cannot be obtained at present. is there. In particular, the finer the pigment, the more adsorbent must be used.

  However, when a large amount of adsorbent is used, the brightness of a color filter using a pigment dispersion using the adsorbent tends to decrease. The reason is not clear, but any adsorbent having an acidic group or one having a basic group has such a property. Therefore, how to reduce the adsorbent becomes a problem.

  However, if the adsorbent is merely reduced, the dispersibility is lowered, and a pigment dispersion excellent in fluidity and storage stability cannot be obtained, and it is difficult to achieve both the lightness of the coating film and the dispersibility.

JP 2008-029901 A International Publication No. 2007/052687 International Publication No. 2008/007776 JP 2009-251481 A

  An object of the present invention is to provide a color filter coloring composition that achieves excellent dispersibility and high brightness, and a high brightness color filter formed by using the color filter coloring composition. .

That is, the present invention is a coloring composition for a color filter having a pigment (A), an adsorbent (B) having a pigment adsorbing group, and a dispersant (C),
The adsorbent (B) is 8 parts by weight or less with respect to 100 parts by weight of the pigment (A),
Dispersant (C) is a linear dispersant (C1) having a site (x) that forms a salt with a pigment adsorbing group at one end and having a number average molecular weight of 5000 or more.
And / or
A coloring composition for a color filter, which is a comb-shaped dispersant (C2) having a moiety (x) that forms a salt with a pigment adsorbing group in the main chain and having a side chain number average molecular weight of 5000 or more. Related to things.

  The present invention also relates to the color composition for a color filter, wherein the pigment adsorbing group has a basic group, and the site (x) that forms a salt with the pigment adsorbing group has an acidic group.

  In the present invention, the adsorbent (B) having a pigment adsorbing group comprises a pigment derivative having a basic group, an anthraquinone derivative having a basic substituent, a triazine derivative having a basic substituent, and a basic substituent. The color filter comprising: a dye derivative (Q) having at least one basic substituent selected from the group consisting of an acridone derivative having a vinyl resin (S) having a basic group and / or The present invention relates to a coloring composition.

  The present invention also relates to the colored composition for a color filter, wherein the vinyl resin (S) having a basic group has a tertiary amino group and has an amine value of 50 to 500 mgKOH / g. .

  In the present invention, the dispersant (C) includes a polymer (X) having a hydroxyl group at one end, an aromatic tricarboxylic acid anhydride (Y1) and / or an aromatic tetracarboxylic acid dianhydride (Y2). It is a dispersing agent which has an aromatic carboxyl group made by making this react, It is related with the said coloring composition for color filters characterized by the above-mentioned.

  In the present invention, the pigment (A) is C.I. I. Pigment green 58 and / or C.I. I. Pigment Yellow 150, and the color filter coloring composition.

  Furthermore, the present invention relates to the color composition for color filters, further comprising a photopolymerizable monomer and / or a photopolymerization initiator.

  Furthermore, the present invention relates to a color filter comprising a filter segment formed from the colored composition for a color filter on a substrate.

  A color excellent in dispersibility and lightness by using a coloring composition for a color filter containing a pigment, a specific amount of an adsorbent, and a dispersant having a high molecular weight chain that forms a salt with the adsorbent according to the present invention. It becomes a coloring composition for filters, and it becomes possible to form a color filter with high brightness.

Hereinafter, the present invention will be described in detail.
The red coloring composition for a color filter of the present invention contains a pigment (A), an adsorbent (B) having pigment adsorbing ability, and a dispersant (C) having a high molecular weight chain that forms a salt with the adsorbent. It is a coloring composition for color filters.

  The adsorbent (B) is very important in obtaining a pigment dispersion, and if not used to some extent, the dispersibility decreases, and a pigment dispersion excellent in fluidity and storage stability cannot be obtained. The finer the pigment, the more adsorbent must be used.

  However, when a large amount of adsorbent is used, the brightness of a color filter using a pigment dispersion using the adsorbent tends to decrease. The reason is not clear, but any adsorbent having an acidic group or one having a basic group has such a property. Therefore, how to reduce the adsorbent becomes a problem. The finer the pigment, the less the adsorbent (B), the lower the dispersibility, and a pigment dispersion excellent in fluidity and storage stability cannot be obtained, but the molecular weight of the dispersant (C) is increased. This can solve this problem.

  Specifically, by suppressing the amount of the adsorbent (B) added to the pigment (A) to 8 parts by weight or less, it is possible to suppress a decrease in lightness derived from the adsorbent (B). In the case of the chain dispersant (C1), the number average molecular weight is 5000 or more, and in the case of the comb-type dispersant (C2), the molecular weight of the side chain is 5000 or more so that fluidity and storage stability are excellent. Pigment dispersion can be obtained.

<Pigment (A)>
As a pigment contained in the coloring composition for a color filter of the present invention, organic or inorganic pigments can be used alone or in admixture of two or more. Among the pigments, pigments having high color developability and high heat resistance, particularly pigments having high heat decomposition resistance are preferred, and organic pigments are usually used. Hereinafter, typical pigments that can be used in the coloring composition for a color filter of the present invention are listed.

  Examples of red pigments that can be used in the present invention include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 14, 17, 22, 23, 31, 38, 41, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 57: 1, 81, 81: 1, 81: 2, 81: 3, 81: 4, 83, 88, 90, 105, 112, 119, 122, 123, 144, 146, 149, 150, 155, 166, 168, 169, 170, 171, 172, 175, 176, 177, 178, 179, 184, 185, 187, 188, 190, 200, 202, 206, 207, 208,209,210,216,220,221,224,226,242,246,254,255,264,269,270,272,273,274,276,277,278,279,280,2 1,282,283,284,285,286,287 or diketopyrrolopyrrole pigment described in JP-T 2011-523433 discloses the like, but not particularly limited thereto.

  Examples of the orange pigment that can be used in the present invention include C.I. I. Pigment Orange 38, 43, 71, 73, etc. are mentioned, but it is not particularly limited to these.

  Examples of yellow pigments that can be used in the present invention include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 11, 12, 13, 14, 15, 16, 17, 18, 20, 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, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 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 the quinophthalone pigment described in Japanese Patent No. 4999326 However, it is not particularly limited to these.

  Examples of the green pigment that can be used in the present invention include C.I. I. Examples thereof include zinc phthalocyanine pigments described in CI Pigment Green 7, 10, 36, 37, 58, JP 2008-19383 A, JP 2007-320986 A, JP 2004-70342 A, and the like. It is not limited to.

  Examples of blue pigments that can be used in the present invention include C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, JP 2004-333817, Examples include aluminum phthalocyanine pigments described in Japanese Patent No. 4893859, but are not limited thereto.

  Purple pigments that can be used in the present invention include C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 27, 29, 30, 31, 32, 37, 39, 40, 42, 44, 47, 49, 50 and the like can be mentioned, but not limited thereto.

  Examples of inorganic pigments that can be used in the present invention include barium sulfate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, chromium oxide green, cobalt Examples thereof include metal oxide powders such as green, amber, titanium black, synthetic iron black, titanium oxide, and iron tetroxide, metal sulfide powder, and metal powder. Inorganic pigments are used in combination with organic pigments in order to ensure good coatability, sensitivity, developability and the like while maintaining a balance between saturation and lightness.

  Among these pigments, a basic resin can be used as the adsorbent (B) for pigments having an acidic surface, and a particularly remarkable effect is observed. Examples of the pigment having an acidic surface include C.I. I. Pigment yellow 150 and C.I. I. And CI Pigment Green 58.

  The coloring composition for a color filter of the present invention may contain a dye within a range that does not decrease heat resistance for color matching. Examples of dyes that can be contained include azo dyes, azo metal complex dyes, anthraquinone dyes, indigo dyes, thioindigo dyes, phthalocyanine dyes, methine dyes, diarylmethane dyes, and triarylmethane dyes , Xanthene dyes, thiazine dyes, cationic dyes, cyanine dyes, nitro dyes, quinoline dyes, naphthoquinone dyes, oxazine dyes, perylene dyes, diketopyrrolopyrrole dyes, quinacridone dyes, ansanthrone Examples thereof include, but are not limited to, dyes such as dyes, isoindolinone dyes, isoindoline dyes, indanthrone dyes, coumarin dyes, quinacridone dyes, pyranthrone dyes, flavanthrone dyes, and perinone dyes.

<Adsorbent having pigment adsorbing group (B)>
The adsorbent (B) adsorbed on the pigment surface itself has the ability to adsorb to the pigment and has the effect of adsorbing the pigment dispersant to the pigment. As the adsorbent (B) adsorbed on the pigment surface, for example,
Examples thereof include a dye derivative having a basic substituent, a dye derivative having an acidic substituent, and a resin having a basic group.

  As a pigment derivative having a basic substituent or an acidic substituent, the organic pigment, benzimidazolone compound, acridone compound, anthraquinone compound or triazine compound has a basic substituent, an acidic substituent, or a substituent. The compound etc. which introduce | transduced the phthalimidomethyl group which may be included are mention | raise | lifted.

<Dye derivative (Q) having a basic substituent>
A pigment derivative having a basic group is a compound in which a basic substituent is introduced into an organic pigment. Examples of the organic dye include azo series such as diketopyrrolopyrrole, azo, disazo, polyazo, anthraquinone, quinacridone, perinone, perylene, isoindoline, isoindolinone, quinophthalone, selenium, Examples include dyes such as metal complex systems. In addition, organic dyes constituting the dye derivatives include light yellow compounds such as anthraquinone, acridone, naphthalene, and triazine that are not generally called dyes. These can be used alone or in admixture of two or more.

  Examples of the basic group include substituents having an amine moiety, an imine moiety, an ammonium moiety, an amide moiety, an imide moiety, a urethane bond moiety, and the like. Especially, it is preferable that it is at least 1 basic group chosen from the group shown by following General formula (1), Formula (2), Formula (3), and Formula (4).

In general formula (1)-general formula (4),
X is —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ —, or a direct bond;
v is an integer from 1 to 10,
R ₁ and R ₂ are each independently an alkyl group that may be substituted, an alkenyl group that may be substituted, a phenyl group that may be substituted, or R ₁ and R ₂ together. An optionally substituted heterocyclic residue containing additional nitrogen, oxygen or sulfur atoms,
R ₃ is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group;
R ₄ , R ₅ , R ₆ , and R ₇ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group. ,
Y is —NR ₈ —Z—NR ₉ —, or a direct bond;
R ₈ and R ₉ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group,
Z is an alkylene group which may be substituted, an alkenylene group which may be substituted, or a phenylene group which may be substituted;
T is a substituent represented by the general formula (5) or a substituent represented by the general formula (6),
Q is a hydroxyl group, an alkoxyl group, a substituent represented by the general formula (5), or a general formula (6).

In general formula (5) and general formula (6),
X is —SO ₂ —, —CO—, —CH ₂ NHCOCH ₂ —, —CH ₂ —, or a direct bond;
v is an integer from 1 to 10,
R ₁ and R ₂ are each independently an alkyl group that may be substituted, an alkenyl group that may be substituted, a phenyl group that may be substituted, or R ₁ and R ₂ together. An optionally substituted heterocyclic residue containing additional nitrogen, oxygen or sulfur atoms,
R ₃ is an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group;
R ₄ , R ₅ , R ₆ , and R ₇ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group. ,
Y is —NR ₈ —Z—NR ₉ —, or a direct bond;
R ₈ and R ₉ are each independently a hydrogen atom, an optionally substituted alkyl group, an optionally substituted alkenyl group, or an optionally substituted phenyl group,
Z is an optionally substituted alkylene group, an optionally substituted alkenylene group, or an optionally substituted phenylene group.

Examples of the amine component used to form the substituent represented by the general formula (1) to the general formula (4) include:
Dimethylamine, diethylamine, methylethylamine, N, N-ethylisopropylamine, N, N-ethylpropylamine, N, N-methylbutylamine, N, N-methylisobutylamine, N, N-butylethylamine, N, N- tert-butylethylamine, diisopropylamine, dipropylamine, N, N-sec-butylpropylamine, dibutylamine, di-sec-butylamine, diisobutylamine, N, N-isobutyl-sec-butylamine, diamylamine, diisoamylamine, Dihexylamine, dicyclohexylamine, di (2-ethylhexyl) amine, dioctylamine, N, N-methyloctadecylamine, didecylamine, diallylamine, N, N-ethyl-1,2-dimethylpropylamine, , N-methylhexylamine, dioleylamine, distearylamine, N, N-dimethylaminomethylamine, N, N-dimethylaminoethylamine, N, N-dimethylaminoamylamine, N, N-dimethylaminobutylamine, N, N-diethylaminoethylamine, N, N-diethylaminopropylamine, N, N-diethylaminohexylamine, N, N-diethylaminobutylamine, N, N-diethylaminopentylamine, N, N-dipropylaminobutylamine, N, N-dibutyl Aminopropylamine, N, N-dibutylaminoethylamine, N, N-dibutylaminobutylamine, N, N-diisobutylaminopentylamine, N, N-methyl-laurylaminopropylamine, N, N-ethyl-hexylaminoe Ruamine, N, N-distearylaminoethylamine, N, N-dioleylaminoethylamine, N, N-distearylaminobutylamine, piperidine, 2-pipecoline, 3-pipecoline, 4-pipecoline, 2,4-rupetidin, 2,6-lupetidine, 3,5-lupetidine, 3-piperidinemethanol, pipecolic acid, isonipecotic acid, methyl isonicopetinate, ethyl isonicopetinate, 2-piperidineethanol, pyrrolidine, 3-hydroxypyrrolidine, N-aminoethylpiperidine, N -Aminoethyl-4-pipecoline, N-aminoethylmorpholine, N-aminopropylpiperidine, N-aminopropyl-2-pipecoline, N-aminopropyl-4-pipecoline, N-aminopropylmorpholine, N-methylpiperazine, N Butyl piperazine, N- methyl homopiperazine, 1-cyclopentylpiperazine, 1-amino-4-methylpiperazine, and 1-cyclopentyl piperazine and the like.

The organic dye constituting the pigment derivative having a basic group is, for example,
Diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, and polyazo, phthalocyanine dyes, diaminodianthraquinones, anthrapyrimidines, flavantrons, anthanthrone, indanthrone, pyranthrone, violanthrone, and quinacridone dyes And dyes such as dioxazine dyes, perinone dyes, perylene dyes, thioindigo dyes, isoindoline dyes, isoindolinone dyes, quinophthalone dyes, selenium dyes, and metal complex dyes.

  In addition, anthraquinone derivatives having basic groups and acridone derivatives having basic groups are alkyl groups such as methyl and ethyl groups, amino groups, nitro groups, hydroxyl groups, alkoxy groups such as methoxy groups and ethoxy groups, chlorine, etc. It may have a substituent such as halogen.

The triazine constituting the triazine derivative having a basic group is
Alkyl group (methyl group, ethyl group, butyl group, etc.), amino group, alkylamino group (dimethylamino group, diethylamino group, dibutylamino group, etc.), nitro group, hydroxyl group, alkoxy group (methoxy group, ethoxy group, butoxy group) Etc.), halogen (chlorine, bromine, etc.), phenyl group (which may be substituted with an alkyl group, amino group, alkylamino group, nitro group, hydroxyl group, alkoxy group, halogen, etc.), and phenylamino group (alkyl group) 1, 3,5-triazine optionally having a substituent such as an amino group, an alkylamino group, a nitro group, a hydroxyl group, an alkoxy group, or a halogen.

The pigment derivative, anthraquinone derivative and acridone derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, after introducing a substituent represented by formula (7) to formula (10) into an organic dye, anthraquinone or acridone, the substituent represented by formula (1) to formula (4) is reacted with the above substituent. Amine component to be formed, for example, N, N-dimethylaminopropylamine, N-methylpiperazine, diethylamine or 4- [4-hydroxy-6- [3- (dibutylamino) propylamino] -1,3,5-triazine It can be obtained by reacting 2-ylamino] aniline or the like.

General formula (7):
-SO ₂ Cl

General formula (8):
-COCl

General formula (9):
-CH ₂ NHCOCH ₂ Cl

General formula (10):
—CH ₂ Cl

  At the time of reaction of the general formulas (7) to (10) and the amine component, a part of the general formulas (7) to (10) may be hydrolyzed so that chlorine is substituted with a hydroxyl group. In that case, the general formula (7) and the general formula (8) are a sulfonic acid group and a carboxylic acid group, respectively, but both may be a free acid, and may be a 1 to 3 valent metal or the above monoamine. It may be a salt.

  Further, when the organic dye is an azo dye, the substituent represented by the formula (1) to the formula (4) is previously introduced into the diazo component or the coupling component, and then the coupling reaction is performed, thereby performing the azo pigment. Derivatives can also be produced.

  The triazine derivative having a basic group of the present invention can be synthesized by various synthetic routes. For example, an amine component starting from cyanuric chloride and forming a substituent represented by formula (1) to formula (4) on at least one chlorine of cyanuric chloride, such as N, N-dimethylaminopropylamine or N- It can be obtained by reacting methylpiperazine or the like and then reacting the remaining chlorine of cyanuric chloride with various amines or alcohols.

  In the coloring composition for a color filter of the present invention, the blending amount of the pigment derivative having a basic group is preferably 1 to 50% by weight, more preferably 3 to 30% by weight, most preferably based on the weight of the pigment. Preferably it is 5 to 25% by weight. If the pigment derivative having a basic group is less than 1% by weight, the effect of addition is difficult to obtain, and if it exceeds 50% by weight, heat resistance and light resistance may be deteriorated.

  Specific examples of the pigment derivative having a basic group of the present invention are shown below with compound numbers, but are not limited thereto.

〔化合物（１）中、ＣｕＰｃは、銅フタロシアニン残基である。〕 Compound 1

[In the compound (1), CuPc is a copper phthalocyanine residue. ]

〔化合物（２）中、ＣｕＰｃは、銅フタロシアニン残基である。〕 Compound 2

[In the compound (2), CuPc is a copper phthalocyanine residue. ]

Compound 3

Compound 4

Compound 5

Compound 6

Compound 7

Compound 8

<Dye derivative (R) having an acidic substituent>
The coloring composition for a color filter of the present invention further includes a dye derivative having an acidic functional group, an anthraquinone derivative having an acidic functional group, an acridone derivative having an acidic functional group, and a triazine derivative having an acidic functional group. A derivative having one or more kinds of acidic functional groups selected (hereinafter sometimes abbreviated as a derivative having an acidic functional group) can be used.

  The derivative having an acidic functional group used in the present invention will be described. The derivative having an acidic substituent used in the present invention is at least one derivative selected from the group of derivatives represented by the following general formula (11), the following general formula (12), and the following general formula (13). Can be used. Derivatives having an acidic substituent are classified into derivatives having no charge represented by the following general formula (11) and derivatives having a charge represented by the following general formulas (12) and (13).

General formula (11):
PZ ¹
(In General Formula (11), P is an organic dye residue, a heterocyclic residue which may have a substituent, or an aromatic residue which may have a substituent, and Z ¹ is A sulfonic acid group or a carboxyl group.)

Formula (12):
(PZ ² ) [N ⁺ (R ⁵ , R ⁶ , R ⁷ , R ⁸ )]
(In General Formula (12), P is an organic dye residue, a heterocyclic residue which may have a substituent, or an aromatic residue which may have a substituent, and R ⁵ is , R ⁶ , R ⁷ , and R ⁸ are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms, and Z ² is SO ₃ ^— or COO. ^- it can be).

General formula (13):
(P−Z ² ) _{x My} ⁺
(In the general formula (13), P is an organic pigment residue, heterocyclic residue which may have a substituent, or have a substituent an aromatic residues, M y ⁺ is , Metal ions such as lithium, sodium, potassium, magnesium, calcium, barium, iron, cobalt, nickel, copper, zinc, or aluminum ions, y is the valence of the ions, and x is x = y ÷ is a value obtained by the formula (Z number of ^2), Z ² is, SO ₃ ^- or COO ^- and is).

  Examples of the organic dye residue represented by P in the general formulas (11) to (13) include diketopyrrolopyrrole dyes, azo dyes such as azo, disazo, polyazo, phthalocyanine dyes, diaminodianthraquinone, anthra Anthraquinone dyes such as pyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone, quinacridone dye, dioxazine dye, perinone dye, perylene dye, thioindigo dye, isoindoline dye, isoindolinone System dyes, quinophthalone dyes, selenium dyes, metal complex dyes, and the like.

  Examples of the heterocyclic residue and aromatic ring residue represented by P in the general formulas (11) to (13) include thiophene, furan, pyridine, pyrazole, pyrrole, imidazole, isoindoline, and isoindolinone. Benzimidazolone, benzthiazole, benztriazole, indole, quinoline, carbazole, acridine, benzene, naphthalene, anthracene, fluorene, phenanthrene, anthraquinone, and acridone. These heterocyclic residues and aromatic ring residues are alkyl groups (such as methyl, ethyl, and butyl groups), amino groups, alkylamino groups (such as dimethylamino groups, diethylamino groups, and dibutylamino groups), Nitro group, hydroxyl group, alkoxy group (methoxy group, ethoxy group, butoxy group, etc.), halogen (chlorine, bromine, fluorine, etc.), phenyl group (alkyl group, amino group, alkylamino group, nitro group, hydroxyl group, alkoxy) Group, and optionally substituted with halogen, etc.), phenylamino group (which may be substituted with alkyl group, amino group, alkylamino group, nitro group, hydroxyl group, alkoxy group, halogen, etc.), etc. You may have the substituent of.

  P in the pigment derivatives represented by the general formulas (11) to (13) does not necessarily match the chemical structure of the pigment used in the colored resin composition and the chemical structure of the organic dye residue. However, in consideration of the hue of the ink to be finally produced, when used for dispersion of green, it is used for dispersion of blue, green, or yellow pigment derivatives, and yellow pigments. For yellow pigment derivatives, red, orange or yellow pigment derivatives for use in dispersing red pigments, blue or purple pigment derivatives for use in dispersing blue pigments As described above, it is possible to produce a pigment dispersion excellent in hue by using a pigment having a hue close to that of the pigment to be dispersed or a colorless pigment.

Z ¹ in the general formula (11) may be present in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to P in the general formula (11).

Z ² in the general formula (12) may be present in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to P in the general formula (12). At the same time, the same number of [N ⁺ (R ⁵ , R ⁶ , R ⁷ , R ⁸ )] may exist depending on the number of Z ² .

Z ² in the general formula (13) may be present in the range of 0.5 to 8.0, preferably 0.7 to 3.0, with respect to P in the general formula (13). At the same time, the number of x may be appropriately changed according to the number of Z ² and the ionic valence y of M.

  Specific examples of the dye derivative having an acidic functional group of the present invention are shown below with compound numbers, but are not limited thereto.

Compound 9

Compound 10

Compound 11

Compound 12

Compound 13

<Vinyl resin having a basic group (S)>
When the pigment surface is acidic, a basic resin can be used as the adsorbent (B) adsorbed on the pigment surface. The adsorbing group of the basic resin is not particularly limited, but is preferably a vinyl resin having a tertiary amino group.

  The amine value of the basic resin is preferably 50 to 500 mgKOH / g from the viewpoint of the viscosity of the dispersion and the viscosity stability. A more preferred amine value range is 310 to 350 mg KOH / g.

  Furthermore, the basic resin preferably has a hydroxyl value of 20 to 80 mgKOH / g. A more preferable range of the hydroxyl value is 30 to 60 mgKOH / g. When the hydroxyl value is 20 to 80 mgKOH / g, the heat resistance, solvent resistance, and chemical resistance of the film in the case of a color filter are improved.

  The number average molecular weight of the vinyl resin (S) of the present invention is preferably 500 to 30,000. If it is less than 500 or more than 30,000, the viscosity and viscosity stability of the pigment dispersion may deteriorate, which is not preferable.

  The vinyl resin (S) of the present invention comprises an ethylenically unsaturated monomer having a tertiary amino group, an ethylenically unsaturated monomer having a hydroxyl group in a preferred embodiment, and other ethylenically unsaturated monomers as required. It can be obtained by polymerizing with a monomer.

Examples of the ethylenically unsaturated monomer having a tertiary amino group include:
N, such as N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-dimethylaminopropyl (meth) acrylate, and N, N-diethylaminopropyl (meth) acrylate N-dialkylamino group-containing (meth) acrylates;
N, such as N, N-dimethylaminoethyl (meth) acrylamide, N, N-diethylaminoethyl (meth) acrylamide, N, N-dimethylaminopropyl (meth) acrylamide, and N, N-diethylaminopropyl (meth) acrylamide Examples include N-dialkylamino group-containing (meth) acrylamides.

  Among these, N, N-dimethylaminoethyl (meth) acrylate is preferable from the viewpoint of dispersibility.

As an ethylenically unsaturated monomer having a hydroxyl group, for example,
Hydroxyalkyls such as 2-hydroxyethyl (meth) acrylate, 2 (or 3) -hydroxypropyl (meth) acrylate, 2 (or 3 or 4) -hydroxybutyl (meth) acrylate and cyclohexanedimethanol mono (meth) acrylate ( (Meth) acrylates;
Alkyl-α-hydroxyalkyl acrylates such as ethyl-α-hydroxymethyl acrylate;
N- (hydroxyalkyl) (meth) such as N- (2-hydroxyethyl) (meth) acrylamide, N- (2-hydroxypropyl) (meth) acrylamide, and N- (2-hydroxybutyl) (meth) acrylamide Acrylamides;
Hydroxyalkyl vinyl ethers such as 2-hydroxyethyl vinyl ether, 2- (or 3-) hydroxypropyl vinyl ether, and 2- (or 3- or 4-) hydroxybutyl vinyl ether; and
Examples thereof include hydroxyalkyl allyl ethers such as 2-hydroxyethyl allyl ether, 2- (or 3-) hydroxypropyl allyl ether, and 2- (or 3- or 4-) hydroxybutyl allyl ether.

  Moreover, the monomer which has two hydroxyl groups, such as glycerol mono (meth) acrylate, is also mentioned.

  Examples of other ethylenically unsaturated monomers include acrylic monomers and monomers other than acrylic monomers.

As an acrylic monomer, for example,
Methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, 2- Alkyl (meth) acrylates such as ethylhexyl (meth) acrylate, stearyl (meth) acrylate, and lauryl (meth) acrylate;
Cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, dicyclopentanyloxyethyl (meth9 acrylate, dicyclopentenyl (meth) acrylate, isobornyl (meth) acrylate, and adamantyl (meth) acrylate, etc. Formula alkyl (meth) acrylates;
(Meth) acrylates having a heterocyclic substituent such as tetrahydrofurfuryl (meth) acrylate and 3-methyloxetanyl (meth) acrylate;
(Meth) acrylates having an aromatic substituent such as phenyl (meth) acrylate, benzyl (meth) acrylate, phenoxyethylene oxide-modified (meth) acrylate, and paracumylphenoxyethylene oxide-modified (meth) acrylate;
Alkoxypolyalkylene glycol (meth) acrylates such as methoxypolypropylene glycol (meth) acrylate and ethoxypolyethylene glycol (meth) acrylate; and
(Meth) acrylamide (in the case of “(meth) acrylamide”, it means acrylamide and / or methacrylamide; the same shall apply hereinafter), N, N-dimethyl (meth) acrylamide, N, N -(Meth) acrylamides such as diethyl (meth) acrylamide, N-isopropyl (meth) acrylamide, diacetone (meth) acrylamide, and acryloylmorpholine.

Moreover, as a monomer other than the acrylic monomer, for example,
Styrenes such as styrene and α-methylstyrene;
Vinyl ethers such as ethyl vinyl ether, n-propyl vinyl ether, isopropyl vinyl ether, n-butyl vinyl ether, and isobutyl vinyl ether; and
Examples include vinyl acetate and fatty acid vinyls such as vinyl propionate. The monomer other than the acrylic monomer can be used in combination with the acrylic monomer.

  Moreover, a carboxyl group-containing ethylenically unsaturated monomer can be used alone or in combination with the monomer.

As the carboxyl group-containing ethylenically unsaturated monomer, for example,
One type or two or more types can be selected from acrylic acid, methacrylic acid, ε-couplerlactone-added acrylic acid, ε-couplerlactone-added methacrylic acid, itaconic acid, maleic acid, fumaric acid, and crotonic acid. .

<Dispersant (C)>
The dispersant (C) used in the present invention is a linear dispersant (C1) having a site (x) for salt formation with a pigment adsorbing group and having a number average molecular weight of 5000 or more, and / or The comb-shaped dispersant (C2) has a site (x) that forms a salt with a pigment adsorbing group in the chain, and has a number average molecular weight of 5000 or more in the side chain.
The part (x) that forms a salt with the adsorbent (B) acts as a pigment adsorbing group, and the part other than the part (x) that forms a salt with the adsorbent (B) acts as a steric hindrance group.

(Pigment adsorption group and site for salt formation (x))
The (x) is not particularly limited as long as it forms a salt with the adsorbent (B). For example, acidic functional groups such as sulfonic acid groups, phosphoric acid groups, and carboxyl groups, primary, secondary, and tertiary amino acids. And basic functional groups such as groups.

(Excluding the part (x) that forms a salt with the pigment adsorption group)
The part other than (x) of the dispersant (C) is not particularly limited as long as it has an affinity for the solvent, and examples thereof include alkyl chains, polyesters, polyamides, polyurethanes, polyethers, and vinyl polymers. However, polyesters or vinyl polymers are particularly preferred from the standpoint of ease of synthesis and ease of solvent affinity control.

(Linear dispersant (C1))
All the linear dispersants (C1) can be produced by using a known method. For example, JP 2009-251481, JP 2007-23195, and 1996-143651. Can be synthesized using a known method as shown in FIG. As an example of the production method of the linear dispersant (C1), the dispersant (x) is a carboxyl group, a vinyl polymer having one hydroxyl group at one end is used as a raw material, and trimellitic anhydride is hydroxyl group. It can manufacture by adding to.

  The number average molecular weight in the linear dispersant (C1) refers to the molecular weight of the entire vinyl polymer obtained by adding trimellitic anhydride to a hydroxyl group in the above production method, for example.

(Comb-shaped dispersant (C2))
All the comb-shaped dispersants (C2) can be produced by using known methods, for example, using known methods as disclosed in JP2009-251481A and JP2009-251481A. Can be synthesized. As an example of a method for producing a comb-shaped dispersant (C2), a dispersant in which (x) is a carboxyl group is obtained by using pyromellitic anhydride as a hydroxyl group from a vinyl polymer having two hydroxyl groups at one end. It can manufacture by adding to.

  The number average molecular weight of the side chain in the comb-type dispersant (C2) refers to the molecular weight of a vinyl polymer having two hydroxyl groups at one end in the above production method, for example.

  In the dispersant (C) used in the present invention, it is preferable that (x) is a carboxyl group, a polymer (X) having a hydroxyl group at one end, an aromatic tricarboxylic acid anhydride (Y1) and / or an aromatic group. It is preferable that it is a dispersing agent which has an aromatic carboxyl group formed by making tetracarboxylic dianhydride (Y2) react.

  All the polymers (X) having a hydroxyl group at one end can be produced using a known method. For example, it can be obtained by mixing a compound having a hydroxyl group and a thiol group in the molecule with an ethylenically unsaturated monomer and heating by a method as disclosed in JP-A-2009-251481.

  Examples of the compound having a hydroxyl group and a thiol group in the molecule include mercaptomethanol, 2-mercaptoethanol, 3-mercapto-1-propanol, 1-mercapto-2-butanol, and 2-mercapto-3-butanol. -Mercapto-1,1-methanediol, 1-mercapto-1,1-ethanediol, 3-mercapto-1,2-propanediol (thioglycerin), 2-mercapto-1,2-propanediol, 2-mercapto -2-methyl-1,3-propanediol, 2-mercapto-2-ethyl-1,3-propanediol, 1-mercapto-2,2-propanediol, 2-mercaptoethyl-2-methyl-1,3 -Propanediol and 2-mercaptoethyl-2-ethyl-1,3-propanediol And the like.

  Examples of the aromatic tricarboxylic acid anhydride (Y1) include benzene tricarboxylic acid anhydride (1,2,3-benzene tricarboxylic acid anhydride, trimellitic acid anhydride (1,2,4-benzene tricarboxylic acid anhydride). Etc.), naphthalenetricarboxylic acid anhydride (1,2,4-naphthalenetricarboxylic acid anhydride, 1,4,5-naphthalenetricarboxylic acid anhydride, 2,3,6-naphthalenetricarboxylic acid anhydride, 1,2,8 -Naphthalene tricarboxylic acid anhydride, etc.), 3,4,4'-benzophenone tricarboxylic acid anhydride, 3,4,4'-biphenyl ether tricarboxylic acid anhydride, 3,4,4'-biphenyl tricarboxylic acid anhydride, 2 , 3,2′-biphenyltricarboxylic acid anhydride, 3,4,4′-biphenylmethanetricarboxylic acid anhydride, and 3,4,4 '- biphenyl sulfonic tricarboxylic acid anhydride and the like.

  As aromatic tetracarboxylic dianhydride (Y2), pyromellitic dianhydride, ethylene glycol ditrimellitic anhydride ester, propylene glycol ditrimellitic anhydride ester, butylene glycol ditrimellitic anhydride ester, 3, 3 ', 4,4'-benzophenone tetracarboxylic dianhydride, 3,3', 4,4'-biphenylsulfone tetracarboxylic dianhydride, 1,4,5,8-naphthalene tetracarboxylic dianhydride 2,3,6,7-naphthalenetetracarboxylic dianhydride, 3,3 ′, 4,4′-biphenyl ether tetracarboxylic dianhydride, 3,3 ′, 4,4′-dimethyldiphenylsilanetetra Carboxylic dianhydride, 3,3 ′, 4,4′-tetraphenylsilane tetracarboxylic dianhydride, 1,2,3,4-fura Tetracarboxylic dianhydride, 4,4′-bis (3,4-dicarboxyphenoxy) diphenyl sulfide dianhydride, 4,4′-bis (3,4-dicarboxyphenoxy) diphenylsulfone dianhydride, 4 , 4′-bis (3,4-dicarboxyphenoxy) diphenylpropane dianhydride, 3,3 ′, 4,4′-perfluoroisopropylidenediphthalic dianhydride, 3,3 ′, 4,4 ′ -Biphenyltetracarboxylic dianhydride, bis (phthalic acid) phenylphosphine oxide dianhydride, p-phenylene-bis (triphenylphthalic acid) dianhydride, m-phenylene-bis (triphenylphthalic acid) dianhydride Bis (triphenylphthalic acid) -4,4′-diphenyl ether dianhydride, bis (triphenylphthalic acid) -4,4′-diphenylmeta Dianhydride, 9,9-bis (3,4-dicarboxyphenyl) fluorene dianhydride, 9,9-bis [4- (3,4-dicarboxyphenoxy) phenyl] fluorene dianhydride, 3,4 -Dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic dianhydride or 3,4-dicarboxy-1,2,3,4-tetrahydro-6-methyl-1-naphthalene succinic acid A dianhydride etc. are mentioned.

  In the dispersant (C) used in the present invention, the site (x) that forms a salt with the pigment adsorbing group has a good combination of (x) being basic when the adsorbent is an acidic derivative, and the adsorbent is a basic derivative. In addition, in the case of a basic vinyl resin, a combination in which (x) is acidic is preferable.

  As a preferred combination of the adsorbent (B) and the dispersant (C), the adsorbent (B) is a vinyl resin (S) having a basic group, and the dispersant (C) is a polymer having a hydroxyl group at one end. A dispersant (P) having an aromatic carboxyl group obtained by reacting (X) with an aromatic tricarboxylic acid anhydride (Y1) and / or an aromatic tetracarboxylic dianhydride (Y2) is preferable. .

<Photopolymerizable monomer>
Photopolymerizable monomers that can be used in the present invention include monomers or oligomers that are cured by ultraviolet rays or heat to produce transparent resins, and these may be used alone or in combination of two or more. Can do. The amount of the monomer is preferably 5 to 400% by weight based on the total weight of the colorant (100% by weight), and more preferably 10 to 300% by weight from the viewpoint of photocurability and developability. preferable.

  Examples of monomers and oligomers that are cured by ultraviolet rays or heat to produce a transparent resin include methyl (meth) acrylate, ethyl (meth) acrylate, 2-hydroxyethyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate. , Cyclohexyl (meth) acrylate, β-carboxyethyl (meth) acrylate, polyethylene glycol di (meth) acrylate, 1,6-hexanediol di (meth) acrylate, triethylene glycol di (meth) acrylate, tripropylene glycol di ( (Meth) acrylate, trimethylolpropane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, 1,6-hexanediol diglycy 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, tricyclodeca Nyl (meth) acrylate, ester acrylate, methylolated melamine (meth) acrylate ester, epoxy (meth) acrylate, urethane acrylate and other acrylic esters and methacrylate esters, (meth) acrylic acid, styrene, vinyl acetate, Hydroxyethyl vinyl ether, ethylene glycol divinyl ether, pentaerythritol trivinyl ether, (meth) acrylamide, N-hydroxymethyl Examples include, but are not necessarily limited to, til (meth) acrylamide, N-vinylformamide, acrylonitrile and the like.

<Photopolymerization initiator>
In the blue coloring composition for a color filter of the present invention, when the composition is cured by ultraviolet irradiation and a filter segment is formed by a photolithographic method, a photopolymerization initiator or the like is added to add a solvent developing type or an alkali developing type. It can be adjusted in the form of a colored resist material. The blending amount when using the photopolymerization initiator is preferably 5 to 200% by weight based on the total amount of the colorant, and 10 to 150% by weight from the viewpoint of photocurability and developability. More preferred.

  Examples of the photopolymerization initiator include 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1- Hydroxycyclohexyl phenyl ketone, 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2- (dimethylamino) -2-[(4-methylphenyl) methyl] -1 Acetophenone compounds such as-[4- (4-morpholinyl) phenyl] -1-butanone or 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one; benzoin, benzoin Methyl ether, benzoin ethyl ether, benzoin isopropyl ether, or Benzoin compounds such as benzyl dimethyl ketal; benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4′-methyldiphenyl sulfide, or 3,3 ′, Benzophenone compounds such as 4,4′-tetra (t-butylperoxycarbonyl) benzophenone; thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone, or 2,4-diethylthioxanthone Thioxanthone compounds such as 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxy) Enyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-piperonyl-4,6-bis (trichloro Methyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl-s-triazine, 2- (naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2 -(4-Methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine, or 2,4-trichloromethyl- Triazine compounds such as (4′-methoxystyryl) -6-triazine; 1,2-octanedione, 1- [4- (phenylthio)-, 2- (O-benzoyloxime) Or an oxime ester compound such as O- (acetyl) -N- (1-phenyl-2-oxo-2- (4′-methoxy-naphthyl) ethylidene) hydroxylamine; bis (2,4,6-trimethylbenzoyl) ) Phosphine compounds such as phenylphosphine oxide or 2,4,6-trimethylbenzoyldiphenylphosphine oxide; quinone compounds such as 9,10-phenanthrenequinone, camphorquinone and ethylanthraquinone; borate compounds; carbazole compounds An imidazole compound; or a titanocene compound.

  These photopolymerization initiators can be used alone or in combination of two or more at any ratio as required. These photopolymerization initiators are preferably 5 to 200% by weight, based on the total amount of the colorant in the blue coloring composition for color filters (100% by weight), from the viewpoint of photocurability and developability. More preferably, it is 10 to 150% by weight.

<Sensitizer>
Furthermore, the blue coloring composition for a color filter of the present invention can contain a sensitizer.
Sensitizers include chalcone derivatives, unsaturated ketones such as dibenzalacetone, 1,2-diketone derivatives such as benzyl and camphorquinone, benzoin derivatives, fluorene derivatives, naphthoquinone derivatives, anthraquinone derivatives , Xanthene derivatives, thioxanthene derivatives, xanthone derivatives, thioxanthone derivatives, coumarin derivatives, ketocoumarin derivatives, cyanine derivatives, merocyanine derivatives, oxonol derivatives, and other polymethine dyes, acridine derivatives, azine derivatives, thiazine derivatives, oxazine derivatives, indoline derivatives, Azulene derivatives, azurenium derivatives, squarylium derivatives, porphyrin derivatives, tetraphenylporphyrin derivatives, triarylmethane derivatives, tetrabenzoporphyrin derivatives, Trapirazinoporphyrazine derivatives, phthalocyanine derivatives, tetraazaporphyrazine derivatives, tetraquinoxalyloporphyrazine derivatives, naphthalocyanine derivatives, subphthalocyanine derivatives, pyrylium derivatives, thiopyrylium derivatives, tetraphylline derivatives, annulene derivatives, spiropyran derivatives, spirooxazine Derivatives, thiospiropyran derivatives, metal arene complexes, organoruthenium complexes, or Michler's ketone derivatives, α-acyloxy esters, acylphosphine oxides, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, camphorquinone, ethyl Anthraquinone, 4,4'-diethylisophthalophenone, 3,3 'or 4,4'-tetra (t-butylperoxycarbonyl) benzophen Non, 4,4′-diethylaminobenzophenone and the like.

  More specifically, edited by Shin Okawara et al., “Dye Handbook” (1986, Kodansha), edited by Shin Okawara et al., “Chemistry of Functional Dye” (1981, CMC), edited by Tadasaburo Ikemori et al. Examples include, but are not limited to, sensitizers described in "Special Functional Materials" (1986, CMC). In addition, a sensitizer that absorbs light from the ultraviolet region to the near infrared region can also be contained.

  Two or more kinds of sensitizers may be used in any ratio as required. The blending amount when using the sensitizer is preferably 3 to 60% by weight based on the total weight of the photopolymerization initiator contained in the colored composition (100% by weight). From the viewpoint of developability, it is more preferably 5 to 50% by weight.

<Solvent>
In the coloring composition for a color filter of the present invention, a pigment is sufficiently dispersed in a pigment carrier and applied on a transparent substrate such as glass so that a dry film thickness is 0.2 to 5 μm to form a filter segment. A solvent can be included to facilitate the process.

As a solvent, for example,
1,2,3-trichloropropane, 1,3-butanediol, 1,3-butylene glycol, 1,3-butylene glycol diacetate, 1,4-dioxane, 2-heptanone, 2-methyl-1,3- Propanediol, 3,5,5-trimethyl-2-cyclohexen-1-one, 3,3,5-trimethylcyclohexanone, ethyl 3-ethoxypropionate, 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, m-dichlorobenzene, N, N- Dimethylacetamide, N, N-dimethylformamide, n-butyl alcohol, n-butylbenzene, n-propyl acetate, N-methylpyrrolidone, o-xylene, o-chloro Ruene, o-diethylbenzene, o-dichlorobenzene, p-chlorotoluene, p-diethylbenzene, sec-butylbenzene, tert-butylbenzene, γ-butyrolactone, isobutyl alcohol, isophorone, ethylene glycol diethyl ether, ethylene glycol dibutyl ether, ethylene Glycol monoisopropyl ether, ethylene glycol monoethyl ether, ethylene glycol monoethyl ether acetate, ethylene glycol monotertiary 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 Monoethyl 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, di Propylene glycol dimethyl ether, dipropylene glycol methyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, dipropylene glycol monopropyl ether, dipropylene glycol Methyl 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 , Acetic acid Propyl, or dibasic acid esters and the like, used alone or in combination.

  When the colored composition is cured by ultraviolet irradiation, an active energy ray polymerizable initiator or the like is added to the colored composition for color filter.

<Coloring composition for color filter>

The colored composition for color filter of the present invention can be classified into a colored composition for color filter (paste) and a colored composition for color filter (resist).
The coloring composition (paste) for the color filter of the present invention is mixed with various solvents, resins, additives, etc., if necessary, and dispersed with a horizontal sand mill, vertical sand mill, annular bead mill, attritor, etc. A colored composition (paste) for a color filter obtained by dispersing the composition in a varnish can be prepared. It can also be produced by mixing several types of pigments separately dispersed on a pigment carrier.
The coloring composition for a color filter of the present invention is a coarse particle of 5 μm or more, preferably a coarse particle of 1 μm or more, more preferably a coarse particle of 0.5 μm or more by means of centrifugation, sintered filter, membrane filter or the like. It is preferable to remove the mixed dust.
The color filter coloring composition (resist) can be prepared as a solvent developing type or alkali developing type color filter coloring resist (resist). A colored composition (resist) for a solvent development type or alkali development type color filter generally comprises a thermoplastic resin, a thermosetting resin or a photosensitive resin, an ethylenically unsaturated monomer, a photopolymerization initiator, A pigment is dispersed in a composition containing an organic solvent.
The photopolymerization initiator may be added at the stage of preparing the color filter coloring composition (resist), or may be added later to the prepared color filter coloring composition (resist).

<Color filter>
Next, the color filter of the present invention will be described.
The color filter of the present invention is provided with a filter segment or a black matrix formed from the coloring composition for a color filter of the present invention on a transparent substrate, and a general color filter includes at least one red filter segment, At least one green filter segment and at least one blue filter segment, or at least one magenta filter segment, at least one cyan filter segment, and at least one yellow filter segment.

  Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “parts” means “parts by weight”.

A method for measuring parameters described in the examples will be described.
<Number average molecular weight>
The molecular weight of the resin of the present invention is measured in polystyrene using HLC-8220GPC (manufactured by Tosoh Corporation) as a device, TSK-GEL SUPER HZM-N connected in series as a column, and THF as a solvent. The number average molecular weight of
<Amine number>
The amine value refers to the number of milligrams of potassium hydroxide that is molar equivalent to the amino group in 1 gram of the sample solid, and is a value measured according to the method of ASTM D2074.

  Prior to Examples, among the adsorbents (B) having a pigment adsorbing group, a method for producing a vinyl resin (S) having a basic group, a dispersant (C), a binder resin (D), and a fine pigment (A). Will be described.

<Production of vinyl resin (S) having a basic group>
(Vinyl resin having a basic group (S-1)) Production Example 1
A reaction vessel equipped with a gas introduction tube, a condenser, a stirring blade, and a thermometer was charged with 133 parts of methoxypropyl acetate and heated to 100 ° C. while purging with nitrogen. A dripping tank is charged with 180 parts of N, N-dimethylaminoethyl methacrylate, 20 parts of 2-hydroxyethyl methacrylate, 61 parts of methoxypropyl acetate, and 6 parts of 2,2′-azobis (2,4-dimethylvaleronitrile), and uniform. Then, the mixture was added dropwise to the reaction vessel over 2 hours, and then the reaction was continued at the same temperature for 3 hours to obtain a vinyl resin solution having a tertiary amino group. After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. Propylene glycol monomethyl ether was added to the previously synthesized resin solution so that the nonvolatile content was 50% by weight. Acetate was added to obtain a vinyl resin (S-1) solution having a tertiary amino group having an amine value per solid content of 315 mgKOH / g and a number average molecular weight of 3000.

<Production of linear dispersing agent (C1)>
(Linear dispersant (C1-1)) Production Example 2
In a reaction vessel equipped with a gas introduction tube, a condenser, a stirring blade, and a thermometer, 80 parts of methyl methacrylate, 120 parts of ethyl acrylate, and 40 parts of methoxypropyl acetate were charged and replaced with nitrogen gas. Heat the inside of the reaction vessel to 80 ° C., add 2.2 parts of 3-mercapto-1,2-propanediol, then divide 0.2 part of 2,2′-azobisisobutyronitrile into 20 portions. Every 30 minutes, the reaction was continued for 12 hours at 80 ° C., and it was confirmed that 95% had reacted by solid content measurement. Next, 12 parts of trimellitic anhydride, 135 parts of methoxypropyl acetate and 0.40 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as catalyst were added at 120 ° C. The reaction was carried out for 2 hours at 80 ° C. for 5 hours, and it was confirmed by titration that 90% or more of the acid anhydride had been half-esterified. Sample 2 g of resin solution, heat-dry at 180 ° C. for 20 minutes, measure the nonvolatile content, add propylene glycol monomethyl ether acetate so that the nonvolatile content becomes 50% by weight, and form a linear chain having a number average molecular weight of 10600 Dispersant (C1-1) was obtained.

(Linear dispersant (C1-2)) Production Example 3
A reaction vessel equipped with a nitrogen gas inlet tube, a condenser, and a stirrer was charged with 18.6 g of lauryl alcohol, 913.6 g of ε-caprolactone monomer and 0.06 g of tetrabutyl titanate, and replaced with nitrogen gas, and then at 120 ° C. for 3 hours. Heated and stirred. The disappearance of the caprolactone monomer was confirmed by a GPC (gel permeation chromatography) RI detector using tetrahydrofuran as an eluent. After cooling to 40 ° C. or lower, mixed with 0.85 g of polyphosphoric acid having 116% orthophosphoric acid content, gradually heated, heated with stirring at 80 ° C. for 6 hours, a linear chain having a number average molecular weight of 9500 A dispersant (C1-2) was obtained.

(Linear dispersant (C1-3)) Production Example 4
In a reaction vessel equipped with a gas introduction tube, a condenser, a stirring blade, and a thermometer, 80 parts of methyl methacrylate, 120 parts of ethyl acrylate, and 40.5 parts of methoxypropyl acetate were charged and replaced with nitrogen gas. After heating the inside of the reaction vessel to 80 ° C. and adding 4.4 parts of 3-mercapto-1,2-propanediol, 0.2 part of 2,2′-azobisisobutyronitrile is divided into 20 times. Every 30 minutes, the reaction was continued for 12 hours at 80 ° C., and it was confirmed that 95% had reacted by solid content measurement. Next, 24 parts of trimellitic anhydride, 145.9 parts of methoxypropyl acetate, and 0.40 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as catalyst were added. The reaction was carried out at 2 ° C. for 2 hours and at 80 ° C. for 5 hours, and it was confirmed by titration that 90% or more of the acid anhydride had been half-esterified. Sample 2 g of resin solution, heat dry at 180 ° C. for 20 minutes, measure the non-volatile content, add propylene glycol monomethyl ether acetate so that the non-volatile content is 50% by weight, and form a linear chain with a number average molecular weight of 5100 Dispersant (C1-3) was obtained.

(Linear dispersant (C1-4)) Production Example 5
In a 2 liter glass reaction flask equipped with a stirrer, Dimroth condenser, thermometer, and air inlet tube, 11.6 parts hydroxyethyl acrylate, 1027 parts ε-caprolactone, 0.08 parts stannous chloride Then, 2 parts of methylhydroquinone was taken, heated to 100 ° C., and reacted until the remaining lactone monomer was 1% or less. Next, the temperature of the product was lowered to 50 ° C., and 10.0 parts of 2-methylpiperidine was added and reacted with stirring. It was confirmed by 1H-NMR that the acrylic group had disappeared, and the reaction was terminated to obtain a linear dispersant (C1-4) having a number average molecular weight of 9800.

(Linear dispersant (C1-5)) Production Example 6
In a 2 liter glass reaction flask equipped with a stirrer, Dimroth condenser, thermometer, and air inlet tube, 11.6 parts hydroxyethyl acrylate, 513.6 parts ε-caprolactone, 0.1% stannous chloride. 08 parts and 2 parts of methylhydroquinone were taken and heated to 100 ° C. until the remaining lactone monomer was 1% or less. Next, the temperature of the product was lowered to 50 ° C., and 10.0 parts of 2-methylpiperidine was added and reacted with stirring. The reaction was terminated after confirming disappearance of the acrylic group by 1H-NMR to obtain a linear dispersant (C1-5) having a number average molecular weight of 5200.

(Linear dispersant (C1-6))
In a reaction vessel equipped with a gas introduction tube, a condenser, a stirring blade, and a thermometer, 80 parts of methyl methacrylate, 120 parts of ethyl acrylate, and 40.9 parts of methoxypropyl acetate were charged and replaced with nitrogen gas. Heat the inside of the reaction vessel to 80 ° C., add 6.6 parts of 3-mercapto-1,2-propanediol, and then add 0.2 part of 2,2′-azobisisobutyronitrile in 20 portions. Every 30 minutes, the reaction was continued for 12 hours at 80 ° C., and it was confirmed that 95% had reacted by solid content measurement. Next, 36 parts of trimellitic anhydride, 157.4 parts of methoxypropyl acetate, and 0.40 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as catalyst were added. The reaction was carried out at 2 ° C. for 2 hours and at 80 ° C. for 5 hours, and it was confirmed by titration that 90% or more of the acid anhydride had been half-esterified. 2 g of resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, propylene glycol monomethyl ether acetate was added so that the nonvolatile content was 50% by weight, and a linear chain having a number average molecular weight of 3500 Dispersant (C1-6) was obtained.

(Linear dispersant (C1-7))
In a 2 liter glass reaction flask equipped with a stirrer, Dimroth condenser, thermometer, and air inlet tube, 11.6 parts of hydroxyethyl acrylate, 330.5 parts of ε-caprolactone, 0.1% of stannous chloride. 08 parts and 2 parts of methylhydroquinone were taken and heated to 100 ° C. until the remaining lactone monomer was 1% or less. Next, the temperature of the product was lowered to 50 ° C., and 10.0 parts of 2-methylpiperidine was added and reacted with stirring. It was confirmed by 1H-NMR that the acrylic group had disappeared, and the reaction was terminated to obtain a linear dispersant (C1-7) having a number average molecular weight of 4000.

<Manufacture of comb-shaped dispersant (C2)>
(Comb Dispersant (C2-1)) Production Example 7
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 45.0 parts of methyl methacrylate, 15.0 parts of methacrylic acid, and 40.0 parts of ethyl acrylate, and replaced with nitrogen gas. The inside of the reaction vessel is heated to 80 ° C. and dissolved in 1.0 part of 3-mercapto-1,2-propanediol and 0.1 part of 2,2′-azobisisobutyronitrile in 45.3 parts of cyclohexanone. The solution was added and reacted for 10 hours. It was confirmed that 95% had reacted by solid content measurement. At this time, the number average molecular weight was 9,500. Next, 8.0 parts of Ricacid BT-100 (manufactured by Shin Nippon Chemical Co., Ltd.), 69.2 parts of cyclohexanone, and 0.2 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were added. And reacted at 120 ° C. for 7 hours. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value. After the reaction was completed, cyclohexanone was added so that the non-volatile content was 50% by weight to obtain a solution of a comb-shaped dispersant (C2-1) having a number average molecular weight of 25000.

(Comb Dispersant (C2-2)) Production Example 8
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 45.0 parts of methyl methacrylate, 15.0 parts of methacrylic acid, and 40.0 parts of ethyl acrylate, and replaced with nitrogen gas. The reaction vessel was heated to 80 ° C. and dissolved in 3.2 parts of 3-mercapto-1,2-propanediol and 0.1 part of 2,2′-azobisisobutyronitrile was dissolved in 45.3 parts of cyclohexanone. The solution was added and reacted for 10 hours. It was confirmed that 95% had reacted by solid content measurement. At this time, the number average molecular weight was 5900. Next, 8.1 parts of Ricacid BT-100 (manufactured by Shin Nippon Chemical Co., Ltd.), 69.2 parts of cyclohexanone, and 0.2 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were added. And reacted at 120 ° C. for 7 hours. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value. After the reaction was completed, cyclohexanone was added so that the nonvolatile content was 50% by weight to obtain a solution of a comb-shaped dispersant (C2-2) having a number average molecular weight of 15000.

(Comb Dispersant (C2-3)) Production Example 9
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 500 parts of methyl methacrylate, 11 parts of thioglycerol, and 511 parts of methoxypropyl acetate and replaced with nitrogen gas. The inside of the reaction vessel was heated to 90 ° C., and 0.50 part of AIBN was added, followed by reaction for 7 hours. After confirming that 95% had reacted by measuring the non-volatile content, the mixture was cooled to room temperature to obtain a 50% non-volatile solution of a vinyl polymer having a weight average molecular weight of 9300 and having two free hydroxyl groups in one end region. Subsequently, 45.2 parts of isophorone diisocyanate, 45.1 parts of methoxypropyl acetate, and 0.11 part of dibutyltin dilaurate as a catalyst were charged and replaced with nitrogen gas. The reaction vessel was heated to 100 ° C. and reacted for 3 hours, and then cooled to 40 ° C. to obtain a prepolymer solution having an isocyanate group. A reaction vessel 2 equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 11.1 parts of methyliminobispropylamine, 6.6 parts of dibutylamine, and 304.6 parts of methoxypropyl acetate and heated to 100 ° C. The said prepolymer solution was dripped there over 30 minutes, and also after reacting for 1 hour, it cooled to room temperature and complete | finished reaction. Methoxypropyl acetate was added thereto to adjust the non-volatile content to 40%, and a comb-shaped dispersant (C2-3) having a number average molecular weight of 20100 was obtained.

(Comb Dispersant (C2-4)) Production Example 10
In a reaction flask equipped with a thermometer, a stirrer, a nitrogen inlet, a reflux pipe and a water separator, 30.0 parts of xylene (made by Junsei Chemical), 300.0 parts of 12-hydroxystearic acid (made by Junsei Chemical) and 0.1 part of tetrabutyl titanate (manufactured by Tokyo Chemical Industry) was charged, and the temperature was raised to 160 ° C. over 4 hours under a nitrogen stream. Further, the mixture was heated at 160 ° C. for 4 hours (the acid value at this time was about 5.0 mg KOH / g), and xylene was distilled off at 160 ° C. In addition, water generated during the heating reaction was separated from xylene in the distillate, and this xylene was returned to the reaction solution. Then it was cooled to room temperature. The polyester contained in this reaction solution had a number average molecular weight of 9,500.
Then, in a reaction flask equipped with a thermometer, a stirrer, a nitrogen inlet, a reflux tube and a water separator, 114.9 parts of xylene and a 10% polyallylamine aqueous solution (“PAA-1LV” manufactured by Nittobo Co., Ltd.) A mixture comprising 70 parts of a number average molecular weight of about 3,000) is stirred at 160 ° C., and water is distilled off using a separator, while xylene is returned to the reaction solution while the polyester 52.7 is added thereto. The part was heated to 160 ° C. and reacted at 160 ° C. for 2 hours to obtain a comb-shaped dispersant (C2-4) having a solid content of 40.1%.

(Comb Dispersant (C2-5)) Production Example 11
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 500 parts of methyl methacrylate, 22 parts of thioglycerol, and 511 parts of methoxypropyl acetate and replaced with nitrogen gas. The inside of the reaction vessel was heated to 90 ° C., and 0.50 part of AIBN was added, followed by reaction for 7 hours. After confirming that 95% had reacted by measuring the nonvolatile content, it was cooled to room temperature to obtain a 50% nonvolatile solution of a vinyl polymer having a weight average molecular weight of 5200 and having two free hydroxyl groups in one end region. Subsequently, 90.4 parts of isophorone diisocyanate, 45.1 parts of methoxypropyl acetate, and 0.11 part of dibutyltin dilaurate as a catalyst were charged and replaced with nitrogen gas. The reaction vessel was heated to 100 ° C. and reacted for 3 hours, and then cooled to 40 ° C. to obtain a prepolymer solution having an isocyanate group. A reaction vessel 2 equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 22.2 parts of methyliminobispropylamine, 13.2 parts of dibutylamine, and 304.6 parts of methoxypropyl acetate and heated to 100 ° C. The said prepolymer solution was dripped there over 30 minutes, and also after reacting for 1 hour, it cooled to room temperature and complete | finished reaction. Methoxypropyl acetate was added thereto to adjust the nonvolatile content to 40%, and a comb-shaped dispersant (C2-5) having a number average molecular weight of 14,000 was obtained.

(Comb-shaped dispersant (C2-6))
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 45.0 parts of methyl methacrylate, 15.0 parts of methacrylic acid, and 40.0 parts of ethyl acrylate, and replaced with nitrogen gas. The inside of the reaction vessel is heated to 80 ° C. and dissolved in 9.6 parts of 3-mercapto-1,2-propanediol and 0.1 part of 2,2′-azobisisobutyronitrile in 45.3 parts of cyclohexanone. The solution was added and reacted for 10 hours. It was confirmed that 95% had reacted by solid content measurement. At this time, the number average molecular weight was 3,500. Next, 24.3 parts of Ricacid BT-100 (manufactured by Nippon Nippon Chemical Co., Ltd.), 69.2 parts of cyclohexanone, and 0.2 part of 1,8-diazabicyclo- [5.4.0] -7-undecene as a catalyst were added. And reacted at 120 ° C. for 7 hours. The reaction was terminated after confirming that 98% or more of the acid anhydride had been half-esterified by measuring the acid value. After the reaction was completed, cyclohexanone was added so that the non-volatile content was 50% by weight to obtain a solution of a comb-shaped dispersant (C2-6) having a number average molecular weight of 10,000.

(Comb-shaped dispersant (C2-7))
A reaction vessel equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 500 parts of methyl methacrylate, 33 parts of thioglycerol, and 511 parts of methoxypropyl acetate and replaced with nitrogen gas. The inside of the reaction vessel was heated to 90 ° C., and 0.50 part of AIBN was added, followed by reaction for 7 hours. After confirming that 95% had reacted by measuring the non-volatile content, it was cooled to room temperature to obtain a 50% non-volatile solution of a vinyl polymer having a weight average molecular weight of 3600 and having two free hydroxyl groups in one end region. Subsequently, 135.6 parts of isophorone diisocyanate, 45.1 parts of methoxypropyl acetate, and 0.11 part of dibutyltin dilaurate as a catalyst were charged and replaced with nitrogen gas. The reaction vessel was heated to 100 ° C. and reacted for 3 hours, and then cooled to 40 ° C. to obtain a prepolymer solution having an isocyanate group. A reaction vessel 2 equipped with a gas introduction tube, a thermometer, a condenser, and a stirrer was charged with 33.3 parts of methyliminobispropylamine, 19.8 parts of dibutylamine, and 304.6 parts of methoxypropyl acetate and heated to 100 ° C. The said prepolymer solution was dripped there over 30 minutes, and also after reacting for 1 hour, it cooled to room temperature and complete | finished reaction. Methoxypropyl acetate was added thereto to adjust the nonvolatile content to 40%, and a comb-shaped dispersant (C2-7) having a number average molecular weight of 11,000 was obtained.

<Example of production of binder resin (D)>
(Binder resin (D-1))
Place 370 parts of propylene glycol monomethyl ether acetate in a reaction vessel and heat to 80 ° C. while injecting nitrogen gas into the vessel. At the same temperature, 12.3 parts of methacrylic acid, 49.2 parts of benzyl methacrylate, paracumylphenol ethylene A mixture of 24.2 parts of oxide-modified acrylate (“Aronix M-110” manufactured by Toagosei Co., Ltd.) and 14.3 parts of 2-hydroxyethyl methacrylate was added dropwise over 1 hour to conduct a polymerization reaction. After completion of the dropwise addition, the mixture was further reacted at 80 ° C. for 3 hours, and then 1.0 part of azobisisobutyronitrile dissolved in 50 parts of propylene glycol monomethyl ether acetate was added, and further reacted at 80 ° C. for 1 hour. Subsequently, an acrylic resin solution was obtained. The weight average molecular weight of the acrylic resin was about 30000. After cooling to room temperature, about 2 g of the resin solution was sampled and heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content. Propylene glycol monomethyl ether was added to the previously synthesized resin solution so that the nonvolatile content was 50% by weight. Acetate was added to prepare a binder resin (D-1) solution.

<Manufacture of finer pigments>
(Fine refined pigment (A-1): PB15: 6)
Copper phthalocyanine blue pigment C.I. I. Pigment Blue 15: 6 (Toyocolor Co., Ltd. “Lionol Blue ES”) 100 parts, pigment derivative (Compound 2) 5 parts, ground sodium chloride 1000 parts, diethylene glycol 100 parts stainless steel 1 gallon kneader (Inoue Seisakusho) And kneaded at 50 ° C. for 12 hours. The mixture was poured into 3000 parts of warm water, stirred at a high speed mixer for about 1 hour while being heated to about 70 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It dried and obtained 98 parts refined pigment (A-1).

(Fine refined pigment (A-2): PR177)
Anthraquinone red pigment C.I. I. 100 parts of Pigment Red 177 (“chromophthaled red A2B” manufactured by BASF), 5 parts of a pigment derivative (Compound 7), 800 parts of crushed salt and 180 parts of diethylene glycol were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho), 70 The mixture was kneaded at 5 ° C. for 5 hours. The mixture was poured into 4000 parts of warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It dried and obtained red refined pigment (A-2).

(Fine refined pigment (A-3): PR254)
Diketopyrrolopyrrole red pigment C.I. I. Pigment Red254 (BASF "Irgafore Red B-CF") 100 parts, pigment derivative (Compound 8) 10 parts, ground sodium chloride 1000 parts, and diethylene glycol 120 parts were charged into a stainless steel 1 gallon kneader (Inoue Seisakusho). And kneading at 70 ° C. for 8 hours. The mixture was added to 2000 parts of warm water, heated to about 80 ° C. and stirred with a high speed mixer for about 1 hour to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It dried and obtained red refined pigment (A-3).

(Fine refined pigment (A-4): PG58)
Green pigment C.I. I. 500 parts of Pigment Green 58 (“First Gain Green A110” manufactured by DIC Corporation), 1500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a 1 gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 120 ° C. for 8 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, a green refined pigment (A-4) was obtained.

(Fine refined pigment (A-5): PY138)
Quinophthalone yellow pigment C.I. I. 100 parts of Pigment Yellow 138 (“Pariotol Yellow K0961HD” manufactured by BASF), 3 parts of a pigment derivative (Compound 3), 800 parts of crushed salt and 180 parts of diethylene glycol were charged in a stainless 1 gallon kneader (manufactured by Inoue Seisakusho). The mixture was kneaded at 4 ° C. for 4 hours. The mixture was added to 3000 parts of warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, filtered and washed repeatedly to remove salt and solvent, and then at 80 ° C. for 24 hours. It dried and obtained 98 parts refined pigment (A-5).

(Fine refined pigment (A-6): PY150)
Metal complex yellow pigment C.I. I. 500 parts of Pigment Yellow 150 (LANXESS "E4GN"), 2500 parts of sodium chloride, and 250 parts of diethylene glycol were charged into a stainless gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 100 ° C for 6 hours. Next, the kneaded product is poured into 5 liters of warm water, stirred for 1 hour while heating to 70 ° C. to form a slurry, filtered and washed repeatedly to remove sodium chloride and diethylene glycol, and then dried at 80 ° C. overnight. As a result, a yellow refined pigment (A-6) was obtained.

<Preparation of Color Filter Coloring Composition (Paste)>
[Example 1]
<Coloring Composition for Color Filter (Paste) (X-1)>
After uniformly stirring and mixing a mixture having the following composition, it was dispersed for 5 hours with an Eiger mill (“Mini Model M-250 MKII” manufactured by Eiger Japan) using zirconia beads having a diameter of 0.5 mm, and then 5.0 μm It filtered with the filter and the coloring composition (paste) (X-1) for color filters was produced.
Pigment A (A-1) 10.0 parts Adsorbent B (R-1) 0.5 parts Dispersant C (C1-1) 3.0 parts Binder resin D (D-1) 16.0 Part / Propylene glycol monomethyl ether acetate 70.5 parts Adsorbent R-1 was used as shown below.

<Adsorbent R-1>
Compound 15

[Examples 2-28, Comparative Examples 1-20]
<Adjustment of coloring composition (paste) for color filter (X-2 to 48)>
Hereinafter, using the materials shown in Table 1, the solid content of the adsorbent (B), the dispersant (C) and the binder resin (D) with respect to the dispersant (A) is the color filter coloring composition (paste) (X -1) and stirring and dispersing in the same manner as the color filter coloring composition (paste) (X-1), and the color filter coloring composition (paste) (X-2 to 48) Got.

  The adsorbent (Q) and adsorbent (R) described in Table 1 are shown below.

<Adsorbent Q-1>
Compound 7

<Adsorbent Q-2>
Compound 3

<Adsorbent Q-3>
Compound 5

<Adsorbent R-2>
Compound 11

<Evaluation of Color Filter Coloring Composition (Paste)>
About the obtained coloring composition (X-1 to 48), the test regarding a viscosity, CR, lightness, and storage stability was done by the following method. The test results are shown in Table 2.

<Measurement of viscosity characteristics>
The viscosity of the green coloring composition for color filters (paste) was measured at a rotation speed of 20 rpm using an E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.). Furthermore, the ratio of the viscosity at the number of revolutions of 6 rpm and 60 rpm (referred to as thixo index, the larger the value, the higher the thixotropic property) was obtained, and the thixotropic property was evaluated.
The rank of evaluation is as follows.
◎: Viscosity 4.0 or more and less than 8.0: Very good level ○: Viscosity 8.0 or more and less than 15.0: Good level Δ: Viscosity 15.0 or more and less than 20.0: Inferior to ○ Practical level ×: Viscosity of 20 or more: Level not suitable for practical use XX: Unevaluable

(Production of color filter and measurement of contrast ratio)
Coating was performed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 0.7 mm using a spin coater at 500 rpm, 1000 rpm, and 1500 rpm to obtain three types of coated substrates having different film thicknesses. The color filter-coated colored composition-coated substrate was dried at 70 ° C. for 20 minutes, heated at 230 ° C. for 1 hour, allowed to cool, and then the contrast ratio was measured. Next, the chromaticity (Y, x, y) of the coating film with a C light source was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). From the three sets of contrast ratio and chromaticity measurement results, the color coating coated substrate for the color filter is y = 0.15 for the blue coating, y = 0.60 for the green coating, and x = for the red coating. The contrast ratio at 0.658 and the contrast ratio at y = 0.440 for the yellow coating film were obtained using an approximation method, respectively.

The rank of evaluation of the contrast ratio is as follows.
(Blue coating)
◎: Contrast 20000 or more: Very good level ○: Contrast 19000 or more and less than 20000: Good level Δ: Contrast 18000 or more and less than 19000: Inferior to ○ but practical level ×: Contrast less than 18000: Unsuitable level for practical use XX: Evaluation not possible (green coating film)
◎: Contrast 18000 or more: Very good level ○: Contrast 17000 or more and less than 18000: Good level Δ: Contrast 16000 or more and less than 17000: Inferior to ○ but practical level ×: Contrast less than 16000: Level not suitable for practical use XX: Evaluation not possible (red coating)
◎: Contrast 15000 or more: Very good level ○: Contrast 14000 or more and less than 15000: Good level Δ: Contrast 13,000 or more and less than 14000: Inferior to ○ but practical level ×: Contrast less than 13000: Unsuitable level for practical use XX: Evaluation not possible (yellow coating film)
◎: Contrast 20000 or more: Very good level ○: Contrast 18000 or more and less than 20000: Good level Δ: Contrast 16000 or more and less than 18000: Inferior to ○ but practical level ×: Contrast 16000 or less: Level not suitable for practical use ××: Evaluation not possible

<Measurement of brightness>
The brightness was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). Regarding the colored composition coating substrate for the color filter, x = 0.14 and y = 0.15 for the blue coating film, x = 0.224 and y = 0.600 for the green coating film, and x = 0.2 for the red coating film. With respect to 0.658, y = 0.325, and the yellow coating film, the lightness at x = 0.440 and y = 0.510 was obtained using an approximation method.
The rank of evaluation is as follows.
(Blue coating)
◎: Brightness 22.5 or more: Very good level ○: Brightness 22.0 or more and less than 22.5: Good level Δ: Brightness 21.0 or more and less than 22.0: Practical level inferior to ○ but ×: Lightness less than 21.0: Level unsuitable for practical use XX: Evaluation not possible (green coating)
◎: Lightness 45.5 or more: Very good level ○: Lightness 45.0 or more and less than 45.5: Good level Δ: Lightness 44.5 or more and less than 45.0: Inferior to ○ but practical level ×: Lightness less than 44.5: Level unsuitable for practical use XX: Unassessable (red coating)
A: Brightness 19.2 or higher: Very good level B: Brightness 19.0 or higher and lower than 19.2: Good level Δ: Brightness 18.8 or higher but lower than 19.0 Lightness less than 18.8: Level not suitable for practical use XX: Evaluation not possible (yellow coating film)
◎: Brightness 92.0 or more: Very good level ○: Lightness 90.0 or more and less than 92.0: Good level Δ: Lightness 88.0 or more and less than 90.0: Practical level that is inferior to ○ but ×: Lightness less than 88.0: Level unsuitable for practical use XX: Evaluation not possible

<Storage stability>
About the coloring composition for color filters (paste) obtained by the Example and the comparative example, the storage stability was evaluated by the following method.
E type viscometer (“ELD type viscometer” manufactured by Toki Sangyo Co., Ltd.) is used to measure the initial viscosity of the color filter color composition (paste) the next day and the time-lapse viscosity accelerated at 40 ° C. for one week. It was measured under the condition of a rotational speed of 50 rpm at 25 ° C. From the values of the initial viscosity and the viscosity with time, the change rate with time was calculated by the following formula, and the storage stability was evaluated in three stages.
[Change in viscosity with time] = | ([initial viscosity] − [viscosity with time]) / [initial viscosity] | × 100
○: Change rate of less than 5% △: Change rate of 5% to 10% ×: Change rate of 10% or more

<Coloring composition for color filter (resist adjustment)>
[Example 29]
(Coloring composition Y-1 for color filter)
A mixture having the following composition was stirred and mixed to be uniform, and then filtered through a 1 μm filter to obtain a colored composition for color filter (Y-1).
-Color filter coloring composition (paste) (X-1) 2.0 parts-Binder resin (D-1) 0.0 parts-Photopolymerizable monomer 5.6 parts (Shin Nakamura Chemical Co., Ltd. "NK" Ester ATMPT ”trimethylolpropane triacrylate)
-Photopolymerization initiator 2.0 parts ("Irgacure 907" 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one manufactured by BASF))
・ Sensitizer 0.2 part (“EAB-F” 4,4′-bis (diethylamino) benzophenone manufactured by Hodogaya Chemical Co., Ltd.)
・ 0.2 parts of propylene glycol monomethyl ether acetate

[Examples 30 to 56, Comparative Examples 21 to 40]
<Coloring composition for color filter (resist) (Y-2 to 48)>
The color filter coloring composition (paste) (Y-2 to 42), the acrylic resin solution, and the solvent were respectively mixed in the same manner as in Example 23, and the corresponding color filter coloring composition (resist) (Y-2). To 48).

<Evaluation of Color Filter Coloring Composition (Resist)>
About the obtained coloring composition for color filters (resist) (Y-1 to 48), tests on viscosity, CR, and brightness were performed in the same manner as the coloring composition for color filters (paste). The results of the evaluation test are shown in Table 3 below.

<Measurement of viscosity characteristics>
The viscosity of the green coloring composition for color filter (resist) was measured at a rotation speed of 20 rpm using an E-type viscometer (“ELD viscometer” manufactured by Toki Sangyo Co., Ltd.). Furthermore, the ratio of the viscosity at the number of revolutions of 6 rpm and 60 rpm (referred to as thixo index, the larger the value, the higher the thixotropic property) was obtained, and the thixotropic property was evaluated.
The rank of evaluation is as follows.
◎: Viscosity 2.8 or more and less than 3.0: Very good level ○: Viscosity 3.2 or more and less than 3.4: Good level Δ: Viscosity 3.4 or more and less than 3.5: Inferior to ○ Practical level ×: Viscosity 3.5 or more: Unsuitable level for practical use XX: Unevaluable

(Production of color filter and measurement of contrast ratio)
Coating was performed on a glass substrate having a size of 100 mm × 100 mm and a thickness of 0.7 mm using a spin coater at 200 rpm, 300 rpm, and 400 rpm to obtain three types of coated substrates having different film thicknesses. The substrate coated with the colored composition for color filter is dried at 70 ° C. for 20 minutes, then exposed to UV light with an integrated light amount of 150 mJ / cm 2 using an ultra-high pressure mercury lamp, heated at 230 ° C. for 1 hour, allowed to cool, and the contrast ratio is set. It was measured. Next, the chromaticity (Y, x, y) of the coating film with a C light source was measured using a microspectrophotometer (“OSP-SP100” manufactured by Olympus Optical Co., Ltd.). From the three sets of contrast ratio and chromaticity measurement results, the color coating colored composition coated substrate is y = 0.15 for the blue coating, y = 0.600 for the green coating, and x = for the red coating. The contrast ratio at 0.658 and the contrast ratio at y = 0.440 for the yellow coating film were obtained using an approximation method, respectively.

The rank of evaluation of the contrast ratio is as follows.
(Blue coating)
◎: Contrast 21000 or more: Very good level ○: Contrast 20000 or more and less than 21000: Good level Δ: Contrast 19000 or more and less than 20000: Inferior to ○ but practical level ×: Contrast less than 19000: Level not suitable for practical use XX: Evaluation not possible (green coating film)
◎: Contrast 19000 or more: Very good level ○: Contrast 18000 or more and less than 19000: Good level Δ: Contrast 17000 or more and less than 18000: Inferior to ○ but practical level ×: Contrast less than 17000: Level not suitable for practical use XX: Evaluation not possible (red coating)
◎: Contrast 16000 or more: Very good level ○: Contrast 15000 or more and less than 16000: Good level Δ: Contrast 14000 or more and less than 15000: Inferior to ○ but practical level ×: Contrast 14000 or less: Level not suitable for practical use XX: Evaluation not possible (yellow coating film)
◎: Contrast 21000 or more: Very good level ○: Contrast 19000 or more and less than 21000: Good level Δ: Contrast 17000 or more and less than 19000: Inferior to ○ but practical level ×: Contrast 17000 or less: Level not suitable for practical use ××: Evaluation not possible

<Measurement of brightness>
Regarding the colored composition coating substrate for the color filter, x = 0.14 and y = 0.15 for the blue coating film, x = 0.224 and y = 0.600 for the green coating film, and x = 0.2 for the red coating film. With respect to 0.658, y = 0.325, and the yellow coating film, the lightness at x = 0.440 and y = 0.510 was obtained using an approximation method.
The rank of evaluation is as follows.
(Blue coating)
A: Brightness 22.3 or higher: Very good level B: Brightness 21.8 or higher and lower than 22.3: Good level Δ: Brightness 20.8 or higher but lower than 21.8 Lightness less than 20.8: Level unsuitable for practical use XX: Evaluation not possible (green coating)
A: Brightness 45.3 or higher: Very good level O: Brightness 44.8 or higher and lower than 45.3: Good level Δ: Brightness 44.3 or higher but lower than 44.8: Practical level but inferior to ○ ×: Lightness less than 44.3: Level unsuitable for practical use XX: Unassessable (red coating)
◎: Lightness 19.1 or more: Very good level ○: Lightness 18.9 or more, but less than 19.1: Good level Δ: Lightness 18.7 or more, but less than 18.9: Practical level that is inferior to ○ but ×: Lightness less than 18.7: Level unsuitable for practical use XX: Unevaluable (yellow coating film)
A: Brightness 91.0. Above: Very good level ○: Lightness 89.0 or more and less than 91.0: Good level Δ: Lightness 87.0 or more and less than 89.0: Practical level inferior to ○ but lightness: Less than 87.0: Level not suitable for practical use XX: Evaluation not possible

<Storage stability>
About the coloring composition (resist) for color filters obtained by the Example and the comparative example, the storage stability was evaluated by the following method.
E type viscometer ("ELD type viscometer" manufactured by Toki Sangyo Co., Ltd.) is used to measure the initial viscosity of the color filter color composition (resist) the next day and the time-lapse viscosity accelerated at 40 ° C for one week. It was measured under the condition of a rotational speed of 50 rpm at 25 ° C. From the values of the initial viscosity and the viscosity with time, the change rate with time was calculated by the following formula, and the storage stability was evaluated in three stages.
[Change in viscosity with time] = | ([initial viscosity] − [viscosity with time]) / [initial viscosity] | × 100
○: Change rate of less than 5% △: Change rate of 5% to 10% ×: Change rate of 10% or more

  As shown in Table 3, the colored composition for a color filter of the present invention was able to achieve high brightness while maintaining the initial viscosity and storage stability as compared with the colored composition shown in the comparative example.

Claims (8)

A coloring composition for a color filter having a pigment (A), an adsorbent (B) having a pigment adsorbing group, and a dispersant (C),
The adsorbent (B) is 8 parts by weight or less with respect to 100 parts by weight of the pigment (A),
Dispersant (C) is a linear dispersant (C1) having a site (x) that forms a salt with a pigment adsorbing group at one end and having a number average molecular weight of 5000 or more.
And / or
A coloring composition for a color filter, which is a comb-shaped dispersant (C2) having a moiety (x) that forms a salt with a pigment adsorbing group in the main chain and having a side chain number average molecular weight of 5000 or more. object.   The coloring composition for a color filter according to claim 1, wherein the pigment adsorbing group has a basic group, and the site (x) that forms a salt with the pigment adsorbing group has an acidic group.   The adsorbent (B) having a pigment adsorbing group is composed of a pigment derivative having a basic group, an anthraquinone derivative having a basic substituent, a triazine derivative having a basic substituent, and an acridone derivative having a basic substituent. 3. The color filter according to claim 1, comprising a pigment derivative (Q) having at least one basic substituent selected from: and / or a vinyl resin (S) having a basic group. Coloring composition.   The coloring composition for a color filter according to claim 3, wherein the vinyl resin (S) having a basic group has a tertiary amino group and an amine value of 50 to 500 mgKOH / g.   The dispersant (C) is a fragrance obtained by reacting a polymer (X) having a hydroxyl group at one end with an aromatic tricarboxylic acid anhydride (Y1) and / or an aromatic tetracarboxylic dianhydride (Y2). The coloring composition for a color filter according to any one of claims 1 to 4, which is a dispersant having a group carboxyl group.   The pigment (A) is C.I. I. Pigment green 58 and / or C.I. I. The coloring composition for a color filter according to claim 1, which is CI Pigment Yellow 150.   Furthermore, the coloring composition for color filters in any one of Claims 1-6 containing a photopolymerizable monomer and / or a photoinitiator.   A color filter comprising a filter segment formed on the substrate from the colored composition for color filter according to claim 1.