JP2003081972A - Triazine, pigment dispersant, pigment dispersant composition containing the same and optical coloration- sensitive composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a colorless triazine and a colorless and stable pigment dispersant having excellent pigment dispersibility and fluidity, and has excellent transparency. SOLUTION: The triazine is represented by following formula (1) or (2) [wherein R<1> is a halogen, hydroxyl, amino, alkoxy, alkylamino, dialkylamino, a heterocyclic group; -X<3> -Ar (wherein Ar is a hydrocarbon aromatic ring, a heteroatom-including aromatic ring); X<1> -X<3> are each O, N(R<2> ) (where R<2> is H, an alkyl, an alkenyl, an alkynyl); R<3> -R<5> are each H, a halogen, amino, an alkoxy, an alkyl, an alkenyl, an alkynyl, an aryl, an alkylthio, amide and ester].

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a triazine compound, a pigment dispersant using the same, a paint, a printing ink,
Suitable for pigment dispersion compositions suitable for a wide range of fields such as color display plates (color filters), for forming multicolor images on substrates such as color proofs, and for manufacturing color filters used for liquid crystal color displays, etc. More specifically, the present invention relates to a novel triazine compound having no azo dye skeleton, an uncolored pigment dispersant containing the triazine compound, a pigment dispersion composition, and a colored photosensitive composition.

[0002]

2. Description of the Related Art Conventionally, pigments have a vivid color tone and high tinting strength and have been widely used in many fields.
Many of these pigments which are practically important are generally fine particles, and a clear color tone and a high tinting strength can be obtained by preventing aggregation of the pigment and making it fine. However, as the pigment is made finer, the dispersion liquid of the pigment often exhibits high viscosity. Therefore, when this pigment dispersion is prepared on an industrial scale, it becomes difficult to take out the pigment dispersion from the disperser, it cannot be transported by a pipeline, and further, gelation occurs during storage. There are problems such as being unusable.

By the way, a colored photosensitive composition containing the above-mentioned pigment is useful as a material for a color filter used in a liquid crystal display or the like. When a colored filter is produced using the colored photosensitive composition, the quality, A pigment dispersion method, which is excellent in terms of production stability, is widely adopted. In this pigment dispersion method, a coating solution of the colored photosensitive composition is applied onto a transparent substrate to provide a colored photosensitive layer, and after pattern exposure, development is performed to form a pixel pattern of the first color,
This is repeated a plurality of times to form pixel patterns of a plurality of colors on the transparent substrate.

However, since a pigment is used as a coloring material here, if the pigment is not sufficiently miniaturized or dispersed, light is scattered and absorbed by the pigment and the light transmittance is lowered, or Further, there is a problem that the polarization axis is rotated due to light scattering and birefringence due to the pigment, and the contrast of the liquid crystal display device is lowered (1990 7th color optical conference, 512 color display 10. 4 "size TFT-LCD color filter, Ueki, Ozeki, Fukunaga, Yamanaka). Therefore, in the colored photosensitive composition, it is necessary to disperse the pigment in a highly finely divided state. It

The colored photosensitive composition containing a pigment exhibiting a clear color tone and high tinting strength is also useful as an image forming material for producing a color proof, a color filter or the like. Also when a colored image is formed using the colored photosensitive composition, generally, a coating solution of the colored photosensitive composition is applied onto a substrate to form a layer, and then exposure and development are carried out. As a developing solution, an alkaline aqueous solution that has little influence on the environment is often used, and the layer (that is, the binder in the colored photosensitive composition) is soluble in the alkaline aqueous solution. Required. On the other hand, as the solvent (dispersion medium of the pigment) used for the coating liquid of the colored photosensitive composition, an organic solvent is effective because of easy drying after coating. Therefore, the binder in the colored photosensitive composition preferably has an acidic group and has a property of being soluble in an appropriate organic solvent. In the colored photosensitive composition, the pigment is Dispersed in a binder having acidic groups and having the above properties.

Therefore, it is known to use various dispersants in order to obtain a pigment dispersion (composition) or a colored photosensitive composition having excellent fluidity and dispersibility. This dispersant is roughly classified into a polymer dispersant and a low molecular compound dispersant. As the polymer-based dispersant, polyacrylate, sodium maleate olefin copolymer,
Polyester containing terminal carboxyl group (Japanese Patent Publication No. 54-3
4009), a polyester having an acidic group and / or a basic group starting from tetrakis (2-hydroxyalkyl) ethylenediamine (JP-A-2-2452).
31), macromonomers (oligomers having ethylenically unsaturated groups at the ends), monomers having hydroxyl groups,
A copolymer composed of four kinds of a carboxy group-containing monomer and a monomer other than these (Japanese Patent Application Laid-Open No. 8-259876) is known. Further, as the low molecular compound dispersant, sorbitan fatty acid ester, polyoxyethylene alkylamine, alkyldiamine, alkanolamine derivative (US Pat. No. 3,536,510) and the like are known. The example is also special fair 5
-72943 and JP-A-8-48890.

However, most of the conventionally used dispersants have coloring themselves, such as the dispersant in which the pigment mother nucleus is introduced, and therefore, they are used as color filters or image forming materials. In some cases, the coloring has been adjusted and used within a practically usable range by further adding a desired hue. However,
Image characteristics required for color images in recent years are high, and in particular, for color filters, further improvement in color purity of R (red), G (green), and B (blue) has been required.

Under these circumstances, colorless pigment dispersants have been proposed, for example, JP-A-11-199796.
No. 10-46043 and No. 9-31351.
JP-A No. 9-272811 and the like disclose a dispersant which is itself colorless. However, in a system in which the pigment is ultrafinely divided and dispersed in order to obtain the high light transmittance required for recent color filter applications, the viscosity of the dispersion liquid increases with time when left at room temperature or under heating, and the stability is stable. However, there was a problem in terms of dispersion stability. Further, JP-A-8-48890 and JP-A-10-48890
No. 2,656,971 discloses a dispersant which itself can be colorless. In any of them, however, in a system in which the pigment is micronized and dispersed as described above, the dispersion stability with time is not sufficient and the viscosity increases. It was difficult to obtain a dispersion free from.

Further, in the case of forming a layer using a colored photosensitive composition containing a pigment, it is generally required that the layer can be formed in an extremely thin layer and that a high coloring density is exhibited. Even in this respect, as described above, even in a binder soluble in an organic solvent and having an acidic group, it is necessary to stably disperse the pigment in a highly finely divided state without aggregating. It

[0010]

However, even in a system for obtaining high light transmittance by dispersing a pigment in the form of ultrafine particles such as a color filter application, the pigment is particularly excellent in dispersibility, fluidity, and the like. The subsequent dispersion stability is good, and a general-purpose non-colored pigment dispersion which does not impair the hue of the pigment in practice and does not depend on the pigment species, and a pigment dispersion composition and a colored photosensitive composition containing the same are The current situation is that it has not been provided yet. Therefore, it is an object of the present invention to solve the above-mentioned conventional problems and achieve the following objects. That is,

The present invention aims to provide novel triazine compounds which are substantially colorless. Further, the present invention provides a pigment dispersant which is substantially colorless, does not cause pigment aggregation, realizes stable and good dispersibility and fluidity of the pigment, and is also excellent in light transmittance. Contains a pigment dispersant, and has excellent pigment dispersibility, fluidity, and coloring concentration.
Moreover, it provides a pigment dispersion composition suitable for a wide range of paints, printing inks, color display panels, etc., which is particularly excellent in hue purity, colored hue and light transmittance without impairing the hue of pigments and has alkali developability. In addition, the composition contains the pigment dispersion composition and is particularly excellent in not only the coloring concentration but also the hue purity and the coloring hue and the light transmittance, and has the alkali development suitability to form a multicolor image such as a color proof or a color. An object of the present invention is to provide a colored photosensitive composition suitable for manufacturing filters and the like.

[0012]

Means for Solving the Problems As a result of repeated studies on a dispersant for dispersing a pigment, the present inventors have obtained the following findings. That is, when an organic pigment is dispersed in a binder having an acidic group, the viscosity tends to increase due to the intermolecular force between the acidic group and the organic pigment. Particularly in a system such as a color filter which needs to obtain a high light transmittance, it is necessary to disperse the pigment in the form of ultrafine particles, but the viscosity in this case tends to further increase. Further, in order to use the coloring hue of the pigment as it is, it is inevitable that the dispersant itself is not colored. Based on the above findings, the concrete means for achieving the above-mentioned problems are as follows.

<1> A triazine compound represented by the following general formula (1) or (2).

[0014]

[Chemical 2]

[In the general formulas (1) and (2), R ¹ is a halogen atom, a hydroxyl group, an amino group, an alkoxy group, an alkylamino group, a dialkylamino group, a heterocyclic group, or -X ³
Represents an -Ar group, Ar represents a hydrocarbon aromatic ring or a hetero atom-containing aromatic ring, and may be a condensed ring. X ¹ , X ² and X ³ each independently represent —O—, —N (R ² ) —,
R ² may be the same or different, and R ² represents a hydrogen atom, an alkyl group, an alkenyl group, an alkynyl group or an aryl group. In the general formula (1), R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a halogen atom, an amino group, an alkoxy group, an alkyl group, an alkenyl group, an alkynyl group,
It represents an aryl group, an alkylthio group, an amide group, or an ester group, which may be the same or different. ]

<2> A pigment dispersant containing the triazine compound described in <1> above. <3> Molar extinction coefficient at wavelength 400 nm or more is 100
The pigment dispersant according to <2>, which is less than 0. <4> The pigment dispersant according to <2> or <3>,
A pigment dispersion composition comprising a pigment and an organic solvent dispersed therein. <5> The pigment dispersion composition according to <4>, which contains a binder polymer having an acidic group. <6> Containing the pigment dispersion composition according to <4>, a binder polymer having an acidic group, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. And a colored photosensitive composition.

[0017]

DETAILED DESCRIPTION OF THE INVENTION Each of the present invention will be described in detail below. <Triazine Compound> The triazine compound of the present invention is a substantially colorless compound that can disperse a pigment in fine particles and uniformly without impairing fluidity, and functions as a dispersant having good dispersion stability. Is a compound to be obtained. In the present invention, “substantially colorless” means coloring that reduces the color purity of hue (BGR, etc.), that is, no absorption in the visible range and excellent light transmittance, specifically, a wavelength of 400 nm or more. It means that the substance does not have absorption with an extinction coefficient of 1000 or more (the same applies in this specification). Specifically, it is represented by the following general formula (1) or (2).

[0018]

[Chemical 3]

R ¹ in the general formulas (1) and (2) is
Halogen atom, hydroxyl group, amino group, alkoxy group, alkylamino group, dialkylamino group, heterocyclic group, -X
Represents a ^3- Ar group. Preferable examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

The alkoxy group is preferably an alkoxy group having 1 to 20 carbon atoms, more preferably an alkoxy group having 1 to 10 carbon atoms, and it may be unsubstituted or substituted. When substituted, examples of the substituent include a methoxy group, an ethoxy group, a butoxy group, a chloro group, a bromo group, an amino group, a dimethylamino group, a diethylamino group, a methylthio group, and the like. As the alkoxy group,
For example, methoxy group, ethoxy group, propoxy group, isopropoxy group, n-butoxy group, sec-butoxy group,
t-butoxy group, isobutoxy group, amyloxy group, cyclopentyloxy group, isoamyloxy group, sec-
Amyloxy group, t-amyloxy group, hexyloxy group, cyclohexyloxy group, octyloxy group, 2-
Ethylhexyloxy group, nonyloxy group, 3,5,5
-Trimethylhexyloxy group, decyloxy group, undecyloxy group, hexadecyloxy group, octadecyloxy group, methoxymethyloxy group, 2-methoxyethyloxy group, 2- (2'-methoxyethoxy) ethyloxy group, 2-acetyl Examples thereof include an ethyloxy group, a 2-phenoxyethyloxy group, a 2- (2 ', 4'-t-amylphenyloxy) butyloxy group, a 2-methylthioethyloxy group and a diethylaminopropyloxy group.

The alkylamino group is preferably one whose alkyl moiety has 1 to 20 carbon atoms, and may be unsubstituted or substituted. When substituted, examples of the substituent include a methoxy group, an ethoxy group, a dimethylamino group, a phenyl group, a dibutylaminocarbonyl group, and the like. For example, methylamino group, ethylamino group, propylamino group, butylamino group, hexylamino group, octylamino group, dodecylamino group, 2
-Methoxyethylamino group, 3-phenylpropylamino group, (dibutylaminocarbonyl) methylamino group and the like.

The dialkylamino group preferably has an alkyl moiety having 1 to 20 carbon atoms, and may be unsubstituted or substituted. When substituted, examples of the substituent include a hydroxyl group, a methoxy group, a hexyloxy group, a diethylamino group, a phenyl group, and the like. For example, a dimethylamino group, a diethylamino group,
Dipropylamino group, dibutylamino group, diamylamino group, dihexylamino group, diheptylamino group, dioctylamino group, dinonylamino group, dihexadecylamino group, N-methyl-N-octylamino group, N-methyl-N- Octadecylamino group, N-ethyl-N-butylamino group, N-methyl-N- (hydroxyethyl) amino group, N-methyl-N-phenethylamino group and the like can be mentioned.

The heterocyclic group may be unsubstituted or substituted, and examples thereof include a pyrrolidino group, a piperidino group and a morpholino group. When substituted, examples of the substituent include a methyl group, a propyl group, a methoxy group, an ethoxy group, and the like. -X ^3-
In the Ar group, Ar may be unsubstituted or substituted, represents a hydrocarbon aromatic ring or a hetero atom-containing aromatic ring, and may be a condensed ring. Incidentally, X ³ is as described later. When substituted, examples of the substituent include an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an amino group, an alkylamino group, a dialkylamino group, an ester, an amide, a urea and a urethane.

Examples of the hydrocarbon-based aromatic ring include:
Benzene, naphthalene, anthracene, methoxybenzene, dichlorobenzene, dimethylaminobenzene, m-
Methoxydimethylaminobenzene and the like, as the hetero atom-containing aromatic ring, pyridine, pyrrole, thiophene, furan, pyrazole, imidazole, thiazole,
Examples thereof include oxazole, pyrimidine, oxazine, quinoline, indole, isoindole, benzofuran, benzpyrazole, benzimidazole, benzthiazole, benzoxazole, benzimidazolone and triazine.

Among the above Ar, benzene, dichlorobenzene, dimethylaminobenzene, m-methoxydimethylaminobenzene, pyridine, pyrrole, pyrazole,
Particularly preferred are imidazole, thiazole, oxazole, pyrimidine, oxazine, quinoline, indole, isoindole, benzfuran, benzpyrazole, benzimidazole, benzthiazole, benzoxazole, benzimidazolone and triazine. In addition, specific examples of the —X ³ —Ar group include a phenoxy group, a phenylamino group, a 4-diethylaminophenylamino group,
4- (3'-diethylamino) propylaminocarbonylphenyloxy group, 3,5-bis (2'-dimethylamino) ethylaminocarbonylphenylamino group and the like are preferable.

Among the above R ¹ , chlorine atom, hydroxyl group, amino group, methoxy group, ethoxy group, butoxy group, hexyloxy group, cyclohexyloxy group, 3,5,5-trimethylhexyloxy group, decyloxy group, octadecyloxy group. Group, methoxymethyloxy group, 2-methoxyethyloxy group, 2-acetylethyloxy group, 2-phenoxyethyloxy group, 2- (2 ', 4'-t-amylphenyloxy) butyloxy group, methylamino group,
Ethylamino group, butylamino group, octylamino group,
Dodecylamino group, 2-methoxyethylamino group, (dibutylaminocarbonyl) methylamino group, dimethylamino group, diethylamino group, dipropylamino group, dibutylamino group, dihexylamino group, dioctylamino group, N-methyl-N- octadecyl amino group, pyrrolidino group, piperidino group, morpholino group, and -X ³ -Ar
Groups are particularly preferred. Among the -X ³ -Ar group, phenylamino group, 3,5-bis (2'-dimethylamino) ethylaminocarbonyl phenylamino group are particularly preferred.

In the general formulas (1) and (2), X
¹ , X ² and X ³ are each independently —O—, —N (R ² ) —
And may be the same or different from each other, and R ² is
Hydrogen atom, alkyl group, alkenyl group, alkynyl group,
It represents an aryl group, and each group except a hydrogen atom may be unsubstituted or substituted. When the substituent is substituted, a methoxy group, an ethoxy group, a chloro group, a bromo group,
Etc.

The (substituted) alkyl group represented by R ² is preferably an alkyl group having 1 to 20 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, a hexyl group, an octyl group and an undecyl group. Group, heptadecyl group,
Preferable examples thereof include a methoxymethyl group, a 2-methoxyethyl group, a dimethylaminoethyl group, and the like, and the (substituted) alkenyl group represented by R ² is preferably an alkenyl group having 2 to 20 carbon atoms, for example, vinyl. Group, 2-propenyl group, 3-hexenyl group, 7-octenyl group, and the like, and the (substituted) alkynyl group represented by R ² is preferably an alkynyl group having 2 to 20 carbon atoms, for example, Propargyl group, 3-butynyl group, and the like,
The (substituted) aryl group represented by R ² is preferably an aryl group having a carbon number of 6 to 20, and examples thereof include a phenyl group, a 3-methoxyphenyl group, a 3,4-dichlorophenyl group, a benzyl group and a phenethyl group. Is mentioned. Among the above R ² , hydrogen atom, methyl group, ethyl group, butyl group, hexyl group, phenyl group and benzyl group are particularly preferable.

R ³ , R ⁴ and R in the general formula (1)
⁵ independently represent a hydrogen atom, a halogen atom, an amino group, an alkoxy group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an alkylthio group, an amide group, an ester group, which may be the same or different from each other, Each group except a hydrogen atom and a halogen atom may be unsubstituted or substituted. The substituent here is a methyl group,
Examples thereof include a methoxy group, a chloro group, a diethylamino group, a phenyl group and a diethylamino group. The above R ^{3 to} R ⁵
The halogen atom represented by is as defined for R ¹ .

The alkoxy group represented by R ^{3 to} R ⁵ is preferably an alkoxy group having 1 to 20 carbon atoms, for example, methoxy group, ethoxy group, butoxy group, hexyloxy group, octyloxy group, 2- Preferable examples are ethylhexyloxy group, nonyloxy group, 2-methoxyethoxy group and the like. The alkyl group represented by R ^{3 to} R ⁵ is preferably an alkyl group having 1 to 20 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, a butyl group, an amyl group, a hexyl group, a heptyl group, and an octyl group. Preferable examples include a group, a 2-ethylhexyl group, a 3,5,5-trimethylhexyl group, a decyl group, a dodecyl group, a pentadecyl group, a 2-methoxyethyl group and a dimethylaminoethyl group.

The alkenyl group represented by R ^{3 to} R ⁵ is preferably an alkenyl group having a carbon number of 2 to 20, and examples thereof include a vinyl group, an allyl group, a 3-hexenyl group, a 7-octenyl group and a 9-decenyl group. Group, etc. are mentioned suitably. The alkynyl group represented by R ^{3 to} R ⁵ has 2 carbon atoms.
The alkynyl group of 20 to 20 is preferable, and suitable examples include a propargyl group, a 3-butynyl group, a 5-hexynyl group, and a 6-heptynyl group. The aryl group represented by R ^{3 to} R ⁵ is preferably an aryl group having a carbon number of 6 to 20, and examples thereof include a phenyl group, a naphthyl group, a 3-methoxyphenyl group, a 3,4-dichlorophenyl group, and 4-dimethyl. Preferable examples are aminophenyl group, benzyl group, crotyl group, cinnamyl group, phenethyl group and the like.

The alkylthio group represented by R ^{3 to} R ⁵ is preferably an alkylthio group having 1 to 20 carbon atoms,
For example, methylthio group, ethylthio group, butylthio group,
A hexylthio group, a 2-ethylhexylthio group, and the like are preferable. Examples of the amide group represented by R ^{3 to} R ⁵ include dimethylamino group, ethylamino group, diethylamino group, butylamino group, N-methyl-N-octylamino group, 3-diethylaminopropylamino group,
A 2-dimethylaminoethylamino group and the like are preferable.

Examples of the ester group represented by R ^{3 to} R ⁵ include methoxycarbonyl group, ethoxycarbonyl group, hexyloxycarbonyl group, butoxysulfonyl group, 3-dimethylaminopropyloxycarbonyl group, 2-diethylaminoethyl. Oxysulfonyl group, methylaminocarbonyl group, butylaminocarbonyl group,
3-dimethylaminopropylaminocarbonyl group, 3-
A diethylaminopropylaminocarbonyl group, a 3-diethylaminopropylaminosulfonyl group, a 2-dimethylaminoethylaminosulfonyl group, a 6-dimethylaminohexyloxysulfonyl group and the like are preferable.

Among the above, as R ³ , R ⁴ or R ⁵ , hydrogen atom, chlorine atom, bromine atom, methyl group, ethyl group, amyl group, heptyl group, octyl group, 2-ethylhexyl group, 3,5 , 5-trimethylhexyl group, pentadecyl group, 2-methoxyethyl group, methoxy group, ethoxy group, butoxy group, hexyloxy group, 2-methoxyethoxy group, dimethylamino group, ethylamino group, diethylamino group, N-methyl- N-octylamino group, 3-
Diethylaminopropylamino group, phenyl group, 3-methoxyphenyl group, 4-dimethylaminophenyl group, benzyl group, cinnamyl group, methoxycarbonyl group, hexyloxycarbonyl group, butoxysulfonyl group, 3-
Dimethylaminopropyloxycarbonyl group, butylaminocarbonyl group, 3-dimethylaminopropylaminocarbonyl group, 3-diethylaminopropylaminocarbonyl group, 2-dimethylaminoethylsulfonyl group, 6
The -dimethylaminohexyloxysulfonyl group is particularly preferred.

Specific examples of the triazine compounds represented by the general formula (1) or (2) (exemplary compounds (1) to
(28)) is shown. However, the present invention is not limited to these. "Me" in the exemplified compounds
Is the "CH _3", the "Et", "C ₂ H _5", the "Bu""C ₄ H _9" each represents.

[0036]

[Chemical 4]

[0037]

[Chemical 5]

[0038]

[Chemical 6]

[0039]

[Chemical 7]

[0040]

[Chemical 8]

The synthesis of the triazine compound of the present invention is not particularly limited, and generally, it can be suitably carried out by a method of causing a nucleophilic agent to act on cyanuric chloride stepwise. For example, as a specific method of the exemplified compounds (4) and (7), it can be carried out as shown in the following examples.
Also, other exemplified compounds can be synthesized according to these methods.

<Pigment Dispersant> The pigment dispersant of the present invention comprises a substantially colorless triazine compound represented by the above general formula (1) or (2), and is appropriately added as necessary. It may contain other selected ingredients. —Triazine Compound— The triazine compound is as described above, and the content of the triazine compound in the pigment dispersant is preferably at least 50% by mass or more. If the content is less than 50% by mass, the dispersibility of the pigment and the dispersion stability after dispersion may be insufficient, and the fluidity of the resulting pigment dispersion may be reduced.

-Other Components- The pigment dispersant of the present invention may contain only one or more of the triazine compounds represented by the above general formula (1) or (2), and if necessary ,. You may further contain the other component selected suitably. Examples of the other components include known dispersants, and specifically, nonanoamide, decane amide, dodecane amide, N-dodecyl hexadecane amide, N-octadecyl propioamide, N, N-
Amide compounds such as dimethyldodecane amide and N, N-dihexylacetamide, diethylamine, diheptylamine, dibutylhexadecylamine, N, N, N ′,
N'-tetramethylmethanamine, triethylamine,
Amine compounds such as tributylamine and trioctylamine, monoethanolamine, diethanolamine, triethanolamine, N, N, N ′, N ′-(tetrahydroxyethyl) -1,2-diaminoethane, N, N,
N'-tri (hydroxyethyl) -1,2-diaminoethane, N, N, N ', N'-tetra (hydroxyethylpolyoxyethylene) -1,2-diaminoethane, 1,
4-bis (2-hydroxyethyl) piperazine and 1-
Examples thereof include amines having a hydroxy group such as (2-hydroxyethyl) piperadisi, and compounds such as pecotamide, isonipecotamide, and nicotinic acid amide. These may be commercially available products or those synthesized as appropriate, and examples of the commercially available products include Shigenox-105 (trade name, manufactured by Hakkol Chemical Co.).

The content of the other components in the pigment dispersant is preferably 0 to 90% by mass, and 0 to 70% by mass.
Is more preferable. When the content exceeds 90% by mass, the performance as a pigment dispersant may not be sufficiently exhibited.

The pigment dispersant of the present invention may further contain an amine compound represented by the following general formula (I) or (II).

General formula (I)

[Chemical 9]

In the above general formula (I), R ³¹ and R ³²
Each independently represent a hydrogen atom, or an alkyl group or aralkyl group which may have a substituent, and these may be bonded to each other to form a 5-membered to 6-membered saturated ring containing a nitrogen atom. . The saturated ring may further contain 1 to 3 atoms selected from oxygen atom, sulfur atom and nitrogen atom. R ³³ represents an alkylene group or an alkylene group containing an ether bond. X ³ is -CON (Y ³¹ ).
(Y ³² ), -OCON (Y ³¹ ) (Y ³² ), -N (Y ³³ ) CO (Y
^34), or an ^{-N (Y 33) CON (Y} 31) (Y 32).
Y ³¹ , Y ³² , Y ³³ and Y ³⁴ each independently represent a hydrogen atom or an alkyl group, aralkyl group or aryl group which may have a substituent.

General formula (II)

[Chemical 10]

In the general formula (II), R ⁴¹ , R ⁴² ,
R ⁴⁶ and R ⁴⁷ each independently represent a hydrogen atom, or an optionally substituted alkyl group or aralkyl group, which are bonded to each other to form a 5-membered to 6-membered saturated ring containing a nitrogen atom. You may form. The saturated ring may further contain 1 to 3 atoms selected from oxygen atom, sulfur atom and nitrogen atom. R ⁴⁴ and R ⁴⁵ each independently represent an alkylene group or an alkylene group having an ether bond. Z ^{4 is, -CON (Y 41) -,} - OCON (Y 41)
- or ^{-N (Y 42) CON (Y} 43) -, it represents a. Y ⁴¹ , Y ⁴²
And Y ⁴³ are synonymous with Y ³¹ , Y ^32, and Y ³³ in the above general formula (I) in this order.

Specific examples of the amine compound represented by the general formula (I) or (II) include bis (2- (1-morpholino) ethyl) terephthalamide and the like.

Further, the pigment dispersant of the present invention may contain various surfactants, and the presence of the surfactant is effective for improving dispersion stability. Examples of the surfactant include an alkylnaphthalene sulfonate, an anionic surfactant represented by a phosphoric acid ester salt, a cationic surfactant represented by an amine salt, an aminocarboxylic acid, and a betaine type. Examples include amphoteric surfactants.

The dispersion of the pigment by the pigment dispersant of the present invention is
It is preferable to carry out in a state in which particles that can be effectively achieved by directly mixing the pigment dispersant and the pigment and that can be dispersed other than the pigment are not present as much as possible. When the pigment is dispersed in such a state, the pigment dispersant of the present invention is instantly adsorbed around the pigment particles, the pigment particles are well dispersed and flow well, and the pigment particles are aggregated. Is effectively suppressed.
On the other hand, when the pigment is dispersed in the presence of particles that can be dispersed in addition to the pigment particles, the pigment dispersant of the present invention is not adsorbed on the surface of the intended pigment particles, but adsorbed on the surface of other particles, The pigment dispersion effect of the pigment dispersant may be impaired. Therefore, for example, in the case of producing a light-sensitive material or the like, in order to allow the pigment to be dispersed in the light-sensitive material in a well-dispersed state, the pigment and the pigment dispersant of the present invention are mixed at an early stage. Before or during dispersion, it is preferable to add a binder polymer having an acidic group, and it is preferable to add and mix the pigment dispersant of the present invention at a late time such as when preparing a coating liquid for a photosensitive layer. Absent.

The pigment dispersant of the present invention realizes good dispersibility in which the pigment can be uniformly and finely dispersed, and dispersion stability which does not cause aggregation of the pigment due to storage over time, and is substantially colorless and essentially pigment-free. It is possible to obtain a pigment dispersion which does not impair the hue and which is excellent in light transmittance and has good fluidity. Therefore, it can be suitably used for dispersing known pigments, and can be particularly suitably used for the pigment dispersion composition and the colored photosensitive composition of the present invention described later.

<Pigment Dispersion Composition> The pigment dispersion composition of the present invention is obtained by dispersing the above-described pigment dispersant of the present invention and a pigment in an organic solvent, and preferably a binder having an acidic group. Dispersed with the polymer.

—Pigment Dispersant— The pigment dispersant is as described above, and the preferred embodiments are also the same. The content of the pigment dispersant in the pigment dispersion composition is usually 0.1 to 100 parts by mass, and preferably 1 to 30 parts by mass with respect to 100 parts by mass of the pigment. When the content is less than 0.1 parts by mass,
The viscosity of the pigment dispersion composition may increase, and when it exceeds 100 parts by mass, when producing a color filter or the like,
It may be difficult to adjust the hue.

-Pigment- Examples of the pigment include organic pigments. Examples of the organic pigments include yellow pigments, orange pigments, red pigments, violet pigments, blue pigments, green pigments, brown pigments, black pigments, and the like.

Examples of the yellow pigment include C.I. I.
Pigment Yellow 20, C.I. I. Pigment Yellow 24, C.I. I. Pigment Yellow 12, C.I. I pigment yellow 17, C.I. I. Pigment Yellow 83,
C. I. Pigment Yellow 86, C.I. I. Pigment Yellow 93, C.I. I. Pigment Yellow 109,
C. I. Pigment Yellow 110, C.I. I. Pigment Yellow 117, C.I. I. Pigment Yellow 12
5, C.I. I. Pigment Yellow 137, C.I. I. Pigment Yellow 138, C.I. I. Pigment Yellow 1
39, C.I. I. Pigment Yellow 185, C.I. I. Pigment Yellow 147, C.I. I. Pigment Yellow 148, C.I. I pigment yellow 153, C.I. I. Pigment Yellow, C.I. I. Pigment Yellow 15
4, C.I. I. Pigment Yellow 166, C.I. I. Pigment Yellow 168, C.I. I. Pigment Yellow 1
85 and the like.

Examples of the orange pigment include C.I.
I. Pigment Orange 36, C.I. I. Pigment Orange 43, C.I. I. Pigment Orange 51, C.I. I.
Pigment Orange 55, C.I. I. Pigment Orange 59, C.I. I. Pigment Orange 61, C.I. I. Pigment Orange 71, and the like.

Examples of the red pigment include C.I. I.
Pigment Red 9, C.I. I. Pigment Red 97,
C. I. Pigment Red 122, C.I. I. Pigment Red 123, C.I. I. Pigment Red 149, C.I.
I. Pigment Red 168, C.I. I. Pigment Red 177, C.I. I. Pigment Red 180, C.I. I.
Pigment Red 192, C.I. I. Pigment Red 2
15, C.I. I. Pigment Red 216, C.I. I. Pigment Red 217, C.I. I. Pigment Red 22
0, C.I. I. Pigment Red 223, C.I. I. Pigment Red 224, C.I. I. Pigment Red 226,
C. I. Pigment Red 227, C.I. I. Pigment Red 228, C.I. I. Pigment Red 240, C.I.
I. Pigment Red 48: 1, C.I. I. Pigment Red 209, C.I. I. Pigment Red 146, C.I.
I. Pigment Red 11, C.I. I. Pigment Red 81, C.I. I. Pigment Red 213, C.I. I. Pigment Red 272, C.I. I. Pigment Red 27
0, C.I. I. Pigment Red 255, C.I. I. Pigment Red 264, C.I. I. Pigment Red 254,
Etc.

As the violet pigment, for example,
C. I. Pigment violet 19, C.I. I. Pigment Violet 23, C.I. I. Pigment Violet 29, C.I. I. Pigment Violet 30, C.I.
I. Pigment Violet 37, C.I. I. PIMEND violet 40, C.I. I. Pigment Violet 5
0, etc.

Examples of the blue pigment include C.I. I.
Pigment Blue 15, C.I. I. Pigment Blue 1
5: 6, C.I. I. Pigment Blue 22, C, I.I. Pigment Blue 60, C.I. I. Pigment Blue 64 and the like.

Examples of the green pigment include C.I. I.
Pigment Green 7, C.I. I. Pigment Green 3
6, etc. are mentioned. Examples of the brown pigment include C.I. I. Pigment Brown 23, C.I. I. Pigment Brown 25, C.I. I. Pigment Brown 26,
Etc. Examples of the black pigment include C.I.
I. Pigment Black 7 and the like.

These pigments may be used alone or in combination of two or more. In the present invention, among these, pigments having an acidic group such as Pigment Yellow 138, Pigment Yellow 139, Pigment Yellow 185 and Pigment Yellow 83 are preferable,
Pigment Yellow 138, Pigment Yellow 13
9, Pigment Yellow 185, Pigment Red 25
4, Pigment Green 36, Pigment Blue 15 and the like are particularly preferable.

The content of the pigment in the pigment dispersion composition is usually 5 to 80% by mass, preferably 10 to 70% by mass. When the content is less than 5% by mass,
The coloring power may be insufficient, and if it exceeds 80% by mass, the viscosity of the pigment dispersion composition may increase.

-Organic solvent- The organic solvent is not particularly limited and may be appropriately selected from known ones. For example, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol. (Poly) alkylene glycol monoalkyl ethers such as monoethyl ether, diethylene glycol monomethyl ether, ethylene glycol monoethyl ether and acetic acid esters thereof;
Acetic acid esters such as ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate; aromatic hydrocarbons such as benzene, toluene, xylene; methyl ethyl ketone, acetone, methyl isobutyl ketone, cyclohexanone And the like; alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol, and glycerin. These may be used alone or in combination of two or more. Among these, alkylene glycol monoalkyl ethers, acetic acid esters thereof, acetic acid esters, methyl ethyl ketone, and the like are preferable.

The content of the organic solvent in the pigment dispersion composition is usually 10 to 1000 parts by mass, preferably 20 to 500 parts by mass, relative to 100 parts by mass of the pigment. When the content is less than 10 parts by mass,
The viscosity of the pigment dispersion composition may increase to 1000
If it exceeds the mass part, it may be difficult to secure a space during storage.

-Binder Polymer Having Acidic Group- The pigment dispersion composition of the present invention preferably contains a binder polymer having an acidic group. The binder polymer having an acidic group is capable of imparting both properties of dispersion stability of the pigment and alkali developability when used as a colored photosensitive composition. For example, (meth) acrylic acid and Examples thereof include copolymers with (meth) acrylic acid esters, styrene / maleic anhydride copolymers, and reaction products of styrene / maleic anhydride copolymers with alcohols. These may be used alone or in combination of two or more. Among these,
Excellent pigment dispersibility, when used as a colored photosensitive composition, excellent compatibility with polyfunctional monomers and photopolymerization initiators,
Those having appropriate alkali developer solubility, organic solvent solubility, strength, softening temperature, etc. are preferred, and specifically (meth)
A copolymer of acrylic acid and (meth) acrylic acid ester is preferable.

The weight average molecular weight of the binder polymer having an acidic group is preferably 5,000 to 200,000. When the weight average molecular weight is less than 5,000, there may be a problem in forming a coating film when used as a colored photosensitive composition, and when it exceeds 200,000, the viscosity of the colored photosensitive composition increases. Sometimes.

The content of the binder polymer having an acidic group in the pigment dispersion composition is usually 10 to 200 parts by mass with respect to 100 parts by mass of the pigment,
20 to 150 parts by mass is preferable. If the content is less than 10 parts by mass, the steric repulsion effect may not be obtained, and if it exceeds 200 parts by mass, the viscosity of the dispersion may increase.

The pigment dispersion composition of the present invention can be prepared, for example, by the following method. 1) A method in which a composition obtained by previously mixing the pigment and the pigment dispersant is added to and dispersed in the organic solvent (or vehicle) 2) The organic solvent (or vehicle) is mixed with the pigment and Method 3) in which a pigment dispersant is added separately and dispersed 3) A method in which the pigment and the pigment dispersant are separately dispersed in advance in the organic solvent (or vehicle), and the resulting dispersions are mixed (in this case, The pigment dispersant may be dispersed only in the organic solvent) 4) A method of dispersing the pigment in the organic solvent (or vehicle) and then adding the pigment dispersant to the obtained dispersion.

The vehicle means a part of a medium in which the pigment is dispersed when the coating material is in a liquid state, and is a component (binder) which is in a liquid state and binds with the pigment to harden the coating film. And a component for dissolving and diluting (the organic solvent).

The disperser used to disperse the pigment is not particularly limited, and examples thereof include known dispersers such as a kneader, roll mill, attritor, super mill, dissolver, homomixer and sand mill.

To form a colored image using the pigment dispersion composition, for example, a coating solution containing the pigment dispersion composition is applied on a support and dried to form a layer of the pigment dispersion composition.
Alternatively, a layer of this pigment dispersion composition formed on a temporary support is transferred onto a support, and a layer of a known positive or negative photosensitive resin composition is formed thereon, exposed and developed. Then, a method of removing the layer of the pigment dispersion composition in the same region together with the layer of the unexposed photosensitive resin composition can be performed.

The pigment dispersion composition of the present invention comprises a substantially colorless pigment dispersant, does not impair the hue of the pigment, and is particularly excellent in hue purity, colored hue and light transmittance.
Further, the pigment is uniformly and finely dispersed and has excellent dispersibility, and the pigment is not agglomerated due to storage over time, has excellent dispersion stability, and has a high coloring density. Even when it is dispersed together with a binder polymer having an acidic group, the dispersibility and dispersion stability described above can be maintained, and alkali developability is also obtained. Therefore, it can be suitably applied to a wide range of paints, printing inks, color display boards and the like.

<Colored Photosensitive Composition> The colored photosensitive composition contains at least the pigment dispersion composition of the present invention and a photosensitive composition. —Pigment Dispersion Composition— The pigment dispersion composition is as described above, and the preferred embodiments are also the same.

—Photosensitive Composition— As the photosensitive composition, for example, JP-A-3-282 can be used.
And the photosensitive composition described in JP-A-404, and specifically, a photosensitive composition composed of a negative type diazo resin and a binder, a photopolymerizable composition, and a photosensitive composition composed of an azide compound and a binder. Examples thereof include a composition and a cinnamic acid type photosensitive composition. The photosensitive composition is known to be developable with an alkaline aqueous solution and developable with an organic solvent, but can be developed with an alkaline aqueous solution in terms of pollution prevention, labor safety and the like. Those are preferable.

—Photopolymerizable Composition— In the present invention, the photopolymerizable composition is particularly preferable among the photosensitive compositions. The photopolymerizable composition contains at least a binder polymer having an acidic group, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator.

—Binder Polymer Having Acidic Group— The binder polymer having an acidic group contained in the photopolymerizable composition has an acidic group suitably contained in the pigment dispersion composition of the present invention. It is a binder polymer.

The content of the binder polymer having an acidic group in the colored photosensitive composition is about 20 to 80% by mass based on the total solid content. The content is 2
If it is less than 0% by mass, problems may occur in forming the coating film, and if it exceeds 80% by mass, it may be difficult to exert the ability of other materials.

—Polyfunctional Monomer Having Two or More Ethylenically Unsaturated Double Bonds— Examples of the polyfunctional monomer having two or more ethylenically unsaturated double bonds include those described in JP-A-60-258539.
Known (meth) acrylic acid ester,
Urethane (meth) acrylate, (meth) acrylic acid amide, an allyl compound, a vinyl ester, etc. are mentioned. These may be used alone or in combination of two or more. Among these, (meth) acrylic acid ester is preferable.

The content of the polyfunctional monomer having an ethylenically unsaturated double bond in the colored photosensitive composition is preferably 10 to 60% by mass based on the total solid content. If the content is less than 10% by mass, the curing power during exposure may be insufficient, and if it exceeds 60% by mass,
It may be difficult to exercise the capabilities of other materials.

--Photopolymerization Initiator-- The photopolymerization initiator has a wavelength of about 300 to 500 n.
It is preferable to use at least one compound having a molecular extinction coefficient of at least about 50 in m. Examples of such a compound include JP-A-2-48664, JP-A-1-152449, and JP-A-2. -1533
Aromatic ketones, lophine dimers, benzoin, benzoin ethers, polyhalogens, etc. described in JP-A-53 can be mentioned. These may be used alone or in combination of two or more. Among these,
4,4'-bis (diethylamino) benzophenone and 2
-(O-Chlorophenyl) -4,5-diphenylimidazole dimer combination, and 4- [p-N, N-di (ethoxycarbonylmethyl) -2,6-di (trichloromethyl) -s-triazine] Is preferred.

The content of the photopolymerization initiator in the colored photosensitive composition is preferably 0.2 to 10% by mass based on the total solid content of the colored photosensitive composition. The content is
If it is less than 0.2% by mass, the exposure sensitivity may be lowered, and if it exceeds 10% by mass, the exposure sensitivity may be too high (control may be difficult).

The colored photosensitive composition can be prepared, for example, by mixing the pigment dispersion composition and the photosensitive composition according to appropriately selected conditions and techniques.

The formation of a colored image using the colored photosensitive composition can be basically performed by the following steps 1) to 3). 1) After the pigment dispersion composition is prepared, the step of preparing the colored photosensitive composition using the pigment dispersion composition 2) The obtained colored photosensitive composition is coated on a substrate and dried, or another Step 3 of transferring a layer formed by coating on a temporary support and drying to a substrate to form a layer of the colored photosensitive composition 3) exposing the layer of the colored photosensitive composition formed on the substrate Process of developing and forming a pattern

To manufacture a color filter used for a liquid crystal display or the like, the above steps 2) and 3) are repeated,
This can be done by combining the patterns of the second and subsequent colors. A method of manufacturing a color filter by a transfer method is disclosed in, for example, Japanese Patent Application Laid-Open Nos.
-72724, JP-A-5-80503, JP-A-5-173320 and the like.

-Substrate-A transparent material such as a glass plate or a transparent plastic plate is generally used as the substrate. In order to improve the adhesion between the substrate and the colored photosensitive composition, various commercially available silane coupling agents or the like are added to the colored photosensitive composition, or the substrate is subjected to a coupling treatment in advance. You may stay.

The colored photosensitive composition of the present invention has a high coloring density and, at the same time, is particularly excellent in hue purity, colored hue and light transmittance, and, as described above, also has alkali developability. Therefore, it can be suitably used for forming a multicolor image such as a color proof and manufacturing a color filter.

[0089]

EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. still,
All “parts” in the examples represent “parts by mass”.

-Synthesis of Triazine Compound Represented by General Formula (1) or (2)-(Example 1): Synthesis of Exemplified Compound (4) First, 18.4 parts of cyanuric chloride was prepared at -10 ° C. Add 100 parts of acetone and 8.4 parts of sodium hydrogen carbonate and stir with a three-one motor.
14.9 parts of aminobenzimidazolone were added. After 1 hour, the reaction mixture was poured into water and the precipitate was filtered and dried. Subsequently, 100 parts of acetone and 8.4 parts of sodium hydrogen carbonate were added thereto, and the mixture was stirred in the same manner as above,
3,5-bis (methoxycarbonyl) aniline 20.9
Parts were added and reacted at 30 ° C. for 3 hours. The obtained reaction mixture was poured into water, the precipitate was filtered, washed with water and dried, and then 3-diethylaminopropylamine 65 was added thereto.
Parts were added and reacted at 80 ° C. for 1 hour. Then, the reaction mixture was poured into aqueous potassium carbonate, extracted with 2-propanol, concentrated, and then purified by column (methanol / triethylamine = 100/1) to obtain 30.9 parts of the exemplified compound (4) as a light brown liquid. Obtained.

The results of identifying the obtained compound by NMR analysis (data), ¹ H-NMR (300 MHz, DM
SO-d ₆ ) δ 10.60 (br, 1H), 10.38
(Br, 2H), 7.95 (s, 2H), 7.75
(S, 1H), 7.40 (s, 1H), 7.09 (d,
1H), 6.84 (d, 1H), 3.58 (s, 6
H), 3.42 (t, 2H), 2.48 (m, 6H),
It was 1.62 (m, 2H) and 1.01 (t, 6H).

Example 2 Synthesis of Exemplified Compound (7) First, 100 parts of acetone and 4 parts of sodium hydroxide were added to 18.4 parts of cyanuric chloride at −10 ° C. and stirred with a three-one motor. Then, 7.3 parts of diethylamine was added dropwise thereto. Then, after reacting for 1 hour, 22 parts of 3-dibutylaminoaniline and 8.4 parts of sodium hydrogen carbonate were further added and reacted at 20 ° C. for 2 hours. The resulting reaction mixture is poured into water, the precipitate is collected by filtration,
Washed with water. After drying the filtered material, 300 parts of acetone was added, 13.4 parts of 5-aminobenzimidazolone and 4 parts of sodium hydroxide were added, and the mixture was reacted at 55 ° C. for 4 hours. Then, the obtained reaction mixture was poured into potassium carbonate water, extracted with 2-propanol, concentrated, and then purified by column (methanol / triethylamine = 1.
00/1) to give the above-mentioned exemplary compound (7) 2 as a light brown liquid.
3.1 parts were obtained.

The results of identifying the obtained compound by NMR analysis (data), ¹ H-NMR (300 MHz, DM
SO-d ₆ ) δ 10.62 (br, 1H), 10.44
(Br, 1H), 9.90 (br, 1H), 7.52
(S, 1H), 7.32 (dm, 1H), 7.24
(D, 2H), 7.18 (d, 1H), 6.84 (m,
2H), 6.78 (s, 1H), 3.56 (m, 4)
H), 3.25 (t, 4H), 1.87 (m, 4H),
1.67 (m, 4H), 1.11 (m, 6H), 0.9
It was 8 (t, 6H).

-Pigment Dispersion Composition- (Example 3) A pigment-containing composition shown below was used in a motor mill M-50 (manufactured by Eiger) to have a diameter of 0.65 mm.
Using the zirconia beads of No. 3, the pigment was dispersed at a peripheral speed of 9 m / s for 9 hours to prepare a red pigment dispersion composition (1) of the present invention. [Composition] C. I. Pigment Red 254 ... 6.4 g-Exemplary compound (4) obtained in Example 1 (pigment dispersant) ... 0.9 g (triazine compound represented by the general formula (1) or (2))-methacryl Acid / benzyl methacrylate copolymer 15.8 g (molar ratio 28/72, weight average molecular weight 30,000, 40% solution of 1-methoxy-2-propyl acetate) 1-methoxy-2-propyl acetate 57.2 g

(Examples 4 to 6) The C.I.
I. Pigment Red 254, instead of C.I. I. Pigment Yellow 138, C.I. I. Pigment Green 3
6, C.I. I. Pigment Blue 15: 6 was used, and yellow, green, and blue pigment dispersion compositions (2) to (4) of the present invention were prepared in the same manner as in Example 3.

(Examples 7 to 9) In place of 0.9 g of the exemplified compound (4) used in Example 3, 0.4 g of the exemplified compound (7) obtained in Example 2 and the exemplified compound (12) described above. ) 0.6
g, and 0.7 g of the above-exemplified compound (13) [triazine compound represented by the general formula (1) or (2)] were used in the same manner as in Example 3 for red-colored present invention. Pigment dispersion compositions (5) to (7) were prepared. The exemplified compounds (12) and (13) were synthesized by a method similar to Example 1 and the like.

Example 10 In place of 0.9 g of the exemplified compound (4) used in Example 4, the exemplified compound (19) described above was used.
A yellow pigment dispersion composition (8) of the present invention was prepared in the same manner as in Example 4 except that 0.8 g [the triazine compound represented by the general formula (1) or (2)] was used. .
The exemplified compound (19) was synthesized by a method similar to that in Example 1 and the like.

Example 11 In place of 0.9 g of the exemplified compound (4) used in Example 5, the exemplified compound (25) described above was used.
A green pigment-dispersed composition (9) of the present invention was prepared in the same manner as in Example 5, except that 0.4 g of the triazine compound represented by the general formula (1) or (2) was used. .
The exemplified compound (25) was synthesized by a method similar to that in Example 1 and the like.

Example 12 In place of 0.9 g of the exemplified compound (4) used in Example 6, the exemplified compound (26) described above was used.
A green pigment dispersion composition (10) of the present invention was prepared in the same manner as in Example 6 except that 0.6 g of the triazine compound represented by the general formula (1) or (2) was used. . The exemplified compound (26) was synthesized by a method similar to that in Example 1 and the like.

Comparative Example 1 A red pigment dispersion composition (11) was prepared in the same manner as in Example 3 except that the following compound was used in place of the exemplified compound (4) used in Example 3. did.

[0101]

[Chemical 11]

Comparative Examples 2 to 4 In Comparative Example 1, C.I.
I. Pigment Red 254, instead of C.I. I. Pigment Yellow 138, C.I. I. Pigment Green 3
6, C.I. I. Pigment Blue 15: 6 was used, and yellow, blue, and green pigment dispersion compositions (12) to (14) were prepared in the same manner as in Comparative Example 1.

(Evaluation 1) Using the pigment dispersion compositions (1) to (10) of the present invention and the comparative pigment dispersion compositions (11) to (14) obtained above, the following evaluations were carried out. . (1) Viscosity measurement: For each pigment dispersion composition obtained, R
The viscosity at 30 ° C. was measured using an E80 type viscometer (manufactured by Toki Sangyo Co., Ltd.). The viscosity was measured for the sample immediately after the pigment dispersion and for the sample after the pigment dispersion composition was stored at room temperature (28 ° C) or 40 ° C for 7 days. The measurement results are shown in Table 1 below. (2) Contrast measurement: each of the obtained pigment dispersion compositions,
It was applied on a glass substrate so as to have a thickness of 5 μm, and a coating film (pigment dispersion film) was formed to obtain a sample. This sample is placed between two polarizing plates, and the amount of transmitted light when the polarization axes are parallel and perpendicular is measured, and the ratio is defined as the contrast ("1990 7th Color Optics Conference,
"Color filter for 512-color display 10.4" TFT-LCD, Ueki, Koseki, Fukunaga, Yamanaka "was referred to. ) The measurement results are shown in Table 1 below. (3) Transmittance measurement: Using a sample prepared in the same manner as in "(2) Contrast measurement" above, MPS-2000 (manufactured by Shimadzu Corporation) was used to measure the transmittance at 450 nm. The measurement results are shown in Table 1 below.

-Colored Photosensitive Composition- (Example 13) The following composition was used in a motor mill M-
50 (manufactured by Eiger) using zirconia beads having a diameter of 0.65 mm and dispersed at a peripheral speed of 9 m / s for 9 hours to prepare a colored photosensitive composition (i;
Red) was prepared. [Composition] -Red pigment dispersion composition of Example 3 ... 33.0 g-Methacrylic acid / benzyl methacrylate copolymer ... 9.0 g (molar ratio 28/72, weight average molecular weight 30,000, 30% 1-methoxy- 2-propylacetate solution) -Pentaerythritol tetraacrylate-5.2g-4- [p-N, N-di (ethoxycarbonylmethyl)]-2,6-di (trichloromethyl) -5-triazine ... 0.2g・ Hydroquinone monomethyl ether… 0.01g ・ 1-Methoxy-2-propylacetate… 62g

(Examples 14 to 16) In Example 13, instead of the red pigment dispersion composition of Example 3, the yellow pigment dispersion composition of Example 4 and the green pigment dispersion composition of Example 5 were used. In the same manner as in Example 13, except that the blue pigment dispersion composition of Example 6 was used, the colored photosensitive composition (ii; yellow), (iii; green), (iv; Blue) was prepared.

(Evaluation 2) After measuring the viscosity of the colored photosensitive compositions (i) to (iv) for producing a color filter obtained as described above by the same method as the above-mentioned "(1) Viscosity measurement" The colored photosensitive compositions were coated on separate glass substrates using a spin coater and dried at 100 ° C. for 2 minutes to form a film (colored photosensitive film) having a thickness of about 2 μm. Next, under a nitrogen stream, it was exposed with an ultra-high pressure mercury lamp and then developed with a 1% sodium carbonate aqueous solution. And for each color,
The contrast was measured by the same method as the above-mentioned “(2) Contrast measurement”. The measurement results are shown in Table 1 below.

[0107]

[Table 1]

From the results of Table 1 above, the pigment dispersion composition (1) using the triazine compound of the present invention as the pigment dispersant
In the cases of (10) to (10), the viscosity increase due to dispersion was small and the flowability was excellent, the viscosity did not increase with time, and the dispersion stability after dispersion was good. Further, regardless of the pigment type, good dispersion characteristics were exhibited in all cases. The film (pigment dispersion film, colored photosensitive film) formed using the pigment dispersion compositions (1) to (10) and the colored photosensitive compositions (i) to (iv) is formed into a thin film and has a high coloring density. It was possible to form a colored film (color filter) having a good contrast, excellent light transmittance and excellent color purity, and having a clear hue. On the other hand, comparative pigment dispersion compositions (11) to (1
In 4), the increase in viscosity due to dispersion was large, and the dispersibility and fluidity were poor, and the stability over time was also poor. Further, due to the hue shift caused by the coloring of the pigment dispersant itself, it was inferior in light transmittance and contrast, and it was not possible to obtain a clear colored film (color filter) having a good hue.

[0109]

According to the present invention, a novel triazine compound that is substantially colorless can be provided. Further, according to the present invention, substantially colorless, there is no pigment aggregation,
It is possible to provide a pigment dispersant that realizes stable and good dispersibility and fluidity of a pigment and is also excellent in light transmittance. Furthermore, according to the present invention, containing the pigment dispersant,
The pigment has excellent dispersibility, fluidity, etc. and coloring concentration, and is not particularly impaired in the hue of the pigment, and is particularly excellent in hue purity, coloring hue and light transmittance, and has aptitude for alkali development.
A pigment dispersion composition suitable for a wide range of printing inks, color display boards and the like, and containing the pigment dispersion composition,
Provide a colored photosensitive composition that is particularly excellent not only in color density but also in hue purity, color hue and light transmittance, and has alkali development suitability and is suitable for forming multicolor images such as color proofs and for manufacturing color filters. can do.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) C08F 2/44 C08F 2/44 C C08K 5/00 C08K 5/00 C08L 101/02 C08L 101/02 C09B 67 / 20 C09B 67/20 L 67/46 67/46 B (72) Inventor Sachiko Arai 200, Onakazato, Fujinomiya City, Shizuoka Prefecture Fuji Photo Film Co., Ltd. (72) Inventor Akihiko Takeda 200, Onakazato, Fujinomiya City, Shizuoka Prefecture Fuji Photo Film Co., Ltd. (72) Inventor Katsuyuki Kito 200 Onakazato, Fujinomiya-shi, Shizuoka Prefecture Fuji Photo Film Co., Ltd. F-term (reference) 2H086 BA52 BA55 BA59 BA60 4C063 AA01 AA03 BB08 BB09 CC43 DD26 EE10 4D077 AA03 AA08 AB04 AB05 AC05 DC01X DC04X DC06X DC38X DC39X DC48X DC51X DC71X DC76X 4J002 BC041 BG011 EE039 EH078 EP018 ET008 EU119 EU186 EU189 EU236 EV086 EV246 EV306 EV326 FD097 FD310 FD316 GH00 GH01 GP00 4J011 PA43 PA45 PA65 PA69 PA70 PB25 PB40 PC02 PC08

Claims (6)

[Claims] 1. A triazine compound represented by the following general formula (1) or (2): [Chemical 1] [In the general formulas (1) and (2), R ¹ is a halogen atom,
Hydroxyl group, amino group, alkoxy group, alkylamino group,
It represents a dialkylamino group, a heterocyclic group, or a —X ³ —Ar group, and Ar represents a hydrocarbon aromatic ring or a hetero atom-containing aromatic ring, and may be a condensed ring. X ¹ , X ² and X ³ each independently represent —O—, —N (R ² ) — and may be the same or different, and R ² is a hydrogen atom, an alkyl group, an alkenyl group or an alkynyl. Group represents an aryl group.
In the general formula (1), R ³ , R ⁴ and R ⁵ are each independently a hydrogen atom, a halogen atom, an amino group, an alkoxy group, an alkyl group, an alkenyl group, an alkynyl group, an aryl group,
It represents an alkylthio group, an amide group or an ester group, which may be the same or different. ] 2. A pigment dispersant containing the triazine compound according to claim 1. 3. The pigment dispersant according to claim 2, which has a molar extinction coefficient of less than 1000 at a wavelength of 400 nm or more. 4. A pigment dispersant according to claim 2 or 3,
A pigment dispersion composition comprising a pigment and an organic solvent dispersed therein. 5. The pigment dispersion composition according to claim 4, which contains a binder polymer having an acidic group. 6. The pigment dispersion composition according to claim 4, a binder polymer having an acidic group, a polyfunctional monomer having two or more ethylenically unsaturated double bonds, and a photopolymerization initiator. A colored photosensitive composition comprising: