JP2001081350A - Coloring material - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a coloring material capable of providing a color filter improved in spectral characteristics by transforming a soluble pigment precursor to an insoluble pigment by using a solution containing a specific soluble pigment precursor, a solvent and a stabilizing agent. SOLUTION: By using a solution containing (A) a soluble pigment precursor capable of being transformed to an insoluble pigment, (B) a solvent capable of dissolving the ingredient A and (C) a stabilizing agent comprising an organic material having a structure or a functional group capable of stabilizing dispersibility of an insolubilized pigment in the ingredient B, a coloring material in which the insolubilized pigment is stably dispersed in the ingredient B by transforming the ingredient A to the insoluble pigment. The transformation of the ingredient A to the insoluble pigment is preferably carried out by a chemical means, a thermal means, a photolysis, an irradiation inducing means or the like. As the insoluble pigment, it is preferable to have a polar group such as a primary amine, a secondary amine, a cyclic amine, hydroxy group or the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pigment-containing coloring material which can be stably dispersed in many organic solvents at a high concentration and a method for producing the same.

[0002] This coloring material is used alone or in addition to an inverter component, as various paint systems, coating materials, printing inks, ink jet printing inks, toners, or preparations in the same manner as ordinary dyes and pigments. You. In particular, the color filter obtained from the coloring material of the present invention can have improved spectral characteristics (color purity, high transmittance, high contrast) as compared with conventional ones.

[0003]

BACKGROUND OF THE INVENTION Generally, dyes have poor resistance to light, heat, solvents and chemicals, while pigments have dispersion, dispersion stability, transparency, absorption or transmission spectrum profile sharpness or diffusivity. There is a problem of lack of. In this regard, JP-A-7-188234 or JP-A-8-6242 are subject to chemical, thermal, photolytic means, laser or other line irradiation to produce insoluble pigment particles of nanometer size. By using a soluble pigment precursor, a novel coloring material having both advantages of a dye and a pigment (solubility of the dye and weather resistance of the pigment) has been proposed.

[0004]

However, when the coloring material disclosed in JP-A-7-188234 or JP-A-8-6242 is used, the pigment can be uniformly dispersed at a high concentration in the polymer film. When the pigment precursor is converted into insoluble pigment particles in a polymer film by a chemical, thermal, photolytic or irradiation-induced method, partial desorption occurs due to volatilization of the precursor, resulting in uneven film thickness. A significant reduction. In the case of a soluble pigment precursor, generally, a bulky functional group is introduced to impart solubility to a solvent, and the bulky functional group is eliminated to form an insoluble pigment. Become. Further, when these eliminated functionalities are present in a large amount in the film, the influence thereof is concerned. For these reasons, it is difficult to apply to a field that requires dimensional accuracy of a color filter or the like, particularly, a smoothness of a coating film.

In order to avoid this problem, when the pigment is converted into an insoluble pigment in a solvent before forming a coating film, the pigment precipitates and the solubility in the solvent is extremely reduced. Storage stability is inferior due to the formation of
Preparation of a highly concentrated solution itself becomes difficult.

The present invention has been made in view of such circumstances,
The detailed principle is unknown, but overcomes these conditions. That is, when (1) the soluble pigment precursor that can be converted to an insoluble pigment is dissolved in (2) a solvent capable of dissolving the soluble pigment precursor, (3) the soluble pigment precursor is further dissolved in the solvent. By converting the soluble pigment precursor into an insoluble pigment in a system in which a stabilizer made of an organic substance having a structure or a functional group capable of stabilizing the dispersibility of the pigment, the pigment insolubilized in the solvent is stabilized. A coloring material present in a form dispersed therein, and a method for producing the same, and a coloring material which is concentrated and solidified by concentrating the coloring material, a method for producing the same, and a coloring material which redisperses the obtained solidified coloring material in a solvent and the same. A production method, and a solution comprising a soluble pigment precursor which can be converted into the insoluble pigment and an organic material having a structure or a functional group capable of stabilizing the dispersibility of the insolubilized pigment in the solvent. About coloring material consisting of adducts formed by the interaction of the agent. In particular, the coloring material of the present invention solves the above-mentioned problems, and can easily obtain a polymer dispersion film of a pigment having a high concentration and excellent coating smoothness. (High transmittance and high contrast) can be applied to a color filter with improved characteristics.

[0007]

SUMMARY OF THE INVENTION The present invention relates to an organic solvent having a structure or a functional group capable of stabilizing the dispersibility of an insolubilized pigment and a soluble pigment precursor capable of being converted into an insoluble pigment. It is achieved by dissolving a saturated amount, applying a chemical means, a thermal means, a photolytic or irradiation-inducing means or a combination thereof, and pigmenting at least a part of the precursor. This coloring material, even if concentrated after performing the pigmentation of the soluble precursor due to the presence of an organic substance having a structure or a functional group capable of stabilizing the dispersibility of the insolubilized pigment in the solvent, Since there is no remarkable suspended matter, a high-concentration dispersion of a soluble precursor that is at least partially pigmented can be easily realized, and overcomes the above-mentioned problems caused by forming an insoluble pigment after forming a coating film or the like. It is possible to do.

The coloring material of the present invention exists stably even when concentrated, but when the concentration is further continued, it precipitates as a solid. This solid may have crystallinity, can be easily isolated from the dispersion, and can withstand long-term storage. Isolation from the dispersion makes it possible to easily remove extra impurities such as stabilizers by washing or the like.

[0009] The solidified coloring material of the present invention is also easily stable even in a solvent which cannot be easily dispersed by an insoluble pigment alone, without requiring a complicated dispersing step or a dispersing agent for the pigment. It is possible to make a dispersion or a concentrated solution thereof.

Although the detailed reasons for these are unknown, during the process of converting a soluble pigment precursor into an insoluble pigment, an adduct is formed by interacting with the stabilizer at a molecular level, and the solvent of the stabilizer is removed. This is presumed to be due to the fact that the solubility in water is imparted to the insoluble pigment. Since the insoluble pigment and the stabilizer strongly interact with each other, the adduct can be isolated as a crystalline solvent-soluble solid.

Since the coloring material of the present invention does not require a complicated dispersing step or a dispersing agent for a pigment, a mixed dispersion of a plurality of coloring materials and a highly concentrated solution thereof can be easily obtained. It is also possible to easily adjust the hue and the like.

As the soluble pigment precursor which can be used in the present invention, all those described in JP-A-7-188234 or JP-A-8-6242 can be used. That is, it is a soluble pigment precursor that is converted to an insoluble pigment by chemical, thermal, photolytic or irradiation-inducing means, and more specifically, the soluble pigment precursor is represented by Formula I below: It is a coloring material that is a compound.

A (B) X (I) wherein x is a number from 1 to 4, and A is a quinacridone, anthraquinone, perylene, indigo, quinophthalone, isoindolinone, dioxazine, diketopyrrolololole or azo series. Residues of the colorant, these residues being A
Is bonded to x groups B via a nitrogen atom which is part of B is a group bonded to A, and is represented by any of the following formulas.

[0014]

Embedded imageIn formulas II, III and IV, m, n and p are each other
Is independently 0 or 1, and X is C₁-C₄Alkylene
Or C₂-C₈Alkenylene, and Y is a group -V-
(CH₂)_qAnd Z is a group -V- (CH₂)_rIn
Where V is C₃-C₆With cycloalkylene
Where q is 1 to 6, r is a number from 0 to 6,
R₁And R₂Is independently of each other hydrogen, C₁-C₆Archi
Le, C₁-C₄Alkoxy, halogen, CN, NO₂,
Unsubstituted or C₁-C ₄Alkyl, C₁−
C₄Fe substituted by alkoxy or halogen
Q is hydrogen, CN, Si
(R₄)₃, A group C (R₅) (R ₆) (R₇) (Here
And R₅, R₆And R₇Are independently hydrogen or
Is halogen and R₅, R₆And R₇Out of
At least one is halogen), a group of the formula

[0015]

Embedded image Wherein R ₁ and R ₂ have the meanings given above, the radical SO
₂ R ₈ or SR ₈ (where R ₈ is C ₁ -C ₄
Alkyl), a group CH (R ₉ ) ₂ (wherein
R ₉ is unsubstituted or C ₁ -C ₄ alkyl,
C ₁ -C ₄ alkoxy or phenyl substituted by halogen), or a group of any of the following formulae:

[0016]

Embedded image R ₃ and R ₄ are each independently hydrogen C ₁ -C ₁₈ alkyl or a group of the following formula:

[0017]

Embedded image Wherein X, Y, R ₁ , R ₂ , m, and n have the meanings described above, or R ₃ and R ₄ together with the nitrogen atom to which they are attached are a pyrrolidinyl group, A piperidinyl group or a morpholinyl group), and A (B)
_x is additionally

[0018]

Embedded image Or it may contain the group -NH _2.

The soluble pigment precursor that can be used in the present invention can also be obtained from an insoluble pigment having a polar group selected from the group consisting of primary amines, secondary amines, cyclic amines, and hydroxyl groups. .

The stabilizer composed of an organic substance having a structure or a functional group capable of stabilizing the dispersibility of the insoluble pigment in the solvent of the present invention is> CO, -NH ₂ ,>NH,> N-, =
N ⁺ <, -CONH ₂ , -CONH-, -NHCOO
-,> NCOO-, -NHCONH-, (-NHCO)
_As long as it has a group selected from the group consisting of 2N- and -OH, it can be preferably used as an ordinary organic compound, oligomer or polymer, alone or in combination. Become.

[0021] Preferably, the compound has an amine value, and more preferably, the compound has an amine value of 1 mgKOH / g or more and 230 mgKOH / g or less. Most preferably, they have urethane bonds. Specifically, acrylate, methacrylate, vinyl ester, vinyl carbazole and its derivatives, vinyl pyrrolidone and its derivatives, vinyl pyridine and its derivatives, acrylamide and its derivatives, vinyl imidazole and its derivatives, ethylene imine and its derivatives Phenol and its derivatives, urea and its modified urea, melamine, amide, amide imide and its derivatives, amino acids, and urethane compounds, oligomers, or polymers alone or in combination.

The stabilizer of the present invention can also be used as a binder component into which a reactive double bond group is introduced and which can be polymerized with another monomer or a reactive polymer after forming a coating film. At this time, the amount of the reactive double bond group introduced is
It is preferable that the average number be in the range of 0.1 to 20 per molecule.

The soluble pigment precursor and stabilizer are mixed in a weight ratio of 0.01: 99.99 to 80:20. Preferably, the weight ratio is from 1:99 to 70:30, more preferably from 5:95 to 60:40, and most preferably from 10:90 to 50:50 by weight.

Suitable solvents to be used are exemplified below.
Ethers such as tetrahydrofuran and dioxane; glycol ethers such as ethylene glycol methyl ether, ethylene glycol ethyl ether, diethylene glycol monomethyl ether and diethylene glycol monoethyl ether; aprotic solvents such as acetonitrile, benzonitrile, N,
N-dimethylformamide, nitrobenzene, N-methylpyrrolidone, halogenated aliphatic or aromatic hydrocarbons such as trichloromethane, benzene unsubstituted or substituted by alkyl, alkoxy or halogen, such as xylene, anisole and chlorobenzene, And an aromatic N-heterocyclic compound,
For example, pyridine, picoline or quinoline; alcohols such as methanol, ethanol, isoptanol, propylene glycol and diacetone alcohol; carboxylic esters and lactones such as propylene carbonate, ethyl acetate, butyl acetate, methoxypropyl acetate, methyl propionate , Ethylbenzoate, γ-butyrolactone and γ-valerolactone; sulfoxides, such as dimethyl sulfoxide; sulfones, such as dimethyl sulfone and diethyl sulfone: ketones;
For example, dimethyl ketone, methyl ethyl ketone, cyclopentanone, cyclohexanone and the like can be used, and monomers having various reactive functional groups can also be used. The coloring material according to the invention preferably has a solids content of from 1 to 90% by weight, preferably from 5 to 80% by weight, more preferably from 10 to 70% by weight, based on the solution, using one or a mixture of the abovementioned solvents. %, Most preferably 20
To 60% by weight.

The method of converting the soluble pigment precursor into an insoluble pigment is the addition of an acid, the addition of a base, or the irradiation of electromagnetic radiation or electron radiation or neutron radiation and / or heating. The coloring material obtained by the conversion into the insoluble pigment can be concentrated without any apparent precipitate even if a solution in which the soluble pigment precursor is dissolved in the solvent until the coloring material is saturated is used. The solution produced as above,
In general, when applied on a suitable substrate, the pigment does not exhibit its intrinsic performance. Although the detailed reason is unknown, the insoluble pigment at the molecular level interacts with the stabilizer,
This is because it is presumed that the adduct is stably present in the matrix while being formed. These may also be, where appropriate, chemical reactions due to the generation of acids or bases from the various additives, electromagnetic radiation, such as visible light, UV, laser light or X-ray irradiation or electron beam irradiation or neutron beam irradiation and / or By performing the heat treatment, the pigment shows its original properties.

The coloring material of the present invention is a plastic material, a melt,
Spinning solution, paint system, positive or negative UV resist, positive or negative electron beam resist, coating material,
Printing inks such as screen printing, gravure printing, flexographic printing or offset printing, non-impact printing inks such as ink jet printing or thermal transfer printing, toner,
Alternatively, it is used as a color filter for a liquid crystal display using a coloring material of a preparation, particularly a resist.

For producing a color filter, a photolithography method, an ink-jet method, an electrodeposition method, a sublimation transfer method and the like are used together with a suitable binder component. The coloring material of the present invention can be preferably used for all of them. .

[0028]

The present invention will be described below in detail with reference to examples. In the examples, "parts" all indicate parts by weight, and "%"
All indicate% by weight.

Example 1 (1) Preparation of solution N, N'-bis-tert-amyloxycarbonyl-
1,4-diketo-3,6-di (4'-chlorophenyl)
4 parts of pyrrolo- [3,4-c] pyrrole (DPP) are dissolved in 76 parts of methoxypropyl acetate (PGMEA) dried by Molecular Sheeps 4A,
Filtered through a μm filter. Add Disperb to this solution
yk-164 (manufactured by Big Chemie Japan, solid content 6)
0%, amine value 18 mgKOH / g) 1.36 parts by PG
The solution dissolved in 1.64 parts of MEA was added and stirred at room temperature to obtain a transparent orange-yellow solution.

(2) Preparation of concentrated solution A small amount of PGM was added to the solution obtained in (1) at a temperature of 40 ° C.
0.32 parts of a 10% methanol solution of hydrochloric acid dissolved in EA was dropped and mixed over 1 hour, and the mixture was further stirred for 1 hour. The resulting solution was a clear fluorescent yellow solution. This solution was concentrated under reduced pressure at a temperature of 40 ° C., and concentrated to a total volume of 40 parts. The obtained solution was a clear orange-yellow solution without any precipitate.

(3) Confirmation by Thin Layer Chromatography The solution prepared in (1), the solution obtained in (2) after concentration, and the solution obtained by dissolving 0.5 part of DPP in 4.5 parts of PGMEA were dissolved in cyclohexane: cyclohexanone. = 7: 3
When (1) and DPP were dissolved in PGMEA, rf = 0.8, and (2), rf =
Only one spot was obtained at the position of 0.7.

(4) Isolation of solidified coloring material The solution obtained in (2) is allowed to stand, the precipitated yellow crystals are aggregated, and the crystals are recrystallized and purified, and dried under vacuum overnight. Thus, a solidified coloring material was obtained. FIG. 1 shows a chart of the ¹ H-NMR spectrum of the obtained solidified coloring material. The solubility of the isolated solid colorant in a solvent was 10% by weight based on PGMEA, 15% by weight based on cyclohexane, 10% by weight based on chloroform, 5% by weight based on ethyl acetate, and 5% by weight based on DPP. It has a solubility difference of 5% by weight based on PGMEA, 10% by weight based on cyclohexanone, 10% by weight based on chloroform, and 1% by weight or less based on ethyl acetate. When the isolated solidified coloring matter was redissolved in cyclohexanone, the solution was a stable solution with no precipitate even when the solid content exceeded 15% by weight.

(5) Preparation of coating solution and coating film 100 parts by weight of a 10% by weight clear solution obtained by re-dissolving the solidified coloring matter obtained in (4) in PGMEA was mixed with a phenol resin (Maruzen Petrochemical Co., Ltd.). Polyvinylphenol PH
MC) 10 parts by weight are dissolved and mixed. After filtration through a 0.1 μm filter, the coating liquid was applied to a thickness of 1.
The composition is applied on a 1 mm 5 × 5 cm glass substrate by a spin coater and dried at room temperature for 30 minutes and on a hot plate at 90 ° C. for 1 minute. This dye coating film was heated in an oven at 200 ° C. for 5 minutes to obtain a red pigment coating film with high transmittance.

(6) Evaluation of Coating Film The content of the insoluble pigment in the red coating film obtained in (5) is 30% by weight in terms of solid content, and the light absorption region is 570 nm or less in this case. The light transmittance was 10% or less, the light transmittance in a light transmitting region, in this case, 620 nm or more, was 87% or more. As a result of measuring the contrast ratio, a value of 3600 was obtained. An attempt was made to mechanically disperse the same pigment as that in the red coating film using a dispersant, but the dispersion could not be performed at all, and a coating film could not be produced.
As a result of measuring the size of the insoluble pigment in the red coating film obtained in (5) using a cross-sectional transmission electron micrograph of the coating film, the average particle size was 10 nm, the particle size distribution was within ± 20%,
That is, it was in the range of 8 to 12 nm.

Comparative Example 1 The solution obtained in Example 1 (1) was concentrated under reduced pressure at a temperature of 40 ° C. without adding hydrochloric acid, and concentrated until the total amount became 2.5 parts. A precipitate was observed in the obtained solution. From the comparison between this result and Example 2, it became clear that a pigmentation operation was necessary to obtain a high-concentration solution.

Comparative Example 2 A solution was prepared in the same manner as in Example 1, (1). Where D
Disperby instead of isperbyk-164
k-180 (solid content 79%, amine value 96 mg KOH /
g, acid value 95 mgKOH / g) 0.013 part by PGME
A solution dissolved in 0.1 part of A was added and stirred at room temperature to obtain a clear orange-yellow solution. To this solution, 0.04 parts of a 10% methanolic hydrochloric acid solution was dropped and mixed, and the mixture was stirred at a temperature of 40 ° C. for 1 hour. An orange precipitate was observed in the resulting solution.

Comparative Example 3 A solution was prepared in the same manner as in Example 1, (1). Where D
Disperby instead of isperbyk-164
k-110 (solid content 52%, acid value 95mgKOH / g)
A solution obtained by dissolving 0.019 part in 0.1 part of PGMEA was added, and the mixture was stirred at room temperature to obtain a transparent orange-yellow solution. 1 in this solution
0.04 parts of a 0% methanolic hydrochloric acid solution was dropped and mixed.
The mixture was stirred for 1 hour at a temperature of ° C. An orange precipitate was observed in the resulting solution.

[0038]

As described above, according to the present invention, when (1) a soluble pigment precursor which can be converted into an insoluble pigment is dissolved in (2) a solvent which can dissolve the soluble pigment precursor, (3) The soluble pigment precursor is converted to an insoluble pigment in a system in which a stabilizer comprising an organic substance having a structure or a functional group capable of stabilizing the dispersibility of the insolubilized pigment in the solvent is present. As a result, no precipitates or remarkable suspended matters are present even when the soluble precursor is converted into an unstable system and then concentrated after pigmentation. It is possible to easily produce a high-concentration solution of a soluble precursor partially converted into an insoluble pigment, and it is possible to overcome the above-described problems caused by (insoluble) pigmentation after forming a coating film or the like.

The coloring material can also be taken out as a crystallized solid by removing the solvent, and this solid is easily redissolved in the solvent to form a stable high-concentration solution in which impurities are eliminated as much as possible. It is also possible to do.

The coloring material of the present invention having the above characteristics can easily obtain a polymer dispersion film of a pigment having a high concentration and excellent coating smoothness. Application to a color filter with improved transmittance and high contrast) becomes possible.

Further, according to the present invention, a soluble pigment precursor and / or an organic substance having a specific structure or a functional group having an affinity for an (insoluble) pigment and a soluble pigment precursor in a medium such as a solvent are added. Dissolved in a saturated amount, as it is, or subjected to a chemical method, a thermal method, a photolytic method, or a means of irradiation induction, after at least a part of the precursor is pigmented, when performing a concentration treatment, After the soluble pigment precursor and / or an organic substance having a specific structure or a functional group having an affinity for the (insoluble) pigment is present therein, the soluble precursor which has become an unstable system is pigmented. Even when concentrated, no precipitates or remarkable organic substances are present, and it is easy to produce a high-concentration solution of a soluble precursor partially converted into an insoluble pigment. It is possible to overcome the above problems caused by reduction.

[Brief description of the drawings]

[1] ¹ solidification coloring material obtained in Example of the present invention
H-NMR spectrum chart.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) C09B 67/20 C09B 67/20 F 67/46 67/46 C G02B 5/20 101 G02B 5/20 101 5 / 22 5/22 // B41M 5/00 B41M 5/00 E (72) Inventor Abul, Iqbal Switzerland, Alcon Seal 1732, Ladi 202 (72) Inventor Zimin, Hao Switzerland, Lichen 4125, Gstalte Nrainweg 75 (72) Inventor Toshio Yoshihara 1-1-1, Ichigaya-Kaga-cho, Shinjuku-ku, Tokyo Inside Dai Nippon Printing Co., Ltd. (72) Inventor Kiyoshi Ito 1-1-1-1, Ichigaga-cho, Shinjuku-ku, Tokyo No. Dai Nippon Printing Co., Ltd. (72) Inventor Kazuhiko Nakamura 1-1-1, Ichigaya Kagacho, Shinjuku-ku, Tokyo Dai Nippon Printing Co., Ltd. (72) Inventor River Minoru Chiba Prefecture Yotsukaido Utsukushigaoka 3-6-21 F-term (reference) 2H048 BB14 CA04 CA09 CA14 2H086 AA32 AA36 AA43

Claims (24)

[Claims] 1. A soluble pigment precursor which can be converted into an insoluble pigment, a solvent capable of dissolving the soluble pigment precursor, and a dispersibility of the insolubilized pigment in the solvent. By preparing a solution containing a stabilizer comprising an organic substance having a structure or a functional group capable of stabilizing the pigment, by converting the soluble pigment precursor into an insoluble pigment, the pigment insolubilized in the solvent is stably formed. A method for producing a coloring material, comprising obtaining a coloring material that is present in a dispersed state. 2. The method according to claim 1, further comprising the step of concentrating the obtained coloring material to obtain a solidified coloring material. 3. The method according to claim 2, further comprising a step of further dispersing the obtained solidified coloring material in a solvent. 4. The method according to claim 1, wherein the conversion of the soluble pigment precursor to an insoluble pigment is carried out by chemical means, thermal means, photolysis or irradiation-inducing means or a combination thereof. 5. The method according to claim 1, wherein the insoluble pigment has a polar group selected from the group consisting of a primary amine, a secondary amine, a cyclic amine, and a hydroxyl group. 6. The method according to claim 1, wherein the stabilizer is> CO, -NH₂,> N
H,> N-, = N⁺<, -CONH ₂, -CONH-,
-NHCOO-,> NCOO-, -NHCONH-,
(-NHCO)₂Selected from the group consisting of N- and -OH
2. The method of claim 1, wherein the group has a modified group. 7. The method of claim 1, wherein said stabilizer has an amine number. 8. The method according to claim 1, wherein the stabilizer has an amine value and an acid value, and the amine value is greater than the acid value. 9. The method according to claim 1, wherein the stabilizer is 1 to 230 mg KOH /
The method of claim 1 having an amine number of g. 10. The method according to claim 1, wherein said stabilizer has a urethane bond. 11. The method according to claim 1, wherein the stabilizer has a molecular weight of 20,000 or less. 12. The method according to claim 1, wherein said stabilizer has an average of 0.1 per molecule.
The method of claim 1, having from -20 to 20 reactive double bond groups. 13. A coloring material obtained by the method according to claim 1, which is used for a color filter. 14. An organic material having (1) an insoluble pigment obtained by conversion from a soluble pigment precursor and (2) a structure or a functional group capable of stabilizing the dispersibility of the insoluble pigment in a solvent. A coloring material comprising an adduct formed by interaction with a stabilizer comprising: 15. A coloring material comprising the adduct according to claim 14 dispersed in a solvent. 16. The method according to claim 16, wherein the insoluble pigment is a primary amine or a secondary amine.
The coloring material according to claim 14, having a polar group selected from the group consisting of a secondary amine, a cyclic amine, and a hydroxyl group. 17. The method according to claim 17, wherein the stabilizer is> CO, -NH₂,>
NH,> N-, = N⁺<, -CONH ₂, -CONH
-, -NHCOO-,> NCOO-, -NHCONH
-, (-NHCO)₂From the group consisting of N- and -OH
The coloring material according to claim 14, having a selected group. 18. The method according to claim 14, wherein said stabilizer has an amine number. 19. The coloring material according to claim 14, wherein the stabilizer has an amine value and an acid value, and the amine value is higher than the acid value. 20. The method according to claim 1, wherein the stabilizer is 1 to 230 mg KOH.
The coloring material according to claim 14, having an amine value of / g. 21. The coloring material according to claim 14, wherein the stabilizer has a urethane bond. 22. The coloring material according to claim 14, wherein the stabilizer has a molecular weight of 20,000 or less. 23. The method according to claim 20, wherein the stabilizer has an average of 0.1 per molecule.
15. The coloring material according to claim 14, having ~ 20 reactive double bond groups. 24. The method according to claim 1, which is used for a color filter.
4. A coloring material obtained by the method according to 4.