TWI411651B - Pigment dispersants and their use - Google Patents

Description

Pigment dispersant and its use

The present invention relates to a coloring composition for a color filter used for producing a pigment dispersant, a liquid crystal color display, an image pickup element, and the like, and a color filter using the same. More specifically, it is a coloring composition for a color filter excellent in pigment dispersibility, transparency, fluidity, and storage stability, and a color filter using the same.

The color filter used for liquid crystal display or the like is mainly a coloring composition in which a pigment is dispersed by a photoresist, and is applied to a substrate by a spin coating method, a coating method, or a transfer method, and then passed through a mask. It is manufactured by exposing light and energy lines to imaging. In the pigment portion forming the red pixel, a diketopyrrolopyrrole pigment is generally used. However, the pigment is dispersed only with a resin and a solvent in a general disperser because the dispersed pigment is not sufficiently dispersed. The dispersion liquid (in the case of "coloring composition for color filters") is used for the formation of color pixels of color filters (hereinafter referred to as "pixels"), and the resulting red pixels lack transparency. This pixel is a pigment for a color filter, and the transmittance is insufficient, and the red pigment is not sufficient as a pigment for a coloring composition for a color filter.

Further, the portion of the resin used for the photoresist is mainly used as a basic polymer having a high acid value because the aqueous alkaline solution can be used for the developing liquid of the pattern. Even in this case, the pigment dispersion liquid composed of the above-mentioned pigment and a high acid value basic resin causes aggregation of the pigment particles, and the viscosity of the pigment dispersion liquid tends to be high, and the pigment dispersion liquid tends to be sticky over time, often making The storage stability of the pigment dispersion is poor.

When the color filter is produced by using the pigment dispersion liquid having the above difficulties, the pigment dispersion liquid is applied to the substrate by spin coating and molding, and then the colored film is pixelized, but the viscosity of the pigment dispersion liquid When the pigment particles are agglomerated and the color filter exhibits thixotropic viscosity with the colored composition, the center portion of the coating layer before the pixelation is added to form a color filter for producing a large screen. Both the pixels formed in the central portion and the pixels formed in the peripheral portion cause color difference and concentration difference.

Therefore, the color filter is a coloring composition (pigment dispersion), and usually the pigment concentration is not limited to a high concentration range of 5 to 20 masses, so that the pigment particles do not aggregate between the dispersed states, and are generally dried or baked. The dry paint has a lower viscosity (for example, about 5 to 20 mPa.s) and is excellent in storage stability.

In order to satisfy the above requirements, in the case where the red pigment is a diketopyrrolopyrrole pigment (for example, CI Pigment Red 254), it has been revealed that the acid sulfation degree is 1 or more diketopyrrolopyrrole per molecule. A technique in which the acid is added to the above-mentioned pigment, and the pigment is treated with the acidic sulfate described above (Patent Document 1).

[Patent Document 1] JP-A-2000-160084 Bulletin

As described above, in the conventional production method described in Patent Document 1, it is difficult to control the coupling reaction, and the particle diameter of the produced pigment is not uniform, and a pigment having a relatively good quality cannot be obtained. Further, in the production method described in Non-Patent Document 1, the pigment productivity is low, and it is difficult to cope with industrial mass production.

In addition, the use of the liquid crystal display device has been expanded from the display of the personal computer to the color display of the color television, and the performance improvement of the color filter is also improved, and the transparency of the pixel is improved or the contrast of the transmitted light of the pixel is improved. The improvement, or the increase in the pigment concentration in the pixels, is necessary.

However, in the method of using the aforementioned acidic sulfate, it is desired to improve the transparency of the pixel by the improvement of the dispersibility of the pigment, or to avoid the increase in the viscosity of the pigment dispersion due to the increase in the concentration of the pigment, and the storage stability. The reduction is difficult, and further, it is difficult to control the reaction which occurs when the diketopyrrolopyrrole pigment is subjected to acidic sulfation, and the acidic sulfate which is introduced with an excessive amount of acidic sulfate group is used as a pigment dispersant. Foreign matter is generated in the pigment dispersion, and these problems need to be improved.

The inventors of the present invention have solved the aforementioned problems arising from the use of the above-mentioned acidic sulfated diketopyrrolopyrrole pigment for the use of a coloring composition for a color filter having a high pigment concentration, and to enhance the coloring composition for a color filter. The color grade, low viscosity and the possibility of avoiding the generation of foreign matter have been carefully studied. It has been found that an acid sulfated diketopyrrolopyrrole pigment composite having an acidic sulfuric acid group number of 0.05 to 0.5 can be used as a pigment dispersant to achieve color filter. The light sheet has a low viscosity of the coloring composition, and can prevent the gelation of the coloring composition during storage and prevent the occurrence of foreign matter, and at the same time, the transparency of the most important pixel as a color filter is also Can improve, and complete the invention of the case.

The foregoing objects are achieved by the following description. That is, the present invention provides a pigment dispersant characterized by containing a single component (a) described below or a component of the following (a) and the following component (b). In the case where the component (a) is used in combination with the component (b) below, the mass ratio of the component (a) to the component (b) is preferably a: b = 10: 90 to 90: 10.

(a) component: a pigment complex containing an acidic sulfonic acid group of a diketopyrrolopyrrole pigment and a diketopyrrolopyrrole pigment not containing an acidic sulfate group, and the acid sulfate group number of each diketopyrrolopyrrole pigment is 0.05 ~0.5.

(b) Component: A dye having a group other than the acidic sulfate group other than the above component (a), a metal salt thereof, an ammonium salt thereof or an amine salt thereof.

The component (b) is not particularly limited, but is a compound represented by the following general formula (I), general formula (II), general formula (III), and general formula (1V), a metal salt thereof, and ammonium thereof. Salts and/or their amine salts are preferred.

(wherein X ₁ is a hydrogen atom, a halogen atom, an alkyl group or a decylamino group; Y ₁ is a decylamino group, an anilino group, a benzylamino group or a phenoxy group; and these groups may further contain a halogen atom or an alkyl group on the substituent. Or a hydrazine amino group. R ₁ is a hydrogen atom, an alkyl group or a phenyl group, and R ₂ is an alkene group, a phenylene group or a naphthylene group, and these substituents are also preferred.

(wherein X ₁ is a hydrogen atom, a halogen atom or an alkyl group; R ₁ is a hydrogen atom; an alkyl group or a phenyl group; R ₂ is a phenyl group; or a naphthyl group, and these substituents are also preferred; k-based corresponding compounds The average number of acidic sulfate groups is 0.5 to 2 digits.)

(wherein R ₁ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an unsubstituted or substituted aromatic hydroxy group, an unsubstituted or substituted benzyl quinone imine group; and R ₂ is a hydrogen oxy group Atom and a hydroxyl group, R ₃ is a halogen atom, m represents an integer of 0 to 4, and n is an average number of introduced acidic sulfate groups of the corresponding compound, and is a number of 0.5 to 4.

(where A is or ; R ₁ and R ₂ represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, a carbonyl group, an acidic sulfate group, and a trifluoromethyl group; and R ₃ represents a hydrogen atom, a halogen atom, a hydroxyl group, and an alkyl group; ₄ , R ₅ , R ₆ and R ₇ represent a hydrogen atom, a halogen atom, a methyl group and a cyano group; M represents a hydrogen atom, a metal atom, an ammonium group and an amino group, and n represents an integer of 1 to 3. )

In the above pigment dispersant of the present invention, the diketopyrrolopyrrole pigment which does not contain an acidic sulfuric acid group is represented by the following general formula (V); and the acidic sulfate group of the diketopyrrolopyrrole pigment containing an acidic sulfate group, at least It is preferred to select one of a free acidic sulfate group, an acidic sulfate group metal salt, an amine salt, and an ammonium salt.

(wherein R ₁ and R ₂ are each independently and are a hydrogen atom, a halogen atom, a cyano group, an alkyl group or a phenyl group.)

Further, in the above pigment dispersant of the present invention, R ₂ of the general formula (I) is derived from taurine, N-methyl taurine, o-aminobenzenesulfonic acid, m-aminobenzenesulfonic acid, p-amino group. Benzenesulfonic acid, 4-chloroaniline-3-sulfonic acid, 2-p-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-methoxyaniline-5-sulfonic acid, P- Methoxyaniline-5-sulfonic acid, o-toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, P-toluidine-2-sulfonic acid, 2-chloro-P-toluidine-3 -sulfonic acid, 3-amino-6-chloro-4-o-sulfobenzoic acid, 1-amino-8-naphthalenesulfonic acid, 2-amino-1-naphthalenesulfonic acid, 5-amino-1-naphthalenesulfonic acid, The amine selected from 6-amino-1-naphthalenesulfonic acid and 5-amino-3-naphthalenesulfonic acid is preferably a group which removes an amino group.

Further, in the above pigment dispersant of the present invention, R _{2 of the} general formula (II) is aniline, N-methylaniline, toluidine (o-, m- or p-), methoxyaniline (o-, M- or p-), chloroaniline (o-, m- or p-), aniline, 1-naphthylamine, and an alternative amine of 2-cetanamine, the amino group is preferably removed, and the present invention is A coloring composition for a color filter characterized by containing a red pigment and the above-described pigment dispersant of the present invention and a resin dispersant and a resin varnish is provided. The red pigment is CI Pigment Red 254; and the resin dispersant is preferably a cationic resin dispersant.

Further, in the method for producing a color filter in which a color pixel is formed on a substrate including a color filter, the colored pixel is formed using the coloring composition for a color filter of the present invention. A method of manufacturing a color filter, a color filter manufactured by the method, an image display device including the color filter, and an information transmission device including the image display device.

According to the above aspect of the invention, by using a specific pigment dispersant as a pigment dispersant for a colored composition for forming a red pixel of a color filter, it is possible to produce a stable coloring composition for a color filter and to avoid foreign matter. Occurs, and finally, in the use of the coloring composition for color filters, it has excellent spectral characteristics, clear and vivid, high transparency, light resistance, heat resistance, solvent resistance, chemical resistance, and Color filters such as water resistance and excellent quality and excellent pixel quality.

Hereinafter, the best mode for carrying out the invention of the present invention will be described, and the present invention will be described in more detail. The pigment dispersant of the present invention comprises the above-mentioned single (a) component or the component (a) and the aforementioned component (b).

The component (a) is a pigment complex containing an acidic sulphate-based diketopyrrolopyrrole pigment and a diketopyrrolopyrrole pigment not containing an acidic sulfate group, wherein the acid sulfhydryl group of each diketopyrrolopyrrole pigment is 0.05. ~0.5 pigment composite.

An example of the preparation method of the component (a) is a diketopyrrolopyrrole pigment which does not contain an acidic sulfate group as shown in the following general formula (V), and for example, CI Pigment Red 254 is subjected to an acidic sulfating agent such as fuming sulfuric acid. At the time of acidic sulfation, the acidic sulfation conditions are adjusted, and the number of acidic sulfuric acid groups introduced into the diketopyrrolopyrrole pigment is controlled within the above range.

(wherein R ₁ and R ₂ are each independently and are a hydrogen atom, a halogen atom, a cyano group, an alkyl group or a phenyl group.)

In the case where the number of acidic sulfate groups of one molecule of the acidic sulfate is more than 0.5, the diketopyrrolopyrrole pigment which is not subjected to acid sulfated in the range of 0.05 to 0,5 of the average acidic sulfate group is used. The desired acid dispersant is obtained by mixing with the acidic sulfuric acid, dissolving the mixture in concentrated sulfuric acid, injecting the solution into ice water, precipitating the composite, rinsing with water, and drying.

The number of acidic sulfate groups is adjusted to a complex of 0.05 to 0.5, and the affinity or solubility to water or a solvent is remarkably lowered, indicating that the pigment formed is substantially insoluble or poorly soluble. The unacidified sulfated diketopyrrolopyrrole pigment molecule added to the acid sulfated diketopyrrolopyrrole pigment molecule recombines (eutectic or mixed) the acidic sulfated diketopyrrolopyrrole molecule. The affinity or solubility of the diketopyrrolopyrrole molecule which results in acid sulfation is reduced.

The acidic sulfate group of the diketopyrrolopyrrole pigment composite may be a radical or a salt with a salt. Examples of the metal forming the salt include basic metals such as Li, Na, and K; and polyvalent metals such as Ca, Ba, Al, Mn, Sr, Mg, and Ni. Further, examples of the ammonia forming the amine salt or the ammonium salt include (mono, bis or tri) alkylamines, substituted or unsubstituted olefin nitriles, Alkanolamines, alkylamine salts, chlorides, and the like.

The component (b) is a dye having an acidic sulfuric acid group other than the above component (a), a metal salt thereof, an ammonium salt thereof or an amine salt thereof. For example, it is known that such a pigment may be any component, but component (b) The compound represented by the above general formula (I), general formula (II), general formula (III) and general formula (IV) is preferably a metal salt, an ammonium salt and/or an amine salt.

The compound represented by the above general formula (I) can be obtained by substituting a substituent 1 - anthracene 1 mole, with a substitutable aniline or a substituted phenol or a substituent 1 - amidoxime All of them are 1 mol, and the salted melamine chloride 1 mol, in the inactive solvent such as o-dichlorobenzene, the reaction is carried out at 130 ° C ~ 170 ° C for 2-6 hours, and then there will be one The acidic sulfuric acid-based aliphatic amine or aromatic amine is obtained by reacting 1 mole at 150 ° C to 170 ° C for 3 to 4 hours.

An aliphatic amine or an aromatic amine having an acidic sulfuric acid group used in the compound of the above general formula (I), for example, taurine, N-methyltaurine, o-aminobenzenesulfonic acid , m-aminobenzenesulfonic acid, p-aminobenzenesulfonic acid, 4-chloroaniline-3-sulfonic acid, 2-p-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-methoxy Aniline-5-sulfonic acid, p-methoxyaniline-5-sulfonic acid, o-toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, 2-Chloro-p-toluidine-3-sulfonic acid, 3-Ammonia-6-chloro-4-o-sulfobenzoic acid, 1-Ammonia-8-caesulfonic acid, 2-Ammonia-1-caesulfonic acid, 5-Ammonia 1-Naphthalenesulfonic acid, 6-Ammonia- 1 -Cetanesulfonic acid, and 5-Ammonia-3-caesulfonic acid.

Further, the compound represented by the above general formula (II) can be obtained by using a substituent 1 - anthracene 2 mole, and a cyanuric chloride 1 mol, o-dichlorobenzene or the like. In the active solvent, the reaction is carried out at 130 ° C to 170 ° C for 2 to 6 hours, and further, an aromatic amine 1 mol containing no acidic sulfuric acid group is added, and the reaction is carried out at 150 ° C to 170 ° C for 3 to 4 hours, the second, The product is obtained by acid sulfating the acidic sulfating agent such as fuming sulfuric acid.

Examples of the aromatic amine used in the production of the compound of the above general formula (II) include aniline, N-methylaniline, toluidine (o-, m- or p-), and methoxyaniline (o- , m- or p-), chloroaniline (o-, m- or p-), phenylaniline, 1-naphthylamine and 2-caiamine.

The compound represented by the above general formula (III) is a quinacridone compound which can be easily synthesized from anhydrous phthalic acid which may have a substituent and a quinidine which may have a substituent, such as fuming sulfuric acid, etc. The acidic sulfating agent is obtained by acid sulfation.

R ₁ of the above general formula (III) is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, an unsubstituted or substituted aromatic hydroxy group, an unsubstituted or substituted quinone imine group; ₂ is a hydrogen atom or a hydroxyl group; R ₃ is a halogen atom, m is an integer of 0 to 4; n is an average number of introduced acidic sulfate groups of the compound, and is a number of 0.5 to 4. The aforementioned alkyl group represents a linear or branched carbon of a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a t-butyl group or the like. An alkyl group having an alkyl group of about 1 to 8 and an aromatic hydroxy group, which is an aromatic hydrocarbon group such as a phenyl group, a phenyl group, a biphenyl group, a fluorenyl group or a phenanthryl group, which may be unsubstituted or substituted. . The substituent is, for example, a halogen atom, a hydroxyl group or an alkyl group, and is not particularly limited.

The compound represented by the above general formula (IV) may be a 1,4-benzene having a substituent at a 2,5-position by an acid chloride of a 3-hydroxy-2-naphthoic acid which may have a substituent a diamine or a benzidine having a 3,3'-position substituent, which is reacted at 130 to 135 ° C in an inert solvent such as nitrobenzene; secondly, a sulfamic acid which may have a substituent and may have The aniline of the substituent is separately diazotized according to a conventional method, and is obtained by coupling.

In addition, examples of the compound represented by the above general formula (I) to general formula (IV) and the metal forming the metal salt include basic metals such as Li, Na, and K, and Ca, Ba, Al, and Mn. A polyvalent metal such as Sr, Mg or Ni. Further, examples of the compound represented by the general formula (I) to the general formula (IV) and the amine forming the amine salt include, for example, (mono, di(di) or tri(tri))alkylamines. Alternate or unsubstituted olefin nitramines, alkanolamines, alkylamine salt chlorides, and the like.

The component (a) may be used singly as a pigment dispersant, and the component (a) may be used in combination with the compound represented by any one of the general formula (I) to the general formula (IV) (component (b)). . The mass ratio of the component (a) to the component (b) in the case where the component (a) and the component (b) are used in combination is (a) component: (b) component = 10: 90 to 90: 10, and 40: 60. ~60:40 is suitable. When the amount of the component (a) is outside the above range, the viscosity of the dispersion is weakened and insufficient, and further, the stability of the dispersion is also weakened.

The coloring composition for a color filter of the present invention is composed of a pigment, the above-described pigment dispersant, a resin dispersant (a pigment dispersant for pigment dispersion composed of a polymer compound), and a resin varnish. The pigment used in the present invention includes a diketopyrrolopyrrole pigment as a red pigment. Such red pigments include C.I. Pigment Red 254 and the like. Among them, as a color correction, a yellow pigment may be blended and dispersed. As such a yellow pigment, isoindoline pigment (C.I. yellow pigment-139) or the like can be used. The amount of the red pigment to be used is not particularly limited, and is usually used in a ratio of 5 to 500 parts by mass based on 100 parts by mass of the resin binder of the resin paint to be described later.

The pigment blending ratio of the pigment dispersant is preferably from 0.05 to 40 parts by mass, more preferably from 0.1 to 10 parts by mass, based on 100 parts by mass of the pigment. If the blending ratio of the pigment dispersant is too low, the effect of the intended pigment dispersant cannot be reliably achieved. Further, if the blending ratio of the pigment dispersant is too low, the desired effect cannot be obtained. On the other hand, if the blending ratio of the pigment dispersant is too high, the physical properties of the colored filter for the colored filter are lowered. Moreover, the color of the pigment dispersant itself causes a large change in the hue of the pigment due to dispersion.

As the resin dispersant used in the present invention, a known dispersant can be used, and in particular, a cationic resin dispersant is preferred. Cationic resin dispersant, including, for example, BYK-Chemie Gmbh (Germany) trade name: DISPERBYK-160, same 161, same 162, same 163, same 164, same 166, same 171, same 182, same 184, same 9000 Same as 2001, same 2070, same 2150; EFKA (Netherlands) trade name: EFKA-44, same 46, same 47, same 48, same 4010, same 4050, same 4055, same 4020, same 4015, same 4060, same 4300, same as 4330, same 4400, same 4406, same 4510, same 4800; Avecia LUKk (UK) trade name: SOI.SPERS-24000, same 32550.NI 3Z-4204/10; Chuanyan Fine Chemical Company's trade name :HINOACT T-6000, the same 7000, the same 8000; Ajinomoto company's trade name: AJISPUR-PB-821, the same 822, the same 823; Gongrongshe Chemical Co., Ltd. trade name: FLORENE DOPA-17HF, with 15BHF, the same 33, with 44 and so on.

The amount of the resin dispersant to be used in the present invention is not particularly limited, but is preferably 2 to 100 parts by mass, and more preferably 10 to 50 parts by mass. When the addition of the resin dispersant is less than 2 parts by mass, good pigment dispersion stability cannot be obtained, and if it is more than 100 parts by mass, the development of the film formed by the coloring composition obtained by the color filter will be produced. Bad situation.

In the resin varnish used as the dispersion medium for dispersing the pigment in the present invention, a known resin varnish which is conventionally used for the coloring composition for a color filter can be used, and is not particularly limited. Further, as the resin varnish for the dispersion medium, a suitable solvent or an aqueous medium can be used. Further, it is also possible to add conventional additives such as a dispersing aid, a smoothing agent, and a tackifier as appropriate.

Among them, a photosensitive resin paint and a non-photosensitive resin paint can be used for the resin paint. The photosensitive resin varnish may, for example, be a photosensitive resin varnish used in an ultraviolet curable ink or an electron beam hardening ink, and a non-photosensitive resin varnish may, for example, be a relief ink, a lithographic ink, or a gravure ink. Resin paint used in printing inks such as stencil screen inks, resin lacquers used in inkjet printing, resin lacquers used in electrodeposition coating, resins used in electronic printing or xerographic imaging agents Paint, heat transfer film or resin paint used in the belt.

Specific examples of the photosensitive resin varnish include a photosensitive carbonized rubber-based resin, a photosensitive phenol-based resin, a photosensitive sodium polyacrylate-based resin, a photosensitive polyamido resin, and a photosensitive polyimide. Further, the resin or the like further includes an unsaturated polyester resin, a polyester acrylate resin, a propylene oxide acrylate resin, a urethane acrylate resin, a polyester acrylate resin, and a polyol acrylate system. A lacquer such as a resin, or a lacquer as a reactive diluent monomer is further added to the lacquer. Among the above-mentioned photosensitive resin varnishes, a suitable resin is preferably an alkali-developable acrylate-based resin containing a free carboxyl group in its molecule.

Specific examples of the non-photosensitive resin varnish include, for example, a cellulose acetate resin, a nitrocellulose resin, a styrene (co)polymer, a polyvinyl butyral resin, and an aminoalkyd system. Resin, polyester resin, ammonia resin modified polyester resin, polyurethane resin, basic polyol ester resin, soluble polyamine resin, soluble polyamidiene resin, soluble polyamidoximine Resin, soluble polyester sulfimide resin, hydroxyethylecellulose, water-soluble salt of styrene-maleate copolymer, (meth)aloate (co)polymer The water-soluble salt, the water-soluble amino polyester resin, and the water-soluble polyamine resin may be used singly or in combination of two or more.

The method for producing the colored composition of the above-described respective components of the present invention is not particularly limited, and examples thereof include a method in which a pigment and a pigment dispersant are dissolved in sulfuric acid or the like, and then injected. In the water, the two were made into a solid solution, and together with the cationic resin dispersant, a resin paint was added and kneaded.

(2) uniformly suspending the pigment in water or an organic solvent, adding a solution containing a pigment dispersant to the suspension, and adding the pigment dispersing agent on the surface of the pigment particle together with the cationic resin dispersing agent The resin paint is kneaded.

(3) The pigment, the pigment dispersant, and the cationic resin dispersant are finely dispersed in a wet media disperser of an attritor or a ball mill, and kneaded by adding a resin varnish.

(4) The pigment, the pigment dispersant, and the cationic resin dispersant are added to the resin varnish in advance mixing, and are subjected to dispersion treatment by a wet medium disperser.

In the case of using a colored composition of the present invention, in the case of using a resin varnish as a photosensitive resin varnish, a conventional photopolymerization initiator such as benzoin ethyl ether or benzophenone is added to the composition. Kneading was carried out in a manner known in the art to prepare a photosensitive coloring composition for use. Further, a thermal polymerization initiator may be used instead of the photopolymerization initiator described above as a thermally polymerizable coloring composition.

In the case where the above-described photosensitive coloring composition is used to form a pixel of a color filter on a substrate, the photosensitive coloring composition on the transparent substrate is, for example, a spin coater or a low speed spin coater. , roller coating machine or doctor blade coating machine for full coating, or a variety of printing methods to select a suitable method for full printing, or a little more than a little bit of printing, ready to dry after the mask The coated surface of the transparent substrate is adhered to the printed surface, and an ultrahigh pressure mercury lamp is used for exposure and baking of the pixels. Next, the development and the cleaning are performed, and the post-baking is performed as necessary to form a pixel. The above-described pixel forming method itself is well known. In the present invention, the pixel forming method of the color filter is not particularly limited.

In the case of forming a color filter pixel by using the coloring composition (non-photosensitive coloring composition) of the present invention using a non-photosensitive resin paint, the non-photosensitive coloring composition on the transparent substrate is colored, for example, The filter is printed by a suitable method selected from the above various printing methods in the printing ink, and the method of forming a pixel on the direct substrate and the electrodeposition coating method in the aqueous electrodeposition coating composition are applied to form on the substrate. The method of the pixel, the inkjet ink, the inkjet printing method, the method of forming a pixel on the substrate, the electronic printing method, or the electrostatic printing method, or the transfer from the above-described manner, etc. A substrate, a method of transferring onto a substrate for a color filter once a pixel is formed, and the like. Next, according to the conventional method, baking is carried out as needed, and the surface is smoothed by polishing to perform surface protection. Furthermore, according to the conventional practice, a black frame is formed. In this way, a color filter containing each pixel of RGB can be obtained. The method for producing such a color filter is known per se. In the present invention, the method of producing the color filter is not particularly limited.

The synthesis examples, examples, and comparative examples are set forth below to further illustrate the present invention.

In addition, the "parts" and "%" in the text are quality benchmarks.

[Synthesis Example A1] 30 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254) was added to 300 parts of 20% fuming sulfuric acid, followed by reaction at 60 to 65 ° C for 6 hours, and after cooling, the reaction mixture was 3000. The ice water of the part was precipitated, filtered, and rinsed with water to obtain 110 pieces of water (28 parts pure). After the slurry was dried, 28 parts of the diketopyrrolopyrrole (pigment dispersant A1) having an average of 0.8 acidic sulfate groups per molecule was obtained, as a result of elemental analysis of sulfur.

Further, five parts of the pigment dispersant A1 and five parts of C.I. Pigment Red 254 were added to 100 parts of 95% concentrated sulfuric acid, and the mixture was stirred at room temperature for 1 hour. After cooling, the obtained concentrated sulfuric acid solution was poured into 1000 parts of ice water to precipitate a composite, which was filtered and rinsed with water to obtain 39 parts of water slurry (10 parts in pure amount). After the water slurry was dried, 10 parts of the diketopyrrolopyrrole (pigment dispersant A2) having an average of 0.4 acidic sulfate groups per molecule was obtained as a result of elemental analysis of sulfur.

[Synthesis Example A2] 3.75 parts of the pigment dispersant A1 of Synthesis Example A1 and 6,25 parts of C.I. Pigment Red 254 were added to 100 parts of 95% concentrated sulfuric acid, and the mixture was stirred at room temperature for 1 hour. After cooling, the obtained concentrated sulfuric acid solution was poured into 1000 parts of ice water to precipitate a composite, which was filtered and rinsed with water to obtain 39 parts of water slurry (10 parts in pure amount). After the water slurry was dried, 10 parts of the diketopyrrolopyrrole (pigment dispersant A3) having an average of 0.3 acidic sulfate groups per molecule was obtained as a result of elemental analysis of sulfur.

[Synthesis Example A3] Using the pigment dispersant A1 of the synthesis example A1 of 2.5 parts and the CI pigment red 254 of 7.5 parts, according to the result of elemental analysis of sulfur, the average of each molecule was obtained in the same manner as in the synthesis example A2. 10 parts of diketopyrrolopyrrole (pigment dispersant A4) to which 0.2 acidic sulfate groups were introduced.

[Synthesis Example A4] 30 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254) was added to 300 parts of 20% fuming sulfuric acid, and the reaction was carried out at 45 to 50 ° C for 6 hours. After cooling, the reaction mixture was allowed to react. 3,000 parts of ice water were precipitated, filtered, and rinsed with water to obtain 110 pieces of water slurry (28 parts in pure amount). After the slurry was dried, 28 parts of the diketopyrrolopyrrole (pigment dispersant A5) having an average of 0.4 acidic sulfate groups per molecule was obtained as a result of elemental analysis of sulfur.

[Example A1] A propylene-based resin varnish (methacrylic acid/butyl acrylate/styrene/hydrogen oxyhydroxide) having a molar ratio of 25/50/15/10 molar ratio, molecular weight 12,000, solid 50 parts of 30%), 20 parts of CI Pigment Red 254, 4 parts of isoindoline yellow pigment (CI yellow pigment 139), 1 part of pigment dispersant A2 obtained in Synthesis Example A1, and cationic resin dispersant ( DISPER-BYK-2000) 4 parts and solvent (propylene glycol monomethyl ether acetate) (hereinafter referred to as PGMAc) 20 parts, after premixing, dispersion by a horizontal bead mill to obtain a red color composition Things.

[Examples A2 to A4] The pigment dispersant A2 of Example A1 was replaced with the pigment dispersants A3 to A5 obtained in each of Synthesis Examples A2 to A4, and the red colored composition was obtained in the same manner as in Example A1. .

[Comparative Example A1] The pigment dispersant A2 of Example A1 was replaced with the pigment dispersant A1 obtained in Synthesis Example A1 to obtain a red colored composition similar to that of Example A1.

The fluidity and color development surface of the colored compositions of the above Examples A1 to A4 were compared with each other in terms of gloss and foreign matter occurrence, and the case of Comparative Example A1. The fluidity of each coloring composition and the gloss of the color development were measured according to the following method, and the presence or absence of foreign matter was observed according to the method described below. The coloring compositions of Examples A1 to A4 were placed at room temperature for one month, and the observation results measured before and after storage were compared with those of Comparative Example A1.

Flowability: An E-type viscometer was used, and each coloring composition was measured at room temperature (25 ° C) and the number of revolutions of the rotor was 6 rpm.

Gloss: A bar coater (winding line thickness: 0.45 mm) was used, and each of the coloring compositions was developed in a polypropylene film, and the gloss of the color surface was compared by visual inspection and gloss. In addition, the high gloss gives a good evaluation, and the comparison result is expressed by the following evaluation index.

○: Good △: still OK ×: bad

Foreign matter observation: Each colored composition was applied to a glass substrate by a spinner and dried at 90 ° C for 2 minutes. After the film formation, the presence or absence of foreign matter on the film was observed at 200 times with a microscope film, and the results were observed according to the following. The evaluation indicators indicate this.

○: no foreign matter △: slightly foreign matter ×: completely foreign matter

The above measurements and the results of the evaluation are shown in Table A1.

As can be clearly seen from Table A1, the color composition of Examples A1 to A4 using the pigment dispersants A2 to A5 was compared with the composition of Comparative Example A1 using the pigment dispersant A1, and the viscosity after storage (1) After a month, it is low, and the gloss is also good. No foreign matter occurs before or after storage, and it has excellent properties as a coloring composition.

[Reference Example A1] 50 parts of the same type of propylene-based resin varnish used in Example A1, brominated chlorine-containing phthalocyanine green pigment (C.1, green pigment 36), 17 parts, quinoxaline 13 parts of ketone yellow pigment (CI yellow pigment 138), 9 parts of monoacid sulfated quinacridone yellow as pigment dispersant, 4 parts of cationic resin dispersant (DISPER-BYK-2000) and PGMAc20, premixed Thereafter, it was dispersed by a horizontal bead mill to obtain a green colored composition.

[Reference Example A2] 50 parts of the same type of propylene-based resin varnish used in Example A1, 16 pieces of ε-type copper phthalocyanine blue pigment (C.1, blue pigment 15:6), ring 4 parts of oxyhexane violet pigment (CI violet pigment 23), 2 parts of monoacid sulfated phthalocyanine blue as pigment dispersant, 1 part of monoacid sulfated indanthrone, and cationic resin dispersant (DISPER-BYK) -2000) Four parts and PGMAc 20 parts were combined, and after premixing, they were dispersed by a horizontal bead mill to obtain a blue colored composition.

[Example A5] For the production of RGB color filters, the color compositions of R, G and B were obtained in accordance with the formulation of Table A2 below.

The glass substrate subjected to the decane coupling agent treatment was placed in a spin coater, and the colored composition of R of Table A2 was spin-coated at 300 rpm for 5 seconds and then at 1,200 rpm for 5 seconds. Subsequently, prebaking at 80 ° C for 10 minutes was carried out, and a mask having a pixel state in a mosaic state was adhered to the pre-copied film, and exposure was performed at a light amount of 100 mJ/cm ² using an ultrahigh pressure mercury lamp. Next, development and cleaning were carried out using a dedicated developing solution and a special lotion to form a red mosaic pixel on the glass substrate. Finally, using the color composition of G and B of Table A2, coating and baking are performed according to the above method to form a green mosaic pixel and a blue mosaic pixel, and color filters having RGB pixels are taken. sheet. The obtained color filter has excellent spectral characteristics and excellent fastness such as light resistance and heat resistance of each pixel, and further exhibits color filter for liquid crystal color display in light transmission. The excellent properties of the film.

[Synthesis Example B1] 72 parts of 1-aminoguanidine and 30 parts of salted melamine chloride were added to 1000 parts of nitrobenzene, and the mixture was stirred at 170 ° C for 5 hours. After cooling, 41 parts of taurine and 23 parts of potassium carbonate were added, and the mixture was stirred at 180 ° C for 8 hours. After cooling, the precipitate was filtered, washed with ethanol, and then degummed in water to make it acidic with hydrochloric acid. The precipitate was collected, concentrated, washed with water, and dried to obtain the following compound B1, 94.

[Synthesis Example B2] 72 parts of 1-aminoguanidine and 30 parts of salted melamine chloride were added to 1000 parts of nitrobenzene, and the mixture was stirred at 170 ° C for 5 hours. After cooling, 56 portions of taurine and 23 parts of potassium carbonate were added, and the mixture was stirred at 180 ° C for 12 hours. After cooling, the precipitate was filtered, washed with ethanol, and then degummed in water to make it acidic with hydrochloric acid. The precipitate was collected, concentrated, washed with water, and dried to obtain the following compound B2, 101.

[Synthesis Example B3] To a portion of the o-dichlorobenzene 1000, 73 parts of 1-aminoguanidine and 30 parts of salted melamine chloride were added, and the mixture was stirred at 170 ° C for 5 hours. After cooling, 35 parts of o-toluidine was added and stirred at 180 ° C for 5 hours. After cooling, it was filtered, washed with ethanol, washed with water and dried to obtain 4-bis(1-ammonium)-6-tolylamino-1,3,5-trim. Next, 94 parts of the compound were taken, and 800 parts of 5% fuming sulfuric acid having a temperature of 10 ° C or less was added, followed by a reaction at 30 ° C for 5 hours. After cooling, the reaction mixture was precipitated in 2500 parts of ice water, filtered, and washed with water. According to the elemental analysis of sulfur, an average of 0.9 acidic sulfate groups per molecule were obtained and introduced into the following compound R3, 102. unit.

[Example B1] A propylene-based resin varnish (methacrylic acid/butyl acrylate/styrene/hydrogen oxyhydroxide) having a molar ratio of 25/50/15/10 molar ratio, molecular weight 12,000, solid 50 parts) 30 parts, 4 parts of CI Pigment Red 254, 20 parts, isoindoline yellow pigment (CI yellow pigment 139), compound R1 obtained in Synthesis Example B1, 1 part, and pigment dispersant obtained in the former Synthesis Example A4 A5, one part, four parts of the cationic resin dispersing agent (DISPER-BYK-2000) and the PGMAc20 part were blended, and after premixing, it was dispersed by the horizontal bead mill to obtain a red colored composition.

[Example B2] Compound B1 was replaced with Compound B2 of Synthesis Example B2, and the same procedure as in Example B1 was carried out to obtain a red colored composition.

[Example B3] Compound B1 was replaced with Compound B3 of Synthesis Example B3, and the same procedure as in Example B1 was carried out to obtain a red colored composition.

[Comparative Example B1] A pigment-dispersant A5 was not used, and except that only the compound B1 was used, the same procedure as in Example B1 was carried out, and a red colored composition was obtained.

[Comparative Example B2] A pigment-dispersant A5 was not used, and except that only the compound B2 was used, the same procedure as in Example B1 was carried out, and a red colored composition was obtained.

[Comparative Example B1] A pigment-dispersing agent A5 was not used, and except that only the compound B3 was used, the same procedure as in Example B3 was carried out, and a red colored composition was obtained.

The fluidity of the color composition of the above Examples B1 to B3 and the gloss of the color development surface were compared with those of Comparative Examples R1 to B3. The fluidity of each coloring composition and the gloss of the color-developing surface (after storage for one month) were measured in the same manner as described above, and the relative evaluation was carried out in the same manner as in the above-described manner and in Comparative Examples R1 to B3. The above measurement and evaluation results are shown in Table B1.

As is clear from Table B1, the coloring compositions of Examples B1 to B3 in which Compounds B1 to B3 and Pigment Dispersant A5 were used in combination were compared with the compositions of Comparative Examples B1 to B3 in which Compounds B1 to B3 were used alone. The viscosity before storage and after storage (after 1 month) is low, the gloss is also good, and it has excellent properties as a coloring composition.

[Example B4] In order to produce a color filter of RGB, coloring compositions of R, G, and B were obtained in accordance with the formulation of Table B2 below.

In the same manner as in the embodiment A5, a color filter having RGB pixels was prepared.

The obtained color filter has excellent spectral characteristics, excellent light resistance, heat resistance, and the like, and is excellent in light transmittance, and exhibits excellent properties as a color filter for liquid crystal color display.

[Synthesis Example C1] 50 parts of tetrachloroquinophthalone was added to 20 parts of 20% fuming sulfuric acid, and then the reaction was carried out at 80 ° C for 6 hours. After cooling, the reaction mixture was precipitated in 2,000 parts of ice water. The mixture was filtered and rinsed with water to obtain 280 parts of a water slurry of the following compound C1 (purity: 55 parts). After the slurry was dried, according to the result of elemental analysis of sulfur, an average of 1.3 acidic C sulfate-introduced compounds C1 per molecule of 55 were obtained.

[Synthesis Example C2] 90 parts of a water slurry of the compound C1 of Synthesis Example C1 (a pure amount of 18 parts) was added to 240 parts of water, followed by stirring at 25 ° C for 1 hour, and the precipitate was filtered and rinsed with water, and dried. The following compound C2 of 17 parts was obtained.

[Synthesis Example C3] Except that 50 parts of CIPigment Yellow 138 were used instead of 50 parts of tetrakiquilonone, the same operation as in the synthesis example c.1 was carried out, and the result of elemental analysis of sulfur was obtained to obtain 56. On average, 0.9 molecules of the following acidic acid groups were introduced into the following compound C3.

[Synthesis Example C4] The same operation method as in Synthesis Example C2 was carried out except that 90 parts of the water slurry of the compound C3 of the synthesis example C3 was used instead of 90 parts of the water slurry of the compound C1 of the synthesis example C1, to obtain 18 parts. The following compound C4.

[Example C1] A propylene-based resin varnish (methacrylic acid/butyl acrylate/styrene/hydrogen oxyhydroxide) having a molar ratio of 25/50/15/10 molar ratio, molecular weight 12,000, solid 50 parts) 30 parts, 20 parts of CI Pigment Red 254, 4 parts of isoindoline yellow pigment (CI yellow pigment 139), and 1 part of the pigment dispersant C1 obtained in Synthesis Example C1, in the above Synthesis Example A4 One part of the obtained pigment dispersant A5, four parts of the cationic resin dispersing agent (AJISPUR-P13-821) and the PCMAc 20 part were blended, and after premixing, it was dispersed by the horizontal bead mill to obtain a red colored composition.

[Example C2] A red colored composition was obtained in the same manner as in Example C1 except that Compound C2 of Synthesis Example C2 was used instead of Compound C1.

[Example C3] A red colored composition was obtained in the same manner as in Example C1 except that Compound C3 of Synthesis Example C3 was used instead of Compound C1.

[Example C4] A red colored composition was obtained in the same manner as in Example C1 except that the compound C4 of the compound of Example C4 was used instead of the compound C1.

[Comparative Example C1] A red colored composition was obtained in the same manner as in Example C1 except that the pigment dispersant A5 was not used.

[Comparative Example C2] A red colored composition was obtained in the same manner as in Example C1 except that the pigment dispersant A5 was not used.

[Comparative Example C3] A red colored composition was obtained in the same manner as in Example C1 except that the pigment dispersant A5 was not used.

[Comparative Example C4] A red colored composition was obtained in the same manner as in Example C1 except that the pigment dispersant A5 was not used.

The fluidity of the color composition of the above Examples C1 to C4 and the gloss of the color development surface were compared with those of Comparative Examples C1 to C4. The fluidity of each coloring composition and the gloss of the color development surface (after storage for one month) were measured in the same manner as described above, and the relative evaluation was carried out in the same manner as described above and in the cases of Comparative Examples C1 to C4. The above measurement and evaluation results are shown in Table C1.

As is clear from Table C1, the coloring compositions of Examples C1 to C4 in which Compounds C1 to C4 and Pigment Dispersant A5 were used in combination with the compositions of Comparative Examples C1 to C4 in which Compounds C1 to C4 were used alone were compared. The viscosity before storage and after storage (after 1 month) is low, and the gloss is also good, and it has excellent properties as a coloring composition.

[Example C5] In order to produce a color filter of RGB, the coloring compositions of R, G, and B were obtained in accordance with the formulation of Table C2 below.

In the same manner as in the embodiment A5, a color filter having RGB pixels was prepared.

The obtained color filter has excellent spectral characteristics, excellent light resistance, heat resistance, and the like, and is excellent in light transmittance, and exhibits excellent properties as a color filter for liquid crystal color display.

[Synthesis Example D1] According to the conventional method, 60 parts of 3-hydroxy-2-carboxylic acid were taken, and in the nitrobenzene 400 part, sulfonium chloride was used for 40 parts of thiocyanine chloride, and 2,5-dichloro- 1 was added. 25 parts of 1,4-phenylenediamine was heated at 130 to 135 ° C for 5 hours. After cooling, 200 parts of methanol was added, and after purification, the precipitated methanol was filtered, and the mixture was washed with water and dried, and then 60 parts of the reaction product were obtained. Among the 10 parts, 100 parts of methanol, 3 parts of sodium hydroxide, 3 parts of sodium citrate and 11 parts of the substance were added as a bottom liquid. Take 3.5 parts of p-aminobenzenesulfonic acid and diazotize according to the conventional method. Coupling is carried out in the above-mentioned bottoming liquid. After 1 hour, 4.3 parts of 2-chloro-5-trifluoromethylaniline (trifluoromethylaniline) are used. After diazotization, after the coupling, according to the elemental analysis of sulfur, 11 kinds of the following compounds D1 in which one acidic sulfate group was introduced per molecule were obtained.

[Synthesis Example D2] 35 parts of 3,3'-dichlorobenzene was used instead of 25 parts of 2,5-dichloro-1,4-phenylenediamine of Synthesis Example D1, and the other method was the same as in Synthesis Example D1. As a result of the elemental analysis of the sulfur, the following compound D2 in which one acidic sulfuric acid group was introduced per molecule on average was obtained.

[Example D1] A propylene-based resin varnish (methacrylic acid/butyl acrylate/styrene/hydrogen oxyhydroxide) having a molar ratio of 25/50/15/10 molar ratio, molecular weight 12,000, solid 50 parts of 30%), 20 parts of diketopyrrolopyrrole pigment (CI Pigment Red 254), 4 parts of isoindoline yellow pigment (CI yellow pigment 139), and 1 part of compound D1 obtained in Synthesis Example D1, One part of the pigment dispersant A5 obtained in Synthesis Example A4, four parts of a cationic resin dispersant (SOLSPERS-24000) and a PCMAc 20 part were mixed, and after premixing, it was dispersed by a horizontal bead mill to obtain a red color. Composition.

[Example D2] A red colored composition was obtained in the same manner as in Example D1 except that Compound D2 of Synthesis Example D2 was used instead of Compound D1.

[Comparative Example D1] A red colored composition was obtained in the same manner as in Example D1 except that the pigment dispersant A5 was not used.

[Comparative Example D2] A red colored composition was obtained in the same manner as in Example D1 except that the pigment dispersant A5 was not used.

The fluidity of the color composition of the above Examples D1 to D4 and the gloss of the color development surface were compared with those of Comparative Examples D1 to D4. The fluidity of each coloring composition and the gloss of the color development surface (after storage for one month) were measured in the same manner as described above, and were evaluated in the same manner as in the above-described comparative example. The above measurement and evaluation results are shown in Table D1.

As is clear from Table D1, the coloring compositions of Examples D1 to D2 in which Compounds D1 to D2 and Pigment Dispersant A5 were used in combination were compared with the compositions of Comparative Examples D1 to D2 in which Compounds D1 to D2 were used alone. The viscosity before storage and after storage (after 1 month) is low, the gloss is also good, and it has excellent properties as a coloring composition.

[Example D3] In order to produce a color filter having RGB pixels, a color composition of R, G, and B was obtained in accordance with the formulation of Table D2 below.

In the same manner as in the embodiment A5, a color filter having RGB pixels was prepared. The obtained color filter has excellent spectral characteristics, excellent light resistance, heat resistance, and the like, and is excellent in light permeability, and exhibits excellent properties as a color filter for liquid crystal color display. .

According to the invention as described above, by using a specific pigment dispersant as a red pixel of a color filter to form a doubling effect by using a pigment dispersant of a coloring composition, it can be avoided in a single single use case. In particular, it is possible to avoid the aggregation of the pigment particles, thereby producing a stable coloring composition and avoiding the occurrence of foreign matter, and finally, in the use of the coloring composition for the color filter, the characteristic of having an excellent spectral curve can be obtained. It is a color filter that has a clear and vivid color tone, a high transparency, and is excellent in light quality, heat resistance, solvent resistance, smear resistance, and water resistance.

Claims (14)

A pigment dispersing agent characterized by comprising a single component (a) described below, or comprising the following component (a) and the following component (b); (a) component: a diketopyrrolopyrrole having an acidic sulfate group (Diketo-pyrrolo-pyrrol) pigment and a pigment complex of a diketopyrrolopyrrole pigment not containing an acidic sulfate group, wherein each diketopyrrolopyrrole pigment molecule has an acidic sulfate group number of 0.05 to 0.5; (b) component: A dye containing an acidic sulfate group other than the above component (a), a metal salt thereof, ammonium chloride or an amino group thereof. The pigment dispersant according to claim 1, wherein the component (b) is selected from the following general formula (I), general formula (II), general formula (III), and general formula (1V); a compound, a metal salt thereof, an ammonium chloride and/or an amine salt, (wherein X ₁ is a hydrogen atom, a halogen atom, an alkyl group or a decylamino group, and Y ₁ is an anthraquinonylamino group, an phenylamino group, a naphtylamino group or a phenoxy group, The substituent is an unsubstituted or substituted halogen atom, an alkyl group or a hydrazine amino group; R ₁ is a substituted or unsubstituted hydrogen atom, an alkyl group or a phenyl group; and R ₂ is substituted or unsubstituted. Alkenyl, phenylene or naphthylene based substituent;) (wherein X ₁ is a hydrogen atom, a halogen atom or an alkyl group; R ₁ is a hydrogen atom, a substituted or unsubstituted alkyl group or a phenyl group; and R ₂ is a substituted or unsubstituted phenyl group or a naphthalene group; The base, the substituent k is the average number of acidic sulfate groups of the corresponding compound, which is a number of 0.5 to 2; (wherein R ₁ is a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, a substituted or unsubstituted aromatic hydroxy group or a substituted or unsubstituted phthalimido group; R ₂ is a hydrogen oxy group An atom or a hydroxyl group; R ₃ is a halogen atom; m is an integer representing 0 to 4; n is an average number of introduced acidic sulfate groups of the corresponding compound, and is a number from 0.5 to 4; (where A is R ₁ and R ₂ represent a hydrogen atom, a halogen atom, a hydroxyl group, an alkyl group, a carbonyl group, an acidic sulfate group or a trifluoromethyl group; and R ₃ represents a hydrogen atom, a halogen atom, a hydroxyl group or an alkyl group; R ₄ , R ₅ , R ₆ and R ₇ represent a hydrogen atom, a halogen atom, a methyl group or a cyano group; M represents a hydrogen atom, a metal atom, an ammonium group or an amino group; and the n system represents a group 1 to 3. Integer). The pigment dispersant according to claim 1, wherein the diketopyrrolopyrrole pigment which does not contain an acidic sulfate group is represented by the general formula (v): (wherein R ₁ and R ₂ are each independently a hydrogen atom, a halogen atom, a cyano group, an alkyl group or a phenyl group). The pigment dispersant according to claim 1, wherein the acidic sulfate group of the diketopyrrolopyrrole pigment containing an acidic sulfate group is selected from the group consisting of a free acid sulfate group, an acid sulfate group metal salt, an amine salt, and At least one of ammonium salts. The pigment dispersant according to claim 2, wherein the R ₂ in the general formula (I) is selected from the group consisting of taurine, N-methyl taurine, o-aminobenzenesulfonic acid, m-aminobenzene. Sulfonic acid, p-aminobenzenesulfonic acid, 4-chloroaniline-3-sulfonic acid, 2-p-nitroaniline-4-sulfonic acid, 2-aminophenol-4-sulfonic acid, o-methoxyaniline-5- Sulfonic acid, p-methoxyaniline-5-sulfonic acid, o-toluidine-4-sulfonic acid, m-toluidine-4-sulfonic acid, p-toluidine-2-sulfonic acid, 2-chloro-p -Toluidine-3-sulfonic acid, 3-Ammonia-6-chloro-4-o-sulfobenzoic acid, 1-Ammonia-8-naphthalenesulfonic acid, 2-Ammonia-1-caesulfonic acid, 5-Ammonia-1 - A group in which an amino group is removed from the amines of cesulfonic acid, 6-amino-1-naphthalenesulfonic acid and 5-amino-3-naphthalenesulfonic acid. The pigment dispersant according to claim 2, wherein R ₂ in the general formula (II) is selected from the group consisting of aniline, N-methylaniline, toluidine (o-, m- or p-), methoxy A group in which an amino group is removed from the amine of aniline (o-, m- or p-), chloroaniline (o-, m- or p-), benzylidene, 1-naphthylamine and 2-naphthylamine. The pigment dispersant according to claim 1, wherein the mass ratio of the component (a) to the component (b) is a: b = 10: 90 to 90: 10. A coloring composition for a color filter, which comprises a red pigment and a pigment dispersant and a resin dispersant and a resin varnish as described in claim 1. The coloring composition for a color filter according to Item 8, wherein the red pigment is C.I. Pigment Red 254. The coloring composition for a color filter according to Item 8, wherein the resin dispersing agent is a cationic resin dispersing agent. A method of manufacturing a color filter, characterized in that the method for manufacturing a color filter comprising a color pixel formed on a color filter substrate, wherein the coloring pixel is used, The color filter described in Item 8 is formed by coloring a composition. A color filter characterized by being manufactured as described in claim 11 of the patent application. An image display device characterized by containing a color filter as described in claim 12 of the patent application. An information transmission machine characterized by comprising the image display device as described in claim 13 of the patent application.