JP2010235637A - Pigment composition for color filter, and coloring composition - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a pigment composition for improving the contrast of a color filter to be used for a color liquid crystal display and a solid-state imaging device. <P>SOLUTION: The pigment composition is obtained by mechanically kneading a mixture containing an organic pigment, a basic dye derivative, a water-soluble inorganic salt, a water-soluble organic solvent that does not substantially dissolve the water-soluble inorganic salt, and a rosin-modified maleic acid resin, and then removing the water-soluble inorganic salt and the water-soluble organic solvent. A coloring composition for a color filter is obtained by dispersing the pigment composition in a transparent resin. <P>COPYRIGHT: (C)2011,JPO&INPIT

Description

The present invention relates to a pigment composition used for a color filter used in a color liquid crystal display device and a solid-state imaging device, a colored composition using the pigment, and a color filter using the colored composition.

  The color filter of the liquid crystal display device has a red pixel portion (R), a green pixel portion (G), and a blue pixel portion (B). Each of these pixel portions has a structure in which a thin film of a synthetic resin in which an organic pigment is dispersed is provided on a substrate, and organic pigments of red, green, and blue are used as the organic pigment.

Among these pixel portions, a diketopyrrolopyrrole pigment (CI Pigment Red 254) is generally used as a red organic pigment for forming a red pixel portion, and for color adjustment as necessary. In addition, an anthraquinone pigment (CI Pigment Red 177), which is a red organic pigment, is used in combination.
Further, as the green organic pigment for forming the green pixel portion, phthalocyanine pigments (CI Pigment Green 36, 7 and 58) are generally used, and if necessary, a yellow organic pigment can be used. A certain quinophthalone (CI Pigment Yellow 138), an azobarbituric acid nickel complex melamine clathrate is used.
Furthermore, as a blue organic pigment for forming a blue pixel portion, generally an ε-type copper phthalocyanine pigment (CI Pigment Blue 15: 6) is used, and for color matching as necessary, A purple organic pigment dioxazine violet pigment (CI Pigment Violet 23) is used in combination.

In order to improve the performance of the color filter, an improvement in contrast is required. In order to fulfill this demand, it is generally known to further reduce the primary particle size of the pigment.
As methods for reducing the primary particle diameter of pigments, Patent Documents 1 to 4 describe a kneader together with a water-soluble organic solvent that dissolves at least a part of a water-soluble inorganic salt such as a pigment derivative and sodium chloride in an organic pigment. (Hereinafter, kneading a mixture containing a pigment, a water-soluble inorganic salt and a water-soluble organic solvent is called salt milling), and then removing the inorganic salt and the organic solvent by washing with water. . However, when the pigment is further miniaturized by the methods described in Patent Documents 1 to 4, there is a problem that the dispersibility is deteriorated and the viscosity is increased, and at the same time, the contrast is not improved despite the miniaturization.

JP 2007-224177 A JP-A-10-245502 JP 2005-181383 A Japanese Patent Laid-Open No. 06-228454

  An object of the present invention is to provide a pigment composition that has good dispersibility, can reduce viscosity, and can improve contrast when used in a color filter, a color composition for color filter using the same, and a color filter.

  As a result of continuing intensive studies to solve the above-mentioned problems, the present inventors have used a pigment derivative and a rosin-modified maleic resin when salt milling an organic pigment. The inventors have found that an organic pigment having good dispersibility can be produced, and have reached the present invention.

That is, the present invention relates to a pigment composition comprising a mixture containing an organic pigment, a dye derivative, and a rosin-modified maleic resin.
Furthermore, the present invention relates to a pigment composition, wherein the pigment derivative is a basic derivative.
Furthermore, the present invention relates to an organic pigment in which the organic pigment is diketopyrrolopyrrole, phthalocyanine, anthraquinone, quinophthalone, dioxazine violet, or an azo metal complex.

Furthermore, the present invention includes kneading a mixture containing an organic pigment, a dye derivative, a water-soluble inorganic salt, a water-soluble organic solvent that does not substantially dissolve the water-soluble inorganic salt, and a mixture containing a rosin-modified maleic resin, The present invention relates to a pigment composition obtained by removing a water-soluble inorganic salt and a water-soluble organic solvent.
Furthermore, this invention relates to the coloring composition for color filters characterized by dispersing the said pigment composition in transparent resin.
Furthermore, the present invention relates to a color filter comprising a pixel formed using a coloring composition for a color filter.

  Compared with existing organic pigments used for color filters, it has become possible to provide pigments with good dispersibility, reduced viscosity, and improved contrast.

  Next, the present invention will be described in more detail with reference to the practice of the invention. Below, the specific example of the organic pigment which can be used for this invention is shown by a color index number. Examples of red pigments include C.I. I. Pigment Red 7, 9, 14, 41, 48: 1, 48: 2, 48: 3, 48: 4, 81: 1, 81: 2, 81: 3, 97, 122, 123, 146, 149, 168, 177, 178, 180, 184, 185, 187, 192, 200, 202, 208, 210, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, 242, 246, 254, 255, Red pigments such as H.264 and 272 can be used.

  Examples of yellow pigments include C.I. I. Pigment Yellow 1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 15, 16, 17, 18, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1, 37, 37: 1, 40, 42, 43, 53, 55, 60, 61, 62, 63, 65, 73, 74, 77, 81, 83, 86, 93, 94, 95, 97, 98, 100, 101, 104, 106, 108, 109, 110, 113, 114, 115, 116, 117, 118, 119, 120, 123, 125, 126, 127, 128, 129, 137, 138, 139, 147, 148, 150, 151, 152, 153, 154, 155, 156, 161, 162, 164, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 17 Yellow pigments such as 6, 177, 179, 180, 181, 182, 185, 187, 188, 193, 194, and 199 can be used.

Examples of orange pigments include C.I. I. Orange pigments such as CI Pigment Orange 36, 38, 43, 51, 55, 59, 61 can be used.
Examples of the green pigment include C.I. I. Green pigments such as CI Pigment Green 7, 10, 36, 37, and 58 can be used. A yellow pigment can be used in combination with the green composition.
Examples of blue pigments include C.I. I. Blue pigments such as CI Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, and 64 can be used. Examples of purple pigments include C.I. I. Pigment violet 1, 19, 23, 27, 29, 30, 32, 37, 40, 42, 50, C.I. I. Purple pigments such as CI Pigment Blue 80 can be used.
Examples of cyan pigments include C.I. I. Blue pigments such as CI Pigment Blue 15: 1, 15: 2, 15: 4, 15: 3, 15: 6, 16, and 81 can be used.
Examples of magenta color pigments include C.I. I. Pigment violet 1, 19, C.I. I. Purple pigments such as CI pigment red 144, 146, 177, 169, 81, and red pigments can be used. A yellow pigment can be used in combination with the magenta composition.
The coloring composition for a color filter of the present invention can contain a dye within a range that does not reduce heat resistance for color matching.

  Among these organic pigments, red pigments include C.I. I. Pigment red 254, C.I. I. Pigment red 255, C.I. I. Pigment red 264, C.I. I. Diketopyrrolopyrrole represented by Pigment Orange 71, and C.I. I. An anthraquinone type represented by CI Pigment Red 177 is preferable. I. Pigment green 7, C.I. I. A phthalocyanine series represented by pigment green 36 is preferred. Examples of the yellow pigment used in combination with the green coloring composition include C.I. I. A quinophthalone-based nickel azobarbiturate complex melamine clathrate represented by CI Pigment Yellow 138 is preferred. Examples of blue pigments include C.I. I. The phthalocyanine type represented by pigment blue 15: 6 is preferable, and examples of the violet pigment used in combination with the blue coloring composition include C.I. I. Pigment violet 23, C.I. I. Pigment Violet 37 is preferable.

The dye derivative is a compound in which a substituent is introduced into the molecule of the organic dye, and functions to suppress crystal growth of the organic pigment during salt milling.
Examples of the substituent introduced into the organic dye include a carboxyl group, a sulfonic acid group, a carbamoyl group, a sulfonamide group, and a basic substituent represented by the following general formula.

Ｘ：直接結合、−ＣＨ₂ ＮＨＣＯＣＨ₂ −、−ＳＯ₂ ＮＨ−、−ＣＯＮＨＯＣＨ₂ ＮＨ−、または−（ＣＨ₂ ）_q ＮＨ−を表す。
Ｒ₁ 、Ｒ₂ ：それぞれ独立に、置換されてもよい飽和もしくは不飽和のアルキル基、またはＲ₁ 、Ｒ₂ で窒素、酸素もしくは硫黄原子を含む、置換されてもよい複素環を表す。
有機色素に導入する置換基例を以下に示すが、本発明はこれによって限定されるものではない。

X: a direct _{bond, -CH 2 NHCOCH 2 -, -} SO 2 NH -, - CONHOCH 2 NH-, or - represents a (CH _{2) q} NH-.
R ₁ and R ₂ each independently represents a saturated or unsaturated alkyl group which may be substituted, or a heterocyclic ring which may be substituted containing a nitrogen, oxygen or sulfur atom in R ₁ and R ₂ .
Although the example of a substituent introduce | transduced into an organic pigment | dye is shown below, this invention is not limited by this.

  Moreover, although the azo derivative shown in the following figure can also be used, this invention is not limited by this.

  The amount of the pigment derivative is not particularly limited, but is preferably 0.5 to 40% by weight, particularly 5 to 30% by weight, based on the organic pigment. This is because, as the amount ratio of the dye derivative to the organic pigment is larger, the crystal growth is inhibited and the effect of miniaturization is larger, but the chromaticity shift of the organic pigment occurs. In addition, since the pigment derivative also has an effect as a dispersant, it is preferable to select a pigment with good dispersibility in the transparent resin varnish. However, other pigment derivatives or dispersions other than the pigment derivative that have a high crystal growth prevention effect are preferable. You may combine with an agent. Dispersants other than pigment derivatives include condensates of ricinoleic acid and 12-hydroxystearic acid, basic polymer compounds, copolymers containing acid groups, fatty acid esters, aliphatic polyamine / polyester graft polymers, polyethylene / So-called resin-type dispersants such as polypropylene addition polymers can be used. These dispersants are used at the time of salt milling treatment or at the time of dispersing the salt milling treatment pigment in the transparent resin varnish.

  The water-soluble inorganic salt serves as a crushing aid, and the organic pigment is crushed using the high hardness of the inorganic salt during salt milling, and the primary particles of the organic pigment are refined. The inorganic salt is not particularly limited as long as it is soluble in water, and sodium chloride, barium chloride, potassium chloride, sodium sulfate and the like can be used, but sodium chloride (salt) is preferably used from the viewpoint of price. . The amount of the inorganic salt used for salt milling is preferably 1 to 20 times by weight, particularly 3 to 10 times by weight of the organic pigment, from the viewpoints of processing efficiency and production efficiency. The larger the ratio of the inorganic salt to the organic pigment, the higher the refinement efficiency, but the smaller the amount of processing of the organic pigment at one time.

  The water-soluble organic solvent functions to wet the organic pigment, the dye derivative and the water-soluble inorganic salt, and is particularly limited as long as it dissolves (mixes) in water and does not substantially dissolve the inorganic salt to be used. Not. However, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable from the viewpoint of safety because the temperature rises during salt milling and the solvent easily evaporates. Examples of the water-soluble organic solvent include 2-methoxyethanol, 2-butoxyethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol. , Triethylene glycol monomethyl ether, liquid polyethylene glycol, 1-methoxy-2-propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, liquid polypropylene glycol, etc. Is used.

  The rosin-modified maleic resin in the present invention preferably has an acid value of 25 mgKOH / g or more and 320 mgKOH / g or less, particularly preferably an acid value of 100 mgKOH / g or more and 320 mgKOH / g or less. This is because if the acid value is lower than 25 mg KOH / g, the affinity with the water-soluble organic solvent is not good, and the surface cannot be coated. Further, when the acid value is higher than 320 mgKOH / g, the solubility in water is increased, and peeling from the surface of the organic pigment occurs when the water-soluble inorganic salt is removed. The addition amount is preferably 2 to 100% by weight, particularly 10 to 60% by weight of the organic pigment. This is because when the amount ratio of the rosin-modified maleic resin to the organic pigment is less than 2% by weight, the surface of the organic pigment cannot be completely covered and the dispersibility is not improved. Moreover, when there is more addition amount than 100 weight%, it is because the coloring power of an organic pigment will fall.

  By dispersing the pigment of the present invention in a transparent resin, a colored composition used for producing a color filter can be obtained. The pigment and the transparent resin are blended at a ratio of 1: 4 to 10: 1 in the solid content weight ratio. Various dispersing means such as a three-roll mill, a two-roll mill, a sand mill, and a kneader can be used for dispersing the pigment in the transparent resin. Moreover, in order to make these dispersion | distribution favorable, dispersion | distribution adjuvants, such as various surfactant and a pigment derivative, can be added suitably. The dispersion aid is excellent in dispersing the pigment and has a great effect of preventing re-aggregation of the pigment after dispersion. Therefore, when a coloring composition obtained by dispersing the pigment in a transparent resin using the dispersion aid is used. A color filter having excellent transparency can be obtained.

  The transparent resin is a resin having a transmittance of 80% or more, preferably 95% or more in the entire wavelength region of 400 to 700 nm in the visible light region. Transparent resins include thermosetting resins, thermoplastic resins, photosensitive resins, and monomers, oligomers, etc. that form a coating film similar to the resin when cured by radiation irradiation. These can be used alone or in combination. Can be used. Moreover, when hardening a coloring composition by ultraviolet irradiation, a photoinitiator etc. are used. However, since a high-temperature heating process is performed in a later process in the production of the color filter, it is necessary to use a resin having good resistance in the heating process. In addition, since processing with various solvents and chemicals is also performed in a later process, the solvent resistance and chemical resistance of the formed image are also required.

  Examples of thermosetting resins and thermoplastic resins include butyral resin, styrene-maleic acid copolymer, chlorinated polyethylene, chlorinated polypropylene, polyvinyl chloride, vinyl chloride-vinyl acetate copolymer, polyvinyl acetate, and polyurethane. Resin, phenol resin, polyester resin, acrylic resin, alkyd resin, styrene resin, polyamide resin, rubber resin, cyclized rubber, epoxy resin, celluloses, polybutadiene, polyimide resin, benzoguanamine resin, melamine resin, urea resin, etc. Is mentioned.

  As the photosensitive resin, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group, and an amino group is bonded to a (meth) acrylic compound, cinnamic acid, or the like via an isocyanate group, an aldehyde group, an epoxy group, or the like. A resin into which a photocrosslinkable group is introduced is used. Further, a linear polymer containing an acid anhydride such as a styrene-maleic anhydride copolymer or an α-olefin-maleic anhydride copolymer is converted into a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate. Half-esterified polymers can also be used.

  Monomers and oligomers that are cured by radiation irradiation to form a coating film similar to a resin include 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, cyclohexyl (meth) acrylate, polyethylene glycol di (meth) ) Acrylate, pentaerythritol tri (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tricyclodecanyl (meth) acrylate, hexa (meth) acrylate of caprolactone adduct of dipentaerythritol hexa (meth) acrylate, etc. Acrylic acid ester and methacrylic acid ester, acrylic acid, methacrylic acid, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, styrene, vinyl acetate, acrylonitrile Melamine (meth) acrylate, epoxy (meth) acrylate prepolymer, and the like.

  As photoinitiators, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1one, 1-hydroxycyclohexyl Acetophenone photoinitiators such as phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzyl Benzoin series such as dimethyl ketal, benzophenone series photoinitiator, benzophenone, benzoylbenzoic acid, methyl benzoylbenzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4 Benzophenone photoinitiators such as benzoyl-4'-methyldiphenyl sulfide, thioxanthone photoinitiators such as thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropylthioxanthone, 2,4-diisopropylthioxanthone Agent, 2,4,6-trichloro-s-triazine, 2-phenyl-4,6-bis (trichloromethyl) -s-triazine, 2- (p-methoxyphenyl) -4,6-bis (trichloromethyl) -S-triazine, 2- (p-tolyl) -4,6-bis (trichloromethyl) -s-triazine, 2-pienyl-4,6-bis (trichloromethyl) -s-triazine, 2,4- -Bis (trichloromethyl) -6-styryl s-triazine, 2- (naphth-1-yl) -4,6-bis (to Chloromethyl) -s-triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6-triazine , 2,4-trichloromethyl (4′-methoxystyryl) -6-triazine and other compounds such as triazine photoinitiators and carbazole photoinitiators and imidazole photoinitiators are used.

  The photoinitiator may be used alone or in combination of two or more. As a sensitizer, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthrenequinone, Combined use of compounds such as camphorquinone, ethylanthraquinone, 4,4'-diethylisophthalophenone, 3,3 ', 4,4'-tetra (t-butylperoxycarbonyl) benzophenone, 4,4'-diethylaminobenzophenone You can also

  In the coloring composition for a color filter, a solvent can be used in order to sufficiently disperse the coloring agent and apply it on the glass substrate so that the dry film thickness is 0.2 to 5 μm. Examples of the solvent include cyclohexanone, ethyl cellosolve acetate, butyl cellosolve acetate, 1-methoxy-2-propyl acetate, diethylene glycol dimethyl ether, ethylbenzene, ethylene glycol diethyl ether, xylene, ethyl cellosolve, methyl-n amyl ketone, propylene glycol monomethyl ether toluene, methyl ethyl ketone. , Ethyl acetate, methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent and the like, and these are used alone or in combination.

  The coloring composition for a color filter of the present invention can be a gravure offset printing ink, a waterless offset printing ink, a silk screen printing ink, a solvent developing type or an alkali developing type coloring resist agent. These printing ink, coloring resist agent, etc. are coarse particles of 5 μm or more, preferably coarse particles of 1 μm or more, more preferably 0.5 μm or more, and coarse particles by means of centrifugation, sintered filter, membrane filter and the like. It is manufactured by removing the mixed dust.

  Since the printing ink can form patterned pixels of each color simply by repeating printing and drying, it is low cost and excellent in mass productivity as a method for producing a color filter. Furthermore, it is possible to print a fine pattern having high dimensional accuracy and smoothness by the development of printing technology. In the case of producing a color filter by printing, it is important to control the fluidity of the ink on the printing press, and the ink viscosity can be adjusted with a dispersant or extender pigment.

  The solvent development type or alkali development type coloring resist agent is applied on a transparent substrate such as a glass plate by a coating method such as spin coating, slit coating or roll coating. Next, UV exposure is performed through a photomask, and the unexposed portion is washed away with a solvent or an alkali developer to form a desired pattern, and then the same operation is repeated for other colors to form a color filter having pixels of each color. To manufacture. This manufacturing method is called a photolithography method, and a color filter with higher accuracy than the printing method can be manufactured.

  As the alkaline developer, an aqueous solution such as sodium carbonate or caustic soda is used, and an organic base such as dimethylbenzylamine or triethanolamine can also be used. Moreover, an antifoamer and surfactant can also be added. In order to increase the UV exposure sensitivity, after coating and drying the colored resist agent, a water-soluble or alkaline water-soluble resin such as polyvinyl alcohol or water-soluble acrylic resin is applied and dried to form a film that prevents polymerization inhibition by oxygen. Then, ultraviolet exposure can be performed.

  As a method for producing a color filter using a pigment, in addition to the above, there are an electrodeposition method, a transfer method and the like, but the colored composition of the present invention can be used in any method. The electrodeposition method is a method for producing a color filter by using a transparent conductive film formed on a transparent substrate and electrodepositing a coloring material on the transparent conductive film by electrophoresis of colloidal particles. The transfer method is a method in which a color filter layer is formed in advance on the surface of a peelable transfer base sheet, and this color filter layer is transferred to a desired transparent substrate.

  EXAMPLES Hereinafter, although this invention is demonstrated based on an Example, this invention is not limited by this. In Examples and Comparative Examples, “part” means “part by weight” and “%” means “% by weight”. Prior to the examples, the dye derivatives used in the examples are shown.

色素誘導体(b)

色素誘導体(c)

色素誘導体(d)

色素誘導体(e)

色素誘導体(f)

色素誘導体(g)

色素誘導体(h)

Dye derivative (a)

Dye derivative (b)

Dye derivative (c)

Dye derivative (d)

Dye derivative (e)

Dye derivative (f)

Dye derivative (g)

Dye derivative (h)

Preparation of pigment for red color filter
[Example 1]
76 parts of a commercially available diketopyrrolopyrrole pigment (“Irgazine DPP RED B-CF” manufactured by Ciba Specialty Chemicals), 4 parts of a pigment derivative (a), 800 parts of sodium chloride, and 100 parts of diethylene glycol are made of a stainless steel kneader (Inoue Manufacturing Co., Ltd.). And kneaded at 60 ° C. for 10 hours. To this mixture, 25 parts of rosin-modified maleic resin (“Marquide No. 32” acid value 125 mg KOH / g manufactured by Arakawa Chemical Industries, Ltd.) was added and kneaded at 60 ° C. for 2 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.

[Example 2]
A dry pigment was obtained in the same manner as in Example 1 except that the dye derivative (a) was changed to the dye derivative (b).
[Example 3]
A dried pigment was obtained by performing the same operation as in Example 1 except that the rosin-modified maleic resin was changed from “Marquide No. 32” manufactured by Arakawa Chemical Industries to “Marquide No. 33 (acid value 310 mgKOH / g)”. It was.

[Example 4]
C. I. Pigment Red 177 (“Chromophthal Red A2B” manufactured by Ciba Specialty Chemicals) 76 parts, pigment derivative (c) 4 parts, sodium chloride 800 parts, and diethylene glycol 100 parts in a stainless steel kneader (Inoue Seisakusho), 60 The kneading was carried out at 10 ° C. for 10 hours. To this mixture, 23 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries, Ltd.) was added and kneaded at 60 ° C. for 2 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Example 5]
A dry pigment was obtained in the same manner as in Example 4 except that the dye derivative (c) was changed to the dye derivative (d).

Preparation of pigment for green color filter
[Example 6]
76 parts of polybrominated phthalocyanine (LIONOL GREEN 6YK manufactured by Toyo Ink Manufacturing Co., Ltd.), 4 parts of the dye derivative (b), 800 parts of sodium chloride, and 100 parts of diethylene glycol were added at 60 ° C. in a stainless steel kneader (Inoue Seisakusho). Kneaded for hours. To this mixture, 32 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries) was added and kneaded at 60 ° C. for 2 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Example 7]
A dry pigment was obtained in the same manner as in Example 6 except that the rosin-modified maleic resin was changed from “Marquide No. 32” manufactured by Arakawa Chemical Industries to “Marquide No. 33”.

[Example 8]
A commercially available quinophthalone pigment (76 parts of “Pariotol Yellow K0961HD” manufactured by BASF, 4 parts of a pigment derivative (b), 800 parts of sodium chloride, and 100 parts of diethylene glycol in a stainless steel kneader (manufactured by Inoue Seisakusho) at 60 ° C. The mixture was kneaded for 10 hours, and 21 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries, Ltd.) was added to the mixture and kneaded for 2 hours at 60 ° C. Next, the mixture was mixed. Add to 10 times warm water, stir with high speed mixer for about 1 hour while heating to about 80 ° C, make slurry, filter and wash repeatedly to remove sodium chloride and solvent, then dry at 90 ° C overnight As a result, a dry pigment was obtained.
[Example 9]
Except for changing the rosin-modified maleic resin from “Marquide No. 32” manufactured by Arakawa Chemical Industries, Ltd. to “Marquide No. 33”, the same operation as in Example 8 was performed to obtain a dry pigment.
[Example 10]
76 parts of a commercially available metal complex pigment (E4GN-GT manufactured by LANXESS), 4 parts of the dye derivative (b), 240 parts of sodium chloride, and 50 parts of diethylene glycol were added at 100 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho). Kneaded for hours. To this mixture, 32 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries, Ltd.) was added and kneaded at 100 ° C. for 2 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.

Preparation of blue color filter pigment
[Example 11]
76 parts of ε-type copper phthalocyanine pigment (LIONOL BLUE E manufactured by Toyo Ink Manufacturing Co., Ltd.), 4 parts of a pigment derivative (e), 600 parts of sodium chloride, and 100 parts of diethylene glycol at 70 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho) Kneaded for 6 hours. To this mixture, 30 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries, Ltd.) was added and kneaded at 60 ° C. for 2 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.
[Example 12]
A dry pigment was obtained in the same manner as in Example 11 except that the dye derivative (e) was changed to the dye derivative (f).

[Example 13]
A dry pigment was obtained in the same manner as in Example 11 except that the rosin-modified maleic resin was changed from “Marquide No. 32” manufactured by Arakawa Chemical Industries to “Marquide No. 33”.
[Example 14]
76 parts of dioxazine pigment (“Rionogen Violet FG-6240” manufactured by Toyo Ink Manufacturing Co., Ltd.), 4 parts of pigment derivative (g) and 800 parts of sodium chloride were charged into a stainless steel kneader (manufactured by Inoue Seisakusho) at 60 ° C. Kneaded for 10 hours. To this mixture, 20 parts of rosin-modified maleic resin (“Marquide No. 32” manufactured by Arakawa Chemical Industries) was added and kneaded at 60 ° C. for 2 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.

[Example 15]
A dry pigment was obtained in the same manner as in Example 14 except that the dye derivative (g) was changed to the dye derivative (h).
[Example 16]
A dried pigment was obtained in the same manner as in Example 14 except that the rosin-modified maleic resin was changed from “Marquide No. 32” manufactured by Arakawa Chemical Industries to “Marquide No. 33”.

[Comparative Example 1]
76 parts of a commercially available diketopyrrolopyrrole pigment (“Irgazine DPP RED B-CF” manufactured by Ciba Specialty Chemicals), 4 parts of a pigment derivative (a), 800 parts of sodium chloride, and 100 parts of diethylene glycol are made of a stainless steel kneader (Inoue Manufacturing Co., Ltd.). And kneaded at 60 ° C. for 12 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Comparative Example 2]
A dry pigment was obtained in the same manner as in Example 1 except that the rosin-modified maleic resin was changed to a rosin ester resin (“Ester gum AT” acid value of 8 mg KOH / g manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 3]
A dry pigment was obtained in the same manner as in Example 1 except that the rosin-modified maleic resin was changed to hydrogenated rosin ("Hyper CH" manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 4]
80 parts of commercially available diketopyrrolopyrrole pigment (“Irgazine DPP RED B-CF” manufactured by Ciba Specialty Chemicals), 800 parts of sodium chloride, and 100 parts of diethylene glycol at 60 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho). Kneaded for 12 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.

[Comparative Example 5]
C. I. Pigment Red 177 (“Chromophthal Red A2B” manufactured by Ciba Specialty Chemicals) 76 parts, pigment derivative (c) 4 parts, sodium chloride 800 parts, and diethylene glycol 100 parts in a stainless steel kneader (Inoue Seisakusho), 60 The mixture was kneaded for 12 hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Comparative Example 6]
A dry pigment was obtained in the same manner as in Example 4 except that the rosin-modified maleic resin was changed to a rosin ester resin (“Ester Gum AT” manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 7]
A dried pigment was obtained in the same manner as in Example 4 except that the rosin-modified maleic resin was changed to hydrogenated rosin (“Hyper CH” manufactured by Arakawa Chemical Co., Ltd.).

[Comparative Example 8]
C. I. 80 parts of Pigment Red 177 (“Chromophthalred A2B” manufactured by Ciba Specialty Chemicals), 800 parts of sodium chloride, and 100 parts of diethylene glycol were kneaded at 60 ° C. for 12 hours in a stainless steel kneader (manufactured by Inoue Seisakusho). Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Comparative Example 9]
76 parts of polybrominated phthalocyanine (LIONOL GREEN 6YK manufactured by Toyo Ink Manufacturing Co., Ltd.), 4 parts of the dye derivative (b), 800 parts of sodium chloride, and 100 parts of diethylene glycol were added at 12 ° C. at 60 ° C. in a stainless steel kneader. Kneaded for hours. Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.

[Comparative Example 10]
80 parts of polybrominated phthalocyanine (LIONOL GREEN 6YK manufactured by Toyo Ink Manufacturing Co., Ltd.), 800 parts of sodium chloride, and 100 parts of diethylene glycol were kneaded at 60 ° C. for 12 hours in a stainless steel kneader (manufactured by Inoue Seisakusho). Next, the mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent, Drying was performed at 90 ° C. for one day to obtain a dry pigment.
[Comparative Example 11]
A commercially available quinophthalone pigment (76 parts of “Pariotor Yellow K0961HD” manufactured by BASF, 4 parts of a pigment derivative (e), 800 parts of sodium chloride, and 100 parts of diethylene glycol was added at 60 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho). Next, the mixture was poured into 10 times warm water and stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C. to form a slurry, followed by repeated filtration and washing with sodium chloride and solvent. And then dried at 90 ° C. for one day to obtain a dry pigment.

[Comparative Example 12]
Commercially available quinophthalone pigment (80 parts of “Pariotol Yellow K0961HD” manufactured by BASF, 800 parts of sodium chloride, and 100 parts of diethylene glycol were kneaded for 12 hours at 60 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho). The mixture was poured into 10 times warm water, heated to about 80 ° C and stirred with a high speed mixer for about 1 hour to form a slurry, filtered and washed repeatedly to remove sodium chloride and solvent, then at 90 ° C. It was dried for one day and night to obtain a dry pigment.
[Comparative Example 13]
80 parts of a commercially available metal complex pigment (E4GN-GT manufactured by LANXESS), 240 parts of sodium chloride, and 50 parts of diethylene glycol were kneaded at 100 ° C. for 8 hours in a stainless steel kneader (manufactured by Inoue Seisakusho). Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.

[Comparative Example 14]
ε-type copper phthalocyanine pigment (LIONOL BLUE E manufactured by Toyo Ink Manufacturing Co., Ltd.) 76 parts, dye derivative (f) 4 parts, sodium chloride 600 parts, and diethylene glycol 100 parts at 70 ° C. in a stainless steel kneader (manufactured by Inoue Seisakusho) Kneaded for 6 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.
[Comparative Example 15]
A dry pigment was obtained in the same manner as in Example 11 except that the rosin-modified maleic resin was changed to a rosin ester resin (“Ester gum AT” manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 16]
A dry pigment was obtained in the same manner as in Example 11 except that the rosin-modified maleic resin was changed to hydrogenated rosin (“Hyper CH” manufactured by Arakawa Chemical Co., Ltd.).

[Comparative Example 17]
80 parts of ε-type copper phthalocyanine pigment (LIONOL BLUE E manufactured by Toyo Ink Co., Ltd.), 600 parts of sodium chloride, and 100 parts of diethylene glycol were kneaded at 70 ° C. for 6 hours in a stainless steel kneader (manufactured by Inoue Seisakusho). Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.
[Comparative Example 18]
76 parts of dioxazine pigment (“Rionogen Violet FG-6240” manufactured by Toyo Ink Manufacturing Co., Ltd.), 4 parts of pigment derivative (h), and 800 parts of sodium chloride were charged into a stainless steel kneader (manufactured by Inoue Seisakusho) at 60 ° C. Kneaded for 10 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.

[Comparative Example 19]
80 parts of dioxazine pigment (“Rionogen Violet FG-6240” manufactured by Toyo Ink Manufacturing Co., Ltd.) and 800 parts of sodium chloride were charged into a stainless steel kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, this mixture is poured into 10 times warm water, stirred at a high speed mixer for about 1 hour while being heated to about 80 ° C., made into a slurry, repeatedly filtered and washed with water to remove sodium chloride and the solvent. Drying was carried out at 0 ° C. for 1 day to obtain a dry pigment.
[Comparative Example 20]
A dried pigment was obtained in the same manner as in Example 14 except that the rosin-modified maleic resin was changed to a rosin ester resin (“Ester gum AT” manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 21]
A dry pigment was obtained in the same manner as in Example 14 except that the rosin-modified maleic resin was changed to hydrogenated rosin (“Hyper CH” manufactured by Arakawa Chemical Co., Ltd.).
[Comparative Example 22]
A dry pigment was obtained in the same manner as in Example 14 except that the rosin-modified maleic resin was changed to a modified acrylic block copolymer ("Disper BYK 2000" manufactured by BYK Chemie).

(Evaluation of color filter characteristics of pigments obtained in Examples and Comparative Examples)
The chromaticity and lightness of the pigments obtained in Examples and Comparative Examples were measured. In these evaluations, a photosensitive coloring composition was prepared, the photosensitive coloring composition was applied to a glass substrate using a spin coater, and the chromaticity, brightness, and contrast of the coated substrate after exposure and heating were measured. The evaluation method will be described in detail below.

(Preparation of acrylic resin solution)
A reaction vessel was charged with 800 parts of cyclohexanone, heated to 100 ° C. while injecting nitrogen gas into the vessel, and a mixture of the following monomer and thermal polymerization initiator was added dropwise at the same temperature over 1 hour to carry out a polymerization reaction.
Styrene 60.0 parts Methacrylic acid 60.0 parts Methyl methacrylate 65.0 parts Butyl methacrylate 65.0 parts Azobisisobutyronitrile 10.0 parts

  After the dropwise addition, the mixture was further reacted at 100 ° C. for 3 hours, and then 2.0 parts of azobisisobutyronitrile dissolved in 50 parts of cyclohexanone was added, and the reaction was further continued at 100 ° C. for 1 hour to obtain a weight average molecular weight. A solution of about 40,000 acrylic resin was obtained. After cooling to room temperature, about 2 g of the resin solution was sampled, heated and dried at 180 ° C. for 20 minutes to measure the nonvolatile content, and cyclohexanone was added to the previously synthesized resin solution so that the nonvolatile content was 20%. An acrylic resin solution was prepared.

(Preparation of each color photosensitive coloring composition)
A mixture having the following composition was uniformly dispersed, stirred and mixed, and then filtered through a 1 μm filter to prepare a photosensitive colored composition.

4.8 parts of organic pigment
(Examples 1-16, Comparative Examples 1-22)
Acrylic resin solution 24.0 parts
5.4 parts of trimethylolpropane triacrylate
(Shin Nakamura Chemical "NK Ester ATMPT")
Photoinitiator ("Irgacure 907" manufactured by Ciba Geigy) 0.3 parts
Sensitizer (Hoabaya Chemical "EAB-F") 0.2 parts
65.1 parts cyclohexanone

  The photosensitive coloring composition produced using the organic pigment obtained in Examples 1 to 16 and Comparative Examples 1 to 22 was placed on a glass substrate having a thickness of 100 mm × 100 mm and a thickness of 1.1 mm using a spin coater at 500 rpm, Coating was performed at 1500 rpm and 3000 rpm to obtain three types of coated substrates having different film thicknesses. Next, after drying at 70 ° C. for 20 minutes, ultraviolet exposure was performed with an integrated light amount of 150 mJ using an ultrahigh pressure mercury lamp. The coated substrate was heated at 230 ° C. for 1 hour and then allowed to cool to produce a colored film. Then, the spectrum of the obtained colored film was measured with a spectrophotometer (“U-3500” manufactured by Hitachi, Ltd.), and each chromaticity (Y, x, y) with a C light source was calculated. Then, the contrast of the obtained colored film was measured with a contrast meter (“Contrast Tester MODEL CT-1” manufactured by Aisaka Electric Co., Ltd.). In the substrate coated with the dispersion using each organic pigment, the calculation is performed at x = 0.6 for the red coloring composition, and the calculation is performed at y = 0.5 for the green and yellow coloring compositions. In the blue coloring composition and the purple coloring composition, Y, x, and contrast when y = 0.1 were further calculated. The viscosity of the dispersion was measured with an EL type viscometer (TV-20 unit made by Toki Sangyo Co., Ltd., mPa · s). The value at 25 ° C. and 100 rpm was measured. The red coloring composition is shown in Tables 1-2, the green coloring composition is shown in Tables 3-5, the blue coloring composition is shown in Tables 6-7, and when the rosin-modified maleic resin is not treated for each pigment The contrast ratio when the contrast of 1.00 was 1.00 was calculated.

  As is apparent from Tables 1 to 7, in the color filter colored films of Examples 1 to 16 obtained using the pigment composition produced by the method of the present invention, a diketopyrrolopyrrole pigment and an anthraquinone pigment Phthalocyanine pigments, quinophthalone pigments, nickel azobarbiturate complex melamine inclusions, and pigment dispersions obtained by treating a dioxazine pigment with a rosin-modified maleic acid resin are Comparative Examples 1, 5, 9, 11, 13, 14 , 18, the contrast is improved, and the viscosity is further reduced. From this, it can be seen that the dispersions using the pigments prepared in Examples 1 to 16 are colored compositions having excellent dispersibility.

Further, in Comparative Examples 2, 3, 6, 7, 15, 16, 20, 21, and 22, in the sample to which a resin other than the rosin-modified maleic resin was added, the contrast was not improved and the viscosity was also lowered. Not done. From this, it can be seen that rosin-modified maleic resin is good as the resin to be treated.

Claims (6)

  A pigment composition comprising a mixture comprising an organic pigment, a dye derivative, and a rosin-modified maleic resin.   The pigment composition according to claim 1, wherein the organic pigment is diketopyrrolopyrrole, phthalocyanine, anthraquinone, quinophthalone, dioxazine violet, or an azo metal complex. 3. The pigment composition according to claim 1, wherein the pigment derivative is a basic derivative.   After mechanically kneading a mixture containing an organic pigment, a dye derivative, and a rosin-modified maleic resin, a water-soluble inorganic salt, and a water-soluble organic solvent that does not substantially dissolve the water-soluble inorganic salt, The method for producing a pigment composition according to any one of claims 1 to 3, wherein the inorganic inorganic salt and the water-soluble organic solvent are removed. A coloring composition for a color filter, comprising a pigment composition obtained by the production method according to claim 4 dispersed in a transparent resin. A color filter comprising pixels formed using the colored composition for a color filter according to claim 5.