JP2003057425A - Pigment for color filter, method for manufacturing the same and coloring composition for color filter using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide pigment for a color filter excellent in heat resistance and light resistance and giving an excellent red filter with high brightness, a method for manufacturing the same and a coloring composition for the color filter using the same. SOLUTION: The pigment for the color filter is manufactured by blending a mixture which contains a diketopyrrolopyrrole pigment (A), a diketopyrrolopyrrole pigment (B) with a wavelength for a midpoint between minimum and maximum transmittance in spectral transmittance different from that of the pigment (A), a coloring matter derivative (C), a water soluble inorganic salt (D) and a water soluble organic solvent (E) essentially not dissolving the water soluble inorganic salt (D) and subsequently removing the water soluble inorganic salt (D) and the water soluble organic solvent (E). Correspondingly, the coloring composition for the color filter contains a colorant carrier composed of a transparent resin, its precursor or their mixture and the pigment dispersed in the colorant carrier.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a pigment used for a color filter of a color liquid crystal display device and a solid-state image pickup device, a method for producing the same, and a coloring composition for a color filter.

[0002]

2. Description of the Related Art A color filter is one in which two or more kinds of fine bands (stripes) of different hues are arranged in parallel or intersecting on the surface of a transparent substrate such as glass, or fine pixels are arranged vertically and horizontally. It consists of the ones arranged in. The pixels are as small as several tens to several hundreds of microns, and are arranged in a predetermined arrangement for each hue. A color filter is used in a color liquid crystal display device. Generally, a transparent electrode for driving a liquid crystal is formed on the color filter by vapor deposition or sputtering, and in order to orient the liquid crystal in a certain direction on the transparent electrode. Alignment film is formed. In order to sufficiently obtain the performance of these transparent electrode and alignment film, it is necessary to perform the forming step at a high temperature of generally 200 ° C. or higher, preferably 230 ° C. or higher.

Therefore, at present, as a method of manufacturing a color filter, a method called a pigment dispersion method, which uses a pigment having excellent light resistance and heat resistance as a colorant, is mainly used, and the following two methods are mainly used. Color filters are manufactured in. In the first method, a photosensitive transparent resin solution in which a pigment is dispersed is applied to a transparent substrate such as glass, the solvent is removed by drying, and then pattern exposure of one filter color is performed, and then the unexposed portion is exposed. Is removed in the developing step to form a pattern for the first color, and if necessary, treatment such as heating is performed, and then the same operation is sequentially repeated for all the filter colors to produce a color filter.

In the second method, a transparent resin solution in which a pigment is dispersed is applied to a transparent substrate such as glass, the solvent is removed by drying, and then a resist such as a positive resist is applied on the coating film. Then, pattern exposure of one filter color is performed, development is performed to form a resist pattern, and this is used as an etching resist to remove the pigment-dispersed coating film without the resist pattern with an etching solution and peel the resist coating film. A color filter can be manufactured by forming a pattern for the first color by applying a treatment such as heating, if necessary, and then repeating the same operation sequentially for all filter colors. The development of the resist and the etching of the pigment-dispersed coating film can be performed simultaneously.

In the above method, in the case of producing a red filter, it is common to use two or more kinds of pigments for toning in order to obtain the required color characteristics, and conventionally, dianthraquinone was used as the main pigment. Pigments, perylene pigments, diketopyrrolopyrrole pigments and the like are used. In particular, diketopyrrolopyrrole pigments have high lightness and excellent light resistance and heat resistance, so that they are increasingly used as pigments for color filters. Also, CI Pigment Yellow 139 and CI Pigm are used as yellow pigments for toning.
ent Yellow 83 and the like are used.

[0006]

However, as the demand for color filters is increasing day by day, such as increasing the lightness and increasing the color purity, the color characteristics are improved by simply blending the above-mentioned pigments even if they are miniaturized or finely dispersed. There was a limit to.
Therefore, an object of the present invention is to provide a pigment for a color filter which is excellent in heat resistance and light resistance and gives a good red filter having high brightness, a method for producing the same, and a colored composition for a color filter using the pigment.

[0007]

The inventors of the present invention have conducted extensive studies to solve the above-mentioned problems, and as a result, at least two kinds of wavelengths of the minimum transmittance and the maximum transmittance of the spectral transmittance are different. After kneading the mixture of the diketopyrrolopyrrole pigment, the dye derivative, the water-soluble inorganic salt, and the water-soluble organic solvent, the water-soluble inorganic salt and the water-soluble organic solvent are removed to obtain at least two diketopyrrolopyrroles. The present inventors have found that a pigment for a color filter which gives a good red filter with high brightness, which cannot be obtained when the pyrrole-based pigments are separately finely treated and mixed, has been completed, and the present invention has been completed.

That is, the present invention relates to a diketopyrrolopyrrole pigment (A), a diketopyrrolopyrrole pigment (A) and a pigment (A) having different wavelengths of the minimum transmittance and the maximum transmittance in the spectral transmittance ( After kneading a mixture containing B), a dye derivative (C), a water-soluble inorganic salt (D), and a water-soluble organic solvent (E) that does not substantially dissolve the water-soluble inorganic salt (D),
Provided is a pigment for a color filter, which is obtained by removing a water-soluble inorganic salt (D) and a water-soluble organic solvent (E). The present invention also provides a method for producing the above-mentioned color filter pigment. Furthermore, the present invention comprises a colorant carrier comprising a transparent resin, a precursor thereof or a mixture thereof, and the above-mentioned color filter pigment dispersed in the colorant carrier. I will provide a.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The pigment for color filter of the present invention is different in the wavelength of the diketopyrrolopyrrole pigment (A), the pigment (A) and the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance. Kneading a mixture containing a diketopyrrolopyrrole pigment (B), a dye derivative (C), a water-soluble inorganic salt (D), and a water-soluble organic solvent (E) that does not substantially dissolve the water-soluble inorganic salt (D) (Hereinafter, it may be referred to as co-kneading.) After that, the water-soluble inorganic salt (D) and the water-soluble organic solvent (E) are removed to produce the product.

The diketopyrrolopyrrole (hereinafter referred to as DPP) type pigment is a red pigment having a structure represented by the following general formula and has excellent light resistance and heat resistance.

[Chemical 1] In the formula, X ₁ and X ₂ each independently represent —H, an optionally substituted saturated or unsaturated alkyl group, a cyano group, an optionally substituted aryl group, or a halogen group.

The DPP pigment has a wavelength of the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance of 575 nm.
There are reddish pigments and yellowish pigments having a wavelength of the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance of less than 575 nm, and the reddish DPP pigment and the yellowish DPP pigment Not only combination, but also reddish DPP pigments,
It is possible to co-knead the yellowish DPP pigments. In particular, when the reddish DPP-based pigment and the yellowish DPP-based pigment are co-kneaded, that is, the DPP-based pigment (A) has a wavelength of the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance. Reddish DPP of 575 nm or more
The DPP-based pigment (B), which is a system-based pigment, has a wavelength of 57% between the minimum transmittance and the maximum transmittance in the spectral transmittance.
In the case of a yellowish DPP-based pigment having a particle size of less than 5 nm, the effect of the present invention is greater than that in the case of co-king the reddish DPP-based pigments or the yellowish DPP-based pigments, and the brightness is higher. Thus, a good red color filter pigment is obtained.

A specific example of the reddish DPP pigment (A) is shown by color index number, CI Pigment Red2.
54 and 264, and the wavelengths of the intermediate transmittance of the minimum transmittance and the maximum transmittance in the spectral transmittance (hereinafter, referred to as half-value wavelength) are 580 nm and 600 nm, respectively. In the present invention, it is preferable to use CI Pigment Red 254, which has high brightness. When specific examples of yellowish DPP pigments (B) are shown by color index numbers, CI Pigment Red 255 and CI Pigment Orang
e71, half-value wavelengths are 570 nm and 5 respectively.
55 nm. In particular, the reddish DPP pigment (A) is C.
I. Pigment Red 254, and the yellowish DPP pigment (B) is CI Pigment Orange 71 or CI Pigment
Red 255 is preferable because it has a large effect of improving the brightness when co-kneading.

The dye derivative (C) is a compound in which a substituent is introduced into the molecule of an organic dye, and DP at the time of coking.
It serves to suppress the crystal growth of the P-based pigment.
The structure of the organic pigment that is the base of the pigment derivative is DP
P type, quinacridone type, anthraquinone type, perylene type, perinone type, isoindoline type, quinophthalone type,
There are metal complex systems and the like. The organic dye may be a pale yellow aromatic polycyclic compound such as a naphthalene-based or anthraquinone-based compound which is not generally called a dye. Of these, a dye derivative having a DPP-based or quinacridone-based dye as a base skeleton is particularly preferable because it has a high effect of suppressing crystal growth of the DPP-based pigment. Further, as the dye derivative, those having a hue of yellow, orange, and red, which have little influence on the hue of the DPP pigment, are preferably used.

Substituents introduced into the organic dye include a hydroxyl group, a carboxyl group, a sulfonic acid group, a carbamoyl group,
Examples thereof include sulfonamide groups and basic substituents represented by the following general formula.

[Chemical 2] Y: a direct _{bond, -CH 2 NHCOCH 2 -, -} SO 2 NH
-, - CONHOCH ₂ NH-, or - (CH ₂₎ qN
Represents H-. R ₁ and R ₂ : each independently represent a saturated or unsaturated alkyl group which may be substituted, or a heterocyclic ring which may be substituted by R ₁ , R ₂ and which contains a nitrogen, oxygen or sulfur atom.

[0015]

[Chemical 3] Z: a direct _{bond, -SO 2 -, - CO -} , - CH 2 NHCO
_{CH 2 -, - (CH 2} ) q -, - SO 2 NH -, - CON
_{H -, - CH 2 NHCOCH 2} NH-, or - (C
Representing the H ₂₎ qNH-. However, q represents the integer of 1-10. R ₃ , R ₄ , R ₅ , and R ₆ : each independently represent a hydrogen atom, an optionally substituted saturated or unsaturated alkyl group, or an aryl group. R ₇ : represents a saturated or unsaturated alkyl group or aryl group which may be substituted.

Table 1 shows specific examples of the dye derivative.

[Table 1]

DPP derivative (C) used when kneading a mixture of DPP pigment (A), (B) dye derivative (C), water-soluble inorganic salt (D), and water-soluble organic solvent (E)
Is not particularly limited, but the DPP pigment (A),
0.5 to 20% by weight, particularly 2 to 15% by weight, based on the total amount of (B), is preferable. The dye derivative (C)
Since it also has an effect as a dispersant, it is preferable to select one having good dispersibility in a colorant carrier. However, a pigment derivative having a high crystal growth preventing effect and another pigment derivative or a dispersant other than the pigment derivative is preferable. And may be combined. As the dispersant other than the dye derivative, a condensate of ricinoleic acid or 12-hydroxystearic acid, a basic polymer compound, a copolymer containing an acid group, a fatty acid ester, an aliphatic polyamine / polyester graft polymer, polyethylene / A so-called resin type dispersant such as a polypropylene addition polymer can be used. These dispersants are used at the time of co-kneading, or at the time of dispersing the co-kneading pigment in the colorant carrier.

Specific examples of the resin-type dispersant include polycarboxylic acid esters such as polyacrylates, unsaturated polyamides, polycarboxylic acids, polycarboxylic acid (partial) amine salts, polycarboxylic acid ammonium salts, and polycarboxylic acid alkylamines. Salt, polysiloxane, long-chain polyaminoamide phosphate, hydroxyl group-containing polycarboxylic acid ester,
These modified products, amides formed by the reaction of poly (lower alkyleneimine) with polyester having a free carboxyl group, and salts thereof are used. Also,
Water-soluble resin or water-soluble polymer such as (meth) acrylic acid-styrene copolymer, (meth) acrylic acid- (meth) acrylic acid ester copolymer, styrene-maleic acid copolymer, polyvinyl alcohol, polyvinylpyrrolidone Compounds, polyesters, modified polyacrylates, ethylene oxide / propylene oxide adducts, phosphoric acid esters and the like are used. These may be used alone or in admixture of two or more.

The water-soluble inorganic salt (D) functions as a crushing aid, and the DPP-based pigment is crushed by utilizing the high hardness of the inorganic salt during co-kneading, and the primary particles of the DPP-based pigment are finely divided. Be converted. The inorganic salt (D) is not particularly limited as long as it is soluble in water, and sodium chloride, barium chloride, potassium chloride, sodium sulfate or the like can be used, but sodium chloride (salt) is used from the viewpoint of price. Is preferred. The amount of the inorganic salt (D) used during the co-kneading is DP in terms of both treatment efficiency and production efficiency.
It is preferably 1 to 20 times by weight, particularly 3 to 10 times by weight, the total amount of the P-based pigments (A) and (B). This is because the higher the amount ratio of the inorganic salt to the DPP-based pigment is, the higher the micronization efficiency is, but the processing amount of the pigment per one time is reduced.

The water-soluble organic solvent (E) functions to wet the DPP pigments (A), (B), the dye derivative (C) and the water-soluble inorganic salt (D), and dissolves in water ( It is not particularly limited as long as it is mixed (mixed) and does not substantially dissolve the inorganic salt (D) used. However, since the temperature rises during co-kneading and the solvent easily evaporates,
From the viewpoint of safety, a high boiling point solvent having a boiling point of 120 ° C. or higher is preferable. Examples of the water-soluble organic solvent (E) 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 and the like are used.

Fine grained DP during co-kneading
A resin may be used in combination so as to prevent strong aggregation during drying of the P-based pigment and facilitate dispersion in the colorant carrier. A soft powder pigment can be obtained by using a resin together during the co-kneading. As the resin used for the co-kneading, those which are solid at room temperature, water-insoluble, and at least partially soluble in the above-mentioned organic solvent are preferable, and natural resin, modified natural resin, synthetic resin, synthetic modified with natural resin Resin or the like is used. A rosin is typical as the natural resin, and a rosin derivative, a fibrin derivative, a rubber derivative, a protein derivative and an oligomer thereof are used as the modified natural resin. Examples of the synthetic resin include epoxy resin, acrylic resin, maleic acid resin, butyral resin, polyester resin, melamine resin, phenol resin, polyurethane resin, and polyamide resin. Synthetic resins modified with natural resins include rosin-modified maleic acid resin, rosin-modified phenolic resin,
Examples include rosin-modified fumaric acid resin. The amount of the resin used is preferably in the range of 5 to 100% by weight based on the total amount of the DPP pigments (A) and (B).

At the time of co-kneading, in addition to the above resin,
An additive such as a pigment dispersion aid, a plasticizer, or an inorganic pigment such as calcium carbonate, barium sulfate, or silica, which is generally used as an extender pigment, may be used in combination. Further, in order to adjust the hue, the treatment may be carried out by mixing with other pigments.

By dispersing the pigment of the present invention in a colorant carrier composed of a transparent resin, a precursor thereof or a mixture thereof, a colored composition of the present invention used for producing a color filter can be obtained. To disperse the pigment in the color carrier,
Various dispersing means such as a three-roll mill, a two-roll mill, a sand mill and a kneader can be used. Further, in order to improve the dispersion of these, various surfactants, dispersion aids such as dye derivatives, etc. can be added as appropriate. The dispersion aid is excellent in dispersing the pigment, and has a large effect of preventing re-aggregation of the pigment after dispersion. Therefore, when using a coloring composition obtained by dispersing the pigment in a colorant carrier using the dispersion aid. Gives a color filter with excellent transparency.

The transparent resin is 400 to 700 in the visible light range.
The resin has a transmittance of preferably 80% or more, more preferably 95% or more in the entire wavelength region of nm. The transparent resin includes a thermoplastic resin, a thermosetting resin, and a photosensitive resin, and the precursor thereof includes a monomer or an oligomer that is cured by irradiation to generate a transparent resin, and these are used alone or Two or more kinds can be mixed and used. Further, a photoinitiator or the like is added to the colored composition for a color filter of the present invention when the composition is cured by irradiation with ultraviolet rays.

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

As the photosensitive resin, a linear polymer having a reactive substituent such as a hydroxyl group, a carboxyl group and an amino group has a reactive substituent such as an isocyanate group, an aldehyde group and an epoxy group (meth). A resin obtained by reacting an acrylic compound or cinnamic acid to introduce a photocrosslinking group such as a (meth) acryloyl group or a styryl group into the linear polymer is used. In addition, styrene-maleic anhydride copolymer and α
A linear polymer containing an acid anhydride such as an olefin-maleic anhydride copolymer half-esterified with a (meth) acrylic compound having a hydroxyl group such as hydroxyalkyl (meth) acrylate may also be used.

The monomers and oligomers 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,
Various acrylic acid esters and methacrylic acid esters such as melamine (meth) acrylate and epoxy (meth) acrylate, (meth) acrylic acid, styrene, vinyl acetate, (meth) acrylamide, N-hydroxymethyl (meth) acrylamide, acrylonitrile, etc. Can be mentioned.

As the photoinitiator, 4-phenoxydichloroacetophenone, 4-t-butyl-dichloroacetophenone, diethoxyacetophenone, 1- (4-isopropylphenyl) -2-hydroxy-2-methylpropan-1-one, 1 -Hydroxycyclohexyl phenyl ketone, 2-benzyl-2-dimethylamino-1- (4-
Acetophenone photoinitiators such as morpholinophenyl) -butan-1-one, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin photoinitiators such as benzyl dimethyl ketal, benzophenone, benzoylbenzoic acid, benzoyl Benzophenone photoinitiators such as methyl benzoate, 4-phenylbenzophenone, hydroxybenzophenone, acrylated benzophenone, 4-benzoyl-4′-methyldiphenylsulfide, thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, isopropyl Thioxanthone based photoinitiators such as thioxanthone and 2,4-diisopropylthioxanthone, 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-pipenyl-4,6-bis (trichloromethyl) -s-triazine, 2,4-bis (trichloromethyl) -6-styryl s-triazine, 2- (naphth-1-yl)- 4,6-bis (trichloromethyl) -s
-Triazine, 2- (4-methoxy-naphth-1-yl) -4,6-bis (trichloromethyl) -s-triazine, 2,4-trichloromethyl- (piperonyl) -6
A triazine-based photoinitiator such as -triazine and 2,4-trichloromethyl (4'-methoxystyryl) -6-triazine, a carbazole-based photoinitiator, and an imidazole-based photoinitiator are used.

The above photoinitiators may be used alone or in admixture of two or more, and as the sensitizer, α-acyloxime ester, acylphosphine oxide, methylphenylglyoxylate, benzyl, 9,10-phenanthene can be used. Lenquinone, camphorquinone, ethylanthraquinone,
4,4'-diethylisophthalophenone, 3,3 ',
4,4'-Tetra (t-butylperoxycarbonyl)
Compounds such as benzophenone and 4,4′-diethylaminobenzophenone can also be used in combination.

The coloring composition for a color filter of the present invention contains a solvent in order to sufficiently disperse the DPP pigment and to easily coat it on a glass substrate so as to have a dry film thickness of 0.2 to 5 μm. Can be made. 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 acetate, toluene, methyl ethyl ketone, ethyl acetate,
Methanol, ethanol, isopropyl alcohol, butanol, isobutyl ketone, petroleum solvent and the like can be mentioned, and these can be used alone or in combination.

The coloring composition for a color filter of the present invention may contain a yellow pigment depending on the required color characteristics. As a yellow pigment, Pigment Yellow
1, 2, 3, 4, 5, 6, 10, 12, 13, 14, 1
5, 16, 17, 18, 24, 31, 32, 34, 3
5, 35: 1, 36, 36: 1, 37, 37: 1, 4
0, 42, 43, 53, 55, 60, 61, 62, 6
3, 65, 73, 74, 77, 81, 83, 93, 9
4, 95, 97, 98, 100, 101, 104, 10
6, 108, 109, 110, 113, 114, 11
5, 116, 117, 118, 119, 120, 12
3, 126, 127, 128, 129, 138, 13
9, 147, 150, 151, 152, 153, 15
4, 155, 156, 161, 162, 164, 16
6, 167, 168, 169, 170, 171, 17
2,173,174,175,176,177,17
9, 180, 181, 182, 185, 187, 18
8, 193, 194, 199 and the like.

The coloring composition for a color filter of the present invention comprises
It can be prepared in the form of a gravure offset printing ink, a waterless offset printing ink, a silk screen printing ink, a solvent developing type or an alkali developing type colored resist material. The colored resist material is a thermosetting resin,
The pigment for a color filter of the present invention is dispersed in a composition containing a thermoplastic resin or a photosensitive resin, a monomer, and a photoinitiator.

When the coloring composition is prepared in the form of a colored resist material, the color filter pigment of the present invention is preferably contained in the coloring composition in an amount of from 1.5 to 7% by weight, When prepared in the form of printing ink, it is preferably contained in the coloring composition in a proportion of 1.5 to 40% by weight. The colored composition of the present invention may be coarse particles of 5 μm or more, preferably 1 μm or more, more preferably 0.5 μm or more and coarse particles mixed by centrifugation, sintering filter, membrane filter or the like. It is preferable to remove the dust.

The coloring composition prepared as a printing ink is
Since you can pattern by simply printing and drying,
The production of the color filter by the printing method is low in cost and excellent in mass productivity. Further, the development of printing technology enables printing of fine patterns having high dimensional accuracy and smoothness. When a color filter is manufactured by a printing method, it is important to control the fluidity of the ink on a printing machine, and the ink viscosity can be adjusted by a dispersant or an extender pigment.

The coloring composition prepared as a solvent-developing or alkali-developing colored resist material is applied onto a transparent substrate such as a glass plate by a coating method such as spin coating, slit coating or roll coating. Next, after exposing to ultraviolet light through a photomask and washing the unexposed portion with a solvent or an alkali developing solution to form a desired pattern, the same operation is repeated for other colors to produce a color filter. This manufacturing method is called a photolithography method and can manufacture a color filter with higher accuracy than the above printing method.

As the alkaline developer, an aqueous solution of sodium carbonate, sodium hydroxide or the like is used, and an organic alkali such as dimethylbenzylamine or triethanolamine can also be used. Further, an antifoaming agent or a surfactant can be added to the developing solution. In order to increase the ultraviolet exposure sensitivity, after coating and drying the above colored resist agent, a water-soluble or alkali 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. After that, ultraviolet exposure can be performed.

As a method for producing a color filter using a pigment, there are an electrodeposition method, a transfer method and the like in addition to the above, and the coloring composition of the present invention can be used in any method. The electrodeposition method is a method of manufacturing a color filter by utilizing a transparent conductive film formed on a transparent substrate to form a colorant on the transparent conductive film by electrophoretic deposition of colloidal particles. The transfer method is a method in which a color filter layer is previously formed on the surface of a peelable transfer base sheet and the color filter layer is transferred to a desired transparent substrate.

Hereinafter, the present invention will be described based on examples, but the present invention is not limited thereto. In the examples and comparative examples, “part” means “part by weight”. The dye derivatives used in the examples are shown in Table 1.

(Preparation of Acrylic Resin Solution) 450 parts of cyclohexanone were placed in a reaction vessel, heated to 80 ° C. while injecting nitrogen gas into the vessel, and the mixture of the following monomer and thermal polymerization initiator was added at the same temperature for 1 hour. Was added dropwise to carry out a polymerization reaction. Methacrylic acid 20.0 parts Methyl methacrylate 10.0 parts Butyl methacrylate 55.0 parts Hydroxyethyl methacrylate 15.0 parts Azobisisobutyronitrile 4.0 parts After dropping, and further reacting at 80 ° C. for 3 hours, azobis A solution prepared by dissolving 1.0 part of isobutyronitrile in 50 parts of cyclohexanone was added, and the reaction was continued at 80 ° C. for 1 hour to obtain a solution of an acrylic resin having a weight average molecular weight of about 40,000. 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 resin solution synthesized above so that the nonvolatile content became 20% by weight. To prepare an acrylic resin solution.

[Example 1] DPP pigment (“Irgazin DPP RED B manufactured by Ciba Specialty Chemicals”)
O ", CI Pigment Red 254) 106.4 parts, DPP
Pigments (Ciba Specialty Chemicals "Chromophtal DPP Orange TR", CI Pigment Orang
e71) 45.6 parts, DPP dye derivative (e) 8 parts,
1600 parts of sodium chloride and 190 parts of diethylene glycol were charged into a stainless steel 1-gallon kneader (manufactured by Inoue Seisakusho) and kneaded at 60 ° C. for 10 hours. Next, this mixture was poured into 3 liters of warm water and stirred at a high speed mixer for about 1 hour while heating to about 80 ° C. to form a slurry, which was repeatedly filtered and washed with water to remove sodium chloride and the solvent. Dry at ℃ for 1 day, 15
6.8 parts of pigment for color filters was obtained.

A mixture having the following composition containing the obtained pigment was uniformly mixed with stirring, dispersed with a sand mill for 5 hours using glass beads having a diameter of 1 mm, and then filtered with a filter of 5 μm to prepare a DPP pigment dispersion. did. Pigment 9.5 parts DPP-based dye derivative (e) 0.5 part Acrylic resin solution 50.0 parts Cyclohexanone 40.0 parts Then, a mixture having the following composition is stirred and mixed so as to be uniform, and then filtered with a 1 μm filter. Then, an alkali development type red resist material was produced. DPP-based pigment dispersion 60.0 parts Acrylic resin solution 11.0 parts Trimethylolpropane triacrylate 4.2 parts (Shin-Nakamura Chemical's "NK ester ATMPT") Photoinitiator (Ciba Geigy's "Irgacure 907") 1.2 parts Sensitizer ("EAB-F" manufactured by Hodogaya Chemical Co., Ltd.) 0.4 parts Propylene glycol monomethyl ether acetate 23.2 parts

[Example 2] DPP pigment "Irgazin D"
Example 1 except that 106.4 parts of "PP RED BO" was replaced with 144.4 parts and 45.6 parts of DPP-based pigment "Chromophtal DPP Orange TR" was replaced with 7.6 parts.
A pigment for a color filter was obtained in the same manner as in. Using the obtained pigment, an alkaline development type red resist material was produced in the same manner as in Example 1.

[Example 3] The DPP pigment "Chromophtal DPP Orange TR" was replaced with a DPP pigment ("Irgazin DPP Scarlet EK" manufactured by Ciba Specialty Chemicals, CI Pigment Red 255).
A pigment for a color filter was obtained in the same manner as in Example 1 except that 2.4 parts of 8 parts of the system dye derivative (e) were replaced with the quinacridone dye derivative (f). Using the obtained pigment, 0.15 out of 0.5 parts of the DPP dye derivative (e) was used.
Except that the quinacridone dye derivative (f) was used in place of
In the same manner as in Example 1, an alkali development type red resist material was produced.

Example 4 Two kinds of DPP pigments were used as DPP.
Pigments (“Irgazin DPP RED BO” manufactured by Ciba Specialty Chemicals, CI Pigment Red 254)
136.8 parts and a DPP pigment (“Irgazin DPP Rubin TR” manufactured by Ciba Specialty Chemicals, C.I.
I. Pigment Red 264) A pigment for color filter was obtained in the same manner as in Example 1 except that 15.2 parts were used. Using the obtained pigment, an alkaline development type red resist was prepared in the same manner as in Example 1.

[Comparative Example 1] Two DPP pigments were replaced with one DPP pigment "Irgazin DPP RED BO" 15
Micronization was performed in the same manner as in Example 1 except that 2 parts were used.
CI Pigment Red 254 pigment (hereinafter referred to as miniaturized PR254
It is called a pigment. ) Got. In addition, two types of DPP pigment
DPP pigment "Chromophtal DPP Orange T"
R ”152 parts, except that the CI Pigment Orange 71 pigment was miniaturized in the same manner as in Example 1 (hereinafter referred to as the miniaturized P
It is called O71 pigment. ) Got. A mixture having the following composition containing the obtained pigment was uniformly stirred and mixed, and dispersed with a sand mill for 5 hours using glass beads having a diameter of 1 mm, and then 5 μ
A DPP-based pigment dispersion was prepared by filtering with a filter of m, and using this, an alkaline development type red resist material was obtained in the same manner as in Example 1. Micronized PR254 pigment 6.65 parts Micronized PO71 pigment 2.85 parts DPP dye derivative (e) 0.5 parts Acrylic resin solution 50.0 parts Cyclohexanone 40.0 parts

[Comparative Example 2] A mixture having the following composition was uniformly stirred and mixed, and the mixture was dispersed for 5 hours by a sand mill using glass beads having a diameter of 1 mm, and then filtered with a filter of 5 μm D
A PP-based pigment dispersion was prepared, and using this, an alkaline development type red resist material was obtained in the same manner as in Example 1. Micronized PR254 pigment 9.02 parts Micronized PO71 pigment 0.48 part DPP dye derivative (e) 0.5 part Acrylic resin solution 50.0 part Cyclohexanone 40.0 part

[Comparative Example 3] Two DPP-based pigments were replaced with one DPP-based pigment "Irgazin DPP Scarlet EK" 1
CI Pigment Red 255 pigment (hereinafter, referred to as "Pigment Red Pigment 255", which was miniaturized in the same manner as in Example 1, except that the DPP dye derivative (e) was replaced with the quinacridone dye derivative (f) instead of 52 parts.
It is called a miniaturized PR255 pigment. ) Got. A mixture having the following composition was uniformly mixed by stirring, dispersed with a sand mill for 5 hours using glass beads having a diameter of 1 mm, and then filtered with a filter of 5 μm to prepare a DPP-based pigment dispersion, which was used in Example 1 An alkaline development type red resist material was obtained in the same manner as in. Micronized PR254 pigment 6.65 parts Micronized PR255 pigment 2.85 parts DPP dye derivative (e) 0.35 part Quinacridone dye derivative (f) 0.15 part Acrylic resin solution 50.0 parts Cyclohexanone 40.0 parts

[Comparative Example 4] One type of DPP-based pigment "Irgadine DPP Rubin TR" 152 was prepared from two types of DPP-based pigments.
C. refined in the same manner as in Example 1 except that the C.
I. Pigment Red 264 pigment (hereinafter referred to as micronized PR264 pigment) was obtained. A mixture having the following composition was uniformly stirred and mixed, and then dispersed with a sand mill for 5 hours using glass beads having a diameter of 1 mm, and then filtered with a filter of 5 μm and DP
A P-based pigment dispersion was prepared, and using this, an alkaline development type red resist material was obtained in the same manner as in Example 1. Micronized PR254 pigment 8.55 parts Micronized PR264 pigment 0.95 part DPP dye derivative (e) 0.5 part Acrylic resin solution 50.0 parts Cyclohexanone 40.0 parts

The obtained resist material was treated with 100 mm × 10
On a glass substrate of 0 mm and 1.1 mm thickness, using a spin coater, 500 rpm, 1000 rpm, 1500 r
The coating was performed at a rotation speed of 2,000 rpm and pm to obtain four types of coated substrates having different film thicknesses. Next, after drying at 70 ° C. for 20 minutes,
Ultraviolet light exposure was performed using an ultrahigh pressure mercury lamp with an integrated light amount of 150 mJ. After exposure, after heating at 230 ° C. for 1 hour and allowing to cool, a microspectrophotometer (“OSP-S manufactured by Olympus Optical Co., Ltd.
P100 ") was used to measure the chromaticity (Y, x, y) of the obtained coating film with a C light source. The chromaticity at x = 0.600 was calculated from the four sets of chromaticity / spectroscopic measurement results. The results are shown in Table 2.

[0050]

[Table 2]

A coating film formed by using pigments (Examples 1 to 4) obtained by co-kneading two types of DPP pigments having different half-value wavelengths was prepared by finely dividing the two types of pigments and then mixing them. The pigments (Comparative Examples 1 to 4) formed with the above-mentioned pigments have the same chromaticity and higher brightness (Y value) than the coating film.

[0052]

According to the present invention, a diketopyrrolopyrrole pigment for a color filter having high lightness and excellent color characteristics can be obtained. Further, by using the coloring composition containing the pigment of the present invention, it has become possible to obtain a color filter having an excellent filter segment that has both high transmittance and high color purity.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁷ Identification code FI theme code (reference) // G02F 1/1335 505 G02F 1/1335 505 F term (reference) 2H025 AA10 AB13 AC01 AD01 BC32 BC42 BC52 BC53 BC54 CA01 CA28 CC12 FA03 FA17 2H048 BA43 BA45 BA47 BA48 BA55 BA57 BA62 2H091 FA02Y FB04 FB12 FC10 FD04 LA04 LA15 LA30

Claims (6)

[Claims] 1. A diketopyrrolopyrrole pigment (A), a pigment
(A) and diketopyrrolopyrrole pigments having different wavelengths of the minimum transmittance and the maximum transmittance in the spectral transmittance
After mixing a mixture containing (B), a dye derivative (C), a water-soluble inorganic salt (D), and a water-soluble organic solvent (E) that does not substantially dissolve the water-soluble inorganic salt (D), the water-soluble inorganic salt A pigment for a color filter, characterized in that the salt (D) and the water-soluble organic solvent (E) are removed. 2. A diketopyrrolopyrrole pigment (A), which is a reddish diketopyrrolopyrrole pigment having a wavelength of 575 nm or more of the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance, Ketopyrrolopyrrole pigment (B)
The pigment for a color filter according to claim 1, which is a yellowish diketopyrrolopyrrole pigment having a wavelength of the intermediate transmittance between the minimum transmittance and the maximum transmittance in the spectral transmittance of less than 575 nm. 3. Reddish diketopyrrolopyrrole pigment (A)
Is CI Pigment Red 254, and the yellowish diketopyrrolopyrrole pigment (B) is CI Pigment Orange 71 or CI Pigment Red 255. 3. The color filter pigment according to claim 2, wherein 4. The pigment for a color filter according to claim 1, wherein the dye derivative (C) is a quinacridone derivative and / or a diketopyrrolopyrrole derivative. 5. The method for producing a pigment for a color filter according to claim 1. 6. A colorant carrier comprising a transparent resin, a precursor thereof or a mixture thereof, and the color filter pigment according to any one of claims 1 to 4 dispersed in the colorant carrier. A characteristic coloring composition for a color filter.