JP2016114887A - Color filter pigment composition and color filter - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide: a color filter organic pigment composition that contains an organic pigment dispersant having low viscosity and is capable of keeping high brightness even after going through a heat history at high temperature while producing a color filter and providing only a small change in hue of an image before and after going through the heat history; a manufacturing method therefor; and a color filter containing such a pigment composition in pixel portions thereof.SOLUTION: Disclosed is a color filter organic pigment composition that contains 0.1-15 pts.mass of a polyamide-imide resin (B) per 100 pts.mass of an organic pigment (A). A color filter containing such a color filter organic pigment composition in pixel portions thereof is also disclosed.SELECTED DRAWING: None

Description

  The present invention can obtain an image having a low viscosity organic pigment dispersion, a high brightness after receiving a heat history at a high temperature when forming a color filter, and a small hue change before and after receiving the heat history. The present invention relates to an organic pigment composition for a color filter, a method for producing the same, and a color filter containing the pigment composition in a pixel portion.

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.

  The organic pigment used to create the color filter has characteristics that are completely different from those of conventional general-purpose applications. Specifically, the display screen of the liquid crystal display device can be seen more clearly (high contrast), or the same display screen. There is a demand for making the image brighter (higher brightness). In order to meet such demands, powdered organic pigments that have been refined to have an average primary particle size of 100 nm or less are frequently used.

However, on the other hand, as the miniaturization progresses, the surface area of the pigment increases, so that the surface energy increases and the dispersion viscosity of the pigment dispersion increases. In addition, there is a problem that the organic pigment agglomerates due to the thermal history at the time of forming the color filter, resulting in a decrease in luminance and contrast.
Therefore, in order to impart dispersibility and heat resistance, surface treatment with an organic pigment derivative, a surfactant, or a synthetic resin is often performed. By this surface treatment, the dispersibility, dispersion stability, and heat resistance of the organic pigment that has not been subjected to any surface treatment can be improved.

  Known surface treatment methods include kneading, acid / alkali precipitation, and pressure heating. Specifically, a method of solvent salt milling an organic pigment in the presence of an acrylic resin is known.

The surface treatment of organic pigments with synthetic resins has been studied according to general polymer categories such as (meth) acrylic resins, epoxy resins, polyester resins, polyurethane resins, etc. Systematically examine whether the polymers of the above are highly effective in improving dispersibility and dispersion stability, and what type of polymer is selectively the most effective in the same category of polymers. However, there are many unclear points.
However, since fine organic pigments are more likely to aggregate than general-purpose organic pigments, the surface treatment of organic pigments used in general-purpose applications does not necessarily require surface treatment using any synthetic resin. However, the improvement effect as expected is not obtained, and the actual condition is that the synthetic resin having the optimum structure in the optimum category is selected by trial and error.

  Specifically, for example, as a surface treatment method of an organic pigment used for preparing a color resist for a color filter, a method of solvent salt milling a rosin ester and an organic pigment is known (Patent Document 1). Moreover, as a synthetic resin used for the surface treatment of the organic pigment, two or more types of (meth) acrylic acid esters containing an epoxy group and / or an α-chlorohydrin group and having different side chain carbon atoms are used. A polymer obtained by polymerizing a monomer mixture containing is known (Patent Document 2).

JP-A-8-179111 JP 2013-228714 A

However, by the solvent salt milling described above, a single monomer containing two or more types of (meth) acrylic acid esters containing the above-described epoxy group and / or α-chlorohydrin group and having different number of carbon atoms in the side chain. Organic pigments obtained by polymerizing the polymer mixture on the pigment surface are still lacking in brightness and heat resistance to achieve the required level of optical properties that are constantly being improved. In addition, the viscosity of the organic pigment dispersion is high.
The present invention can obtain an image having a low viscosity organic pigment dispersion, a high brightness after receiving a heat history at a high temperature when forming a color filter, and a small hue change before and after receiving the heat history. An organic pigment composition for a color filter, a production method thereof, and a color filter containing the pigment composition in a pixel portion are provided.

  Therefore, the present inventors diligently studied the surface treatment effect of the organic pigment using various synthetic resins in order to solve the above-mentioned problems, and when the surface treatment was carried out with a polyamideimide resin, the above-mentioned drawbacks were solved. A color filter capable of obtaining a colored product, in particular, a color filter capable of liquid crystal display excellent in luminance and heat resistance in a color filter used in a liquid crystal display device exposed to a high temperature for a long time in a manufacturing process or use condition. As a result, the present invention has been completed.

  That is, this invention contains 0.1-15 parts of polyamide imide resins (B) per 100 parts of organic pigments (A) by mass conversion, The organic pigment composition for color filters characterized by the above-mentioned.

An organic pigment composition for a color filter, wherein the polyamideimide resin (B) is treated on the surface of pigment particles of the organic pigment (A).

  In addition, the polyamideimide resin (B) comprises an aliphatic isocyanate compound and / or an alicyclic isocyanate compound having two or more isocyanate groups in the molecule, a tricarboxylic acid anhydride and / or a tetracarboxylic acid anhydride. An organic pigment composition for a color filter, which is a polyamideimide resin obtained by reaction.

The polyamideimide resin (B) is reacted with an isocyanurate type polyisocyanate synthesized from an isocyanate having an aliphatic structure and a tricarboxylic acid anhydride to form a polyamideimide resin, and then reacted with an alcohol compound. An organic pigment composition for a color filter, which is an alcohol-modified polyamideimide resin obtained.

A method for producing an organic pigment composition for a color filter, comprising subjecting the organic pigment (A) to solvent salt milling in the presence of the polyamideimide resin (B).

A color filter comprising the organic pigment composition for a color filter in a pixel portion.

Furthermore, the present invention relates to a color filter comprising a pixel portion containing the organic pigment composition for a color filter obtained by the production method.

Since the organic pigment composition of the present invention contains the organic pigment (A) and the specific polyamideimide resin (B) at a predetermined ratio, the dispersibility of the organic pigment is improved and the organic pigment dispersion having a low viscosity is performed. It has a particularly remarkable technical effect that the body can be obtained.
Since the organic pigment composition of the present invention contains the organic pigment (A) and the specific polyamideimide resin (B) in a predetermined ratio, the color difference of the colored material is not affected even when the thermal history is received for a long time. There is a particularly remarkable technical effect that a small colored product having excellent coloring heat resistance can be obtained.
Moreover, the manufacturing method of the organic pigment composition of the present invention has a particularly remarkable technical effect that the above-described organic pigment composition can be easily obtained.
Furthermore, since the color filter of the present invention contains the above-described organic pigment composition or the organic pigment composition obtained by the above-described manufacturing method in the pixel portion, it is particularly prominent that liquid crystal display superior in luminance is possible. Has a technical effect.

  The organic pigment composition of the present invention contains 0.1 to 15 parts of polyamideimide resin (B) per 100 parts of organic pigment (A) in terms of mass.

  As the organic pigment (A), any known and conventional ones can be mentioned. For example, phthalocyanine pigment, dioxazine pigment, azo pigment, quinacridone pigment, selenium pigment, perylene pigment, perinone pigment, phthalone pigment, isoindoline pigment, isoindolinone pigment, methine / azomethine pigment, anthraquinone pigment, thioindigo pigment, metal complex pigment or Organic pigments such as diketopyrrolopyrrole pigments can be mentioned. Examples of phthalocyanine pigments include copper phthalocyanine, metal-free phthalocyanine, zinc phthalocyanine, cobalt phthalocyanine, nickel phthalocyanine, iron phthalocyanine, and halogenated halogenated phthalocyanines. Examples of phthalocyanines and azo pigments include azo lake pigments, insoluble azo pigments, and condensed azo pigments. Examples of anthraquinone pigments include aminoanthraquinone and diaminodianthracite. Emissions, anthrapyrimidine, flavanthrone, anthanthrone, indanthrone, pyranthrone, violanthrone, and the like, or, acetylene black, channel black, carbon black such as furnace black, can be used other organic pigments in general.

  Specifically, examples of the quinacridone pigment include C.I. I. Pigment Violet 19, 42, C.I. I. Pigment Red 122, 202, 206, 207, 209, C.I. I. Pigment Orange 48, 49 and the like.

  Examples of the phthalocyanine pigment include C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16 and C.I. I. Pigment Green 7, 36, 58, 59, and the like.

  Examples of selenium pigments include C.I. I. Pigment Blue 60, C.I. I. Pigment Yellow 24, 108, C.I. I. Pigment Red 168, 177, C.I. I. Pigment Orange 40 and the like.

Examples of perylene / perinone pigments include C.I. I. Pigment Violet 29, C.I. I. Pigment Red 123, 149, 178, 179, C.I. I. Pigment Black 31, 32, C.I. I. Pigment Orange 43 and the like.

  Examples of the phthalone pigment include C.I. I. And pigments such as Pigment Yellow 138.

  Examples of the dioxazine pigment include C.I. I. Pigment Violet 23, 37, C.I. I. Pigment Blue 80 or the like.

  Examples of isoindolinone pigments include C.I. I. Pigment Yellow 109, 110, 173, C.I. I. Pigment Orange 61 and the like.

  Examples of methine / azomethine pigments include C.I. I. Pigment Yellow 139, 185, C.I. I. Pigment Orange 66, C.I. I. And pigments such as Pigment Brown 38.

  Examples of the metal complex pigment include C.I. I. Pigment Yellow 150, 129, C.I. I. Pigment Orange 68, C.I. I. And pigments such as Pigment Red 257.

  Examples of the diketopyrrolopyrrole pigment include C.I. I. Pigment Red 254, 255, C.I. I. Pigment Orange 71, 72 and the like.

  Examples of the azo lake pigment include C.I. I. Pigment Red 48: 1, 48: 2, 48: 3, 48: 4, 48: 5, 49: 1, 49: 2, 49: 3, 50: 1, 51: 1 52: 1, 52: 2, 53: 1, 57: 1, 58: 2, 58: 4, 60: 1, 63: 1, 63: 2, 64: 1 200, 211, 238, 239, 240, 243, 245, 247, C.I. I. Pigment Yellow 61, 62: 1, 104, 133, 168, 169, 183, 190, 191, C.I. I. Pigment Orange 17, 17: 1, 19 and 46, and the like.

  Examples of insoluble azo pigments include C.I. I. Pigment Yellow 1, 3, 12, 13, 14, 17, 55, 73, 74, 81, 83, 97, 130, 151, 152, 154, 156, 165, 166, 167, 170, 171, 172, 174, 175, 176, 180, 181, 188, C.I. I. Pigment Orange 16, 36, 60, C.I. I. Pigment Red 5, 22, 22, 31, 112, 146, 150, 171, 175, 176, 183, 185, 208, 213, C.I. I. PigmentViolet 43, 44, C.I. I. Pigment Blue 25, 26 and the like.

  Examples of the condensed azo pigment include C.I. I. Pigment Yellow 93, 94, 95, 128, 166, C.I. I. Pigment Orange 31, C.I. I. Pigment Red 144, 166, 214, 220, 221, 242, 248, 262, C.I. I. Pigment Brown 41, 42 and the like.

  Since the organic pigment (A) in the present invention is required to have high luminance and high contrast as a color filter, the average particle diameter of the primary particles is preferably 100 nm or less, and more clearly when it is 80 nm or less. Since it is easy to obtain a colored product, it is more preferable. On the other hand, since the organic pigment (A) having a smaller particle diameter generally has lower heat resistance, it is necessary to improve the heat resistance by some means without impairing the sharpness.

  In the present invention, the average particle diameter of primary particles is measured as follows. First, the particle | grains in a visual field are image | photographed with a transmission electron microscope or a scanning electron microscope. And the longest length (maximum length) of the internal diameter of each particle | grain is calculated | required about 50 of the primary particles which comprise the aggregate on a two-dimensional image. The average value of the maximum length of each particle is defined as the average particle size of the primary particles.

  In addition, as the polyamideimide resin (B) in the present invention, any known and conventional one can be used.

The polyamide-imide resin (B) in the present invention comprises an aliphatic isocyanate compound and / or alicyclic isocyanate compound (b-1) having two or more isocyanate groups in the molecule, a tricarboxylic acid anhydride and / or a tetracarboxylic acid. Polyamideimide resin obtained by reacting with an acid anhydride may be used.

The aliphatic isocyanate compound and / or alicyclic isocyanate compound (b-1) having two or more isocyanate groups in the molecule may be an isocyanurate type polyisocyanate.

The polyamideimide resin (B) may be a carboxylimide or acid anhydride group-containing polyamideimide resin having an acid value of 60 to 210 KOHmg / g.

The polyamide-imide resin (B) is composed of an aliphatic isocyanate compound having two or more isocyanate groups in the molecule and / or an alicyclic isocyanate compound (b-1), a diisocyanate monomer (b-2) and an isocyanurate type. The polyisocyanate (b-3) or the isocyanurate type polyisocyanate (b-3) alone, and the diisocyanate monomer (b-2) and the isocyanurate type polyisocyanate (b-3) The weight ratio ((b-2) / (b-3)) may be 0 to 0.5.

The polyamide-imide resin (B) reacts with an isocyanurate-type polyisocyanate (b-4) synthesized from an isocyanate having an aliphatic structure and a tricarboxylic acid anhydride (b-5) to react with the polyamide-imide resin (b- After producing 6), an alcohol-modified polyamideimide resin obtained by reacting the alcohol compound (b-7) may be used. Further, the reaction between the polyamideimide resin (b-6) and the alcohol compound (b-7) is performed by reacting the acid anhydride group mole number (M1) in the polyamideimide resin (b-6) with the alcohol compound (b-7). ) May be in a range of M1 / L = 0.1-5 with the number of moles of hydroxyl group (L).

In the measurement of infrared absorption spectrum, the polyamideimide resin (B) reacts an isocyanurate type polyisocyanate (b-4) synthesized from an isocyanate having an aliphatic structure with a tricarboxylic acid anhydride (b-5). It may be obtained by reacting an alcohol compound (b-7) with a polyamide-imide resin in which 2270 cm ^−1, which is a characteristic absorption of an isocyanate group, has disappeared.

Number of moles of isocyanate group (N) of isocyanurate type polyisocyanate (b-4) synthesized from isocyanate having aliphatic structure and number of moles of carboxy group of tricarboxylic acid anhydride (b-5) (M2) And the ratio [(M2) + (M3)) / (N)] of the total number of moles of acid anhydride groups (M3) may be 1.1-3.

The tricarboxylic acid anhydride (b-5) may be a tricarboxylic acid anhydride having an aliphatic structure. Furthermore, the isocyanurate type polyisocyanate compound (b-4) is an isocyanurate type polyisocyanate synthesized from an isocyanate having a cyclic aliphatic structure, and the tricarboxylic acid anhydride (b-5) having an aliphatic structure is a ring. It may be a tricarboxylic acid anhydride having a formula aliphatic structure.

The isocyanurate type polyisocyanate compound having a cycloaliphatic structure is an isocyanurate type triisocyanate (including a polymer such as a pentamer) synthesized from isophorone diisocyanate, and a tricarboxylic acid having a cycloaliphatic structure The anhydride may be cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride.

Examples of the isocyanate compound used in the present invention include isophorone diisocyanate (IPDI), hexamethylene diisocyanate (HDI), 4,4′-dicyclohexylmethane diisocyanate, hydrogenated xylene diisocyanate (HXDI), norbornylene diisocyanate (NBDI), Lysine diisocyanate, IPDI3N (isocyanurate-type triisocyanate of isophorone diisocyanate), HDI3N (isocyanurate-type triisocyanate of hexamethylene diisocyanate), HXDI3N (isocyanurate-type triisocyanate of hydrogenated xylene diisocyanate), NBDI3N (isocyanurate type of norbornane diisocyanate) Triisocyanate), isocyanurate synthesized from HDI3N Type triisocyanate, HTMDI3N (isocyanurate type triisocyanate synthesized from trimethylhexamethylene diisocyanate, HMDI3N (isocyanurate type triisocyanate synthesized from hydrogenated diphenylmethane diisocyanate), p-phenylene diisocyanate, m-phenylene diisocyanate, p-xylene Diisocyanate, m-xylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 3,3'-dimethyldiphenyl-4,4'-diisocyanate, 3,3 ' -Diethyldiphenyl-4,4'-diisocyanate, m-xylene diisocyanate, p-xylene diisocyanate, naphthalene diisocyanate Sulfonates, and the like. In addition, adducts obtained by the urethanization reaction of biuret and the isocyanate compound and various polyols of the isocyanate compounds can also be used.

Examples of the tricarboxylic acid anhydride or tetracarboxylic acid anhydride used in the present invention include tricarboxylic acid anhydrides such as trimellitic anhydride and naphthalene-1,2,4-tricarboxylic acid anhydride; pyromellitic dianhydride Benzophenone-3,3 ′, 4,4′-tetracarboxylic dianhydride, diphenyl ether-3,3 ′, 4,4′-tetracarboxylic dianhydride, benzene-1,2,3,4-tetra Carboxylic dianhydride, biphenyl-3,3'4,4'-tetracarboxylic dianhydride, biphenyl-2,2'3,3'-tetracarboxylic dianhydride, naphthalene-2,3,6 7-tetracarboxylic dianhydride, naphthalene-1,2,4,5-tetracarboxylic dianhydride, naphthalene-1,4,5,8-tetracarboxylic dianhydride, decahydronaphth Len-1,4,5,8-tetracarboxylic dianhydride, 4,8-dimethyl-1,2,3,5,6,7-hexahydronaphthalene-1,2,5,6-tetracarboxylic acid Dianhydride, 2,6-dichloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 2,7-dichloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, 2, 3,6,7-tetrachloronaphthalene-1,4,5,8-tetracarboxylic dianhydride, fetentylene-1,3,9,10-tetracarboxylic dianhydride, berylene-3,4,9, 10-tetracarboxylic dianhydride, bis (2,3-dicarboxyphenyl) methane dianhydride, bis (3,4-dicarboxyphenyl) methane dianhydride, 1,1-bis (2,3-di Carboxyphenyl) ethane dianhydride, 1,1- (3,4-dicarboxyphenyl) ethane dianhydride, 2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 2,3-bis (3,4-dicarboxyphenyl) propane dianhydride Anhydride, bis (3,4-dicarboxyphenyl) sulfone dianhydride, bis (3,4-dicarboxyphenyl) ether dianhydride, propanetricarboxylic acid anhydride, cyclohexanetricarboxylic acid anhydride (cyclohexane-1,3 , 4-tricarboxylic acid-3,4-anhydride, cyclohexane-1,3,5-tricarboxylic acid-3,5-anhydride, cyclohexane-1,2,3-tricarboxylic acid-2,3-anhydride, etc.) , Methylcyclohexane tricarboxylic acid anhydride, cyclohexene carboxylic acid anhydride, methyl cyclohexene carboxylic acid anhydride, and the like. It is possible to use 1 type (s) or 2 or more types. Further, a tricarboxylic acid anhydride and a tetracarboxylic acid anhydride may be mixed and used. In some cases, bifunctional dicarboxylic acid compounds such as adipic acid, sebacic acid, phthalic acid, fumaric acid, maleic acid and acid anhydrides thereof may be used in combination.

Examples of the alcohol compound used in the present invention include methyl alcohol, ethyl alcohol, n-propyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, t-butyl alcohol, ethylene glycol, propylene glycol, trimethylolpropane, and benzyl alcohol. Alcohols having 10 or less carbon atoms such as 2-methoxyethyl alcohol, 2-ethoxyethyl alcohol, 1-methoxy-2-propyl alcohol, 1-ethoxy-2-propyl alcohol, 3-methoxy-1-butyl alcohol, 2 -An alcohol having 10 or less carbon atoms containing an ether bond such as isopropoxyethyl alcohol; an alcohol containing 10 or less carbon atoms such as 3-hydroxy-2-butanone; Carbon atoms containing ester groups such as Le is 10 ppm alcohol are exemplified. In the present invention, it is preferable to use a monohydric alcohol having 10 or less carbon atoms. Furthermore, monohydric alcohols having 5 or less carbon atoms are preferred.

  The organic pigment composition of the present invention is characterized by containing 0.1 to 15 parts of polyamideimide resin (B) per 100 parts of organic pigment (A) in terms of mass. By including 2 to 14 parts, especially 3 to 13 parts of polyamideimide resin (B) per part, technical effects in the present invention, and other technical effects such as dispersibility and dispersion stability in the medium to be colored The organic pigment composition having the most balanced economic efficiency is preferable.

  Such an organic pigment composition of the present invention can be prepared by mixing the organic pigment (A) and the polyamideimide resin (B) by any means. As a simple preparation method, for example, a method of mixing the organic pigment (A) and the polyamideimide resin (B), and mixing and stirring the organic pigment (A) in the liquid medium solution of the polyamideimide resin (B), There are methods such as filtration and drying.

  However, the present inventors have been able to expect a stronger interaction between the organic pigment (A) and the polyamideimide resin (B) than the simple preparation method described above, specifically, the polyamideimide resin (B The organic pigment composition prepared by solvent salt milling of the organic pigment (A) in the presence of) has a greater heat resistance improvement than the organic pigment composition prepared by the simple method described above. It was found that the effect was achieved. Hereinafter, this preparation method is referred to as a solvent salt milling method.

  The above-described adjustment method of the present invention includes the organic pigment (A) as the phthalocyanine pigment, dioxazine pigment, azo pigment, quinacridone pigment, selenium pigment, perylene pigment, perinone pigment, phthalone pigment, isoindoline pigment, isoindolinone pigment, methine Organic pigments such as azomethine pigments, anthraquinone pigments, thioindigo pigments, metal complex pigments or diketopyrrolopyrrole pigments can be mentioned. Examples of phthalocyanine pigments include copper phthalocyanine, metal-free phthalocyanine, zinc phthalocyanine, cobalt phthalocyanine, nickel phthalocyanine, iron Phthalocyanines, etc., halogenated phthalocyanines halogenated from these phthalocyanines, azo pigments such as azo lake pigments, insoluble azo pigments, condensed azo pigments, anthraquinone pigments Especially excellent for obtaining carbon black such as noanthraquinone, diaminodianthraquinone, anthrapyrimidine, flavantron, anthanthrone, indanthrone, pyranthrone, violanthrone, acetylene black, channel black, furnace black, and other organic pigments in general. Manufacturing method.

  The solvent salt milling method will be described. According to the solvent salt milling method, the organic pigment (A) and the polyamide-imide resin (B) are kneaded by applying mechanical stress with a water-soluble inorganic salt and a water-soluble organic solvent. The surface of the organic pigment (A) can be uniformly and reliably coated with the polyamideimide resin (B) after reducing the diameter and making the particle shape substantially cubic.

  Specifically, in this solvent salt milling, an organic pigment, a water-soluble inorganic salt, and a water-soluble organic solvent that does not dissolve the organic pigment are charged into a kneader, and kneading and grinding are performed therein.

  When an organic pigment composition is prepared from the organic pigment (A) and the polyamideimide resin (B) by the solvent salt milling method, the final organic pigment composition is polyamide per 100 parts of the organic pigment (A). Although both are charged so that it may become 0.1-15 parts of imide resin (B), since the interaction including adsorption | suction between an organic pigment (A) and a polyamide-imide resin (B) is strong, it charged. Polyamideimide resin (B) hardly flows out and remains in the organic pigment (A).

  As the water-soluble inorganic salt, for example, inorganic salts such as sodium chloride, potassium chloride, sodium sulfate and the like are preferably used. Moreover, it is more preferable to use an inorganic salt having an average particle size of 0.5 to 50 μm. Such an inorganic salt can be easily obtained by pulverizing a normal inorganic salt.

  Further, the amount of the inorganic salt used is preferably 2 to 20 parts, more preferably 4 to 16 parts, and more preferably 6 to 12 parts relative to 1 part of the organic pigment (A) in terms of mass. Is more preferable.

  As the water-soluble organic solvent, those capable of suppressing crystal growth can be suitably used. For example, diethylene glycol, glycerin, ethylene glycol, propylene glycol, liquid polyethylene glycol, liquid polypropylene glycol, 2- (methoxymethoxy) ethanol, 2-butoxy Ethanol, 2- (isopentyloxy) ethanol, 2- (hexyloxy) ethanol, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol, triethylene glycol monomethyl ether, 1-methoxy-2- Propanol, 1-ethoxy-2-propanol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene Recall monomethyl ether, dipropylene glycol, triethylene glycol, polyethylene glycol, 1,2-propanediol, 1-methoxy-2-but-propanol or the like can be used, ethylene glycol or diethylene glycol are preferred.

  Although the usage-amount of the said water-soluble organic solvent is not specifically limited, 0.01-5 parts is preferable with respect to 1 part of organic pigments (A) in conversion of mass.

  The kneading temperature is preferably between 0 and 150 ° C. Since the deterioration of heat resistance, contrast and the like, which will be described later, can be reduced, the organic pigment composition thus obtained is preferable for a color filter.

  As an apparatus used for this kneading, there is a kneader, a mix muller, Trimix (trade name) manufactured by Inoue Seisakusho, which is a planetary mixer described in JP-A-2007-100008, and JP-A-4-122778. The continuous twin-screw extruder described above, Miracle KCK manufactured by Asada Tekko Co., Ltd., which is a continuous single-screw kneader described in JP-A-2006-306996, and the like can be used.

  In the solvent salt milling method, the mixture that has been heated or kneaded in a liquid medium is cooled, for example, and the liquid medium is removed therefrom, and if necessary, the solid is washed, filtered, dried, pulverized, etc. By doing this, the powder of the organic pigment composition of the present invention containing the organic pigment (A) and the polyamideimide resin (B) can be obtained.

  As washing, either water washing or hot water washing can be employed. The number of washings can be repeated in the range of 1 to 5 times. By washing, the polyamideimide resin (B) not adsorbed on the organic pigment (A) can be easily removed. If necessary, acid cleaning, alkali cleaning, and solvent cleaning may be performed so as not to change the crystal state. The amount (so-called yield) of the polyamideimide resin (B) which is an active ingredient contained in the organic pigment composition is, for example, from the amount of polyamideimide resin extracted by solvent extraction of the organic pigment composition, or the charged polyamideimide resin It can obtain | require from the outflow amount in the filtrate with respect to (B).

  Examples of the drying after filtration and washing described above include batch-type or continuous drying in which the pigment is dehydrated and / or desolvated by heating at 80 to 120 ° C. with a heating source installed in a dryer. Examples of the dryer generally include a box dryer, a band dryer, and a spray dryer. In particular, spray dry drying is preferable because it is easily dispersed during paste preparation. In addition, the pulverization after drying is not an operation for increasing the specific surface area or reducing the average particle diameter of the primary particles, but for example, the pigment is a lamp as in the case of drying using a box dryer or a band dryer. When it becomes a shape, etc., it is performed in order to break the pigment into powder, and examples thereof include mortar, hammer mill, disc mill, pin mill, jet mill and the like. In this way, a dry powder containing an organic pigment composition containing the organic pigment (A) and the polyamideimide resin (B) as a main component is obtained.

  The organic pigment composition in the present invention has high dispersibility and dispersion stability in a liquid medium, and the pigment dispersion has a low viscosity and is dispersed in fine particles, so it is stable with high Newtonian fluidity. For example, when a color filter pixel portion is manufactured from this, a color filter having high brightness, contrast, and high light transmittance can be obtained by forming a uniform coating film.

  In the organic pigment composition of the present invention thus obtained, the colored material when the medium to be colored is colored is clear and excellent in saturation, and the hue of the colored material does not change greatly even when subjected to heat history for a long time. Excellent heat resistance. Therefore, it is suitable not only for coloring the pixel portion of the color filter but also for coloring paint, plastic, printing ink, rubber, leather, textile printing, electrophotographic toner, inkjet ink, thermal transfer ink, and the like.

  Further, the organic pigment composition of the present invention includes a sulfonic acid derivative, an N- (dialkylamino) methyl derivative, an N- (dialkylaminoalkyl) sulfonic acid amide derivative, and a phthalimide alkyl derivative of the organic pigment (A). Such as organic pigment derivatives, Dispavik 130, Dispersic 161, Dispersic 162, Dispersic 163, Dispersic 170, Dispersic 171, Dispersic 174, Dispersic 180, Dispersic 182 and Dispersic 183 , Dispersic 184, Dispersic 185, Dispersic 2000, Dispersic 2001, Dispersic 2020, Dispersic 2050, Dispersic 2070, Dispersi 2096, Dispersic 2150, Dispersic LPN21116, Dispersic LPN6919 Efka 46, Efka 47, Efka 452, Efka LP4008, Efka 4009, Efka LP4010, Efka LP4050, LP4055, Efka 400, Efka 401, Evka 402, Efka 402 403, EFKA 450, EFKA 451, EFKA 453, EFKA 4540, EFKA 4550, EFKA LP4560, EFKA120, EFKA150, EFKA1501, EFKA1502, EFKA1503, Lubrizol SolSparse 3000, Solsparse 9000, Solsparse 12000, Solsparse 13240 Solsparse 13650, Solsparse 13940, Solsparse 17000, 18000, Sol Perth 20000, Sol Sparse 21000, Sol Sparse 20000, Sol Sparse 24000, Sol Sparse 26000, Sol Sparse 27000, Sol Sparse 28000, Sol Sparse 32000, Sol Sparse 36000, Sol Sparse 37000, Sol Sparse 38000, Sol Sparse 41000, Sol Sparse 42000, Sol Sparse 43000, Sol Sparse 46000, Sol Sparse 54000 Ajinomoto Co., Inc. Ajisper PB711, Ajisper PB821, Ajisper PB822, Ajisper PB814, Ajisper PN411, Ajisper PA111, and other dispersants, natural resins such as acrylic resin, urethane resin, alkyd resin, wood rosin, gum rosin, tall oil rosin Rosin Room temperature, modified rosin such as polymerized rosin, disproportionated rosin, hydrogenated rosin, oxidized rosin, maleated rosin, rosin amine, lime rosin, rosin alkylene oxide adduct, rosin alkyd adduct, rosin modified phenol etc. And can contain a liquid and water-insoluble synthetic resin. Addition of these dispersants and resins also contributes to reduction of flocculation, improvement of pigment dispersion stability, and improvement of viscosity characteristics of the dispersion.

  The organic pigment composition of the present invention can be used for any known and commonly used application. However, when it is contained in the pixel portion of a color filter, it has an average primary particle diameter of 0.01 to 0.10 μm. If it exists, pigment aggregation is also comparatively weak and the dispersibility to the synthetic resin etc. which should be colored becomes more favorable.

  By incorporating the organic pigment composition of the present invention described above or the organic pigment composition obtained by the production method of the present invention into the pixel portion of each color of R, G, B of the color filter, a color filter can be obtained. I can do it. Specifically, for example, C.I. I. From the organic pigment composition of the present invention containing a diketopyrrolopyrrole pigment such as C.I. I. From the organic pigment composition of the present invention containing a halogenated metal phthalocyanine pigment such as C.I. I. B pixels can be obtained from the organic pigment composition of the present invention containing a metal phthalocyanine pigment such as CI Pigment Blue 15: 6.

  As described above, the organic pigment composition of the present invention can be used for forming a pattern of R, G, B color pixel portions of a color filter by a known method. Typically, a color filter pixel part photosensitive composition containing the pigment composition for a color filter of the present invention and a photosensitive resin as essential components can be obtained.

  As a method for producing a color filter, for example, the organic pigment composition of the present invention is dispersed in a dispersion medium made of a photosensitive resin, and then applied onto a transparent substrate such as glass by a spin coating method, a roll coating method, an ink jet method, or the like. There is a method called photolithography in which the coating film is subjected to pattern exposure with ultraviolet rays through a photomask, and then an unexposed portion is washed with a solvent or the like to obtain each color pattern.

  In addition, a color filter may be manufactured by forming a pattern of each color pixel portion by an electrodeposition method, a transfer method, a micellar electrolysis method, or a PVED (Photovoltaic Electrodeposition) method. The organic pigment composition of the present invention is extremely useful in, for example, a method for producing a color filter in which baking is included in the process because the hue change is small even when subjected to a thermal history.

  To prepare a photosensitive composition for a color filter pixel portion, for example, the organic pigment composition of the present invention, a photosensitive resin, a photopolymerization initiator, and an organic solvent that dissolves the resin are mixed as essential components. To do. As a production method thereof, a method of preparing a dispersion by using the organic pigment composition of the present invention, an organic solvent, and a dispersant as required, and then adding a photosensitive resin or the like to the dispersion is generally used. is there.

  Dispersants used as necessary include, for example, Big Chemie's Disperbyk (registered trademark) 130, Dispersic 161, Dispersic 162, Dispersic 163, Dispersic 170, Efka 46, Efka 47, and the like. It is done. In addition, a revenig rigging agent, a coupling agent, a cationic surfactant, and the like can be used together.

  Examples of the organic solvent include aromatic solvents such as toluene, xylene, and methoxybenzene, acetate solvents such as ethyl acetate and butyl acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and ethoxyethyl propionate. Propionate solvents such as alcohol solvents such as methanol and ethanol, ether solvents such as butyl cellosolve, propylene glycol monomethyl ether, diethylene glycol ethyl ether and diethylene glycol dimethyl ether, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, and fats such as hexane Group hydrocarbon solvents, N, N-dimethylformamide, γ-butyrolactam, N-methyl-2-pyrrolidone, ani Emissions, nitrogen compound-based solvent such as pyridine, a lactone-based solvents such as γ- butyrolactone, carbamic acid esters such as a mixture of 48:52 of methyl carbamate and ethyl carbamate, there is water. As the organic solvent, polar solvents such as propionate-based, alcohol-based, ether-based, ketone-based, nitrogen compound-based, lactone-based, water and the like that are water-soluble are particularly suitable.

  Per 100 parts by mass of the organic pigment composition of the present invention, 300 to 1000 parts by mass of an organic solvent and 0 to 200 parts by mass of a dispersant and / or 0 to 20 parts by mass of a pigment derivative as required The dispersion can be obtained by stirring and dispersing as described above. Next, 0.5 to 20 parts by mass of the photosensitive resin per 1 part by mass of the organic pigment composition of the present invention, 0.05 to 3 parts by mass of a photopolymerization initiator per 1 part by mass of the photosensitive resin are added to the dispersion. Further, if necessary, an organic solvent can be further added and stirred and dispersed so as to be uniform, whereby a photosensitive composition for a color filter pixel portion can be obtained.

  Examples of photosensitive resins that can be used in this case include urethane resins, acrylic resins, polyamic acid resins, polyimide resins, styrene maleic acid resins, styrene maleic anhydride resins, and the like, Bifunctional monomers such as 1,6-hexanediol diacrylate, ethylene glycol diacrylate, neopentyl glycol diacrylate, triethylene glycol diacrylate, bis (acryloxyethoxy) bisphenol A, 3-methylpentanediol diacrylate, Trimethylol propaton triacrylate, pentaerythritol triacrylate, tris (2-hydroxyethyl) isocyanate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate It includes photopolymerizable monomers such as polyfunctional monomers such as.

  Examples of the photopolymerization initiator include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4′-azidobenzal) -2-propane, 1,3-bis (4 ′). -Azidobenzal) -2-propane-2'-sulfonic acid, 4,4'-diazidostilbene-2,2'-disulfonic acid and the like.

  The thus-prepared photosensitive composition for a color filter pixel portion can be converted into a color filter by performing pattern exposure with ultraviolet rays through a photomask and then washing the unexposed portion with an organic solvent or alkaline water. it can.

  Hereinafter, the present invention will be specifically described using adjustment examples, synthesis examples, examples, and comparative examples. In these examples, “part” means “part by weight” and “%” means mass percent.

[Synthesis Example 1] (Synthesis of polyamideimide resin (B-1))
In a four-necked flask equipped with a stirrer, thermometer, cooling pipe and nitrogen introduction pipe, 1464 parts of propylene glycol monomethyl ether acetate (manufactured by Daicel Chemical Industries, Ltd.), 888 parts of isophorone diisocyanate (manufactured by Wako Pure Chemical Industries, Ltd.) and 960 parts of trimellitic anhydride (manufactured by Tokyo Chemical Industry Co., Ltd.) was added, and the temperature was raised to 140 ° C. under a nitrogen stream. The reaction proceeds with foaming, and the inside of the system becomes a light brown clear liquid. As a result of measuring characteristic absorption in the infrared spectrum, 2270 cm-1 which is the characteristic absorption of the isocyanate group completely disappears, 725 cm-1, Absorption of imide groups was confirmed at 1780 cm −1 and 1720 cm −1. The mixture was reacted at this temperature for 4 hours to obtain a resin solution consisting of a polymer having a weight average molecular weight of 1,600 and an acid value (converted to solid content) of 85 KOH mg / g. This resin solution was dried under reduced pressure (60 ° C., 24 hours) to obtain a polyamideimide resin (B-1).

The weight average molecular weight was determined using GPC under the following conditions.
Measuring device: HLC-8120GPC, UV8020 manufactured by Tosoh Corporation
Column: TFKguardcolumnhxl-L, TFKgel (G1000HXL, G2000HXL, G3000HXL, G4000HXL) manufactured by Tosoh Corporation
Detector: RI (differential refractometer) and UV (254 nm)
Measurement conditions: Column temperature 40 ° C
Solvent THF (Wako Pure Chemical Industries, Ltd.)
Flux 1.0ml / min
Standard: Calibration curve prepared with polystyrene standard sample Sample: 0.1% by mass THF solution in terms of resin solids filtered through microfilter (injection amount: 200 μl)

[Synthesis Example 2] (Synthesis of polyamideimide resin (B-2))
To a four-necked flask equipped with a stirrer, thermometer, cooling tube and nitrogen introduction tube, 1464 parts of propylene glycol monomethyl ether acetate (manufactured by Daicel Chemical Industries, Ltd.), IPDI3N-1 (isophorone diisocyanate manufactured by Wako Pure Chemical Industries, Ltd.) Synthesized isocyanurate type triisocyanate: NCO% = 18.2) 2760 parts and trimellitic anhydride (Tokyo Chemical Industry Co., Ltd.) 1728 parts were added, and the temperature was raised to 150 ° C. under a nitrogen stream. The reaction proceeds with foaming, and the inside of the system becomes a light brown clear liquid. As a result of measuring characteristic absorption in the infrared spectrum, 2270 cm-1 which is the characteristic absorption of the isocyanate group completely disappears, 725 cm-1, Absorption of imide groups was confirmed at 1780 cm −1 and 1720 cm −1. The reaction was carried out at this temperature for 8 hours to obtain a resin solution consisting of a polymer having a weight average molecular weight of 4,100 and an acid value (in terms of solid content) of 95 KOH mg / g. This resin solution was dried under reduced pressure (60 ° C., 24 hours) to obtain a polyamideimide resin (B-2).

[Synthesis Example 3] (Synthesis of polyamideimide resin (B-3))
To a four-necked flask equipped with a stirrer, thermometer, cooling tube and nitrogen introduction tube, 1086 parts of propylene glycol monomethyl ether acetate (Daicel Chemical Industries, Ltd.), IPDI3N-2 (isophorone diisocyanate manufactured by Wako Pure Chemical Industries, Ltd.) Synthesized isocyanurate-type triisocyanate: NCO% = 17.2) 587.3 parts and cyclohexane-1,3,4-tricarboxylic acid-3,4-anhydride 499.1 parts were added, and 140. The temperature was raised to ° C. The reaction proceeds with foaming, and the inside of the system becomes a pale yellow clear liquid. As a result of measuring characteristic absorption in the infrared spectrum, 2270 cm-1 which is the characteristic absorption of the isocyanate group completely disappears, 725 cm-1, Absorption of imide groups was confirmed at 1780 cm −1 and 1720 cm −1. The reaction was carried out at this temperature for 8 hours. Subsequently, 96.3 parts of n-butanol (manufactured by Wako Pure Chemical Industries, Ltd.) was added and reacted at 120 ° C. for 2 hours. As a result of measuring the characteristic absorption in the infrared spectrum, the mass absorption at 1860 cm −1, which is the characteristic absorption of the acid anhydride group, disappeared completely. A resin solution made of a polymer having a weight average molecular weight of 4,800 and an acid value (in terms of solid content) of 148 KOH mg / g was obtained. This resin solution was dried under reduced pressure (60 ° C., 24 hours) to obtain a polyamideimide resin (B-3).

(Synthesis Example 4) [Synthesis of Comparative Resin (C-1)]
After charging 1540 parts of propylene glycol monomethyl ether acetate (Daicel Chemical Industries, Ltd.) into a four-necked flask equipped with a stirrer, thermometer, cooling tube and nitrogen introduction tube, the temperature was raised to 110 ° C. under a nitrogen stream, and then benzyl 856 parts of methacrylate (manufactured by Wako Pure Chemical Industries, Ltd.), 142 parts of methacrylic acid (manufactured by Wako Pure Chemical Industries, Ltd.) and 15 parts of t-butylperoxy-2-ethylhexanoate (manufactured by NOF Corporation) The mixture was added dropwise over 4 hours. After completion of dropping, the reaction was carried out at 110 ° C. for 7 hours to obtain a solution comprising a copolymer having a weight average molecular weight of 18,000. This resin solution was dried under reduced pressure (60 ° C., 24 hours) to obtain a comparative resin (C-1).

(Synthesis Example 5) [Synthesis of Comparative Resin (C-2)]
Into a four-necked flask equipped with a stirrer, thermometer, cooling tube and nitrogen introduction tube, 1540 parts of propylene glycol monomethyl ether acetate (Daicel Chemical Industries, Ltd.) was charged, and the temperature was raised to 110 ° C. under a nitrogen stream. 597 parts of methacrylate (made by Wako Pure Chemical Industries, Ltd.), 261 parts of n-butyl methacrylate (made by Wako Pure Chemical Industries, Ltd.), 142 parts of glycidyl methacrylate (made by Wako Pure Chemical Industries, Ltd.) and t-butylperoxy-2 -The liquid mixture which consists of 18 parts of ethyl hexanoate (made by NOF Corporation) was dripped over 4 hours. After completion of the dropwise addition, the mixture was reacted at 110 ° C. for 7 hours to obtain a solution made of a copolymer having a weight average molecular weight of 15,000. This resin solution was dried under reduced pressure (60 ° C., 24 hours) to obtain a comparative resin (C-2).

[Example 1]
85 parts of FASTOGEN Blue AE-8 (CI Pigment Blue 15: 6 manufactured by DIC Corporation), 5 parts of copper phthalocyanine phthalimidomethyl derivative (manufactured by DIC Corporation) with an average substituent number of 1.4, polyamideimide resin (B- 1) 10 parts, 1000 parts of crushed sodium chloride (manufactured by Nippon Salt Manufacturing Co., Ltd.) and 160 parts of diethylene glycol (manufactured by Mitsubishi Chemical Corporation) were charged into a double-arm kneader and kneaded at 80 to 90 ° C. for 10 hours.
The obtained contents were washed with a large excess of water, filtered, and washed with water until the specific conductivity of the filtrate was equal to or less than the specific conductivity of raw water + 20 μS / cm, whereby a wet cake of ε-type copper phthalocyanine pigment composition was obtained. Obtained. The obtained wet cake was transferred to a beaker, 3000 parts of a 2% hydrochloric acid (Daikin Industries Co., Ltd.) aqueous solution was added, and the mixture was stirred and dispersed to form a slurry. After stirring at 70 ° C. for 1 hour, filtration and washing were performed to obtain a wet cake. . The obtained wet cake was transferred to a beaker, 3000 parts of water at room temperature was added, and the mixture was stirred and dispersed to obtain a slurry. Subsequently, an aqueous solution of sodium hydroxide (manufactured by Wako Pure Chemical Industries, Ltd.) of 5 parts of copper phthalocyanine sulfonic acid derivative (manufactured by DIC Corporation) having an average number of substituents of 0.8 is added to the pigment slurry and stirred for 1 hour. Hydrochloric acid (Daikin Kogyo Co., Ltd.) was added to return the pH of the slurry to 7, and a copper phthalocyanine sulfonic acid derivative was precipitated on the surface of the pigment. After being kept for 1 hour, it was filtered, washed with warm water, dried and pulverized to obtain a blue pigment composition having an average primary particle diameter of 100 nm or less.

20 parts of the blue pigment composition thus obtained is placed in a polyvin, 110 parts of propylene glycol monomethyl ether acetate (Daicel Chemical Industries, Ltd.), 14 parts of DISPERBYK LPN21116 (manufactured by Big Chemie Co., Ltd.), 0.3-0 4 mmφ Sepul beads (manufactured by Saint-Gobain Co., Ltd.) were added and dispersed for 4 hours with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) to obtain a blue organic pigment dispersion.

Subsequently, 75.00 parts of a blue organic pigment dispersion, 5.50 parts of a polyester acrylate resin (Aronix (trade name) M7100, manufactured by Toa Gosei Chemical Co., Ltd.), dipentaerythrate hexaacrylate (KAYARAD (trade name) DPHA) , Manufactured by Nippon Kayaku Co., Ltd.) 5.00 parts, benzophenone (KAYACURE (trade name) BP-100, manufactured by Nippon Kayaku Co., Ltd.) 1.00 parts, Yuker ester EFP (manufactured by Dow Chemical Co., Ltd.) 13.5 parts Was stirred with a dispersion stirrer and filtered through a filter having a pore size of 1.0 μm to obtain a color resist. This color resist spin coater was applied onto a 50 mm × 50 mm, 1 mm glass substrate and pre-dried at 90 ° C. for 20 minutes to form a coating film. Next, after performing pattern exposure with ultraviolet rays through a photomask, the unexposed portion is washed in an aqueous solution of 0.5% sodium carbonate (manufactured by Wako Pure Chemical Industries, Ltd.) and baked at 230 ° C. for 60 minutes. The color filter was used.

[Evaluation of viscosity of organic pigment dispersion]
Using the organic pigment dispersion, the viscosity of the dispersion at 20 ° C. was measured with TVE-25L manufactured by Toki Sangyo Co., Ltd. The smaller the dispersion viscosity, the better.

[Evaluation of luminance Y]
Using the color filter after baking at 230 ° C., the luminance Y in the C light source was measured with MCPD-3000 manufactured by Otsuka Electronics Co., Ltd. The larger the value of the luminance Y, the better.

Using the blue organic pigment dispersion and color filter obtained in Example 1, the pigment dispersion viscosity and luminance Y after firing at chromaticity y = 0.110 were evaluated. The dispersion viscosity was 7.6 mPa · s. The luminance Y was 13.3.

[Example 2]
A blue pigment composition was obtained in the same manner as in Example 1 except that the polyamideimide resin (B-2) was used instead of the polyamideimide resin (B-1) in Example 1, and a blue pigment composition was used. An organic pigment dispersion and a color filter were obtained. When the pigment dispersion viscosity and the color filter were used to evaluate the brightness Y after firing at a pigment dispersion viscosity and chromaticity y = 0.110, the dispersion viscosity was 8.5 mPa · s, and the brightness Y was 13.2. 3.

[Example 3]
A blue pigment composition was obtained in the same manner as in Example 1 except that the polyamideimide resin (B-3) was used in place of the polyamideimide resin (B-1) in Example 1, and a blue pigment composition was used. An organic pigment dispersion and a color filter were obtained. When the pigment dispersion viscosity and the color filter were used to evaluate the brightness Y after firing at a pigment dispersion viscosity and chromaticity y = 0.110, the dispersion viscosity was 8.3 mPa · s and the brightness Y was 13. 3.

[Example 4]
C. I. Pigment Red 254 (manufactured by DIC Corporation) 44 parts, pigment derivative phthalimidomethylated dichloroquinacridone (manufactured by DIC Corporation) 1 part of the following general formula (IV), dimethyl sulfoxide 1500 parts (manufactured by Wako Pure Chemical Industries, Ltd.) The mixture was dissolved in a mixed solvent of 55 parts of a 28 wt% methanol solution of sodium methoxide (manufactured by Sigma Aldrich), stirred at 50 ° C for 3 hours, and then allowed to cool to 35 ° C to obtain a red pigment solution.

(However, the substitution number n of the phthalimidomethyl group is 1 to 3.)

Next, 34 parts of hydrochloric acid (concentration: 35.0% to 37.0%, manufactured by Wako Pure Chemical Industries, Ltd.) is added to 2200 parts of water and 2700 parts of ice. While stirring, the red pigment solution was added dropwise and stirred for 1 hour after completion of the addition. The obtained pigment suspension containing the composite particles was filtered with Nutsche, filtered and washed with water until the pH of the filtrate reached 7 or higher, dried and pulverized at 90 ° C. for 17 hours to obtain a red pigment powder. .

Subsequently, 35 parts of the red pigment powder, 1 part of phthalimidomethylated dichloroquinacridone (manufactured by DIC Corporation), 4 parts of polyamideimide resin (B-1), 400 parts of sodium chloride (manufactured by Nippon Salt Manufacturing Co., Ltd.), and diethylene glycol 70 parts (manufactured by Mitsubishi Chemical Corporation) were charged into a stainless steel 1 L kneader (manufactured by Yoshida Seisakusho) and kneaded at 80 ° C. for 5 hours. Next, this mixture is poured into 2 liters of warm water, stirred for 30 minutes to form a slurry, and filtered and washed repeatedly until the specific conductivity is less than the specific conductivity of raw water + 20 μS / cm to remove sodium chloride and solvent. And then dried and pulverized at 90 ° C. for 17 hours to obtain 35 parts of a red pigment composition having an average primary particle size of 100 nm or less.

20 parts of the red pigment composition thus obtained are put in a polybin, 88 parts of propylene glycol monomethyl ether acetate (manufactured by Daicel Chemical Industries, Ltd.), 24 parts of DISPERBYK LPN21116 (manufactured by BYK Chemie Corporation), 0.3- 0.4 mmφ Sepul beads (manufactured by Saint-Gobain Co., Ltd.) were added and dispersed for 2 hours with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) to obtain a red organic pigment dispersion.

75.00 parts of this red organic pigment dispersion, 5.50 parts of polyester acrylate resin (Aronix (trade name) M7100, manufactured by Toa Synthetic Chemical Industry Co., Ltd.), dipentaerythrate hexaacrylate (KAYARAD (trade name) DPHA, Japan) 5.00 parts of Kayaku Co., Ltd., 1.00 parts of benzophenone (KAYACURE (trade name) BP-100, Nippon Kayaku Co., Ltd.) and 13.5 parts of Euker Ester EFP (Dow Chemical Co., Ltd.) are dispersed. The color resist was obtained by stirring with a stirrer and filtering with a filter having a pore size of 1.0 μm. This color resist spin coater was applied onto a 50 mm × 50 mm, 1 mm glass substrate and pre-dried at 90 ° C. for 20 minutes to form a coating film. Next, after performing pattern exposure with ultraviolet rays through a photomask, the unexposed portion is washed in an aqueous solution of 0.5% sodium carbonate (manufactured by Wako Pure Chemical Industries, Ltd.) and baked at 230 ° C. for 60 minutes. The color filter was used.

Using the red organic pigment dispersion obtained in Example 4 and the color filter, the luminance Y after firing at a pigment dispersion viscosity and chromaticity x = 0.640 and chromaticity y = 0.320 was evaluated. The body viscosity was 10.5 mPa · s, and the luminance Y was 19.2.

(Comparative Example 1)
A blue pigment composition was obtained in the same manner as in Example 1 except that the comparative resin (C-1) was used in place of the polyamideimide resin (B-1) in Example 1, and a blue organic color was used. A pigment dispersion and a color filter were obtained. When the pigment dispersion viscosity and the color filter were used to evaluate the brightness Y after firing at a pigment dispersion viscosity and chromaticity y = 0.110, the dispersion viscosity was 7.9 mPa · s and the brightness Y was 13. 2.

(Comparative Example 2)
A blue pigment composition was obtained in the same manner as in Example 1 except that the comparative resin (C-2) was used instead of the polyamideimide resin (B-1) in Example 1, and a blue organic color was obtained using the blue pigment composition. A pigment dispersion and a color filter were obtained. When the pigment dispersion viscosity and the color filter were used to evaluate the luminance Y after firing at a pigment dispersion viscosity and chromaticity y = 0.110, the dispersion viscosity was 11.1 mPa · s and the luminance Y was 13. 3.

(Comparative Example 3)
In the same manner as in Example 1 except that 85 parts of FASTOGEN Blue AE-8 of Example 1 and 10 parts of polyamideimide resin (B-1) were changed to only 95 parts of FASTOGEN Blue AE-8 without addition of resin. A blue pigment composition was obtained and used as a blue organic pigment dispersion and a color filter. When the pigment dispersion viscosity and the color filter were used to evaluate the luminance Y after firing at a pigment dispersion viscosity and chromaticity y = 0.110, the dispersion viscosity was 10.4 mPa · s and the luminance Y was 13. 1

(Comparative Example 4)
A red pigment composition was obtained in the same manner as in Example 4 except that the comparative resin (C-2) was used in place of the polyamideimide resin (B-1) in Example 4, and a red organic compound was used. A pigment dispersion and a color filter were obtained. When the pigment dispersion viscosity and the chromaticity x = 0.640 and the luminance Y after firing at the chromaticity y = 0.320 were evaluated using the obtained pigment dispersion and the color filter, the dispersion viscosity was 14.6 mPa.s. -S and the brightness | luminance Y were 19.1.

(Comparative Example 5)
The red pigment composition was the same as in Example 4 except that 35 parts of the red pigment powder of Example 4 and 4 parts of the polyamideimide resin (B-1) were changed to only 39 parts of the red pigment powder without addition of resin. And used as a color filter. When the pigment dispersion viscosity and chromaticity x = 0.640, and the luminance Y after firing at chromaticity y = 0.320 were evaluated using the obtained pigment dispersion and color filter, the dispersion viscosity was 25.8 mPa.s. -S and the brightness | luminance Y were 18.8.

The evaluation results of Examples 1 to 4 and Comparative Examples 1 to 5 are shown in Table 1.

(In the table, B-15: 6 represents CI Pigment Blue 15: 6, and R-254 represents CI Pigment Red 254.)

As can be seen from the comparison between Examples 1 to 3 in Table 1 and Comparative Example 3 and the comparison between Example 4 and Comparative Example 5, it is more organic when the polyamideimide resin (B) is contained in the organic pigment. It is clear that the pigment dispersion has low viscosity and high brightness.
Moreover, compared with Example 1-3 of the said Table 1, and Comparative Examples 1 and 2, and the comparison of Example 4 and Comparative Example 5, the direction of the polyamideimide resin (B) used by this invention is used conventionally. It is clear that a high brightness after firing is obtained despite the low viscosity of the organic pigment dispersion compared to the copolymers that have been produced.

  According to the present invention, due to the unique dispersibility and heat resistance due to the interaction between the organic pigment (A) and the polyamideimide resin (B), the viscosity of the organic pigment dispersion is low and the hue changes even when subjected to a thermal history. A liquid crystal capable of providing a colored material with a small brightness, especially when used for the preparation of a pixel portion of a color filter, and capable of providing a liquid crystal display with high brightness and excellent brightness even when subjected to a heat history for a long time. A display device can be provided.

Claims (7)

An organic pigment composition for a color filter, containing 0.1 to 15 parts of polyamideimide resin (B) per 100 parts of organic pigment (A) in terms of mass. The organic pigment composition for a color filter according to claim 1, wherein the polyamideimide resin (B) is treated on the surface of pigment particles of the organic pigment (A). The polyamideimide resin (B) reacts an aliphatic isocyanate compound and / or an alicyclic isocyanate compound having two or more isocyanate groups in the molecule with a tricarboxylic acid anhydride and / or a tetracarboxylic acid anhydride. The organic pigment composition for a color filter according to claim 1, which is a polyamideimide resin obtained. The polyamideimide resin (B) is obtained by reacting an isocyanurate type polyisocyanate synthesized from an isocyanate having an aliphatic structure with a tricarboxylic acid anhydride to produce a polyamideimide resin, and then reacting with an alcohol compound. The organic pigment composition for a color filter according to claim 1, which is an alcohol-modified polyamideimide resin. The method for producing an organic pigment composition for a color filter according to any one of claims 1 to 4, wherein solvent salt milling is performed on the organic pigment (A) in the presence of the polyamideimide resin (B). A color filter comprising the organic pigment composition for a color filter according to claim 1 in a pixel portion. A color filter comprising an organic pigment composition for a color filter obtained by the production method according to claim 5 in a pixel portion.