TW200936703A - Color dispersion coagent, pigment dispersant and pigment dispersion photoresist composition for color filter - Google Patents

Abstract

The invention provides a pigment dispersion coagent, which may be produced at a high efficiency by using concentrated sulfuric acid or oleum, and may exhibit an excellent pigment dispersability by employed in conjunction with a pigment dispersant. The feature of the pigment dispersion coagent is that it is a compound represented by the following general formula (1) [where M represents H, Na, K, NH.sub.4 or NR.sup.1R.sup.2R.sup.3R.sup.4 (R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are the same or different, and represent substitutable saturated or unsaturated aliphatic hydrocarbon groups of 1 to 10 carbon atoms, or substitutable aromatic hydrocarbon groups of 6 to 10 carbon atoms); m represents an integer of 1 or more].

Description

200936703 VI. Description of the invention: [Technical field to which the invention pertains] The present invention relates to the recording of soil, sputum, and seed scented granules and their use; more specifically, the present invention provides a It is suitable for printing inks, coatings, and pigment-dispersing photoresist compositions for liquid crystal filters, which is useful for maintaining the fluidity and dispersion stability of finely dispersed organic pigments (hereinafter, also referred to as "resistance for liquid crystal color filters". a pigment dispersion in a wide range of fields such as "agent" or "resist composition for liquid crystal color filter"), ink for inkjet, and the like; in particular, it relates to a photoresist used in a liquid crystal color filter, which can improve brightness or contrast. To a more standard pigment dispersing aid and its use. [Prior Art] Organic pigments have been known as coloring agents as early as possible. Various inks or coatings have recently been used in liquid crystal filters or inkjet inks, which require high transparency or high contrast. field. The dispersion technology of organic pigments such as Xiao has made significant progress in recent years, and in order to achieve rationalization of manufacturing, the industry is also studying the method of increasing the pigment concentration as much as possible: the method of dispersion. However, basically, there is a problem that if the concentration of the pigment is increased, the fluidity and dispersion stability are lowered. Moreover, in the field of liquid crystal color filters or ink jet recording, since high-fastness is required, it is necessary to use a strong high-grade pigment, and in order to obtain a hue of a fresher disc, it is necessary to disperse a strong high-grade organic pigment into a finer particle diameter. However, compared with other pigments, the high-grade organic pigments are not dispersible, and the finer the finer, the more likely they are to cause agglomeration. Four times

200936703 4 to solve the above problems, the treatment of white 涑 a body (surface treatment 汝 、, 刖 藉 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 = = 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料 颜料For example, it is disclosed that the use of a base having a basic group when dispersing an acidic pigment is used: the affinity of the acid-test is used to adsorb the pigment dispersant: the pigment 2 to obtain good dispersion stability. Method (for example, refer to the patent, ). However, if the affinity of the above-mentioned acid-base is used to improve the sharpness of the pigment knives, it is required to achieve a higher transmittance or contrast ratio required in the field of liquid crystal color filter or ink jet printing. It is not sufficient. > In terms of obtaining a color tone or brightness suitable for a liquid crystal color filter, it is known that, in particular, in the above-mentioned high-grade pigment, a diketopyrrolopyrrole system is used. As a red pigment, the pigment can be greatly improved compared with the 4,4,-diamino _u, _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ The ketone base is a light transmission curve which shows a shape with a large increase in slope near 550 to 600 nm, and in particular, the effect of improving the brightness γ value by using the micronized treatment product becomes obvious. However, it is preferred. However, the diketopyrrolopyrrole pigment exhibits a strong cohesive force due to its highly symmetrical molecular structure, so it cannot be micronized by ordinary dispersion techniques. Pigment dispersing aids which are used with pigment dispersants and which are used to improve pigment dispersibility are also being studied. For example, pigment dispersing aids using pigment dispersing swords and pigment dispersing aids containing a diketone n-pirol and D-rhodium compound having a contiguous group are disclosed. 'Method for improving the dispersibility of a diketopyrrolopyrrole pigment (Example 5 200936703, see, for example, Patent Document 3). By using the above-mentioned pigment dispersing aid, the pigment dispersibility can be improved, and therefore the above-mentioned constitution is considered to realize liquid crystal color filter. One of the means of high transmittance or contrast required in the field of the device. Here, 'in order to obtain a sulfo-keto-pyrrolopyrrole compound as specifically described in Patent Document 3 The concentrated sulfuric acid or fuming sulfuric acid must be allowed to react with the diketopyrrolopyrrole pigment for sulfonation. However, due to the strong oxidation of concentrated sulfuric acid or fuming sulfuric acid, it sometimes causes the diketone group in this step. The pyrrolopyrrole pigment is decomposed. In this case, not only the desired yield of the diketopyrrolopyrrole compound having a sulfo group is lowered, but also a large amount of impurities due to decomposition are mixed, so the crystallinity is lowered and the separation operation is changed. Difficulties, so that the cost is greatly increased. If the use of milder chemicals for confirmation can also reduce the above disadvantages, but at this time the renewal reaction takes a long time, and the use of expensive chemicals instead of cheap concentrated sulfuric acid or hair In the case of the sulphuric acid, the sulphuric acid is not practical. Patent Document 1 Japanese Patent Laid-Open No. Hei. No. Hei. 〇〇·16〇〇84 容明发, Therefore, the first subject of the present invention is to obtain high-efficiency production using concentrated sulfuric acid sulfuric acid, and by pigmentation Agent excellent in pigment dispersibility and dispersion stability of a pigment or dispersing aid City play. Further, a second object of the invention is to obtain an excellent dispersibility or dispersibility of the pigment by using the above-mentioned pigment dispersing aid, and the third object is to obtain a high luminance γ value by using the above pigment dispersion or The contrast value of the color filter is divided into pigments by ^oa ^ a bamboo knife and the first resist composition. Other problems of the present invention can be clarified by the following description of the present specification. The inventors of the present invention have made diligent research and found that among the bismuth base materials, especially the phthalocyanine dispersing aid obtained by cu picking orange 71 into (four), even if the producer uses concentrated sulfuric acid or fuming sulfuric acid, the producer It can also be obtained in good yield and with good crystallinity. The present invention has been completed based on this knowledge, and the above problems can be solved. That is, (1) The present invention relates to a pigment dispersing aid characterized by the compound represented by the following formula (1):

Wherein Μ represents η, Na, κ, ΝΗ4 or NRWR4^1, R2, R and R are the same or different and represent a saturated or unsaturated aliphatic hydrocarbon group having a carbon number of 10 10 which may also be substituted by other substituents, or An aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted by another substituent; m represents an integer of i or more, and (2) the present invention relates to a pigment dispersion characterized in that: 200936703 contains an organic pigment, pigment dispersion Sword, such as the pigment dispersing aid of the above item (1) and an organic solvent. Further, (3) The present invention relates to the pigment dispersion according to the above (2), wherein the pigment dispersant has an organic matrix. Further, (4) The present invention relates to the pigment dispersion according to the above item (2) or (3), wherein the pigment dispersant is an acrylic block copolymer having a basic group. The present invention relates to the pigment knives of any one of the above items (2) to (4), wherein the organic pigment is a diketopyrrolopyrrole pigment. Further, (6) The present invention relates to the pigment dispersion according to the above (5) wherein the diketopyrrolopyrrole pigment is C.I_Pigment Red 254. The present invention relates to the pigment dispersion according to any one of the above items (2) to (6) wherein the organic pigment is micronized. Further, (8) The present invention relates to the pigment dispersion according to the above (7), wherein the microparticulation treatment is a salt milling treatment (saU milling pr〇cess). Further, (9) The present invention relates to the pigment dispersion according to the above (8), wherein the salt milling treatment is carried out by the following steps: 八 ◎ containing an organic pigment, a water-soluble inorganic salt, and substantially not dissolving the above The mixture of the water-soluble dispersion medium of the inorganic salt is kneaded by a kneading device in which three feeding airfoil surfaces are subjected to a revolving motion, and the inorganic salt and the water-soluble dispersion medium are removed. Further, (10) The present invention relates to a pigment-dispersed photoresist composition for a color filter, which is characterized by comprising the pigment dispersion according to any one of the above items (7) to (9). 8 200936703 First, the pigment dispersing aid of the present invention will be specifically described. The pigment dispersion aid of the present invention is a compound represented by the above formula (1). Where Μ represents H, Na, κ, NH4 or nr1r2r3r4.

Regarding "nr1r2r3r4" (M) of the above formula (1), R1, R2, & 3 and R4 are the same or different and represent a saturated or non-fresh (tetra)hydrocarbyl group having a carbon number of i to 10 which may be substituted by other substituents. Or the aromatic tobacco group with a carbon number of 6 1G replaced by other substituents. Here, the saturated or unsaturated aliphatic hydrocarbon group may, for example, be a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a second butyl group, a tert-butyl group, a pentyl group or a hexyl group. , octyl, fluorenyl and the like; alkenyl groups such as vinyl, allyl, i. butenyl; alkynyl, propyl and the like. The aromatic hydrocarbon group may, for example, be a phenyl group or a naphthyl group. Further, examples of the other substituents include a hydroxyl group, a terminal group, a carboxyl group, an amine group, and a lower alkyl group (having a carbon number of 1 to 5). Further, in the above R1, R2, R3 and R4, i may be substituted by another substituent, and two or more of them may be substituted by other substituents. Further, "m" of the above formula (1) is an integer of 丨 or more. The above-mentioned pigment dispersing aid can be produced by subjecting c.L. Pigment Orange 71 represented by the following formula (2) to a previously known sulfonation treatment. For example, the pigment powder of CI Pigment Orange 71 is dissolved in a mixture of concentrated sulfuric acid, fuming sulfuric acid, gas sulfonic acid or the like, and heated to room temperature to 8 〇 to 9 (rc, followed by dilution with a large amount of water. At this time, the sulfonated Pigment Orange 71 is crystallized and suspended. The obtained suspension is filtered, washed with water, and then the filter cake is dried and pulverized, whereby the desired pigment dispersing aid can be obtained. Of course, it is also possible to neutralize the sulfonate obtained by the reaction by using an inorganic basic compound such as sodium hydroxide or an aqueous ammonia solution or an organic basic compound such as 200936703 organic amine to thereby form a sodium salt or a potassium salt. Money salt or organic salt, etc. Further, there is no commercial product of the above pigment dispersing aid.

C.I. Pigment Orange 71 can be used by a known person. When the amount of the drug to be used in the sulfonation is, for example, concentrated sulfuric acid is used, the amount of the pigment and the concentrated sulfuric acid can be stirred to a slurry. As shown in the above formula (2), C丄Pigment Orange 71 has a diketopyrrolo. The Bilo skeleton has two 3-cyanophenyl structures. This is also indicated in its examples, for example, by bonding to a diketopyllop. When the Bilo skeleton is a stupid base (the following formula (3)) or a tolyl group (the following formula (4)), decomposition occurs during the process of the performance, and thus the pigment dispersion cannot be favorably obtained. Agent. Further, for example, in the case of a C 丄 pigment having a hydrogen atom bonded to a diketopyrrolopyrrole skeleton and red 264 (the following formula (5)), although the sulfonation is carried out in the case where the solution does not occur, However, the crystallinity is extremely poor. It is considered that the reason is that a plurality of chemical species (ehemieal speeies) are generated, but the crystallinity is so poor that it is difficult to separate or wash the product into the crucible. That is, since the 200936703 can not be fully washed, the obtained pigment can be used in the liquid crystal filter m π special resist, for example, if it is used for the sulphuric acid residue in the squeegee auxiliaries. Then it produces a problem with the reduction of ι·μμs❶

X = (3) and H〇K: h3 (4) 丄 C 丄 ( (4) 71 in which two 3-cyanophenyl groups are bonded to the diketone base enthalpy skeleton (in the case of the present invention), especially Solving the problem of decomposition and the problem of crystallinity 'by using it as a first-resistance agent for liquid crystal colorors', it is possible to obtain a color filter for liquid crystal with good contrast or brightness. Next, a pigment dispersion containing an organic pigment, a pigment dispersant, the above pigment dispersing aid, and an organic solvent will be described.颜料 The amount of the pigment dispersing aid constituting the pigment dispersion of the present invention is usually 〇1 to 1% by mass, preferably S0 by mass/〇, based on the organic pigment (100% by mass). There is a tendency that the amount of the pigment dispersing aid to be used does not further increase even if the amount of the pigment dispersing aid exceeds the above range. The organic pigment constituting the pigment dispersion of the present invention can be used from a conventional printing ink, a coating, a photoresist for a liquid crystal color filter, an ink for use in an inkjet ink, a diketopyrrolopyrrole pigment. , condensed monomer pigment, isoindoline pigment, perinone pigment, Perylene pigment, azo pigment with heterocyclic ring, benzoimidazolone At least one red pigment selected from the group consisting of pigments, brewing pigments, 20090丫 π 200936703 quinacridone pigments and dibr〇m〇anthanthrone pigments , yellow pigment, orange pigment and purple pigment. Further, when a specific example is indicated by a generic name such as a color index, the red pigment may be, for example, CI Pigment Red 9, 19, 38, 43, 48, 49, 52, 53, 57, 88, 97, 122, 123, 144, 146, 149, 155, 166, 168, 177, 178, 179, 180, 185, 188, 190, 202, 206, 207, 208, 209, 216, 217, 220, 221, 224, 226, 238, 242, 254, 255, 264, etc.; yellow pigment, which can be exemplified by pigment yellow us, 139, 150, etc.; ◎ 桎 color pigment, which can be cited as CI pigment dial 38, 43, 71, etc.; For example, CI Pigment Violet 23 and the like can be mentioned. Among these, it is preferably a di-based group from the viewpoint of obtaining a good color tone as a photoresist for a liquid crystal color filter. Bilo. Among the diketopyrrolopyrrole pigments, CI•Pigment Red 25 4 is preferable from the viewpoint of obtaining a high luminance Y value and obtaining a high-quality photoresist for a liquid crystal color filter. In the present invention, the amount of the above organic pigment in the above pigment dispersion (% by mass%) is preferably from 1 to 4 Å by mass. The organic pigment is preferably microparticulated for the chromaticity of k inkjet printing and the luminance gamma value and contrast of the liquid crystal color filter. Further, it is more preferably an organic pigment: a kneading machine or a kneading device that revolves three sets of stirring wings while performing a revolving motion, and the organic pigment is ground by an inorganic salt to perform salt grinding treatment to make an organic The primary granules of the pigment reach a finer grain. Among them, it is preferred to use an organic pigment obtained by salt-milling a kneading device in which three stirring 12 200936703 $ are rotated and the surface is revolved. In this case, a salt milling treatment may be performed to make the primary particle diameter of the pigment finer and ^ ^ » a kneading device that performs a revolving motion while rotating the 3 = kneading surface, respectively, is also referred to as Trimix. deal with. Eight reports ^ ^ Μ * processing, refers to the international public W〇G6/G98261 △ report and other s contained in the processing. Specifically, the above-mentioned Trimix treatment is carried out by: = containing an organic pigment, a water-soluble inorganic salt (a gasified sodium, etc., preferably an average particle: the one below), and substantially not dissolving the above inorganic salt. The mixture of the water-soluble dispersion medium (the ethoxyl alcohols, the glycols, the screams, etc.) is subjected to the mixing motion of the mixing wing _ surface, and the mixing and polishing of the surface is performed, and the above inorganic salts and domains are removed. A water-soluble dispersion medium. Further, in the production of the pigment dispersion of the present invention, a pigment dispersant, a pigment dispersion oxime aid, and an organic solvent may be added to the pre-advanced Tnmix-treated organic pigment, or may be added in the state in which the materials are added. Trimix processing. The pigment dispersion constituting the pigment dispersion of the present invention can be preferably used, for example, as a basic base. By using the above pigment dispersant together with the above pigment dispersing aid, the pigment dispersibility, dispersion stability, and fluidity can be particularly improved. Further, when a pigment dispersion having the above characteristics is used in the case of a photoresist composition, it is possible to exhibit high brightness or contrast. The above-mentioned pigment-dispersing agent having a basic group can be used, for example, a previously used printing ink, a dope material, a photoresist for a liquid crystal color filter, an ink for inkjet printing, and the like, and an inspective polymer pigment dispersing agent used in 200936703, for example, The following are available. The pigment dispersant is appropriately selected depending on the type of the organic pigment to be used, the type of the organic solvent to be used, and the like. (1) Amines and/or imines of polyamine compounds (for example, polyamines such as polyacrylamide, polyvinylamine, polyethylene polyamine, etc.) a reaction product of at least one selected from the group consisting of a polyester having a free rebel group, a polyamidamine, and a polyester decylamine (Japanese Patent Laid-Open Publication No. 2001-59906); (2) Molecule Each having at least one side chain selected from the group consisting of a polyester side chain, a polyether side chain, and a polyacrylic acid side chain, and a basic nitrogen-containing carbodiimide a compound (International Publication No. WO 04/000950); (3) a low molecular weight amine compound such as a poly(lower) alkyleneimine or a methylimidodipropylamine, and a polyester having a free carboxyl group. (4) In order to contain an alcohol such as methoxypolyethylene glycol or a caprolactone polyester, etc., in order to contain a reaction product (Japanese Patent Laid-Open No. Hei. No. Hei. No. Hei. No. Hei. Ο 1 hydroxyl-based polyester, containing 2 to 3 isocyanate-reactive functional groups A reaction product obtained by reacting an aliphatic or heterocyclic hydrocarbon compound containing an isocyanate group-reactive functional group and a tertiary amino group with an isocyanate group of a polyisocyanate compound (Japanese Patent Laid-Open Publication No. Hei 02-612) (5) a reaction product obtained by reacting a polyisocyanate compound and an amine group-containing hydrocarbon compound with an alcoholic hydroxyl group-containing acrylate polymer; (6) adding a polyether chain to a low molecular weight amine compound; (Reaction product formed by reacting a compound containing an amine group with an isocyanate group (Japanese Patent Laid-Open Publication); (8) Making a free carboxyl group a reaction product of a linear polymer and an organic amine compound containing one secondary amine group and a polyepoxy compound (Japanese Patent Laid-Open Publication No. Hei 09-87537); (9) an amine group at the terminal A reaction product of a reaction-reactive polycarbonate compound and a polyamine compound (Japanese Patent Laid-Open Publication No. Hei 9-194585), (10) selected from the group consisting of decyl methacrylate and methacryl Ethyl ester, propyl methacrylate, butyl methacrylate, octadecyl decyl acrylate, benzyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, acrylic acid At least one of methacrylic acid vinegar and acrylate such as octaalkyl ester or benzyl acrylate, and acrylamide, methacrylamide, N-methylbenzylamine, vinylimidazole, vinylpyridine, a copolymer of at least one of a polymerizable monomer having an organic group such as an amine group and a polyvalent internal vinegar skeleton, and at least one of styrene, a styrene derivative, and another polymerizable monomer ( Japanese Patent Laid-Open No. 164429 (11) An acrylic block composed of a block containing a basic group such as a tertiary amino group, a quaternary ammonium salt, or a block having no basic function. Copolymer or the like (indicative column of the acrylic block copolymer described in the specification of JP-A-2005-55814); (12) Michael addition reaction of a polycarbonate compound and a polyacrylamide Pigment dispersant obtained (Japan 15 200936703 Li Kaikai 09-194585); (13) Dt* - ^ @ compounds containing at least one polybutadiene chain and a basic nitrogen-containing compound (Japanese Patent Tetsu 2 257 (4) (14) The inside of the knife is a carbonized di-iminoimide compound containing at least one side chain having a mercapto group and a nitrogen-containing group (Japanese Patent Laid-Open No. 2006-176657); 15) a polyamine vinegar compound having a constituent unit having an ethylene oxide chain and a propylene oxide chain and having an quaternary four-staged amine group (Japanese Patent Application No. 2008-16404); a compound obtained by reacting an isocyanato group of an isocyanuric acid compound having a heterotrimeric phthalate ring in the molecule with an active hydrogen having a compound containing an active hydrogen and a carbazole ring in the molecule; The intrinsic taste ring of the compound is produced by reacting an isocyanate compound derived from an isocyanate ring with a cyanate cis group or by reacting the isocyanate group with an active hydrogen group. The total number of the three amounts of the amine ester bond and the urea bond is 15 to 85% (Japanese Patent Application) Gazette No. 2008-253235). In the pigment dispersion of the present invention, the amount of the above-mentioned pigment dispersant is usually from 1 to 200% by mass, based on 1 part by mass of the total organic pigment to be used, preferably from 1 to 60 parts by mass. If the amount of the pigment dispersant used is less than 1 mass damage, the pigment dispersibility may be lowered, which may be undesirable. On the other hand, when it exceeds 200 mass parts, the developability may fall, etc., and it is unpreferable. The organic solvent constituting the pigment dispersion of the present invention is, for example, an organic solvent suitable for use in an ink coating liquid crystal chrome photoresist and an ink jet. 200936703 Specifically, 'can be exemplified by one's worth. ・ Ethyl alcohol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl rough, ethylene dioxane beta early J ether, diethylene glycol monomethyl ether, diethylene glycol Alcohol single-mystery, propylene glycol Yanjia-1 - drunken methyl ether propylene glycol monoethyl ether, propylene glycol monobutyl ether, ❹ 乙醇 ethanol monoethyl ether, diethylene glycol dimethyl ether, diethylene glycol oxime ether and other ethers organic / Mixture 'ethylene glycol monomethyl hexanoic acid brewing, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl (10) acetic acid, propylene glycol monomethyl ether acetate g, two glycol monoethyl ether acetate and other ether ester organic solvents; Isobutyl ketone, hexanone, 2-heptanone, butyl, etc. _ organic solvent; 2-propionic acid f vinegar, 2-propyl propyl propionate, 2 hydroxy _2 methyl Ethyl acetate, 3-methyl-3-methoxybutyrate propionate, 3-methoxypropionic acid formazan, 3-methoxypropionic acid ethyl acetate, % ethoxypropionic acid methyl^3· Ethoxypropyl propionate, ethoxyacetic acid ethyl acetate, transacetic acid ethyl acetate? Acid-based acetal-based organic solvent; alcoholic solvents such as methanol, ethyl alcohol, isopropanol, butanol; N-methylpyrrolidone, N,N-dimethylformamide, N'N-methyl A nitrogen-containing organic solvent such as acetamide. These may be used alone or in combination of two or more. The above organic refrigerant can be appropriately selected depending on the use of the pigment dispersion or the desired physical properties. The pigment dispersion of the present invention can be produced by using the above-mentioned constituent materials, and can be produced by a conventionally known production method, for example, by the following production method. First, 'a mixture of an organic pigment, a pigment dispersing aid represented by the general formula (1), a pigment dispersing agent, and an organic solvent is obtained, using a roll mill, a kneader, a high-money mixing device, a bead mill, a ball mill, and a sand. Mill Ultrasonic Wave (4), High Pressure Μ (4) Various Finances The mixture was kneaded and subjected to dispersion treatment to obtain a pigment dispersion. Further, the pigment dispersion of the present invention may contain a binder resin (alkali-soluble resin 'photopolymerizable compound, etc.) in advance. The pigment dispersion thus obtained may contain various binder resins, surfactants, and other various additives as needed, and is applicable to printing inks, coatings, photoresists for liquid crystal color filters, inks for inkjet, and inks for writing instruments. , ribbon ink, liquid developer and other applications. Next, a preferred embodiment of the pigment dispersion of the present invention, that is, a pigment dispersion photoresist composition for a color filter, will be described in more detail.颜料 The pigment-dispersing photoresist composition for a color filter is a photoresist composition having active energy ray-curing property and capable of performing an in-progressive development; in addition to the above pigment dispersion, a soluble resin or a photopolymerizable compound is appropriately contained. The photopolymerization initiator may optionally contain various additives such as an organic solvent, a thermal polymerization inhibitor, a decane coupling agent or a titanate coupling agent for improving adhesion to a substrate, a UV absorber, and an antioxidant.

The total solid content of the organic pigment constituting the composition of the pigment dispersion resist for the color former of the present invention is the total solid content of the pigment dispersion resist composition for the color former, and the total mass of the organic pigment used is 质量' The amount is preferably from 5 to 80% by mass, more preferably from 20 to 50% by mass. In the pigment dispersion resist composition for a color filter, the amount of the pigment dispersant used is usually a mass fraction of 10 parts by mass, preferably 1 to 50 parts by mass, based on the mass parts of the organic pigment. If the amount is less than 丨, the pigment dispersion ^ sometimes decreases. On the other hand, if it exceeds 100 parts by mass, the developability may be lowered. In the above pigment dispersion resist composition for a color filter, the amount of the pigment dispersing aid used is usually 〇〇 mass with respect to 18 200936703 color pigment. Preferably, it is 5 to 50% by mass. There is a tendency that the pigment component does not further increase even if it exceeds 100% by mass. The soluble resin constituting the pigment-dispersed photoresist composition for a color filter of the present invention, as long as it is a developer used in the development processing step in the production of the color filter, and particularly preferably soluble in the alkaline developer, There is no particular limitation. Among them, an alkali-soluble resin having a carboxyl group is preferred, and a copolymer of an ethylenically unsaturated monomer having one or more carboxyl groups and another ethylenically unsaturated monomer copolymerizable with each other is particularly preferred. Specific examples thereof include an ethylenically unsaturated monomer having a carboxyl group such as acrylic acid or methacrylic acid, and a styrene or acrylic acid 2-hydroxyl group selected from copolymerizable with an ethylenically unsaturated monomer having a carboxyl group. Ester, 2-hydroxyethyl methacrylate, allyl acrylate, propyl methacrylate, benzyl acrylate, benzyl methacrylate, cyclohexyl acrylate, cyclohexyl methacrylate, glyceryl monoacrylate, Group consisting of methacrylic acid glycerol 'n-phenyl maleimide, polystyrene macromonomer (macr〇m〇n〇mer) and polymethylmethicone dilute acid vinegar macromonomer a copolymer formed by at least one of the ethylenically unsaturated monomers. The acid value of the above copolymer is preferably from 50 to 300 mgKOH/g. In this case, if the acid value is less than 50 mgKOH/g, the solubility of the photoresist composition to the alkali developer tends to decrease. On the other hand, when it exceeds 3 〇〇mgKOH/g, the solubility in an alkaline developing solution is too large, and the tendency of the colored layer to fall off from the substrate or the surface of the colored layer to be rough is likely to occur when developing with an alkaline developing solution. . Further, in the present invention, the acid value is the theoretical acid value, which is obtained by arithmetic calculation based on the ethylenically unsaturated monomer having a carboxyl group and the amount thereof used. The weight average molecular weight of the soluble resin in the present invention is usually preferably from 1,000 to 100,000. If the weight average molecular weight of the bismuth soluble resin is less than 1,000, the solubility to the alkaline developer may increase and the development characteristics may deteriorate. On the other hand, if it exceeds 100,000, the solubility in an organic solvent may decrease and the viscosity of the photoresist composition may increase. Further, in the present invention, the weight-averaged amount of the alkali-soluble resin is a weight average molecular weight in terms of polystyrene obtained by GPC (gel permeation chr〇 mat〇graph). In the present invention, Water 2690 (manufactured by Waters Corporation) was used for the apparatus, and Plgel 5 /z MIXED-D (manufactured by P〇lymer Laboratories Co., Ltd.) was used for the column. In the pigment-dispersed photoresist composition for a color filter of the present invention, the alkali-soluble resin is usually used in an amount of 10 to 1,000 parts by mass, preferably 2%, based on 100 parts by mass of the total of the total of the organic pigments to be used. ~ 5 〇〇 mass parts. If the amount of the soluble resin used is less than 1 Gf, (4) if there is (4) a drop in the shadow, or a scum or residual film on the unexposed portion of the substrate or the light-shielding layer. Another-side's if exceeded! In the case of _ parts by mass, the concentration of the organic pigment is relatively lowered, so that it is difficult to achieve a desired color density as a thin medium. Hereinafter, the photopolymerizable compound constituting the pigment-dispersing photoresist composition for a color filter of the present invention will be described. The photopolymerizable compound may, for example, be a monomer or an oligomer having a polymerizable unsaturated bond in the molecule. The term "photopolymerizable unsaturated bond" refers to an unsaturated state in which polymerization can be carried out by the action of a radical or a cation generated by decomposition of an active energy ray such as ultraviolet rays or electron beams by the following photopolymerization initiator. key. The monomer having one photopolymerizable unsaturated bond in the sub-group can be exemplified by decyl methacrylate, butyl methacrylate, dimethyl hexyl methacrylate, methyl acrylate, butyl acrylate, acrylic acid. An alkyl methacrylate or an alkyl acrylate such as 2-ethylhexyl ester; an aralkyl methacrylate or an aryl acrylate such as benzyl methacrylate or benzyl acrylate; Ethyl alkoxyalkyl methacrylate or alkoxyalkyl acrylate such as ethyl or butyl acrylate; n, n-didecylaminoethyl methacrylate, N, N-dimethyl acrylate Aminoalkyl methacrylate or aminoalkyl acrylate such as arylaminoethyl ester; methyl group of polyalkylene glycol alkyl ether such as diethylene glycol diethyl ether, triethylene glycol butyl ether or dipropylene glycol methyl ether Acrylate or acrylate; methacrylate or acrylate of polyalkylene glycol aryl ether such as hexaethylene glycol phenyl ether; isobornyl methacrylate or isobornyl acrylate; glyceryl decyl acrylate or glycerol Ester; 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate Wait. Further, a monomer having two or more photopolymerizable unsaturated bonds in the molecule is exemplified by bisphenol A dimethacrylate, I, 4 · butanediol dimethyl acrylate, and 1,3- Butanediol dimercapto acrylate, diethylene glycol dimethacrylate, glyceryl dimethacrylate, neopentyl glycol dimercapto acrylate, polyethylene glycol dimethacrylate, polypropylene glycol Acrylate, tetraethylene glycol dimercapto acrylate, trimethylolpropane trimethacrylate vinegar, season 21 200936703 pentaerythritol trimethacrylate vinegar, pentaerythritol

Ann knot m 四 tetramethacrylate, dipentaerythritol tetramethacrylate, second-hand ^ ^ ^ mannitol hexamethacrylate, dipentaerythritol penta methacrylate, double-work ratio acrylate '1, 4-butanediol-acrylic acid, 1,3-butanediol dipropylene vinegar, glycerin diacrylate, neopentyl alcohol_"-ethylidene alcohol-acrylic acid pentyl alcohol-acrylate, polyethylene glycol Diacrylate vinegar, polypropylene glycol diisopropyl propylene glycol diacrylate, dimethoprimic triacrylate, pentylene tetraacetate diacrylate, pentaerythritol: oleic acid vinegar, dipentaerythritol tetraacrylic acid, Dipentaerythritol

Known by bismuth, pentaerythritol pentaacrylate, etc. The monomer may be used singly or in combination of two or more. In the invention, the amount of the photopolymerizable compound used as the total solid content in the pigment-dispersing photoresist composition for the color filter is preferably in the range of 3 to 5 % by mass based on the mass fraction.

The photopolymerization initiator "constituting the pigment-dispersing photoresist composition for a filter device of the present invention" is not particularly limited as long as it generates radicals or cations by irradiation with an active energy ray such as ultraviolet rays or electron beams, and examples thereof include, for example: Benzophenone, N,N,-tetraethyl-4,4,diaminobenzophenone, 4·methoxy-4, dimethylaminobenzophenone, benzoin ( Benzil), 2,2-diethoxyacetophenone, benzoin, benzoin methyl ether, benzoin isobutyl ether, benzyl dimethyl condensed net, α-isobutyl butyl ketone (a _hydr〇xyis〇butylphen〇 Ne), thioxanthone, 2-oxothioxanthone, 1-hydroxycyclohexyl phenyl ketone, tert-butyl fluorene' 1- gas oxime, 2,3-dichloropurine, 3- Chloro-2-f 蒽醌 蒽醌 ' 2 · ethyl 蒽, 1,4-naphthoquinone, ι, 2-benzopyrene, ι, 4- bis fluorenyl, 2 phenyl hydrazine, 2 -f-methylthio)phenylj_2_morpholinylpropane-丨-嗣, triazine 22 200936703 Photopolymerization initiation Xie Zun. The above combination is used alone or in the present invention, and the amount of the initiator is preferably used as the amount of the pigment-dispersed photoresist group relative to the total solid I* in the above-mentioned filtrate. According to proton 乂 1 main horse 1 to 20% by mass range. The pigment component constituting the color filter of the present invention is organically dissolved under the above-mentioned pigment octa-resistance agent, and the boiling point of the sample is preferably 100 (3) 3...2 η) ~22〇t tanning agent, (4) organic solvent, organic entrapment agent, (4) organic soluble nitrogen-containing organic solvent, etc., organic gluten, aromatic smog solvent and these organic solvents, and practice , By. 〇 〇 〇 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 与 六 与 与Diethylene glycol methyl ether, ethylene glycol monomethyl acetate, propylene glycol monomethyl acetic acid, propylene glycol monoethyl ether, cyclohexanone, 2-glyoxime, 2-hydroxypropyl propionate, propionic acid % methyl butyl butyl acrylate, ethyl 3-methoxypropionate, methyl ethoxy propyl propionate, methyl n-pentyl pentyl ester, etc., more preferably propylene glycol monoacetic acid vinegar. The towel is used for the solubility of the soluble resin, the pigment dispersibility, the cloth, and the like. In the total organic solvent used in the pigment-dispersed photoresist composition for a color filter of the present invention, The content of the organic solvent is preferably 50% by mass. More preferably, it is 7 〇 mass% or more. Further, when the right side contains a large amount of an organic solvent having a boiling point of more than 22 〇〇c, the organic solvent may not be sufficiently dried in the pre-baking of the coating film formed by the coating on the moon b. 200936703 evaporation and remaining in the dried coating film. Moreover, the heat resistance of the dried coating film is lowered. In addition, when a large amount of organic solvent having a boiling point of less than 10 (rc is used, it may be difficult to apply a flat coating), and a coating film having excellent surface smoothness may not be obtained. The pigment-dispersed photoresist composition for a color filter of the present invention In addition, various additives such as other photopolymerizable compounds, thermal polymerization inhibitors, ultraviolet absorbers, and antioxidants may be appropriately used as needed. Hereinafter, a method of producing the pigment dispersion resist composition for color filters of the present invention by using the above constituent materials may be employed. Description.

The method for producing a pigment-dispersed photoresist composition for a color filter of the present invention is an example of the preferred embodiment of the present invention. The present invention is not limited thereto. In order to manufacture the composition-dispersed photoresist composition for a color filter of the present invention from the constituent materials described above, the following method may be employed: the photopolymerizable compound is added to the pigment dispersion obtained by the above method, and photopolymerization is started. The sword is tested for soluble resin, and an organic solvent and other additives are added as needed, and stirred and mixed by a stirring device or the like.

The pigment dispersing aid of the present invention having the above-described constitution can be efficiently produced by using sulfuric acid or fuming sulfuric acid, and exhibits excellent (iv) dispersibility q by using in combination with a pigment dispersing agent. The dispersing aid can obtain a pigment dispersion which has good fluidity and dispersion stability even in a state in which the organic pigment is finely dispersed. The pigment dispersion is excellent in brightness and chromaticity. Therefore, it can be applied to inks for ink jet printers in addition to various printing inks. Further, the dispersion is used for a liquid crystal color filter having a luminance gamma value or contrast in a photoresist for a liquid crystal coloror. The present invention can be more specifically described by the following examples, but the present invention is not limited to the examples. In addition, unless otherwise specified, "〇" means "quality 1%" and "part" means "mass portion". In addition, in this specification, "Trimix" is a registered trademark of Inoue Manufacturing Co., Ltd., "Irgacure" is a registered trademark of Ciba Speciahy Chemicals Co., Ltd., and "Disperbyk" is a registration of BYK Chemie Co., Ltd. trademark. <Pigment Dispersing Aid> [Pigment Dispersing Aid 1] To a 100 ml Erlenmeyer flask, 30 ml of concentrated sulfuric acid was added, and the surface was stirred with a magnetic stirrer to introduce a 1 g g of the CI pigment lamp 71 (in the above formula). (2) The compound represented, trade name: DPP 〇range TR, manufactured by Ciba Specialty Chemicals Co., Ltd.), and stirred at room temperature for 30 minutes. A mixture of 5 g of water and 50 g of ice was added to a 1 L beaker, and the above reaction was poured into the ice water to be stirred in a magnetic stirrer for 30 minutes. The obtained solid was dried under reduced pressure, and the obtained solid was dried to obtain 12 g of the pigment dispersing aid 1 represented by the following chemical formula (6). 25 200936703

[Pigment Dispersing Aid 2] 加入 Add 30 nu of concentrated sulfuric acid to a 100 ml Erlenmeyer flask and mix with a magnetic stirrer - 1 G g of CI Pigment Red (5) (expressed by the above formula (3) The compound was stirred at room temperature for 3 minutes, and a mixture of 50 g of water and 50 g of ice was added to the beaker, and the above reactant was poured into the ice water to magnetic force (tetra) H (tetra) for 3 G minutes. It was filtered under reduced pressure, washed with water, and the resulting solid was dried, *Hong w v «agent 2. Chad Ug pigment dispersion aid [Pigment Dispersing Aid 3]

Add 3 〇 (6) of concentrated sulfuric acid to the Erlenmeyer flask of Π Π Π 一面 while stirring with a magnetic stirrer and put 1 〇丄丨 (4) 斛 main and then 1 () 8 C.1. Pigment Red 272 (in the above formula ) the compound shown) was stirred at room temperature for 3 minutes. Add 50 g of water and 50 § ice to the i cup. ^ O' Μ (4) (4) Mix for 3G minutes. This was carried out under reduced pressure.馒 12 12 g of pigment dispersion help 26 200936703

I

[Pigment Dispersing Aid 4] Add 30 ml of concentrated sulfuric acid to a 100 ml Erlenmeyer flask, and add 10 § CI Pigment Red 264 (the compound represented by the above formula (5)) while stirring with a magnetic stirrer. Stir at room temperature for 3 minutes. A mixture of 50 g of water and 50 g of ice was added to the beaker of i l, and the above reactant was poured into the ice water, and stirred by a magnetic stirrer for 3 minutes. This was subjected to a transition and water washing under reduced pressure, but the crystallinity was poor, it was difficult to sufficiently wash the water, and the obtained solid was dried to obtain 14 g of the pigment dispersing aid 4. Ο [Pigment Dispersing Aid 5]

<Organic Pigment> [Preparation Example 1] (Trimix treatment Yanke Red 254) The tank manufactured by the company is supplied to Trimix ΤΧ-15 (Inoue Manufacturing Co., Ltd. 27 200936703 - 750 parts by mass of CI Pigment Red 254, 7500 A mass fraction of 2 〇Mm of vaporized sodium and 1800 parts by mass of diethylene glycol, and kneaded at 45 ° C for 3 hours in a range of 70% of the rated current value of 9·3 A, and salt Then, 1300 parts by mass of the obtained kneaded product was put into 3 liters of warm water, and the mixture was stirred for 1 hour while being heated to 70 〇C to form a slurry. The gasification was repeated, and the sodium carbonate and diethylene glycol were removed by washing with water. Then, it was dried overnight at 4 ° ec, and 95 parts by mass of Trimix-treated Pigment Red 254 (Trimix-treated PR254) was obtained. [Preparation Example 2] (Salt-Processing of Pigment Red 254 using a kneader) 0-direction kneading machine ( Product name: KHD-2 'manufactured by Inoue Co., Ltd.), 1 part by mass of CI Pigment Red 2M, 1 〇〇〇 quality of grain control 20 //m gasification, 240 parts by mass Diethylene glycol, mixed for 1 hr at 75 C, and subjected to salt milling. Next, 丄3 The obtained kneaded product was put into 3 liters of warm water and heated to 7 Torr. The mixture was stirred for 1 hour to form a slurry. The filtration was repeated, washed with water to remove sodium and ethylene glycol, and then at 40 ° C. Drying was carried out to obtain 95 parts by mass of a salt mill-treated Pigment Red 254 (kneader-treated PR254). Ο <A pigment dispersant containing a basic group>

Disperbyk_2001 (hereinafter referred to as DB-2001; manufactured by BYK-Chemie, a basic-based acrylic block copolymer)

Ajisper822 (hereinafter, also referred to as PB_822; Ajin〇m〇t〇 Fine-Techno, a copolymer containing a basic functional group) <alkali-soluble resin>

BzMA/MAA copolymer (benzyl methacrylate/methacrylic acid copolymer 28 200936703, _, theoretical acid value: 120 mgKOH/g, weight average molecular weight: 25,000) <photopolymerizable compound> DPEHA (dipentaerythritol Acrylate) <Photopolymerization Initiator>

Irgacure 907 (manufactured by Ciba Specialty Chemicals Co., Ltd., 2-methyl-1-[4-(methylthio)phenyl]-2-morpholinylpropane-buxan&lt;organic solvent&gt; PGMEA (propylene glycol single曱_acetate) 〇 <Pigment Dispersion> The composition of Table 1 was kneaded by a bead mill at a temperature of 40 to 50 ° C for 3 hours to obtain a pigment dispersion. Further, the unit of the numerical value of the composition was mass. &lt;Pigment Dispersion Resist Composition for Color Filter&gt; The pigment dispersion was uniformly mixed with other materials by a high-speed mixer in the form of the composition of Table 1, and then filtered by a filter having a pore size of 3 #m The pigment dispersion resist composition for a color filter was obtained. The unit of the numerical value of the composition is shown in parts by mass. (Evaluation method) The following evaluations were carried out, and the results are shown in Table 2. &lt;Viscosity&gt; The pigment dispersion photoresist composition for the color filter of the example and the comparative example was taken into a glass bottle separately and was stoppered and stored at room temperature for one day, and then manufactured by an E-plastic viscometer (Dongji Industry Co., Ltd., The R1〇〇 viscometer model RE100L) was measured at 25. (: The viscosity is lower. The lower the viscosity, the better the flow is. 200936703 The better the method is, the method is measured. The expression is excellent as a pigment dispersion. It is expressed in the 生 砉 士 衣 衣 2, which means “beyond the above E-type viscometer. High viscosity of the determination limit &lt;dispersion stability&gt;

For the examples and the composition of the smear-filtered disperse green agent, respectively, they were taken into a glass bottle and stoppered with a stopper. The Lishaw e-type viscometer was measured at room temperature for 1 day and then stored under hunger viscosity. Viscosity after 7 days. The dispersion stability was determined by (4 (viscosity after 7 days of storage in rc) / (viscosity after storage for 1 day at room temperature), and was evaluated as "gel" in Table 2. The dispersion stability was poor and gelled during the evaluation. <Contrast of the pigment-dispersed photoresist composition for a color filter> The pigment-dispersed photoresist composition for color filters of the examples and the comparative examples was coated with a spin coater. The cloth was placed on a glass substrate to have a thickness of 1 Å, pre-baked at 100 ° C for 3 minutes, exposed by a high-pressure mercury lamp, and further baked at 230 ° C for 30 minutes. Two polarizing plates (manufactured by Mindong Electric Co., Ltd., model: 〇SEG1224DU) sandwiched the glass substrate coated with the photoresist composition, and irradiated one side with a fluorescent lamp (wavelength range of 380 to 780 nm) to polarize the front side. When the plate is rotated 'in the case where the polarizing plate on the front side is parallel to the polarizing surface of the polarizing plate on the rear side and at right angles', the intensity of light transmitted at this time is measured by a color luminance meter (manufactured by Topcon Corporation, BM-5A). The polarizing plate on the side and the polarizing surface of the polarizing plate on the back side are The ratio of the luminance at the time of parallelism and the luminance at the right angle to the polarizing surface of the polarizing plate on the rear side of the polarizing plate on the front side was evaluated as contrast. 30 200936703

I Contrast = (brightness when the polarizing plate on the front side is parallel to the polarizing surface of the polarizing plate on the rear side / brightness at the right angle of the polarizing plate on the front side and the polarizing plate on the rear side). Further, 'the contrast of the state in which the photoresist composition is not applied to the glass substrate, that is, the BareGlass value is 1000 〇&lt;the evaluation of the color characteristics of the pigment-dispersed photoresist composition for color filters&gt;&gt; using a spectrophotometer ( The color characteristics (X, y, γ) of each of the resists of the examples and the comparative examples in which the film thickness was 1 〇v claws were measured by Shimadzu Corporation, UV-2500PC, C light source 2 field of view. Here, in the examples and the ratios 4 & Comparative Examples 1 to 5, the chromaticity y and the luminance γ at the chromaticity Χ = 0.600 were obtained. Further, the breakthrough spectra of the coating films of the photoresist compositions of Example 1 and Comparative Example 5 were measured by a spectrophotometer (manufactured by Shimadzu Corporation, UV-2500PC), and are shown in Fig. 1. &lt;Evaluation of heat resistance of pigment dispersion resist composition for color filter&gt; The pigment dispersion resist composition for color filters of the examples and the comparative examples was applied onto a glass substrate by a spin coater. The film thickness was 1. 〇&quot; m, prebaked at 100 ° C for 3 minutes, exposed by a high pressure mercury lamp, and further baked at 270 ° C for 60 minutes. Thereafter, the surface of the obtained photoresist coating film was observed with a microscope (manufactured by Keyence Co., Ltd., vhS-500, magnification: 500 times), and the degree of surface cracking simultaneously with the sublimation of the pigment in post-baking was observed. The "sublimation foreign matter" in Table 2 means that the surface cracking at the same time as the sublimation of the pigment in the post-baking means that the heat resistance is poor. The micrographs of Example 比较 and Comparative Example 5 are shown in Fig. 2 as an observation example. 31 200936703 [Table i] Example 1 Example 2 Example 3 Example 4 Example 5 Comparative Example 1 Comparative Example 2 Comparative Example 3 Comparative Example 4 Comparative Example 5 Trimix Treatment PR254 15.0 - 15.0 15.0 15, 0 15.0 15.0 15.0 15.0 15.0 Kneading machine treatment PR254 — 15.0 — — — 一—一一—DB-2001 4.5 4.5 4.5 4.5 a4.5 4.5 4.5 4.5 4.5 PB-822 — - a - 4.5 pigment dispersion aid 1 0.8 0.8 3.0 4.5 0.8 — - - - - Material pigment dispersing aid 2 - one - - 0.8 - - - Dispersion pigment dispersing aid 3 - one - - - - - 0.8 - one pigment dispersion aid 剤 4 - - - - one - - - 0.8 A pigment dispersing aid 5 0.8 BMA/MAA copolymer 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4.5 4,5 4.5 PGMEA 75.2 75.2 73.0 71.5 75.2 76.0 75.2 75.2 75.2 75.2 — Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 Dispersion of materials婀Group of the above pigment dispersions 53.3 53.3 53.3 53.3 53.3 53.3 53.3 53.3 53.3 53.3 BMA/MAA copolymer 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7 5.7 DPEHA 3.4 3.4 3.4 3.4 3.4 3.4 3.4 3.4 3.4 3.4 Irgacure907 1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1 1.1 Adults PGMEA 36.5 36.5 36.5 36.5 36.5 36.5 36.5 36.5 36.5 36.5 Total 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 100.0 32 200936703 〇 33ο 4

For thermal contrast Υ: Brightness X Dispersion stability Dispersion composition viscosity (mPa · S) 1 No sublimation foreign matter 1 1.750 26.2 1 | 0.324 I 1 0.600 I | 1.03 I ·14·°· |Example ι| I No sublimation foreign body I 700 26.0 0.324 0.600 0.98 13.0 | Example 2 j I without sublimation foreign body I 800 1 26-4 | 0.325 0.600 — 1 15.3 1 Example 3 1 No sublimation foreign body 1 900 | 26.5 I 0.326 | 0.600 — 〇丨...Ί | Example 4 J 1 no sublimation foreign matter 1 700 1 26.4 | 0.324 0.600 Γ 1.05 I Γ 18.1 ] I Example 51 1 Sublimation foreign body 1 300 1 24-3 1 0.315 | | 0.600 | Gel 1 cannot be measured ι | ι| ί有升化外物1 [450 1 1 24.5 | I 0.318 1 0.600 Gel 1 cannot be measured | |Comparative Example 2 1 I Sublimation foreign body I 450 1 24.6 | 0.318 0.600 Gel|Unable to measure | Comparative Example 3 I None Sublimation Foreign Body I | 550 I | 25.0 I 1 0.321 | 0.600 | Gel Η-1 | Comparative Example 4 II Sublimation Foreign Body I 600 [26.5 | 0.327 I | 0.600 | b〇〇 | Comparative Example 5 I 200936703 It is confirmed that in the examples using the pigment dispersing aid of the present invention, it is not possible to obtain a pigment dispersing aid relative to the use of the present invention. The comparative examples of the same pigment dispersing aid are more excellent in fluidity and dispersion stability, and are superior in contrast, color characteristics and heat resistance. Among the pigments having a diketo-based oxo-pyrene-pyrrolidine skeleton, in particular, CI Pigment Orange 71 used in the present invention is used as a raw material, whereby the pigment dispersion can be stably obtained, and the diketopyrrolopyrrole skeleton can be used. In Comparative Examples 2 and 3, which have a pigment dispersing aid having a different substituent from the present invention, not only the viscosity of the pigment dispersion was high, but also the gelation with time was formed, and the dispersion effect was not exhibited at all. It is presumed that the reason is that the pigment is decomposed in the step of causing concentrated sulfuric acid to act on the pigment powder for sulfonation. In other words, it has been found that, even when a compound having a sulfo group introduced into a diketoppyrrolopyrrole skeleton having no substituent (Comparative Example 4) or a compound of a (4-) group introduced into an azo compound is used ( Comparative Example 5) also showed a fixed dispersibility as a pigment dispersing aid, but the stability over time was poor, and the contrast or brightness enthalpy was less than that of the examples and was insufficient. In particular, it was found that sublimation foreign matter was confirmed in the azo compound (Comparative Example 5), and heat resistance was inferior. Two _ base. Compared with the case of Bilo, the π knife scatter has an adverse effect. The pigment dispersion aid of the present invention as a raw material as described above has the same diketopypidine as the present invention.

The cleaning at the time of sulfonation cannot be sufficiently performed, however, 'Comparative Example 4 I and 0 are more than the Hakka skeleton, and the result is a sweep.

C.I. Pigment Orange 71 The dispersing aid has poor crystallinity, and some of the sulfuric acid residue shows that it has good crystallinity because of its good crystallinity. Therefore, it is also particularly advantageous for the use of a photoresist for liquid crystal color filters. Further, when the penetration spectra of Example 1 and Comparative Example 5 were compared, it was found that in the penetration spectrum of Example 1, the rise near 570 nm became sharp, and the transmittance near 610 nm was higher. Preferably, it is a preferred spectrum of the photoresist for a liquid crystal color filter (Fig. 1). Further, when the photographs of the surface of the photoresist coating film of Example 1 and Comparative Example 5 shown in Fig. 2 are compared, it is understood that the examples are as follows. The surface wrinkle which is produced at the same time as the sublimation of the pigment in the post-baking is significantly less. It is also known that the pigment dispersing aid of the present invention is particularly advantageous for the use of a photoresist for a liquid crystal color filter. The pigment dispersing aid of the present invention is applicable to various ink fields in addition to liquid crystal color filter photoresist or inkjet ink. [Simplified Schematic] FIG. 1 is the use of Example 1 or comparison. The pigment dispersing aid of Example 5 was used to produce a breakthrough spectrum of the pigment dispersion of c·1. Pigment Red 254. The solid line is the breakthrough spectrum when the pigment dispersing aid of Example 1 was used, and the broken line was used in Comparative Example 5. The penetration spectrum of the pigment dispersing aid. The surface state of the coating film after post-baking using the pigment dispersing aid of the pigment dispersing aid of Example 1 or Comparative Example 5. The left figure shows the case of using the pigment dispersing aid of Example 1, right The figure shows the case of using the pigment dispersing aid of Comparative Example 5. 35 200936703 [Description of main component symbols]

Claims (1)

200936703 VII. Patent application scope: 1. A pigment dispersing aid characterized in that it is a compound represented by the following formula (1) • H ——(S03M)m (1) [wherein Μ denotes that η and R4 are the same or different&gt; Na, Κ, ΝΗ4 or NRWR'Ri, R2, ' represents the carbon number which can also be substituted by other substituents μ A saturated or unsaturated aliphatic hydrocarbon group, or an aromatic hydrocarbon group having 6 to 10 carbon atoms which may be substituted by another substituent; m represents an integer of 丨 or more]. VIII. A pigment dispersion characterized by comprising: an organic pigment, a pigment granule, a pigment dispersing aid according to the scope of the patent application, and an organic solvent. 3. The pigment dispersion of the second aspect of the patent application wherein the pigment The dispersant has an experimental basis. 8. The pigment dispersion according to claim 2, wherein the pigment dispersant is an acrylic block copolymer having an auditing group. 5. The pigment dispersion according to any one of claims 2 to 4, 37 200936703 6. A pigment dispersion according to claim 5, wherein the bis-quino-pyrrolidene pigment is cu. Pigment Red 254. 7. A pigment dispersion according to any one of claims 2 to 6, wherein the organic pigment is micronized. 8. The pigment dispersion of claim 7, wherein the microparticulation treatment is a salt milling treatment. 9. The pigment dispersion according to claim 8 wherein the salt milling treatment is carried out by the following steps: coating the organic pigment, the water-soluble inorganic salt, and the water-soluble dispersion medium which does not substantially dissolve the ◎ inorganic salt. The mixture is removed by mixing the three mixing arms with one side of the mixing wing and performing a revolving motion on the surface to remove the inorganic salt and the water-soluble dispersion medium. And a pigment dispersion-dispersing composition for a color filter, which is characterized by the pigment dispersion of any one of items 2 to 9 of the 匕3 application. Eight, schema: 38