Coloring composition and color filter
By using sulfonate compounds as dispersion aids in the color filter of the liquid crystal display device, the dispersion of C.I. pigment purple 29 is improved, and the problem of difficult to achieve high sensitivity and good shape black patterns in the prior art are solved, and the problem is improved. The reliability and performance of the display device are achieved.
Patent Information
- Application Number
- CN202180017911.3
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Priority Date
- 2020-08-13
- Filing Date
- 2021-06-10
- Publication Date
- 2025-02-21
- Estimated Expiration
- 2041-06-10
AI Technical Summary
In the prior art, it is difficult to achieve high sensitivity and good-shaped black patterns in the color filter of the liquid crystal display device, and using conductive materials such as carbon as light shielding materials will reduce the reliability of the display device.
By using a sulfonate compound with a significantly reduced absorbance in the visible region compared with a general dye pigment derivative as a dispersion aid, the dispersion of C.I. pigment purple 29 is improved to form a dispersion liquid with a low viscosity.
High dispersion in the diol-based solvent is achieved, and poor curing of resist and reduced spectral purity are avoided, thereby improving the performance of the color filter and the reliability of the display device.
Smart Images

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Abstract
Description
Technical Field
[0001] The present invention relates to a coloring composition and a color filter. Background Art
[0002] In the field of liquid crystal display devices, liquid crystal panels that have introduced a color filter array (COA) that integrates a color filter substrate and a TFT array substrate have attracted attention. If COA is used, the precise alignment required when using the above two substrates is not required, and each pixel of the red, blue, and green color filter can be miniaturized to the maximum, thereby achieving high-definition liquid crystal panels.
[0003] For such a resin black matrix for COA, since high light-shielding property is required, thick film is required. However, as the film thickness of the resin black matrix increases, the difference in cross-linking density of the exposed part relative to the film thickness direction expands, so it is difficult to achieve high sensitivity and obtain a black pattern with a good shape. In addition, as a means of high light-shielding, a large amount of light-shielding materials have been tried, but when conductive materials such as carbon are used as light-shielding materials, the relative dielectric constant of the black matrix becomes high and the volume resistance decreases, thereby reducing the reliability of the display device.
[0004] In order to eliminate such a disadvantage, attempts have recently been actively made to use a black organic pigment composition (organic black matrix) obtained by mixing a chromatic organic pigment so as to obtain black color instead of carbon black for a light-shielding material.
[0005] Regarding the coloring composition and dispersion liquid for manufacturing the color filter as described above, for example, there are records in the following patent documents 1-4. In particular, when the perylene and the sulfonic acid derivative of the pigment are combined, the dispersion liquid viscosity is high. In addition, when the derivative is an organic pigment derivative, the absorbance in the visible region is high, and the hue changes compared with the colorant monomer. In addition, there is a problem that the absorbance in the ultraviolet region is high and ultraviolet curing is hindered.
[0006] Prior art literature
[0007] Patent Literature
[0008] Patent Document 1: Japanese Patent Application Publication No. 2005-213403
[0009] Patent Document 2: Japanese Patent Application Publication No. 2002-22922
[0010] Patent Document 3: Japanese Patent Application Publication No. 2009-69822
[0011] Patent Document 4: International Publication No. 2015 / 015962 Summary of the invention
[0012] Problems to be solved by the invention
[0013] As described in the above-mentioned patent documents 1-4, it is a well-known and common method in the industry to add a dye pigment derivative for the purpose of improving the dispersibility of a difficult-to-disperse dye pigment, but if a dye pigment derivative with high tinting power is added, the purity of the spectrum decreases, which becomes a problem. In color filter applications and display light shielding applications, dye pigments are required to have a high degree of dispersibility compared to coatings and inkjet applications.
[0014] In recent years, there is a demand for a coloring composition that can achieve high dispersion in a glycol solvent, and can be used in a display manufacturing process without causing poor curing of the resist or reduction in spectral purity, despite containing a perylene compound such as CI Pigment Violet 29 that is difficult to highly disperse in a glycol solvent used in the manufacturing process of a display light-shielding member (black matrix or black columnar spacer, black bank). Therefore, the subject of the present invention is to provide a coloring composition and a color filter that can solve the above-mentioned problems.
[0015] Methods for solving problems
[0016] The present inventors have conducted studies and found that the dispersibility in CI Pigment Violet 29 can be improved by using a compound having a sulfonate salt whose absorbance in the visible region is significantly lower than that of a general dye pigment derivative such as copper phthalocyanine sulfonic acid used to improve dispersibility as a dispersing aid.
[0017] The present inventors presume that the mechanism of the above-mentioned improvement in dispersibility is as follows.
[0018] Perylenes other than CI Pigment Violet 29 have low acidity due to substitution of the NH portion with high acidity. Therefore, the parent skeleton of the acidic derivative is adsorbed on the perylene, and the acidic group is adsorbed on the amine of the dispersant to disperse and reduce the viscosity. Therefore, the acid does not become excessive within the range of normal use (addition of about 1 to 20%). On the other hand, CI Pigment Violet 29 has an imide site NH with high acidity, which directly reacts with the dispersant amine. Therefore, if an acidic sulfonic acid derivative is added, the acid becomes excessive. From the perspective of the acid-base balance in the dispersion system, if the acid is excessive, the aggregation of the pigment is promoted and the viscosity becomes high. On the other hand, if the alkaline dispersant is excessive, the viscosity becomes high due to the entanglement of the dispersant polymers. Therefore, the sulfonate in the CI Pigment Violet 29 dispersion system can prevent the high viscosity caused by the entanglement of the above-mentioned dispersant molecules by reacting with the excess amine without increasing the acidity in the system.
[0019] That is, the present invention is as follows.
[0020] Item 1. A coloring composition comprising a sulfonate compound represented by the following formula (1) and CI Pigment Violet 29.
[0021] A-SO3M·nH2O Formula (1)
[0022] [In formula (1), A is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus or oxygen in its structure; M is one equivalent of a monovalent to trivalent cation other than H; and n is an integer of 0 to 5.]
[0023] Item 2. A coloring composition according to Item 1, wherein the sulfonate compound is an aqueous solution of the sulfonate compound obtained by mixing 0.5 parts of a sulfonate compound represented by the following formula (1) with 10 parts of pure water having a pH of 6 to 8, the pH of the aqueous solution being 2 to 12, and the maximum absorbance in the wavelength region of 380 to 780 nm measured in accordance with JIS K 0115:2004 being 10% or less of the maximum absorbance of CI Pigment Violet 29.
[0024] A-SO3M·nH2O Formula (1)
[0025] [In formula (1), A is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus or oxygen in its structure; M is one equivalent of a monovalent to trivalent cation other than H; and n is an integer of 0 to 5.]
[0026] Item 3. The coloring composition according to Item 2, wherein the pH of the aqueous solution of the sulfonate compound is 6 to 11.
[0027] Item 4. The coloring composition according to any one of Items 1 to 3, wherein the sulfonate compound represented by the above formula (1) is at least one sulfonate compound selected from the group consisting of benzenesulfonates, toluenesulfonates, naphthalenesulfonates, anthraquinonesulfonates, 2-morpholinoalkylsulfonates, allylsulfonates, (±)-10-camphorsulfonates, linear alkylsulfonates, and branched alkylsulfonates.
[0028] Item 5. The coloring composition according to any one of Items 1 to 4, wherein the sulfonate compound represented by the formula (1) is at least one compound selected from the group consisting of compounds represented by the following formulas (1-1) to (1-10), sodium 2-naphthalenesulfonate, sodium 2-morpholinoethanesulfonate, sodium p-toluenesulfonate, potassium methanesulfonate, sodium 3-mercapto-1-propanesulfonate, sodium allylsulfonate, sodium (±)-10-camphorsulfonate, and sodium 1-decanesulfonate;
[0029] [Chemistry 1]
[0030]
[0031] [Chemistry 2]
[0032]
[0033] [Chemistry 3]
[0034]
[0035] [Chemistry 4]
[0036]
[0037] [Chemistry 5]
[0038]
[0039] [Chemistry 6]
[0040]
[0041]
[0042] [Chemistry 7]
[0043]
[0044] [Chemistry 8]
[0045]
[0046] [Chemistry 9]
[0047]
[0048] [Chemistry 10]
[0049]
[0050] Item 6. A color filter comprising the colored composition according to any one of Items 1 to 5.
[0051] Effects of the Invention
[0052] The coloring composition of the present invention can obtain a dispersion having a particularly low viscosity compared to a coloring composition in which CI Pigment Violet 29 and a sulfonic acid derivative of a pigment are combined by combining CI Pigment Violet 29 and a sulfonic acid derivative of the pigment. In addition, the viscosity reduction effect when the sulfonate is added is greater than that of a coloring composition in which perylene other than CI Pigment Violet 29 is combined with a sulfonate. In the coloring composition of the present invention, since a non-pigment sulfonate derivative having a small absorbance in the visible region is used, the change in hue from the colorant monomer is small even after the derivative is added. In addition, since the absorbance in the ultraviolet region is small, ultraviolet curing is not hindered. DETAILED DESCRIPTION
[0053] [Coloring composition]
[0054] The coloring composition of the present invention contains a sulfonate compound represented by the following formula (1) and CI Pigment Violet 29 (hereinafter referred to as "PV29").
[0055] A-SO3M·nH2O Formula (1)
[0056] [In formula (1), A is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus or oxygen in its structure; M is one equivalent of a monovalent to trivalent cation other than H; and n is an integer of 0 to 5.]
[0057] Examples of the halogen of A in formula (1) include fluorine, chlorine, bromine, and iodine atoms. Examples of the hydrocarbon group having 1 to 20 carbon atoms include aromatic hydrocarbon groups having 6 to 20 carbon atoms such as benzene, toluene, xylene, naphthalene, and anthraquinone, and linear or branched alkyl groups having 1 to 12 carbon atoms. Examples of the monovalent to trivalent cations other than H of M include lithium, sodium, potassium, calcium, magnesium, titanium, chromium, aluminum, manganese, iron, copper, nickel, silver, gold, lead, and tin.
[0058] The sulfonate compound represented by the formula (1) is preferably at least one sulfonate compound selected from the group consisting of benzenesulfonate, toluenesulfonate, naphthalenesulfonate, anthraquinonesulfonate, 2-morpholinoalkylsulfonate, allylsulfonate, (±)-10-camphorsulfonate, linear alkylsulfonate, and branched alkylsulfonate. These sulfonate compounds can prevent the viscosity from increasing due to the entanglement of the dispersant molecules, and can particularly provide a low-viscosity dispersion by reacting with an excess of amine without increasing the acidity in the system.
[0059] The sulfonate compound represented by the above formula (1) is preferably at least one compound selected from the group consisting of compounds represented by the following formulas (1-1) to (1-10), sodium 2-naphthalenesulfonate, sodium 2-morpholinoethanesulfonate, sodium p-toluenesulfonate, potassium methanesulfonate, sodium 3-mercapto-1-propanesulfonate, sodium allylsulfonate, sodium (±)-10-camphorsulfonate and sodium 1-decanesulfonate.
[0060] [Chemistry 11]
[0061]
[0062] [Chemistry 12]
[0063]
[0064] [Chemistry 13]
[0065]
[0066] [Chemistry 14]
[0067]
[0068] [Chemistry 15]
[0069]
[0070] [Chemistry 16]
[0071]
[0072] [Chemistry 17]
[0073]
[0074] [Chemistry 18]
[0075]
[0076] [Chemistry 19]
[0077]
[0078] [Chemistry 20]
[0079]
[0080] In the colored composition of the present invention, the ratio of the sulfonate compound represented by the above formula (1) is, for example, 0.5 to 20 parts by mass, or preferably 1 to 5 parts by mass, relative to 100 parts by mass of PV29.
[0081] The coloring composition of the present invention may contain a perylene organic pigment other than PV29. Examples of such perylene organic pigments include CI Pigment Red 123, CI Pigment Red 149, CI Pigment Red 178, CI Pigment Red 179, CI Pigment Red 189, CI Pigment Red 190, CI Pigment Red 224, CI Pigment Red 228, CI Pigment Black 31, and CI Pigment Black 32.
[0082] In addition, in addition to the above-mentioned perylene organic pigments, in order to have light-shielding properties, other organic pigments can also be used in combination. As such organic pigments, blue organic pigments, yellow organic pigments, and red organic pigments can be cited. As these various colored organic pigments, based on the chemical structure, for example, organic pigments such as azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, indanthrene, and perylene can be cited. Below, the specific examples of the pigments that can be used in the present invention are represented by pigment numbers.
[0083] Examples of the blue organic pigment include CI Pigment Blue 1, 1:2, 9, 14, 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 17, 19, 25, 26, 27, 28, 29, 33, 35, 36, 56, 56:1, 60, 61, 61:1, 62, 63, 64, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79, and 80. Among these, CI Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 25, 26, 60, and 80 are preferably used, and CI Pigment Blue 15:6, 25, 26, 60, and 80 are more preferably used.
[0084] Examples of yellow organic pigments include CI Pigment Yellow 1, 1:1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 24, 31, 32, 34, 35, 35:1, 36, 36:1, 37, 37:1, 40, 41, 42, 43, 48, 53, 55, 61, 62, 62:1, 63, 65, 73, 74, 75, 81, 83, 87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 126, 127, 127:1, 128, 129, 133, 134 , 136, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184, 185, 188, 189, 190, 191, 191:1, 192, 193, 194, 195, 196, 197, 198, 199, 200, 202, 203, 204, 205, 206, 207, 208, 229, etc. Among them, CI Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, 185, and 229 are preferably used, and CI Pigment Yellow 83, 138, 139, 150, 180, 185, and 229 are more preferably used.
[0085] Examples of red organic pigments include CI Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48:1, 48:2, 48:3, 48:4, 49, 49:1, 49:2, 50:1, 52:1, 52:2, 53, 53:1, 53:2, 53:4 :3、57、57:1、57:2、58:4、60、63、63:1、63:2、64、64:1、68、69、81、81:1、81:2、81:3、81:4、83、88、90:1、101、101:1、104、108、108:1、109、112、113、114、122、123、144、146、147、1 49, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194, 200, 202, 206, 207, 208, 209, 210, 214, 216, 220, 221, 224, 230, 231, 232 , 233, 235, 236, 237, 238, 239, 242, 243, 245, 247, 249, 250, 251, 253, 254, 255, 256, 257, 258, 259, 260, 262, 263, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 274, 275, 276, etc. Among them, CI Pigment Red 48:1, 122, 168, 177, 202, 206, 207, 209, 224, 242, 254 can be preferably mentioned, and CI Pigment Red 177, 209, 224, 254 can be more preferably mentioned.
[0086] The primary particle size of the pigment in the coloring composition of the present invention such as PV29 is, for example, 20 to 150 nm, and preferably 20 to 100 nm to impart high light-shielding properties. If the primary particle size of the pigment exceeds 150 nm, the dispersion stability deteriorates, and as a result, light scattering may be easily caused.
[0087] The primary particle size of the pigment in the coloring composition of the present invention is obtained by dispersing the coloring composition in a solvent such as cyclohexanone, applying the dispersion on a colloidal film, taking a scanning electron microscope (TEM) image, measuring the sizes of 1000 particles in the image obtained, and taking the average value as the primary particle size of the pigment.
[0088] The pigment can be finely pulverized by a pulverization method such as dry pulverization or wet pulverization. However, as implemented in the present invention, solvent salt milling in which the pigment is kneaded for a long time at a high inorganic salt ratio is preferred.
[0089] In the present invention, green organic pigments, purple organic pigments, orange organic pigments, brown organic pigments, etc. may be used together to adjust the color tone as needed. As these other color organic pigments used together, organic pigments with an average primary particle size of 20 to 100 nm are also preferably used.
[0090] Examples of organic pigments of colors other than blue, yellow and red that are suitable for combined use include CI Pigment Green 7, 36, 58, 62, 63, CI Pigment Orange 13, 36, 38, 60, 62, 64, 71, 72, and CI Pigment Violet 19, 23, 37.
[0091] The organic pigments and their combinations used can obtain the required blackness of the target black matrix. It is common knowledge for those skilled in the art to form black by subtractive mixing of the three primary colors of blue, yellow and red, and there is no particular restriction on their mixing ratio. However, for example, when the total amount of organic pigments of each color of blue, yellow and red is set to 100% by mass conversion, each color is increased or decreased by plus or minus 7% and used together based on the mass basis, so that black can be adjusted.
[0092] When dispersing these organic pigment compositions in an organic solvent, a resin dispersant may be used to improve dispersibility and dispersion stability. The resin dispersant has the function of allowing the organic pigment to bind to the anchoring site and the compatible part to extend in the dispersion medium to form a dispersion, and is a different type of substance from the alkali-soluble resin and photopolymerizable monomer used in the preparation of the photosensitive composition described later.
[0093] As the resin dispersant, there can be mentioned substances having a polymer chain, such as polyurethane resin, polyethyleneimine, polyoxyethylene glycol diester, acrylic resin, polyester resin, etc. Among them, polyester resin dispersants and / or acrylic resin dispersants are preferred from the viewpoints of dispersibility, heat resistance, and light resistance.
[0094] Specific examples of various resin-based dispersants include, by trade name, Ajisper (manufactured by Ajinomoto Fine-Techno Co., Ltd.), EFKA (manufactured by BASF), DISPERBYK (manufactured by BYK Chemical Co., Ltd.), BYKLPN (manufactured by BYK Chemical Co., Ltd.), DISPARLON (manufactured by Kusumoto Chemicals Co., Ltd.), SOLSPERSE (manufactured by Lubrizol), KP (manufactured by Shin-Etsu Chemical Co., Ltd.), POLYFLOW (manufactured by Kyoeisha Chemical Co., Ltd.), etc. These dispersants may be used alone or in combination of two or more in any combination and ratio.
[0095] The resin-based dispersant is generally contained in an amount of 30 to 60 parts, preferably 38 to 50 parts, based on 100 parts of the total mass of the organic pigments of the respective colors.
[0096] In the preparation of the coloring composition of the present invention, an organic solvent is generally used.
[0097] Examples of the organic solvent include diisopropyl ether, mineral spirits, n-pentane, amyl ether, ethyl octanoate, n-hexane, diethyl ether, isoprene, ethyl isobutyl ether, butyl stearate, n-octane, Varsol #2, APCO #18 solvent, diisobutylene, amyl acetate, butyl acetate, APCOTHINNER, butyl ether, diisobutyl ketone, methylcyclohexene, methyl nonyl ketone, propyl ether, dodecane, Socal Solvent No. 1 and No. 2, amyl formate, dihexyl ether, diisopropyl ketone, Solvesso #150, (n-, sec-, tert-) butyl acetate, hexene, SHELL TS28 solvent, butyl chloride, ethyl amyl ketone, ethyl benzoate, amyl chloride, ethylene glycol diethyl ether, ethyl orthoformate, methoxymethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl isobutyrate, benzonitrile, ethyl propionate, methyl cellosolve acetate, methyl isoamyl ketone, n-amyl methyl ketone (2-heptanone), methyl isobutyl ketone, propyl acetate, amyl acetate, amyl formate, dicyclohexane, diethylene glycol monoethyl ether acetate, dipentene, methoxymethyl amyl alcohol, methyl amyl ketone, methyl isopropyl ketone, propyl propionate, propylene glycol-tert-butyl ether, methyl ethyl ketone, methyl cellosolve, ethyl cellosolve, ethyl cellosolve acetate, carbitol, cyclohexanone, ethyl acetate, propylene glycol , propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether, propylene glycol monoethyl ether acetate, dipropylene glycol monoethyl ether, dipropylene glycol dimethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monomethyl ether acetate, 3-methoxypropionic acid, 3-ethoxypropionic acid, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, butyl 3-methoxypropionate, diethylene glycol dimethyl ether, ethylene glycol acetate, ethyl carbitol, butyl carbitol, ethylene glycol monobutyl ether, propylene glycol-tert-butyl ether, 3-methoxybutanol, 3-methyl-3-methoxybutanol, tripropylene glycol methyl ether.
[0098] When a photosensitive composition for forming a black matrix is prepared by photolithography using the coloring composition, it is preferred to use at least propylene glycol monomethyl ether acetate as an organic solvent contained in the coloring composition in order to obtain a composition with low viscosity and excellent coating, handling and ejection properties.
[0099] In order to prepare the coloring composition, the organic solvent may be used alone or in any combination and ratio. However, in the coloring composition of the present invention, the organic solvent is usually used in an amount of 300 to 800 parts, preferably 400 to 600 parts, relative to 100 parts of the total mass of the organic pigments of each color.
[0100] When preparing the coloring composition, various pigment derivatives can be used in combination as needed. Examples of substituents of the pigment derivatives include groups that are directly or via an alkyl group, an aryl group, a heterocyclic group, or the like, and are bonded to the pigment skeleton, such as a sulfonic acid group, a sulfonamide group, and a quaternary salt thereof, a phthalimidomethyl group, a dialkylaminoalkyl group, a hydroxyl group, a carboxyl group, and an amide group.
[0101] The coloring composition can be prepared by stirring and mixing the above-mentioned organic pigment composition of each color, the resinous dispersant and the organic solvent. If necessary, it can also be prepared by the following process: in the presence of various pulverizing media such as beads and rods, shaking for a necessary time, filtering the medium, etc., so as to disperse it.
[0102] The colored composition of the present invention can be used to form a black matrix portion by a conventionally known method.
[0103] The representative manufacturing method of the color filter is photolithography, and the black matrix uses the following method: the photosensitive composition described later prepared by the coloring composition of the present invention is applied to the transparent substrate for the color filter, and after heating and drying (pre-baking), ultraviolet rays are irradiated through a photomask to perform pattern exposure, and the photocurable compound of the portion corresponding to the black matrix portion is cured, and the unexposed portion is developed using a developer, and the non-pixel portion is removed and the pixel portion is fixed to the transparent substrate. By this method, a black matrix portion formed by a cured colored film of a photosensitive composition is formed on a transparent substrate. Each pixel portion of RGB can also be prepared by a photosensitive composition prepared by an organic pigment of each color with a larger specific surface area, as described above.
[0104] Examples of a method for applying the photosensitive composition described below onto a transparent substrate such as glass include a spin coating method, a roll coating method, a slit coating method, and an ink jet method.
[0105] The drying conditions of the coating film of the photosensitive composition applied to the transparent substrate vary depending on the type and proportion of each component, and are generally 50 to 150° C. and about 1 to 15 minutes. This heating treatment is generally referred to as “pre-baking”. In addition, as the light used in the photocuring of the photosensitive composition, ultraviolet light or visible light in the wavelength range of 200 to 500 nm is preferably used. Various light sources that emit light in this wavelength range can be used.
[0106] As a developing method, for example, a liquid method, an immersion method, a spray method, etc. can be cited. After the exposure and development of the photosensitive composition, the transparent substrate formed with the black matrix or the pixel portion of the desired color is washed with water and dried. For the color filter obtained in this way, a heating device such as a hot plate or an oven is used to perform a heating treatment (post-baking) at 100 to 280° C. for a predetermined time, thereby removing the volatile components in the colored coating film and thermally curing the unreacted photocurable compound remaining in the cured colored film of the photosensitive composition to complete the color filter.
[0107] The photosensitive composition for forming the black matrix portion of the color filter can be prepared by mixing the coloring composition of the present invention, an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator as essential components.
[0108] When the colored resin film forming the black matrix portion is required to be strong enough to withstand baking and the like performed in the actual production of the color filter, when preparing the above-mentioned photosensitive composition, not only a photopolymerizable monomer but also the alkali-soluble resin must be used in combination. When the alkali-soluble resin is used in combination, it is preferred to use an organic solvent that dissolves the alkali-soluble resin as the organic solvent.
[0109] The method for producing the photosensitive composition is generally a method in which the coloring composition of the present invention is prepared in advance, and then an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator are added thereto to prepare a photosensitive composition.
[0110] As the alkali-soluble resin used in the preparation of the photosensitive composition, there can be mentioned resins containing carboxyl groups or acidic hydroxyl groups, such as novolac-type phenolic resins, (meth) acrylate alkyl (meth) acrylic acid copolymers, styrene (meth) acrylic acid copolymers, styrene-maleic acid copolymers, etc. It should be noted that in the present invention, the description of (meth) acrylic acid is a general term for acrylic acid and methacrylic acid. Among them, in order to further improve the heat resistance of the cured film, it is preferred to use an alkali-soluble resin containing each polymerization unit of an imide structure, styrene, and (meth) acrylic acid.
[0111] Although the alkali-soluble resin does not have the above-mentioned function of combining the organic pigment with the anchoring part and extending the compatible part in the dispersion medium to form a dispersion, on the other hand, it is mainly used for the purpose of removing the unexposed part of the photosensitive composition by utilizing the characteristic of being dissolved by contact with an alkali.
[0112] As the photopolymerizable monomer, for example, there can be mentioned bifunctional monomers such as 1,6-hexanediol di(meth)acrylate, ethylene glycol di(meth)acrylate, neopentyl glycol di(meth)acrylate, triethylene glycol di(meth)acrylate, bis[(meth)acryloyloxyethoxy]bisphenol A, and 3-methylpentanediol di(meth)acrylate; polyfunctional monomers with relatively small molecular weights such as trimethylolpropane tri(meth)acrylate, pentaerythritol tri(meth)acrylate, tri(2-hydroxyethyl)isocyanurate tri(meth)acrylate, dipentaerythritol hexa(meth)acrylate, dipentaerythritol penta(meth)acrylate, and ditrimethylolpropane tetra(meth)acrylate; and polyfunctional monomers with relatively large molecular weights such as polyester acrylate, polyurethane acrylate, and polyether acrylate. As described above, the description of (meth)acrylate is a general term for combining acrylate and methacrylate.
[0113] Among these, in order to further improve the heat resistance of the cured film, it is preferred to use a tetrafunctional to hexafunctional (meth)acrylate.
[0114] Examples of the photopolymerization initiator include acetophenone, benzophenone, benzyl dimethyl ketal, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis(4'-azidobenzylidene)-2-propane, 1,3-bis(4-azidobenzylidene)-2-propane-2'-sulfonic acid, 4,4'-bisazidostilbene-2,2'-disulfonic acid, ethyl ketone, and 1-[9-ethyl-6-[2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzoyl]-9.H.-carbazole-3-yl]-1-(O-acetoxime).
[0115] By selecting an alkali-soluble resin and a photopolymerizable monomer that have no effect on transmittance, the cured film of the photosensitive composition can be set to have a maximum transmittance of less than 1% in the wavelength range of 400 to 800 nm suitable for the black matrix and a transmittance of 80% in the near-infrared region of 800 to 1100 nm.
[0116] The light transmittance of the black matrix refers to the light transmittance measured by a spectrophotometer for a black matrix (cured film) having a thickness of 3 μm formed on a transparent substrate such as a glass substrate, using the substrate without a resin black matrix formed thereon as a control.
[0117] The maximum transmittance refers to the maximum value of the transmittance in a specific wavelength region (range). More specifically, it is the maximum value of the transmittance curve in a specific wavelength region. For example, "the maximum transmittance in the wavelength range of 400nm to 800nm is less than 1%" means that the maximum value of the transmittance curve in the wavelength range of 400nm to 800nm is less than 1%, and there is no region in this range where the transmittance exceeds 1%.
[0118] On the other hand, "wavelength 800nm ~ 1100nm" refers to the so-called near-infrared region. "Black matrix with a transmittance of more than 80% in the near-infrared region with a wavelength of 800nm ~ 1100nm" refers to a black matrix with low light absorption and high transmittance in the long near-infrared region. The greater the transmittance in the near-infrared region, the easier it is for the black matrix to dissipate the heat in the TFT element, which is a heat source. Therefore, the increase in the on (ON) current and the off (OFF) current in the TFT element is also small, and it is difficult to cause thermal runaway.
[0119] In addition, if the volume resistivity is 1×10 13 When the dielectric constant is greater than Ω·cm and less than 5, short circuits of TFT elements (switching elements composed of thin film transistors) caused by leakage current can be reduced, switching of TFT elements can be accurately transmitted, and disturbances in driving of liquid crystals can be reduced.
[0120] Volume resistivity is a measure of the insulating properties of a substance and is the resistance per unit volume. Volume resistivity can be measured, for example, by the method described in "Electrical Society of Japan University Lectures on Electrical and Electronic Materials - Fundamentals to Test Methods" (Ohm Co., Ltd., 2006, pp. 223-230) of the Electrical Society of Japan.
[0121] The dielectric constant is the so-called relative dielectric constant, which is the ratio of the dielectric constant of a substance to the dielectric constant of a vacuum. The dielectric constant can be measured by the method described in, for example, "Electrical Society University Lectures on Electrical and Electronic Materials - Fundamentals to Test Methods" (Ohm Co., Ltd., 2006, pp. 233-243) of the Electrical Society of Japan.
[0122] The photosensitive composition of the present invention having such characteristics can be prepared by adding 3 to 20 parts of an alkali-soluble resin and a photopolymerizable monomer in total to 100 parts of the coloring composition of the present invention, and 0.05 to 3 parts of a photopolymerization initiator to 1 part of the photopolymerizable monomer, and further adding an organic solvent used in the preparation of the above-mentioned coloring composition as needed, stirring and dispersing the mixture to make it uniform, thereby obtaining a photosensitive composition for forming a black matrix portion.
[0123] When a black matrix is formed by photolithography, the photosensitive composition of the present invention is preferably prepared so that the nonvolatile content is at least 5 to 20% by mass in order to have a low viscosity and excellent coating and handling properties.
[0124] As a developer, a well-known and commonly used alkaline aqueous solution can be used. In particular, since the photosensitive composition contains an alkali-soluble resin, washing with an alkaline aqueous solution is effective for the formation of the black matrix portion. The excellent heat resistance of the photosensitive composition of the present invention is brought into play in the color filter manufacturing method in which the alkali cleaning is followed by firing.
[0125] In the pigment dispersion method, the method for manufacturing the black matrix portion using the photolithography method is described in detail, but the black matrix portion prepared using the photosensitive composition of the present invention can also be formed using other methods such as electrodeposition, transfer, micelle electrolysis, PVED (Photovoltaic Electrodeposition) method, etc., to manufacture a color filter.
[0126] The color filter can be obtained by the following method: using a red organic pigment, a green organic pigment, a blue organic pigment and a photosensitive composition of each color obtained by using the coloring composition of the present invention, a liquid crystal material is sealed between a pair of parallel transparent electrodes, the transparent electrodes are divided into discontinuous fine intervals, and color filter color pixel portions of any color selected from red (R), green (G) and blue (B) are alternately arranged in a pattern in the fine intervals divided into a grid shape by a black matrix on the transparent electrode; or after forming the color filter color pixel portion on the substrate, a transparent electrode is arranged.
[0127] The black matrix portion obtained from the photosensitive composition of the present invention contains the above-mentioned blue, yellow, and red organic pigments in a black color. At first glance, it seems that the same black matrix as the case of preparing a black photosensitive composition by mixing the photosensitive compositions of the respective colors can be obtained. However, in the present invention, the organic pigments of the respective colors are mixed in advance when preparing the coloring composition as a stage before preparing the photosensitive composition. As a result, more uniform mixing can be achieved, and a black matrix with more excellent characteristics can be obtained.
[0128] In the coloring composition of the present invention, the sulfonate compound is preferably such that the pH of the sulfonate compound aqueous solution obtained by mixing 0.5 parts of the sulfonate compound represented by formula (1) with 10 parts of pure water having a pH of 6 to 8 is 2 to 12, and the maximum absorbance in the wavelength region of 380 to 780 nm measured in accordance with JIS K0115: 2004 is 10% or less of the maximum absorbance of PV29. In addition, from the viewpoint of obtaining a particularly low-viscosity dispersion, the pH of the sulfonate compound aqueous solution is preferably 6 to 11.
[0129] The pH of the aqueous solution of the sulfonate compound can be measured using a pH meter in accordance with JIS Z 8802: 2011. The maximum absorbance in the wavelength region of 380 to 780 nm is a relative value obtained by measuring an absorbance spectrum using a spectrophotometer in accordance with JIS K 0115: 2004, with the absorbance of the peak of the absorbance spectrum of an aqueous solution obtained by mixing 0.5 parts of CI Pigment Violet 29 and 10 parts of pure water being taken as 100.
[0130] The acidity of the pigment can be measured as follows: about 0.1g of the sample is mixed with 0.001N tetrabutylammonium hydroxide (TBAH) / n-propyl acetate (NPAC) solution (or 15ml of 0.001N p-toluenesulfonic acid (PTSA) / NPAC solution) using a rotary and revolving mixer, and the pigment is precipitated by centrifugation, and the non-adsorbed acid and alkali amount in 10ml of the supernatant is measured by potentiometric titration using 0.001N PTSA / NPAC (or TBAH / NPAC solution). In addition, the amount of pigment adsorption can be calculated by subtracting the above-mentioned non-adsorbed amount from the amount added. In addition, the value obtained by dividing the alkali adsorption amount by the acid adsorption amount is used as the colorant acid-base adsorption amount ratio, and the larger the value, the higher the acidity is judged.
[0131] The dispersion containing the coloring composition of the present invention is obtained by adding PV29 and the sulfonate compound represented by formula (1) as essential components, adding an organic solvent such as propylene glycol monomethyl ether acetate, a dispersant such as an alkaline resin type dispersant, adding zirconium oxide beads, and dispersing using a paint conditioner. The viscosity of the dispersion is, for example, 1 to 100 mPa·s, preferably 3 to 20 mPa·s. The viscosity of the dispersion can be measured using an E-type viscometer.
[0132] The cured coating film of the color filter can be prepared by mixing the above-mentioned dispersion, alkali-soluble resin, photopolymerizable monomer, photopolymerization initiator and organic solvent to prepare a photosensitive resin composition, and then preparing the composition according to a conventional method for preparing a black matrix.
[0133] Example
[0134] Hereinafter, the present invention will be described in more detail based on Examples, but the present invention is not limited to the following Examples. In the present Examples, "parts" means "parts by mass".
[0135] [Example 1]
[0136] <Process for preparing coloring composition>
[0137] Paliogen Red Violet K 5411 (manufactured by BASF Corporation, CI Pigment Violet 29, colorant) 17 parts, BYK LPN-21116 (manufactured by BYK-Chemie Co., Ltd., basic acrylic resin type dispersant) 44 parts, sodium 2-naphthalenesulfonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., additive) 2 parts, propylene glycol monomethyl ether acetate (manufactured by Kuraray Trading Co., Ltd., organic solvent) 218 parts were mixed, 0.2 to 0.3 mmφ zirconium oxide beads were added, and dispersed for 2 hours using a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) to obtain a coloring composition (A-1).
[0138] <Photosensitive resin composition preparation process>
[0139] 100 parts of the coloring composition (A-1), 5 parts of a methacrylic acid / mono(2-methacryloyloxyethyl) succinate / N-phenylmaleimide / styrene / benzyl methacrylate copolymer (copolymerization mass ratio = 25 / 10 / 30 / 20 / 15, Mw = 12,000, Mn = 6,500) as an alkali-soluble resin, 10 parts of dipentaerythritol hexaacrylate as a photopolymerizable monomer, and 10 parts of a photopolymerization initiator. A photosensitive resin composition (B-1) was prepared by mixing 1 part of ethyl ketone, 1-[9-ethyl-6-[2-methyl-4-(2,2-dimethyl-1,3-dioxolanyl)methoxybenzoyl]-9.H.-carbazole-3-yl]-1-(O-acetoxime), and 25 parts of dipropylene glycol dimethyl ether, 25 parts of propylene glycol monomethyl ether acetate, 75 parts of 3-methoxybutyl acetate, and 50 parts of cyclohexanone as an organic solvent.
[0140] <Process for producing a curing pattern>
[0141] A 10 cm square glass substrate (glass plate "OA-10" for color filters manufactured by Nippon Electric Glass Co., Ltd.) was immersed in a 1% diluted solution of silane coupling agent "KBM-603" manufactured by Shin-Etsu Chemical for 3 minutes, washed with water for 10 seconds, and dried in an oven at 110°C for 5 minutes after removing moisture with an air gun. The photosensitive resin composition (B-1) prepared above was applied to the glass substrate using a spin coater. After vacuum drying for 1 minute, the mixture was heated and dried at 90°C on a hot plate for 90 seconds to obtain a coating film with a dry film thickness of approximately 3.5 μm. Then, the image was exposed from the coating film side through a 15 μm wide fine line pattern mask. The exposure conditions were set to use a 3kW high-pressure mercury lamp at 50 mJ / cm 2(i-ray reference). Next, a developer consisting of an aqueous solution containing 0.05% potassium hydroxide and 0.08% nonionic surfactant (Kao "A-60") was used to perform spray development at a water pressure of 0.15 MPa at 23°C, and then development was stopped with pure water, and the surface was washed with a water spray to obtain a cured pattern (C-1). It should be noted that the spray development time was adjusted between 10 and 120 seconds, which was 1.5 times the time for the unexposed coating film to be dissolved and removed.
[0142] <pH and absorbance of additives>
[0143] 0.5 parts of the additive and 10 parts of pure water (2 μS / cm or less and pH: 7.0±1.0) were mixed. The pH was measured using a pH meter (PH71, manufactured by Yokogawa Electric Corporation) in accordance with JIS Z8802:2011. The absorption spectrum of the aqueous solution in the wavelength region of 380 to 780 nm was measured using a spectrophotometer (U3900, manufactured by Hitachi High-Technologies Corporation) in accordance with JIS K 0115:2004, and the absorbance at the peak of the absorption spectrum of a dispersion solution mixed with 0.5 parts of Paliogen Red Violet K 5411 (CI Pigment Violet 29, manufactured by BASF Corporation, colorant) and 10 parts of pure water (2 μS / cm or less and pH: 7.0±1.0) was set to 100, and the absorbance is recorded in the following Table 1.
[0144] [Example 2]
[0145] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium p-toluenesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-2). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-2) to obtain a cured pattern (C-2).
[0146] [Example 3]
[0147] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium allyl sulfonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., additive) to obtain a colored composition (A-3). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-3) to obtain a cured pattern (C-3).
[0148] [Example 4]
[0149] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of potassium methanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-4). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-4) to obtain a cured pattern (C-4).
[0150] [Example 5]
[0151] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium 2-morpholinoethanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-5). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-5) to obtain a cured pattern (C-5).
[0152] [Example 6]
[0153] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium 3-mercapto-1-propanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-6). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-6) to obtain a cured pattern (C-6).
[0154] [Example 7]
[0155] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium (±)-10-camphorsulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-7). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-7) to obtain a cured pattern (C-7).
[0156] [Example 8]
[0157] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium 1-decanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-8). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-8) to obtain a cured pattern (C-8).
[0158] [Example 9]
[0159] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of sodium anthraquinone-2-sulfonate monohydrate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-9). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-9) to obtain a cured pattern (C-9).
[0160] [Example 10]
[0161] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of disodium anthraquinone-2,6-disulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-10). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-10) to obtain a cured pattern (C-10).
[0162] [Comparative Example 1]
[0163] The same operation as in Example 1 was performed except that the additives of Example 1 were not added to obtain a colored composition (A-11). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-11) to obtain a cured pattern (C-11).
[0164] [Comparative Example 2]
[0165] The same operation as in Example 1 was performed except that the coloring agent in Example 1 was changed to 17 parts of PALIOGEN RED L3880 HD (manufactured by BASF Corporation, CI Pigment Red 178, coloring agent) and no additives were added, thereby obtaining a coloring composition (A-12). The same operation as in Example 1 was performed except that the coloring composition (A-1) was changed to the coloring composition (A-12), thereby obtaining a cured pattern (C-12).
[0166] [Comparative Example 3]
[0167] The same operation as in Example 1 was performed except that the coloring agent in Example 1 was changed to 17 parts of 229-6438 (manufactured by SUN CHEMICAL Co., Ltd., CI Pigment Red 179, coloring agent) and no additives were added to obtain coloring compositions (A to 13). The same operation as in Example 1 was performed except that the coloring composition (A-1) was changed to the coloring composition (A-13) to obtain a cured pattern (C-13).
[0168] [Comparative Example 4]
[0169] The same operation as in Example 1 was performed except that the coloring agent in Example 1 was changed to 17 parts of PALIOGEN RED L3880 HD (manufactured by BASF Corporation, CI Pigment Red 178, coloring agent) to obtain a coloring composition (A-14). The same operation as in Example 1 was performed except that the coloring composition (A-1) was changed to the coloring composition (A-14) to obtain a cured pattern (C-14).
[0170] The same operation as in Example 1 was performed except that the coloring agent in Example 1 was changed to 17 parts of 229-6438 (manufactured by Taiyo Chemical Co., Ltd., CI Pigment Red 179, coloring agent) to obtain a coloring composition (A-15). The same operation as in Example 1 was performed except that the coloring composition (A-1) was changed to the coloring composition (A-15) to obtain a cured pattern (C-15).
[0171] [Comparative Example 6]
[0172] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of 2-naphthalenesulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain a colored composition (A-16). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-16) to obtain a cured pattern (C-16).
[0173] [Comparative Example 7]
[0174] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of p-toluenesulfonic acid monohydrate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., additive) to obtain a colored composition (A-17). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-17) to obtain a cured pattern (C-17).
[0175] [Comparative Example 8]
[0176] The same operation as in Example 1 was performed except that the additive in Example 1 was changed to 2 parts of SOLSPERSE 12000 (manufactured by Lubrizol Corporation, additive) to obtain a colored composition (A-18). The same operation as in Example 1 was performed except that the colored composition (A-1) was changed to the colored composition (A-18) to obtain a cured pattern (C-18).
[0177] <Evaluation>
[0178] Acidity of the pigment (acid-base adsorption ratio)
[0179] About 0.1 g of the pigment was mixed with 15 ml of a 0.001N tetrabutylammonium hydroxide (TBAH) / n-propyl acetate (NPAC) solution or a 0.001N p-toluenesulfonic acid (PTSA) / NPAC solution using a rotary revolution mixer (degassing mixer (Awatori Rentaro), manufactured by Thinky Co., Ltd.) for 3 minutes, and then the pigment was precipitated by centrifugation (11,000 rpm, 20 minutes), and the amount of unadsorbed acid and alkali in 10 ml of the supernatant was measured by potentiometric titration using 0.001N PTSA / NPAC or TBAH / NPAC solution (COM-1700, manufactured by Hiranuma Sangyo Co., Ltd.). The amount of acid and alkali adsorbed on the pigment was calculated by subtracting the above-mentioned unadsorbed amount from the added amount. The value obtained by dividing the amount of base adsorption by the amount of acid adsorption was taken as the colorant acid-base adsorption ratio, and the larger the value, the higher the acidity. It was confirmed that PV29 has a much higher acidity than CI Pigment Red 178 (PR178) and CI Pigment Red 179 (PR179), which are also perylene.
[0180] Viscosity
[0181] As the viscosity of the colored compositions (A-1) to (A-18) obtained in Examples 1 to 10 and Comparative Examples 1 to 8, the values at 30 rpm were measured using an E-type viscometer (TVE-25L, manufactured by Toki Sangyo Co., Ltd.). In the viscosity system 1 using PV29 as a colorant, the value of Comparative Example 1 was converted to 100 and is described in the following table. In the viscosity system 2 using PR178 as a colorant, the value of Comparative Example 2 was converted to 100 and is described in the following Table 1. In the viscosity system 3 using PR179 as a colorant, the value of Comparative Example 3 was converted to 100 and is described in the following Table 1.
[0182] ·Cure degree
[0183] The presence or absence of pattern defects in the cured patterns (C-1) to (C-10), (C-11), (C-16) to (C-18) obtained in Examples 1 to 10, Comparative Example 1, and Comparative Examples 6 to 8 was visually confirmed (the degree of cure was "○" for those without defects and "×" for those with defects), and the results were recorded as the degree of cure in the following Table 1.
[0184] Spectral purity
[0185] The absorption spectra of the cured patterns (C-1) to (C-10), (C-11) and (C-16) to (C-18) obtained in Examples 1 to 10, Comparative Example 1 and Comparative Examples 6 to 8 were measured using a spectrophotometer (U3900, manufactured by Hitachi High-Technologies Corporation). The case where the absorbance of the peak of the absorption spectrum in the wavelength region of 380 to 780 nm showed an absorption peak other than PV29 with an intensity of 3% or more was recorded as "0", and the case where it was recorded as "×" was recorded in the following Table 1.
[0186] [Table 1]
[0187]
[0188] ※S12000; SOLSPERSE 12000 (copper phthalocyanine sulfonic acid; manufactured by Lubrizol Corporation)
[0189] Examples 1 to 10, which combine PV29 and a non-pigment sulfonate with a pH of 2 to 12 when preparing an aqueous solution, can obtain a dispersion with a low viscosity compared to Comparative Example 1 in which no additive is added and Comparative Example 8, which combines PV29 and a sulfonic acid derivative of a pigment such as copper phthalocyanine sulfonic acid. In addition, by comparing Example 1 with Comparative Example 1, Comparative Example 2 with Comparative Example 4, and Comparative Example 3 with Comparative Example 5, it can be seen that Example 1 has a greater effect of reducing the viscosity when a sulfonate is added than Comparative Examples 4 and 5, which combine perylene other than PV29 and a sulfonic acid. In addition, it can be seen that Examples 1 to 10, which add a non-pigment sulfonic acid derivative, can maintain the degree of curing and spectral purity even after the derivative is added, compared to Comparative Example 8, which combines a sulfonic acid derivative of a pigment such as copper phthalocyanine sulfonic acid.
Claims
1. A coloring composition comprising a sulfonate compound and CI Pigment Violet 29, wherein the sulfonate compound is at least one sulfonate compound selected from the group consisting of benzenesulfonate, toluenesulfonate, naphthalenesulfonate, anthraquinonesulfonate, 2-morpholinoalkylsulfonate, allylsulfonate, (±)-10-camphorsulfonate, linear alkylsulfonate, and branched alkylsulfonate. 2 . The coloring composition according to claim 1 , wherein the ratio of the sulfonate compound is 0.5 to 20 parts by mass relative to 100 parts by mass of CI Pigment Violet 29. 3 .
3. The coloring composition according to claim 1 or 2, wherein the sulfonate compound is at least one compound selected from the group consisting of compounds represented by the following formulas (1-1) to (1-10), sodium 2-naphthalenesulfonate, sodium 2-morpholinoethanesulfonate, sodium p-toluenesulfonate, potassium methanesulfonate, sodium 3-mercapto-1-propanesulfonate, sodium allylsulfonate, sodium (±)-10-camphorsulfonate, and sodium 1-decanesulfonate. [Chemistry 1] [Chemistry 2] [Chemistry 3] [Chemistry 4] [Chemistry 5] [Chemistry 6] [Chemistry 7] [Chemistry 8] [Chemistry 9] [Chemistry 10] 4 . A color filter comprising the colored composition according to claim 1 .
Citation Information
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