WO2022034734A1 - 着色組成物、及びカラーフィルタ - Google Patents
着色組成物、及びカラーフィルタ Download PDFInfo
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- WO2022034734A1 WO2022034734A1 PCT/JP2021/022016 JP2021022016W WO2022034734A1 WO 2022034734 A1 WO2022034734 A1 WO 2022034734A1 JP 2021022016 W JP2021022016 W JP 2021022016W WO 2022034734 A1 WO2022034734 A1 WO 2022034734A1
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- sulfonate
- coloring composition
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- pigment
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- 0 *c(cc1C(c2c3cccc2)=O)ccc1C3=O Chemical compound *c(cc1C(c2c3cccc2)=O)ccc1C3=O 0.000 description 4
- BSKZYRZYPPSCRL-UHFFFAOYSA-N Oc(cccc1C(c(c2ccc3)c3N=O)=O)c1C2=O Chemical compound Oc(cccc1C(c(c2ccc3)c3N=O)=O)c1C2=O BSKZYRZYPPSCRL-UHFFFAOYSA-N 0.000 description 2
- JNSMGBRALXTWND-UHFFFAOYSA-N [O-][N+]1(C(C2)C(N=O)=CC(C(c3c4cccc3)=O)=C2C4=O)[IH]C1 Chemical compound [O-][N+]1(C(C2)C(N=O)=CC(C(c3c4cccc3)=O)=C2C4=O)[IH]C1 JNSMGBRALXTWND-UHFFFAOYSA-N 0.000 description 2
- MVJRLHNKKOTUMG-UHFFFAOYSA-N C[NH+](c(cc1C(c(c2c3)ccc3N)=O)ccc1C2=O)[O-] Chemical compound C[NH+](c(cc1C(c(c2c3)ccc3N)=O)ccc1C2=O)[O-] MVJRLHNKKOTUMG-UHFFFAOYSA-N 0.000 description 1
- RCSMBBHQCLEWMO-UHFFFAOYSA-N O=C(c1ccccc11)c2cccc(N=O)c2C1=O Chemical compound O=C(c1ccccc11)c2cccc(N=O)c2C1=O RCSMBBHQCLEWMO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
- C09D17/003—Pigment pastes, e.g. for mixing in paints containing an organic pigment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/34—Heterocyclic compounds having nitrogen in the ring
- C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
- C08K5/3432—Six-membered rings
- C08K5/3437—Six-membered rings condensed with carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
- C08K5/42—Sulfonic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B5/00—Dyes with an anthracene nucleus condensed with one or more heterocyclic rings with or without carbocyclic rings
- C09B5/62—Cyclic imides or amidines of peri-dicarboxylic acids of the anthracene, benzanthrene, or perylene series
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/006—Preparation of organic pigments
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/08—Treatment with low-molecular-weight non-polymer organic compounds
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D17/00—Pigment pastes, e.g. for mixing in paints
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
- C08K2003/2244—Oxides; Hydroxides of metals of zirconium
Definitions
- the present invention relates to a coloring composition and a color filter.
- liquid crystal panels that have introduced a color filter-on-array (COA) that integrates a color filter substrate and a TFT array substrate are attracting attention. If COA is used, the precise alignment performed when the above two substrates are used becomes unnecessary, and the red, blue, and green pixels of the color filter can be miniaturized to the limit, so that the liquid crystal display can be used. High-definition panel is possible.
- COA color filter-on-array
- the coloring composition and dispersion liquid for producing the above-mentioned color filter are described in, for example, Patent Document 1-4 below.
- the combination of perylene and the sulfonic acid derivative of the dye has a high dispersion viscosity.
- the derivative is an organic dye derivative, the absorbance in the visible region is high, and the hue changes as compared with the colorant alone.
- Another problem is that the absorbance in the ultraviolet region is high, which hinders UV curing.
- adding a dye pigment derivative for the purpose of improving the dispersibility of a difficult-to-disperse dye pigment is a general-purpose method known in the industry, but a dye pigment derivative having high coloring power.
- a dye pigment derivative having high coloring power When the above is added, the decrease in the purity of the spectrum becomes a problem.
- dye pigments are required to have a higher level of dispersibility in color filter applications and display shading applications.
- an object of the present invention is to provide a coloring composition and a color filter that can solve the above-mentioned problems.
- C. I. Perylene other than Pigment Violet 29 is dispersed by a mechanism in which the highly acidic NH portion is replaced and the acidity is low, so that the matrix of the acidic derivative is adsorbed on perylene and the acidic group is adsorbed on the amine of the dispersant. Since the viscosity is lowered, the acid does not become excessive in the range of normal use (added about 1 to 20%).
- C.I. I. Pigment Violet 29 has a highly acidic imide moiety NH and acts directly with the dispersant amine. Therefore, when an acidic sulfonic acid derivative is added, the acid becomes excessive.
- the present invention is as follows.
- Item 1 The sulfonate compound represented by the following formula (1) and C.I.
- I. A coloring composition comprising Pigment Violet 29.
- A-SO 3 M ⁇ nH 2 O formula (1) [A in the formula (1) is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus and oxygen in the structure, and M is 1 excluding H. 1 equivalent of a ⁇ trivalent cation, where n is an integer of 0-5]
- Item 2 The sulfonate compound represented by the following formula (1) and C.I.
- a coloring composition comprising Pigment Violet 29.
- a in the formula (1) is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus and oxygen in the structure, and M is 1 excluding H. 1 equivalent of a ⁇ trivalent cation,
- the pH of the aqueous sulfonate compound solution obtained by mixing 0.5 part of the sulfonate compound represented by the following formula (1) with 10 parts of pure water having a pH of 6 to 8 is 2 to 12, and JIS K 0115:
- the maximum absorbance in the wavelength range of 380 to 780 nm measured according to 2004 is C.I. I. Item 2.
- A-SO 3 M ⁇ nH 2 O formula (1) [A in the formula (1) is a hydrocarbon group having 1 to 20 carbon atoms which may have halogen, boron, nitrogen, sulfur, phosphorus and oxygen in the structure, and M is 1 excluding H. 1 equivalent of a ⁇ trivalent cation, where n is an integer of 0-5] Item 3.
- Item 2. The coloring composition according to Item 2, wherein the pH of the aqueous solution of the sulfonate compound is 6 to 11.
- the sulfonate compound represented by the formula (1) is a benzene sulfonate, a toluene sulfonate, a naphthalene sulfonate, an anthraquinone sulfonate, a 2-morpholinoalkyl sulfonate, an allyl sulfonate, ( ⁇ ). )-10-The coloring composition according to any one of Items 1 to 3, which is at least one sulfonate compound selected from a camphor sulfonate, a linear alkyl sulfonate, and a branched alkyl sulfonate. Item 5.
- the sulfonate compound represented by the above formula (1) is represented by the following formulas (1-1) to (1-10).
- Equation (1-1) Equation (1-2) Equation (1-3) Equation (1-4) Equation (1-5) Equation (1-6) Equation (1-7) Equation (1-8) Equation (1-9) Equation (1-10)
- the coloring composition according to any one of Items 1 to 4 which is at least one compound selected from the group consisting of ⁇ ) -10-sodium kanfer sulfonate and sodium 1-decane sulfonate.
- Item 6. A color filter containing the coloring composition according to any one of Items 1 to 5.
- the coloring composition of the present invention is C.I. I.
- C.I. I. By combining Pigment Violet 29 and a non-pigmented sulfonate, C.I. I.
- a dispersion having a particularly low viscosity can be obtained as compared with the combination of Pigment Violet 29 and the sulfonic acid derivative of the dye.
- C.I. I. Compared with a combination of perylene other than Pigment Violet 29 and a sulfonate, the effect of reducing the viscosity at the time of adding the sulfonate is large.
- the coloring composition of the present invention uses a non-dye-based sulfonate derivative having a small absorbance in the visible region, the change from the hue of the colorant alone is small even after the addition of the derivative. Moreover, since the absorbance in the ultraviolet region is small, it does not inhibit ultraviolet curing.
- Examples of the halogen that is A in the 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 chains having 1 to 12 carbon atoms. Examples include alkyl groups.
- the monovalent to trivalent cations excluding H, which is M include lithium, sodium, potassium, calcium, magnesium, titanium, chromium, aluminum, manganese, iron, copper, nickel, silver, gold, lead, and tin. Can be mentioned.
- the sulfonate compound represented by the above formula (1) is benzene sulfonate, toluene sulfonate, naphthalene sulfonate, anthraquinone sulfonate, 2-morpholinoalkyl sulfonate, allyl sulfonate, ( ⁇ ). ) -10-Camfer sulfonate, linear alkyl sulfonate, branched alkyl sulfonate, at least one sulfonate compound is preferred.
- these sulfonate compounds can prevent the increase in viscosity due to the entanglement of the dispersant molecules, and are particularly low viscosity dispersions. Can be.
- the sulfonate compound represented by the above formula (1) has the following formulas (1-1) to (1-10).
- Equation (1-1) Equation (1-2) Equation (1-3) Equation (1-4) Equation (1-5) Equation (1-6) Equation (1-7) Equation (1-8) Equation (1-9) Equation (1-10)
- the ratio of the sulfonate compound represented by the above formula (1) is, for example, 0.5 to 20 parts by mass, preferably 1 to 5 parts by mass with respect to 100 parts by mass of PV29. be.
- the coloring composition of the present invention may contain a perylene-based organic pigment other than PV29.
- a perylene-based organic pigment include C.I. I. Pigment Red 123, C.I. I. Pigment Red 149, C.I. I. Pigment Red 178, C.I. I. Pigment Red 179, C.I. I. Pigment Red 189, C.I. I. Pigment Red 190, C.I. I. Pigment Red 224, C.I. I. Pigment Red 228, C.I. I. Pigment Black 31, C.I. I. Pigment Black 32 and the like.
- organic pigments may be used in combination in order to have a light-shielding property.
- organic pigments include blue organic pigments, yellow organic pigments, and red organic pigments.
- organic pigments are azo-based, phthalocyanine-based, quinacridone-based, and benzimidazole based on the chemical structure.
- organic pigments such as lon-based, isoindolinone-based, dioxazine-based, indanslen-based, and perylene-based.
- specific examples of pigments that can be used in the present invention are shown by pigment numbers.
- Examples of the blue organic pigment include C.I. I. 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, 80, etc. Can be mentioned. Among these, preferably C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 25, 26, 60, 80, more preferably C.I. I. Pigment Blue 15: 6, 25, 26, 60, 80 can be mentioned.
- Examples of the yellow organic pigment include C.I. I. 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,
- C.I. I. Pigment Yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, 185, 229 and more preferably C.I. I. Pigment Yellow 83, 138, 139, 150, 180, 185, 229 can be mentioned.
- red organic pigment examples include C.I. I. 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: 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, 149, 151, 166, 168, 169, 170, 172, 173, 174, 175, 176, 177, 178, 179, 181, 184, 185, 187, 188, 190, 193, 194,
- C.I. I. Pigment Red 48 1, 122, 168, 177, 202, 206, 207, 209, 224, 242, 254, more preferably C.I. I. Pigment Red 177, 209, 224, 254 can be mentioned.
- 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 is preferably 20 to 100 nm in order to impart high light-shielding properties. If the primary particle diameter of the pigment exceeds 150 nm, the dispersion stability deteriorates, and as a result, light scattering may easily occur.
- the primary particle size of the pigment in the coloring composition of the present invention means that the coloring composition is dispersed in a solvent such as cyclohexanone, the dispersion is applied on a colloidal film, and an image of a scanning electron microscope (TEM) is taken. .. The size of 1000 particles of the obtained photographed image was measured, and the average value was taken as the primary particle diameter of the pigment.
- a solvent such as cyclohexanone
- the fineness of the pigment is roughly classified by a pulverization method such as dry pulverization and wet pulverization.
- a pulverization method such as dry pulverization and wet pulverization.
- the solvent salt is kneaded for a long time with a high inorganic salt ratio to the pigment. Milling is preferred.
- a green organic pigment, a purple organic pigment, an orange organic pigment, a brown organic pigment, or the like may be used in combination to adjust the color tone.
- the other-color organic pigment used in combination with these it is preferable to use one having an average primary particle size of 20 to 100 nm.
- organic pigments having colors other than blue, yellow, and red examples include C.I. I. Pigment Green 7, 36, 58, 62, 63, C.I. I. Pigment Orange 13, 36, 38, 60, 62, 64, 71, 72, C.I. I. Pigment Violet 19, 23, 37 and the like can be mentioned.
- the organic pigments used and their combinations may be as long as the blackness required for the target black matrix can be obtained.
- Making black by subtractive mixing of the three primary colors of blue, yellow, and red belongs to the common general knowledge of those skilled in the art, and the mixing ratio thereof is not particularly limited.
- each color can be used in combination by increasing or decreasing by plus or minus 7%, centering on 33% of each color on a mass basis. The black color can be adjusted.
- a resin-based dispersant When these organic pigment compositions are dispersed in an organic solvent, a resin-based dispersant may be used in order to improve dispersibility and dispersion stability.
- This resin-based dispersant has a function of binding to an organic pigment and an anchor portion and extending a compatible portion to a dispersion medium to form a dispersion, and is an alkali used for preparing a photosensitive composition described later.
- Soluble resins and photopolymerizable monomers are different types.
- resin-based dispersants include Ajinomoto Fine-Techno (Ajinomoto Fine-Techno), EFKA (BASF), DISPERBYK (Big Chemie), BYKLPN (Big Chemy), and Disparon (Kusumoto Kasei). , SOLPERSE (manufactured by Lubrizol), KP (manufactured by Shin-Etsu Chemical Co., Ltd.), Polyflow (manufactured by Kyoei Co., Ltd.) and the like.
- One of these dispersants may be used, and two or more of these dispersants may be used in any combination and ratio.
- the resin-based dispersant is usually 30 to 60 parts, preferably 38 to 50 parts, per 100 parts by mass of the total organic pigments of each color.
- An organic solvent is usually used for preparing the coloring composition of the present invention.
- the organic solvent include diisopropyl ether, mineral spirit, n-pentane, amyl ether, ethyl caprilate, n-hexane, diethyl ether, isoprene, ethyl isobutyl ether, butyl stearate, n-octane, valsol # 2, and apco.
- a photosensitive composition for forming a black matrix by a photolithography method using a coloring composition in order to obtain a low viscosity and excellent coatability, workability, and ejection property. At least, it is preferable to use propylene glycol monomethyl ether acetate as the organic solvent contained in the coloring composition.
- one organic solvent may be used alone, or two or more of them may be used in any combination and ratio.
- the coloring composition can be prepared by stirring and mixing the organic pigment composition of each color, the resin-based dispersant and the organic solvent described above. If necessary, it can be prepared by shaking for a required time in the presence of various crushed media such as beads and rods, and dispersing the media by filtration or the like.
- the coloring composition of the present invention can be used for forming a black matrix portion by a conventionally known method.
- a typical manufacturing method of a color filter is a photolithography method, and in a black matrix, a photosensitive composition described later prepared from the coloring composition of the present invention is applied onto a transparent substrate for a color filter and heated. After drying (pre-baking), pattern exposure is performed by irradiating ultraviolet rays through a photo mask to cure the photocurable compound at the portion corresponding to the black matrix portion, and then the unexposed portion is developed with a developing solution. This is a method of removing the non-pixel portion and fixing the pixel portion to the transparent substrate. By this method, a black matrix portion made of a cured colored film of the photosensitive composition is formed on the transparent substrate.
- Each pixel portion of RGB can also be similarly prepared as described above from a photosensitive composition prepared from an organic pigment of each color having a larger specific surface area.
- the drying conditions of the coating film of the photosensitive composition applied to the transparent substrate vary depending on the type of each component, the mixing ratio, etc., but are usually about 1 to 15 minutes at 50 to 150 ° C. This heat treatment is generally called "pre-bake”.
- pre-bake the heat treatment
- the light used for photocuring the photosensitive composition it is preferable to use ultraviolet rays in the wavelength range of 200 to 500 nm or visible light. Various light sources that emit light in this wavelength range can be used.
- Examples of the developing method include a liquid filling method, a dipping method, and a spraying method.
- the transparent substrate on which the black matrix or the pixel portion of the required color is formed is washed with water and dried.
- the color filter thus obtained is heat-treated (post-baked) at 100 to 280 ° C. for a predetermined time by a heating device such as a hot plate or an oven to remove volatile components in the colored coating film and at the same time to be photosensitive.
- the unreacted photocurable compound remaining in the cured colored film of the sex composition is thermally cured to complete the color filter.
- the photosensitive composition for forming the black matrix portion of the color filter contains the coloring composition of the present invention, an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator as essential components, and mixes them. It can be prepared by
- the colored resin film forming the black matrix portion is required to have toughness or the like that can withstand the baking or the like performed in the actual production of the color filter, only the photopolymerizable monomer is used in preparing the photosensitive composition. However, it is indispensable to use this alkali-soluble resin together. When an alkali-soluble resin is used in combination, it is preferable to use a solvent that dissolves the organic solvent.
- the colored 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 the photosensitive composition.
- an alkali-soluble resin, a photopolymerizable monomer, and a photopolymerization initiator are added thereto to prepare the photosensitive composition.
- alkali-soluble resin used for preparing the photosensitive composition examples include a resin containing a carboxyl group or a hydroxyl group exhibiting acidity, for example, a novolak type phenol resin, a (meth) acrylic acid alkyl ester (meth) acrylic acid copolymer, and styrene.
- examples thereof include (meth) acrylic acid copolymers and styrene-maleic acid copolymers.
- the description of (meth) acrylic is a general term for acrylic and methacrylic.
- This alkali-soluble resin does not have the above-mentioned function of binding to the organic pigment and the anchor portion and extending the compatible portion to the dispersion medium to form a dispersion, but on the other hand, it is in contact with alkali. It is used exclusively for the purpose of removing the unexposed portion of the photosensitive composition by taking advantage of the characteristic that it dissolves by doing so.
- photopolymerizable monomer examples include 1,6-hexanediol di (meth) acrylate, ethylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, and bis [(().
- Bifunctional monomers such as bisphenol A, 3-methylpentanediol di (meth) acrylate, trimethyllol propatontri (meth) acrylate, pentaerythritol tri (meth) acrylate, tris (2-hydroxy)
- Polyfunctional monomers with relatively small molecular weight such as tri (meth) acrylates of ethyl) isocyanurate, dipentaerythritol hexa (meth) acrylates, dipentaerythritol penta (meth) acrylates, and ditrimethylolpropanetetra (meth) acrylates, polyester acrylates.
- (meth) acrylate is a general term for a combination of acrylate and methacrylate.
- photopolymerization initiator examples include acetophenone, benzophenone, benzyldimethylketanol, benzoyl peroxide, 2-chlorothioxanthone, 1,3-bis (4'-azidobenzal) -2-propane, and 1,3-bis (4).
- H. -Carbazole-3-yl] -1- (O-acetyloxime) can be mentioned.
- the cured film of the photosensitive composition has a maximum light transmittance in the wavelength range of 400 to 800 nm, which is suitable for a black matrix. It is 1% or less, and the light transmittance in the near-infrared region having a wavelength of 800 to 1100 nm can be 80%.
- the light transmittance of the black matrix is defined by a spectrophotometer for a black matrix (cured film) having a thickness of 3 ⁇ m formed on a transparent substrate such as a glass substrate, using the substrate on which the resin black matrix is not formed as a control. The measured light transmittance.
- the maximum light transmittance means the largest value in the light transmittance in a specific wavelength region (range). More specifically, it is the maximum value of the light transmittance curve in a specific wavelength region. For example, “the maximum light transmittance in the wavelength range of 400 nm to 800 nm is 1% or less” means that the maximum value of the light transmittance curve in the wavelength range of 400 nm to 800 nm is 1% or less, and light is emitted in this range. It means that there is no region where the transmittance exceeds 1%.
- wavelength 800 nm to 1100 nm means the so-called near-infrared region.
- a black matrix having a light transmittance of 80% or more in the near infrared region having a wavelength of 800 nm to 1100 nm is a black matrix having a small light absorption and a high light transmittance in the near infrared long region. The larger the light transmittance is, the easier it is for the black matrix to dissipate heat generated in the TFT element which is a heat generating source. Therefore, in the TFT element, the increase in on-current and off-current is small, and thermal runaway is less likely to occur.
- the volume resistivity is 1 ⁇ 10 13 ⁇ ⁇ cm or more and the dielectric constant is 5 or less, the short circuit of the TFT element (switching element composed of the thin film transistor) due to the leakage current can be reduced, and the TFT element can be reduced. Switching is accurately transmitted, and disturbance in the driving of the liquid crystal can be reduced.
- Volume resistivity is a measure of the insulating property of a substance and is the electrical resistance per unit volume.
- the volume resistivity is described in, for example, "Institute of Electrical Engineers of Japan, University Lecture, Electrical and Electronic Materials-From Basics to Test Methods-" (Ohmsha Co., Ltd., 2006, pp. 223 to 230). It can be measured by the method.
- the permittivity means the so-called relative permittivity, which is the ratio of the permittivity of a substance to the permittivity of a vacuum.
- the permittivity is defined by, for example, the method described in "Institute of Electrical Engineers of Japan, University Lecture, Electrical and Electronic Materials-From Basics to Test Methods-" (Ohmsha Co., Ltd., 2006, pp. 233 to 243). Can be measured by.
- the photosensitive composition of the present invention having such characteristics has a total of 3 to 20 parts of the alkali-soluble resin and the photopolymerizable monomer per 100 parts of the coloring composition of the present invention, and 0.05 per part of the photopolymerizable monomer.
- To 3 parts of the photopolymerization initiator and, if necessary, the organic solvent used for preparing the above-mentioned coloring composition are further added, and the mixture is stirred and dispersed so as to be uniform, and the photosensitivity for forming the black matrix part is formed.
- a sex composition can be obtained.
- the non-volatile content is at least 5 to 20% in terms of mass. It is preferable to prepare so as to be.
- a color filter may be manufactured by forming by a method such as a micelle electrolysis method or a PVED (Photolithography) method.
- the color filter As the color filter, 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 are used, and a liquid crystal material is enclosed between a pair of parallel transparent electrodes. Then, the transparent electrode is divided into discontinuous fine sections, and the fine sections divided in a grid pattern by the black matrix on the transparent electrode are each of red (R), green (G), and blue (B). It can be obtained by alternately providing a color filter colored pixel portion selected from any one color in a pattern, or by forming a color filter colored pixel portion on a substrate and then providing a transparent electrode.
- the black matrix portion obtained from the photosensitive composition of the present invention contains the above-mentioned blue, yellow, and red organic pigments so as to be black, and at first glance, the photosensitive compositions of each color are mixed. It seems that a black matrix similar to the case where the black photosensitive composition is prepared is obtained, but in the present invention, at the time of preparing the colored composition, which is a step before the photosensitive composition is prepared. As a result of mixing the organic pigments of each color in advance, more uniform mixing is achieved, and a black matrix having better characteristics can be obtained.
- the coloring composition of the present invention has a pH of 2 to 12 of an aqueous solution of a sulfonate compound obtained by mixing 0.5 part of a sulfonate compound represented by the formula (1) with 10 parts of pure water having a pH of 6 to 8. It is preferable that the sulfonate compound has a maximum absorbance in the wavelength range of 380 to 780 nm measured in accordance with JIS K 0115: 2004, which is 10% or less of the maximum absorbance of PV29. Further, the pH of the aqueous solution of the sulfonate compound is preferably 6 to 11 from the viewpoint of obtaining a dispersion having a particularly low viscosity.
- the pH of the above sulfonate compound aqueous solution can be measured using a pH meter in accordance with JIS Z8802: 2011. Further, for the maximum absorbance in the above wavelength range of 380 to 780 nm, the absorbance spectrum was measured with a spectrophotometer in accordance with JIS K 0115: 2004, and C.I. I. It is a relative value when the absorbance at the peak top of the absorption spectrum of an aqueous solution obtained by mixing 0.5 part of Pigment Violet 29 and 10 parts of pure water is set to 100.
- the acidity of the pigment is about 0.1 g of the sample in 0.001N tetrabutylammonium hydroxide (TBAH) / n-propyl acetate (NPAC) solution (or 0.001N p-toluenesulfonic acid (PTSA) / NPAC solution 15 ml).
- TBAH tetrabutylammonium hydroxide
- NPAC n-propyl acetate
- PTSA p-toluenesulfonic acid
- NPAC p-toluenesulfonic acid
- the pigment adsorption amount can be calculated by subtracting the above-mentioned unadsorbed amount from the added amount. Note that.
- the value obtained by dividing the base adsorption amount by the acid adsorption amount is defined as the colorant acid-base adsorption amount ratio, and the larger this value is, the higher the acidity is determined.
- the dispersion containing the coloring composition of the present invention contains PV29 and a sulfonate compound represented by the formula (1) as essential components, and disperses an organic solvent such as propylene glycol monomethyl ether acetate and a basic resin type dispersant. It is obtained by adding an agent, adding zirconia 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.
- the cured coating film of the color filter can be prepared by mixing the above dispersion liquid, an alkali-soluble resin, a photopolymerizable monomer, a photopolymerization initiator, and an organic solvent to form a photosensitive resin composition according to a standard method for producing a black matrix. ..
- part represents “part by mass”.
- Example 1 ⁇ Producing process of coloring composition> Pariogen Red Violet K 5411 (BASF Japan, CI Pigment Violet 29, colorant) 17 parts, BYK LPN-21116 (Big Chemie Co., Ltd., basic acrylic resin type dispersant) 44 parts, 2-naphthalene sulfonic acid Mix 2 parts of sodium (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., additive) and 218 parts of propylene glycol monomethyl ether acetate (manufactured by Claret Trading Co., Ltd., organic solvent), and add 0.2 to 0.3 mm ⁇ zirconia beads. , Dispersed with a paint conditioner (manufactured by Toyo Seiki Co., Ltd.) for 2 hours to obtain a colored composition (A-1).
- a paint conditioner manufactured by Toyo Seiki Co., Ltd.
- ⁇ Curing pattern manufacturing process> A 10 cm square glass substrate (Nippon Electric Glass color filter glass plate “OA-10") is immersed in a 1% diluted solution of Shin-Etsu Chemical's silane coupling agent "KBM-603" for 3 minutes, and washed with water for 10 seconds. After draining with an air gun, the mixture was dried in an oven at 110 ° C. for 5 minutes.
- the photosensitive resin composition (B-1) prepared above was applied onto this glass substrate using a spin coater. After vacuum drying for 1 minute, it was dried by heating on a hot plate at 90 ° C. for 90 seconds to obtain a coating film having a dry film thickness of about 3.5 ⁇ m.
- the image was exposed from the coating film side through a fine line pattern mask having a width of 15 ⁇ m.
- the exposure conditions were 50 mJ / cm2 (i-line standard) using a 3 kW high-pressure mercury lamp.
- a developer consisting of an aqueous solution containing 0.05% potassium hydroxide and 0.08% nonionic surfactant (“A-60” manufactured by Kao) was used, and a shower at 23 ° C. and a water pressure of 0.15 MPa was used.
- the development was stopped with pure water and washed with a water-washing spray to obtain a curing pattern (C-1).
- the shower development time was adjusted between 10 and 120 seconds, and was 1.5 times the time for dissolving and removing the unexposed coating film.
- ⁇ pH and absorbance of additives > 0.5 part of the additive and 10 parts of pure water (2 ⁇ S / cm or less and pH: 7.0 ⁇ 1.0 were used) were mixed.
- the pH was measured using a pH meter (PH71, manufactured by Yokogawa Electric Corporation).
- JISK 0115 2004, the absorption spectrum of the aqueous solution in the wavelength range of 380 to 780 nm was measured with a spectrophotometer (U3900, manufactured by Hitachi High-Tech Science Co., Ltd.), and Pariogen Red Violet K 5411 (CI Pigment Violet manufactured by BASF Corporation) was measured.
- Example 2 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of sodium p-toluenesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive), and the coloring composition (A-2) was carried out. Got The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-2), and a curing pattern (C-2) was obtained.
- Example 3 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of sodium allylsulfonate (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., additive), and the coloring composition (A-3) was performed. Got The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-3) to obtain a curing pattern (C-3).
- Example 4 The same operation as in Example 1 was carried out except that the additive of 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). rice field. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-4), and a curing pattern (C-4) was obtained.
- Example 5 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of sodium 2-morpholinoethanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive), and the coloring composition (A-5) was performed. ) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-5), and a curing pattern (C-5) was obtained.
- Example 6 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of 3-mercapto-1-sodium propanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive), and the coloring composition (colored composition). A-6) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-6) to obtain a curing pattern (C-6).
- Example 7 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to ( ⁇ ) -10-sodium camphorsulfonate (additive, manufactured by Tokyo Chemical Industry Co., Ltd.), and the coloring composition (colored composition). A-7) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-7) to obtain a curing pattern (C-7).
- Example 8 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of sodium 1-decylsulfonate (additive manufactured by Tokyo Chemical Industry Co., Ltd.), and the coloring composition (A-8) was carried out. Got The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-8) to obtain a curing pattern (C-8).
- Example 9 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of anthraquinone-2-sodium sulfonate monohydrate (manufactured by Tokyo Kasei Kogyo Co., Ltd., additive) to obtain a coloring composition. (A-9) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-9) to obtain a curing pattern (C-9).
- Example 10 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of anthraquinone-2,6-disodium disulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., additive), and the coloring composition (colored composition). A-10) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-10) to obtain a curing pattern (C-10).
- Example 1 The same operation as in Example 1 was carried out except that the additive of Example 1 was not added, to obtain a colored composition (A-11). The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-11), and a curing pattern (C-11) was obtained.
- Example 2 The colorant of Example 1 was changed to 17 parts of PALIOGEN RED L3880 HD (CI Pigment Red 178 manufactured by BASF Corporation, colorant), and the same operation as in Example 1 was performed except that no additive was added. , A coloring composition (A-12) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-12) to obtain a curing pattern (C-12).
- PALIOGEN RED L3880 HD CI Pigment Red 178 manufactured by BASF Corporation, colorant
- Example 3 The colorant of Example 1 was changed to 17 parts of 229-6438 (CI Pigment Red 179, Colorant manufactured by SUN CHEMICAL Co., Ltd.), and the same operation as in Example 1 was performed except that no additive was added. , A coloring composition (A-13) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-13) to obtain a curing pattern (C-13).
- Example 4 The same operation as in Example 1 was performed except that the colorant of Example 1 was changed to 17 parts of PALIOGEN RED L3880 HD (CI Pigment Red 178 manufactured by BASF Corporation, colorant), and the coloring composition (A) was performed. -14) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-14) to obtain a curing pattern (C-14).
- PALIOGEN RED L3880 HD CI Pigment Red 178 manufactured by BASF Corporation, colorant
- Example 5 The same operation as in Example 1 was performed except that the colorant of Example 1 was changed to 17 parts of 229-6438 (CI Pigment Red 179, Colorant manufactured by SUN CHEMICAL Co., Ltd.), and the coloring composition (A) was performed. -15) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-15) to obtain a curing pattern (C-15).
- Example 6 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of 2-naphthalene sulfonic acid (manufactured by Tokyo Chemical Industry Co., Ltd., additive) to obtain the coloring composition (A-16). Obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-16) to obtain a curing pattern (C-16).
- Example 7 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of p-toluenesulfonic acid monohydrate (manufactured by Wako Pure Chemical Industries, Ltd., additive) to form a coloring composition. (A-17) was obtained. The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-17) to obtain a curing pattern (C-17).
- Example 8 The same operation as in Example 1 was carried out except that the additive of Example 1 was changed to 2 parts of SOLSERSE 12000 (additive manufactured by Lubrizol Co., Ltd.) to obtain a colored composition (A-18). The same operation as in Example 1 was carried out except that the coloring composition (A-1) was changed to the coloring composition (A-18) to obtain a curing pattern (C-18).
- Pigment acidity (acid-base adsorption ratio) About 0.1 g of pigment is mixed with a 0.001N tetrabutylammonium hydroxide (TBAH) / n-propyl acetate (NPAC) solution or a 0.001N p-toluenesulfonic acid (PTSA) / NPAC solution 15 ml and a rotation / revolution stirrer (foam).
- TBAH tetrabutylammonium hydroxide
- NPAC n-propyl acetate
- PTSA 0.001N p-toluenesulfonic acid
- the pigment was precipitated by centrifugation (11,000 rpm, 20 minutes), and the amount of unadsorbed acid base in 10 ml of the supernatant was 0.001N PTSA /. It was measured by potential differential titration (COM-1700, manufactured by Hiranuma Sangyo Co., Ltd.) using NPAC or TBAH / NPAC solution. The acid-base adsorption amount on the pigment was calculated by subtracting the above-mentioned unadsorbed amount from the added amount.
- Viscosity As the viscosities of the coloring compositions (A-1) to (A-18) obtained in Examples 1 to 10 and Comparative Examples 1 to 8, an E-type viscometer (TVE-25L, manufactured by Toki Sangyo Co., Ltd.) ) The value of 30 rpm was measured.
- the viscosity system 1 using PV29 as a colorant the value of Comparative Example 1 was converted into 100 and shown in the table below.
- the value of Comparative Example 2 In the viscosity system 2 using PR178 as the colorant, the value of Comparative Example 2 was converted into 100 and shown in Table 1 below.
- the viscosity system 3 using PR179 as the colorant the value of Comparative Example 3 was converted into 100 and shown in Table 1 below.
- Curing degree Curing patterns (C-1) to (C-10), (C-11), (C-16) to (C) obtained in Examples 1 to 10, Comparative Example 1, and Comparative Examples 6 to 8 The results of visually confirming the presence or absence of pattern defects in -18) (curing degree “ ⁇ ” for those without defects and curing degree “ ⁇ ” for those with defects) are shown in Table 1 below as the degree of curing.
- Example 1 has a large effect of reducing the viscosity when the sulfonate is added. Further, in Examples 1 to 10 to which the non-dye-based sulfonate derivative was added, the degree of curing and the spectral purity even after the derivative was added, as compared with Comparative Example 8 in which the sulfonic acid derivative of the dye such as copper phthalocyanine sulfonic acid was combined. It can be seen that the sulfonic acid derivative of the dye such as copper phthalocyanine sulfonic acid was combined. It can be seen that the sulfonic acid derivative of the dye such as copper phthalocyanine sulfonic acid was combined. It can be seen that the sulfonic acid derivative of the dye such as copper phthalocyanine sulfonic acid was combined. It can be seen that the sulfonic acid derivative of the dye such as copper phthalocyanine sulfonic acid was combined. It can be seen that the sulfonic acid derivative
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Abstract
Description
C.I.ピグメントバイオレット29以外のペリレンは、酸性度の高いNH部が置換されており酸性度が低いため、酸性誘導体の母骨格がペリレンに吸着し、酸性基が分散剤のアミンと吸着するという機構で分散、低粘度化が進行するため、通常使用の範囲(1~20%程度添加)では酸が過剰となることはない。一方で、C.I.ピグメントバイオレット29は、酸性度の高いイミド部位N-Hを有しており、分散剤アミンと直接作用するため、酸性のスルホン酸誘導体を添加すると、酸が過剰となる。分散系中の酸塩基のバランスの観点から、酸が過剰となると顔料の凝集が促進され、粘度が高くなる。一方で塩基性の分散剤が過剰となると、分散剤高分子同士の絡まりあいにより粘度が高くなる。よって、C.I.ピグメントバイオレット29分散系におけるスルホン酸塩は、系中の酸性度を上げずに過剰なアミンと作用することで、前記の分散剤分子の絡まりあいによる高粘度化を防ぐことができる。
項1. 下記式(1)で表されるスルホン酸塩化合物と、C.I.ピグメントバイオレット29とを含む着色組成物。
A-SO3M・nH2O 式(1)
[式(1)中のAは、ハロゲン、ホウ素、窒素、硫黄、リン、酸素を構造中に有していてもよい炭素数1~20の炭化水素基であり、Mは、Hを除く1~3価のカチオンの1当量であり、nは0~5の整数である]
項2. 下記式(1)で表されるスルホン酸塩化合物0.5部をpHが6~8である純水10部に混合したスルホン酸塩化合物水溶液のpHが2~12であり、且つJISK 0115:2004に従い測定した波長域380~780nmにおける最大吸光度が、C.I.ピグメントバイオレット29の最大吸光度の10%以下であるスルホン酸塩化合物である項1に記載の着色組成物。
A-SO3M・nH2O 式(1)
[式(1)中のAは、ハロゲン、ホウ素、窒素、硫黄、リン、酸素を構造中に有していてもよい炭素数1~20の炭化水素基であり、Mは、Hを除く1~3価のカチオンの1当量であり、nは0~5の整数である]
項3. 前記スルホン酸塩化合物水溶液pHが6~11である項2に記載の着色組成物。
項4. 前記式(1)で表されるスルホン酸塩化合物が、ベンゼンスルホン酸塩、トルエンスルホン酸塩、ナフタレンスルホン酸塩、アントラキノンスルホン酸塩、2-モルホリノアルキルスルホン酸塩、アリルスルホン酸塩、(±)-10-カンファースルホン酸塩、直鎖アルキルスルホン酸塩、分岐アルキルスルホン酸塩から選ばれる少なくとも1つのスルホン酸塩化合物である項1~3のいずれか1項に記載の着色組成物。
項5. 前記式(1)で表されるスルホン酸塩化合物が、下記式(1-1)~(1-10)
で表される化合物、2-ナフタレンスルホン酸ナトリウム、2-モルホリノエタンスルホン酸ナトリウム、p-トルエンスルホン酸ナトリウム、メタンスルホン酸カリウム、3-メルカプト-1-プロパンスルホン酸ナトリウム、アリルスルホン酸ナトリウム、(±)-10-カンファースルホン酸ナトリウム、及び1-デカンスルホン酸ナトリウムからなる群より選択される少なくとも1つの化合物である項1~4のいずれか1項に記載の着色組成物。
項6. 項1~5のいずれか1項に記載の着色組成物を含有するカラーフィルタ。
本発明の着色組成物は、下記式(1)で表されるスルホン酸塩化合物と、C.I.ピグメントバイオレット29(以下、「PV29」と称する)とを含む。
A-SO3M・nH2O 式(1)
[式(1)中のAは、ハロゲン、ホウ素、窒素、硫黄、リン、酸素を構造中に有していてもよい炭素数1~20の炭化水素基であり、Mは、Hを除く1~3価のカチオンの1当量であり、nは0~5の整数である]
で表される化合物、2-ナフタレンスルホン酸ナトリウム、2-モルホリノエタンスルホン酸ナトリウム、p-トルエンスルホン酸ナトリウム、メタンスルホン酸カリウム、3-メルカプト-1-プロパンスルホン酸ナトリウム、アリルスルホン酸ナトリウム、(±)-10-カンファースルホン酸ナトリウム、及び1-デカンスルホン酸ナトリウムからなる群より選択される少なくとも1つの化合物であることが好ましい。
有機溶剤としては、例えば、ジイソプロピルエーテル、ミネラルスピリット、n-ペンタン、アミルエーテル、エチルカプリレート、n-ヘキサン、ジエチルエーテル、イソプレン、エチルイソブチルエーテル、ブチルステアレート、n-オクタン、バルソル#2、アプコ#18ソルベント、ジイソブチレン、アミルアセテート、ブチルアセテート、アプコシンナー、ブチルエーテル、ジイソブチルケトン、メチルシクロヘキセン、メチルノニルケトン、プロピルエーテル、ドデカン、ソーカルソルベントNo.1及びNo.2、アミルホルメート、ジヘキシルエーテル、ジイソプロピルケトン、ソルベッソ#150、(n,sec,t-)酢酸ブチル、ヘキセン、シェルTS28 ソルベント、ブチルクロライド、エチルアミルケトン、エチルベンゾエート、アミルクロライド、エチレングリコールジエチルエーテル、エチルオルソホルメート、メトキシメチルペンタノン、メチルブチルケトン、メチルヘキシルケトン、メチルイソブチレート、ベンゾニトリル、エチルプロピオネート、メチルセロソルブアセテート、メチルイソアミルケトン、n-アミルメチルケトン(2-ヘプタノン)、メチルイソブチルケトン、プロピルアセテート、アミルアセテート、アミルホルメート、ビシクロヘキシル、ジエチレングリコールモノエチルエーテルアセテート、ジペンテン、メトキシメチルペンタノール、メチルアミルケトン、メチルイソプロピルケトン、プロピルプロピオネート、プロピレングリコール-t-ブチルエーテル、メチルエチルケトン、メチルセロソルブ、エチルセロソルブ、エチルセロソルブアセテート、カルビトール、シクロヘキサノン、酢酸エチル、プロピレングリコール、プロピレングリコールモノメチルエーテル、プロピレングリコールモノメチルエーテルアセテート、プロピレングリコールモノエチルエーテル、プロピレングリコールモノエチルエーテルアセテート、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノメチルエーテルアセテート、3-メトキシプロピオン酸、3-エトキシプロピオン酸、3-エトキシプロピオン酸メチル、3-エトキシプロピオン酸エチル、3-メトキシプロピオン酸メチル、3-メトキシプロピオン酸エチル、3-メトキシプロピオン酸プロピル、3-メトキシプロピオン酸ブチル、ジグライム、エチレングリコールアセテート、エチルカルビトール、ブチルカルビトール、エチレングリコールモノブチルエーテル、プロピレングリコール-t-ブチルエーテル、3-メトキシブタノール、3-メチル-3-メトキシブタノール、トリプロピレングリコールメチルエーテルが挙げられる。
<着色組成物の作製工程>
Paliogen Red Violet K 5411(BASF株式会社製C.I.ピグメントバイオレット29、着色剤)17部、BYK LPN-21116(ビックケミー株式会社製、塩基性アクリル樹脂型分散剤)44部、2-ナフタレンスルホン酸ナトリウム(富士フイルム和光純薬株式会社製、添加剤)2部、プロピレングリコールモノメチルエーテルアセテート(クラレトレーディング株式会社製、有機溶剤)218部を混合し、0.2~0.3mmφのジルコニアビーズを加え、ペイントコンディショナー(東洋精機株式会社製)で2時間分散し、着色組成物(A-1)を得た。
着色組成物(A-1)100部、アルカリ可溶性樹脂としてメタクリル酸/こはく酸モノ(2-メタクリロイロキシエチル)/N-フェニルマレイミド/スチレン/ベンジルメタクリレート共重合体(共重合質量比=25/10/30/20/15、Mw=12,000、Mn=6,500)5部、光重合性モノマーとしてジペンタエリスリトールヘキサアクリレート10部、光重合開始剤としてエタノン,1-〔9-エチル-6-[2-メチル-4-(2,2-ジメチル-1,3-ジオキソラニル)メトキシベンゾイル]-9.H.-カルバゾール-3-イル〕-1-(O-アセチルオキシム)を1部、および有機溶剤としてジプロピレングリコールジメチルエーテル25部、プロピレングリコールモノメチルエーテルアセテート25部、3-メトキシブチルアセテート75部、シクロヘキサノン50部を混合して、感光性樹脂組成物(B-1)を調製した。
10cm角のガラス基板(日本電気硝子製カラーフィルタ用ガラス板「OA-10」)を信越化学製シランカップリング剤「KBM-603」の1%希釈液に3分間浸漬し、10秒間水洗して、エアーガンで水切り後、110℃のオーブンで5分間乾燥した。このガラス基板上に、上記にて調製した感光性樹脂組成物(B-1)を、スピンコーターを用いて塗布した。1分間真空乾燥後、ホットプレート上で90℃にて90秒間加熱乾燥し、乾燥膜厚約3.5μmの塗布膜を得た。その後、塗布膜側から、15μm幅の細線パターンマスクを介して画像露光を行った。露光条件は、3kW高圧水銀灯を用い50mJ/cm2(i線基準)とした。次いで、0.05%の水酸化カリウムと0.08%のノニオン性界面活性剤(花王製「A-60」)を含有する水溶液よりなる現像液を用い、23℃において水圧0.15MPaのシャワー現像を施した後、純水にて現像を停止し、水洗スプレーにて洗浄し硬化パターン(C-1)を得た。なお、シャワー現像時間は、10~120秒間の間で調整し、未露光の塗布膜が溶解除去される時間の1.5倍とした。
添加剤0.5部および純水(2μS/cm以下およびpH:7.0±1.0を使用)10部を混合した。JIS Z 8802 :2011に従い、pHメーター(PH71、横河電機株式会社製)を用いてpHを測定した。JISK 0115:2004に従い、波長域380~780nmにおける水溶液の吸光スペクトルを分光光度計(U3900、株式会社日立ハイテクサイエンス製)により測定し、Paliogen Red Violet K 5411(BASF株式会社製C.I.ピグメントバイオレット29、着色剤)0.5部および純水(2μS/cm以下およびpH:7.0±1.0を使用)10部を混合した分散液の吸光スペクトルのピークトップの吸光度を100としたときの吸光度を下表1に記載した。
実施例1の添加剤をp-トルエンスルホン酸ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-2)を得た。着色組成物(A-1)を着色組成物(A-2)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-2)を得た。
実施例1の添加剤をアリルスルホン酸ナトリウム(富士フイルム和光純薬株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-3)を得た。着色組成物(A-1)を着色組成物(A-3)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-3)を得た。
実施例1の添加剤をメタンスルホン酸カリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-4)を得た。着色組成物(A-1)を着色組成物(A-4)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-4)を得た。
実施例1の添加剤を2-モルホリノエタンスルホン酸ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-5)を得た。着色組成物(A-1)を着色組成物(A-5)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-5)を得た。
実施例1の添加剤を3-メルカプト-1-プロパンスルホン酸ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-6)を得た。着色組成物(A-1)を着色組成物(A-6)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-6)を得た。
実施例1の添加剤を(±)-10-カンファースルホン酸ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-7)を得た。着色組成物(A-1)を着色組成物(A-7)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-7)を得た。
実施例1の添加剤を1-デカンスルホン酸ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-8)を得た。着色組成物(A-1)を着色組成物(A-8)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-8)を得た。
実施例1の添加剤をアントラキノン-2-スルホン酸ナトリウム一水和物(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-9)を得た。着色組成物(A-1)を着色組成物(A-9)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-9)を得た。
実施例1の添加剤をアントラキノン-2,6-ジスルホン酸二ナトリウム(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-10)を得た。着色組成物(A-1)を着色組成物(A-10)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-10)を得た。
実施例1の添加剤を添加しない以外は上記実施例1と同様な操作を行い、着色組成物(A-11)を得た。着色組成物(A-1)を着色組成物(A-11)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-11)を得た。
実施例1の着色剤をPALIOGEN RED L3880 HD(BASF株式会社製C.I.ピグメントレッド178、着色剤)17部に変更し、添加剤を添加しない以外は上記実施例1と同様な操作を行い、着色組成物(A-12)を得た。着色組成物(A-1)を着色組成物(A-12)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-12)を得た。
実施例1の着色剤を229-6438(SUN CHEMICAL株式会社製C.I.ピグメントレッド179、着色剤)17部に変更し、添加剤を添加しない以外は上記実施例1と同様な操作を行い、着色組成物(A-13)を得た。着色組成物(A-1)を着色組成物(A-13)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-13)を得た。
実施例1の着色剤をPALIOGEN RED L3880 HD(BASF株式会社製C.I.ピグメントレッド178、着色剤)17部に変更する以外は上記実施例1と同様な操作を行い、着色組成物(A-14)を得た。着色組成物(A-1)を着色組成物(A-14)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-14)を得た。
実施例1の着色剤を229-6438(SUN CHEMICAL株式会社製C.I.ピグメントレッド179、着色剤)17部に変更する以外は上記実施例1と同様な操作を行い、着色組成物(A-15)を得た。着色組成物(A-1)を着色組成物(A-15)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-15)を得た。
実施例1の添加剤を2-ナフタレンスルホン酸(東京化成工業株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-16)を得た。着色組成物(A-1)を着色組成物(A-16)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-16)を得た。
実施例1の添加剤をp-トルエンスルホン酸1水和物(富士フイルム和光純薬株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-17)を得た。着色組成物(A-1)を着色組成物(A-17)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-17)を得た。
実施例1の添加剤をSOLSPERSE12000(ルーブリゾール株式会社製、添加剤)2部に変更した以外は上記実施例1と同様な操作を行い、着色組成物(A-18)を得た。着色組成物(A-1)を着色組成物(A-18)に変更した以外は上記実施例1と同様な操作を行い、硬化パターン(C-18)を得た。
・顔料の酸性度(酸塩基吸着量比)
顔料約0.1gを0.001N水酸化テトラブチルアンモニウム(TBAH)/酢酸n-プロピル(NPAC)溶液、または0.001N p-トルエンスルホン酸(PTSA)/NPAC溶液15mlと自転公転撹拌機(泡取り錬太郎、シンキー株式会社製)で3分間混合撹拌した後、遠心分離(11,000rpm,20分)により顔料を沈澱させ、上澄み液10ml中の未吸着の酸塩基量を0.001N PTSA/NPACまたはTBAH/NPAC溶液を用いた電位差滴定(COM-1700、平沼産業株式会社製)により測定した。顔料への酸塩基吸着量は添加量から上記の未吸着量を引くことで算出した。塩基吸着量を酸吸着量で除した値を着色剤酸塩基吸着量比とし、この値が大きいほど酸性度が高いと判定した。PV29は同じペリレンであるC.I.ピグメントレッド178(PR178)、C.I.ピグメントレッド179(PR179)に比べはるかに酸性度が高いことを確認した。
実施例1~10及び比較例1~8で得られた着色組成物(A-1)~(A-18)の粘度として、E型粘度計(TVE-25L、東機産業株式会社製)30rpmの値を測定した。着色剤としてPV29を使用した粘度系1では比較例1の値を100に換算して、下表に記載した。着色剤としてPR178を使用した粘度系2では比較例2の値を100に換算して、下表1に記載した。着色剤としてPR179を使用した粘度系3では比較例3の値を100に換算して、下記表1に記載した。
実施例1~10、比較例1、比較例6~8で得られた硬化パターン(C-1)~(C-10)、(C-11)、(C-16)~(C-18)のパターン欠損の有無(欠損がないものは硬化度「○」、欠損があるものは硬化度「×」)を目視で確認した結果を硬化度として下記表1に記載した。
実施例1~10、比較例1、比較例6~8で得られた硬化パターン(C-1)~(C-10)、(C-11)、及び(C-16)~(C-18)の吸光スペクトルを分光光度計(U3900、株式会社日立ハイテクサイエンス製)により測定し、波長域380~780nmにおける吸光スペクトルのピークトップの吸光度の3%以上の強度を示すPV29以外の吸光ピークがないものは「〇」、あるものは「×」として下記表1に記載した。
Claims (6)
- 下記式(1)で表されるスルホン酸塩化合物と、C.I.ピグメントバイオレット29とを含む着色組成物。
A-SO3M・nH2O 式(1)
[式(1)中のAは、ハロゲン、ホウ素、窒素、硫黄、リン、酸素を構造中に有していてもよい炭素数1~20の炭化水素基であり、Mは、Hを除く1~3価のカチオンの1当量であり、nは0~5の整数である] - 下記式(1)で表されるスルホン酸塩化合物0.5部をpHが6~8である純水10部に混合したスルホン酸塩化合物水溶液のpHが2~12であり、且つJISK 0115:2004に従い測定した波長域380~780nmにおける最大吸光度が、C.I.ピグメントバイオレット29の最大吸光度の10%以下であるスルホン酸塩化合物である請求項1に記載の着色組成物。
A-SO3M・nH2O 式(1)
[式(1)中のAは、ハロゲン、ホウ素、窒素、硫黄、リン、酸素を構造中に有していてもよい炭素数1~20の炭化水素基であり、Mは、Hを除く1~3価のカチオンの1当量であり、nは0~5の整数である] - 前記スルホン酸塩化合物水溶液pHが6~11である請求項2に記載の着色組成物。
- 前記式(1)で表されるスルホン酸塩化合物が、ベンゼンスルホン酸塩、トルエンスルホン酸塩、ナフタレンスルホン酸塩、アントラキノンスルホン酸塩、2-モルホリノアルキルスルホン酸塩、アリルスルホン酸塩、(±)-10-カンファースルホン酸塩、直鎖アルキルスルホン酸塩、分岐アルキルスルホン酸塩から選ばれる少なくとも1つのスルホン酸塩化合物である請求項1~3のいずれか1項に記載の着色組成物。
- 前記式(1)で表されるスルホン酸塩化合物が、下記式(1-1)~(1-10)
式(1-1)
式(1-2)
式(1-3)
式(1-4)
式(1-5)
式(1-6)
式(1-7)
式(1-8)
式(1-9)
式(1-10)
で表される化合物、2-ナフタレンスルホン酸ナトリウム、2-モルホリノエタンスルホン酸ナトリウム、p-トルエンスルホン酸ナトリウム、メタンスルホン酸カリウム、3-メルカプト-1-プロパンスルホン酸ナトリウム、アリルスルホン酸ナトリウム、(±)-10-カンファースルホン酸ナトリウム、及び1-デカンスルホン酸ナトリウムからなる群より選択される少なくとも1つの化合物である請求項1~4のいずれか1項に記載の着色組成物。 - 請求項1~5のいずれか1項に記載の着色組成物を含有するカラーフィルタ。
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| KR1020227029982A KR20230050263A (ko) | 2020-08-13 | 2021-06-10 | 착색 조성물, 및 컬러 필터 |
| JP2021559342A JP7006861B1 (ja) | 2020-08-13 | 2021-06-10 | 着色組成物、及びカラーフィルタ |
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| WO2022034734A1 true WO2022034734A1 (ja) | 2022-02-17 |
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| JP (1) | JP7006861B1 (ja) |
| KR (1) | KR20230050263A (ja) |
| CN (1) | CN115210324B (ja) |
| TW (1) | TWI889874B (ja) |
| WO (1) | WO2022034734A1 (ja) |
Citations (3)
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|---|---|---|---|---|
| WO2015015962A1 (ja) * | 2013-08-01 | 2015-02-05 | Dic株式会社 | カラーフィルタ用顔料組成物及びカラーフィルタ |
| WO2019065359A1 (ja) * | 2017-09-28 | 2019-04-04 | 東レ株式会社 | 有機el表示装置、ならびに画素分割層および平坦化層の形成方法 |
| JP2019081831A (ja) * | 2017-10-30 | 2019-05-30 | サカタインクス株式会社 | 黒色着色組成物及びそれを含有する黒色着色レジスト組成物 |
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| JP2870295B2 (ja) * | 1992-04-17 | 1999-03-17 | 東洋インキ製造株式会社 | 塗料組成物 |
| DE4325247A1 (de) * | 1993-07-28 | 1995-02-02 | Basf Ag | Pigmentzubereitungen mit Perylenderivaten als Dispergiermitteln |
| JPH0915857A (ja) * | 1995-06-29 | 1997-01-17 | Hitachi Chem Co Ltd | 着色画像形成材料、これを用いた感光液、感光性エレメント及びカラーフィルタの製造法 |
| JP4481445B2 (ja) * | 2000-07-07 | 2010-06-16 | サカタインクス株式会社 | カラーフィルター用赤色系顔料分散物 |
| JP2002283706A (ja) * | 2001-03-26 | 2002-10-03 | Mitsubishi Paper Mills Ltd | インクジェット記録シート |
| JP3954863B2 (ja) * | 2002-02-19 | 2007-08-08 | サカタインクス株式会社 | カラーフィルタ用赤色系顔料分散レジスト組成物 |
| JP2005213403A (ja) | 2004-01-30 | 2005-08-11 | Toyo Ink Mfg Co Ltd | カーボンブラックおよび有機顔料分散液の製造方法 |
| JP2008050407A (ja) * | 2006-08-22 | 2008-03-06 | Fujifilm Corp | 有機顔料微粒子を含む光重合性組成物 |
| JP2008304766A (ja) * | 2007-06-08 | 2008-12-18 | Mitsubishi Chemicals Corp | カラーフィルター用着色樹脂組成物、カラーフィルター、有機elディスプレイおよび液晶表示装置 |
| JP2009069822A (ja) | 2007-08-22 | 2009-04-02 | Mitsubishi Chemicals Corp | 樹脂ブラックマトリックス、遮光性感光性樹脂組成物、tft素子基板及び液晶表示装置 |
| JP2009203308A (ja) * | 2008-02-27 | 2009-09-10 | Fujifilm Corp | 放射線硬化性インク組成物及びその製造方法 |
| JP5498724B2 (ja) * | 2009-05-15 | 2014-05-21 | 凸版印刷株式会社 | カラーフィルタ、及び液晶表示装置 |
| JP5738091B2 (ja) * | 2011-06-30 | 2015-06-17 | 株式会社日本触媒 | 感光性樹脂組成物 |
| TWI791690B (zh) * | 2017-12-14 | 2023-02-11 | 日商迪愛生股份有限公司 | 著色組成物及濾色器 |
| JP2019139230A (ja) * | 2018-02-13 | 2019-08-22 | 東洋インキScホールディングス株式会社 | 感光性着色組成物及びカラーフィルタ |
| KR102791487B1 (ko) * | 2018-08-07 | 2025-04-08 | 오츠카 가가쿠 가부시키가이샤 | 분산제 조성물, 착색 조성물, 및, 컬러 필터 |
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2021
- 2021-06-10 US US17/798,660 patent/US20230101363A1/en not_active Abandoned
- 2021-06-10 JP JP2021559342A patent/JP7006861B1/ja active Active
- 2021-06-10 KR KR1020227029982A patent/KR20230050263A/ko active Pending
- 2021-06-10 WO PCT/JP2021/022016 patent/WO2022034734A1/ja not_active Ceased
- 2021-06-10 CN CN202180017911.3A patent/CN115210324B/zh active Active
- 2021-07-19 TW TW110126476A patent/TWI889874B/zh active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015015962A1 (ja) * | 2013-08-01 | 2015-02-05 | Dic株式会社 | カラーフィルタ用顔料組成物及びカラーフィルタ |
| WO2019065359A1 (ja) * | 2017-09-28 | 2019-04-04 | 東レ株式会社 | 有機el表示装置、ならびに画素分割層および平坦化層の形成方法 |
| JP2019081831A (ja) * | 2017-10-30 | 2019-05-30 | サカタインクス株式会社 | 黒色着色組成物及びそれを含有する黒色着色レジスト組成物 |
Also Published As
| Publication number | Publication date |
|---|---|
| US20230101363A1 (en) | 2023-03-30 |
| KR20230050263A (ko) | 2023-04-14 |
| TW202206528A (zh) | 2022-02-16 |
| JPWO2022034734A1 (ja) | 2022-02-17 |
| CN115210324B (zh) | 2025-02-21 |
| TWI889874B (zh) | 2025-07-11 |
| JP7006861B1 (ja) | 2022-02-10 |
| CN115210324A (zh) | 2022-10-18 |
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