CN113641080A - Pigment dispersion composition for black matrix and pigment dispersion resist composition for black matrix - Google Patents
Pigment dispersion composition for black matrix and pigment dispersion resist composition for black matrix Download PDFInfo
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- CN113641080A CN113641080A CN202110459468.7A CN202110459468A CN113641080A CN 113641080 A CN113641080 A CN 113641080A CN 202110459468 A CN202110459468 A CN 202110459468A CN 113641080 A CN113641080 A CN 113641080A
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
- G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
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- 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
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/013—Fillers, pigments or reinforcing additives
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- 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
- C08K3/02—Elements
- C08K3/04—Carbon
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- 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
- C08K3/10—Metal compounds
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- 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
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- 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
- C08K3/24—Acids; Salts thereof
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- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0041—Optical brightening agents, organic pigments
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/0045—Photosensitive materials with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
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- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/80—Constructional details
- H10K50/86—Arrangements for improving contrast, e.g. preventing reflection of ambient light
- H10K50/865—Arrangements for improving contrast, e.g. preventing reflection of ambient light comprising light absorbing layers, e.g. light-blocking layers
Abstract
The present invention relates to a pigment-dispersion composition for a black matrix, which includes carbon black and/or lactam black, a pigment dispersant containing a basic group, an alkali-soluble resin, and a solvent, and further includes one or more inorganic compounds selected from the group consisting of barium titanate, aluminum oxide, and aluminum hydroxide, the inorganic compounds being 30 parts by mass or less with respect to 100 parts by mass of the carbon black and/or lactam black, and a pigment-dispersed photoresist composition for a black matrix. The pigment dispersion composition for black matrix has excellent dispersion stability, and can obtain pigment dispersion photoresist composition for black matrix with good developer reusability.
Description
Technical Field
The present invention relates to a pigment-dispersion composition for a black matrix and a pigment-dispersion photo-resist composition for a black matrix.
Background
Conventionally, a pigment-dispersion composition for a black matrix containing carbon black and/or lactam black, a pigment dispersant containing a basic group, an alkali-soluble resin, and a solvent, and a pigment-dispersion resist composition for a black matrix containing the pigment-dispersion composition for a black matrix, a photopolymerizable compound, and a photopolymerization initiator are known (patent documents 1 to 6).
[ Prior art documents ]
[ patent document ]
Patent document 1: japanese patent laid-open publication No. 2014-102346
Patent document 2: international publication No. 2015/056688
Patent document 3: japanese patent laid-open publication No. 2016-79245
Patent document 4: japanese patent laid-open publication No. 2019-81831
Patent document 5: japanese patent laid-open publication No. 2019-81857
Patent document 6: japanese patent laid-open publication No. 2019-82533
Disclosure of Invention
[ problem to be solved by the invention ]
In forming a pattern of a black matrix using the pigment dispersion resist composition for a black matrix as described above, generally, after the pigment dispersion resist composition for a black matrix is coated on a substrate to form a resist film, ultraviolet rays are exposed through a photomask having a desired pattern, and after the resist film of the exposed portion is hardened, the resist film of the unexposed portion is removed using a developing solution.
On the other hand, the developer is required to be reusable in terms of improvement of productivity, and the pigment dispersion composition for a black matrix described in the above patent document still has room for improvement of the performance.
In addition, in general, a pigment-dispersed photoresist composition for a black matrix is prepared by mixing a pigment-dispersed composition for a black matrix, a photopolymerizable compound, a photopolymerization initiator, and the like before coating, and thus the pigment-dispersed composition for a black matrix is required to have dispersion stability upon storage.
The present invention has been made in view of the above circumstances, and an object thereof is to provide a pigment dispersion resist composition for a black matrix which is obtainable with good developer reusability and a pigment dispersion composition for a black matrix which is excellent in dispersion stability.
[ means for solving the problems ]
The present invention relates to a pigment-dispersion composition for a black matrix, which comprises carbon black and/or lactam black, a pigment dispersant containing a basic group, an alkali-soluble resin, and a solvent, and further comprises one or more inorganic compounds selected from the group consisting of barium titanate, aluminum oxide, and aluminum hydroxide, wherein the inorganic compound is 30 parts by mass or less with respect to 100 parts by mass of the carbon black and/or lactam black.
Further, the present invention relates to a pigment-dispersed photo-resist composition for a black matrix, which comprises the pigment-dispersed composition for a black matrix, a photopolymerizable compound and a photopolymerization initiator.
[ technical effects of the invention ]
The detailed mechanism of action of the effect of the pigment dispersion composition for a black matrix of the present invention is not clear, but it is presumed as follows. However, the present invention is not limited to this mechanism of action.
The pigment dispersion composition for a black matrix of the present invention comprises carbon black and/or lactam black, a pigment dispersant containing a basic group, an alkali-soluble resin, and a solvent, and further comprises one or more inorganic compounds selected from the group consisting of barium titanate, aluminum oxide, and aluminum hydroxide, wherein the inorganic compound is 30 parts by mass or less with respect to 100 parts by mass of the carbon black and/or lactam black. In the pigment-dispersion composition for a black matrix of the present invention, since the inorganic compound is contained in an amount of a certain amount or less relative to the carbon black and/or the lactam black, the dispersion stability is excellent, and since the inorganic compound is contained, the pigment-dispersion resist composition for a black matrix is less likely to be affected by a reusable developer, and thus a pigment-dispersion resist composition for a black matrix having good reusability of the developer can be obtained. Further, the reusability of the developer is evaluated from the developability and adhesion of the resist pattern described in patent document 1 and the like.
Detailed Description
The pigment-dispersion composition for a black matrix of the present invention comprises carbon black and/or lactam black, a pigment dispersant containing a basic group, an alkali-soluble resin, and a solvent, and further comprises one or more inorganic compounds selected from the group consisting of barium titanate, aluminum oxide, and aluminum hydroxide.
Inorganic compound
The inorganic compound is one or more selected from the group consisting of barium titanate, aluminum oxide, and aluminum hydroxide. The inorganic compounds may be used alone or in combination of two or more.
The inorganic compound preferably has an average primary particle diameter of 20nm or more, more preferably 30nm or more, from the viewpoint of obtaining a pigment dispersion resist composition for a black matrix having good developer reusability, and preferably 2000nm or less, more preferably 1700nm or less, from the viewpoint of preventing precipitation of the inorganic compound in the pigment dispersion composition or the resist composition. In general, the average primary particle diameter is a value of an arithmetic average particle diameter obtained by observation with an electron microscope, but in the case of a commercially available product, a catalog value is referred to.
The inorganic compound is 30 parts by mass or less with respect to 100 parts by mass of the carbon black and/or the lactam black. The inorganic compound is preferably 1 part by mass or more, more preferably 2 parts by mass or more, with respect to 100 parts by mass of the carbon black and/or the lactam black, in terms of obtaining a pigment-dispersed photoresist composition for a black matrix having good developer reusability, and is preferably 25 parts by mass or less, more preferably 20 parts by mass or less, in terms of obtaining a pigment-dispersed photoresist composition for a black matrix having good developer reusability and improving dispersion stability.
Carbon black and/or lactam black
As the carbon black, known carbon blacks used in pigment dispersion compositions for black matrices can be used, and examples thereof include neutral carbon blacks and acidic carbon blacks. Further, the average primary particle diameter of the carbon black is preferably about 20 to 60 nm. Examples of the lactam black include compounds having the following structures. The carbon black and/or the lactam black may be used alone or in combination of two or more.
[ Compound 1]
The pH value of the neutral carbon black is preferably in the range of 8-10. Examples of commercially available neutral carbon blacks include: printex25 (average primary particle size 56nm, pH 9.5), Printex35 (average primary particle size 31nm, pH 9.5), Printex65 (average primary particle size 21nm, pH 9.5), manufactured by Orion Engineered Carbons, MA #20 (average primary particle size 40nm, pH 8.0), MA #40 (average primary particle size 40nm, pH 8.0), MA #30 (average primary particle size 30nm, pH 8.0), manufactured by Mitsubishi chemical corporation, and the like.
The pH of the acidic carbon black is preferably in the range of 2 to 4. Examples of commercially available acid carbon blacks include: raven1080 (average primary particle size of 28nm, pH 2.4) manufactured by Columbia Chemical company, Raven1100 (average primary particle size of 32nm, pH 2.9), MA-8 (average primary particle size of 24nm, pH 3.0) manufactured by mitsubishi Chemical corporation, MA-100 (average primary particle size of 22nm, pH 3.5), MA #70 (average primary particle size of 24nm, pH 3.0), Special Black 250 (average primary particle size of 56nm, pH 3.0) manufactured by Orion Engineered carbon corporation, Special Black 350 (average primary particle size of 31nm, pH 3.0), Special Black 550 (average primary particle size of 25nm, pH 4), NEROX2500 (average primary particle size of 56nm, pH 3.0), NEROX3500 (average primary particle size of 31nm, pH 3.0), and the like.
Further, in general, the pH is determined as follows: an aqueous suspension was prepared by adding 1g of carbon black to 20mL of distilled water (pH 7.0) from which carbonic acid was removed and mixing the mixture with a magnetic stirrer, and the measurement was carried out at 25 ℃ using a glass electrode (German Industrial Standard DIN ISO 787/9). In addition, the average primary particle diameter is usually a value of an arithmetic average particle diameter obtained by observation using an electron microscope. However, the pH and average primary particle size of the above commercially available carbon black are listed values.
In the pigment-dispersion composition for a black matrix, the carbon black and/or the lactam black is preferably 3% by mass or more, more preferably 10% by mass or more, in terms of improving the light-shielding property when the black matrix is formed, and is preferably 70% by mass or less, more preferably 50% by mass or less, in terms of pigment dispersion.
Pigment dispersants containing basic groups
The pigment dispersant containing a basic group may be any pigment dispersant capable of dispersing the carbon black and/or the lactam black, and a known pigment dispersant containing a basic group used for a pigment-dispersion composition for a black matrix may be used, and examples thereof include: an anionic surfactant, a polyester type pigment dispersant containing a basic group, an acrylic type pigment dispersant containing a basic group, a urethane type pigment dispersant containing a basic group, a carbodiimide type pigment dispersant containing a basic group, and the like. As the basic group, a primary amino group, a secondary amino group, or a tertiary amino group is preferable, particularly in terms of excellent dispersibility. The basic group-containing pigment dispersant may be used alone or in combination of two or more.
The basic group-containing pigment dispersant is preferably a polymeric basic group-containing pigment dispersant in terms of obtaining good pigment dispersibility. Examples of the polymeric basic group-containing pigment dispersant include: a basic group-containing urethane type polymer pigment dispersant, a basic group-containing polyester type polymer pigment dispersant, a basic group-containing acrylic type polymer pigment dispersant, and the like. Among them, it is preferably a urethane type polymer pigment dispersant containing a basic group or an acrylic type polymer pigment dispersant containing a basic group. The basic group-containing urethane type polymeric pigment dispersant is more preferably a basic group-containing urethane type polymeric pigment dispersant having at least one selected from the group consisting of a polyester chain, a polyether chain and a polycarbonate chain.
The pigment dispersant containing a basic group is preferably 1 to 100 parts by mass, more preferably 2 to 50 parts by mass, per 100 parts by mass of the carbon black and/or the lactam black.
Alkali soluble resin
The alkali-soluble resin is not particularly limited as long as it is soluble in an alkali developer, and is preferablySelected from carboxyl, sulfonic acid group and phosphonic acid group (-P (═ O) (OH)2) ) or the like, or one or more types of anionic groups. The alkali-soluble resin may be used alone or in combination of two or more.
In terms of alkali developability, the acid value of the alkali-soluble resin is preferably 10mgKOH/g or more and 300mgKOH/g or less, and more preferably 20mgKOH/g or more and 200mgKOH/g or less.
In terms of the formation property of the resist film, the weight average molecular weight of the alkali-soluble resin is preferably 5000 or more, and more preferably 10000 or more. The weight average molecular weight of the alkali-soluble resin is preferably 100000 or less, more preferably 50000 or less, from the viewpoint of improving solubility in an alkaline developer.
The weight average molecular weight can be determined by Gel Permeation Chromatography (GPC). As an example, a weight average molecular weight in terms of polystyrene was obtained by performing chromatography using Water2690 (manufactured by Watts corporation) as a GPC apparatus, PLgel, 5. mu. and MIXED-D (manufactured by Polymer Laboratories) as a column, and tetrahydrofuran as a developing solvent under conditions of a column temperature of 25 ℃, a flow rate of 1 ml/min, an RI detector, a sample injection concentration of 10 mg/ml and an injection amount of 100. mu.l.
As the alkali-soluble resin, for example, there can be mentioned: acrylic copolymer resins, maleic copolymer resins, polyester resins obtained by polycondensation, polyurethane resins, and the like. Among them, acrylic type copolymer resins are preferable in terms of developability, molecular design range, and cost.
The alkali-soluble resin is preferably 20 to 90 parts by mass, more preferably 40 to 80 parts by mass, relative to 100 parts by mass of the carbon black and/or the lactam black.
Solvent(s)
As the solvent, a known solvent used for a pigment dispersion composition for a black matrix can be used. The solvent is preferably an ester solvent, an ether ester solvent, a ketone solvent, an aromatic hydrocarbon solvent, a nitrogen-containing solvent, or the like, in terms of being capable of stably dispersing a pigment and sufficiently dissolving the basic group-containing pigment dispersant and the alkali-soluble resin. The solvents may be used alone or in combination of two or more.
As the ester solvent, there may be mentioned: methyl 2-hydroxypropionate, ethyl 2-hydroxy-2-methylpropionate, butyl 3-methyl-3-methoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, methyl 3-ethoxypropionate, ethyl ethoxyacetate, glycolate, n-amyl formate, etc. Examples of the ether solvent include: ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monoisopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, diethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol methyl ethyl ether, and the like. Examples of the ether ester solvent include: ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, and the like. Examples of the ketone solvent include: methyl isobutyl ketone, cyclohexanone, 2-heptanone, delta-butyrolactone, and the like. As the aromatic hydrocarbon solvent, for example, there may be mentioned: toluene, xylene, alkylnaphthalenes, and the like. Examples of the nitrogen-containing solvent include: n-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, and the like.
In the pigment-dispersion composition for a black matrix, the proportion of the solvent is preferably 40% by mass or more, more preferably 50% by mass or more in terms of step property, and is preferably 90% by mass or less, more preferably 80% by mass or less in terms of dispersion stability.
Pigment dispersing aid having acidic groups
The pigment-dispersion composition for a black matrix may further contain a pigment-dispersion aid having an acidic group for the purpose of further improving the dispersibility of the pigment. Examples of the pigment dispersing aid having an acidic group include: examples of the pigment include compounds obtained by neutralizing lactam black, perylene compounds, pyrrolopyrrole dione compounds, azonaphthol compounds, dioxazine compounds, quinacridone compounds, phthalocyanine compounds and metal complexes thereof, and compounds obtained by linking an acid group such as a carboxyl group or a sulfonic acid group to a pigment such as anthraquinone, naphthalene, acridone or triazine (pigment derivatives having an acid group), and compounds obtained by neutralizing the pigment with an organic amine or the like. The pigment derivative having an acidic group is preferably a phthalocyanine-based pigment derivative having a sulfonic acid group in terms of good dispersibility of carbon black. The pigment derivatives may be used alone or in combination of two or more.
The pigment dispersing aid having an acidic group is preferably 0.1 to 20 parts by mass, more preferably 1 to 10 parts by mass, per 100 parts by mass of the carbon black and/or the lactam black.
In the pigment-dispersion composition for a black matrix, the total proportion of the carbon black, the basic group-containing pigment dispersant, the alkali-soluble resin, the solvent, and the inorganic compound is preferably 70% by mass or more, more preferably 80% by mass or more, and still more preferably 90% by mass or more. Further, in the case of using a pigment dispersion aid having an acid group, in the pigment dispersion composition for a black matrix, the total proportion of the carbon black, the basic group-containing pigment dispersant, the alkali-soluble resin, the solvent, the inorganic compound, and the pigment dispersion aid having an acid group is preferably 75% by mass or more, more preferably 85% by mass or more, and still more preferably 95% by mass or more.
The pigment dispersion composition for a black matrix is prepared by dispersing the above components using a roll mill, a kneader, a high-speed stirrer, a bead mill, a ball mill, a sand mill, an ultrasonic disperser, a high-pressure dispersing device, or the like.
Pigment dispersion photoresist composition for black matrix
The pigment dispersion photoresist composition for a black matrix of the present invention includes the pigment dispersion composition for a black matrix, a photopolymerizable compound, and a photopolymerization initiator. In addition, in the solid content of the pigment dispersion resist composition for a black matrix, the proportion of the carbon black and/or the lactam black is preferably 30% by mass or more and 80% by mass or less. In addition, in the solid content of the pigment dispersion resist composition for a black matrix, the proportion of the inorganic compound is preferably 1% by mass or more and 10% by mass or less, and more preferably 1.3% by mass or more and 8% by mass or less.
Photopolymerizable compound
As the photopolymerizable compound, known photopolymerizable compounds used for a pigment dispersion resist composition for a black matrix can be used, and examples thereof include monomers and oligomers having photopolymerizable unsaturated bonds. The photopolymerizable compounds may be used alone or in combination of two or more.
Examples of the monomer having one photopolymerizable unsaturated bond include: alkyl methacrylates or alkyl acrylates such as methyl methacrylate, butyl methacrylate, 2-ethylhexyl methacrylate, methyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate; aralkyl methacrylate or aralkyl acrylate such as benzyl methacrylate and benzyl acrylate; alkoxyalkyl methacrylates or alkoxyalkyl acrylates such as butoxyethyl methacrylate and butoxyethyl acrylate; aminoalkyl methacrylates or aminoalkyl acrylates such as N, N-dimethylaminoethyl methacrylate and N, N-dimethylaminoethyl acrylate; methacrylic acid esters or acrylic acid esters of polyalkylene glycol monoalkyl ethers such as diethylene glycol monoethyl ether, triethylene glycol monobutyl ether, and dipropylene glycol monomethyl ether; methacrylic acid esters or acrylic acid esters of polyalkylene glycol monoaryl ethers such as hexaethylene glycol monophenyl ether; isobornyl methacrylate or acrylate; glycerol methacrylate or glycerol acrylate; 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate, and the like.
Examples of the monomer having two or more photopolymerizable unsaturated bonds include: bisphenol A dimethacrylate, 1, 4-butanediol dimethacrylate, 1, 3-butanediol dimethacrylate, diethylene glycol dimethacrylate, glycerol dimethacrylate, neopentyl glycol dimethacrylate, polyethylene glycol dimethacrylate, polypropylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, pentaerythritol tetramethacrylate, dipentaerythritol hexamethacrylate, dipentaerythritol pentamethylacrylate, bisphenol A diacrylate, 1, 4-butanediol diacrylate, 1, 3-butanediol diacrylate, diethylene glycol diacrylate, glycerol diacrylate, neopentyl glycol diacrylate, Polyethylene glycol diacrylate, polypropylene glycol diacrylate, tetraethylene glycol diacrylate, trimethylolpropane triacrylate, pentaerythritol tetraacrylate, dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, and the like.
Examples of the oligomer having a photopolymerizable unsaturated bond include oligomers obtained by appropriately polymerizing the above-mentioned monomers.
In the solid content of the pigment dispersion resist composition for a black matrix, the photopolymerizable compound is preferably 2 to 20% by mass, and more preferably 4 to 15% by mass.
As the photopolymerization initiator, known photopolymerization initiators used for pigment-dispersed resist compositions for black matrices can be used, and examples thereof include: benzophenone, N ' -tetraethyl-4, 4' -diaminobenzophenone, 4-methoxy-4 ' -dimethylaminobenzophenone, benzil, 2-diethoxyacetophenone, benzoin methyl ether, benzoin isobutyl ether, benzil dimethyl ketal, α -hydroxyisobutyl benzophenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, tert-butylanthraquinone, 1-chloroanthraquinone, 2, 3-dichloroanthraquinone, 3-chloro-2-methylanthraquinone, 2-ethylanthraquinone, 1, 4-naphthoquinone, 1, 2-benzoanthraquinone, 1, 4-dimethylanthraquinone, 2-phenylanthraquinone, triazine photopolymerization initiator, oxime ester photopolymerization initiator, and the like. The photopolymerization initiator may be used alone or in combination of two or more.
In the solid content of the pigment dispersion resist composition for a black matrix, the photopolymerization initiator is preferably 0.1 to 15% by mass, and more preferably 1 to 10% by mass.
The pigment dispersion photoresist composition for a black matrix may additionally add the alkali soluble resin in terms of developability of an alkali developer. Further, in the solid content of the pigment dispersion resist composition for a black matrix, the total proportion of the alkali-soluble resin is preferably 10% by mass or more and 50% by mass or less. In addition, the pigment dispersion photo-resist composition for a black matrix may additionally add the solvent in terms of improving coatability. In the pigment dispersion resist composition for a black matrix, the total proportion of the solvents is preferably 50% by mass or more, more preferably 70% by mass or more.
The pigment dispersion resist composition for a black matrix may further contain additives such as a leveling agent, an antioxidant, and a defoaming agent, as required.
The pigment dispersion resist composition for a black matrix is prepared by stirring and mixing the components of the pigment dispersion composition for a black matrix, the photopolymerizable compound, the photopolymerization initiator, and the like using a stirring device or the like.
[ examples ]
Hereinafter, the present invention will be described with reference to examples, but the present invention is not limited to these examples.
Preparation examples 1 to 8 and comparative preparation examples 1 to 3
Preparation of pigment-dispersion composition for black matrix
After mixing the respective raw materials shown in table 1 in the manner of the formulation composition (mass%) shown in table 1, milling was performed by a bead mill to prepare the pigment-dispersion compositions for black matrix of each of the preparation examples and the comparative preparation examples.
Evaluation of Dispersion stability
The respective pigment-dispersion compositions for black matrix were put into glass bottles, the caps were tightened, and the state after storage at room temperature for 7 days was evaluated according to the following evaluation criteria. And taking A as a qualified standard. The results are shown in table 1.
A: thickening and precipitation were not observed.
B: thickening or precipitation was confirmed to the extent that the gel recovered after light shaking.
C: thickening and precipitation were confirmed to such an extent that they could not be recovered even by vigorous shaking.
Examples 1 to 8 and comparative examples 1 to 3
Preparation of pigment dispersion photoresist composition for black matrix
The pigment dispersion resist compositions for black matrix of each example and comparative example were prepared by mixing the respective raw materials shown in table 2 in the formulation composition (mass%) shown in table 2 using a high speed stirrer and then filtering through a filter having a pore size of 0.5 μm.
Evaluation of recyclability (1): evaluation of adhesion of resist Pattern Using treated developer
The pigment dispersion resist compositions for black matrix described above were coated on a glass substrate (Corning1737) by a spin coater in a thickness of 1 μm and prebaked at 100 ℃ for 3 minutes. Subsequently, a photomask having a line pattern of 5 μm, 8 μm, 10 μm, 15 μm, 20 μm, 30 μm was passed through a high pressure mercury lamp at 400mJ/cm2The resist film including the exposed portion (cured portion) is produced by performing exposure with the UV integrated light amount of (b). Next, 0.05% aqueous potassium hydroxide solution (developer) was used at 23 ℃ and 0.5kgf/cm2The development was carried out for another 20 seconds from the time (development point) when the developed pattern appeared, and then the pressure was 3.0kgf/cm2Spray washing was performed under the pressure of (1). Then, by the same operation as described above, a resist film including an exposed portion (cured portion) is produced again. Using the photoresist film including the exposed portion (cured portion) prepared again and the recovered developer, the temperature was controlled at 23 ℃ and the concentration was controlled at 0.5kgf/cm2The development was carried out for another 20 seconds from the time (development point) when the developed pattern appeared, and then the development was carried out at 3.0kgf/cm2Spray washing was performed under the pressure of (1). The dimension of the minimum pattern remaining on the substrate was measured, and the reuse adhesion was evaluated according to the following evaluation criteria. Will be provided withAnd A is taken as a qualified standard. The results are shown in table 2.
A: the remaining minimum pattern sizes were 2 μm, 5 μm, and 8 μm.
B: the remaining minimum pattern size was 10 μm, 15 μm.
C: the remaining minimum pattern size was 20 μm, 30 μm.
Evaluation of recyclability (2): evaluation of developability of resist Pattern Using treated developer
The time (development point) at which the development pattern started to appear in the development process using the recovered developer in the above "evaluation of adhesion of resist pattern using treated developer" was evaluated according to the following evaluation criteria. A or B is taken as a qualification standard. The results are shown in table 2.
A: can be completely removed within 30 seconds.
B: complete removal can be achieved in more than 30 seconds and 60 seconds.
C: even more than 60 seconds, it cannot be completely removed.
Further, using the obtained pigment dispersion resist composition for a black matrix, each item was evaluated according to the following evaluation method. The results are shown in table 2.
Evaluation of optical Density (OD value) of resist Pattern
The various pigment dispersion resist compositions for black matrix were applied to a glass substrate (Corning1737) by a spin coater in a thickness of 1 μm, prebaked at 100 ℃ for 3 minutes, exposed to light by a high pressure mercury lamp, and baked at 230 ℃ for 30 minutes to obtain a resist film consisting of only a solid portion. The optical density (OD value) of the resist film in each of the solid portions thus obtained was measured by a Macbeth densitometer (trade name D-200II, manufactured by Mibeth).
Evaluation of developability of resist Pattern
The various pigment dispersion photoresist compositions for a black matrix were coated on a glass substrate (Corning1737) in a thickness of 1 μm by a spin coater, and prebaked at 100 ℃ for 3 minutes. Subsequently, a composition having a particle size of 5 μm, 8 μm, 10 μm, 15 μm, 20 μm, 30 μm was usedPhotomask of line pattern of μm, passing through high pressure mercury lamp at 400mJ/cm2The resist film is produced by exposing the resist film to the UV integrated light. Using a high-pressure mercury lamp at 400mJ/cm2The exposure is performed with the UV integrated light quantity. Next, 0.05% aqueous potassium hydroxide solution (developer) was used at 23 ℃ and 0.5kgf/cm2The time (development point) at which the development pattern starts to appear was evaluated according to the following evaluation criteria.
A: can be completely removed within 30 seconds.
B: complete removal can be achieved in more than 30 seconds and 60 seconds.
C: even more than 60 seconds, it cannot be completely removed.
Evaluation of adhesion of resist Pattern
The various pigment dispersion photoresist compositions for a black matrix were coated on a glass substrate (Corning1737) in a thickness of 1 μm by a spin coater, and prebaked at 100 ℃ for 3 minutes. Subsequently, a photomask having a pattern of 5 μm, 8 μm, 10 μm, 15 μm, 20 μm, 30 μm was passed through a high pressure mercury lamp at 400mJ/cm2The resist film is produced by exposing the resist film to the UV integrated light. Next, 0.05% aqueous potassium hydroxide solution (developer) was used at 23 ℃ and 0.5kgf/cm2The development was carried out for another 20 seconds from the time (developing point) when the developed pattern appeared, and the pressure was 3.0kgf/cm2Spray washing was performed under the pressure of (1). The size of the minimum pattern remaining on the substrate was evaluated according to the following evaluation criteria.
A: the remaining minimum pattern sizes were 2 μm, 5 μm, and 8 μm.
B: the remaining minimum pattern size was 10 μm, 15 μm.
C: the remaining minimum pattern size was 20 μm, 30 μm.
Evaluation of seal Strength
The various pigment dispersion resist compositions for black matrix were coated on a glass substrate (Corning1737) by a spin coater in a thickness of 1 μm, prebaked at 100 ℃ for 3 minutes, exposed by a high pressure mercury lamp, and baked at 230 ℃ for 30 minutes to obtain a resist film formed only of a solid portion. An aluminum pin having a diameter of 5mm was attached to the obtained substrate and a glass substrate (Corning1737) not coated with the resist composition by a predetermined amount of a sealant. Subsequently, the glass substrate to which the aluminum pin was attached was baked at 150 ℃ for 1 hour to fabricate a test piece. The obtained test piece was subjected to a tensile test, and the strength at the time of peeling was read and divided by the applied area of the sealant to obtain the strength per unit area (seal strength). Based on the sealing strength of each composition, a relative value was calculated assuming that the sealing strength of the glass not coated with the resist composition was 100, and evaluated according to the following evaluation criteria.
A: the relative value is above 80.
B: the relative value is 60 or more and 80 or less.
C: the relative value did not reach 60.
TABLE 1
TABLE 2
In tables 1 and 2, Raven1080 represents carbon black (average primary particle diameter 28nm, pH 2.4, manufactured by Columbia Chemical Co., Ltd.);
iragaphor Black S0100 CF represents lactam Black (manufactured by BASF corporation);
aluminum hydroxide represents "C301N" (average primary particle diameter 1500nm, manufactured by Sumitomo chemical Co., Ltd.);
alumina (a) represents "AKP-53" (average primary particle diameter of 180nm, manufactured by Sumitomo chemical Co., Ltd.);
alumina (b) represents "AA-03" (average primary particle diameter of 440nm, manufactured by Sumitomo chemical Co., Ltd.);
barium titanate (a) represents "BTC-4 FA" (average primary particle diameter of 200nm, manufactured by Nippon chemical industries Co., Ltd.);
barium titanate (b) represents "BTC-4 FB" (average primary particle diameter of 300nm, manufactured by Nippon chemical industries Co., Ltd.);
barium titanate (c) represents "KZM-50" (average primary particle diameter of 50nm, manufactured by Nippon chemical industries Co., Ltd.);
barium sulfate represents "BF-40" (average primary particle diameter of 10nm, made by Sakai chemical industry Co., Ltd.);
solsperse5000 represents a phthalocyanine dye derivative having a sulfonic acid group (manufactured by Lumboun Co., Ltd.);
BYK-167 represents an amino group-containing polyurethane-type polymeric dispersant having a polyester chain (manufactured by BYK-Chemie, Inc., solid content: 52% by mass);
BYK-LPN-22329 represents an amino group-containing acrylic acid-type polymeric pigment dispersant (manufactured by BYK-Chemie, Inc., solids content 58%);
BzMA/MAA represents a BzMA (benzyl methacrylate)/MAA (methacrylic acid) copolymer (acid value 100mgKOH/g, weight average molecular weight 30000);
PGMEA represents propylene glycol monomethyl ether acetate.
In table 2, DPHA represents dipentaerythritol hexaacrylate;
irgacure OXE02 represents an oxime ester photopolymerization initiator (manufactured by basf corporation, japan);
MEGAFAC F555 represents an oligomer containing a fluorine-containing group, a hydrophilic group and a lipophilic group (30% by mass in solid content, manufactured by DIC).
Claims (3)
1. A pigment-dispersion composition for a black matrix comprising carbon black and/or lactam black, a pigment-dispersing agent containing a basic group, an alkali-soluble resin, and a solvent,
further comprising at least one inorganic compound selected from the group consisting of barium titanate, aluminum oxide and aluminum hydroxide,
the inorganic compound is 30 parts by mass or less with respect to 100 parts by mass of the carbon black and/or the lactam black.
2. A pigment-dispersed photo-resist composition for a black matrix, comprising the pigment-dispersed composition for a black matrix according to claim 1, a photopolymerizable compound and a photopolymerization initiator.
3. The pigment dispersion resist composition for a black matrix according to claim 2, wherein the proportion of the inorganic compound in the solid content of the pigment dispersion resist composition for a black matrix is 1% by mass or more and 10% by mass or less.
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