KR20140148377A - Photosensitive black resin composition and resin black matrix substrate - Google Patents
Photosensitive black resin composition and resin black matrix substrate Download PDFInfo
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- KR20140148377A KR20140148377A KR1020147025452A KR20147025452A KR20140148377A KR 20140148377 A KR20140148377 A KR 20140148377A KR 1020147025452 A KR1020147025452 A KR 1020147025452A KR 20147025452 A KR20147025452 A KR 20147025452A KR 20140148377 A KR20140148377 A KR 20140148377A
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
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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
- G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
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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
- G03F7/075—Silicon-containing compounds
- G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/22—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of auxiliary dielectric or reflective layers
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- Spectroscopy & Molecular Physics (AREA)
- General Physics & Mathematics (AREA)
- Materials For Photolithography (AREA)
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Abstract
The present invention provides a black resin composition which is excellent in adhesiveness to a substrate at the time of development thereof, has good compatibility with a developer, and can be patterned with high precision, when a resin black matrix is formed on a glass substrate And to provide a resin black matrix substrate using such a photosensitive black resin composition, further, a color filter and a light-shielding film for a touch panel. The present invention relates to a photosensitive black resin composition comprising at least a light-shielding material, an alkali-soluble resin, a photopolymerization initiator and a solvent, wherein the oxetane compound having at least a specific structure is contained as an additive and the oxetane compound is mixed with a light- And 1.5 to 10.0 wt% based on the total weight of the resin.
Description
The present invention relates to a photosensitive black resin composition and a resin black matrix substrate.
Conventionally, a metal thin film using a chromium-based material has been used as a black matrix material, but in recent years, a resin black matrix containing a resin and a light-shielding material has been used in view of cost and environmental pollution. The resin black matrix is obtained by applying a black resin composition containing a light shielding material such as resin and carbon black onto a substrate and drying the black resin film to form a black coat and finely patterning the black coat by a photolithography method.
2. Description of the Related Art In recent years, miniaturization of liquid crystal display devices and contents to be displayed are diversified from characters to images, so that high performance and high precision of the color filters are required. For the resin black matrix, there are demands for high order lightness (OD value) It is getting higher. Although the high OD value and thinning can be achieved by increasing the volume ratio of the light shielding material, the resin ratio in the resin black matrix is reduced, so that the adhesion between the resin black matrix and the glass is lowered and the resin black matrix is peeled off at the time of alkali development Occurs. Therefore, there is a demand for a resin black matrix which is excellent in developing adhesion with a glass substrate and capable of patterning with high accuracy.
In addition, even in the case of a substrate for a touch panel, a light shielding film is formed as a peripheral frame. Even in the case where the volume ratio of the light shielding material is increased like the color filter, high developing adhesion and high precision pattern processing are required.
However, since the black matrix itself is light-shielding, in the photosensitive resin black matrix, photocuring due to exposure hardly occurs near the interface with the substrate. Therefore, as the light shielding property of the resin black matrix becomes higher, the adhesion to the glass substrate at the time of development deteriorates, and the light shielding property and developing adhesion property are in a trade-off relationship.
Further, since the black resin composition having a high optical density contains a large amount of inorganic particles as a pigment, compatibility with an alkaline developer is poor, and there is a problem that a fine pattern is lost at the time of development.
To solve such a problem, a tertiary amine compound, a trivalent phosphorus compound, an epoxy silane, and the like are known as additives for raising the sensitivity of the resin black matrix and causing a photopolymerization reaction to the vicinity of the interface with the substrate (see Patent Documents 1 to 3) 3). However, it has been difficult to obtain a high-precision patterning substrate.
On the other hand, in a system not containing a pigment, a photosensitive resin composition added with an oxetane compound as an additive is known (Patent Documents 4 and 5). It has also been found that, in a photosensitive resin composition containing a pigment, a cured film containing a copolymer resin containing an oxetanyl group as a structural unit is effective for physical adhesion with a substrate (Patent Document 6).
The inventors of the present invention focused attention on developing adhesiveness which is an index of the peel resistance of a fine pattern at the time of development. In the Patent Documents 1 to 3, the curing reaction at the substrate interface is insufficient for a film having a high optical density of the resin black matrix, The adhesiveness at the time of development tends to be influenced by the base substrate, and in particular, the adhesion with soda glass generally used in touch panel applications is poor, so that a high-precision patterning substrate is obtained I thought about whether or not it would become difficult.
In addition, in the case of a black resin composition having a high optical density of the resin black matrix and a large amount of pigment particles, the compatibility with the developer is more insufficient and peeling of the fine pattern occurs at the time of development. The present inventors have also taken into account compatibility.
SUMMARY OF THE INVENTION The present invention was conceived in view of such drawbacks of the prior art, and it is an object of the present invention to provide a method for producing a resin black matrix, which is excellent in adhesiveness to a substrate at the time of development, To provide a black resin composition capable of high-precision pattern processing, and to provide a resin black matrix substrate using such a photosensitive black resin composition, further, a color filter and a light-shielding film for a touch panel.
Patent Documents 4 and 5 disclose an oxetane compound, and there is a belief that the cured film after post-baking has excellent physical adhesion with the substrate and is excellent in terms of resolution and sensitivity. However, There is no knowledge, and the application to a black resin composition containing a large amount of pigment particles with high optical density of the resin black matrix is not disclosed.
On the other hand, in Patent Document 6, there is a knowledge that in the photosensitive resin composition containing a pigment, the post-baked cured film containing a resin of a copolymer containing an oxetanyl group as a structural unit is effective for physical adhesion with the substrate , There is no knowledge about adhesion to a substrate at the time of development, and there is no knowledge about compatibility with a developer, which is susceptible to being present in a black resin composition containing a large amount of pigment particles There was no.
Here, the present inventors have found that the above problems can be solved by adding an appropriate amount of a specific oxetane compound.
The object of the present invention is achieved by the following arrangement.
(1) A photosensitive black resin composition comprising at least a light-shielding material, an alkali-soluble resin, a photopolymerization initiator and a solvent, wherein the oxetane compound having at least a structure represented by the following formula (A) And 1.5 to 10.0% by weight based on the sum of the slag and the alkali-soluble resin.
(2) The photosensitive black resin composition according to the above item (1), wherein the oxetane compound has a silyl group.
(3) The photosensitive black resin composition according to the above (1) or (2), wherein the oxetane compound is represented by the following formula (B).
(4) A resin black matrix substrate obtained by applying the photosensitive black resin composition according to any one of (1) to (3) above onto a transparent substrate and patterning the same.
By using the black resin composition of the present invention, there is an effect that a resin black matrix substrate excellent in development adhesiveness and pattern processing accuracy can be obtained.
The photosensitive black resin composition of the present invention is required to contain at least a light-shielding material, an alkali-soluble resin, a photopolymerization initiator, and a solvent.
The photosensitive black resin composition of the present invention can be applied to various applications such as printing ink, ink jet ink, photomask producing material, printing proof fabrication material, etching resist, solder resist, barrier rib of a plasma display panel (PDP) Shielding images such as a wiring pattern of electronic parts, a conductive paste, a conductive film, or a black matrix (hereinafter referred to as "BM"). Preferably, in order to improve the display characteristics of the color filter used for a color liquid crystal display device or the like, in order to provide a shielding image (including the BM) on the space portion of the coloring pattern, the peripheral portion and the external light side of the TFT, It can be suitably used for a light-shielding film used for the peripheral portion.
Particularly preferably, a black frame provided on the periphery of a display device including a liquid crystal display device, a plasma display device, an EL display device with inorganic EL, a CRT display device, and a touch panel, or a coloring of red, A lattice image between pixels or a black portion on a stripe, more preferably a BM on a dot-like or line-shaped black pattern for TFT shielding.
Examples of the light shielding material to be used in the present invention include black pigments such as carbon black, titanium black, chromium oxide, iron oxide, aniline black, perylene pigments or CI solvent black 123, carbon black coated with a resin, A composite black oxide such as iron, copper or cobalt, or a combination of an organic pigment and a black pigment, but carbon black or titanium nitride is preferable because of high light shielding property.
Examples of the alkali-soluble resin to be used in the present invention include an epoxy resin, an acrylic resin, a siloxane polymer-based resin or a polyimide resin, but an acrylic resin or a polyimide resin excellent in storage stability of the composition and heat resistance of a coating film is preferable Do.
As the acrylic resin, an acrylic resin having a carboxyl group is preferably used. As the acrylic resin having a carboxyl group, a copolymer of an unsaturated carboxylic acid and an ethylenically unsaturated compound is preferable. Examples of the unsaturated carboxylic acid include acrylic acid, methacrylic acid, itaconic acid, crotonic acid, maleic acid, fumaric acid and vinylacetic acid. These may be used alone or in combination with other copolymerizable ethylenically unsaturated compounds.
Examples of the copolymerizable ethylenically unsaturated compound include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-propyl acrylate, isopropyl acrylate, n-propyl methacrylate, isopropyl methacrylate, butyl acrylate, n-butyl methacrylate, sec-butyl acrylate, sec-butyl methacrylate, iso-butyl acrylate, isobutyl methacrylate, tert-butyl acrylate, tert- butyl methacrylate, n- Unsaturated carboxylic acid alkyl esters such as pentyl, n-pentyl methacrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, benzyl acrylate or benzyl methacrylate, aromatic vinyl compounds such as o-methylstyrene, m-methylstyrene or? -methylstyrene, aminoalkyl esters of unsaturated carboxylic acids such as aminoethyl acrylate, glycidyl acrylate or Unsaturated carboxylic acid glycidyl esters such as glycidyl methacrylate, glycidyl methacrylate and the like, carboxylic acid vinyl esters such as vinyl acetate and vinyl propionate, vinyl cyanide compounds such as acrylonitrile, methacrylonitrile and? -Chloroacrylonitrile, Aliphatic conjugated dienes such as 1,3-butadiene or isoprene, polystyrene, polymethyl acrylate, polymethyl methacrylate, polybutyl acrylate or polybutyl methacrylate having acryloyl groups or methacryloyl groups at the ends, But it is preferably a 2 to 4-membered copolymer selected from the group consisting of methacrylic acid, acrylic acid, methyl methacrylate, 2-hydroxyethyl methacrylate, benzyl methacrylate and styrene and having an average molecular weight (Mw) A polymer having an acid value of 70 to 150 (mg KOH / g) is preferred from the viewpoint of solubility in an alkali developing solution. Outside this range, the dissolution rate with respect to the alkali developer is lowered or becomes excessively fast.
The use of an acrylic resin having an ethylenic unsaturated group in the side chain is preferable because sensitivity at the time of exposure and development becomes good. As the ethylenic unsaturated group, an acrylic group or a methacrylic group is preferable. Such an acrylic resin can be obtained by addition reaction of an ethylenically unsaturated compound having a glycidyl group or an alicyclic epoxy group to a carboxyl group of an acrylic (co) polymer having a carboxyl group.
Examples of the acrylic resin having an ethylenic unsaturated group in the side chain include an acrylic resin described in known documents (Japanese Patent No. 3120476 and Japanese Patent Application Laid-open No. 8-262221) or a commercially available acrylic resin Resin "CYCHOLMA (registered trademark) P" (available from Daicel Chemical Industries, Ltd.) or an alkali-soluble cardo resin. Among them, an acrylic resin having an ethylenically unsaturated group in its side chain and having an average molecular weight (Mw) of 2,000 to 100,000 (measured by gel permeation chromatography as a carrier and converted to a calibration curve by standard polystyrene) , And an acid value of from 70 to 150 (mgKOH / g) are preferable from the standpoints of photosensitivity, solubility in ester solvents and solubility in alkaline developers.
A monomer may further be added to the photosensitive black resin composition of the present invention. As the monomer, for example, a polyfunctional or monofunctional acrylic monomer or oligomer can be mentioned. Examples of the polyfunctional acrylic monomer include bisphenol A diglycidyl ether (meth) acrylate, poly (meth) acrylate carbamate, modified bisphenol A epoxy (meth) acrylate, (Meth) acrylic acid esters such as hexanediol (meth) acrylate, propyl anhydride (meth) acrylate, trimellitic acid diethylene glycol (meth) acrylate, rosin modified epoxy di (meth) Fluorene diacrylate oligomers described in the literature (Japanese Patent No. 3621533 and Japanese Patent Application Laid-Open No. 8-278630), tripropylene glycol di (meth) acrylate, 1,6-hexanediol di (Meth) acrylate, bisphenol A diglycidyl ether di (meth) acrylate, trimethylol propane tri (meth) acrylate, pentaerythritol tri (Meth) acrylate, tripentaerythritol tetra (meth) acrylate, dipentaerythritol hexa (meth) acrylate, dipentaerythritol penta (meth) acrylate, 2,2-bis [4- (3-acryloxy-2-hydroxypropoxy) phenyl] propane, bis [4- Phenyl] sulfone, bis [4- (3-acryloxy-2-hydroxypropoxy) phenyl] ether, 4,4'- Phenyl] fluorene, 9,9-bis [3-methyl-4- (3-acryloxy-2-hydroxyphenyl) (3-chloro-4- (3-acryloxy-2-hydroxypropoxy) phenyl] fluorene, bisphenoxyethanol fluorene diacrylate, Bisphenoxyethanol fluorene dimethacrylate, biscresol fluorene diacrylate Or biscaleol fluorene dimethacrylate. These may be used alone or in combination.
Depending on the selection and combination of these polyfunctional or monofunctional acrylic monomers or oligomers, it is possible to control the sensitivity and processability characteristics of the resist. Particularly, in order to increase the sensitivity, a compound having three or more functional groups is preferable, a compound having five or more functional groups is more preferable, and dipentaerythritol hexa (meth) acrylate or dipentaerythritol penta (meth) More preferable.
In the case of using a pigment that absorbs ultraviolet light which is effective for photo-crosslinking, such as a black pigment, it is preferable that the pigment contains a large amount of aromatic rings in addition to dipentaerythritol hexa (meth) acrylate or dipentaerythritol penta (meth) It is preferable to use (meth) acrylate having a fluorine ring having a high water-repellency in combination because the pattern can be controlled in a desired shape at the time of development. Among them, a mixture of 10 to 60 parts by weight of dipentaerythritol hexa (meth) acrylate and / or dipentaerythritol penta (meth) acrylate and 90 to 40 parts by weight of a (meth) acrylate having a fluorene ring It is preferably used as a monomer.
Examples of the photopolymerization initiator include a benzophenone compound, an acetophenone compound, a thioxanone compound, an imidazole compound, a benzothiazole compound, a benzoxazole compound, an oxime ester compound, a carbazole compound, , Phosphorus compounds, titanates, and other inorganic photopolymerization initiators.
More specifically, examples thereof include benzophenone, N, N'-tetraethyl-4,4'-diaminobenzophenone, 4-methoxy-4'-dimethylaminobenzophenone, 2,2-diethoxyacetophenone , Benzoin methyl ether, benzoin isobutyl ether, benzyl dimethyl ketal,? -Hydroxyisobutyl phenone, thioxanthone, 2-chlorothioxanthone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl Benzyl-2-dimethylamino-l- (4-morpholinyl) -1- [4- (methylthio) phenyl] (Dimethylamino) -2 - [(4-methylphenyl) methyl] -1- [2-methylphenyl] -butanone (manufactured by Ciba Specialty Chemicals, Inc.) and "Irgacure (registered trademark) 2- (4-methylphenyl) -1-butanone (Ciba Specialty Chemicals), CGI-113 2- -Morpholinophenyl) -butanone (manufactured by Ciba Specialty Chemicals), t-butyl anthraquinone, 1-chloroanthraquinone, 2,3 -Dichloroanthraquinone, 3-chloro-2-methyl anthraquinone, 2-ethyl anthraquinone, 1,4-naphthoquinone, 9,10-phenanthraquinone, Anthraquinone, 2-phenylanthraquinone, 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 2- mercaptobenzothiazole, 2- mercaptobenzoxazole, (Registered trademark) OXE01, 1,2-octanedione, 1- [4- (phenylthio) -2- (O-benzoyloxime)] (manufactured by Ciba Specialty Chemicals Co., (0-acetyloxime), < / RTI > CGI-242 < RTI ID = 0.0 > (9-ethyl-6- (2-methylbenzoyl) -9H-carbazol-3-yl] -, 1- (O- acetyloxime), 4- (p- methoxyphenyl) (Trichloromethyl) -s-triazine (manufactured by Ciba Specialty Chemicals) or carbazole-based compounds "Adeka (registered trademark) Optoma" N-1818, N-1919 or " Deca (registered trademark) cruise "NCI-831 (above, Asahi Denka Manufactured by Takara Shuzo Co., Ltd.).
These photopolymerization initiators may be used in combination of two or more. Among them, "Irgacure (registered trademark)" 379, "Irgacure (registered trademark)" OXE02, "Adeka (registered trademark) Optoma" N-1919 And "ADEKA (registered trademark) Cruz" NCI-831 are used in combination, a photosensitive black resin composition having a high sensitivity and a good pattern shape can be obtained.
In addition, an adhesion improver may be added for the purpose of improving adhesion with an inorganic material such as a glass plate or a silicon wafer. As the adhesion improver, for example, a silane coupling agent or a titanium coupling agent can be used. The addition amount of the adhesion improver is usually about 0.2 to 20% by weight based on the weight of the polyimide resin or the acrylic resin.
Further, in the photosensitive black resin composition of the present invention, a polymer dispersant may be added for the purpose of improving the dispersion stability of the light shielding material. Examples of the polymer dispersant include a polyethyleneimine-based polymer dispersant, a polyurethane-based polymer dispersant, and a polyallyl amine-based polymer dispersant. These polymer dispersants are preferably added to such an extent that they do not deteriorate the photosensitivity and the adhesiveness, and the addition amount thereof is usually about 1 to 40% by weight with respect to the light shielding material.
In the photosensitive black resin composition of the present invention, the weight composition ratio of the light shielding material / resin component is preferably in the range of 80/20 to 40/60, more preferably in the range of 75/25 to 50/50, More preferable in terms of balance of values. Here, the resin component is the sum of the polymer, the monomer, the oligomer and the polymer dispersant. If the amount of the resin component is too small, the adhesion of the black coating to the substrate becomes poor. Conversely, if the amount of the light shielding material is too small, the optical density per layer (OD value / 탆) becomes low.
As the solvent used in the black resin composition of the present invention, water or an organic solvent may be used in accordance with the dispersion stability of the dispersed pigment and the solubility of the resin to be added. Examples of the organic solvent include esters, aliphatic alcohols, (poly) alkylene glycol ether solvents, ketones, amide polar solvents and lactone polar solvents, and these two or more mixed solvents are also preferable. Mixing with other organic solvents is also preferable.
As the alkali-soluble resin, an organic solvent which dissolves the acrylic resin is preferable as the organic solvent in view of the use of an acrylic resin. More specifically, for example, benzyl acetate (boiling point 214 占 폚), ethyl benzoate (boiling point 213 占 폚), methyl benzoate (boiling point 200 占 폚), diethyl malonate (boiling point 199 占 폚), 2-ethylhexyl acetate 199 ° C), propyleneglycol monoethyl ether acetate (boiling point 188 ° C), diethyl oxalate (boiling point 185 ° C), ethyl acetoacetate (boiling point 181 ° C), cyclohexyl acetate Butyl acetate (boiling point 174 占 폚), 3-methoxy-butyl acetate (boiling point 173 占 폚), methyl acetoacetate (boiling point 172 占 폚), ethyl 3-ethoxypropionate Propylene glycol monomethyl ether propionate (boiling point 160 占 폚), propylene glycol monoethyl ether acetate (boiling point 158 占 폚), pentyl acetate (boiling point 150 占 폚) or propylene glycol Monomethyl ether acetate (boiling point 146 DEG C) The can.
Examples of the solvent other than the above solvents include ethylene glycol monomethyl ether (boiling point 124 占 폚), ethylene glycol monoethyl ether (boiling point 135 占 폚), propylene glycol monoethyl ether (boiling point 133 占 폚), diethylene glycol monomethyl ether (Boiling point: 193 DEG C), monoethyl ether (boiling point: 135 DEG C), methyl carbitol (boiling point: 194 DEG C), ethyl carbitol (202 DEG C), propylene glycol monomethyl ether (Poly) alkylene glycol ether solvent such as propylene glycol tertiary butyl ether (boiling point 153 占 폚) or dipropylene glycol monomethyl ether (boiling point 188 占 폚), ethyl acetate (boiling point 77 占 폚), butyl acetate (Boiling point 126 占 폚) or isopentyl acetate (boiling point 142 占 폚), butanol (boiling point 118 占 폚), 3-methyl-2-butanol (boiling point 112 占 폚) or 3-methyl-3-methoxybutanol 174 ° C), and other aliphatic alcohols such as cyclopentanone (Boiling point: 144 占 폚), ethylbenzene (boiling point: 136 占 폚), or solvent naphtha (petroleum oil: boiling point: 165 to 178 占 폚).
Since the application by the die coating apparatus is mainstream as the size of the substrate becomes larger, a mixed solvent of two or more components is preferable in order to achieve appropriate volatility and dryness. When the boiling points of all the solvents constituting the mixed solvent are 150 ° C or lower, film thickness uniformity can not be obtained, the film thickness of the coating completion portion becomes thick, and aggregation of pigment is generated in the claw portion for discharging the coating liquid from the slit And there arise many problems that streaks occur in the coating film. On the other hand, when the mixed solvent contains a large amount of a solvent having a boiling point of 200 ° C or higher, the surface of the coating film becomes tacky and sticking occurs. Therefore, a mixed solvent containing 30 to 75 wt% of a solvent having a boiling point of 150 to 200 DEG C is preferable.
The oxetane compound as an additive in the present invention has a structure represented by the following formula (A).
(Wherein R 1 and R 2 may be the same or different, R 1 is hydrogen or an alkyl group having 1 to 10 carbon atoms, the alkyl group may further have a substituent, and R 2 is hydrogen, An alkyl group having 1 to 10 carbon atoms, and the silyl group and the alkyl group may further have a substituent)
In the above formula (A), when the alkyl group further has a substituent, for example, an alkoxy group, an acryloyl group, an acetoxy group or a silyl group can be exemplified. When R 2 is an alkyl group having 1 to 10 carbon atoms , And R 2 preferably includes an oxetanyl group. When the silyl group further has a substituent, for example, an alkyl group, an alkoxy group, an acryloyl group or an acetoxy group can be exemplified, and it is preferable that they contain an oxetanyl group.
Further, in order to sufficiently obtain the effect of the invention, it is preferable that R 2 has a silyl group, and an oxetane compound represented by the following formula (B) is more preferable.
(Wherein X represents the following oxetane compound, and n represents a natural number of 10 or less)
(Wherein * represents a linking moiety, R 1 represents hydrogen or an alkyl group having 1 to 10 carbon atoms, and the alkyl group may further have a substituent)
Of the oxetane compounds represented by the above formula (B), oxetane compounds with n = 3 to 6 are preferred. In the above formula (B), examples of the substituent in the case where the alkyl group further has a substituent include an alkoxy group, an acryloyl group and an acetoxy group.
The amount of these oxetane compounds to be added is preferably from 1.5 to 10.0% by weight based on the sum of the light-shielding material and the alkali-soluble resin, more preferably from 1.5 to 5.0% by weight for use in a range where the solubility in an alkali developing solution is not excessively increased Do.
Examples of the oxetane compound having no silicon atom include "Alonoxetane (registered trademark)" OXT-101 (3-ethyl-3-hydroxymethyloxetane) represented by the following formula (C) OXT-221 (3-ethyl-3 {[(3-ethyloxetan-3-yl) methoxy} methyl} oxetane) or "Aronoxetane (registered trademark) "OXT-121" (trade name, manufactured by Toa Kosei Co., Ltd.), "Eteracol (registered trademark)", which is a main component 1,4-bis [ OXBP (bis [(3-ethyl-3-oxetanyl) methyl] biphenyl-4,4'-dicarboxylate) or " Methyl] terephthalate) (manufactured by Ube Gosan Co., Ltd.).
As the oxetane compound having a silyl group, for example, "Aronoxetane (registered trademark) OXT-191 (3-ethyl (meth) acrylate) represented by the following formula (E) (Condensation reaction product of oxetane-3-ylmethanol and silane tetraol polycondensate, manufactured by Toagosei Co., Ltd.), oxetane compound having a silsesquioxane structure represented by the following formula (F1) or (F2) (O-SQ TX-100 or SI-20; available from Doagosei Co., Ltd.), "Aronoxetane (registered trademark)" TMSOX (Oxetan-3-yl) methyltrimethoxysilane, (oxetan-3-yl) methyl (oxetanyl) [(Oxetan-3-yl) methyl] methyldiethoxysilane, [(oxetan-3-yl) methyl] methyldimethoxysilane, , [(Oxetan-3-yl) methyl] methyldiacetoxysilane, [(oxetane- [(Oxetane-3-yl) methyl] ethyl] decylacetoxysilane, [ (Oxetan-3-yl) methyl] phenyldiacetoxysilane, [(oxetane-3-yl) methyl] phenyldiethoxysilane, (Oxetan-3-yl) methyl] diacetoxysilane, di [(oxetan-3-yl) methyl] diethoxysilane, (Oxetan-3-yl) methyl] methylacetoxysilane, di [(oxetan-3-yl) (Oxetan-3-yl) methyl] ethylacetoxysilane, di [(oxetan-3-yl) (Oxetan-3-yl) methyl] phenylacetoxysilane, tri [(oxetan-3-yl) methyl] phenylethoxysilane, Yl) methyl] methoxy silane, tri [(oxetan-3-yl) methyl] ethoxy Siloxane or tri [(oxetan-3-yl) methyl] acetoxysilane. In the present invention, a mixture of two or more of these oxetane compounds can be used.
In addition, a surfactant may be added to the photosensitive black resin composition of the present invention in order to improve the coatability and the smoothness of the colored coating while preventing the benard cell. The amount of the surfactant to be added is preferably 0.001 to 10% by weight, more preferably 0.01 to 1% by weight, based on the pigment. If the addition amount is too small, there is no effect of improving the coatability and the smoothness of the colored coating and the effect of preventing the Bernard cell, and if it is excessively large, the physical properties of the coating film may be inferior. Examples of the surfactant include anionic surfactants such as ammonium lauryl sulfate or triethanolamine polyoxyethylene alkyl ether sulfate, cationic surfactants such as stearylamine acetate or lauryltrimethylammonium chloride, lauryldimethylamine oxide or lauryldimethylamine oxide Polyoxyethylene lauryl ether, polyoxyethylene stearyl ether, sorbitan monostearate, and the like, polydimethylsiloxane and the like, and a surfactant such as carboxymethylhydroxyethylimidazolium betaine, Based surfactant or a fluorine-based surfactant. In the present invention, one or more of these surfactants may be used.
The solid content concentration of the resin component (including additives such as monomers, oligomers, and photopolymerization initiators) in the photosensitive black resin composition of the present invention and the light shielding material is preferably from 2 to 30%, more preferably from 5 to 30% To 20% is more preferable. Therefore, the photosensitive black resin composition of the present invention is preferably essentially composed of a solvent, a resin component and a light shielding material, more preferably a total amount of the resin component and the light shielding material is 2 to 30%, more preferably 5 to 20% Do. The remainder portion excluding the solid content is a solvent and may further contain a surfactant as described above.
Examples of the method for producing the photosensitive black resin composition in the present invention include a method in which a pigment is dispersed directly in a resin solution using a dispersing machine or a method in which a pigment is dispersed in water or an organic solvent using a dispersing machine, Followed by mixing with a resin solution. As the dispersing method of the pigment, for example, a ball mill, a sand grinder, a three-roll mill or a high-speed impact mill can be mentioned, and a bead mill is preferable from the viewpoints of dispersion efficiency and fine particle oxidation. As the beads mill, for example, a coball mill, a basket mill, a pin mill or a dyno mill may be used. As the beads of the bead mill, for example, titania beads, zirconia beads or zircon beads can be mentioned. The bead diameter used for dispersion is preferably 0.01 to 5.0 mm, more preferably 0.03 to 1.0 mm. When the primary particle diameter of the pigment and the particle diameter of the secondary particles formed by agglomeration of the primary particles are small, it is preferable to use minute dispersing beads such as 0.03 to 0.10 mm. In this case, it is preferable to disperse by using a bead mill having a separator by a centrifugal separation method capable of separating the minute dispersion beads from the dispersion. On the other hand, when dispersing pigments containing coarse particles of the submicrometer size, it is preferable to use dispersion beads of 0.10 mm or more to obtain a sufficient crushing power to finely disperse the pigments.
Production examples of the resin BM substrate of the present invention are shown below. Examples of the method of applying the photosensitive black resin composition on a transparent substrate include a dipping method, a roll coater method, a spinner method, a die coating method, a method using a wire bar, a method of immersing a transparent substrate in a solution of a photosensitive black resin composition, And a method of spraying a solution of the photosensitive black resin composition onto a transparent substrate. Examples of the transparent substrate include films or sheets of inorganic glass or organic plastic such as quartz glass, borosilicate glass, aluminosilicate glass or soda lime glass whose surface is coated with silica. When the coating is carried out on a substrate, the adhesion between the BM coating and the substrate can be improved by treating the surface of the substrate with an adhesion aid such as a silane coupling agent, an aluminum chelating agent or a titanium chelating agent.
The photosensitive black resin composition is coated on a transparent substrate, followed by heat drying and curing by air drying, heat drying or vacuum drying or the like to form a dried film. It is preferable to dry the transparent substrate coated with the coating liquid under reduced pressure by a reduced pressure dryer equipped with a heating device, and then heat dry and cure in order to suppress drying unevenness or conveying unevenness when the film is formed.
The dried coating thus obtained is patterned by a method such as photolithography. The dried film obtained from the photosensitive resin may be subjected to exposure and then to a desired pattern as it is or after forming an oxygen barrier film on its surface. Thereafter, if necessary, the oxygen shielding film is removed, and the resultant is heated and cured to obtain a resin BM substrate. The heating and curing conditions vary depending on the resin, but when an acrylic resin is used, heating is generally carried out at 200 to 250 ° C for 1 to 60 minutes.
The color filter substrate for a liquid crystal display or the light-shielding film for a touch panel can be manufactured using the resin BM substrate of the present invention. That is, the present invention can provide a color filter substrate for a liquid crystal display and a light-shielding film for a touch panel comprising the resin BM substrate of the present invention. The color filter is a color filter including at least a resin BM substrate on which a resin BM is formed on a partial region of a transparent substrate and a pixel formed on a region where a resin BM on a transparent substrate is not formed, Is a resin BM substrate.
<Examples>
Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto.
Example 1
(Manufactured by Nisshin Engineering Co., Ltd.) (400 g) produced by a thermal plasma method was subjected to a thermal treatment by a method described in a publicly known document (Japanese Patent No. 3120476) as an acrylic resin, using methyl methacrylate / methacrylic acid / (MW) of 15,000 and an acid value of 110 (mgKOH / g) were obtained by adding 40 parts by weight of glycidyl methacrylate, re-precipitating with purified water, filtering and drying, Of an acrylic resin (P-1). (187.5 g) of a 40 wt% solution of propylene glycol monomethyl ether acetate, 62.5 g of a polymer dispersant (BYK21116; manufactured by Big Chemical) and 890 g of propylene glycol monoethyl ether acetate were added to a tank And the mixture was stirred with a homomixer (manufactured by Tokushu Kika Kogyo Co., Ltd.) for 1 hour to obtain a preliminary dispersion liquid 1. Thereafter, the preliminary dispersion 1 was supplied to an Ultra Apex mill (manufactured by Gotobu Kogyo Co., Ltd.) equipped with a centrifugal separator filled with 70% of 0.10 mm phi zirconia beads (manufactured by Toray Industries, Inc.) and dispersed at a rotation speed of 8 m / s for 2 hours , A solid content concentration of 25% by weight, and a pigment / resin (weight ratio) = 80/20.
40 wt% solution (187.5 g) of propylene glycol monomethyl ether acetate in an acrylic resin (P-1), polymer dispersant (BYK21116, 62.5 g) and propylene glycol monoethyl Ether acetate (890 g) was charged into the tank and stirred with a homomixer for 1 hour to obtain a preliminary dispersion 2. Thereafter, the preliminary dispersion 2 was supplied to an Ultra Apex mill equipped with a centrifugal separator filled with 70% zirconia beads of 0.10 mm phi and dispersed for 2 hours at a rotation speed of 8 m / s to obtain a pigment dispersion having a solid content concentration of 20% by weight, To obtain a carbon black pigment dispersion CB-1 having a weight ratio (weight ratio) = 80/20.
"ADEKA (registered trademark) Cruz" NCI-831 (1.69 g) as a photopolymerization initiator was added to propylene glycol monoethyl ether acetate (14.31 g), and the mixture was stirred until the solids were dissolved.
Further, a 40 wt% solution (5.50 g) of propylene glycol monomethyl ether acetate in the acrylic polymer (P-1), and propylene glycol monoethyl (2-ethylhexyl acrylate) as a polyfunctional monomer in dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Propylene glycol monoethyl ether acetate of an oxetane compound "Aronoxetane" OXT-191 (hereinafter referred to as " oxetane compound 1 ", manufactured by Toagosei Co., Ltd.) as a contact improving agent, 0.41 g of a 50 wt% solution, 0.41 g of KBM5103 (Shin-Etsu Chemical Co., Ltd.) and a 10 wt% solution (0.24 g) of a silicone surfactant BYK333 as a surfactant in propylene glycol monoethyl ether acetate were added, For 1 hour to obtain a photosensitive resist. 13.93 g of the pigment dispersion 1 and 19.90 g of the pigment dispersion 2 were added to the photosensitive resist to obtain a photosensitive black resin composition 1 having a total solid content concentration of 23% and a pigment / resin (weight ratio) = 46/54.
The photosensitive black resin composition 1 thus prepared was filtered with a filter made of Teflon (registered trademark) of 2 탆 and then coated on a soda glass substrate to a thickness of 1 탆 (after post-baking) by spin coating (1H-DS; The coated substrate was heat-treated for 2 minutes by a pin-shaped projection on a hot plate at 90 DEG C, and the substrate was placed directly on a hot plate for 2 minutes to perform prebaking. Ultraviolet rays were exposed to the coating film through a resolution test mask at an exposure dose of 200 mJ / cm 2 using a mask aligner (PEM-6M, Union Kogaku Co., Ltd.).
Subsequently, the substrate was developed with an alkali developing solution of a 0.1 wt% TMAH aqueous solution, and then purified water was washed to obtain a patterned substrate. The obtained patterning substrate was held in a hot air oven at 230 캜 for 30 minutes and post baked to obtain a resin BM substrate 1.
Example 2
Except that OX-SQ TX-100 (hereinafter referred to as "oxetane compound 2"; manufactured by Toagose Corporation), which is an oxetane compound having a silsesquioxane structure, was used instead of oxetane compound 1 as the adhesion improver to be used The photosensitive black resin composition 2 was obtained in the same manner as in Example 1. Using the photosensitive black resin composition 2, a resin BM substrate 2 was obtained in the same manner as in Example 1. [
Example 3
Except that OX-SQ SI-20 (hereinafter referred to as "oxetane compound 3", manufactured by Toagose Corporation), which is an oxetane compound having a silsesquioxane structure, was used instead of the oxetane compound 1 as the adhesion improver to be used The photosensitive black resin composition 3 was obtained in the same manner as in Example 1. Using the photosensitive black resin composition 3, a resin BM substrate 3 was obtained in the same manner as in Example 1.
Example 4
Except that "Alonoxetane (registered trademark)" TMSOX (hereinafter referred to as "oxetane compound 4", manufactured by Toagosei Co., Ltd.) was used in place of the oxetane compound 1 as the adhesion improver to be used, Thereby obtaining a resin composition 4. Using the photosensitive black resin composition 4, a resin BM substrate 4 was obtained in the same manner as in Example 1.
Example 5
(Hereinafter referred to as " oxetane compound 5 ", manufactured by Toagosei Co., Ltd.) was used instead of oxetane compound 1 as the adhesion improver used in Example 1 Thereby obtaining a photosensitive black resin composition 5. Using the photosensitive black resin composition 5, a resin BM substrate 5 was obtained in the same manner as in Example 1.
Example 6
(Hereinafter referred to as " oxetane compound 6 ", manufactured by Toagose Corporation) was used instead of the oxetane compound 1 as the adhesion improver used in Example 1 Photosensitive black resin composition 6 was obtained. Using the photosensitive black resin composition 6, a resin BM substrate 6 was obtained in the same manner as in Example 1.
Example 7
A photosensitive black resin composition 7 was obtained in the same manner as in Example 1, except that the addition amount of the oxetane compound 1 was set to 3.0% as the adhesion improver to be used. Using the photosensitive black resin composition 7, a resin BM substrate 7 was obtained in the same manner as in Example 1.
Example 8
A photosensitive black resin composition 8 was obtained in the same manner as in Example 1 except that the addition amount of the oxetane compound 1 was 5.0% as a contact improver to be used. Using the photosensitive black resin composition 8, a resin BM substrate 8 was obtained in the same manner as in Example 1.
Example 9
A photosensitive black resin composition 9 was obtained in the same manner as in Example 1 except that the addition amount of the oxetane compound 1 was changed to 7.0% as a contact improving agent to be used. Using the photosensitive black resin composition 9, a resin BM substrate 9 was obtained in the same manner as in Example 1.
Example 10
A photosensitive black resin composition 10 was obtained in the same manner as in Example 1 except that the addition amount of the oxetane compound 1 was changed to 10.0% as a contact improver to be used. Using the photosensitive black resin composition 10, a resin BM substrate 10 was obtained in the same manner as in Example 1.
Example 11
"Adeka (registered trademark) Cruz" NCI-831 (1.69 g) as a photopolymerization initiator was added to propylene glycol monoethyl ether acetate (19.05 g) and stirred until solids dissolved. In addition, a 40 wt% solution (6.73 g) of propylene glycol monomethyl ether acetate of the acrylic polymer (P-1), and propylene glycol monoethyl ether of dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) as a polyfunctional monomer A 50 wt% solution of propylene glycol monoethyl ether acetate (0.41 g) of OXT-191 (manufactured by Toa Kosei K.K.) as an adhesion improver, (0.24 g) of propylene glycol monoethyl ether acetate of silicone type surfactant BYK333 as a surfactant was added and stirred at room temperature for 1 hour to obtain a photosensitive resist. 27.84 g of the above titanium black pigment dispersion TB-1 was added to this photosensitive resist to prepare a photosensitive black resin composition 11 having a total solid content concentration of 23% and a pigment / resin (weight ratio) = 46/54. Using the photosensitive black resin composition 11, a resin BM substrate 11 was obtained in the same manner as in Example 1.
Example 12
"Adeka (registered trademark) Cruz" NCI-831 (1.69 g) as a photopolymerization initiator was added to propylene glycol monoethyl ether acetate (9.57 g), and the mixture was stirred until the solids were dissolved. In addition, a solution (4.28 g) of a 40 wt% solution of propylene glycol monomethyl ether acetate in an acrylic resin (P-1), and propylene glycol monoethyl ether of dipentaerythritol hexaacrylate (manufactured by Nippon Kayaku Co., Ltd.) (0.41 g), KBM5103 (0.41 g) and propylene glycol monoethyl ether acetate of OXT-191 (manufactured by Toa Kosei Kogyo Co., Ltd.) as an adhesion improver were added to a 50 wt% A 10 wt% solution (0.24 g) of a silicone surfactant BYK333 as a surfactant was added and stirred at room temperature for 1 hour to obtain a photosensitive resist. 19.9 g of carbon black pigment dispersion CB-1 was added to this photosensitive resist to prepare a photosensitive black resin composition 12 having a total solid content concentration of 23% and a pigment / resin (weight ratio) = 46/54. Using the photosensitive black resin composition 12, a resin BM substrate 12 was obtained in the same manner as in Example 1.
Comparative Example 1
A photosensitive black resin composition 13 was obtained in the same manner as in Example 1 except that tetramethyl orthosilicate was used in place of the oxetane compound 1 as the adhesion improver to be used. Using the photosensitive black resin composition 13, a resin BM substrate 13 was obtained in the same manner as in Example 1.
Comparative Example 2
A photosensitive black resin composition 14 was obtained in the same manner as in Example 1 except that the oxetane compound was not added as the adhesion improver to be used. Further, using the photosensitive black resin composition 14, a resin BM substrate 14 was obtained in the same manner as in Example 1.
Comparative Example 3
A photosensitive black resin composition 15 was obtained in the same manner as in Example 1 except that the addition amount of the oxetane compound 1 was set to 0.5% as a contact improving agent to be used. Using the photosensitive black resin composition 15, a resin BM substrate 15 was obtained in the same manner as in Example 1.
Comparative Example 4
A photosensitive black resin composition 16 was obtained in the same manner as in Example 1 except that the addition amount of the oxetane compound 1 was changed to 13.0% as a contact improver to be used. Using the photosensitive black resin composition 16, a resin BM substrate 16 was obtained in the same manner as in Example 1. The obtained resin BM substrate 16 was evaluated for pattern shape, developing adhesiveness, and OD value by the following method. The results are shown in Table 1.
[Developing adhesive property]
Resin BM having different linewidths was formed in the same manner as in the above method, and judgment was made visually whether or not pattern peeling or defect occurred in each line width. The evaluation was made as follows:?: No defect and no peeling, and?: Defect and peeling.
[Pattern linearity]
The linearity of the pattern processing portion was evaluated using BH-C1410 (manufactured by Olympus Corporation). As for the judgment, it was rated?,? When the linearity was good, and?, X depending on the degree of the meandering or the defect of the shape end.
[OD value]
X-ray 361T (visual) The X-rite 361T (visual) densitometer was used to obtain the value from the following relationship.
OD value = log10 (I 0 / I)
Here, I 0 is the incident light intensity, and I is the transmitted light intensity. Further, since the OD value is proportional to the film thickness and the magnitude of the light shielding property is proportional to the film thickness, the OD value per 1.0 mu m is shown in the present invention.
Regarding the results shown in Table 1, the addition of an oxetane compound as an adhesion improver shows an improvement in pattern linearity regardless of the kinds of substituents on the side chain. Further, by adding oxetane containing a silyl group, a photosensitive black resin composition excellent in both development adhesiveness and pattern linearity was obtained.
When the addition amount of the oxetane compound is set to 1.5% or less or 10.0% or more based on the solid content of the paste, the result is deteriorated with respect to the development adhesion property, and the appropriate addition amount is 1.5 to 10.0%.
As the comparative example 1, tetramethyl orthosilicate having no oxetane ring but only a silyl group was added. However, the development adhesiveness and the pattern linearity were not improved, and the oxetane compound having a silyl group, which is a requirement of the present invention, Resulting in improvement in developability and pattern linearity of the resin composition.
Claims (4)
Wherein R 1 and R 2 may be the same or different, R 1 is hydrogen or an alkyl group having 1 to 10 carbon atoms, the alkyl group may further have a substituent, R 2 is a hydrogen atom, a silyl group Or an alkyl group having 1 to 10 carbon atoms, and the silyl group and the alkyl group may further have a substituent)
(Wherein X represents the following oxetane compound, and n represents a natural number of 10 or less)
(Wherein * represents a linking moiety, R 1 represents hydrogen or an alkyl group having 1 to 10 carbon atoms, and the alkyl group may further have a substituent)
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| JP2012068902 | 2012-03-26 | ||
| JPJP-P-2012-068902 | 2012-03-26 | ||
| PCT/JP2013/056437 WO2013146183A1 (en) | 2012-03-26 | 2013-03-08 | Photosensitive black resin composition and resin black matrix substrate |
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| KR20140148377A true KR20140148377A (en) | 2014-12-31 |
| KR101998449B1 KR101998449B1 (en) | 2019-07-09 |
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| JP (1) | JP5333696B1 (en) |
| KR (1) | KR101998449B1 (en) |
| CN (1) | CN104204945B (en) |
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| US10261356B2 (en) | 2015-07-14 | 2019-04-16 | Samsung Display Co., Ltd. | Liquid crystal display device and method of manufacturing the same |
| KR20190078312A (en) * | 2017-12-26 | 2019-07-04 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using the same and color filter |
| KR20190115950A (en) * | 2018-04-04 | 2019-10-14 | 삼성에스디아이 주식회사 | Red photosensitive resin composition, photosensitive resin layer using the same and color filter |
| KR20200028028A (en) * | 2017-09-26 | 2020-03-13 | 후지필름 가부시키가이샤 | Structure, partition wall forming composition, solid-state imaging element, and image display device |
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| TWI544281B (en) * | 2014-11-25 | 2016-08-01 | 奇美實業股份有限公司 | Photosensitive resin composition for black matrix and application thereof |
| TWI613486B (en) * | 2014-08-01 | 2018-02-01 | Toppan Printing Co Ltd | Black electrode substrate, method of manufacturing black electrode substrate, and display device |
| TWI564657B (en) * | 2014-08-28 | 2017-01-01 | Chi Mei Corp | Photosensitive resin composition for color filter and its application |
| JP6607682B2 (en) * | 2015-03-05 | 2019-11-20 | 日鉄ケミカル＆マテリアル株式会社 | Black resin composition for light-shielding film, substrate with light-shielding film having light-shielding film obtained by curing said composition, and color filter and touch panel having said substrate with light-shielding film |
| CN107615167A (en) * | 2015-05-29 | 2018-01-19 | 住友电木株式会社 | The manufacture method of photosensitive composition, colored pattern or black matrix, colour filter, liquid crystal display device or solid-state imager and colour filter |
| WO2019059169A1 (en) * | 2017-09-22 | 2019-03-28 | 東レ株式会社 | Transparent photosensitive resin composition, photospacer, liquid crystal display device, method for producing photospacer, method for producing liquid crystal display device, and use of transparent photosensitive resin composition for lens scan exposure |
| KR20210115795A (en) * | 2020-03-16 | 2021-09-27 | 동우 화인켐 주식회사 | Black Photosensitive Resin Composition, Black Matrix and Display Device |
| TWI744014B (en) | 2020-09-29 | 2021-10-21 | 新應材股份有限公司 | Black resin composition, cured film, and black filter |
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| WO2012002134A1 (en) * | 2010-07-02 | 2012-01-05 | 東レ株式会社 | Photosensitive resin composition, photosensitive resin composition film, and semiconductor device using the photosensitive resin composition or the photosensitive resin composition film |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10261356B2 (en) | 2015-07-14 | 2019-04-16 | Samsung Display Co., Ltd. | Liquid crystal display device and method of manufacturing the same |
| KR20200028028A (en) * | 2017-09-26 | 2020-03-13 | 후지필름 가부시키가이샤 | Structure, partition wall forming composition, solid-state imaging element, and image display device |
| KR20190078312A (en) * | 2017-12-26 | 2019-07-04 | 삼성에스디아이 주식회사 | Photosensitive resin composition, photosensitive resin layer using the same and color filter |
| KR20190115950A (en) * | 2018-04-04 | 2019-10-14 | 삼성에스디아이 주식회사 | Red photosensitive resin composition, photosensitive resin layer using the same and color filter |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104204945A (en) | 2014-12-10 |
| JPWO2013146183A1 (en) | 2015-12-10 |
| TW201348864A (en) | 2013-12-01 |
| CN104204945B (en) | 2017-10-03 |
| SG11201405096WA (en) | 2014-11-27 |
| TWI575314B (en) | 2017-03-21 |
| JP5333696B1 (en) | 2013-11-06 |
| KR101998449B1 (en) | 2019-07-09 |
| WO2013146183A1 (en) | 2013-10-03 |
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