Classifications

• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
  • G02B5/201—Filters in the form of arrays
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/0089—Non common dispersing agents non ionic dispersing agent, e.g. EO or PO addition products
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
  • C09B67/0071—Process features in the making of dyestuff preparations; Dehydrating agents; Dispersing agents; Dustfree compositions
  • C09B67/0084—Dispersions of dyes
  • C09B67/0085—Non common dispersing agents
  • C09B67/009—Non common dispersing agents polymeric dispersing agent
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
  • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
  • C09C1/44—Carbon
  • C09C1/48—Carbon black
  • C09C1/56—Treatment of carbon black ; Purification
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
  • G02B5/22—Absorbing filters
  • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments

Definitions

• the present invention relates to a colored composition, a color filter, and a color liquid crystal display element, and more particularly, formation of a colored layer useful for a color filter used in a transmissive or reflective color liquid crystal display device, a color imaging tube element, and the like.
• the present invention relates to a colored composition used in the present invention, a color filter including a colored layer formed using the colored composition, and a color liquid crystal display device including the color filter.
• a coating film of a colored radiation-sensitive composition is formed on a substrate or a substrate on which a light-shielding layer having a desired pattern has been previously formed, and a predetermined pattern is formed.
• a method of obtaining pixels of each color by irradiating radiation (hereinafter referred to as “exposure”) through a photomask having, developing and dissolving and removing unexposed portions, and then post-baking (Patent Document 1 and 2) is known.
• a method of forming a black matrix using a photopolymerizable composition containing a black material is also known.
• Patent Document 4 proposes the inclusion of a melamine resin or the like as a cross-linking agent in order to improve the chemical resistance of a colored layer formed using a colored composition.
• a coloring composition has a problem that sufficient development resistance and solvent resistance cannot be obtained when the exposure amount is low or a specific pigment is used.
• the present inventors have incorporated a crosslinking agent having a specific structure in which an oxiranyl group, an oxetanyl group or a group having a polymerizable unsaturated bond is bonded via an aminomethyloxy structure into the colorant and the binder resin.
• a crosslinking agent having a specific structure in which an oxiranyl group, an oxetanyl group or a group having a polymerizable unsaturated bond is bonded via an aminomethyloxy structure into the colorant and the binder resin.
• the present invention relates to (A) a colorant, (B) a binder resin, and (C) a compound having a structure represented by the following formula (1) (hereinafter these are collectively referred to as “specific crosslinking agent”.
• a coloring composition characterized in that it contains a pigment).
• X represents a group having an oxiranyl group, a group having an oxetanyl group or a group having a polymerizable unsaturated bond, and “*” represents a bond.
• the present invention also provides a color filter comprising a colored layer formed using the colored composition, and a color liquid crystal display device comprising the color filter.
• the “colored layer” in the present invention means a layer composed of pixels and / or a black matrix used for a color filter.
• the present invention provides a crosslinking compound having a structure represented by the above formula (1).
• X in the formula represents a group having an oxiranyl group or a group having an oxetanyl group
• “*” represents a bond.
• the present invention provides a crosslinking compound represented by any one of the following formulas (1-1) to (1-5).
• X 1 to X 6 are each independently a hydrogen atom, a group having an oxiranyl group, a group having an oxetanyl group, or a group having a polymerizable unsaturated bond.
• an alkyl group having 1 to 6 carbon atoms in which at least one of them is a group having an oxiranyl group, a group having an oxetanyl group, or a group having a polymerizable unsaturated bond, provided that the formula (1- In 1), two of X 1 to X 6 are (meth) acryloyl groups and the rest are methyl groups, and the (meth) acryloyl groups are bonded to two methyloxy groups on the same nitrogen atom.
• R 4 represents a hydrocarbon group having 1 to 12 carbon atoms
• R 5 and R 6 each independently represent a hydrogen atom or —CH 2 OX 1
• R 7 and R 8 represent Independently, it represents an alkyl group having 1 to 6 carbon atoms.
• the colored composition of the present invention has sufficient development resistance even at a low exposure amount, and can form a pixel and a black matrix having excellent solvent resistance. Therefore, the colored composition of the present invention can be used very suitably for the production of color filters for various uses such as color filters for color liquid crystal display elements, color imaging tube elements, color sensors and the like in the electronic industry.
• Coloring composition will be described components of the colored composition of the present invention.
• the colorant in the present invention is not particularly limited in color tone, and is appropriately selected according to the use of the obtained color filter, and may be any of a pigment, a dye, or a natural pigment. Since the color filter is required to have heat resistance, color developability and luminance, the colorant in the present invention is preferably an organic pigment, an inorganic pigment or an organic dye. Examples of the organic pigment include compounds classified as pigments in the Color Index (CI; issued by The Society of Dyers and Colorists), specifically, the following Color Index (C.I. ) Names can be mentioned.
• CI Color Index
• C.I. Color Index
• the organic pigment can be purified and used by a recrystallization method, a reprecipitation method, a solvent washing method, a sublimation method, a vacuum heating method, or a combination thereof.
• examples of the inorganic pigment include titanium oxide, barium sulfate, calcium carbonate, zinc white, lead sulfate, yellow lead, zinc yellow, red bean (red iron oxide (III)), cadmium red, ultramarine blue, bitumen, and chromium oxide.
• examples include green, cobalt green, amber, titanium black, synthetic iron black, and carbon black.
• organic dye examples include compounds having the following color index (CI) names.
• Disperse blue 165 C.I. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Molded Red 7, C.I. I. Moldant Yellow 5, C.I. I. Azo dyes such as Moldant Black 7; C. I. Bat Blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. Disperse thread 60, C.I. I. Disperse Blue 56, C.I. I. Anthraquinone dyes such as Disperse Blue 60; C. I. Phthalocyanine dyes such as Pad Blue 5; C. I. Basic Blue 3, C.I. I.
• Quinone imine dyes such as Basic Blue 9; C. I. Solvent Yellow 33, C.I. I. Acid Yellow 3, C.I. I. Quinoline dyes such as Disperse Yellow 64; C. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Nitro dyes such as Disperse Yellow 42.
• organic pigments and inorganic pigments may be used after the particle surface is modified with a polymer.
• the polymer that modifies the particle surface of the pigment include the polymers described in JP-A-8-259876, various commercially available polymers or oligomers for dispersing pigments, and the like.
• As the polymer coating method on the carbon black surface for example, methods disclosed in JP-A-9-71733, JP-A-9-95625, JP-A-9-124969 and the like can be employed.
• a coloring agent can be used individually or in mixture of 2 or more types.
• the colorant (A) is preferably a colorant having high color developability.
• Organic pigments and / or organic dyes are preferably used.
• the black matrix is required to have a light-shielding property. Therefore, an organic pigment or carbon black is preferably used as the colorant (A).
• the coloring composition of the present invention includes C.I. I. Pigment red 254, C.I. I.
• the coloring composition of this invention is useful also at the point which improves the solvent resistance of the colored layer formed using the coloring composition containing an organic dye as (A) a coloring agent.
• the content of (A) the colorant is preferably 5% by mass or more, more preferably 10% by mass, based on the total solid content of the colored composition.
• the colored composition of the present invention has excellent solvent resistance even when the content of (A) the colorant is 30% by mass or more in the total solid content of the colored composition.
• the upper limit of the content of the colorant is preferably 70% by mass or less, particularly preferably 60% by mass or less, in the total solid content of the color composition, from the viewpoint of ensuring developability.
• solid content is components other than the solvent mentioned later.
• the binder resin (B) in the present invention is not particularly limited, but is preferably an alkali-soluble resin having an acidic functional group such as a carboxyl group or a phenolic hydroxyl group.
• a polymer having a carboxyl group hereinafter referred to as “carboxyl group-containing polymer”
• carboxyl group-containing polymer an alkali-soluble resin having an acidic functional group
• an ethylenically unsaturated monomer having one or more carboxyl groups hereinafter referred to as “carboxyl group-containing unsaturated”.
• (meth) acrylic acid means methacrylic acid or acrylic acid.
• carboxyl group-containing unsaturated monomer examples include (meth) acrylic acid, succinic acid mono [2- (meth) acryloyloxyethyl], ⁇ -carboxypolycaprolactone mono (meth) acrylate, and the like. it can. These carboxyl group-containing unsaturated monomers can be used alone or in admixture of two or more.
• the copolymerization ratio of the carboxyl group-containing unsaturated monomer is preferably 5 to 50% by mass, more preferably 10%. ⁇ 40% by weight.
• copolymer having a carboxyl group examples include, for example, JP-A-7-140654, JP-A-10-31308, JP-A-10-300922, JP-A-11-174224, JP-A-11 Examples include copolymers disclosed in JP-A-258415, JP-A-2000-56118, JP-A-2004-101728, and the like.
• a carboxyl group-containing polymer having a polymerizable unsaturated bond such as a (meth) acryloyl group in the side chain can also be used as a binder resin.
• the weight average molecular weight in terms of polystyrene (hereinafter referred to as “Mw”) measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) of the binder resin in the present invention is usually 1,000 to 45,000, preferably 3,000 to 30,000. If Mw is too small, the remaining film rate of the resulting film may be reduced, pattern shape, heat resistance, etc. may be impaired, and electrical characteristics may be deteriorated. On the other hand, if Mw is too large, resolution may be reduced. In addition, the pattern shape may be damaged, and dry foreign matter may be easily generated during application by the slit nozzle method.
• the ratio (Mw / Mn) of the Mw of the binder resin in the present invention and the polystyrene-equivalent number average molecular weight (hereinafter referred to as “Mn”) measured by gel permeation chromatography (GPC, elution solvent: tetrahydrofuran) is Preferably it is 1.0 to 5.0, more preferably 1.0 to 3.0.
• the binder resin in the present invention can be produced by a known method.
• the structure, Mw, and Mw / Mn can be controlled by the methods disclosed in JP2003-222717A, JP2006-259680A, and International Publication No. 07/029871.
• binder resin can be used individually or in mixture of 2 or more types.
• the content of the binder resin is usually 10 to 1,000 parts by mass, preferably 20 to 500 parts by mass with respect to 100 parts by mass of the colorant (A). If the content of the binder resin is too small, for example, the alkali developability may be decreased, or the storage stability of the resulting colored composition may be decreased. On the other hand, if the content is too large, the colorant concentration is relatively high. Therefore, it may be difficult to achieve the target color density when a thin film is formed.
• the (C) specific crosslinking agent in the present invention is a compound having a structure represented by the above formula (1), and is a component that polymerizes during the exposure or post-bake process to cure the coating film.
• the colored composition of the present invention can form a colored layer having excellent development resistance and solvent resistance.
• the group having an oxiranyl group represented by X is not particularly limited, and examples thereof include a group represented by the following formula (X-1).
• R a represents a hydrogen atom or an alkyl group
• R b represents an alkylene group
• R c represents an ethylene group or a methylethylene group
• n represents 0 to 10
• R a is preferably a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, particularly preferably a hydrogen atom or a methyl group.
• R b is preferably an alkylene group having 1 to 6 carbon atoms such as a methylene group, an ethylene group or a methylethylene group, and n is preferably 0 to 5.
• the group having an oxetanyl group represented by X is not particularly limited, and examples thereof include an alkyl oxetanyl group, a dialkyl oxetanyl group, an oxetanyl alkyl group, an alkyl oxetanyl alkyl group, and a dialkyl oxetanyl alkyl group.
• the alkyl group substituted on the oxetanyl group preferably has 1 to 6 carbon atoms.
• 3-C 1-6 alkyloxetane-3-yl-C 1-4 alkyl group and more specifically, 3-methyloxetane-3-ylmethyl group, 3-methyloxetane- Examples include 3-ylethyl group, 3-ethyloxetane-3-ylmethyl group, and 3-ethyloxetane-3-ylethyl group.
• the group having a polymerizable unsaturated bond represented by X is not particularly limited.
• R d represents a hydrogen atom or a methyl group
• R e independently represents an ethylene group or a methylethylene group
• l represents 2 to 10
• R f represents a hydrogen atom or a methyl group
• R g represents an ethylene group or a methylethylene group
• m represents 0 to 10
• (meth) acryloyloxyalkyl group examples include (meth) acryloyloxyethyl group, (meth) acryloyloxypropyl group, (meth) acryloyloxybutyl group and the like.
• l is preferably 2 to 5.
• m is preferably 0 to 5.
• an oxyethylene group and an oxymethylethylene group may be mixed.
• the structure of the specific crosslinking agent has two or more groups selected from a group having an oxiranyl group represented by X, a group having an oxetanyl group, and a group having a polymerizable unsaturated bond.
• X is preferably a group having an oxetanyl group, a group having a polymerizable unsaturated bond, or both of them.
• the specific crosslinking agent those having a ureido structure, a glycoluril structure, a melamine structure, a benzoguanamine structure or an imidazolidin-2-one structure are more preferable.
• the melamine structure and the benzoguanamine structure refer to a chemical structure having one or more triazine rings or phenyl-substituted triazine rings as a basic skeleton, and are a concept including a melamine compound, a benzoguanamine compound or a condensate thereof.
• the specific crosslinking agent is a compound selected from the following formulas (1-1), (1-2), (1-3), (1-4) and (1-5). preferable.
• X 1 to X 6 are each independently a hydrogen atom, a group having an oxiranyl group, a group having an oxetanyl group, a group having a polymerizable unsaturated bond, or an alkyl group having 1 to 6 carbon atoms.
• At least one of them is a group having an oxiranyl group, a group having an oxetanyl group, or a group having a polymerizable unsaturated bond
• R 4 represents a hydrocarbon group having 1 to 12 carbon atoms
• R 5 And R 6 each independently represent a hydrogen atom or —CH 2 OX 1
• R 7 and R 8 each independently represent an alkyl group having 1 to 6 carbon atoms.
• X 1 to X 6 in the compounds of the formulas (1-1) to (1-5) are at least two of a group having an oxiranyl group, a group having an oxetanyl group, or a group having a polymerizable unsaturated bond. It is preferable.
• the alkyl group having 1 to 6 carbon atoms in X 1 to X 6 , R 7 and R 8 include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl. Group, tert-butyl group, n-pentyl group, n-hexyl group and the like.
• Examples of the hydrocarbon group having 1 to 12 carbon atoms in R 4 include an alkyl group having 1 to 12 carbon atoms and an aromatic hydrocarbon group having 6 to 12 carbon atoms. Specific examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and a phenyl group.
• the compounds of the formulas (1-1) and (1-2) are more preferred from the viewpoint of development resistance and solvent resistance, and particularly the formula (1-1) ) Is preferred.
• the formula (1-1) it is preferable that two or more of X 1 to X 6 are a group having an oxetanyl group or a group having a polymerizable unsaturated bond, and 2 to 2 of X 1 to X 6 More preferably, five are groups having an oxetanyl group, or at least one of X 1 to X 6 is a group having an oxetanyl group, and two or more are groups having a polymerizable unsaturated bond. .
• two or more of X 1 to X 4 are preferably a group having an oxetanyl group or a group having a polymerizable unsaturated bond, and R 4 is an aromatic group having 6 to 12 carbon atoms.
• a group hydrocarbon group is preferred.
• X 1 and X 2 is a group having an oxetanyl group
• R 5 and R 6 are -CH 2 OX 1
• X 1 of the -CH 2 OX 1 is An alkyl group having 1 to 6 carbon atoms is preferable.
• (C) specific crosslinking agent examples include compounds represented by the following (C-1) to (C-10).
• (C) specific crosslinking agent can be used individually or in mixture of 2 or more types.
• the content of (C) the specific cross-linking agent is 0.1 to 300 parts by mass, more preferably 1 to 100 parts by mass of (B) binder resin from the viewpoint of improvement in development resistance and solvent resistance. ⁇ 200 parts by weight are preferred.
• the curability of the formed colored layer can be further improved.
• the monomer having a polymerizable unsaturated bond include a polyfunctional monomer having two or more polymerizable unsaturated bonds and a monofunctional monomer having one polymerizable unsaturated bond. be able to.
• polyfunctional monomer examples include: Di (meth) acrylates of alkylene glycols such as ethylene glycol and propylene glycol; Di (meth) acrylates of polyalkylene glycols such as polyethylene glycol and polypropylene glycol; Poly (meth) acrylates of trihydric or higher polyhydric alcohols such as glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol and the like, and their dicarboxylic acid-modified products; Oligo (meth) acrylates such as polyester, epoxy resin, urethane resin, alkyd resin, silicone resin, spirane resin; Di (meth) acrylates of hydroxylated polymers at both ends such as both ends hydroxypoly-1,3-butadiene, both ends hydroxypolyisoprene, both ends hydroxypolycaprolactone; Tris [2- (meth) acryloyloxyethyl] phosphate;
• Examples of the monofunctional monomer include divalent or higher polyvalent monomers such as succinic acid mono [2- (meth) acryloyloxyethyl] and phthalic acid mono [2- (meth) acryloyloxyethyl].
• Mono [(meth) acryloyloxyalkyl] esters of monovalent carboxylic acids such as ⁇ -carboxypolycaprolactone mono (meth) acrylate; N-vinylsuccin Imido, N-vinyl pyrrolidone, N-vinyl phthalimide, N-vinyl-2-piperidone, N-vinyl- ⁇ -caprolactam, N-vinyl pyrrole, N-vinyl pyrrolidine, N-vinyl imidazole, N-vinyl imidazolidine, N -Vinylindole, N-vinylindoline, N-
• the monomer having a polymerizable unsaturated bond is preferably a polyfunctional monomer, and in particular, a poly (meth) acrylate of a trihydric or higher polyhydric alcohol or a dicarboxylic acid modified product thereof, urethane.
• a poly (meth) acrylate having a structure and a poly (meth) acrylate having a caprolactone structure are preferred.
• poly (meth) acrylates of trihydric or higher polyhydric alcohols or dicarboxylic acid modified products thereof include trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate, Pentaerythritol tetramethacrylate, dipentaerythritol pentaacrylate, dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate, dipentaerythritol hexamethacrylate or monoesterified product of pentaerythritol triacrylate and succinic acid; pentaerythritol trimethacrylate and succinic acid Monoesterified product of dipentaerythritol Monoesterified product of taacrylate and succin
• the content of the monomer having a polymerizable unsaturated bond in the present invention is preferably 5 to 400 parts by mass, more preferably 20 to 300 parts by mass with respect to 100 parts by mass of the (C) specific crosslinking agent.
• Photopolymerization initiator- Radiation sensitivity can be imparted to the colored composition by incorporating a photopolymerization initiator into the colored composition of the present invention.
• radiation means a substance including visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray and the like.
• the photopolymerization initiator is used by (C) a specific cross-linking agent and (D) a polymerizable non-polymerizing agent by exposure to radiation such as visible light, ultraviolet light, far ultraviolet light, electron beam, and X-ray. It is a compound that generates an active species capable of initiating polymerization of a monomer having a saturated bond.
• photopolymerization initiators examples include photo radical generators such as thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, O-acyloxime compounds, benzoin compounds, benzophenone compounds, Known compounds such as ⁇ -diketone compounds, polynuclear quinone compounds, and xanthone compounds can be exemplified.
• photoacid generator examples include known compounds such as an onium salt compound, a sulfone compound, a sulfonic acid ester compound, a quinonediazide compound, a sulfonimide compound, and a diazomethane compound.
• the triazine-based compounds exemplified as the photo radical generator are compounds that also function as a photo acid generator.
• a photoinitiator can be used individually or in mixture of 2 or more types, Of course, a photoradical generator and a photoacid generator can also be mixed and used.
• the photoradical generator preferably contains at least one selected from the group of thioxanthone compounds, acetophenone compounds, biimidazole compounds, triazine compounds, and O-acyloxime compounds.
• thioxanthone compounds include thioxanthone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4-isopropylthioxanthone, 2,4-dichlorothioxanthone, 2 , 4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone and the like.
• acetophenone compound examples include 2-methyl-1- [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4 -Morpholinophenyl) butan-1-one, 2- (4-methylbenzyl) -2- (dimethylamino) -1- (4-morpholinophenyl) butan-1-one, and the like.
• biimidazole compound examples include 2,2′-bis (2-chlorophenyl) -4,4 ′, 5,5′-tetraphenyl-1,2′-biimidazole, 2,2 ′.
• -Bis (2,4-dichlorophenyl) -4,4 ', 5,5'-tetraphenyl-1,2'-biimidazole, 2,2'-bis (2,4,6-trichlorophenyl) -4, 4 ′, 5,5′-tetraphenyl-1,2′-biimidazole and the like can be mentioned.
• a hydrogen donor in combination because sensitivity can be improved.
• the “hydrogen donor” as used herein means a compound that can donate a hydrogen atom to a radical generated from a biimidazole compound by exposure.
• the hydrogen donor include mercaptan-based hydrogen donors such as 2-mercaptobenzothiazole and 2-mercaptobenzoxazole, 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, and the like.
• an amine-based hydrogen donor can be used alone or in admixture of two or more. However, one or more mercaptan hydrogen donors and one or more amine hydrogen donors are used in combination. It is preferable that the sensitivity can be further improved.
• triazine compound examples include 2,4,6-tris (trichloromethyl) -s-triazine, 2-methyl-4,6-bis (trichloromethyl) -s-triazine, 2- [2 -(5-Methylfuran-2-yl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (furan-2-yl) ethenyl] -4,6-bis (trichloro Methyl) -s-triazine, 2- [2- (4-diethylamino-2-methylphenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- [2- (3,4-dimethoxy) Phenyl) ethenyl] -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxyphenyl) -4,6-bis (t
• O-acyloxime compounds include 1,2-octanedione, 1- [4- (phenylthio) phenyl]-, 2- (O-benzoyloxime), ethanone, 1- [9-ethyl.
• a sensitizer when a photo radical generator other than a biimidazole compound such as an acetophenone compound is used, a sensitizer can be used in combination.
• a sensitizer include 4,4′-bis (dimethylamino) benzophenone, 4,4′-bis (diethylamino) benzophenone, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, and 4-dimethyl.
• Ethyl aminobenzoate 2-ethylhexyl 4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4-diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. Can be mentioned.
• the content thereof is preferably 1 to 2000 parts by mass, more preferably 5 to 1000 parts by mass with respect to 100 parts by mass of the (C) specific crosslinking agent. If the content of the photoradical generator is too large, curing by exposure may be insufficient, while if too large, the formed colored layer tends to fall off the substrate during development.
• the photoacid generator preferably contains at least one selected from the group of onium salt compounds, sulfonimide compounds and diazomethane compounds.
• examples of the onium salt compound include diaryl iodonium salts, triarylsulfonium salts, triarylphosphonium salts and the like.
• Specific examples of the diaryliodonium salt include diphenyliodonium tetrafluoroborate, diphenyliodonium hexafluorophosphonate, diphenyliodonium hexafluoroantimonate, diphenyliodonium hexafluoroarsenate, diphenyliodonium trifluoromethanesulfonate, diphenyliodonium trifluoroacetate, diphenyl Iodonium-p-toluenesulfonate, 4-methoxyphenylphenyliodonium tetrafluoroborate, 4-methoxyphenylphenyliodonium hexafluorophosphonate, 4-methoxyphenylphenylphenyliodonium hex
• triarylsulfonium salt examples include triphenylsulfonium tetrafluoroborate, triphenylsulfonium hexafluorophosphonate, triphenylsulfonium hexafluoroantimonate, triphenylsulfonium hexafluoroarsenate, triphenylsulfonium trifluoromethanesulfonate, triphenylsulfonium hexafluorophosphonate, Phenylsulfonium trifluoroacetate, triphenylsulfonium-p-toluenesulfonate, 4-methoxyphenyldiphenylsulfonium tetrafluoroborate, 4-methoxyphenyldiphenylsulfonium hexafluorophosphonate, 4-methoxyphenyldiphenylsulfonium hexafluoroantimonate, 4-methoxy
• triarylphosphonium salt examples include triphenylphosphonium tetrafluoroborate, triphenylphosphonium hexafluorophosphonate, triphenylphosphonium hexafluoroantimonate, triphenylphosphonium hexafluoroarsenate, triphenylphosphonium trifluoromethanesulfonate, Phenylphosphonium trifluoroacetate, triphenylphosphonium-p-toluenesulfonate, 4-methoxyphenyldiphenylphosphonium tetrafluoroborate, 4-methoxyphenyldiphenylphosphonium hexafluorophosphonate, 4-methoxyphenyldiphenylphosphonium hexafluoroantimonate, 4-methoxy Phenyldiphenylphosphonium hex Fluoroarsenate, 4-methoxyphenyldiphenylphosphonium trifluoromethanes, Ph
• sulfonimide compound examples include N- (trifluoromethylsulfonyloxy) succinimide, N- (trifluoromethylsulfonyloxy) phthalimide, N- (trifluoromethylsulfonyloxy) diphenylmaleimide, N- (trimethyl).
• diazomethane compound examples include bis (trifluoromethylsulfonyl) diazomethane, bis (cyclohexylsulfonyl) diazomethane, bis (phenylsulfonyl) diazomethane, bis (p-toluenesulfonyl) diazomethane, methylsulfonyl-p-toluenesulfonyl.
• diazomethane 1-cyclohexylsulfonyl-1- (1,1-dimethylethylsulfonyl) diazomethane, bis (1,1-dimethylethylsulfonyl) diazomethane, and the like.
• the content thereof when a photoacid generator is used, the content thereof is usually 0.1 to 100 parts by mass, preferably 0.3 to 50 parts by mass with respect to 100 parts by mass of (C) the specific crosslinking agent. It is. If the content of the photoacid generator is too small, curing by exposure may be insufficient. On the other hand, if the content is too large, foreign matter may be generated in the colored composition liquid or electrical characteristics may be deteriorated. is there.
• the coloring composition of this invention can also contain a various additive as needed.
• the additive include a thermal acid generator that promotes a curing reaction by opening a ring of an oxiranyl group, an oxetanyl group, and the like of the (C) specific crosslinking agent in the post-baking step.
• thermal acid generators include 4-acetoxyphenyldimethylsulfonium hexafluoroarsenate, benzyl-4-hydroxyphenylmethylsulfonium hexafluoroantimonate, 4-acetoxyphenylbenzylmethylsulfonium hexafluoroantimonate, dibenzyl-4 -Hydroxyphenylsulfonium hexafluoroantimonate, 4-acetoxyphenylbenzylsulfonium hexafluoroantimonate, 3-benzylbenzothiazonium hexafluoroantimonate, and the like.
• additives include, for example, fillers such as glass and alumina; polymer compounds such as polyvinyl alcohol and poly (fluoroalkyl acrylates); nonionic surfactants, cationic surfactants, anionic surfactants Surfactant such as an agent; vinyltrimethoxysilane, vinyltriethoxysilane, vinyltris (2-methoxyethoxy) silane, N- (2-aminoethyl) -3-aminopropylmethyldimethoxysilane, N- (2-aminoethyl) ) -3-Aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltri Methoxysilane, 3-chloropropylmethyl Adhesion promoters such as me
• the coloring composition of the present invention contains the components (A) to (C) and other components that are optionally added, and is usually prepared as a liquid composition by blending a solvent.
• the solvent is appropriately selected as long as it is dispersed or dissolved (A) to (C) and other components constituting the coloring composition and does not react with these components and has appropriate volatility. You can choose to use.
• Alcohols such as methanol, ethanol, benzyl alcohol; Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol mono-n-propyl ether, ethylene glycol mono-n-butyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-propyl ether, diethylene glycol mono-n- Butyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol mono-n-propyl ether, di Propylene glycol mono- - butyl ether, tripropylene glycol monomethyl ether, tripropylene glycol (poly) alkylene glycol monoal
• Diacetates such as propylene glycol diacetate, 1,3-butylene glycol diacetate, and 1,6-hexanediol diacetate; Lactic acid alkyl esters such as methyl lactate and ethyl lactate; Ethyl acetate, n-propyl acetate, i-propyl acetate, n-butyl acetate, i-butyl acetate, n-pentyl formate, i-pentyl acetate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl acetate, N-butyl propionate, 3-methoxybutyl acetate, 3-methyl-3-methoxybutyl propionate, ethyl butyrate, n-propyl butyrate, i-propyl butyrate, n-butyl butyrate, ethyl hydroxyacetate, ethyl ethoxyacetate,
• benzyl alcohol ethylene glycol mono-n-butyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, ethylene glycol monomethyl ether acetate, ethylene glycol are used from the viewpoints of solubility, pigment dispersibility, coatability, etc.
• a high boiling point solvent such as diethyl, ⁇ -butyrolactone, ethylene carbonate, propylene carbonate, ethylene glycol monophenyl ether acetate may be used in combination.
• the high boiling point solvents can be used alone or in admixture of two or more.
• the content of the solvent is not particularly limited, but the total concentration of each component excluding the solvent from the colored composition is usually 5 from the viewpoint of applicability and stability of the obtained colored composition. An amount of ⁇ 50 mass% is preferred, and an amount of 10 ⁇ 40 mass% is particularly desirable.
• the coloring composition can be prepared by an appropriate method.
• the coloring composition is prepared by mixing the components (A) to (C) together with a solvent and other components optionally added. Can do.
• a preferable preparation method for example, a bead mill, a roll mill, or the like is used together with a part of the component (B) in the presence of (A) a colorant in a solvent, a dispersant and, if necessary, a dispersion aid. Mix and disperse while pulverizing to obtain a pigment dispersion, which is prepared by adding components (B) to (C) and, if necessary, additional solvent and other components and mixing them.
• a method can be mentioned.
• an appropriate dispersant such as a cationic, anionic, nonionic or amphoteric
• a polymer dispersant is preferable.
• a modified acrylic copolymer, an acrylic copolymer, polyurethane, polyester, a polymer copolymer alkylammonium salt or phosphate ester salt, a cationic comb graft polymer, and the like can be given.
• the cationic comb graft polymer refers to a polymer having a structure in which two or more branched polymers are grafted to one molecule of a trunk polymer having a plurality of basic groups (cationic functional groups).
• Examples thereof include polymers composed of a ring-opening polymer in which the trunk polymer part is polyethyleneimine and the branch polymer part is ⁇ -caprolactone.
• these dispersants modified acrylic copolymers, polyurethane, and cationic comb graft polymers are preferable.
• Such a dispersant is commercially available.
• Disperbyk-2000, Disperbyk-2001, BYK-LPN6919, BYK-LPN21116, BYK-LPN21324 above, BYK Dispersbyk-161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182 (or more, manufactured by BYK Chemy (BYK)
• Solsperse 76500 Librisol Co., Ltd.
• Solsperse 24000 manufactured by Lubrizol Co., Ltd.
• Azisper PB821, Azisper PB822 AJISPER PB823, Adisper PB824 mention may be made of Ajisper PB827 (Ajinomoto Fine-Techno Co., Ltd.), and the like.
• the content of the dispersant is usually 100 parts by mass or less, preferably 0.5 to 100 parts by mass, more preferably 1 with respect to 100 parts by mass of the colorant (A) from the viewpoint of improving developability and the like. It is ⁇ 70 parts by mass, particularly preferably 10 to 50 parts by mass.
• the color filter of the present invention comprises a colored layer formed from the colored composition of the present invention.
• a method for forming a color filter first, a colored radiation-sensitive composition coating film is formed on a substrate or a substrate on which a light-shielding layer having a desired pattern has been previously formed, and a photo having a predetermined pattern is formed.
• a method of obtaining pixels of each color by exposing radiation through a mask, developing to dissolve and remove unexposed portions, and then post-baking.
• a light shielding layer black matrix
• a red pigment for example, is dispersed on the substrate.
• pre-baking is performed to evaporate the solvent, thereby forming a coating film.
• the coating film is exposed through a photomask, and then developed using an alkali developer to dissolve and remove the unexposed portions of the coating film, and then post-baked to form a red pixel pattern.
• a pixel array arranged in an array is formed.
• the liquid composition is applied, pre-baked, exposed, developed, and post-baked in the same manner as described above, to thereby obtain a green pixel.
• a color filter in which the pixel arrays of the three primary colors of red, green and blue are arranged on the substrate is obtained.
• the order of forming the pixels of each color is not limited to the above.
• the black matrix can be formed in the same manner as in the case of forming the pixel by using the colored composition of the present invention.
• the substrate used when forming the pixel and / or the black matrix examples include glass, silicon, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide.
• these substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent or the like, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.
• an appropriate coating method such as a spray method, a roll coating method, a spin coating method (spin coating method), a slit die coating method, a bar coating method, or an ink jet method is used.
• spin coating and slit die coating are preferable.
• the coating thickness is usually 0.1 to 10 ⁇ m, preferably 0.2 to 8.0 ⁇ m, particularly preferably 0.2 to 6.0 ⁇ m, as the film thickness after drying.
• the radiation used for forming the pixel and / or the black matrix for example, visible light, ultraviolet light, far ultraviolet light, electron beam, X-ray or the like can be used, but the wavelength is in the range of 190 to 450 nm. Some radiation is preferred.
• the exposure dose of radiation is preferably 10 to 10,000 J / m 2 . According to the colored composition of the present invention, 800 J / m 2 or less of the exposure amount, and further it can form pixels excellent in solvent resistance at 600 J / m 2 or less of the exposure amount.
• alkali developer examples include sodium carbonate, sodium hydroxide, potassium hydroxide, tetramethylammonium hydroxide, choline, 1,8-diazabicyclo- [5.4.0] -7-undecene, 1, An aqueous solution of 5-diazabicyclo- [4.3.0] -5-nonene or the like is preferable.
• An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline developer. In addition, it is usually washed with water after alkali development.
• a development processing method a shower development method, a spray development method, a dip (immersion) development method, a paddle (liquid accumulation) development method, or the like can be applied.
• the development conditions are preferably 5 to 300 seconds at room temperature.
• a method for obtaining pixels of each color by an ink jet method disclosed in Japanese Patent Laid-Open Nos. 4-2615033 and 7-318723 is also known.
• the color filter of the present invention thus obtained is extremely useful for high-definition color liquid crystal surface elements, color image pickup tube elements, color sensors and the like.
• the color liquid crystal display element of the present invention comprises the color filter of the present invention.
• the color liquid crystal display element of the present invention can have an appropriate structure.
• the color filter is formed on a substrate different from the driving substrate on which the thin film transistor (TFT) is arranged, and the driving substrate and the substrate on which the color filter is formed are opposed to each other with a liquid crystal layer interposed therebetween. Can be taken.
• a substrate on which a color filter is formed on the surface of a driving substrate on which a thin film transistor (TFT) is disposed, and a substrate on which an ITO (tin-doped indium oxide) electrode is formed are opposed to each other through a liquid crystal layer.
• the structure can be taken.
• the latter structure has the advantage that the aperture ratio can be remarkably improved, and a bright and high-definition liquid crystal display element can be obtained.
• Preparation Example 2 (A) 20 parts by mass of carbon black as a colorant, 4 parts by mass of Disperbyk-167 as a dispersant (in terms of solid content), and 3-methoxybutyl acetate as a solvent so that the solid content concentration is 24% by mass,
• the pigment dispersion (A-2) was prepared by processing with a bead mill.
• Synthesis example 2 A flask equipped with a condenser and a stirrer was charged with 800 g of cyclohexanone, heated to 100 ° C. while injecting nitrogen gas into the flask, and at the same temperature, 60.0 g of styrene, 60.0 g of methacrylic acid, 65. methyl methacrylate. A mixture of 0 g, butyl methacrylate 65.0 g, and azobisisobutyronitrile 10.0 g was added dropwise over 1 hour, and further reacted at 100 ° C. for 3 hours, and then 2.0 g of azobisisobutyronitrile was added.
• Synthesis example 4 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser, and gas introduction tube, 580 g of Cymel 300, 642 g of 3-ethyl-3-hydroxymethyloxetane, 580 g of propylene glycol monomethyl ether acetate, and 2 g of p-toluenesulfonic acid were added. The mixture was heated to 80 ° C. and reacted for 1 hour while distilling off the generated methanol. Then, it neutralized with 0.1N sodium hydroxide aqueous solution, and the non volatile matter was 80 mass% by vacuum concentration.
• a specific cross-linking agent in which an average of about 4 of the 6 methoxy groups in the compound represented by the formula (a) is substituted with a (3-ethyloxetane-3-yl) methoxy group is used.
• the obtained specific crosslinking agent mixture is designated as specific crosslinking agent [C-2].
• a compound in which an average of about 4 of the 6 methoxy groups in the compound represented by the formula (a) is substituted with a (3-ethyloxetane-3-yl) methoxy group is obtained.
• Synthesis example 5 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser and gas introduction tube, 126 g of melamine, 202 g of 92% paraformaldehyde (Mitsubishi Gas Chemical Co., Ltd.), 1393 g of 2-hydroxyethyl acrylate, 520 g of 2-hydroxyethyl methacrylate Then, 256 g of methanol was added, the temperature was raised to 80 ° C., a methylolation reaction was performed at 80 ° C. for 1 hour, 1 g of p-toluenesulfonic acid was added, and an etherification reaction was performed at 80 ° C. for 3 hours.
• the obtained specific crosslinking agent mixture is designated as specific crosslinking agent [C-3].
• specific crosslinking agent [C-3] Of the six methoxy groups in the compound represented by the above formula (a), a compound having an average of about 3 substituted with an acryloyloxyethyloxy group and an average of about 1 with a methacryloyloxyethyloxy group It was confirmed by 1 H-NMR and GPC that it was obtained.
• Synthesis Example 6 A four-necked flask equipped with a stirrer, thermometer, reflux condenser and gas introduction tube was charged with 126 g of melamine, 202 g of 92% paraformaldehyde, 290 g of 3-ethyl-3-hydroxymethyloxetane, and 160 g of methanol, and the temperature was raised to 80 ° C. The methylolation reaction was carried out at 80 ° C. for 1 hour, 1 g of p-toluenesulfonic acid was added, and the etherification reaction was carried out at 80 ° C. for 3 hours.
• Synthesis example 7 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser and gas introduction tube, 580 g of Cymel 300, 325 g of 3-ethyl-3-hydroxymethyloxetane, 325 g of 2-hydroxyethyl acrylate, glycidol (manufactured by NOF Corporation) ) 104 g, toluene 580 g and p-toluenesulfonic acid 1 g were charged and heated to 80 ° C., and the reaction was carried out for 3 hours while distilling off the generated methanol.
• an average of about 2 is a (3-ethyloxetane-3-yl) methoxy group and an average of about 2 is acryloyl.
• a solution of a specific cross-linking agent mixture containing a specific cross-linking agent having an average of about 1 oxyethyloxy group substituted with a glycidyloxy group was obtained.
• the obtained specific crosslinking agent mixture is designated as specific crosslinking agent [C-5].
• an average of about 2 is a (3-ethyloxetane-3-yl) methoxy group and an average of about 2 is acryloyloxyethyloxy. It was confirmed by 1 H-NMR and GPC that a compound having an average of about 1 group substituted with a glycidyloxy group was obtained.
• Synthesis example 8 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser and gas introduction tube, melamine 126 g, 202% paraformaldehyde 202 g, 2-hydroxyethyl acrylate 1393 g, 2-hydroxyethyl vinyl ether (manufactured by Maruzen Petrochemical Co., Ltd.) 280 g Then, 256 g of methanol was added, the temperature was raised to 80 ° C., and a methylolation reaction was performed at 80 ° C. for 1 hour, 1 g of paratoluenesulfonic acid was added, and an etherification reaction was performed at 80 ° C. for 3 hours.
• R is a methyl group or an ethyl group.
• Synthesis Example 11 In a four-necked flask equipped with a stirrer, thermometer, reflux condenser and gas introduction tube, 126 g of melamine, 202 g of 92% paraformaldehyde, 464 g of 2-hydroxyethyl acrylate, 116 g of 3-ethyl-3-hydroxymethyloxetane, and 32 g of methanol The mixture was heated up to 80 ° C. and subjected to a methylolation reaction at 80 ° C. for 1 hour, 1 g of p-toluenesulfonic acid was added, and an etherification reaction was carried out at 80 ° C. for 3 hours.
• the obtained specific crosslinker mixture is designated as specific crosslinker [C-9].
• specific crosslinker [C-9] Of the six methoxy groups in the compound represented by the formula (a), an average of about 4 is an acryloyloxyethyloxy group and an average of about 1 is (3-ethyloxetane-3-yl) methoxy. It was confirmed by 1 H-NMR that a compound substituted with a group was obtained.
• Example 1 Preparation of coloring composition (A) 100.0 parts by mass of pigment dispersion (A-1) as a colorant, (B) 26.0 parts by mass of a binder resin [B-1] solution as a binder resin, and a binder resin [B- 2) 6.6 parts by mass of the solution, (C) 9.9 parts by mass of the solution containing the specific cross-linking agent [C-1] as the specific cross-linking agent, and (D) Toagosei as the monomer having a polymerizable unsaturated bond 5.4 parts by mass of M-402 (dipentaerythritol hexaacrylate) manufactured by Toyo Gosei Co., Ltd.
• M-402 dipentaerythritol hexaacrylate
• Pattern formation The colored radiation-sensitive composition obtained was applied to a soda glass substrate with a SiO 2 film formed on the surface to prevent elution of sodium ions, using a spin coater, and then on a hot plate at 90 ° C. Was pre-baked for 2 minutes to form a film having a thickness of 1.7 ⁇ m.
• each wavelength of 365 nm, 405 nm, and 436 nm was applied to the coating film through a photomask having a plurality of slits having different sizes in a width range of 5 to 50 ⁇ m using a high-pressure mercury lamp. Exposed ultraviolet light was exposed. The exposure amount at this time was 500 J / m 2 .
• the substrate was subjected to shower development using a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C. for 1 minute, then washed with ultrapure water and air-dried. Thereafter, post-baking was performed in a clean oven at 220 ° C. for 30 minutes to form a pixel array in which red stripe pixel patterns were arranged on the substrate.
• the obtained colored radiation-sensitive composition was applied to a soda glass substrate having a SiO 2 film formed on its surface to prevent elution of sodium ions, using a spin coater, and then a hot plate at 90 ° C. The film was pre-baked for 2 minutes to form a film having a thickness of 1.7 ⁇ m. Next, after cooling the substrate to room temperature, the coating film was exposed to ultraviolet rays including wavelengths of 365 nm, 405 nm, and 436 nm without using a photomask using a high-pressure mercury lamp. The exposure amount at this time was 500 J / m 2 .
• the substrate was subjected to shower development using a 0.04 mass% potassium hydroxide aqueous solution at 23 ° C. for 1 minute, then washed with ultrapure water and air-dried. Thereafter, post-baking was performed in a clean oven at 220 ° C. for 30 minutes to form a red cured film on the substrate.
• the substrate on which the red cured film was formed was immersed in N-methylpyrrolidone at 60 ° C. for 30 minutes.
• the film thickness ratio before and after immersion film thickness after immersion ⁇ 100 / film thickness before immersion
• the case where the film thickness ratio before and after immersion was less than 95% or the N-methylpyrrolidone after immersion was slightly colored was evaluated as “B”, and the case where cracks occurred after immersion was evaluated as “C”.
• Example 1 As shown in Table 1, a colored radiation-sensitive composition was prepared in the same manner as in Example 1 except that the type and content (parts by mass) of each component were changed. Subsequently, various evaluation was performed like Example 1 using the obtained colored radiation-sensitive composition. The results are shown in Table 1.
• each component is as follows.
• c-1 Cymel 300 manufactured by Nippon Cytec Industries, Ltd. (compound of formula (a) as a main component)
• c-2 Cymel 1123 manufactured by Nippon Cytec Industries, Ltd. (compound of formula (c) as a main component)
• D-1 Dipentaerythritol hexaacrylate (trade name M-402, manufactured by Toagosei Co., Ltd.)
• D-2 monoesterified product of dipentaerythritol pentaacrylate and succinic acid, dipentaerythritol hexaacrylate and mixture of dipentaerythritol pentaacrylate (trade name TO-1382, manufactured by Toagosei Co., Ltd.)
• D-3 Pentaerythritol tetraacrylate (trade name M-450, manufactured by Toagosei Co., Ltd.)
• E-1 2-methyl-1- [4- (methylthio) pheny

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