Classifications

• • 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
• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3412—Heterocyclic compounds having nitrogen in the ring having one nitrogen atom in the ring
  • C08K5/3432—Six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/34—Heterocyclic compounds having nitrogen in the ring
  • C08K5/3467—Heterocyclic compounds having nitrogen in the ring having more than two nitrogen atoms in the ring
  • C08K5/3477—Six-membered rings
• • 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
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/0003—Monoazo dyes prepared by diazotising and coupling from diazotized anilines
  • C09B29/0007—Monoazo dyes prepared by diazotising and coupling from diazotized anilines containing acid groups, e.g. CO2H, SO3H, PO3H2, OSO3H, OPO2H2; Salts thereof
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B29/00—Monoazo dyes prepared by diazotising and coupling
  • C09B29/34—Monoazo dyes prepared by diazotising and coupling from other coupling components
  • C09B29/36—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds
  • C09B29/3604—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom
  • C09B29/3617—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom
  • C09B29/3621—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring
  • C09B29/3626—Monoazo dyes prepared by diazotising and coupling from other coupling components from heterocyclic compounds containing only a nitrogen as heteroatom containing a six-membered heterocyclic with only one nitrogen as heteroatom from a pyridine ring from a pyridine ring containing one or more hydroxyl groups (or = O)
• • 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
  • C09B57/00—Other synthetic dyes of known constitution
  • C09B57/04—Isoindoline dyes
• • 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
  • C09B67/0001—Post-treatment of organic pigments or dyes
  • C09B67/0004—Coated particulate pigments or dyes
  • C09B67/0008—Coated particulate pigments or dyes with organic coatings
  • C09B67/0013—Coated particulate pigments or dyes with organic coatings with polymeric coatings
• • 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
  • C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
  • C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
• • 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
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/02—Printing inks
  • C09D11/03—Printing inks characterised by features other than the chemical nature of the binder
  • C09D11/037—Printing inks characterised by features other than the chemical nature of the binder characterised by the pigment
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
  • C09D11/00—Inks
  • C09D11/30—Inkjet printing inks
  • C09D11/32—Inkjet printing inks characterised by colouring agents
  • C09D11/322—Pigment inks
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
  • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
• • 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
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

• the present invention relates to a pigment dispersion for use in production steps of coating materials, inks, color filters, resin moldings, etc.
• the present invention further relates to a yellow resist
• composition for color filter and an ink composition containing the pigment dispersion as a colorant.
• color image data is color-separated through respective color filters of blue, green, and red, and a latent image corresponding to the original image is then developed using respective color developers of yellow, magenta, cyan, and black.
• the coloring power of a colorant in each color developer largely influences image quality.
• Typical examples of the yellow colorant include
• pigments having an isoindoline skeleton such as C.I. Pigment yellow 185, which has high transparency and coloring power and excellent weather resistance.
• PTL 1 discloses a pigment dispersant such as a pigment dispersion containing an isoindoline pigment with an introduced sulfonic acid group.
• an object of the present invention is to provide a pigment dispersion excellent in the
• Another object of the present invention is to provide a yellow resist composition for color filter and an ink composition containing the pigment dispersion.
• the present invention relates to a
• the present invention also relates to a yellow resist composition for color filter and an ink composition havin favorable yellow tone.
• A represents -S0 2 N(R 4 )R 5 or -CON(R 4 )R 5 wherein R 4 represents a hydrogen atom or an alkyl group, and R 5 represents an alkyl group; R x represents an alkyl group, an aryl group, or an amino group; R 3 represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; and R 2 represents (i) a hydrogen atom, a cyano group, or a carbamoyl group provided that R 3 represents a hydrogen atom, or (ii) a hydrogen atom, a cyano group, a carboxylic acid group, a carboxylic acid ester group, a carboxylic acid amide group, or a
• R 3 represents an alkyl group, an aryl group, or an aralkyl group.
• the present invention can provide a pigment dispersion excellent in the dispersibility of C.I. Pigment yellow 185 in a dispersing medium. Furthermore, use of the pigment dispersion can provide a resist composition for color filter and an ink composition having favorable yellow tone.
• FIG. 1 is a diagram illustrating 1 H NMR spectra of a
• FIG. 2 is a diagram illustrating an SEM photograph of a pigment dispersion (1) containing a compound (1)
• the present inventors have conducted diligent studies to solve the problems of the conventional techniques and consequently found that C.I. Pigment yellow 185 and the compound represented by the formula (1) can be contained in a dispersing medium to thereby yield a pigment dispersion excellent in the dispersibility of the C.I. Pigment yellow 185.
• the present inventors have also found that use of the pigment dispersion can yield a yellow resist composition for color filter and an ink composition that permit image display with high spectral characteristics and display contrast because of their favorable yellow tone. Based on these
• the C.I. Pigment yellow 185 tends to self-aggregate due to its pigment character and is known to be
• pigments such as C.I. Pigment yellow 185
• C.I. Pigment yellow 185 exist in the form of an aggregate having a certain size. Even though only the surface of this aggregate is degraded by the influence of light, the inside of each pigment is insusceptible to light. As a result, the degraded surface portion is likely to function as a protective membrane, enhancing the light resistance of the pigment.
• dyes are dissolved or
• the presence of the compound of the formula (1) can suppress the self-aggregation of the C.I. Pigment yellow 185 and improve its
• the compound of the, formula (1) is incorporated into the fine dispersion of this pigment and thereby protected by the C.I. Pigment yellow 185, which, probably, in turn suppresses the influence of li ht on the compound of the formula (1).
• A represents -S0 2 N(R 4 )R 5 or -CON(R 4 )R 5 wherein R 4 represents a hydrogen atom or an alkyl group, and R 5 represents an alkyl group; Ri represents an alkyl group, an aryl group, or an amino group; R 3 represents a
• R 2 represents (i) a hydrogen atom, a cyano group, or a carbamoyl group provided that R 3 represents a hydrogen atom, or (ii) a hydrogen atom, a cyano group, a carboxylic acid group, a carboxylic acid ester group, a carboxylic acid amide group, or a carbamoyl group provided that R 3 represents an alkyl group, an aryl group, or an aralkyl group.
• Examples of the alkyl group represented by Ri in the formula (1) include, but not particularly limited to, linear or branched alkyl groups having 1 to 20 carbon atoms. Among them, linear or branched alkyl groups having 4 to 12 carbon atoms are preferable in terms of further improvement in the dispersibility of the C.I. Pigment yellow 185 in the dispersing medium. Linear or branched alkyl groups having 6 to 10 carbon atoms are more preferable.
• formula (1) include, but not particularly limited to, 6- to 14-membered monocyclic or polycyclic aryl groups such as phenyl and naphthyl groups . Among them, a phenyl group is preferable.
• Examples of the carboxylic acid ester group represented by R 2 in the formula (1) include, but not particularly limited to, carboxylic acid methyl ester, carboxylic acid ethyl ester, carboxylic acid propyl ester, and carboxylic acid butyl ester groups.
• Examples of the carboxylic acid amide group represented by R 2 in the formula (1) include, but not particularly limited to: mono-substituted amide groups such as.
• R 3 represents a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group. Among them, R 3 is preferably a hydrogen atom or an alkyl group .
• R 2 represents (i) a hydrogen atom, a cyano group, or a carbamoyl group provided that R 3 is a hydrogen atom, or (ii) a hydrogen atom, a cyano group, a carboxylic acid group, a carboxylic acid ester group, carboxylic acid amide group, or a carbamoyl group provided that R3 is an alkyl group, an aryl group, or an aralkyl group.
• formula (1) include, but not particularly limited to, linear or branched alkyl groups having 1 to 20 carbon atoms. Among them, linear or branched alkyl groups having 4 to 12 carbon atoms are preferable in terms of further improvement in the dispersibility of the C.I. Pigment yellow 185 in the dispersing medium. Linear or branched alkyl groups having 6 to 10 carbon atoms are more preferable.
• formula (1) include, but not particularly limited to, 6- to 14-membered monocyclic or polycyclic aryl groups such as phenyl and naphthyl groups. Among them, a phenyl group is preferable.
• Examples of the aralkyl group represented by R 3 in the formula (1) include, but not particularly limited to, benzyl and phenethyl groups.
• A represents -S0 2 N(R 4 )R 5 or -
• R 4 represents a hydrogen atom or an alkyl group
• R5 represents an alkyl group.
• A is preferably -CON(R 4 )R 5 . More preferably, R 4 and R 5 are structurally identical.
• Examples of the alkyl group represented by R 4 or R 5 in the formula (1) include, but not particularly limited to, linear or branched alkyl groups . having 1 to 20 carbon atoms. Among them, linear or branched alkyl groups having 4 to 12 carbon atoms are preferable in terms of further improvement in the dispersibility of the C.I. Pigment yellow 185 in the dispersing medium. Linear or branched alkyl groups having 6 to 10 carbon atoms are more preferable, with a branched ethylhexyl group being further preferable.
• formula (1) of the present invention preferably include, but not limited to, compounds (1) to (26) shown below.
• Et represents an ethyl group
• n-Bu represents a n-butyl group.
• compound represented by the formula (1) is an azo- hydrazo tautomer.
• the hydrazo form is also included in the scope of the present invention.
• Compound (25) Compound (26) 6] he compound represented by the formula (1) for use in the present invention is excellent in coloring power. According to the intended application in which the pigment dispersion of the present invention is used, these compounds may be used alone, or two or more known yellow dyes may be used in combination, in order to adjust tone, etc.
• the pigment dispersion of the present invention is obtained by dispersing at least C.I. Pigment yellow 185 and the compound represented by the formula (1) in a dispersing medium.
• the dispersing medium described in the present invention refers to water, an organic solvent, or a mixture thereof.
• the present invention can be prepared by a known method
• the pigment dispersion of the present invention can be obtained as follows:
• C.I. Pigment yellow 185 and the compound of the formula (1) are added into a dispersing medium, and, if
• a resin is dissolved into the mixture, followed by stirring.
• a mechanical shear force can be further applied thereto using a dispersing machine to prepare a stable and uniform fine dispersion containing fine pigment particles.
• a resin is dissolved into a dispersing medium, and C.I. Pigment yellow 185 is then suspended therein.
• the compound represented by the formula (1) is gradually added to the suspension with stirring and thereby sufficiently blended with the dispersing medium.
• a mechanical shear force may be further applied thereto using a dispersing machine to prepare a stable and uniform fine dispersion containing fine pigment
• the dispersing machine for use in the present invention is not particularly limited.
• a medium- type dispersing machine e.g., a rotary shear
• homogenizer a ball mill, a sand mill, or an attritor
• a high-pressure counter-impact-type dispersing machine is preferably used.
• the C.I. Pigment yellow 185 contains 1.0 to 30.0 parts by mass, preferably 2.0 to 20.0 parts by mass, more preferably 3.0 to 15.0 parts by mass, of the C.I. Pigment yellow 185 with respect to 100 parts by mass of the dispersing medium.
• the content of the C.I. Pigment yellow 185 falls within this range, favorable coloring power can be obtained.
• the compound represented by the formula (1) can be used at preferably 10 to 100 parts by mass, more preferably 10 to 50 parts by mass, with respect to 100 parts by mass of the C.I. Pigment yellow 185.
• the content of the compound falls within this range, favorable dispersibility and coloring power can be obtained while the light degradation of the compound represented by the formula (1) can be suppressed.
• the components can be dispersed in water using an
• emulsifier examples include, but not particularly limited to, cationic surfactants, anionic surfactants, and nonionic surfactants.
• Examples of the cationic surfactants that may be used as the emulsifier for use in the present invention include, but not particularly limited to, dodecyl ammonium chloride, dodecyl ammonium bromide,
• dodecyltrimethyl ammonium bromide dodecyl pyridinium chloride, dodecyl pyridinium bromide, and
• anionic surfactants include: fatty acid soap such as sodium stearate and sodium dodecanoate; and sodium dodecyl sulfate, sodium
• dodecylbenzenesulfonate and sodium lauryl sulfate.
• nonionic surfactants include, but not particularly limited to, polyoxyethylene dodecyl ether, polyoxyethylene hexadecyl ether, polyoxyethylene nonylphenyl ether, polyoxyethylene lauryl ether,
• alcohols such as methyl alcohol, ethyl alcohol, denatured ethyl alcohol, isopropyl alcohol, n-butyl alcohol, isobutyl alcohol, tert-butyl alcohol, sec-butyl alcohol, tert- amyl alcohol, 3-pentanol, octyl alcohol, benzyl alcohol, and cyclohexanol ; glycols such as methyl cellosolve, ethyl cellosolve, diethylene glycol, and diethylene glycol monobutyl ether; ketones such as acetone, methyl ethyl ketone, and methyl isobutyl ketone; esters such as ethyl acetate, butyl acetate, ethyl propionate, and cellosolve acetate; hydrocarbon solvents such as hexane, octane, petroleum
• ethers such as diethyl ether
• dimethyl glycol, trioxane, and tetrahydrofuran dimethyl glycol, trioxane, and tetrahydrofuran
• acetals such as methylal and diethylacetal
• organic acids such as formic acid, acetic acid, . and propionic acid
• sulfur- and nitrogen-containing organic compounds such as nitrobenzene, dimethylamine, monoethanolamine, pyridine, dimethyl sulfoxide, and dimethylformamide .
• a polymerizable monomer may be used as the organic solvent for use in the present invention.
• the polymerizable monomer is an addition-polymerizable or condensation-polymerizable monomer, preferably an addition-polymerizable monomer.
• Specific examples thereof can include: styrene monomers such as styrene, o-methylstyrene, m-methyl-styrene ⁇ p-methy s ' tyrene, o- ethylstyrene, m-ethylstyrene, and p-ethylstyrene;
• acrylate monomers such as methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, octyl acrylate, dodecyl acrylate, stearyl acrylate, behenyl acrylate, 2-ethylhexyl acrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, acrylonitrile, and acrylamide; methacrylate monomers such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, octyl methacrylate, dodecyl
• olefin monomers such as ethylene, propylene, butylene, butadiene, isoprene, isobutylene, and cyclohexene;
• vinyl halides such as vinyl chloride, vinylidene chloride, vinyl bromide, and vinyl iodide
• vinyl esters such as vinyl acetate, vinyl propionate, and vinyl benzoate
• vinyl ethers such as vinyl methyl ether, vinyl ethyl ether, and vinyl isobutyl ether
• vinyl ketone compounds such as vinyl methyl ketone, vinyl hexyl ketone, and methyl isopropenyl ketone.
• polymerized toner application styrene or a styrene monomer, among the polymerizable monomers, is
• the pigment dispersion may be further supplemented with a resin.
• the resin that. may be used in the pigment dispersion is determined according to the intended application thereof and is not particularly limited. Specific examples thereof include polystyrene resins, styrene copolymers, polyacrylic acid resins,
• polymethacrylic acid resins polyacrylic acid ester resins, polymethacrylic acid ester resins, acrylic acid copolymers, methacrylic acid copolymers, polyester resins, polyvinyl ether resins, polyvinylmethyl ether resins, polyvinyl alcohol resins, and polyvinyl butyral resins.
• Other examples thereof include polyurethane resins and polypeptide resins. These resins can be used alone or as a mixture of two or more thereof.
• the pigment dispersion of the present invention can be prepared into an ink composition available as an ink.
• the aqueous dispersing medium is particularly
• a mixed solvent of water and a water-soluble organic solvent may be used.
• the water-soluble organic solvent used is not limited as long as the organic solvent is soluble in water. Examples thereof include alcohols, polyhydric alcohols, polyethylene glycol, glycol ether, nitrogen-containing polar solvents, and sulfur-containing polar solvents.
• the pH of the ink is not particularly limited and is preferably within the range of 4.0 to 11.0 in consideration of safety.
• a solid humectant such as urea, a urea derivative, or
• trimethylolpropane may also be used as a component in the ink in order to maintain ink retention.
• the ink may further contain, in addition to the components described above, various optional additives such as a pH adjuster, a rust preventive, a
• preservative a fungicide, an antioxidant, an anti- reduction agent, an evaporation promoter, a chelating agent, and a water-soluble polymer.
• the present invention is particularly preferably used in an ink jet recoding system which performs recording by ejecting droplets by the action of thermal energy.
• the ink containing the pigment dispersion of the present invention may be used as a material for inks applied to other ink jet
• the pigment dispersion of the present invention has vibrant yellow tone and can be used as a color material for yellow, preferably, a colorant for color filter, because of its spectral characteristics.
• he yellow resist composition of the present invention contain at least one or more pigment dispersions of the present invention. Further, the yellow resist
• composition may contain a binder resin, a
• photopolymerizable monomer a photopolymerization initiator, or a solvent and so on.
• dispersion of the present invention can be used in at least one of these two or more pixels (e.g., red, green, and blue pixels) to thereby provide pixels with high transparency and high color purity.
• the binder resin that can be used in the yellow resist composition for color filter of the present invention is not particularly limited as long as its light- irradiated portion or light-shielded portion is soluble in an organic solvent, an aqueous alkali solution, water, or a commercially available developing solution. More desirably, the binder resin has water- or alkali- developable composition from the viewpoint of
• methacrylic acid 2-hydroxyethyl, acrylamide, N- vinylpyrrolidone, or a monomer having ammonium salt with a lipophilic monomer typified by, for example, acrylic acid ester, methacrylic acid ester, vinyl acetate, styrene, or N-vinylcarbazole at an appropriate mixing ratio by a known approach are generally known as such resins.
• These binder resins can be used as a negative resist, i.e., of a type in which the light- shielded portion is removed by development, in
• radical-polymerizable monomer having an ethylenically unsaturated group a radical-polymerizable monomer having an oxirane or oxetane ring, a radical-generating agent, or an acid- or base- generating agent.
• a binder resin typified by, for example, carbonic acid tert-butyl ester, tert-butyl ester, tetrahydropyranyl ester, or tetrahydropyranyl ether of polyhydroxystyrene may be used.
• This type of binder resin can be used as a positive resist, i.e., of a type in which the light-irradiated portion is removed by development, in combination with an acid-generating agent .
• the yellow resist composition for color filter of the present invention contains a photopolymerizable monomer having one or more ethylenically unsaturated double bond(s) as a monomer having ethylenically unsaturated double bond(s) that is addition-polymerizable by light irradiation.
• the photopolymerizable monomer include compounds each having at least one addition-polymerizable ethylenically unsaturated group in the molecule and having a boiling point of 100°C or higher at ordinary pressure. Examples of such
• compounds can include: monofunctional acrylates and monofunctional metacrylates such as polyethylene glycol monoacrylate, polyethylene glycol monomethacrylate, polypropylene glycol monoacrylate, polypropylene glycol monomethacrylate, phenoxyethyl acrylate, phenoxyethyl methacrylate; polyfunctional acrylates and
• methacrylates such as polyethylene glycol diacrylate, polyethylene glycol dimethacrylate, polypropylene glycol diacrylate, polypropylene glycol dimethacrylate, trimethylolethane triacrylate, trimethylolethane trimethacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, trimethylolpropane diacrylate, trimethylolpropane dimethacrylate,
• pentaerythritol tetramethacrylate pentaerythritol triacrylate, pentaerythritol trimethacrylate,
• dipentaerythritol hexaacrylate dipentaerythritol hexamethacrylate
• dipentaerythritol pentaacrylate dipentaerythritol pentamethacrylate
• acrylates and methacrylates such as urethane acrylates, polyester acrylates, and epoxy acrylates which are reaction products of epoxy resins and acrylic acid or methacrylic acid.
• dipentaerythritol hexaacrylate dipentaerythritol hexamethacrylate
• dipentaerythritol pentaacrylate dipentaerythritol pentamethacrylate
• dipentaerythritol pentamethacrylate is preferable.
• the content of the polymerizable compound is generally 5 to 50% by mass, particularly preferably 10 to 40% by mass, with respect to the mass (total solid content) of the colored photosensitive composition.
• the content less than 5% is not preferable because photosensitivity or pixel intensity may be reduced.
• the content exceeding 50% by mass is not preferable because a photosensitive resin layer may become excessively sticky.
• the yellow resist composition for color filter of the present invention may be ultraviolet curable and, in this case, contains a photopolymerization initiator.
• the photopolymerization initiator include vicinal polyketaldonyl compounds, a-carbonyl compounds, acyloin ether, polynuclear quinone compounds, the combination of triallyl imidazole dimer and p- aminophenyl ketone, and trioxadiazole compounds.
• Preferable examples thereof include 2-benzyl-2- dimethylamino-1- ( -morpholinophenyl ) butanone ( Irgacure 369 (trade name) , manufactured by Ciba Specialty
• the photopolymerization initiator is not essential when electron beam is used in pixel formation using the colored resist of the present invention .
• the yellow resist composition for color filter of the present invention contains a solvent for dissolving or dispersing therein the binder resin, the
• photopolymerizable monomer examples include cyclohexanone, ethyl
• the yellow resist composition for color filter of the present invention contains the pigment dispersion of the present invention as a colorant and can thus achieve the favorable hue of formed pixels and improved transparency and light permeability.
• the compound (5) was structurally determined using a time-of-flight mass spectrometer (TOF-MS) (LC/MSD TOF, manufactured by Agilent Technologies, Inc.) and a nuclear magnetic resonance spectrometer (NMR) (ECA-400, manufactured by JEOL Ltd. ) .
• TOF-MS time-of-flight mass spectrometer
• NMR nuclear magnetic resonance spectrometer
• a compound (20) was obtained by the same procedures as in Example 19 except that the amine compound and pyridone compound of Example 19 were changed to an amine compound (20-1) and a pyridone compound (20-2), respectively.
• Example 5 procedure as in Example 5 except that the compound (5) of Example 5 was changed to .0.7 parts of the compound (6) and ethyl acetate was changed to toluene.
• Example 8 Procedure as in Example 5 except that the compound (5) of Example 5 was changed to 6 parts of the compound (7) and ethyl acetate was changed to methyl ethyl ketone.
• Example 8
• Example 8 procedure as in Example 8 except that the compound (8) of Example 8 was changed to 1.8 parts of the compound
• Example 8 procedure as in Example 8 except that the compound (8) of Example 8 was changed to 4.8 parts of the compound
• Example 11 (11) of Example 11 was changed to 2 parts of the compound (12) and methyl ethyl ketone was changed to styrene .
• Example 13 A pigment dispersion (13) was obtained by the same procedure as in Example 11 except that the compound (11) of Example 11 was changed to 5 parts of the compound (13) and methyl ethyl ketone was changed to styrene .
• a pigment dispersion (14) was obtained by the same procedure as in Example 11 except that the compound (11) of Example 11 was changed to 3 parts of the compound ( 14 ) .
• [0098JA pigment dispersion (15) was obtained by the same procedure as in Example 11 except that the compound (11) of Example 11 was changed to 1 part of the compound (15) and methyl ethyl ketone was changed to styrene .
• a pigment dispersion (16) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was changed to 1.0 part of the compound
• a pigment dispersion (17) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was changed to 2.5 parts of the compound
• Example 28 Following procedure as in Example 1 except that 0.5 parts of the compound (1) of Example 1 was changed to 10 parts thereof .
• Example 28
• Example 28 procedure as in Example 28 except that the compound (20) of Example 28 was changed to 5.0 parts of the compound (21) .
• Example 30 procedure as in Example 30 except that the compound (22) of Example 30 was changed to 3.0 parts of the compound (23) .
• Example 33 A pigment dispersion (33) was obtained by the same procedure as in Example 30 except that the compound (22) of Example 31 was changed to 3.0 parts of the compound (25) .
• Example 34 procedure as in Example 34 except that the compound (26) of Example 34 was changed to 5.0 parts of the compound (27) and styrene was changed to toluene.
• a comparative pigment dispersion (comparison 1) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was not added.
• a pigment dispersion (comparison 2) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was changed to 1 part of a comparative compound (1) and ethyl acetate was changed to toluene. Comparative Example 3
• Example 3 [0113JA pigment dispersion (comparison 3) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was changed to 0.5 parts of a
• a pigment dispersion (comparison 4) was obtained by the same procedure as in Example 1 except that the compound (1) of Example 1 was changed to 2.5 parts of a comparative compound (3) and ethyl acetate was changed to toluene.
• each pigment dispersion was evaluated as follows: the particle size of the pigment was measured using a grind meter (Tester Sangyo Co.,
• each pigment dispersion was evaluated as follows: the pigment dispersion was applied at a film thickness of 4.5 to 5.5 ⁇ onto a film using a bar coater and dried overnight. Its color was measured using a colorimeter and used as an initial value. The light resistance was determined from the level of color change 100 hours later.
• Each pigment dispersion was comprehensively evaluated as follows: a pigment dispersion rated A in the comprehensive evaluation was confirmed to be
• A both dispersibility and light resistance were evaluated as A.
• B at least one of dispersibility and light resistance was evaluated as A.
• Example 20 (1) of Example 20 was changed to the compounds (3), (5), and (10) .
• BASF Japan, Ltd., trade name "PALIOTOL Yellow D 1155" were mixed with 120 parts of styrene and dispersed for 1 hour using an attritor (manufactured by Mitsui Mining Co., Ltd.), and comparative ink was obtained.
• Example 24 The inks prepared in Examples 20 to 23 and 36 to 38 were excellent in the dispersibility of C.I. Pigment yellow 185 and had favorable tone and transparency. By contrast, the inks prepared in Comparative Examples 5, 6, and 7 had the poor dispersibility of C.I. Pigment yellow 185, non-uniform tone, and poor transparency.
• Example 24 The inks prepared in Examples 20 to 23 and 36 to 38 were excellent in the dispersibility of C.I. Pigment yellow 185 and had favorable tone and transparency. By contrast, the inks prepared in Comparative Examples 5, 6, and 7 had the poor dispersibility of C.I. Pigment yellow 185, non-uniform tone, and poor transparency.
• Example 24 Example 24
• Example 3 22 parts of the pigment dispersion (3) obtained in Example 3 were slowly added to a solution containing 6.7 parts of an acrylic copolymer composition, 1.3 parts of dipentaerythritol penta (meth) acrylate, and 0.4 parts of 2-benzyl-2-dimethylamino-l- (4- morpholinophenyl ) -butanone-1 (photopolymerization initiator) in 96 parts of cyclohexanone, and the mixture was stirred at room temperature for 3 hours. This mixture was filtered through a 1.5- ⁇ filter to obtain a yellow resist composition.
• the surface of a glass substrate was spin-coated with the yellow resist composition thus obtained. Then, this coating was dried at 90°C for 3 minutes, and the whole surface thereof was exposed to light. The coating was postcured at 180 °C to prepare a coating sample.
• the obtained coating sample had favorable light permeability and tone.
• composition weight-average molecular weight: 10,000; this acrylic copolymer composition contained n-butyl methacrylate, acrylic acid, and hydroxyethyl
• this coating was dried at 90°C for 3 minutes, and the whole surface thereof was then exposed to light.
• the coating was postcured at 180°C to prepare a color filter.
• Each color filter was obtained by the same procedures as in the above color filter production example except that the compound (2) of Example 24 was changed to the compounds (4), (12), and (15).
• Each color filter was obtained by the same procedures as in the above color filter production example except that the compound (2) of Example 24 was changed to the compounds (20), (22), and (26).
• Each color filter was obtained by the same procedures as in the above color filter production example except that the compound (2) of Example 24 was changed to the comparative compounds (comparison 2) and (comparison 4).

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