WO2022024876A1 - Composition de résine colorée, filtre coloré, dispositif d'affichage d'image et dispersion de colorant - Google Patents

Composition de résine colorée, filtre coloré, dispositif d'affichage d'image et dispersion de colorant Download PDF

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WO2022024876A1
WO2022024876A1 PCT/JP2021/027149 JP2021027149W WO2022024876A1 WO 2022024876 A1 WO2022024876 A1 WO 2022024876A1 JP 2021027149 W JP2021027149 W JP 2021027149W WO 2022024876 A1 WO2022024876 A1 WO 2022024876A1
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Japanese (ja)
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克浩 小川
宏明 石井
直人 東
直也 大村
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三菱ケミカル株式会社
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Priority to JP2022540218A priority Critical patent/JPWO2022024876A1/ja
Priority to CN202180059249.8A priority patent/CN116134379A/zh
Priority to KR1020237002437A priority patent/KR20230044406A/ko
Publication of WO2022024876A1 publication Critical patent/WO2022024876A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
    • C09B67/006—Preparation of organic pigments
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • 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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • 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
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • 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
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G—PHYSICS
    • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
    • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
    • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
    • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements

Definitions

  • the present invention relates to a colored resin composition, a color filter, an image display device, and a colorant dispersion liquid.
  • This application applies to Japanese Patent Application No. 2020-130832 filed in Japan on July 31, 2020, Japanese Patent Application No. 2020-139037 filed in Japan on August 20, 2020, and Japan on August 20, 2020. Claims priority based on Japanese Patent Application No. 2020-139038 filed in Japan, the contents of which are incorporated herein by reference.
  • a pigment dispersion method, a dyeing method, an electrodeposition method, and a printing method are known as methods for manufacturing a color filter used in a liquid crystal display device or the like.
  • the pigment dispersion method having excellent characteristics on average is most widely adopted from the viewpoints of spectral characteristics, durability, pattern shape, accuracy and the like.
  • an object of the present invention is to provide a colored resin composition having high luminance and good contrast.
  • the present invention has the following configurations [1] to [8].
  • a colored resin composition containing (A) a colorant, (B) a solvent, (C) a dispersant, (D) an alkali-soluble resin, and (E) a photopolymerization initiator.
  • the colorant (A) contains a phthalocyanine compound having a chemical structure represented by the following general formula (1).
  • the dispersant (C) contains a dispersant (c1) having an amine value of 50 mgKOH / g or more.
  • a colored resin composition characterized in that the content ratio of the phthalocyanine compound and the dispersant (c1) (phthalocyanine compound / dispersant (c1)) is 5 or more.
  • a 1 to A 16 each independently represents a hydrogen atom, a halogen atom, or a group represented by the following general formula (2). However, 6 or more of A 1 to A 16 are represented. Represents a fluorine atom, and one or more of A 1 to A 16 represents a group represented by the following general formula (2).
  • the dispersant (c1) contains a repeating unit represented by the following general formula (c1-1).
  • the content ratio of the repeating unit represented by the following general formula (c1-2) in the dispersant (c1) is the content ratio of the repeating unit represented by the following general formula (c1-1) and the following general formula (c1-).
  • R 1 and R 2 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may be possessed, and R 1 and R 2 may be bonded to each other to form a cyclic structure.
  • R 3 is a hydrogen atom or a methyl group.
  • X is a divalent linking group.
  • R 6 to R 8 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may have, and two or more of R 6 to R 8 may be bonded to each other to form a cyclic structure.
  • R 9 is a hydrogen atom or a methyl group.
  • Z is a divalent linking group and Y - is a counter anion.
  • a 1 to A 16 each independently represents a hydrogen atom, a halogen atom, or a group represented by the following general formula (2). However, 6 or more of A 1 to A 16 are represented. Represents a fluorine atom, and one or more of A 1 to A 16 represents a group represented by the following general formula (2).
  • X represents a divalent linking group.
  • the benzene ring in the formula (2) may have an arbitrary substituent. * Represents a bond.
  • the dispersant (c1) contains a repeating unit represented by the following general formula (c1-1).
  • the content ratio of the repeating unit represented by the following general formula (c1-2) in the dispersant (c1) is the content ratio of the repeating unit represented by the following general formula (c1-1) and the following general formula (c1-).
  • the colorant dispersion liquid of [6] which is 35 mol% or less with respect to the total content ratio of the repeating unit represented by 2).
  • R 1 and R 2 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may be possessed, and R 1 and R 2 may be bonded to each other to form a cyclic structure.
  • R 3 is a hydrogen atom or a methyl group.
  • X is a divalent linking group.
  • R 6 to R 8 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may have, and two or more of R 6 to R 8 may be bonded to each other to form a cyclic structure.
  • R 9 is a hydrogen atom or a methyl group.
  • Z is a divalent linking group and Y - is a counter anion.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic EL display element having the color filter of the present invention.
  • the "weight average molecular weight” refers to the polystyrene-equivalent weight average molecular weight (Mw) by GPC (gel permeation chromatography).
  • the "amine value” represents an amine value in terms of effective solid content unless otherwise specified, and is a value represented by the amount of base per 1 g of solid content of the dispersant and the equivalent mass of KOH.
  • "CI” means a color index.
  • the “total solid content” means all the components other than the solvent contained in the colored resin composition or the colorant dispersion liquid. Even if the components other than the solvent are liquid at room temperature, the components are not included in the solvent and are included in the total solid content.
  • the colored resin composition according to the present invention comprises (A) a colorant, (B) a solvent, (C) a dispersant, (D) an alkali-soluble resin, and (E) photopolymerization. Contains initiator. Further, if necessary, additives and the like other than the above-mentioned components may be blended.
  • the (A) colorant contained in the colored resin composition of the present invention is a phthalocyanine compound having a chemical structure represented by the following general formula (1) (hereinafter, "phthalocyanine compound (hereinafter,” phthalocyanine compound (hereinafter, “phthalocyanine compound”). It may be referred to as "1)".)
  • a 1 to A 16 independently represent a hydrogen atom, a halogen atom, or a group represented by the following general formula (2). However, 6 or more of A 1 to A 16 represent fluorine atoms, and one or more of A 1 to A 16 represent groups represented by the following general formula (2).
  • X represents a divalent linking group.
  • the benzene ring in the formula (2) may have an arbitrary substituent. * Represents a bond.
  • the (A) colorant contained in the colored resin composition of the present invention contains a phthalocyanine compound.
  • the phthalocyanine compound is sometimes used as a dye, it has been found by the present inventors that it is not sufficiently dissolved in a solvent and aggregates and precipitates over time.
  • the particles of the phthalocyanine compound are aggregated even by heat curing, and the contrast tends to be lowered by light scattering by the generated aggregates.
  • the colored resin composition of the present invention contains a dispersant (c1) having an amine value of 50 mgKOH / g or more.
  • the unshared electron pair of the amine component in the dispersant interacts with the central metal in the phthalocyanine compound (1), so that the dispersant (c1) is efficiently adsorbed on the particles of the phthalocyanine compound (1), and the adsorbed dispersion is performed. It is considered that the steric repulsion between the agents promotes the dispersion stability of the phthalocyanine compound (1), suppresses light scattering due to the generation of agglomerates of particles, and improves the contrast.
  • the phthalocyanine compound (1) has a group represented by the formula (2). Due to the hydrophobic interaction between the group represented by the formula (2) and the dispersant (c1), the dispersant (c1) is more firmly adsorbed on the surface of the phthalocyanine compound (1), and the phthalocyanine compound (c1) in the colored resin composition ( It is considered that the dispersed particle size of 1) becomes smaller, the peak in the transmission spectrum becomes sharper, and the brightness becomes higher.
  • the stability of the phthalocyanine compound itself is determined by the type of substituent of the phthalocyanine skeleton and the number of substituents, and tends to be stable by having a halogen atom as a substituent, particularly a fluorine atom having a large electronegativity, and further depends on the fluorine atom. The larger the number of substituents, the more stable the tendency. It is considered that the high stability of the phthalocyanine compound itself suppresses the aggregation of the compounds in heat curing, thereby suppressing the light scattering due to the generation of aggregates, and the luminance (LY) tends to be less likely to decrease.
  • the phthalocyanine compound (1) has a fluorine atom having a high electronegativity as a substituent, and in particular, since the number of the substituents is 6 or more, the stability of the phthalocyanine compound itself becomes high, and the compounds in heat curing become mutual. It is considered that the light scattering due to the generation of the agglomerates is also suppressed by suppressing the agglomeration of the agglomerates, and the brightness (LY) tends to be less likely to decrease.
  • a 1 to A 16 independently represent a hydrogen atom, a halogen atom, or a group represented by the following general formula (2).
  • 6 or more of A 1 to A 16 represent fluorine atoms
  • one or more of A 1 to A 16 represent groups represented by the following general formula (2).
  • X represents a divalent linking group.
  • the benzene ring in the formula (2) may have an arbitrary substituent. * Represents a bond.
  • Examples of the halogen atom in A 1 to A 16 include a fluorine atom, a chlorine atom, and a bromine atom. Fluorine atoms are preferable from the viewpoint of adjusting the hue to the optimum value as the green dye used in the color filter and increasing the brightness.
  • a 1 to A 16 6 or more represent fluorine atoms, 7 or more are preferable, 8 or more are more preferable, 15 or less, 12 or less are preferable, and 10 or less are more preferable.
  • the stability of the phthalocyanine compound (1) tends to be improved
  • the affinity with the dispersant and the solvent in the colored resin composition is improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of substituents representing a fluorine atom in A 1 to A 16 is 6 to 15, preferably 7 to 12, and more preferably 8 to 10.
  • X in the formula (2) represents a divalent linking group.
  • the divalent linking group is not particularly limited, but is an oxygen atom, a sulfur atom, or a -N (R a1 ) -group (R a1 represents a hydrogen atom or an aliphatic hydrocarbon group having 1 to 6 carbon atoms). Can be mentioned. From the viewpoint of stability of the phthalocyanine compound (1) at the time of baking, an oxygen atom or a sulfur atom is preferable, and an oxygen atom is more preferable.
  • the benzene ring in the formula (2) may have an arbitrary substituent.
  • the substituent is not particularly limited, but is, for example, a halogen atom, an alkyl group ( -RA group), an alkoxy group (-OR A group (where RA represents an alkyl group)), an alkoxycarbonyl group (-COOR).
  • a group (where RA represents an alkyl group)), aryl group (-RB group), aryloxy group (-OR B group (where RB represents an aryl group )), aryloxycarbonyl A group (-COOR B group (where RB represents an aryl group)) is mentioned.
  • An alkoxycarbonyl group is preferable from the viewpoint of affinity with a solvent and brightness.
  • the alkyl group contained in these groups may be linear, branched or cyclic, but is preferably linear from the viewpoint of affinity with the solvent.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is usually preferably 1 or more, 2 or more, preferably 6 or less, more preferably 5 or less, still more preferably 4 or less.
  • the number of carbon atoms of the alkyl group is preferably 1 to 6, more preferably 1 to 5, and even more preferably 2 to 4.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group and the like, and the interaction with the dispersant (c1) is promoted to promote the interaction between the phthalocyanine compounds (1). From the viewpoint of suppressing aggregation, a methyl group or an ethyl group is preferable, and an ethyl group is more preferable.
  • the aryl group contained in these groups may be an aromatic hydrocarbon ring group or an aromatic heterocyclic group.
  • the number of carbon atoms of the aryl group is not particularly limited, but is usually preferably 4 or more and 6 or more, preferably 12 or less, more preferably 10 or less, still more preferably 8 or less.
  • the affinity of the phthalocyanine compound (1) with the solvent tends to be improved, and when it is at least the above upper limit value, the hue change due to the aryl group tends to be suppressed.
  • the above upper limit and lower limit can be arbitrarily combined.
  • the aryl group preferably has 4 to 12 carbon atoms, more preferably 4 to 10 carbon atoms, and even more preferably 6 to 8 carbon atoms.
  • the aromatic hydrocarbon ring in the aromatic hydrocarbon ring group may be a monocyclic ring or a condensed ring.
  • Examples of the aromatic hydrocarbon ring group include a benzene ring, a naphthalene ring, a pentalene ring, an indene ring, an azulene ring, and a heptalene ring having one free valence.
  • the aromatic heterocycle in the aromatic heterocyclic group may be a monocyclic ring or a condensed ring.
  • aromatic heterocyclic group examples include a furan ring, a thiophene ring, a pyrrole ring, a 2H-pyran ring, a 4H-thiopyran ring, a pyridine ring, a 1,3-oxazole ring, and an isooxazole having one free valence.
  • the number of substitutions is not particularly limited, but the phthalocyanine compound (1) stacks ⁇ - ⁇ between molecules to improve heat resistance, and the phthalocyanine compound (1)
  • the number of substitutions is preferably 1 for one benzene ring from the viewpoint of suppressing the decrease in brightness due to the decomposition of).
  • the substitution position may be the o-position, the m-position, or the p-position, but the phthalocyanine compound (1) molecules are ⁇ - ⁇ .
  • the p-position is preferable from the viewpoint of promoting stacking, improving heat resistance, and suppressing a decrease in brightness due to decomposition of the phthalocyanine compound (1).
  • a 1 to A 16 represents a group represented by the formula (2). From the viewpoint of solubility in a solvent and brightness, one or more of A 1 to A 4 are groups represented by the formula (2), and one or more of A 5 to A 8 are represented by the formula (2). It is a group represented, one or more of A 9 to A 12 is a group represented by the formula (2), and one or more of A 13 to A 16 is represented by the formula (2). It is preferable that two or more of A 1 to A 4 are represented by the formula (2), and two or more of A 5 to A 8 are represented by the formula (2). Two or more of A 9 to A 12 are groups represented by the formula (2), and two or more of A 13 to A 16 are groups represented by the formula (2). It is more preferable to have.
  • a 1 to A 16 represent fluorine atoms, but from the viewpoint of stability of the phthalocyanine compound, one or more of A 1 to A 4 are fluorine atoms, and one of A 5 to A 8 It is preferable that one or more are fluorine atoms, one or more of A 9 to A 12 are fluorine atoms, and one or more of A 13 to A 16 are fluorine atoms; A 1 to A 4 Two or more of them are fluorine atoms, two or more of A 5 to A 8 are fluorine atoms, two or more of A 9 to A 12 are fluorine atoms, and A 13 to A 16 It is more preferable that two or more of them are fluorine atoms.
  • a 2 , A 3 , A 6 , A 7 , A 10 , A 11 , A 14 and A 15 are the groups represented by the formula (2), and A 1 , A 4 , A 5 and It is particularly preferable that A 8 , A 9 , A 12 , A 13 and A 16 are fluorine atoms.
  • phthalocyanine compound (1) examples include the following compounds.
  • Et represents ethyl
  • a known method can be adopted, and for example, the method described in Japanese Patent Application Laid-Open No. 05-345861 can be adopted.
  • the colorant may contain other colorants in addition to the phthalocyanine compound (1).
  • Other colorants include pigments and dyes.
  • green pigments, green dyes, yellow pigments, and yellow dyes examples include C.I. I. Pigment Greens 7, 36, 58, 59, 62, 63, and C.I. I. Pigment Green 58 is preferred.
  • the green dyes classified as dyes by the color index C.I. I.
  • a solvent dye for example, C.I. I. Solvent greens 1, 3, 4, 5, 7, 28, 29, 32, 33, 34, 35 can be mentioned.
  • As an acid dye for example, C.I. I.
  • yellow pigment examples include C.I. I. Pigment Yellow 1, 1, 1, 2, 3, 4, 5, 6, 9, 10, 12, 13, 14, 16, 17, 20, 24, 31, 32, 34, 35, 35: 1, 36, 36: 1,37,37: 1,40,41,42,43,48,53,55,61,62,62: 1,63,65,73,74,75,81,83,86,87, 93, 94, 95, 97, 100, 101, 104, 105, 108, 109, 110, 111, 116, 117, 119, 120, 125, 126, 127, 127: 1, 128, 129, 133, 134, 136, 137, 138, 139, 142, 147, 148, 150, 151, 153, 154, 155, 157, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 172, 173, 174, 175, 176, 180, 181, 182, 183, 184
  • Examples of the other compound inserted in the nickel azo complex represented by the formula (i) include a compound represented by the following formula (ii).
  • C.I. I. Pigment Yellow 83, 117, 129, 138, 139, 154, 155, 180, 185, and the nickel azo complex represented by the formula (i) are preferable.
  • I. Pigment Yellow 83, 138, 139, 180, 185 and the nickel azo complex represented by the formula (i) are more preferable.
  • yellow dye examples include barbituric acid azo dyes, pyridone azo dyes, pyrazolone azo dyes, quinophthalone dyes, and cyanine dyes. Specific examples thereof include the specific compounds described in Japanese Patent Application Laid-Open No. 2010-168531.
  • the yellow dyes classified as dyes by the color index C.I. I.
  • a solvent dye for example, C.I. I. Solvent Yellow 4, 14, 15, 23, 24, 38, 62, 63, 68, 79, 82, 94, 98, 99, 162, 163 and the like can be mentioned.
  • acid dye for example, C.I. I.
  • Acid Green 1 3, 5, 9, 16, 25, 27, 50, 58, 63, 65, 80, 104, 105, 106, 109, C.I.
  • Acid Yellow 1 3, 7, 9, 11, 17, 23, 25, 29, 34, 36, 38, 40, 42, 54, 65, 72, 73, 76, 79, 98, 99, 111, 112 , 113, 114, 116, 119, 123, 128, 134, 135, 138, 139, 140, 144, 150, 155, 157, 160, 161, 163, 168, 169, 172, 177, 178, 179, 184.
  • C.I. I. Direct Yellow 2, 33, 34, 35, 38, 39, 43, 47, 50, 54, 58, 68, 69, 70, 71, 86, 93, 94, 95, 98, 102, 108, 109, 129. Examples include the dyes 136, 138 and 141.
  • Examples include dyes of Mordant Yellow 5, 8, 10, 16, 20, 26, 30, 31, 33, 42, 43, 45, 56, 61, 62, 65.
  • the average primary particle size of the pigment is usually 0.2 ⁇ m or less, preferably 0.1 ⁇ m or less, and more preferably 0.04 ⁇ m or less.
  • a method such as solvent salt milling is preferably used.
  • the content ratio of the (A) colorant in the colored resin composition of the present invention is not particularly limited, but is preferably 5% by mass or more, more preferably 10% by mass or more, and 15% by mass in the total solid content of the colored resin composition.
  • the above is further preferable, 20% by mass or more is further preferable, 25% by mass or more is particularly preferable, 70% by mass or less is preferable, 60% by mass or less is more preferable, 50% by mass or less is further preferable, and 45% by mass is 45% by mass.
  • the following is even more preferable, and 40% by mass or less is particularly preferable.
  • the content ratio of the (A) colorant in the colored resin composition is preferably 5 to 70% by mass, more preferably 10 to 60% by mass, and 15 to 50% by mass in the total solid content of the colored resin composition. Even more preferably, 20 to 45% by mass is even more preferable, and 25 to 40% by mass is particularly preferable.
  • the content ratio of the phthalocyanine compound (1) in the colored resin composition of the present invention is not particularly limited, but is preferably 5% by mass or more, more preferably 8% by mass or more, and 10% by mass in the total solid content of the colored resin composition.
  • the above is further preferable, 15% by mass or more is particularly preferable, 45% by mass or less is preferable, 40% by mass or less is more preferable, 35% by mass or less is further preferable, 30% by mass or less is further preferable, and 25% by mass or less is more preferable.
  • the color characteristics such as luminance tend to be improved
  • the pattern formability tends to be improved.
  • the content ratio of the phthalocyanine compound (1) in the colored resin composition is preferably 5 to 45% by mass, more preferably 5 to 40% by mass, and 8 to 35% by mass in the total solid content of the colored resin composition. More preferably, 10 to 30% by mass is even more preferable, and 15 to 25% by mass is particularly preferable.
  • the content ratio (phthalocyanine compound (1) / dispersant (c1)) of the phthalocyanine compound (1) and the dispersant (c1) in the colored resin composition of the present invention is preferably 5 or more, preferably 10 or more. More preferably, 20 or more is further preferable, 30 or more is further preferable, 40 or more is particularly preferable, 150 or less is more preferable, 100 or less is more preferable, and 80 or less is further preferable.
  • the lower limit value or more the pattern characteristics tend to be easily secured, and when it is set to the upper limit value or less, dispersion stability can be ensured and aggregation of the phthalocyanine compound (1) tends to be suppressed.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the phthalocyanine compound (1) and the dispersant (c1) in the colored resin composition is preferably 5 to 150, more preferably 10 to 150, still more preferably 20 to 100, and 30 to 30. 100 is even more preferred, and 40-80 is particularly preferred.
  • the content ratio of the phthalocyanine compound (1) in the colored resin composition of the present invention is not particularly limited, but is preferably 500 parts by mass or more, more preferably 1000 parts by mass or more, and 2000 parts by mass with respect to 100 parts by mass of the dispersant (c1). More than parts are more preferable, 3000 parts by mass or more are further preferable, 4000 parts by mass or more are particularly preferable, 15,000 parts by mass or less are preferable, 10,000 parts by mass or less are more preferable, and 8,000 parts by mass or less are further preferable.
  • the content ratio of the phthalocyanine compound (1) in the colored resin composition is preferably 500 to 15,000 parts by mass, more preferably 1,000 to 15,000 parts by mass, and 2,000 to 10,000 parts by mass with respect to 100 parts by mass of the dispersant (c1). Is even more preferable, and 3000 to 10000 parts by mass is even more preferable, and 4000 to 8000 parts by mass is particularly preferable.
  • the content ratio thereof is not particularly limited, but is preferably 1% by mass or more, more preferably 5% by mass or more, still more preferably 8% by mass or more in the total solid content of the colored resin composition. 10% by mass or more is more preferable, 15% by mass or more is particularly preferable, 40% by mass or less is more preferable, 35% by mass or less is more preferable, 30% by mass or less is further preferable, and 25% by mass or less is particularly preferable.
  • the lower limit value or more thermal decomposition during hot firing at the time of producing a color filter tends to be suppressed, and when it is set to the upper limit value or less, the pattern forming property tends to be improved.
  • the content ratio thereof is preferably 1 to 40% by mass, more preferably 5 to 40% by mass, and further preferably 8 to 35% by mass in the total solid content of the colored resin composition.
  • 10 to 30% by mass is even more preferable, and 15 to 25% by mass is particularly preferable.
  • (B) Solvent
  • the solvent (B) dissolves or dissolves a colorant, a dispersant, an alkali-soluble resin, a photopolymerization initiator, and other components in the colored resin composition and the colorant dispersion liquid of the present invention. It has the function of dispersing and adjusting the viscosity.
  • the solvent may be any solvent that can dissolve or disperse each component.
  • Examples of such a solvent include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, and propylene glycol mono-n-butyl ether.
  • Propropylene glycol-t-butyl ether diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, methoxymethylpentanol, propylene glycol monoethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl Glycol monoalkyl ethers such as -3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, tripropylene glycol methyl ether;
  • Glycoldialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dipropyl ether, diethylene glycol dibutyl ether, dipropylene glycol dimethyl ether; Ethylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate, ethylene glycol mono-n-butyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate, propylene glycol monobutyl ether acetate, methoxybutyl Acetate, 3-methoxybutyl acetate, methoxypentyl acetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol mono-n
  • Glycol diacetates such as ethylene glycol diacetate, 1,3-butylene glycol diacetate, 1,6-hexanol diacetate; Alkyl acetates such as cyclohexanol acetate; Ethers such as amyl ether, propyl ether, diethyl ether, dipropyl ether, diisopropyl ether, butyl ether, diamil ether, ethylisobutyl ether, dihexyl ether; Like acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methylhexyl ketone, methyl
  • Ketones Monohydric or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol, triethylene glycol, methoxymethylpentanol, glycerin, benzyl alcohol; Aliphatic hydrocarbons such as n-pentane, n-octane, diisobutylene, n-hexane, hexene, isoprene, dipentene, dodecane; Alicyclic hydrocarbons such as cyclohexane, methylcyclohexane, methylcyclohexene, bicyclohexyl;
  • Aromatic hydrocarbons such as benzene, toluene, xylene, cumene; Amilformate, ethylformate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methylisobutyrate, ethylene glycol acetate, ethylpropionate, propylpropionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl Caprilate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3-methoxypropionate Chain or cyclic esters such as butyl, ⁇ -butyrolactone; Alkoxycarboxylic acids such as 3-methoxypropi
  • solvents examples include mineral spirit, balsol # 2, apco # 18 solvent, apco thinner, and socal solvent No. 1 and No. 2.
  • Solvento # 150 Shell TS28 solvent, carbitol, ethyl carbitol, butyl carbitol, methyl cellosolve, ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve acetate, diglyme (all are trade names). These solvents may be used alone or in combination of two or more.
  • a solvent having a boiling point in the range of 100 to 200 ° C. pressure 1013.25 [hPa] conditions; hereinafter, the boiling points are all the same
  • the solvent is selected as the solvent.
  • it is a solvent having a boiling point of 120 to 170 ° C.
  • Glycol alkyl ether acetates are preferable because they have a good balance of coatability, surface tension, etc. in the solvent and the solubility of the constituents in the composition is relatively high.
  • Glycol alkyl ether acetates may be used alone or in combination with other solvents.
  • Glycol monoalkyl ethers are particularly preferable as the solvent to be used in combination.
  • propylene glycol monomethyl ether is particularly preferable from the viewpoint of the solubility of the constituents in the composition.
  • Glycol monoalkyl ethers have high polarity, and if the amount added is too large, the pigment tends to aggregate, and the viscosity of the colored resin composition obtained later tends to increase, and the storage stability tends to decrease.
  • the content ratio of the glycol monoalkyl ethers in the solvent (B) is preferably 5% by mass to 30% by mass, more preferably 5% by mass to 20% by mass.
  • a solvent having a boiling point of 150 ° C. or higher can be used in combination.
  • the colored resin composition becomes difficult to dry, but it has an effect of making it difficult to destroy the mutual relationship of the constituents in the pigment dispersion liquid due to rapid drying. ..
  • the content ratio of the solvent having a boiling point of 150 ° C. or higher in (B) is preferably 3% by mass to 50% by mass, preferably 5% by mass to 40% by mass. Is more preferable, and 5% by mass to 30% by mass is particularly preferable.
  • the solvent having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates or glycol alkyl ethers, and in this case, it is not necessary to separately contain a solvent having a boiling point of 150 ° C. or higher. As the solvent having a boiling point of 150 ° C.
  • diethylene glycol mono-n-butyl ether acetate diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,6-hexanol diacetate are preferable.
  • Triacetin Triacetin.
  • a solvent having a boiling point of usually 130 ° C. or higher and 300 ° C. or lower, preferably 150 ° C. or higher and 280 ° C. or lower is suitable.
  • the uniformity of the obtained coating film tends to be good, and when it is at least the above upper limit value, there is a tendency that the residual solvent at the time of firing is easily reduced.
  • the vapor pressure of the solvent is usually 10 mmHg or less, preferably 5 mmHg or less, and more preferably 1 mmHg or less.
  • the ink emitted from the nozzle is extremely fine, ranging from several to several tens of pL, so the solvent evaporates and the ink concentrates and dries before landing around the nozzle opening or in the pixel bank. Tends to harden.
  • the solvent (B) contains a solvent having a high boiling point, and specifically, it is preferable to contain a solvent having a boiling point of 180 ° C. or higher. It is more preferable to contain a solvent having a boiling point of 200 ° C. or higher, and it is particularly preferable to contain a solvent having a boiling point of 220 ° C. or higher.
  • the content ratio of the solvent having a boiling point of 180 ° C. or higher in the solvent (B) is preferably 50% by mass or more, preferably 70% by mass. The above is more preferable, and 90% by mass or more is most preferable. By setting the value to the lower limit or more, the effect of preventing evaporation of the solvent from the droplets tends to be sufficiently exhibited.
  • a solvent having a boiling point of 180 ° C. or higher for example, among the various solvents mentioned above, diethylene glycol mono-n-butyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, 1,6- Hexanol diacetate, triacetin and the like can be mentioned.
  • a solvent having a boiling point lower than 180 ° C. may be contained for adjusting the viscosity of the colored resin composition and adjusting the solubility of the solid content.
  • a solvent having low viscosity, high solubility, and low surface tension is preferable, and for example, ethers, esters, and ketones are preferable.
  • ethers, esters, and ketones are preferable.
  • cyclohexanone, dipropylene glycol dimethyl ether, and cyclohexanol acetate are preferable.
  • the ejection stability in the inkjet method may deteriorate.
  • the content ratio of alcohols in the solvent (B) is preferably 20% by mass or less, more preferably 10% by mass or less, and particularly preferably 5% by mass or less.
  • the content ratio of the solvent in the colored resin composition of the present invention is not particularly limited, but the upper limit thereof is usually 99% by mass or less, preferably 90% by mass or less, and more preferably 85% by mass or less. When the value is not more than the upper limit, the coating film tends to be easily formed.
  • the lower limit of the solvent content ratio is usually 70% by mass or more, preferably 75% by mass or more, and more preferably 78% by mass or more in consideration of viscosity suitable for coating.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the solvent in the colored resin composition is preferably 70 to 99% by mass, more preferably 75 to 90% by mass, still more preferably 78 to 85% by mass.
  • the colored resin composition of the present invention and the colorant dispersion liquid of the present invention contain (C) a dispersant for the purpose of stably dispersing (A) the colorant.
  • the dispersant (C) in the colored resin composition of the present invention contains a dispersant (c1) having an amine value of 50 mgKOH / g or more (hereinafter, may be referred to as "dispersant (c1)"), and is the present invention.
  • the dispersant (C) in the colorant dispersion liquid of No. 1 preferably contains a dispersant (c1).
  • the dispersant (c1) By containing the dispersant (c1), the dispersant (c1) becomes the phthalocyanine compound (1) due to the interaction between the unshared electron pair of the amine component in the dispersant (c1) and the central metal of the phthalocyanine compound (1).
  • the dispersion stability of the phthalocyanine compound (1) is promoted by the steric repulsion between the adsorbed dispersants, the light scattering due to the generation of agglomerates of the particles is suppressed, and the contrast is improved. It is considered to be good.
  • the amine value of the dispersant (c1) is 50 mgKOH / g or more, preferably 60 mgKOH / g or more, more preferably 70 mgKOH / g or more, further preferably 80 mgKOH / g or more, still more preferably 90 mgKOH / g or more, and 100 mgKOH / g.
  • G or more is particularly preferable, 110 mgKOH / g or more is most preferable, 200 mgKOH / g or less is preferable, 180 mgKOH / g or less is more preferable, 160 mgKOH / g or less is further preferable, and 140 mgKOH / g or less is particularly preferable.
  • Dispersion stability can be ensured by setting the value to the lower limit or higher, and aggregation of the phthalocyanine compound (1) tends to be suppressed. It tends to be easy.
  • the above upper and lower limits can be combined arbitrarily.
  • the amine value of the dispersant (c1) is preferably 50 to 200 mgKOH / g, more preferably 60 to 200 mgKOH / g, even more preferably 70 to 180 mgKOH / g, even more preferably 80 to 180 mgKOH / g, and even more preferably 90 to 160 mgKOH.
  • / G is even more preferable, 100 to 160 mgKOH / g is particularly preferable, and 110 to 140 mgKOH / g is most preferable.
  • the chemical structure of the dispersant (c1) is not particularly limited, but the unshared electron pair of the amine component of the phthalocyanine compound (1) and the dispersant (c1) interact with each other to promote dispersion stability and suppress particle aggregation. Therefore, it is preferable to have a repeating unit represented by the following general formula (c1-1) (hereinafter, may be referred to as “repeating unit (c1-1)”).
  • R 1 and R 2 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may be used, and R 1 and R 2 may be bonded to each other to form a cyclic structure.
  • R 3 is a hydrogen atom or a methyl group.
  • X is a divalent linking group.
  • R 1 and R 2 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an Aralkyl group that may be used.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is usually 1 or more, preferably 10 or less, more preferably 6 or less, still more preferably 4 or less, still more preferably 3 or less, from the viewpoint of dispersibility. The following are particularly preferred.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 6, further preferably 1 to 4, further preferably 1 to 3, and particularly preferably 1 to 2.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group.
  • Methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are preferable, and methyl group, ethyl group, propyl group and butyl group are more preferable.
  • These alkyl groups may be linear or branched.
  • These alkyl groups may contain a cyclic structure such as, for example, a cyclohexyl group and a cyclohexylmethyl group.
  • the number of carbon atoms of the aryl group is not particularly limited, but is usually 6 or more, preferably 16 or less, more preferably 12 or less, further preferably 10 or less, and particularly preferably 8 or less, from the viewpoint of dispersibility.
  • the aryl group preferably has 6 to 16 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6 to 10 carbon atoms, and particularly preferably 6 to 8 carbon atoms.
  • Examples of the aryl group include a phenyl group, a naphthyl group, and an anthrasenyl group. Phenyl groups are preferred.
  • the carbon number of the aralkyl group is not particularly limited, but is usually 7 or more, preferably 16 or less, more preferably 12 or less, further preferably 10 or less, and particularly preferably 8 or less, from the viewpoint of dispersibility.
  • the carbon number of the aralkyl group is preferably 7 to 16, more preferably 7 to 12, further preferably 7 to 10, and particularly preferably 7 to 8.
  • the aralkyl group include a phenylmethyl group (benzyl group), a phenylethyl group (phenethyl group), a phenylpropyl group, a phenylbutyl group and a phenylisopropyl group.
  • a phenylmethyl group, a phenylethyl group, a phenylpropyl group and a phenylbutyl group are preferable, and a phenylmethyl group and a phenylethyl group are more preferable.
  • R 1 and R 2 are each independently an alkyl group which may have a substituent, and a methyl group and an ethyl group are used. It is more preferable to have.
  • Examples of the substituent that the alkyl group, aralkyl group, and aryl group in R 1 and R 2 of the formula (c1-1) may have include a halogen atom, an alkoxy group, a benzoyl group, and a hydroxyl group.
  • the cyclic structure formed by bonding R 1 and R 2 to each other includes, for example, a nitrogen-containing heterocyclic monocycle having a 5- to 7-membered ring or a condensed ring formed by condensing two of them.
  • the nitrogen-containing heterocycle is preferably one having no aromaticity, and more preferably a saturated ring.
  • the following annular structure can be mentioned.
  • These cyclic structures may further have a substituent.
  • the divalent linking group X includes, for example, an alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms, a -CONH-R 4 -group, and a -COOR 5 -group.
  • R 4 and R 5 are each independently a single bond, an alkylene group having 1 to 10 carbon atoms, or an ether group having 2 to 10 carbon atoms (alkyloxyalkyl group)), which is preferable.
  • Is -COO-R 5 -group an alkylene group is preferable, an alkylene group having 1 to 5 carbon atoms is more preferable, and an alkylene group having 1 to 3 carbon atoms is further preferable, from the viewpoint of dispersibility.
  • the dispersant (c1) is a repeating unit represented by the following general formula (c1-2) from the viewpoint that the electrostatic interaction with the phthalocyanine compound (1) is promoted and the stability of the dispersion with time is improved.
  • it may be referred to as a “repeating unit (c1-2)”).
  • R 6 to R 8 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group which may be used, and two or more of R 6 to R 8 may be bonded to each other to form a cyclic structure.
  • R 9 is a hydrogen atom or a methyl group.
  • Z is a divalent linking group and Y - is a counter anion.
  • R 6 to R 8 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent. It is an aralkyl group that may have.
  • the number of carbon atoms of the alkyl group is not particularly limited, but is usually 1 or more, preferably 10 or less, more preferably 6 or less, still more preferably 4 or less, still more preferably 3 or less, from the viewpoint of dispersibility. The following are particularly preferred.
  • the number of carbon atoms of the alkyl group is preferably 1 to 10, more preferably 1 to 6, further preferably 1 to 4, further preferably 1 to 3, and particularly preferably 1 to 2.
  • alkyl group examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group.
  • Methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are preferable, and methyl group, ethyl group, propyl group and butyl group are more preferable.
  • These alkyl groups may be linear or branched.
  • These alkyl groups may contain a cyclic structure such as a cyclohexyl group and a cyclohexylmethyl group.
  • the number of carbon atoms of the aryl group is not particularly limited, but is usually 6 or more, preferably 16 or less, more preferably 12 or less, further preferably 10 or less, and particularly preferably 8 or less, from the viewpoint of dispersibility.
  • the aryl group preferably has 6 to 16 carbon atoms, more preferably 6 to 12 carbon atoms, still more preferably 6 to 10 carbon atoms, and particularly preferably 6 to 8 carbon atoms.
  • Examples of the aryl group include a phenyl group, a naphthyl group, and an anthrasenyl group. Phenyl groups are preferred.
  • the carbon number of the aralkyl group is not particularly limited, but is usually 7 or more, preferably 16 or less, more preferably 12 or less, further preferably 10 or less, and particularly preferably 8 or less, from the viewpoint of dispersibility.
  • the carbon number of the aralkyl group is preferably 7 to 16, more preferably 7 to 12, further preferably 7 to 10, and particularly preferably 7 to 8.
  • the aralkyl group include a phenylmethyl group (benzyl group), a phenylethyl group (phenethyl group), a phenylpropyl group, a phenylbutyl group and a phenylisopropyl group.
  • a phenylmethyl group, a phenylethyl group, a phenylpropyl group and a phenylbutyl group are preferable, and a phenylmethyl group and a phenylethyl group are more preferable.
  • R 6 to R 8 are independently alkyl groups or aralkyl groups; R 6 and R 8 are independently methyl groups, respectively. Alternatively, it is preferably an ethyl group and R 7 is a phenylmethyl group (benzyl group) or a phenylethyl group (phenethyl group); R 6 and R 8 are methyl groups and R 7 is a phenyl group. It is more preferably a methyl group.
  • Examples of the substituent that the alkyl group, aralkyl group, and aryl group in R 6 to R 8 of the formula (c1-2) may have include a halogen atom, an alkoxy group, a benzoyl group, and a hydroxyl group.
  • the cyclic structure formed by bonding two or more of R 6 to R 8 to each other is, for example, a nitrogen-containing heterocyclic monocycle having a 5- to 7-membered ring, and two of them are condensed. Condensation ring is mentioned.
  • the nitrogen-containing heterocycle is preferably one having no aromaticity, and more preferably a saturated ring.
  • the following annular structure can be mentioned.
  • R is any of R 6 to R 8 . These cyclic structures may further have substituents.
  • Y- ( Y- )
  • the counter anion Y- for example, Cl- , Br- , I- , ClO 4- , BF 4- , CH 3 COO- , SO 3- , PF 6- , aromatic.
  • examples thereof include dicarboxylic acid imide anions, aromatic sulfonic acids, anions, aromatic phosphonate anions, and aromatic carboxylic acid anions.
  • the content ratio thereof is not particularly limited, but 10 mol% or more is preferable, and 12 mol% or more is more preferable in all the repeating units. , 15 mol% or more is further preferable, 17 mol% or more is further preferable, 20 mol% or more is particularly preferable, 22 mol% or more is particularly preferable, 24 mol% or more is most preferable, and 45 mol% or less is particularly preferable. It is preferably 40 mol% or less, more preferably 38 mol% or less, and particularly preferably 35 mol% or less.
  • the content ratio of the repeating unit represented by the formula (c1-1) is preferably 10 to 45 mol%, more preferably 12 to 45 mol%, and 15 to 40 in all the repeating units in the dispersant (c1). More preferably, 17-40 mol%, even more preferably 20-38 mol%, particularly preferably 22-38 mol%, most preferably 24-35 mol%.
  • the content ratio thereof is not particularly limited, but is preferably 40 mol% or less, more preferably 30 mol% or less, and 20 mol% or less. Is more preferable, and 10 mol% or less is particularly preferable, and usually 1 mol% or more.
  • the value By setting the value to the upper limit or less, aggregation of the phthalocyanine compounds (1) is suppressed and the contrast tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the repeating unit represented by the formula (c1-2) is preferably 1 to 40 mol%, more preferably 1 to 30 mol%, and 1 to 20 in all the repeating units in the dispersant (c1). More preferably, 1-10 mol% is particularly preferred.
  • the content ratio of the repeating unit represented by the formula (c1-2) in the dispersant (c1) is not particularly limited. 35 mol% or less is preferable, and 20 mol% or less is more preferable to the total of the content ratio of the repeating unit represented by the formula (c1-1) and the content ratio of the repeating unit represented by the formula (c1-2). It is preferable, 10 mol% or less is more preferable, and 5 mol% or less is particularly preferable. Most preferably, it is 0 mol%. By setting the value to the upper limit or less, aggregation of the phthalocyanine compounds (1) is suppressed and the contrast tends to be improved.
  • the dispersant (c1) is a repeating unit represented by the following general formula (c1-3) from the viewpoint of increasing the compatibility of the dispersant with a binder component such as a solvent and improving the dispersion stability (hereinafter, “repetition”). It may be referred to as “unit (c1-3)").
  • R 10 is an ethylene group or a propylene group
  • R 11 is an alkyl group which may have a substituent
  • R 12 is a hydrogen atom or a methyl group.
  • n is an integer from 1 to 20.
  • the carbon number of the alkyl group in R 11 of the formula (c1-3) is not particularly limited, but is usually 1 or more, preferably 10 or less, and more preferably 6 or less.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
  • Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group.
  • Methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are preferable, and methyl group, ethyl group, propyl group and butyl group are more preferable.
  • These alkyl groups may be linear or branched. These alkyl groups may contain a cyclic structure such as a cyclohexyl group and a cyclohexylmethyl group. Examples of the substituent that the alkyl group in R 11 may have include a halogen atom, an alkoxy group, a benzoyl group, and a hydroxyl group.
  • n in the formula (c1-3) is preferably 1 or more, more preferably 2 or more, and preferably 10 or less. It is preferably 5 or less, and more preferably 5 or less.
  • n is preferably 1 to 10, more preferably 2 to 5.
  • the content ratio thereof is not particularly limited, but 2 mol% or more is preferable and 4 mol% or more is more preferable in all the repeating units. , 6 mol% or more is further preferable, 8 mol% or more is particularly preferable, 50 mol% or less is preferable, 40 mol% or less is more preferable, 30 mol% or less is further preferable, and 20 mol% or less is further preferable. 10 mol% or less is particularly preferable.
  • the value is at least the above lower limit, the solubility of the dispersant in the solvent tends to increase, and the affinity of the phthalocyanine compound (1) for the solvent tends to increase.
  • the dispersant When the value is at least the above upper limit, the dispersant is dispersed in the solvent. The diffusion of the agent (c1) is suppressed, and the adsorption on the surface of the phthalocyanine compound (1) tends to be promoted.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the repeating unit represented by the formula (c1-3) is preferably 2 to 50 mol%, more preferably 2 to 40 mol%, and 4 to 30 in all the repeating units in the dispersant (c1). Mol% is even more preferred, 6-20 mol% is even more preferred, and 8-10 mol% is particularly preferred.
  • the dispersant (c1) is a repeating unit represented by the following general formula (c1-4) (hereinafter, “repeating unit”) from the viewpoint of increasing the compatibility of the dispersant with the solvent and the binder component and improving the dispersion stability. (C1-4) "may be referred to.).
  • R 13 is an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent.
  • R 14 is a hydrogen atom or a methyl group.
  • the carbon number of the alkyl group in R13 of the formula (c1-4) is not particularly limited, but is usually 1 or more, preferably 1 or more, preferably 10 or less, and 6 or less. Is more preferable.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms.
  • Examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group and an octyl group.
  • Methyl group, ethyl group, propyl group, butyl group, pentyl group and hexyl group are preferable, and methyl group, ethyl group, propyl group and butyl group are more preferable.
  • These alkyl groups may be linear or branched. These alkyl groups may contain a cyclic structure such as a cyclohexyl group and a cyclohexylmethyl group.
  • the carbon number of the aryl group in R13 of the formula (c1-4) is not particularly limited, but is usually 6 or more, preferably 6 or more, preferably 16 or less, and more preferably 12 or less.
  • the aryl group preferably has 6 to 16 carbon atoms, more preferably 6 to 12 carbon atoms.
  • Examples of the aryl group include a phenyl group, a naphthyl group, and an anthrasenyl group. Phenyl groups are preferred.
  • the number of carbon atoms of the aralkyl group which may have a substituent in R 13 of the formula (c1-4) is not particularly limited, but is usually 7 or more, preferably 7 or more, preferably 16 or less, and 12 or less. The following are more preferable.
  • the aralkyl group preferably has 7 to 16 carbon atoms, more preferably 7 to 12 carbon atoms.
  • Examples of the aralkyl group include a phenylmethyl group, a phenylethyl group, a phenylpropyl group, a phenylbutyl group and a phenylisopropyl group.
  • a phenylmethyl group, a phenylethyl group, a phenylpropyl group and a phenylbutyl group are preferable, and a phenylmethyl group and a phenylethyl group are more preferable.
  • R 13 is preferably an alkyl group or an aralkyl group, and more preferably a methyl group, an ethyl group or a phenylmethyl group.
  • substituents that the alkyl group may have in R 13 include a halogen atom and an alkoxy group.
  • the substituent that the aryl group and the aralkyl group may have include an alkyl group, a halogen atom, and an alkoxy group.
  • the content ratio thereof is not particularly limited, but 1 mol% or more is preferable and 10 mol% or more is more preferable in all the repeating units. , 20 mol% or more is further preferable, 30 mol% or more is further preferable, 40 mol% or more is particularly preferable, 90 mol% or less is preferable, 85 mol% or less is more preferable, and 80 mol% or less is further preferable. , 70 mol% or less is particularly preferable.
  • the content ratio of the repeating unit represented by the formula (c1-4) is preferably 1 to 90 mol%, more preferably 10 to 90 mol%, and 20 to 85 in all the repeating units in the dispersant (c1). Mol% is even more preferred, 30-80 mol% is even more preferred, and 40-70 mol% is particularly preferred.
  • the dispersant (c1) may have a repeating unit other than the repeating unit (c1-1), the repeating unit (c1-2), the repeating unit (c1-3) and the repeating unit (c1-4).
  • Such repeating units include, for example, styrene-based monomers such as styrene and ⁇ -methylstyrene; (meth) acrylate-based monomers such as (meth) acrylic acid chloride; (meth) acrylamide, N- Examples thereof include (meth) acrylamide-based monomers such as methylolacrylamide; vinyl acetate; acrylonitrile; allylglycidyl ether; glycidyl crotonate ether; and repeating units derived from N-methacryloylmorpholine.
  • the dispersant (c1) is an A block having a repeating unit (c1-1) and a repeating unit (c1-2), and a repeating unit (c1-1) and a repeating unit (c1) from the viewpoint of further enhancing dispersibility.
  • -2) It is preferable that it is a block copolymer having a B block having no B block.
  • the block copolymer include an AB block copolymer, a BAB block copolymer, and an ABA block copolymer.
  • the B block has a repeating unit (c1-3), and more preferably it has a repeating unit (c1-4).
  • the repeating unit (c1-1) and the repeating unit (c1-2) may be contained in any mode of random copolymerization or block copolymerization. Further, two or more repeating units (c1-1) and repeating units (c1-2) may be contained in one A block, and in that case, each repeating unit is random in the A block. It may be contained in any aspect of copolymerization or block copolymerization.
  • a repeating unit other than the repeating unit (c1-1) and the repeating unit (c1-2) may be contained in the A block.
  • Examples of such a repeating unit include a repeating unit derived from a (meth) acrylic acid ester-based monomer described later.
  • the content of the repeating unit other than the repeating unit (c1-1) and the repeating unit (c1-2) in the A block is preferably 0 to 50 mol%, more preferably 0 to 20 mol%. It is most preferable that the repeating unit other than the repeating unit (c1-1) and the repeating unit (c1-2) is not contained in the A block.
  • a repeating unit other than the repeating unit (c1-3) and the repeating unit (c1-4) may be contained in the B block.
  • Such repeating units include, for example, styrene-based monomers such as styrene and ⁇ -methylstyrene; (meth) acrylate-based monomers such as (meth) acrylic acid chloride; (meth) acrylamide, N- Examples thereof include (meth) acrylamide-based monomers such as methylolacrylamide; vinyl acetate; acrylonitrile; allylglycidyl ether; glycidyl crotonate ether; and repeating units derived from N-methacryloylmorpholine.
  • the content of the repeating unit other than the repeating unit (c1-3) and the repeating unit (c1-4) in the B block is preferably 0 to 50 mol%, more preferably 0 to 20 mol%, but is repeated. It is most preferable that the repeating unit other than the unit (c1-3) and the repeating unit (c1-4) is not contained in the B block.
  • the acid value of the dispersant (c1) is not particularly limited, but the viewpoint is to suppress the reaction between the amine component (adsorption group) of the dispersant (c1) and the acid to inhibit the adsorption of the phthalocyanine compound (1) on the surface. Therefore, a lower value is preferable, 50 mgKOH / g or less is preferable, and 30 mgKOH / g or less is preferable, and 0 mgKOH / g is particularly preferable.
  • the weight average molecular weight of the dispersant (c1) is not particularly limited, but 4000 or more is preferable, 5000 or more is more preferable, 6000 or more is further preferable, 12000 or less is preferable, 10,000 or less is more preferable, and 9000 or less is further preferable. ..
  • the weight average molecular weight of the dispersant (c1) is preferably 4000 to 12000, more preferably 5000 to 10000, and even more preferably 6000 to 9000.
  • the dispersant (c1) can be produced by a known method.
  • the dispersant (c1) is a block copolymer, it can be produced, for example, by subjecting the monomer into which each of the above repeating units is introduced to living polymerization.
  • the living polymerization method include Japanese Patent Application Laid-Open No. 9-62002, Japanese Patent Application Laid-Open No. 2002-31713, and P.M. Lutz, P. et al. Masson et al, Polym. Bull. 12, 79 (1984), B.I. C. Anderson, G.M. D. Andrews et al, Macromolecules, 14, 1601 (1981), K. et al. Hatada, K. et al.
  • Examples of the monomer for introducing the repeating unit (c1-1) used in producing the dispersant (c1) include dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, and dimethylaminopropyl (meth). Examples thereof include acrylate and diethylaminopropyl (meth) acrylate.
  • Examples of the monomer for introducing the repeating unit (c1-2) include (meth) acryloylaminopropyltrimethylammonium chloride, (meth) acryloyloxyethyltrimethylammonium chloride, (meth) acryloyloxyethyltriethylammonium chloride, and (meth) acryloyloxyethyltriethylammonium chloride.
  • Examples of the monomer for introducing the repeating unit (c1-4) include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, butyl (meth) acrylate, and 2-.
  • Examples thereof include ethylhexyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, dicyclopentanyl (meth) acrylate, isobornyl (meth) acrylate, benzyl (meth) acrylate, and phenylethyl (meth) acrylate.
  • one type of dispersant (c1) may be used alone, or two or more types may be used in combination.
  • another dispersant (c2) can be used in combination with the dispersant (c1).
  • dispersants (c2) as commercial products, for example, Disperbyk (registered trademark; the same applies hereinafter) -161, Disperbyk-162, Disperbyk-165, Disperbyk-167, Disperbyk-170, Disperbyk-182, Disperbyk- 2000, Disperbyk-2001 (above, manufactured by Big Chemie (BYK)), Solsperth (registered trademark; the same shall apply hereinafter) 24000, Solsperth 76500 (manufactured by Lubrizol Co., Ltd.), Azisper (registered trademark; the same shall apply hereinafter) PB821, Examples thereof include Ajispar PB822, Ajispar PB823, Ajispar PB824, and Ajisper PB827 (manufactured by Ajinomoto Fine-Techno Co., Ltd
  • the content ratio of the (C) dispersant in the colored resin composition of the present invention is not particularly limited, but is preferably 0.5 parts by mass or more, more preferably 1 part by mass or more with respect to 100 parts by mass of the (A) colorant. 1.5 parts by mass or more is further preferable, 5 parts by mass or less is preferable, 4 parts by mass or less is more preferable, 3 parts by mass or less is further preferable, and 2.5 parts by mass or less is particularly preferable.
  • the dispersion stability of the phthalocyanine compound (1) tends to be improved and the contrast tends to be improved
  • it tends to be easy to secure the pattern characteristics.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the (C) dispersant in the colored resin composition is preferably 0.5 to 5 parts by mass, more preferably 0.5 to 4 parts by mass with respect to 100 parts by mass of the (A) colorant. It is more preferably 3 parts by mass, and particularly preferably 1.5 to 2.5 parts by mass.
  • the content ratio of the dispersant (C) in the colored resin composition of the present invention is not particularly limited, but is preferably 0.05% by mass or more, more preferably 0.1% by mass or more, and 0.2% by mass in the total solid content. % Or more is further preferable, 5% by mass or less is preferable, 4% by mass or less is more preferable, 3% by mass or less is further preferable, 2% by mass or less is further preferable, and 1% by mass or less is particularly preferable.
  • the dispersion stability of the phthalocyanine compound (1) tends to be improved and the contrast tends to be improved, and when it is at least the above upper limit value, it tends to be easy to secure alkali developability. ..
  • the content ratio of the dispersant (C) in the colored resin composition is preferably 0.05 to 5% by mass, more preferably 0.05 to 4% by mass, and 0.1 to 3% by mass in the total solid content. Is even more preferable, 0.1 to 2% by mass is even more preferable, and 0.2 to 1% by mass is particularly preferable.
  • the content ratio of the dispersant (c1) in the colored resin composition of the present invention is not particularly limited, but is preferably 0.1 part by mass or more, more preferably 0.5 part by mass or more with respect to 100 parts by mass of the (A) colorant.
  • 1 part by mass or more is further preferable, 1.5 parts by mass or more is further preferable, 4 parts by mass or less is preferable, 3 parts by mass or less is more preferable, and 2.5 parts by mass or less is further preferable.
  • the dispersion stability of the phthalocyanine compound (1) tends to be improved and the contrast tends to be easily improved
  • it tends to be easy to secure the pattern characteristics.
  • the content ratio of the dispersant (c1) in the colored resin composition is preferably 0.1 to 4 parts by mass, more preferably 0.5 to 4 parts by mass with respect to 100 parts by mass of the (A) colorant. Up to 3 parts by mass is more preferable, and 1.5 to 2.5 parts by mass is even more preferable.
  • the content ratio of the dispersant (c1) in the colored resin composition of the present invention is not particularly limited, but is preferably 0.1% by mass or more, more preferably 0.2% by mass or more, and 0.3% by mass in the total solid content. % Or more is more preferable, 2% by mass or less is preferable, 1.5% by mass or less is more preferable, and 1% by mass or less is further preferable.
  • the content ratio of the dispersant (c1) in the colored resin composition is preferably 0.1 to 2% by mass, more preferably 0.2 to 1.5% by mass, and 0.3 to 1 in the total solid content. % By mass is more preferred.
  • the colored resin composition of the present invention contains (D) an alkali-soluble resin.
  • (D) By containing the alkali-soluble resin it is possible to achieve both film curability by photopolymerization and solubility by a developing solution.
  • the alkali-soluble resin include Japanese Patent Laid-Open No. 7-207211, Japanese Patent Application Laid-Open No. 8-259876, Japanese Patent Application Laid-Open No. 10-300922, and Japanese Patent Application Laid-Open No. 11-140144. , Japanese Patent Application Laid-Open No. 11-174224, Japanese Patent Application Laid-Open No. 2000-563118, and Japanese Patent Application Laid-Open No. 2003-233179 can be used.
  • (D-1) With respect to a copolymer of an epoxy group-containing (meth) acrylate and another radically polymerizable monomer, unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer. It may be referred to as an alkali-soluble resin (hereinafter referred to as "resin (D-1)") obtained by adding a polybasic acid anhydride to at least a part of the added resin or the hydroxyl group generated by the addition reaction.
  • resin (D-1) alkali-soluble resin obtained by adding a polybasic acid anhydride to at least a part of the added resin or the hydroxyl group generated by the addition reaction.
  • (D-2) A linear alkali-soluble resin containing a carboxy group in the main chain (hereinafter, may be referred to as “resin (D-2)").
  • (D-3) A resin obtained by adding an epoxy group-containing unsaturated compound to the carboxy group portion of the resin (D-2) (hereinafter, may be referred to as “resin (D-3)”).
  • (D-4) (Meta) acrylic resin (hereinafter, may be referred to as “resin (D-4)") (D-5) Epoxy (meth) acrylate resin having a carboxy group (hereinafter, may be referred to as "resin (D-5)”).
  • resin (D-1) is particularly preferable.
  • the resins (D-2) to (D-5) may be dissolved by an alkaline developer and have solubility to the extent that the desired developing treatment can be carried out, and each of them may be Japanese Patent Application Laid-Open No. 2009-025813.
  • the resin described as the same item in Japanese Patent Publication No. can be preferably adopted.
  • (D-1) An unsaturated monobasic acid is added to at least a part of the epoxy group of the copolymer of the epoxy group-containing (meth) acrylate and another radically polymerizable monomer.
  • the alkali-soluble resin resin (D-1) obtained by adding a polybasic acid anhydride to at least a part of the hydroxyl group generated by the addition reaction the resin is "containing an epoxy group".
  • the (meth) acrylate is unsaturated with 10 to 100 mol% of the epoxy group of the copolymer with respect to the polymer of 5 to 90 mol% of the acrylate and 10 to 95 mol% of the other radically polymerizable monomer. Examples thereof include a resin obtained by adding a basic acid, or an alkali-soluble resin obtained by adding a polybasic acid anhydride to 10 to 100 mol% of a hydroxyl group generated by the addition reaction.
  • Examples of the epoxy group-containing (meth) acrylate include glycidyl (meth) acrylate, 3,4-epoxybutyl (meth) acrylate, (3,4-epoxycyclohexyl) methyl (meth) acrylate, and 4-hydroxybutyl (meth).
  • Acrylate glycidyl ether can be exemplified. Of these, glycidyl (meth) acrylate is preferable.
  • One of these epoxy group-containing (meth) acrylates may be used alone, or two or more thereof may be used in combination.
  • a mono (meth) acrylate having a structure represented by the following general formula (V) is preferable.
  • R 91 to R 98 each independently represent a hydrogen atom or an alkyl group having 1 to 3 carbon atoms.
  • R 96 and R 98 , or R 95 and R 97 may be connected to each other to form a ring.
  • the ring formed by connecting R 96 and R 98 or R 95 and R 97 is preferably an aliphatic ring, which may be saturated or unsaturated, and may be carbon. The number is preferably 5-6.
  • the structure represented by the formula (V) the structure represented by the following general formula (Va), (Vb), or (Vc) is preferable.
  • the mono (meth) acrylate having the structure represented by the formula (V) one type may be used alone, or two or more types may be used in combination.
  • the mono (meth) acrylate having the structure represented by the formula (V) various known mono (meth) acrylates can be used as long as they have the structure represented by the formula (V), and in particular, the following general formula ( The mono (meth) acrylate represented by VI) is preferable.
  • R 89 represents a hydrogen atom or a methyl group
  • R 90 represents a structure represented by the formula (V).
  • the formula (VI) When a repeating unit derived from a mono (meth) acrylate represented by the formula (VI) is contained in a copolymer of an epoxy group-containing (meth) acrylate and another radically polymerizable monomer, the formula (VI) is used.
  • the content ratio of the repeating unit derived from the represented mono (meth) acrylate is preferably 5 to 90 mol%, more preferably 10 to 70 mol%, among the repeating units derived from other radically polymerizable monomers. 15-50 mol% is particularly preferred.
  • the radically polymerizable monomer other than the mono (meth) acrylate represented by the formula (VI) is not particularly limited, but specifically, for example, styrene and ⁇ - and o- of styrene. , M-, p-alkyl, nitro, cyano, amide, ester derivatives and other vinyl aromatics; butadiene, 2,3-dimethylbutadiene, isoprene, chloroprene and other dienes; (meth) methyl acrylate, (meth) Ethyl acrylate, (meth) acrylic acid-n-propyl, (meth) acrylic acid-iso-propyl, (meth) acrylic acid-n-butyl, (meth) acrylic acid-sec-butyl, (meth) acrylic acid- tert-butyl, (meth) pentyl acrylate, (meth) neo-pentyl acrylate, (meth) isoamyl acryl
  • styrene, benzyl (meth) acrylate, and monomaleimide are preferable from the viewpoint of imparting excellent heat resistance and strength to the colored resin composition.
  • the copolymer of an epoxy group-containing (meth) acrylate and another radically polymerizable monomer contains any repeating unit derived from styrene, benzyl (meth) acrylate, or monomaleimide, the other radical polymerization.
  • the total content of the repeating unit derived from styrene, the repeating unit derived from benzyl (meth) acrylate, and the repeating unit derived from monomaleimide among the repeating units derived from the sex monomer is 1 to 70 mol%. It is preferable, 3 to 50 mol% is more preferable.
  • a known solution polymerization method can be applied to the copolymerization reaction between the epoxy group-containing (meth) acrylate and another radically polymerizable monomer.
  • the solvent to be used is not particularly limited as long as it is inert to radical polymerization, and a commonly used organic solvent can be used.
  • Examples of the solvent used in the solution polymerization method include ethylene glycol monoalkyl ether acetates such as ethyl acetate, isopropyl acetate, cellosolve acetate and butyl cellosolve acetate; and diethylene glycol mono such as diethylene glycol monomethyl ether acetate, carbitol acetate and butyl carbitol acetate.
  • Alkyl ether acetates Propropylene glycol monoalkyl ether acetates; Acetate esters such as dipropylene glycol monoalkyl ether acetates; Ethylene glycol dialkyl ethers; Diethylene glycol dialkyl ethers such as methylcarbitol, ethylcarbitol, butylcarbitol, etc.
  • Triethylene glycol dialkyl ethers Triethylene glycol dialkyl ethers; propylene glycol dialkyl ethers; dipropylene glycol dialkyl ethers; ethers such as 1,4-dioxane and tetrahydrofuran; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone; benzene and toluene , Xylene, octane, decane and other hydrocarbons; petroleum-based solvents such as petroleum ether, petroleum naphtha, hydrogenated petroleum naphtha, solvent naphtha; lactic acid esters such as methyl lactate, ethyl lactate, butyl lactate; dimethylformamide, N- Methylpyrrolidone may be mentioned.
  • ethers such as 1,4-dioxane and tetrahydrofuran
  • ketones such as acetone,
  • the amount of the solvent used in the solution polymerization method is usually 30 to 1000 parts by mass, preferably 50 to 800 parts by mass with respect to 100 parts by mass of the obtained copolymer. By keeping the amount of the solvent used within the above range, it tends to be easy to control the molecular weight of the copolymer.
  • the radical polymerization initiator used in the copolymerization reaction is not particularly limited as long as it can initiate radical polymerization, and a commonly used organic peroxide catalyst or azo compound catalyst can be used. ..
  • organic peroxide catalyst include catalysts classified into known ketone peroxides, peroxyketals, hydroperoxides, diallyl peroxides, diacyl peroxides, peroxyesters, and peroxydicarbonates.
  • radical polymerization initiator used in the copolymerization reaction examples include benzoyl peroxide, dicumyl peroxide, diisopropyl peroxide, di-t-butyl peroxide, t-butyl peroxybenzoate, and t-hexyl peroxybenzoate.
  • radical polymerization initiators having an appropriate half-life are used depending on the polymerization temperature.
  • the amount of the radical polymerization initiator used is usually 0.5 to 20 parts by mass, preferably 1 to 10 parts by mass with respect to 100 parts by mass of the total amount of the monomers used in the copolymerization reaction.
  • the copolymerization reaction may be carried out by dissolving the monomer used in the polymerization reaction and the radical polymerization initiator in a solvent and raising the temperature with stirring, or using a monomer to which the radical polymerization initiator is added. , The temperature may be dropped in the stirred solvent, or the monomer may be dropped in the temperature obtained by adding the radical polymerization initiator to the solvent.
  • the reaction conditions can be set according to the target molecular weight.
  • the copolymer of the epoxy group-containing (meth) acrylate and another radically polymerizable monomer includes 5 to 90 mol% of repeating units derived from the epoxy group-containing (meth) acrylate and other radical polymerization. It is preferably composed of 10 to 95 mol% of repeating units derived from sex monomers; 20 to 80 mol% of repeating units derived from epoxy group-containing (meth) acrylates and other radically polymerizable monomers. More preferably, it consists of 80-20 mol% repeating units; 30-70 mol% repeating units derived from epoxy group-containing (meth) acrylates and 70-30 mol repeating units derived from other radically polymerizable monomers. The one consisting of% is particularly preferable.
  • the content ratio of the repeating unit derived from the epoxy group-containing (meth) acrylate By setting the content ratio of the repeating unit derived from the epoxy group-containing (meth) acrylate to the above lower limit value or more, the amount of unsaturated monobasic acid or polybasic acid anhydride described later tends to be sufficient. By setting the content ratio of the repeating unit derived from the other radically polymerizable monomer to the above lower limit value or more, the heat resistance and the strength tend to be sufficient.
  • an unsaturated monobasic acid (polymerizable component) and a polybasic acid anhydride (alkali-soluble) are added to the epoxy group of the copolymer of the epoxy resin-containing (meth) acrylate and another radically polymerizable monomer. Ingredient) and react.
  • a known unsaturated monobasic acid can be used, and examples thereof include unsaturated carboxylic acids having an ethylenically unsaturated double bond.
  • Examples of the unsaturated monobasic acid to be added to the epoxy group include (meth) acrylic acid; crotonic acid; o-, m-, and p-vinylbenzoic acid; the ⁇ -position is a haloalkyl group, an alkoxyl group, a halogen atom, and a nitro.
  • Examples thereof include monocarboxylic acids such as (meth) acrylic acid substituted with a group or a cyano group. Of these, (meth) acrylic acid is preferable.
  • One of these unsaturated monobasic acids may be used alone, or two or more thereof may be used in combination.
  • the resin (D-1) By adding an unsaturated monobasic acid to the epoxy group, the resin (D-1) can be imparted with polymerizable properties.
  • the unsaturated monobasic acid is added to usually 10 to 100 mol%, preferably 30 to 100 mol%, more preferably 50 to 100 mol% of the epoxy group contained in the copolymer. By setting the value to the lower limit or more, the stability of the colored resin composition with time tends to be good.
  • a method for adding an unsaturated monobasic acid to the epoxy group of the copolymer a known method can be adopted.
  • polybasic acid anhydride added to the hydroxyl group generated when the unsaturated monobasic acid is added to the epoxy group of the copolymer
  • a known polybasic acid anhydride can be used.
  • the polybasic acid anhydride include dibasic acid anhydrides such as maleic anhydride, succinic anhydride, itaconic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, phthalic anhydride, and chlorendic anhydride; Trimerit anhydride.
  • Examples thereof include anhydrates of three or more bases such as an acid, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, and biphenyltetracarboxylic acid anhydride. Of these, tetrahydrophthalic anhydride and succinic anhydride are preferable.
  • One of these polybasic acid anhydrides may be used alone, or two or more thereof may be used in combination.
  • Alkali solubility can be imparted to the resin (D-1) by adding the polybasic acid anhydride to the hydroxyl group generated when the unsaturated monobasic acid is added to the epoxy group of the copolymer.
  • the polybasic acid anhydride is usually 10 to 100 mol%, preferably 20 to 90 mol%, more preferably 30 to 80 mol% of the hydroxyl group generated by adding an unsaturated monobasic acid to the epoxy group of the copolymer. Add to%. When it is set to the upper limit value or less, the residual film ratio at the time of development tends to be good, and when it is set to the lower limit value or more, the solubility tends to be sufficient.
  • a method for adding a polybasic acid anhydride to a hydroxyl group generated by adding an unsaturated monobasic acid to the epoxy group of the copolymer a known method can be adopted.
  • a glycidyl (meth) acrylate or a glycidyl ether compound having a polymerizable unsaturated group may be added to a part of the generated carboxy group.
  • a glycidyl ether compound having no polymerizable unsaturated group may be added to a part of the generated carboxy group. Both of these may be added.
  • Examples of the glycidyl ether compound having no polymerizable unsaturated group include glycidyl ether compounds having a phenyl group and an alkyl group.
  • the structure of the resin (D-1) is described in, for example, Japanese Patent Application Laid-Open No. 8-297366 and Japanese Patent Application Laid-Open No. 2001-89533.
  • the polystyrene-equivalent weight average molecular weight measured by GPC of the resin (D-1) is not particularly limited, but is preferably 3000 to 100,000, and particularly preferably 5000 to 50,000. When it is at least the above lower limit value, the heat resistance and film strength tend to be good, and when it is at least the above upper limit value, the solubility in a developing solution tends to be good.
  • the ratio (Mw / Mn) of the weight average molecular weight of the resin (D-1) to the number average molecular weight is preferably 2.0 to 5.0.
  • the (d1) acrylic copolymer resin having an ethylenically unsaturated group in the side chain is preferable.
  • the partial structure of the acrylic copolymer resin having an ethylenically unsaturated group in the side chain including the side chain having an ethylenically unsaturated group is not particularly limited, but the coating film curability and alkali development during ultraviolet exposure are not particularly limited. From the viewpoint of achieving both alkali solubility at the time, for example, it is preferable to have a partial structure represented by the following general formula (I).
  • R 1 and R 2 each independently represent a hydrogen atom or a methyl group. * Represents a bond.
  • the partial structure represented by the following general formula (I') is preferable from the viewpoint of sensitivity and alkali developability.
  • R 1 and R 2 each independently represent a hydrogen atom or a methyl group.
  • RX represents a hydrogen atom or a polybasic acid residue.
  • the polybasic acid residue means a monovalent group obtained by subtracting one OH group from the polybasic acid or its anhydride.
  • the polybasic acid include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methylhexahydrophthalic acid and endomethylene.
  • examples thereof include tetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid and biphenyltetracarboxylic acid.
  • maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid and biphenyltetracarboxylic acid are preferable, and tetrahydrophthalic acid and biphenyltetracarboxylic acid are preferable. Is more preferable.
  • These polybasic acids may be used alone or in combination of two or more.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure represented by the formula (I)
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) can be used.
  • the content ratio of the partial structure represented by the formula (I) contained is not particularly limited, but is preferably 10 mol% or more, more preferably 20 mol% or more, further preferably 30 mol% or more, still more preferably 40 mol% or more.
  • mol% or more is particularly preferable, 65 mol% or more is most preferable, 95 mol% or less is preferable, 90 mol% or less is more preferable, 85 mol% or less is further preferable, and 80 mol% or less is more preferable. More preferably, 75 mol% or less is particularly preferable, and 70 mol% or less is most preferable.
  • the coating film curability at the time of exposure to ultraviolet rays tends to be improved
  • it is at least the above upper limit value the alkali solubility at the time of alkaline development tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the content of the partial structure represented by the formula (I) contained in the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) is preferably 10 to 95 mol%, preferably 20 to 90 mol%. More preferably, 30 to 85 mol% is further preferable, 40 to 80 mol% is further preferable, 50 to 75 mol% is particularly preferable, and 65 to 70 mol% is most preferable.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain has a partial structure represented by the formula (I')
  • the acrylic copolymer resin having an ethylenically unsaturated group in the (d1) side chain is not particularly limited, but is preferably 10 mol% or more, more preferably 20 mol% or more, further preferably 30 mol% or more, and even more preferably 40 mol%.
  • the above is even more preferable, 50 mol% or more is particularly preferable, 65 mol% or more is most preferable, 95 mol% or less is preferable, 90 mol% or less is more preferable, 85 mol% or less is further preferable, and 80 mol% is more preferable.
  • the following is even more preferable, 75 mol% or less is particularly preferable, and 70 mol% or less is most preferable.
  • the content of the partial structure represented by the formula (I) contained in the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) is preferably 10 to 95 mol%, preferably 20 to 90 mol%. More preferably, 30 to 85 mol% is further preferable, 40 to 80 mol% is further preferable, 50 to 75 mol% is particularly preferable, and 65 to 70 mol% is most preferable.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain contains a partial structure represented by the formula (I), the other partial structure is not particularly limited, but alkali dissolution during alkaline development. From the viewpoint of sex, it is also preferable to have a partial structure represented by the following general formula (II), for example.
  • R 3 represents a hydrogen atom or a methyl group
  • R 4 is an alkyl group which may have a substituent, an aromatic ring group which may have a substituent, or a substituent.
  • R 4 represents an alkyl group which may have a substituent, an aromatic ring group which may have a substituent, or an alkenyl group which may have a substituent.
  • alkyl group in R 4 include linear, branched or cyclic alkyl groups.
  • the number of carbon atoms is preferably 1 or more, more preferably 3 or more, further preferably 5 or more, particularly preferably 8 or more, still preferably 20 or less, more preferably 18 or less, further preferably 16 or less, still more preferably 14 or less. Even more preferably, 12 or less is particularly preferable.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 18, further preferably 3 to 16, still more preferably 5 to 14, and particularly preferably 8 to 12.
  • Examples of the alkyl group include a methyl group, an ethyl group, a cyclohexyl group, a dicyclopentanyl group and a dodecanyl group. From the viewpoint of developability, a dicyclopentanyl group and a dodecanyl group are preferable, and a dicyclopentanyl group is more preferable.
  • Examples of the substituent that the alkyl group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. , Acryloyl group, and methacryloyl group. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • Examples of the aromatic ring group in R 4 include a monovalent aromatic hydrocarbon ring group and a monovalent aromatic heterocyclic group.
  • the number of carbon atoms is preferably 6 or more, preferably 24 or less, more preferably 22 or less, further preferably 20 or less, and particularly preferably 18 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the aromatic ring group is preferably 6 to 24, more preferably 6 to 22, further preferably 6 to 20, and particularly preferably 6 to 18.
  • the aromatic hydrocarbon ring in the aromatic hydrocarbon ring group may be a monocyclic ring or a fused ring, and may be, for example, a benzene ring, a naphthalene ring, an anthracene ring, a phenanthrene ring, a perylene ring, a tetracene ring, or pyrene.
  • the aromatic heterocycle in the aromatic heterocyclic group may be a monocyclic ring or a fused ring, and may be, for example, a furan ring, a benzofuran ring, a thiophene ring, a benzothiophene ring, a pyrrole ring, a pyrazole ring, or an imidazole ring.
  • Oxadiazole ring indole ring, carbazole ring, pyrrolobymidazole ring, pyrrolopyrazole ring, pyrrolopyrrole ring, thienopyrazole ring, thienothiophene ring, flopyrol ring, floran ring, thienoflan ring, benzoisoxazole ring, benzoisothiazole ring, Examples thereof include a benzimidazole ring, a pyridine ring, a pyrazine ring, a pyridazine ring, a pyrimidine ring, a triazine ring, a quinoline ring, an isoquinoline ring, a synolin ring, a quinoxalin ring, a phenanthridine ring, a perimidine ring, a quinazoline ring, a quinazolinone ring, and an azulene ring
  • a benzene ring group and a naphthalene ring group are preferable, and a benzene ring group is more preferable.
  • the substituent that the aromatic ring group may have include a methyl group, an ethyl group, a propyl group, a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group and an epoxy group.
  • Oligoethylene glycol group, phenyl group, carboxy group and the like From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • Examples of the alkenyl group in R 4 include a linear, branched or cyclic alkenyl group.
  • the number of carbon atoms is preferably 2 or more, preferably 22 or less, more preferably 20 or less, further preferably 18 or less, further preferably 16 or less, and particularly preferably 14 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the alkenyl group preferably has 2 to 22 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 18 carbon atoms, still more preferably 2 to 16 carbon atoms, and particularly preferably 2 to 14 carbon atoms.
  • alkenyl group examples include a vinyl group, an allyl group, a 2-propen-2-yl group, a 2-butene-1-yl group, a 3-butene-1-yl group, a 2-pentene-1-yl group, and 3 -Pentene-2-yl group, hexenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl can be mentioned. From the viewpoint of developability, a vinyl group and an allyl group are preferable, and a vinyl group is more preferable.
  • Examples of the substituent that the alkenyl group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. Can be mentioned. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • R 4 represents an alkyl group which may have a substituent, an aromatic ring group which may have a substituent, or an alkenyl group which may have a substituent, and has a developability and a film strength. From the viewpoint, an alkyl group or an alkenyl group is preferable, and an alkyl group is more preferable.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure represented by the formula (II)
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure.
  • the content ratio of the partial structure represented by the formula (II) is not particularly limited, but 1 mol% or more is preferable, 5 mol% or more is more preferable, 10 mol% or more is further preferable, and 20 mol% or more is particularly preferable. Further, 70 mol% or less is preferable, 60 mol% or less is more preferable, 50 mol% or less is further preferable, and 40 mol% or less is particularly preferable.
  • the alkali solubility tends to be improved
  • the storage stability of the colored resin composition tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the partial structure represented by the formula (II) in the acrylic copolymer resin having an ethylenically unsaturated group in the (d1) side chain is preferably 1 to 70 mol%, more preferably 5 to 60 mol%. 10 to 50 mol% is more preferable, and 20 to 40 mol% is particularly preferable.
  • the affinity between the phthalocyanine compound (1) and the acrylic copolymer resin (d1) is to be improved as the other partial structure contained.
  • the partial structure represented by the following general formula (III) is contained.
  • R 5 represents a hydrogen atom or a methyl group
  • R 6 has an alkyl group which may have a substituent, an alkenyl group which may have a substituent, and a substituent. It represents an alkynyl group, a hydroxy group, a carboxy group, a halogen atom, an alkoxy group which may have a substituent, a thiol group, or an alkyl sulfide group which may have a substituent.
  • t represents an integer from 0 to 5.
  • R 6 has an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, a hydroxy group, a carboxy group, and the like. Represents a halogen atom, an alkoxy group which may have a substituent, a thiol group, or an alkyl sulfide group which may have a substituent.
  • Examples of the alkyl group in R 6 include linear, branched or cyclic alkyl groups.
  • the number of carbon atoms is preferably 1 or more, more preferably 3 or more, further preferably 5 or more, still more preferably 20 or less, further preferably 18 or less, further preferably 16 or less, further preferably 14 or less, and even more preferably 12 or less. Is particularly preferable.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 18, further preferably 3 to 16, still more preferably 3 to 14, and particularly preferably 5 to 12.
  • Examples of the alkyl group include a methyl group, an ethyl group, a cyclohexyl group, a dicyclopentanyl group and a dodecanyl group. From the viewpoint of heat resistance, a dicyclopentanyl group and a dodecanyl group are preferable, and a dicyclopentanyl group is more preferable.
  • Examples of the substituent that the alkyl group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. , Acryloyl group, and methacryloyl group. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • Examples of the alkenyl group in R 6 include a linear, branched or cyclic alkenyl group.
  • the number of carbon atoms is preferably 2 or more, preferably 22 or less, more preferably 20 or less, further preferably 18 or less, further preferably 16 or less, and particularly preferably 14 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the alkenyl group preferably has 2 to 22 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 18 carbon atoms, still more preferably 2 to 16 carbon atoms, and particularly preferably 2 to 14 carbon atoms.
  • alkenyl group examples include a vinyl group, an allyl group, a 2-propen-2-yl group, a 2-butene-1-yl group, a 3-butene-1-yl group, a 2-pentene-1-yl group, and 3 -Pentene-2-yl group, hexenyl group, cyclobutenyl group, cyclopentenyl group, cyclohexenyl can be mentioned. From the viewpoint of exposure sensitivity during ultraviolet exposure, a vinyl group and an allyl group are preferable, and a vinyl group is more preferable.
  • Examples of the substituent that the alkenyl group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. Can be mentioned. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • Examples of the alkynyl group in R 6 include a linear, branched or cyclic alkynyl group.
  • the number of carbon atoms is preferably 2 or more, preferably 22 or less, more preferably 20 or less, further preferably 18 or less, further preferably 16 or less, and particularly preferably 14 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the alkynyl group preferably has 2 to 22 carbon atoms, more preferably 2 to 20 carbon atoms, further preferably 2 to 18 carbon atoms, still more preferably 2 to 16 carbon atoms, and particularly preferably 2 to 14 carbon atoms.
  • alkynyl group examples include 1-propyne-3-yl group, 1-butyne-4-yl group, 1-pentyne-5-yl group, 2-methyl-3-butin-2-yl group, 1,4. Examples thereof include -pentadiyne-3-yl group, 1,3-pentadiyne-5-yl group and 1-hexin-6-yl group.
  • Examples of the substituent that the alkynyl group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. Can be mentioned. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • halogen atom in R 6 examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • D1 A fluorine atom is preferable from the viewpoint of storage stability of the acrylic copolymer resin.
  • Examples of the alkoxy group in R 6 include a linear, branched or cyclic alkoxy group.
  • the number of carbon atoms is preferably 1 or more, preferably 20 or less, more preferably 18 or less, further preferably 16 or less, further preferably 14 or less, and particularly preferably 12 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved. be.
  • the above upper and lower limits can be combined arbitrarily.
  • the alkoxy group preferably has 1 to 20 carbon atoms, more preferably 1 to 18 carbon atoms, further preferably 1 to 16 carbon atoms, still more preferably 1 to 14 carbon atoms, and particularly preferably 1 to 12 carbon atoms.
  • alkoxy group examples include a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group, a butoxy group, and an isobutoxy group.
  • Examples of the substituent that the alkoxy group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group, a phenyl group and a carboxy group. , Acryloyl group, and methacryloyl group. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • Examples of the alkyl sulfide group in R 6 include linear, branched or cyclic alkyl sulfide groups.
  • the number of carbon atoms is preferably 1 or more, preferably 20 or less, more preferably 18 or less, further preferably 16 or less, further preferably 14 or less, and particularly preferably 12 or less.
  • lipophilicity tends to be improved and solubility in a solvent tends to be improved
  • hydrophilicity is improved and alkali solubility tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the alkyl sulfide group is preferably 1 to 20, more preferably 1 to 18, further preferably 1 to 16, further preferably 1 to 14, and particularly preferably 1 to 12.
  • alkyl sulfide group examples include a methyl sulfide group, an ethyl sulfide group, a propyl sulfide group, and a butyl sulfide group. From the viewpoint of developability, a methyl sulfide group and an ethyl sulfide group are preferable.
  • Examples of the substituent that the alkyl group in the alkyl sulfide group may have include a methoxy group, an ethoxy group, a chloro group, a bromo group, a fluoro group, a hydroxy group, an amino group, an epoxy group, an oligoethylene glycol group and a phenyl group.
  • Examples thereof include a group, a carboxy group, an acryloyl group and a methacryloyl group. From the viewpoint of developability, a hydroxy group and an oligoethylene glycol group are preferable.
  • R 6 has an alkyl group which may have a substituent, an alkenyl group which may have a substituent, an alkynyl group which may have a substituent, a hydroxy group, a carboxy group, a halogen atom and an alkoxy group.
  • a hydroxyalkyl group, a thiol group, or an alkyl sulfide group which may have a substituent and from the viewpoint of developability, a hydroxy group or a carboxy group is preferable, and a carboxy group is more preferable.
  • t represents an integer from 0 to 5. From the viewpoint of ease of manufacture, t is preferably 0.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure represented by the formula (III)
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure.
  • the content ratio of the partial structure represented by the formula (III) is not particularly limited, but 1 mol% or more is preferable, 2 mol% or more is more preferable, 5 mol% or more is further preferable, and 8 mol% or more is particularly preferable. Further, 50 mol% or less is preferable, 40 mol% or less is more preferable, 30 mol% or less is further preferable, and 20 mol% or less is particularly preferable.
  • the affinity between the phthalocyanine compound (1) and (d1) acrylic copolymer resin tends to be improved, and the alkali solubility tends to be improved.
  • the content ratio of the structure increases, and the alkali solubility tends to improve.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the partial structure represented by the formula (III) in the acrylic copolymer resin having an ethylenically unsaturated group in the (d1) side chain is preferably 1 to 50 mol%, more preferably 2 to 40 mol%. 5 to 30 mol% is more preferable, and 8 to 20 mol% is particularly preferable.
  • R 7 represents a hydrogen atom or a methyl group.
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure represented by the formula (IV)
  • the acrylic copolymer resin having an ethylenically unsaturated group in the side chain (d1) has a partial structure.
  • the content ratio of the partial structure represented by the formula (II) is not particularly limited, but is preferably 5 mol% or more, more preferably 10 mol% or more, further preferably 20 mol% or more, and preferably 80 mol% or less. 70% mol or less is more preferable, and 60% mol or less is further preferable.
  • the alkali solubility tends to be improved
  • the storage stability of the colored resin composition tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the partial structure represented by the formula (II) in the acrylic copolymer resin having an ethylenically unsaturated group in the (d1) side chain is preferably 5 to 80 mol%, more preferably 10 to 70 mol%. 20-60% mol is more preferred.
  • the acid value of the alkali-soluble resin (D) is not particularly limited, but is preferably 10 mgKOH / g or more, more preferably 30 mgKOH / g or more, further preferably 40 mgKOH / g or more, still more preferably 50 mgKOH / g or more, and 60 mgKOH / g.
  • the above is particularly preferable, and 300 mgKOH / g or less is preferable, 250 mgKOH / g or less is more preferable, 200 mgKOH / g or less is further preferable, and 150 mgKOH / g or less is further preferable.
  • the acid value of the alkali-soluble resin (D) is preferably 10 to 300 mgKOH / g, more preferably 30 to 300 mgKOH / g, further preferably 40 to 250 mgKOH / g, even more preferably 50 to 200 mgKOH / g, and 60 to 60 to 200 mgKOH / g. 150 mgKOH / g is particularly preferable.
  • the weight average molecular weight of the alkali-soluble resin (D) is not particularly limited, but is usually 1000 or more, preferably 2000 or more, more preferably 4000 or more, still more preferably 6000 or more, still more preferably 7000 or more, and particularly preferably 8000 or more. Also, it is usually 30,000 or less, preferably 20,000 or less, more preferably 15,000 or less, still more preferably 10,000 or less. When it is at least the above lower limit value, heat resistance and coating film curability tend to be improved, and when it is at least the above upper limit value, alkali solubility tends to be improved. The above upper and lower limits can be combined arbitrarily.
  • the weight average molecular weight of the alkali-soluble resin (D) is preferably 1000 to 30000, more preferably 2000 to 30000, still more preferably 4000 to 20000, further preferably 6000 to 20000, particularly preferably 7000 to 15000, and 8000 to 8000. 10000 is particularly preferable.
  • the content ratio of the (D) alkali-soluble resin in the colored resin composition of the present invention is not particularly limited, but is usually 1% by mass or more, preferably 5% by mass or more, more preferably 5% by mass or more in the total solid content of the colored resin composition. It is 10% by mass or more, more preferably 20% by mass or more, still more preferably 25% by mass or more, particularly preferably 30% by mass or more, and usually 80% by mass or less, preferably 60% by mass or less, more preferably. It is 50% by mass or less, more preferably 40% by mass or less.
  • the content ratio of the (D) alkali-soluble resin in the colored resin composition is preferably 1 to 80% by mass, more preferably 5 to 80% by mass, and 10 to 60% by mass in the total solid content of the colored resin composition. Is even more preferable, 20 to 60% by mass is even more preferable, 25 to 50% by mass is particularly preferable, and 30 to 40% by mass is particularly preferable.
  • the colored resin composition of the present invention contains (E) a photopolymerization initiator.
  • E) a photopolymerization initiator By containing a photopolymerization initiator, film curability by photopolymerization can be obtained.
  • the photopolymerization initiator can also be used as a mixture (photopolymerization initiator) with an accelerator (chain transfer agent) and an additive such as a sensitizing dye added as needed.
  • the photopolymerization initiation system is a component having a function of directly absorbing light or being photosensitized to cause a decomposition reaction or a hydrogen abstraction reaction to generate a polymerization active radical.
  • Examples of the photopolymerization initiator include metallocene compounds containing titanosen compounds described in Japanese Patent Laid-Open Nos. 59-152396 and Japanese Patent Laid-Open No. 61-151197, and Japanese Patent Application Laid-Open No. 10-39503.
  • N-aryl- ⁇ -amino acids such as hexaarylbiimidazole derivatives, halomethyl-s-triazine derivatives, N-phenylglycine, N-aryl- ⁇ -amino acid salts, N-aryl- ⁇ -amino acid esters, etc.
  • Examples thereof include a radical activator of the above, an ⁇ -aminoalkylphenone-based compound, and an oxime ester-based initiator described in Japanese Patent Application Laid-Open No. 2000-80068.
  • photopolymerization initiator that can be used in the present invention are listed below.
  • 2- (4-Methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine 2- (4-methoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4) Halomethylated triazine derivatives such as -ethoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-ethoxycarbonylnaphthyl) -4,6-bis (trichloromethyl) -s-triazine;
  • Benzophenone derivatives such as benzophenone, Michler's ketone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone; 2,2-Dimethoxy-2-phenylacetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexylphenyl ketone, ⁇ -hydroxy-2-methylphenylpropanol, 1-hydroxy-1-methylethyl- (p) -Isopropylphenyl) Ketone, 1-Hydroxy-1- (p-dodecylphenyl) Ketone, 2-Methyl-1- [4- (Methylthio) Phenyl] -2-morpholinopropane-1-one, 1,1,1 -Acetophenone derivatives such as trichloromethyl- (p-butylphenyl) ketone; Thioxanthone
  • Ethyl benzoate derivatives such as ethyl p-dimethylaminobenzoate and ethyl P-diethylaminobenzoate; Acridine derivatives such as 9-phenylacridine and 9- (p-methoxyphenyl) acridine; Phenazine derivatives such as 9,10-dimethylbenzphenazine; Anthrone derivatives such as Benz anthrone; Dicyclopentadienyl-Ti-dichloride, dicyclopentagenyl-Ti-bis-phenyl, dicyclopentagenyl-Ti-bis-2,3,4,5,6-pentafluorophenyl-1-yl, Dicyclopentagenyl-Ti-bis-2,3,5,6-tetrafluorophenyl-1-yl, dicyclopentagenyl-Ti-bis-2,4,6-trifluoropheni-1-yl, Dicyclopentagenyl-Ti-2,6-diprul
  • an oxime ester-based compound (oxime ester-based photopolymerization initiator) is preferable.
  • Oxime ester compounds have a structure that absorbs ultraviolet rays, a structure that transmits light energy, and a structure that generates radicals in their structure, so that they are highly sensitive in a small amount and stable against thermal reactions. Therefore, it is possible to design a highly sensitive colored resin composition with a small amount.
  • an oxime ester-based compound having a carbazole ring, which may have a substituent is preferable from the viewpoint of light absorption of the exposure light source for i-ray (365 nm).
  • Examples of the oxime ester compound include compounds represented by the following general formula (I-1).
  • R 21a represents a hydrogen atom, an alkyl group which may have a substituent, or an aromatic ring group which may have a substituent.
  • R 21b represents any substituent, including aromatic or heteroaromatic rings.
  • R 22a represents an alkanoyl group which may have a substituent or an allyloyl group which may have a substituent.
  • the number of carbon atoms of the alkyl group in R 21a is not particularly limited, but is usually 1 or more, preferably 2 or more, and usually 20 or less, preferably 15 or less, more preferably, from the viewpoint of solubility in a solvent and sensitivity to exposure. It is 10 or less, more preferably 5 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, further preferably 1 to 5, and particularly preferably 2 to 5.
  • the alkyl group include a methyl group, an ethyl group, a propyl group, a cyclopentylethyl group and a propyl group.
  • alkyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, and 4- (2-methoxy-1-methyl) ethoxy-2-.
  • substituents that the alkyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, and 4- (2-methoxy-1-methyl) ethoxy-2-.
  • substituent that the alkyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, and 4- (2-methoxy-1-methyl) ethoxy-2-.
  • substituents include a methylphenyl group and an N-acetyl-N-acetoxyamino group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.
  • Examples of the aromatic ring group in R 21a include an aromatic hydrocarbon ring group and an aromatic heterocyclic group.
  • the number of carbon atoms of the aromatic ring group is not particularly limited, but is preferably 5 or more from the viewpoint of solubility in the colored resin composition. Further, from the viewpoint of developability, it is preferably 30 or less, more preferably 20 or less, further preferably 12 or less, and particularly preferably 8 or less. The above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the aromatic ring group is preferably 5 to 30, more preferably 5 to 20, further preferably 5 to 12, and particularly preferably 5 to 8.
  • Examples of the aromatic ring group include a phenyl group, a naphthyl group, a pyridyl group, a frill group and a fluorenyl group. From the viewpoint of developability, a phenyl group, a naphthyl group and a fluorenyl group are preferable, and a phenyl group and a fluorenyl group are more preferable.
  • Examples of the substituent that the aromatic ring group may have include a hydroxyl group, an alkyl group that may have a substituent, an alkoxy group that may have a substituent, a carboxy group, and a halogen atom. Examples thereof include an amino group, an amide group and an alkyl group.
  • a hydroxyl group and a carboxy group are preferable, and a carboxy group is more preferable.
  • the substituent in the alkyl group which may have a substituent and the alkoxy group which may have a substituent include a hydroxyl group, an alkoxy group, a halogen atom and a nitro group.
  • R 21a an alkyl group which may have a substituent is preferable, an unsubstituted alkyl group is more preferable, and a methyl group is further preferable.
  • R 21b is any substituent, including aromatic or heteroaromatic rings.
  • a carbazolyl group which may have a substituent
  • a thioxanthonyl group which may have a substituent
  • a diphenylsulfide group which may have a substituent
  • a fluorenyl group which may have a substituent and a group in which these groups and a carbonyl group are linked are preferable.
  • a carbazolyl group which may have a substituent or a group in which a carbazolyl group and a carbonyl group which may have a substituent are linked is preferable.
  • Examples of the substituent that the carbazolyl group may have include an alkyl group having 1 to 10 carbon atoms such as a methyl group and an ethyl group; an alkoxy group having 1 to 10 carbon atoms such as a methoxy group and an ethoxy group; F, Halogen atoms such as Cl, Br, I; acyl group with 1 to 10 carbon atoms; alkyl ester group with 1 to 10 carbon atoms; alkoxycarbonyl group with 1 to 10 carbon atoms; alkyl halide group with 1 to 10 carbon atoms; An aromatic ring group having 4 to 10 carbon atoms; an amino group; an aminoalkyl group having 1 to 10 carbon atoms; a hydroxyl group; a nitro group; a CN group; an allylloyl group which may have a substituent; Heteroaryloyl groups may be; examples include tenoyl groups which may have substituents.
  • the carbon number of the alkanoyl group in R 22a is not particularly limited, but from the viewpoint of solubility in a solvent and sensitivity, it is usually 2 or more, preferably 3 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less. , More preferably 5 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the alkanoyl group preferably has 2 to 20 carbon atoms, more preferably 2 to 15 carbon atoms, still more preferably 2 to 10 carbon atoms, still more preferably 2 to 5 carbon atoms, and particularly preferably 3 to 5 carbon atoms.
  • alkanoyl group examples include an acetyl group, an ethyloyl group, a propanoyl group, and a butanoyl group.
  • substituent that the alkanoyl group may have include an aromatic ring group, a hydroxyl group, a carboxy group, a halogen atom, an amino group and an amide group, which are unsubstituted from the viewpoint of ease of synthesis. Is preferable.
  • the carbon number of the allylloyl group in R 22a is not particularly limited, but from the viewpoint of solubility in a solvent and sensitivity, it is usually 7 or more, preferably 8 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less. Is. The above upper and lower limits can be combined arbitrarily.
  • the allylloyl group preferably has 7 to 20 carbon atoms, more preferably 7 to 15, still more preferably 7 to 10, and particularly preferably 8 to 10.
  • the allylloyl group include a benzoyl group and a naphthoyl group.
  • Examples of the substituent that the allylloyl group may have include a hydroxyl group, a carboxy group, a halogen atom, an amino group, an amide group, and an alkyl group, which may be unsubstituted from the viewpoint of easiness of synthesis. preferable.
  • Examples of the compound represented by the formula (I-1) include compounds represented by the following general formula (I-2) or (I-3) from the viewpoint of light absorption of the exposure light source for i-line (365 nm). Be done.
  • R 21a and R 22a are synonymous with formula (I-1).
  • R 23a represents an alkyl group which may have a substituent.
  • R 24a represents an alkyl group which may have a substituent, an allylloyl group which may have a substituent, a heteroallyloyl group which may have a substituent, or a nitro group.
  • the benzene ring constituting the carbazole ring may be further condensed by an aromatic ring to form a polycyclic aromatic ring.
  • the number of carbon atoms of the alkyl group in R 23a is not particularly limited, but from the viewpoint of solubility in a solvent, it is usually 1 or more, preferably 2 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less, and further. It is preferably 5 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, further preferably 1 to 5, and particularly preferably 2 to 5.
  • the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and a cyclohexyl group.
  • Examples of the substituent that the alkyl group may have include a carbonyl group, a carboxy group, a hydroxy group, a phenyl group, a benzyl group, a cyclohexyl group and a nitro group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.
  • R 23a is more preferably an ethyl group from the viewpoint of solubility in a solvent and easiness of synthesis.
  • the number of carbon atoms of the alkyl group in R 24a is not particularly limited, but from the viewpoint of solubility in a solvent, it is usually 1 or more, preferably 2 or more, and usually 20 or less, preferably 15 or less, more preferably 10 or less, and further. It is preferably 5 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of carbon atoms of the alkyl group is preferably 1 to 20, more preferably 1 to 15, further preferably 1 to 10, further preferably 1 to 5, and particularly preferably 2 to 5.
  • the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group and a cyclohexyl group.
  • alkyl group may have include a carbonyl group, a carboxy group, a hydroxy group, a phenyl group, a benzyl group, a cyclohexyl group and a nitro group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.
  • the carbon number of the allylloyl group in R 24a is not particularly limited, but from the viewpoint of solubility in a solvent, it is usually 7 or more, preferably 8 or more, more preferably 9 or more, and usually 20 or less, preferably 15 or less. It is preferably 10 or less, more preferably 9 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the allylloyl group preferably has 7 to 20 carbon atoms, more preferably 8 to 15, still more preferably 9 to 10, and particularly preferably 9.
  • the allylloyl group include a benzoyl group and a naphthoyl group.
  • Examples of the substituent that the allylloyl group may have include a carbonyl group, a carboxy group, a hydroxy group, a phenyl group, a benzyl group, a cyclohexyl group, and a nitro group. From the viewpoint of ease of synthesis, an ethyl group is preferable.
  • the number of carbon atoms of the heteroallyloyl group in R 24a is not particularly limited, but from the viewpoint of solubility in a solvent, it is usually 7 or more, preferably 8 or more, more preferably 9 or more, and usually 20 or less, preferably 15 or less. , More preferably 10 or less, still more preferably 9 or less.
  • the above upper and lower limits can be combined arbitrarily.
  • the heteroallyloyl group preferably has 7 to 20 carbon atoms, more preferably 8 to 15, still more preferably 9 to 10, and particularly preferably 9.
  • heteroaryl group examples include a fluorobenzoyl group, a chlorobenzoyl group, a bromobenzoyl group, a fluoronaphthoyl group, a chloronaphthoyl group, and a bromonaphthoyl group.
  • substituent that the heteroarylloyl group may have include a carbonyl group, a carboxy group, a hydroxy group, a phenyl group, a benzyl group, a cyclohexyl group and a nitro group. From the viewpoint of ease of synthesis, it is preferably unsubstituted.
  • R 24a an allylloyl group which may have a substituent is preferable, and a benzoyl group is more preferable, from the viewpoint of sensitivity.
  • the benzene ring constituting the carbazole ring may be further condensed by an aromatic ring to form a polycyclic aromatic ring.
  • oxime ester compounds include, for example, OXE-02 and OXE-03 manufactured by BASF, TR-PBG-304 and TR-PBG-314 manufactured by Changzhou Strong Electronics New Materials Co., Ltd., and N-1919 manufactured by ADEKA Corporation. , NCI-930, NCI-831.
  • oxime ester compound examples include the following compounds.
  • photopolymerization initiators may be used alone or in combination of two or more.
  • a chain transfer agent is a compound having a function of receiving a generated radical and transferring the received radical to another compound.
  • various chain transfer agents can be used as long as they are compounds having the above functions, and examples thereof include mercapto group-containing compounds and carbon tetrachloride, which tend to have a high chain transfer effect. It is more preferable to use a mercapto group-containing compound. It is considered that this is because the bond cleavage is likely to occur due to the small SH binding energy, and a hydrogen drawing reaction or a chain transfer reaction is likely to occur. It is effective for improving sensitivity and surface hardening.
  • Examples of the mercapto group-containing compound include 2-mercaptobenzothiazole, 2-mercaptobenzoimidazole, 2-mercaptobenzoxazole, 3-mercapto-1,2,4-triazole, 2-mercapto-4 (3H) -quinazoline.
  • Mercapto group-containing compounds having an aromatic ring such as ⁇ -mercaptonaphthalene, 1,4-dimethylmercaptobenzene; hexanedithiol, decandithiol, butanediolbis (3-mercaptopropionate), butanediolbisthioglycolate, Ethethyleneglycolbis (3-mercaptopropionate), ethyleneglycolbisthioglycolate, trimethylolpropanetris (3-mercaptopropionate), trimethylolpropanetristhioglycolate, trishydroxyethyltristhiopropionate, penta Erislitholtetrakis (3-mercaptopropionate), pentaerythritoltris (3-mercaptopropionate), butanediolbis (3-mercaptobutyrate), ethyleneglycolbis (3-mercaptobutyrate), trimethylolpropanetris (3-mercaptobut
  • 2-mercaptobenzothiazole and 2-mercaptobenzoimidazole are preferable, and as the aliphatic mercapto group-containing compound, trimethylolpropanthris (3-mercaptopropionate), Pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol tris (3-mercaptopropionate), trimethylol propanthris (3-mercaptobutyrate), pentaerythritol tetrakis (3-mercaptobutyrate), pentaerythritol tris (3-Mercaptobutyrate), 1,3,5-tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -trione are preferred.
  • aliphatic mercapto group-containing compounds are preferable, such as trimethylolpropanthris (3-mercaptopropionate), pentaerythritol tetrakis (3-mercaptopropionate), and pentaerythritoltris (3-mercaptopro).
  • the content ratio of the (E) photopolymerization initiator is not particularly limited, but is preferably 1% by mass or more, more preferably 2% by mass or more in the total solid content of the colored resin composition. 3% by mass or more is further preferable, 4% by mass or more is particularly preferable, 15% by mass or less is more preferable, 10% by mass or less is more preferable, 8% by mass or less is further preferable, and 6% by mass or less is particularly preferable.
  • the patterning characteristics after development tend to be secured, and when it is set to the upper limit value or less, the decrease in transmittance due to excessive addition of the photopolymerization initiator tends to be suppressed.
  • the content ratio of the (E) photopolymerization initiator is preferably 1 to 15% by mass, more preferably 2 to 10% by mass, and 3 to 8% by mass in the total solid content of the colored resin composition.
  • the mass% is more preferable, and 4 to 6% by mass is particularly preferable.
  • the content ratio thereof is not particularly limited, but is preferably 0.1% by mass or more, preferably 0.2% by mass or more in the total solid content of the colored resin composition.
  • the solvent resistance tends to be improved
  • the storage stability tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio thereof is preferably 0.1 to 5% by mass, more preferably 0.2 to 3% by mass in the total solid content of the colored resin composition. , 0.3 to 2% by mass is more preferable, and 0.4 to 1% by mass is particularly preferable.
  • the colored resin composition of the present invention may further contain solids other than the above components, if necessary.
  • a component include a photopolymerizable monomer, a dispersion aid, and a surfactant.
  • the photopolymerizable monomer is not particularly limited as long as it is a polymerizable low molecular weight compound, but is an addition-polymerizable compound having at least one ethylenic double bond (hereinafter, It is referred to as an "ethylenic compound").
  • the ethylenic compound is a compound having an ethylenic double bond such that when the colored resin composition of the present invention is irradiated with active light, it is addition-polymerized by the action of a photopolymerization initiator and cured.
  • the monomer in the present invention means a concept opposite to a so-called polymer substance, and means a concept containing a dimer, a trimer, and an oligomer in addition to the monomer in a narrow sense.
  • the number of ethylenic double bonds contained in the polyfunctional ethylenic monomer is not particularly limited, but is usually 2 or more, preferably 4 or more, more preferably 5 or more, and preferably 5 or more. The number is 8 or less, more preferably 7 or less.
  • the sensitivity tends to be high, and when it is at least the above upper limit value, the solubility in a solvent tends to be improved.
  • the above upper and lower limits can be combined arbitrarily.
  • the number of ethylenic double bonds contained in the polyfunctional ethylenic monomer is preferably 2 to 8, more preferably 2 to 7, further preferably 4 to 7, and particularly preferably 5 to 7.
  • Examples of the ethylenic compound include unsaturated carboxylic acids, esters of unsaturated carboxylic acids and monohydroxy compounds, esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids, aromatic polyhydroxy compounds and unsaturated carboxylic acids.
  • Estelle ester obtained by esterification reaction between unsaturated carboxylic acid and polyvalent carboxylic acid and polyvalent hydroxy compound such as the above-mentioned aliphatic polyhydroxy compound and aromatic polyhydroxy compound, polyisocyanate compound and (meth) acryloyl.
  • Examples thereof include an ethylenic compound having a urethane skeleton reacted with the contained hydroxy compound.
  • ester of the aliphatic polyhydroxy compound and the unsaturated carboxylic acid examples include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylol ethanetriacrylate, pentaerythritol diacrylate, and pentaerythritol triacrylate.
  • acrylic acid moiety of these acrylates is replaced with a methacrylic acid ester instead of a methacrylic acid moiety, an itaconic acid ester substituted with an itaconic acid moiety, a crotonic acid ester substituted with a crotonic acid moiety, or a maleic acid substituted with a maleic acid moiety.
  • Ester can be mentioned.
  • ester of the aromatic polyhydroxy compound and the unsaturated carboxylic acid examples include hydroquinone diacrylate, hydroquinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate, and pyrogallol triacrylate.
  • the ester obtained by the esterification reaction of the unsaturated carboxylic acid with the polyvalent carboxylic acid and the polyvalent hydroxy compound is not necessarily a single substance but may be a mixture.
  • a condensate of acrylic acid, phthalic acid and ethylene glycol a condensate of acrylic acid, maleic acid and diethylene glycol, a condensate of methacrylic acid, terephthalic acid and pentaerythritol, a condensate of acrylic acid, adipic acid, butanediol and glycerin.
  • a condensate of acrylic acid, phthalic acid and ethylene glycol a condensate of acrylic acid, maleic acid and diethylene glycol
  • a condensate of methacrylic acid, terephthalic acid and pentaerythritol a condensate of acrylic acid, adipic acid, butanediol and glycerin.
  • Examples of the ethylenic compound having a urethane skeleton obtained by reacting a polyisocyanate compound with a (meth) acryloyl group-containing hydroxy compound include aliphatic diisocyanates such as hexamethylene diisocyanate and trimethylhexamethylene diisocyanate; cyclohexane diisocyanate and isophorone diisocyanate.
  • Alicyclic diisocyanate aromatic diisocyanates such as tolylene diisocyanate and diphenylmethane diisocyanate, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, 3-hydroxy (1,1,1-triacryloxymethyl) propane, 3- Examples thereof include a reaction product with a (meth) acryloyl group-containing hydroxy compound such as hydroxy (1,1,1-trimethacryloyloxymethyl) propane.
  • examples of the ethylenic compound used in the present invention include acrylamides such as ethylenebisacrylamide; allyl esters such as diallyl phthalate; and vinyl group-containing compounds such as divinylphthalate.
  • the ethylenic compound may be a monomer having an acid value.
  • the monomer having an acid value is an ester of an aliphatic polyhydroxy compound and an unsaturated carboxylic acid, and an acid group is formed by reacting an unreacted hydroxy group of the aliphatic polyhydroxy compound with a non-aromatic carboxylic acid anhydride.
  • the provided polyfunctional monomer is preferable, and in this ester, the polyfunctional monomer in which the aliphatic polyhydroxy compound is pentaerythritol and / or dipentaerythritol is particularly preferable.
  • One of these monomers may be used alone, but since it is difficult to use a single compound in production, two or more of these monomers may be mixed and used. Further, if necessary, a polyfunctional monomer having no acid group and a polyfunctional monomer having an acid group may be used in combination as the monomer.
  • the acid value of the polyfunctional monomer having an acid group is preferably 0.1 to 40 mgKOH / g, and particularly preferably 5 to 30 mgKOH / g. When it is set to the lower limit value or more, the development and dissolution characteristics tend to be good, and when it is set to the upper limit value or less, the manufacturing and handling are improved, and the photopolymerization performance, the surface smoothness of the pixel, etc. are improved. It tends to improve the curability.
  • the acid group as the whole polyfunctional monomer should be adjusted so as to fall within the above range. Is preferable.
  • the polyfunctional monomer having a more preferable acid group is mainly a succinic acid ester of dipentaerythritol hexaacrylate, dipentaerythritol pentaacrylate, or dipentaerythritol pentaacrylate commercially available as TO1382 manufactured by Toa Synthetic Co., Ltd. It is a mixture as an ingredient.
  • This polyfunctional monomer can also be used in combination with other polyfunctional monomers. Further, the polyfunctional monomer described in paragraphs [0056] and [0057] of Japanese Patent Application Laid-Open No. 2013-140346 can also be used.
  • the polymerizable monomer described in Japanese Patent Application Laid-Open No. 2013-195971 from the viewpoint of improving the chemical resistance of the pixel and the linearity of the edge of the pixel, it is preferable to use the polymerizable monomer described in Japanese Patent Application Laid-Open No. 2013-195971. From the viewpoint of achieving both the sensitivity of the coating film and the shortening of the developing time, it is preferable to use the polymerizable monomer described in Japanese Patent Application Laid-Open No. 2013-195974.
  • the content ratio of the photopolymerizable monomer is not particularly limited, but it is usually more than 0% by mass, preferably 5% by mass, in the total solid content of the colored resin composition. % Or more, more preferably 10% by mass or more, still more preferably 15% by mass or more, particularly preferably 20% by mass or more, usually 70% by mass or less, preferably 60% by mass or less, more preferably 50% by mass or less. It is more preferably 40% by mass or less, and particularly preferably 30% by mass or less.
  • the curability of the coating film tends to be high, and when it is at least the above upper limit value, the decrease in alkali developability tends to be suppressed.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the photopolymerizable monomer is preferably more than 0% by mass and 70% by mass or less, preferably 5 to 60% by mass, based on the total solid content of the colored resin composition.
  • the following is more preferable, 10 to 50% by mass is further preferable, 15 to 40% by mass or less is further preferable, and 20 to 30% by mass is particularly preferable.
  • a pigment derivative is contained as a dispersion aid in order to improve the dispersibility of the pigment and the dispersion stability.
  • the pigment derivative include azo-based, phthalocyanine-based, quinacridone-based, benzimidazolone-based, quinophthalone-based, isoindolinone-based, isoindoline-based, dioxazine-based, anthraquinone-based, indanslen-based, perylene-based, and perinone-based.
  • Derivatives such as diketopyrrolopyrrole-based and dioxazine-based pigments can be mentioned.
  • a sulfonic acid group, a sulfonamide group and a quaternary salt thereof, a phthalimidemethyl group, a dialkylaminoalkyl group, a hydroxyl group, a carboxy group, an amide group and the like are directly on the pigment skeleton or an alkyl group, an aryl group or a complex.
  • Examples thereof include those bonded via a ring group and the like, preferably a sulfonic amide group and a quaternary salt thereof, and a sulfonic acid group, and more preferably a sulfonic acid group. Further, these substituents may be substituted in a plurality of one pigment skeleton, or may be a mixture of compounds having different numbers of substitutions.
  • the pigment derivative examples include a sulfonic acid derivative of an azo pigment, a sulfonic acid derivative of a phthalocyanine pigment, a sulfonic acid derivative of a quinophthalone pigment, a sulfonic acid derivative of an isoindrin pigment, a sulfonic acid derivative of an anthraquinone pigment, and a sulfonic acid derivative of a quinacridone pigment.
  • examples thereof include a sulfonic acid derivative of a diketopyrrolopyrrole pigment and a sulfonic acid derivative of a dioxazine pigment.
  • surfactant As the surfactant, various surfactants such as anionic, cationic, nonionic, and amphoteric surfactants can be used, but they adversely affect various properties. Nonionic surfactants are preferred because they are less likely.
  • the content ratio of the surfactant is not particularly limited, but is usually 0.001% by mass or more, preferably 0.01% by mass or more, more preferably 0.05% by mass or more, and further, in the total solid content of the colored resin composition. It is preferably 0.1% by mass or more, usually 10% by mass or less, preferably 1% by mass or less, still more preferably 0.5% by mass or less, and particularly preferably 0.3% by mass or less. The above upper and lower limits can be combined arbitrarily.
  • the content ratio of the surfactant is preferably 0.001 to 10% by mass, more preferably 0.01 to 1% by mass, and 0.05 to 0.5% by mass in the total solid content of the colored resin composition. Is more preferable, and 0.1 to 0.3% by mass is particularly preferable.
  • a colorant dispersion liquid containing (A) a colorant, (B) a solvent, and (C) a dispersant.
  • (A) colorant, (B) solvent, and (C) dispersant are weighed in predetermined amounts, and (A) colorant is dispersed in the dispersion treatment step.
  • a paint conditioner, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer and the like can be used. By performing this dispersion treatment, the colorant is made into fine particles, so that the coating characteristics of the colored resin composition are improved and the transmittance of pixels in the color filter substrate of the product is improved.
  • the colorant When the colorant is dispersed, it is preferable to appropriately use a dispersion aid, a dispersion resin, or the like as described above.
  • a dispersion aid When the dispersion treatment is performed using a sand grinder, it is preferable to use glass beads having a diameter of 0.1 to several mm or zirconia beads.
  • the temperature at the time of the dispersion treatment is usually set in the range of 0 ° C. or higher, preferably room temperature or higher, and usually 100 ° C. or lower, preferably 80 ° C. or lower.
  • the dispersion time may be appropriately adjusted because the appropriate time varies depending on the composition of the colorant dispersion liquid, the size of the sand grinder device, and the like.
  • a colored resin composition can be obtained by mixing a solvent, an alkali-soluble resin, a photopolymerization initiator, and in some cases other components other than the above with the colorant dispersion obtained by the above dispersion treatment to obtain a uniform dispersion solution. Be done. Since fine dust may be mixed in each of the dispersion treatment step and the mixing step, it is preferable to filter the obtained pigment dispersion liquid with a filter or the like.
  • the colorant dispersion liquid of the present invention is a colorant dispersion liquid containing (A) a colorant, (B) a solvent, and (C) a dispersant, wherein (A) a colorant is used. , Contains the phthalocyanine compound (1). (C) The dispersant may contain the dispersant (c1). As described above, the colorant dispersion liquid of the present invention can be used as one of the raw materials of the colored resin composition of the present invention. The colorant dispersion liquid of the present invention can be used as a colorant dispersion liquid for a color filter for forming a color filter.
  • (A) colorant, (B) solvent, and (C) dispersant in the colorant dispersion liquid of the present invention those listed as each component in the colored resin composition can be preferably adopted.
  • the content ratio of the (A) colorant in the colorant dispersion liquid of the present invention is not particularly limited, but is preferably 10% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more in the total solid content. 70% by mass or more is more preferable, 90% by mass or more is particularly preferable, 99.9% by mass or less is preferable, and 99% by mass or less is more preferable.
  • it is set to the lower limit value or more, it can be efficiently dispersed at the time of dispersion, and the contrast improving effect tends to be large, and when it is set to the upper limit value or less, it tends to be dispersed without reaggregation at the time of dispersion.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the (A) colorant in the colorant dispersion is preferably 10 to 99.9% by mass, more preferably 30 to 99.9% by mass, and 50 to 99.9% by mass in the total solid content. Is even more preferable, 70 to 99% by mass is even more preferable, and 90 to 99% by mass is particularly preferable.
  • the content ratio of the phthalocyanine compound (1) in the colorant dispersion of the present invention is not particularly limited, but is preferably 10% by mass or more, more preferably 30% by mass or more, still more preferably 50% by mass or more in the total solid content. 70% by mass or more is more preferable, 90% by mass or more is particularly preferable, 99.9% by mass or less is preferable, and 99% by mass or less is more preferable.
  • it is set to the lower limit value or more, it can be efficiently dispersed at the time of dispersion, and the contrast improving effect tends to be large, and when it is set to the upper limit value or less, it tends to be dispersed without reaggregation at the time of dispersion.
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the phthalocyanine compound (1) in the colorant dispersion is preferably 10 to 99.9% by mass, more preferably 30 to 99.9% by mass, and 50 to 99.9% by mass in the total solid content. Is even more preferable, 70 to 99% by mass is even more preferable, and 90 to 99% by mass is particularly preferable.
  • the content ratio of the phthalocyanine compound (1) in the colorant dispersion liquid of the present invention is not particularly limited, but is preferably 100 parts by mass or more, more preferably 500 parts by mass or more, and 1000 parts by mass with respect to 100 parts by mass of the dispersant (c1). More than parts are more preferable, 3000 parts by mass or more are further preferable, 4000 parts by mass or more are particularly preferable, 20,000 parts by mass or less are preferable, 10,000 parts by mass or less are more preferable, and 8,000 parts by mass or less are further preferable.
  • the dispersant tends to be efficiently adsorbed on the phthalocyanine compound (1) to suppress aggregation of particles, and by setting the value to the upper limit or lower, the dispersant (c1) tends to be suppressed. There is a tendency that aggregation can be suppressed by cross-linking between the phthalocyanine compounds (1).
  • the above upper and lower limits can be combined arbitrarily.
  • the content ratio of the phthalocyanine compound (1) in the colorant dispersion is preferably 100 to 20000 parts by mass, more preferably 500 to 20000 parts by mass, and 1000 to 10000 parts by mass with respect to 100 parts by mass of the dispersant (c1). Is even more preferable, and 3000 to 10000 parts by mass is even more preferable, and 4000 to 8000 parts by mass is particularly preferable.
  • the content ratio of the solvent (B) in the colorant dispersion liquid of the present invention is not particularly limited, but is preferably 30% by mass or more, more preferably 50% by mass or more, further preferably 70% by mass or more, and particularly preferably 80% by mass or more. It is preferable, 99% by mass or less is preferable, 95% by mass or less is more preferable, and 92% by mass or less is further preferable. When it is at least the above lower limit value, the stability over time of the dispersion tends to be improved, and when it is at least the above upper limit value, the handleability tends to be good. The above upper and lower limits can be combined arbitrarily.
  • the content ratio of the solvent (B) in the colorant dispersion is preferably 30 to 99% by mass, more preferably 50 to 99% by mass, further preferably 70 to 95% by mass, and particularly preferably 80 to 92% by mass. ..
  • the content ratio of the (C) dispersant in the colorant dispersion liquid of the present invention is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and 0.5% by mass in the total solid content. % Or more is more preferable, 1% by mass or more is particularly preferable, 10% by mass or less is preferable, 5% by mass or less is more preferable, and 3% by mass or less is further preferable.
  • the phthalocyanine compound (1) can be efficiently dispersed and aggregation tends to be suppressed
  • the dispersant (c1) is the phthalocyanine compound (1).
  • the content ratio of the (C) dispersant in the colorant dispersion is preferably 0.01 to 10% by mass, more preferably 0.1 to 10% by mass, and 0.5 to 5% by mass in the total solid content. Is more preferable, and 1 to 3% by mass is particularly preferable.
  • the content ratio of the dispersant (c1) in the colorant dispersion liquid of the present invention is not particularly limited, but is preferably 0.01% by mass or more, more preferably 0.1% by mass or more, and 0.5% by mass in the total solid content. % Or more is more preferable, 1% by mass or more is particularly preferable, 10% by mass or less is preferable, 5% by mass or less is more preferable, and 3% by mass or less is further preferable.
  • the phthalocyanine compound (1) can be efficiently dispersed and aggregation tends to be suppressed, and when it is at least the above upper limit value, the dispersant (c1) is the phthalocyanine compound (1).
  • the content ratio of the dispersant (c1) in the colorant dispersion is preferably 0.01 to 10% by mass, more preferably 0.1 to 10% by mass, and 0.5 to 5% by mass in the total solid content. Is more preferable, and 1 to 3% by mass is particularly preferable.
  • the color filter according to the present invention has pixels manufactured by using the colored resin composition of the present invention.
  • the material of the transparent substrate of the color filter is not particularly limited as long as it is transparent and has appropriate strength.
  • the material include polyester resins such as polyethylene terephthalate, polyolefin resins such as polypropylene and polyethylene, polycarbonate, polymethylmethacrylate, and polysulfone thermoplastic resin sheets, epoxy resins, unsaturated polyester resins, and poly (meth) acrylics.
  • polyester resins such as polyethylene terephthalate, polyolefin resins such as polypropylene and polyethylene
  • polycarbonate polymethylmethacrylate
  • polysulfone thermoplastic resin sheets epoxy resins, unsaturated polyester resins, and poly (meth) acrylics.
  • thermoplastic resin sheet such as a based resin
  • glass or a heat-resistant resin is preferable from the viewpoint of heat resistance.
  • the thickness of the transparent substrate is usually 0.05 mm or more, preferably 0.1 mm or more, and usually 10 mm or less, preferably 7 mm or less.
  • the film thickness is usually 0.01 ⁇ m or more, preferably 0.05 ⁇ m or more, and usually 10 ⁇ m or less, preferably 5 ⁇ m or less. For example, it is 0.01 to 10 ⁇ m and 0.05 to 5 ⁇ m.
  • the color filter of the present invention can be manufactured by providing a black matrix on a transparent substrate and further forming red, green, and blue pixel images.
  • the colored resin composition of the present invention is preferably used as a coating liquid for forming green pixels (resist pattern) among red, green, and blue pixels.
  • Each process of coating, heat drying, image exposure, development and heat curing is performed to form a pixel image.
  • the black matrix is formed on a transparent substrate by using a light-shielding metal thin film or a colored resin composition for a black matrix.
  • a light-shielding metal material a chromium compound such as metallic chromium, chromium oxide, or chromium nitride, a nickel-tungsten alloy, or the like is used, and these may be laminated in a plurality of layers.
  • These metal light-shielding films are generally formed by an etching method, and after forming a desired pattern in a film shape by a positive photoresist, dicerium ammonium nitrate and perchloric acid and / or nitric acid are added to chromium.
  • a black matrix is formed by using an etching solution mixed with the above, and for other materials, it is carved using an etching solution suitable for the material, and finally the positive photoresist is peeled off with a special release agent. be able to.
  • a thin film of these metals or metal / metal oxides is formed on a transparent substrate by a vapor deposition method or a sputtering method.
  • the coating film is exposed and developed using a photomask having a repeating pattern such as stripes, mosaics, and triangles to form a resist image. After that, the coating film can be etched to form a black matrix.
  • a colored resin composition containing a black colorant is used to form a black matrix.
  • black color materials such as carbon black, graphite, iron black, aniline black, cyanine black, titanium black, etc., or red, green, blue, etc. appropriately selected from inorganic or organic pigments and dyes.
  • a black matrix can be formed by using a colored resin composition containing a black color material by mixing in the same manner as the method for forming red, green, and blue pixel images described below.
  • a colored resin composition of one of red, green, and blue is applied onto a transparent substrate provided with a black matrix, dried, and then a photomask is placed on the coating film.
  • a pixel image is formed by image exposure, development, and optionally heat curing or photocuring via a photomask. By performing this operation for each of the three colored resin compositions of red, green, and blue, a color filter image can be formed.
  • the colored resin composition for a color filter can be applied by a spinner method, a wire bar method, a flow coat method, a die coat method, a roll coat method, a spray coat method, or the like.
  • a spinner method a wire bar method
  • a flow coat method a die coat method
  • a roll coat method a spray coat method
  • the amount of coating liquid used is significantly reduced, there is no influence of mist adhering when the spin coat method is used, and the generation of foreign substances is suppressed. It is preferable from the above viewpoint.
  • the thickness of the coating film after drying is usually 0.2 ⁇ m or more, preferably 0.5 ⁇ m or more, more preferably 0.8 ⁇ m or more, and usually 20 ⁇ m or less, preferably 10 ⁇ m or less, more preferably 5 ⁇ m.
  • the range is as follows. For example, it is 0.2 to 20 ⁇ m, 0.5 to 10 ⁇ m, and 0.8 to 5 ⁇ m.
  • [4-4] Drying of Coating Film It is preferable to dry the coating film after applying the colored resin composition to the substrate by a drying method using a hot plate, an IR oven, or a convection oven. Usually, after pre-drying, it is heated again to dry.
  • the conditions for pre-drying can be appropriately selected according to the type of the solvent component, the performance of the dryer used, and the like.
  • the drying temperature and drying time are selected according to the type of solvent component, the performance of the dryer used, and the like. Specifically, the drying temperature is usually 40 ° C. or higher, preferably 50 ° C. or higher, and usually 80 ° C. or higher.
  • the temperature is in the range of ° C. or lower, preferably 70 ° C. or lower, and the drying time is usually in the range of 15 seconds or longer, preferably 30 seconds or longer, and usually 5 minutes or shorter, preferably 3 minutes or shorter.
  • the temperature condition for reheating and drying is preferably higher than the pre-drying temperature, specifically, usually 50 ° C. or higher, preferably 70 ° C. or higher, and usually 200 ° C. or lower, preferably 160 ° C. or lower, particularly preferably 130 ° C. or higher. It is in the range of °C or less.
  • the drying time is usually 10 seconds or longer, particularly preferably 15 seconds or longer, and usually 10 minutes or shorter, preferably 5 minutes or longer, although it depends on the heating temperature. The higher the drying temperature, the better the adhesiveness to the transparent substrate, but if it is too high, the binder resin may be decomposed, inducing thermal polymerization and causing development defects.
  • a vacuum drying method may be used in which the coating film is dried in the vacuum chamber without raising the temperature.
  • Exposure Step Image exposure is performed by superimposing a negative matrix pattern on a coating film of a colored resin composition and irradiating a light source of ultraviolet rays or visible light through this mask pattern. At this time, if necessary, in order to prevent the sensitivity of the photopolymerizable layer from being lowered by oxygen, exposure may be performed after forming an oxygen blocking layer such as a polyvinyl alcohol layer on the photopolymerizable layer.
  • the light source used for the above image exposure is not particularly limited.
  • the light source examples include lamp light sources such as xenon lamps, halogen lamps, tungsten lamps, high pressure mercury lamps, ultrahigh pressure mercury lamps, metal halide lamps, medium pressure mercury lamps, low pressure mercury lamps, carbon arcs, fluorescent lamps, argon ion lasers, YAG lasers, etc.
  • lamp light sources such as xenon lamps, halogen lamps, tungsten lamps, high pressure mercury lamps, ultrahigh pressure mercury lamps, metal halide lamps, medium pressure mercury lamps, low pressure mercury lamps, carbon arcs, fluorescent lamps, argon ion lasers, YAG lasers, etc.
  • laser light sources such as an excima laser, a nitrogen laser, a helium cadmium laser, and a semiconductor laser.
  • An optical filter can also be used when irradiating light of a specific wavelength for use.
  • a coating film using the colored resin composition according to the present invention is subjected to image exposure with the above-mentioned light source, and then a surfactant and an alkaline compound are applied.
  • a surfactant and an alkaline compound are applied.
  • the aqueous solution can further contain an organic solvent, a buffer, a complexing agent, a dye or a pigment.
  • alkaline compound examples include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, and phosphorus.
  • Inorganic alkaline compounds such as potassium acid, sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide, mono-di or triethanolamine, mono-di- Or trimethylamine, mono-di- or triethylamine, mono- or diisopropylamine, n-butylamine, mono-di- or triisopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium hydroxide (TMAH), choline, etc.
  • Examples include organic alkaline compounds. These alkaline compounds may be used alone or in combination of two or more.
  • the surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and monoglyceride alkyl esters, and alkylbenzene sulfonic acids.
  • nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, and monoglyceride alkyl esters, and alkylbenzene sulfonic acids.
  • anionic surfactants such as salts, alkylnaphthalene sulfonates, alkyl sulfates, alkyl sulfonates and sulfosuccinic acid ester salts
  • amphoteric surfactants such as alkyl betaines and amino acids.
  • the organic solvent examples include isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol and diacetone alcohol.
  • the organic solvent can be used in combination with an aqueous solution.
  • the conditions of the development process are not particularly limited, but the development temperature is usually in the range of 10 ° C. or higher, particularly 15 ° C. or higher, further 20 ° C. or higher, and usually 50 ° C. or lower, particularly 45 ° C. or lower, further 40 ° C. or lower. Is preferable.
  • the developing method can be any one of a dipping developing method, a spray developing method, a brush developing method, an ultrasonic developing method and the like.
  • thermosetting treatment The color filter after development is subjected to a thermosetting treatment.
  • the thermosetting treatment conditions at this time are selected in a temperature range of usually 100 ° C. or higher, preferably 150 ° C. or higher, and usually 280 ° C. or lower, preferably 250 ° C. or lower, and the time is 5 minutes or longer and 60 minutes or shorter. Selected by range.
  • the formation of a one-color patterning image is completed. This process is repeated in sequence to pattern black, red, green, and blue to form a color filter.
  • the order of patterning of the four colors is not limited to the above-mentioned order.
  • the color filter according to the present invention forms a transparent electrode such as ITO on an image in this state and is used as a part of parts such as a color display and a liquid crystal display device.
  • a top coat layer such as polyamide or polyimide can be provided on the image if necessary.
  • IPS mode plane alignment type drive system
  • a transparent electrode may not be formed.
  • Image display device panel
  • the image display device of the present invention has the color filter of the present invention.
  • the liquid crystal display device and the organic EL display device will be described in detail as the image display device.
  • [5-1] Liquid Crystal Display Device A method for manufacturing a liquid crystal display device according to the present invention will be described.
  • an alignment film is usually formed on the color filter of the present invention, a spacer is sprayed on the alignment film, and then the liquid crystal display device is bonded to a facing substrate to form a liquid crystal cell.
  • the liquid crystal is injected into the cell and connected to the counter electrode to complete the process.
  • a resin film such as polyimide is suitable.
  • a gravure printing method and / or a flexographic printing method is usually adopted for forming the alignment film, and the thickness of the alignment film is several tens of nm.
  • After the alignment film is hardened by heat firing, it is surface-treated by irradiation with ultraviolet rays or treatment with a rubbing cloth to obtain a surface state in which the inclination of the liquid crystal can be adjusted.
  • the spacer used has a size corresponding to the gap (gap) with the facing substrate, and is usually preferably 2 to 8 ⁇ m.
  • a photospacer (PS) of a transparent resin film can be formed on a color filter substrate by a photolithography method, and this can be used instead of the spacer.
  • As the facing substrate an array substrate is usually used, and a TFT (thin film transistor) substrate is particularly suitable.
  • the gap for bonding to the facing substrate varies depending on the application of the liquid crystal display device, but is usually selected in the range of 2 ⁇ m or more and 8 ⁇ m or less.
  • the parts other than the liquid crystal injection port are sealed with a sealing material such as epoxy resin.
  • the sealing material is cured by UV irradiation and / or heating, and the periphery of the liquid crystal cell is sealed.
  • the liquid crystal cell whose periphery is sealed is cut into panel units, then depressurized in a vacuum chamber, the liquid crystal injection port is immersed in the liquid crystal, and then the inside of the chamber leaks to inject the liquid crystal into the liquid crystal cell. ..
  • the degree of decompression in the liquid crystal cell is usually in the range of 1 ⁇ 10 ⁇ 2 Pa or more, preferably 1 ⁇ 10 -3 or more, and usually 1 ⁇ 10 -7 Pa or less, preferably 1 ⁇ 10 -6 Pa or less. .. Further, it is preferable to heat the liquid crystal cell at the time of depressurization, and the heating temperature is usually in the range of 30 ° C. or higher, preferably 50 ° C. or higher, and usually 100 ° C. or lower, preferably 90 ° C. or lower.
  • the heat retention at the time of depressurization is usually in the range of 10 minutes or more and 60 minutes or less, and then immersed in the liquid crystal display.
  • a liquid crystal display device (panel) is completed by sealing the liquid crystal injection port of the liquid crystal cell into which the liquid crystal is injected by curing the UV curable resin.
  • the type of liquid crystal is not particularly limited, and is a conventionally known liquid crystal such as an aromatic type, an aliphatic type, or a polycyclic compound, and may be any of a lyotropic liquid crystal, a thermotropic liquid crystal, and the like.
  • thermotropic liquid crystal a nematic liquid crystal, a smestic liquid crystal, a cholesteric liquid crystal and the like are known, but any of them may be used.
  • the pixels 20 are formed on the transparent support substrate 10 by the colored resin composition of the present invention.
  • a multicolored organic EL element is manufactured by laminating an organic illuminant 500 on a blue color filter on which an organic protective layer 30 is formed and an inorganic oxide film 40.
  • a method of laminating the organic illuminant 500 a method of sequentially forming a transparent anode 50, a hole injection layer 51, a hole transport layer 52, a light emitting layer 53, an electron injection layer 54, and a cathode 55 on the upper surface of a color filter, or Examples thereof include a method of bonding the organic light emitter 500 formed on another substrate onto the inorganic oxide film 40.
  • the organic EL element 100 produced in this way can be applied to both a passive drive type organic EL display device and an active drive type organic EL display device.
  • ⁇ Parthalocyanine compound A> A phthalocyanine compound A having the following chemical structure synthesized based on Example 30 of Japanese Patent Application Laid-Open No. 05-345861 was used.
  • Et in the formula represents ethyl.
  • the A block has a repeating unit represented by the following formula (1a)
  • the B block has a repeating unit represented by the following formula (2a).
  • the content ratios of the repeating unit represented by the following formula (1a) and the repeating unit represented by the following formula (2a) in all the repeating units are 33.3 mol% and 6.7 mol%, respectively.
  • the amine value is 120 mgKOH / g and the acid value is 0 mgKOH / g.
  • the content ratio of the repeating unit represented by the formula (c1-2) is the sum of the content ratio of the repeating unit represented by the formula (c1-1) and the content ratio of the repeating unit represented by the formula (c1-2). It is 0 mol% with respect to.
  • the A block has a repeating unit represented by the following formulas (1d) and (2d), and the B block has a repeating unit represented by the following formula (3d).
  • the content ratios of the repeating unit represented by the following formula (1d), the repeating unit represented by the following formula (2d), and the repeating unit represented by the following formula (3d) in all the repeating units are 11.1 respectively. Mol%, 22.2 mol%, and 6.7 mol%.
  • the amine value is 70 mgKOH / g and the acid value is 0 mgKOH / g.
  • the content ratio of the repeating unit represented by the formula (c1-2) is the sum of the content ratio of the repeating unit represented by the formula (c1-1) and the content ratio of the repeating unit represented by the formula (c1-2). It is 33 mol% with respect to.
  • the A block has a repeating unit represented by the following formulas (1e) and (2e)
  • the B block has a repeating unit represented by the following formula (3e).
  • the content ratios of the repeating units represented by the following formulas (1e), (2e) and (3e) in all the repeating units are 30.1 mol%, 3.3 mol% and 6.7 mol%, respectively.
  • the amine value is 10 mgKOH / g and the acid value is 0 mgKOH / g.
  • the content ratio of the repeating unit represented by the formula (c1-2) is the sum of the content ratio of the repeating unit represented by the formula (c1-1) and the content ratio of the repeating unit represented by the formula (c1-2). 90 mol% with respect to.
  • reaction vessel was replaced with air, 0.7 parts by mass of trisdimethylaminomethylphenol and 0.12 parts by mass of hydroquinone were added to 50 parts by mass of acrylic acid, and the reaction was continued at 120 ° C. for 6 hours. Then, 13 parts by mass of tetrahydrophthalic anhydride (THPA) and 0.7 parts by mass of triethylamine were added, and the mixture was reacted at 120 ° C. for 3.5 hours.
  • THPA tetrahydrophthalic anhydride
  • the polystyrene-equivalent weight average molecular weight Mw measured by GPC of the alkali-soluble resin A thus obtained was about 9000, the acid value was 25 mgKOH / g, and the double bond equivalent was 260 g / mol.
  • a mixed solvent consisting of 25.0 parts by mass of phthalocyanine compound A, dispersants A to C (in terms of solid content) in the amounts shown in Table 1, 184 parts by mass of propylene glycol monomethyl ether acetate and 46 parts by mass of propylene glycol monomethyl ether as a solvent. 574 parts by mass of zirconia beads having a diameter of 0.5 mm (including those derived from a dispersant) were filled in a stainless steel container and dispersed in a paint shaker for 6 hours. After the dispersion was completed, the beads and the dispersion were separated by a filter to prepare a green dispersion.
  • Me in the formula represents methyl.
  • the obtained colored resin composition was applied on a 50 mm square, 0.7 mm thick glass substrate (AN100, manufactured by AGC) with a spin coater, and then dried at 90 ° C. for 90 seconds.
  • an exposure process was performed using a 2 kW high-pressure mercury lamp with an exposure amount of 60 mJ / cm 2 and an illuminance of 30 mW / cm 2 .
  • the development treatment was carried out using a 0.1 mass% sodium carbonate aqueous solution at a developer temperature of 23 ° C. for 50 seconds.
  • a spray water washing treatment was carried out at a water pressure of 1 kg / cm 2 for 10 seconds, and a thermosetting treatment was carried out at 230 ° C.
  • Table 2 shows the contrast measured by a contrast meter (CT-1) manufactured by Tsubosaka Electric Co., Ltd. using the obtained colored substrate.
  • the obtained colored resin composition was applied by a spin coating method on a glass substrate (manufactured by AGC, AN100) having a size of 50 mm and a thickness of 0.7 mm.
  • the rotation speed was adjusted so that the film thickness after the thermosetting treatment was 2.5 um.
  • Each coating film was prebaked at 90 ° C. for 90 seconds.
  • an exposure process was performed using a 2 kW high-pressure mercury lamp at an exposure amount of 40 mJ / cm 2 and an illuminance of 30 mW / cm 2 via an exposure mask having a straight portion having a length of 50 ⁇ m.
  • thermosetting treatment was performed at 230 ° C. for 20 minutes to prepare a pattern substrate.
  • the linear shape of the pattern was measured using an optical microscope, and the plate-making property was evaluated according to the following evaluation criteria.
  • the phthalocyanine compound (1) has low solubility in a solvent and requires a dispersant in order to be uniformly present in the system.
  • a dispersant (c1) having a high amine value that is, a dispersant having a large amount of amine components
  • the unshared electron pair of the amine component in the dispersant (c1) is mutual with the central metal in the phthalocyanine compound (1).
  • the dispersant (c1) acts to efficiently adsorb to the particles of the phthalocyanine compound (1), and the steric repulsion between the adsorbed dispersants promotes the dispersion stability of the phthalocyanine compound (1), resulting in aggregates of the particles. It is considered that the light scattering due to the generation is suppressed and the contrast is high. Further, it is considered that since the dispersion stability is high, the curing at the time of exposure proceeds efficiently, the development resistance is improved, and the plate-making property is improved. Therefore, it is considered that the higher the amine value of the dispersant (c1), the more remarkable the effect.
  • the stability of the phthalocyanine compound itself is determined by the type of substituent of the phthalocyanine skeleton and the number of substituents, and tends to be stable by having a halogen atom as a substituent, particularly a fluorine atom having a large electronegativity, and further, fluorine.
  • the high stability of the phthalocyanine compound itself suppresses the aggregation of the compounds in heat curing, thereby suppressing the light scattering due to the generation of aggregates, and the luminance (LY) tends to be less likely to decrease.
  • the phthalocyanine compound (1) has a fluorine atom having a high electronegativity as a substituent, and in particular, since the number of the substituents is as large as 6 or more, the stability of the phthalocyanine compound itself becomes high and heat curing is performed. It is considered that by suppressing the aggregation of the compounds in the above, light scattering due to the generation of aggregates is also suppressed, and the brightness (LY) is less likely to decrease.
  • Transparent support substrate 20 pixels 30 Organic protective layer 40 Inorganic oxide film 50 Transparent anode 51 Hole injection layer 52 Hole transport layer 53 Light emitting layer 54 Electron injection layer 55 Cathode 100 Organic EL element 500 Organic light emitter

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Abstract

L'invention concerne une composition de résine colorée atteignant une luminance élevée et un contraste satisfaisant. Cette composition de résine colorée comprend (A) un colorant, (B) un solvant, (C) un ou plusieurs dispersants, (D) une résine soluble dans les alcalis, et (E) un initiateur de photopolymérisation, et elle est caractérisée en ce que le colorant (A) comprend un composé de phtalocyanine ayant une structure chimique spécifique et en ce que les dispersants (C) comprennent un dispersant (c1) ayant une valeur d'amine de 50 mg de KOH/g ou plus, le rapport de la teneur du composé de phtalocyanine à la teneur du dispersant (c1), (composé de phtalocyanine)/(dispersant (c1)), étant de 5 ou plus.
PCT/JP2021/027149 2020-07-31 2021-07-20 Composition de résine colorée, filtre coloré, dispositif d'affichage d'image et dispersion de colorant WO2022024876A1 (fr)

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JP2019113732A (ja) * 2017-12-25 2019-07-11 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置
JP2019144543A (ja) * 2018-02-16 2019-08-29 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置
JP2020042263A (ja) * 2018-09-10 2020-03-19 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置

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JP5581566B2 (ja) 2007-08-24 2014-09-03 住友化学株式会社 着色硬化性組成物
JP6205193B2 (ja) 2012-07-30 2017-09-27 富士フイルム株式会社 着色硬化性組成物、これを用いたカラーフィルタ
JP6005258B2 (ja) 2013-03-27 2016-10-12 富士フイルム株式会社 着色組成物、感光性着色組成物、カラーフィルタ及びその製造方法、固体撮像素子、並びに画像表示装置

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JP2019113732A (ja) * 2017-12-25 2019-07-11 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置
JP2019144543A (ja) * 2018-02-16 2019-08-29 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置
JP2020042263A (ja) * 2018-09-10 2020-03-19 三菱ケミカル株式会社 着色樹脂組成物、カラーフィルタ、及び画像表示装置

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