WO2016136936A1 - Composition colorante, film durci, filtre coloré, procédé de fabrication d'un filtre coloré, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et polymère - Google Patents

Composition colorante, film durci, filtre coloré, procédé de fabrication d'un filtre coloré, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et polymère Download PDF

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Publication number
WO2016136936A1
WO2016136936A1 PCT/JP2016/055788 JP2016055788W WO2016136936A1 WO 2016136936 A1 WO2016136936 A1 WO 2016136936A1 JP 2016055788 W JP2016055788 W JP 2016055788W WO 2016136936 A1 WO2016136936 A1 WO 2016136936A1
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group
rtp
general formula
anion
carbon atoms
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PCT/JP2016/055788
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English (en)
Japanese (ja)
Inventor
福田　誠
藤田　明徳
崇一郎 長田
晃男 片山
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富士フイルム株式会社
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Priority to KR1020177022893A priority Critical patent/KR101957754B1/ko
Priority to JP2017502507A priority patent/JP6461304B2/ja
Publication of WO2016136936A1 publication Critical patent/WO2016136936A1/fr

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    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • 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
    • C09B11/00—Diaryl- or thriarylmethane dyes
    • C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
    • C09B11/10—Amino derivatives of triarylmethanes
    • C09B11/12—Amino derivatives of triarylmethanes without any OH group bound to an aryl nucleus
    • C09B11/20—Preparation from other triarylmethane derivatives, e.g. by substitution, by replacement of substituents
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
    • C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
    • 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
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/103—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing a diaryl- or triarylmethane dye
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/201—Filters in the form of arrays
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
    • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G03F7/0388—Macromolecular compounds which are rendered insoluble or differentially wettable with ethylenic or acetylenic bands in the side chains of the photopolymer
    • 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
    • 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
    • G03F7/26—Processing photosensitive materials; Apparatus therefor

Definitions

  • the present invention relates to a colored composition, a cured film, a color filter, a method for producing a color filter, a solid-state imaging device, an image display device, and a polymer.
  • the coloring composition is used for manufacturing a color filter and the like.
  • color filters tend to be used not only for monitors but also for televisions in liquid crystal display device applications.
  • color filters are required to have high color characteristics in terms of chromaticity and contrast.
  • color filters for image sensors solid-state imaging devices
  • Patent Documents 1 and 2 disclose a colored composition containing a compound having a triarylmethane structure.
  • a coloring composition used for a color filter or the like is required to be able to form a film having excellent heat resistance and solvent resistance.
  • the coloring compositions disclosed in Patent Documents 1 and 2 are not sufficient in heat resistance and solvent resistance.
  • an object of the present invention is to provide a coloring composition, a cured film, a color filter, a method for producing a color filter, a solid-state imaging device, an image display device, and a polymer excellent in heat resistance and solvent resistance.
  • the polymer includes a repeating unit A having a triarylmethane structure and a repeating unit B having a crosslinkable group, and has a weight average molecular weight of 3000 to
  • the inventors have found that the above object can be achieved by using a polymer having a triarylmethane structure having a weight average molecular weight of 1500 or less and having a triarylmethane structure of 20% by mass or less, and has completed the present invention.
  • the present invention provides the following.
  • Polymer TP containing at least one repeating unit A having a triarylmethane structure selected from general formula (TP1) and general formula (TP2) and a repeating unit B having a crosslinkable group, and polymerization And a sex compound,
  • the polymer TP has a weight average molecular weight of 3000 to 500,000, and the content of the compound A having a triarylmethane structure and a weight average molecular weight of 1500 or less is 20% by mass or less based on the mass of the polymer TP.
  • Rtp 1 to Rtp 4 each independently represents a hydrogen atom, an alkyl group or an aryl group
  • Rtp 5 , Rtp 6 , Rtp 8 , Rtp 9 and Rtp 11 are each Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group or NRtp 71 Rtp 72
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group or an aryl group
  • Rtp 10 represents a hydrogen atom, an alkyl group or an aryl group
  • a, b, c and d each independently represent an integer of 0 to 4; when a, b, c and d are 2 or more, Rtp 5 , Rtp 6 , Rtp 8 and Rtp 9 may be linked to each other to form a ring
  • X represents an anion, or X is absent and Rtp 1 to R
  • the crosslinkable group of the repeating unit B is at least one selected from a group containing an ethylenically unsaturated bond, an epoxy group, an oxetanyl group, an oxazoline group, a group represented by —C—O—R, and a carbonate group.
  • X is at least one anion selected from fluorine anion, chlorine anion, bromine anion, iodine anion, cyanide ion, perchlorate anion, borate anion, PF 6 ⁇ and SbF 6 ⁇ , and ⁇ Selected from SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , a compound having at least one structure selected from the structure represented by the following general formula (A1) and the structure represented by the following general formula (A2)
  • ⁇ 6> The colored composition according to any one of ⁇ 1> to ⁇ 5>, wherein X is a compound containing a bis (sulfonyl) imide anion, a tris (sulfonyl) methide anion, or a sulfonate anion.
  • X is a compound containing a crosslinkable group.
  • X is a polymer containing a repeating unit having an anion moiety.
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having a carbon number of 1 ⁇ 6
  • Rtp 22 each independently represents an aryl group having 6 to 10 carbon atoms
  • Rtp 71 is represents an alkyl group or an aryl group
  • X is either an anion, X is at least one contains an anion of Rtp 21, Rtp 22 and Rtp 71 to absent; repeated either Rtp 21, Rtp 22 and Rtp 71 is It represents the binding site with unit A.
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 22 each independently represents an aryl group having 6 to 10 carbon atoms
  • Rtp 71a Represents an alkylene group or an arylene group
  • L 1 represents a single bond or a divalent linking group
  • Rtp 31 represents a hydrogen atom or a methyl group
  • X represents an anion, or X does not exist and Rtp At least one of 21 and Rtp 22 contains an anion.
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 24 each independently represents an alkyl group having 1 to 4 carbon atoms
  • Rtp 25 Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • Rtp 71a represents an alkylene group or an arylene group
  • Rtp 31 represents a hydrogen atom or a methyl group
  • L 1 represents a single bond or X represents an anion, or X does not exist and at least one of Rtp 21 and Rtp 24 includes an anion.
  • the polymer TP contains a repeating unit derived from at least one of (meth) acrylic acid, (meth) acrylic acid ester, and (meth) acrylic acid amide, according to any one of ⁇ 1> to ⁇ 12> Coloring composition.
  • ⁇ 15> The colored composition according to any one of ⁇ 1> to ⁇ 14>, comprising a photopolymerization initiator.
  • ⁇ 16> The colored composition according to any one of ⁇ 1> to ⁇ 15>, comprising a bis (trifluoromethanesulfonyl) imide salt.
  • ⁇ 17> The colored composition according to any one of ⁇ 1> to ⁇ 16>, which is used for forming a colored layer of a color filter.
  • ⁇ 18> A cured film obtained by curing the colored composition according to any one of ⁇ 1> to ⁇ 17>.
  • ⁇ 19> A color filter having the cured film according to ⁇ 18>.
  • ⁇ 20> A step of forming a colored composition layer using the colored composition according to any one of ⁇ 1> to ⁇ 17>, a step of exposing the colored composition layer in a pattern, and a coloring composition layer And a step of developing and removing the unexposed portion to form a colored pattern.
  • ⁇ 21> A step of forming a colored composition layer using the colored composition according to any one of ⁇ 1> to ⁇ 17> and curing to form a colored layer; and forming a photoresist layer on the colored layer
  • a method of manufacturing a color filter comprising: a step of patterning a photoresist layer by exposure and development to obtain a resist pattern; and a step of dry etching the colored layer using the resist pattern as an etching mask.
  • a solid-state imaging device having the color filter according to ⁇ 19>.
  • An image display device having the color filter according to ⁇ 19>.
  • a polymer comprising a repeating unit represented by the following general formula (TP-7), wherein the polymer has a weight average molecular weight of 3000 to 500,000 and a compound having a triarylmethane structure and having a weight average molecular weight of 1500 or less.
  • each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 4 represents a hydrogen atom or a methyl group
  • R 1a represents an alkylene group or an arylene group.
  • L 11 represents a single bond or a divalent linking group having 1 to 30 carbon atoms
  • L 12 and L 13 represent a single bond or a divalent linking group having 1 to 30 carbon atoms.
  • R 2 represents a hydrocarbon group having 1 to 10 carbon atoms
  • R 3 represents a crosslinkable group
  • X represents a compound containing a bis (sulfonyl) imide anion, a tris (sulfonyl) methide anion or a sulfonate anion
  • a to d are mass ratios of repeating units, a and d each represent a number exceeding 0, and b and c each independently represent a number of 0 or more.
  • a colored composition a cured film, a color filter, a method for producing a color filter, a solid-state imaging device, an image display device, and a polymer excellent in heat resistance and solvent resistance.
  • the total solid content refers to the total mass of components excluding the solvent from the total composition of the colored composition.
  • the description which does not describe substitution and unsubstituted includes the thing which has a substituent with the thing which does not have a substituent.
  • the “alkyl group” includes not only an alkyl group having no substituent (unsubstituted alkyl group) but also an alkyl group having a substituent (substituted alkyl group).
  • the “radiation” in the present specification means, for example, an emission line spectrum of a mercury lamp, far ultraviolet rays represented by an excimer laser, extreme ultraviolet rays (EUV light), X-rays, electron beams, and the like.
  • light means actinic rays or radiation.
  • exposure in this specification refers not only to exposure with far-ultraviolet rays such as mercury lamps and excimer lasers, X-rays, EUV light, but also particle beams such as electron beams and ion beams. This drawing is also included in the exposure.
  • (meth) acrylate represents both and / or acrylate and methacrylate
  • (meth) acryl represents both and / or acrylic and “(meth) acrylic”.
  • Acryloyl represents both and / or acryloyl and methacryloyl.
  • the monomer in this specification is distinguished from an oligomer and a polymer, and refers to a compound having a weight average molecular weight of 2,000 or less.
  • the polymerizable compound refers to a compound having a polymerizable functional group.
  • the polymerizable functional group refers to a group that participates in a polymerization reaction.
  • Me in the chemical formula represents a methyl group
  • Et represents an ethyl group
  • Pr represents a propyl group
  • Bu represents a butyl group
  • Ph represents a phenyl group.
  • the term “process” is not limited to an independent process, and is included in the term if the intended action of the process is achieved even when it cannot be clearly distinguished from other processes.
  • the weight average molecular weight and the number average molecular weight in the present invention are defined as polystyrene conversion values in gel permeation chromatography (GPC) measurement unless otherwise specified.
  • the colored composition of the present invention includes a repeating unit A having a triarylmethane structure, which will be described later, and a polymer TP containing a repeating unit B having a crosslinkable group, and a polymerizable compound.
  • the content of Compound A having a molecular weight of 3000 to 500,000 and having a triarylmethane structure and a weight average molecular weight of 1500 or less is 20% by mass or less based on the mass of the polymer TP.
  • the coloring composition excellent in heat resistance and solvent resistance can be provided.
  • a film having a good voltage holding ratio can be formed.
  • the polymer TP includes a repeating unit A having a triarylmethane structure.
  • the repeating unit A preferably has a structure represented by the following general formula (A).
  • the repeating unit A is preferably contained at 1 to 99% by mass in all the repeating units of the polymer TP.
  • the upper limit is more preferably 95% by mass or less, and still more preferably 90% by mass or less.
  • the lower limit is more preferably 5% by mass or more. If content of the repeating unit A is the said range, color value will become more favorable.
  • X 1 represents a main chain of repeating units.
  • L 1 represents a single bond or a divalent linking group.
  • DyeI represents a triarylmethane structure represented by general formula (TP1) or general formula (TP2) described later.
  • X 1 represents a main chain of repeating units, usually represents a linking group formed by polymerization reaction, for example, having a (meth) acrylic group, styrene group, a vinyl group, an ether group A main chain derived from a compound is preferred. An embodiment having a main chain cyclic alkylene group is also preferred. In addition, it has couple
  • X 1 is not particularly limited as long as it is a linking group formed from a known polymerizable monomer, but is particularly preferably a linking group represented by the following (XX-1) to (XX-24), (XX— 1) (meth) acrylic linking chains represented by (XX-2), styrene linking chains represented by (XX-10) to (XX-17), (XX-18) and (XX-19) ) And a vinyl-based linking chain represented by (XX-24), and (meth) acrylic linking chains represented by (XX-1) and (XX-2), ( More preferably selected from styrene-based linking chains represented by (XX-10) to (XX-17) and vinyl-based linking chains represented by (XX-24), and (XX-1) and (XXX- (Meth) acrylic connecting chain represented by 2) and (XX-11) In styrene linking chain represented are especially preferred.
  • L 1 represents a divalent linking group
  • an alkylene group, an arylene group, a heterocyclic group —CH ⁇ CH—, —O—, —S—, —CO—, —NR—, —CONR—, —COO —, —OCO—, —SO 2 — and a linking group obtained by combining two or more thereof are preferred.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • the alkylene group preferably has 1 to 30 carbon atoms.
  • the upper limit is more preferably 25 or less, and still more preferably 20 or less.
  • the lower limit is more preferably 2 or more, and still more preferably 3 or more.
  • the alkylene group may be linear, branched or cyclic.
  • the carbon number of the arylene group is preferably 6 to 20, and more preferably 6 to 12.
  • L 1 is preferably an alkylene group, an arylene group, —NH—, —CO—, —O—, —COO—, —OCO— or a linking group in which two or more thereof are combined, and includes an alkylene group, an arylene group, and , —O—, —COO—, and a divalent group formed by combining one or more selected from —OCO— are more preferable, and an alkylene group or alkylene groups are —O—, —COO—, and —OCO.
  • the number of atoms constituting the chain connecting X 1 and Dye I is preferably 1 or more, more preferably 2 or more, further preferably 3 or more, and particularly preferably 5 or more.
  • the upper limit is preferably 20 or less, for example.
  • a low-molecular triarylmethane compound that is unreacted or insufficiently reacted can be effectively suppressed.
  • the number of atoms constituting the chain connecting X 1 and Dye I is ten.
  • the numbers written in the structural formula are the number of atoms constituting the chain connecting X 1 and DyeI.
  • L 1 represents a single bond
  • X 1 is bonded to any one of Rtp 1 to Rtp 11 , Rtp 71 and Rtp 72 in the general formulas (TP1) and (TP2), and Rtp 71 or Rtp 72 It is preferable that it is couple
  • L 1 represents a divalent linking group
  • L 1 is bonded to any one of Rtp 1 to Rtp 11 , Rtp 71 and Rtp 72 in the general formulas (TP1) and (TP2), and Rtp 71 or Rtp 72 is preferably bonded.
  • the repeating unit A has a triarylmethane structure selected from the general formula (TP1) and the general formula (TP2).
  • Rtp 1 to Rtp 4 each independently represents a hydrogen atom, an alkyl group or an aryl group
  • Rtp 5 , Rtp 6 , Rtp 8 , Rtp 9 and Rtp 11 are each Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group or NRtp 71 Rtp 72
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group or an aryl group
  • Rtp 10 represents a hydrogen atom, an alkyl group or an aryl group
  • a, b, c and d each independently represent an integer of 0 to 4; when a, b, c
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group, or an aryl group. It is preferable that one of Rtp 1 and Rtp 2 is an alkyl group and the other is an aryl group. It is preferable that one of Rtp 3 and Rtp 4 is an alkyl group and the other is an aryl group.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 to 3 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, but is preferably linear or branched.
  • the alkyl group is preferably unsubstituted. Examples of the substituent include the substituents mentioned in the section of the substituent group A described later.
  • the aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 carbon atoms. Examples of the substituent that the aryl group may have include the substituents mentioned in the section of the substituent group A described later.
  • Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group, or NRtp 71 Rtp 72 , preferably a hydrogen atom or NRtp 71 Rtp 72 , and more preferably NRtp 71 Rtp 72 .
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 5 carbon atoms, and still more preferably 1 to 3 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, but is preferably linear. Examples of the substituent that the alkyl group may have include the substituents mentioned in the section of Substituent Group A described later.
  • the aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 carbon atoms.
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group or an aryl group, preferably a hydrogen atom or an alkyl group.
  • the alkyl group preferably has 1 to 10 carbon atoms, more preferably 1 to 8 carbon atoms, and still more preferably 1 to 6 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, and is preferably cyclic.
  • the alkyl group may be substituted. Examples of the substituent that the alkyl group may have include the substituents mentioned in the section of Substituent Group A described later.
  • the aryl group preferably has 6 to 18 carbon atoms, more preferably 6 to 12 carbon atoms, and still more preferably 6 carbon atoms.
  • Examples of the substituent that the aryl group may have include the substituents mentioned in the section of the substituent group A described later.
  • Rtp 5 , Rtp 6 and Rtp 8 each independently represent a substituent.
  • substituents include the substituents mentioned in the section of the substituent group A described later.
  • a linear or branched alkyl group having 1 to 5 carbon atoms, an alkenyl group having 1 to 5 carbon atoms, an aryl group having 6 to 15 carbon atoms, a carboxy group, or a sulfo group is preferable, and a linear chain having 1 to 5 carbon atoms.
  • a branched alkyl group, an alkenyl group having 1 to 5 carbon atoms, a phenyl group, or a carboxy group is more preferable.
  • Rtp 5 and Rtp 6 are preferably each independently an alkyl group having 1 to 5 carbon atoms.
  • Rtp 8 preferably has two alkenyl groups bonded to each other to form a ring.
  • the ring is preferably a benzene ring.
  • a, b and c each independently represent an integer of 0 to 4, and a and b preferably represent 0 or 1, more preferably 0. c preferably represents 0-2.
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group or an aryl group, and are synonymous with Rtp 1 to Rtp 4 in general formula (TP1), and the preferred ranges are also the same. It is.
  • Rtp 5 and Rtp 6 each independently represent a substituent, and are synonymous with Rtp 5 and Rtp 6 in general formula (TP1), and their preferred ranges are also the same.
  • Rtp 9 and Rtp 11 each independently represent a substituent, and the substituents mentioned in the section of Substituent Group A described later can be used.
  • Rtp 9 is preferably an aryl group, more preferably an aryl group having 6 to 12 carbon atoms, and more preferably a phenyl group.
  • Rtp 11 is preferably an alkyl group, more preferably an alkyl group having 1 to 5 carbon atoms, and still more preferably an alkyl group having 1 to 3 carbon atoms.
  • the alkyl group is preferably linear or branched, and more preferably linear.
  • Rtp 10 represents a substituent, and the substituents mentioned in the section of Substituent Group A described later can be used.
  • Rtp 10 is more preferably an aryl group having 6 to 12 carbon atoms, and more preferably a phenyl group.
  • a, b and d each independently represent an integer of 0 to 4, and a and b preferably represent 0 or 1, more preferably 0. d preferably represents 0 to 2, more preferably 0.
  • any one of Rtp 1 to Rtp 11 , Rtp 71 and Rtp 72 represents a binding site to the repeating unit, and in particular, Rtp 71 or Rtp 72 is bonded to the repeating unit. A site is preferred.
  • Rtp 1 to Rtp 11 , Rtp 71 and Rtp 72 may contain an anion.
  • anion —SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , bis (sulfonyl) imide anion, tris (sulfonyl) methide anion and tetraarylborate anion are preferable, and bis (sulfonyl) imide anion and tris (sulfonyl) methide anion And tetraarylborate anions are more preferable, and bis (sulfonyl) imide anions and tris (sulfonyl) methide anions are more preferable.
  • L represents a single bond or a divalent linking group.
  • the divalent linking group preferably represents —NR 10 —, —O—, —SO 2 —, an alkylene group containing a fluorine atom, an arylene group containing a fluorine atom, or a combination thereof.
  • a group consisting of a combination of —NR 10 —, —SO 2 and an alkylene group containing a fluorine atom a group consisting of a combination of —O— and an arylene group containing a fluorine atom, or —NR 10 — and —SO A group consisting of a combination of 2 and an alkylene group containing a fluorine atom is preferred.
  • R 10 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably a hydrogen atom.
  • the number of carbon atoms of the alkylene group containing a fluorine atom is preferably 1 to 10, more preferably 1 to 6, and still more preferably 1 to 3.
  • These alkylene groups are more preferably perfluoroalkylene groups.
  • Specific examples of the fluorine-substituted alkylene group include a difluoromethylene group, a tetrafluoroethylene group, and a hexafluoropropylene group.
  • the number of carbon atoms of the arylene group containing a fluorine atom is preferably 6 to 20, more preferably 6 to 14, and still more preferably 6 to 10.
  • Specific examples of the arylene group containing a fluorine atom include a tetrafluorophenylene group, a hexafluoro-1-naphthylene group, and a hexafluoro-2-naphthylene group.
  • X 1 represents an anion, —SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , a group containing a structure represented by the following general formula (A1), and the following general formula (A2) It is preferable to be selected from at least one selected from a group containing a structure represented by:
  • General formula (A1) In general formula (A1), R 1 and R 2 each independently represents —SO 2 — or —CO—.
  • R 3 represents —SO 2 — or —CO—.
  • R 4 and R 5 each independently represents —SO 2 —, —CO— or —CN.
  • the number of carbon atoms in the fluorine-substituted alkyl group is preferably 1 to 10, more preferably 1 to 6, still more preferably 1 to 3, still more preferably 1 or 2, and particularly preferably 1.
  • These alkyl groups are more preferably perfluoroalkyl groups.
  • a trifluoromethyl group is preferable.
  • the group containing the structure represented by the general formula (A2) preferably has a fluorine-substituted alkyl group at least at any terminal of R 3 to R 5 in the general formula (A2), and R 3 to R 5 More preferably, at least one of the above is directly bonded to the fluorine-substituted alkyl group.
  • at least two ends of R 3 ⁇ R 5, preferably has a fluorine-substituted alkyl group, and more preferably at least two of R 3 ⁇ R 5 are attached directly to a fluorine-substituted alkyl group.
  • a fluorine-substituted alkyl group is synonymous with what was demonstrated by group containing the structure represented by general formula (A1), and its preferable range is also the same.
  • Other specific examples of X 1 include counter anion A described later. In this case, any one hydrogen atom or halogen atom constituting the counter anion A is bonded to L in the general formula (P).
  • the portion substituted with the general formula (P) may be present only at one place, or may be present at two or more places.
  • the polymer TP has a number of cations corresponding to the number of anions in addition to the cations contained in the triarylmethane structure. Is preferred.
  • X represents an anion.
  • X may or may not exist.
  • X when X is present, it means that the anion is outside the molecule of the triarylmethane structure.
  • the term “an anion outside the molecule of the triarylmethane structure” means that the triarylmethane structure and the anion are not bonded via a covalent bond but exist as a separate compound.
  • an anion outside the molecule of the triarylmethane structure is also referred to as a counter anion.
  • Examples of the counter anion include fluorine anion, chlorine anion, bromine anion, iodine anion, cyanide ion, perchlorate anion, borate anion (BF 4 ⁇ etc.), PF 6 ⁇ and SbF 6 ⁇ .
  • the borate anion is a group represented by B (R 10 ) 4 ⁇ , and R 10 is exemplified by a fluorine atom, a cyano group, a fluorinated alkyl group, an alkoxy group, an aryloxy group, and the like.
  • the counter anion may be a compound having an anion portion. That is, the anion part may be included as part of the structure of the compound. In the case where the anion portion is included as a part of the structure of the compound, even if it is included in a part of the polymer having a repeating unit (polymer), it is included in a so-called low molecular compound having a molecular weight of 2000 or less. Also good. In the case of a low molecular weight compound, an embodiment in which at least one of an alkyl group, an aryl group and a crosslinkable group is included together with the anion portion is exemplified. In the present invention, an embodiment in which the counter anion is a compound containing a crosslinkable group and an embodiment in which the counter anion is a polymer containing a repeating unit having an anion moiety are preferred.
  • the counter anion is a compound having an anion moiety
  • the anion moiety is represented by —SO 3 ⁇ , —COO ⁇ , —PO 3 ⁇ , a structure represented by the following general formula (A1), and the following general formula (A2). At least one selected from the structures represented is preferred.
  • the general formula (A1) is more preferably represented by the following general formula (A1-1).
  • Formula (A1-1) (In General Formula (A1-1), R 1 and R 2 each independently represent —SO 2 — or —CO—, and X 1 and X 2 each independently represent an alkylene group or an arylene group. )
  • R 1 and R 2 of the general formula (A1) in the same meaning as R 1 and R 2, and preferred ranges are also the same.
  • X 1 represents an alkylene group
  • the alkylene group preferably has 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • X 1 represents an arylene group
  • the number of carbon atoms in the arylene group is preferably 6 to 18, more preferably 6 to 12, and still more preferably 6.
  • X 1 has a substituent, it is preferably substituted with a fluorine atom.
  • X 2 represents an alkylene group or an arylene group, and an alkylene group is preferable.
  • the alkylene group preferably has 1 to 8 carbon atoms, more preferably 1 to 6, more preferably 1 to 3, and particularly preferably 1.
  • X 2 has a substituent, it is preferably substituted with a fluorine atom.
  • R 3 represents —SO 2 — or —CO—.
  • R 4 and R 5 each independently represents —SO 2 —, —CO— or —CN.
  • Preferably representing the at least two R 3 ⁇ R 5 is -SO 2 - - In formula (A2), at least one of R 3 ⁇ R 5 -SO 2 more preferably represents.
  • the counter anion is a compound having an anion moiety
  • R—SO 3 ⁇ , R—COO — or R—PO 4 — wherein R is substituted with a halogen atom or a halogen atom.
  • alkyl group which may be substituted and an aryl group which may be substituted with a halogen atom are also exemplified.
  • Specific examples of the compound containing the group represented by the general formula (A1) include R 1 as a halogen atom, an alkyl group which may be substituted with a halogen atom, and an aryl which may be substituted with a halogen atom. Examples are compounds bonded to a group.
  • R 4 and R 5 are each substituted with a halogen atom, an alkyl group which may be substituted with a halogen atom, or a halogen atom.
  • a halogen atom an alkyl group which may be substituted with a halogen atom, or a halogen atom.
  • the case where it is the aryl group which may be made is illustrated.
  • the counter anion is a compound having an anion moiety
  • the counter anion is preferably a compound containing a bis (sulfonyl) imide anion, a compound containing a tris (sulfonyl) methide anion, or a compound containing a sulfonate anion.
  • the compound containing a bis (sulfonyl) imide anion may be a monomer or a polymer.
  • the compound containing a bis (sulfonyl) imide anion is preferably represented by the following general formula (AN1).
  • General formula (AN1) In general formula (AN1), R 1 and R 2 each independently represents an alkyl group or an aryl group.
  • R 1 represents an alkyl group or an aryl group.
  • the alkyl group may be linear, branched or cyclic.
  • the alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • the alkyl group is preferably an alkyl group substituted with a fluorine atom.
  • the number of carbon atoms of the alkyl group substituted with a fluorine atom is preferably 1 to 6, and more preferably 1 to 3.
  • the alkyl group may have a substituent. In particular, a perfluoroalkyl group is preferable, and a perfluoromethyl group is more preferable.
  • the aryl group preferably has 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • the aryl group is preferably an aryl group substituted with a fluorine atom.
  • R 2 has the same meaning as R 1 , and the preferred range is also the same.
  • a bis (sulfonyl) imide anion a bis (trifluoromethanesulfonyl) imide anion is preferable. By setting it as such a structure, heat resistance can be improved more.
  • the compound containing a tris (sulfonyl) methide anion is preferably a compound represented by the following general formula (AN2).
  • General formula (AN2) In general formula (AN2), R 3 to R 5 each independently represents an alkyl group or an aryl group. R 3 represents an alkyl group or an aryl group.
  • the alkyl group may be linear, branched or cyclic.
  • the alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • the alkyl group is preferably an alkyl group substituted with a fluorine atom.
  • the number of carbon atoms of the alkyl group substituted with a fluorine atom is preferably 1 to 6, and more preferably 1 to 3.
  • the alkyl group may have a substituent.
  • a perfluoroalkyl group is preferable, and a perfluoromethyl group is more preferable.
  • the aryl group preferably has 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • the aryl group is preferably an aryl group substituted with a fluorine atom.
  • R 4 has the same meaning as R 3 , and the preferred range is also the same.
  • R 5 has the same meaning as R 3 , and the preferred range is also the same.
  • a tris (trifluoromethanesulfonyl) methide anion is preferable.
  • the compound containing a sulfonate anion is preferably represented by the following general formula (AN3).
  • R represents an alkyl group an alkyl group substituted with a fluorine atom is preferred.
  • the alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • a perfluoroalkyl group is preferable, and a perfluoromethyl group is more preferable.
  • R represents an aryl group an aryl group substituted with a fluorine atom is preferred.
  • the aryl group preferably has 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • a trifluoromethanesulfonate anion is preferable.
  • counter anion A Specific examples of other counter anions include the following, but the present invention is not limited thereto. In this specification, the following other specific examples of the counter anion are referred to as “counter anion A”.
  • the counter anion is a compound containing a crosslinkable group
  • the crosslinkable group include known polymerizable groups that can be cross-linked by radicals, acids, and heat. Specifically, a (meth) acryloyl group, a styryl group, a vinyl group, a cyclic ether group, and a group represented by —C—O—R (where R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms).
  • At least one selected from a (meth) acryloyl group, a styryl group, a vinyl group and a cyclic ether group is preferable, and one selected from a (meth) acryloyl group, a styryl group and a vinyl group is more preferable
  • a (meth) acryloyl group or a styryl group is more preferable.
  • the number of crosslinkable groups in the compound containing a crosslinkable group is preferably 1 to 3, and more preferably 1.
  • crosslinkable group and the counter anion may be directly bonded or may be bonded via a linking group, but are preferably bonded via a linking group.
  • a specific example in the case of a compound containing a counter anion crosslinkable group is preferably represented by the following general formula (B).
  • P represents a crosslinkable group.
  • L represents a single bond or a divalent linking group.
  • Anion represents the counter anion.
  • P represents a crosslinkable group, and examples thereof include the crosslinkable groups described above.
  • L represents a divalent linking group
  • an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, —CH ⁇ CH—, —O— , —S—, —C ( ⁇ O) —, —CO—, —NR—, —CONR—, —OC—, —SO 2 — and a combination of two or more thereof are preferred.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • the linking group is preferably a linking group in which two or more alkylene groups having 1 to 10 carbon atoms, arylene groups having 6 to 12 carbon atoms, —NH—, —CO—, —O— and —SO 2 — are combined.
  • a compound containing a counter anion crosslinkable group it may have a functional group other than the crosslinkable group.
  • other functional groups include acid groups.
  • the acid group include a carboxy group, a sulfonic acid group, and a phosphoric acid group.
  • the counter anion further has an acid group, the number of acid groups in the compound is preferably 1 to 3, and more preferably 1.
  • the molecular weight of the compound containing a crosslinkable group is preferably 200 to 2000, and more preferably 200 to 500.
  • the anion multimer may have an anion part in the side chain of the repeating unit, an anion part in the main chain of the repeating unit, or an anion part in both the main chain and the side chain. You may do it.
  • the anion multimer is preferably represented by the following general formula (C) and / or the following general formula (D).
  • X 1 represents the main chain of the repeating unit.
  • L 1 represents a single bond or a divalent linking group.
  • Anion represents the anion moiety.
  • X 1 represents a main chain of repeating units, usually represents a linking group formed by polymerization reaction, for example, (meth) acrylic, styrene, vinyl and the like are preferable.
  • Two sites represented by * are repeating units.
  • L 1 represents a divalent linking group, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, —CH ⁇ CH—, —O—, —S—, — COO—, —CO—, —NR—, —CONR—, —OCO—, —SO 2 — and a linking group obtained by combining two or more thereof are preferred.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • L 1 is a single bond or a combination of 2 or more of an alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms, —NH—, —CO 2 —, —O—, and —SO 2 —.
  • a valent linking group is more preferred.
  • the anion multimer is preferably represented by the following general formula (AN4).
  • General formula (AN4) In the general formula (AN4), X 1 represents a main chain of repeating units. L 1 represents a single bond or a divalent linking group. R 1 represents an alkyl group or an aryl group. X 1 and L 1 have the same meanings as X 1 and L 1 in the above the general formula (C), and preferred ranges are also the same. R 1 represents an alkyl group or an aryl group.
  • the alkyl group may be linear, branched or cyclic.
  • the alkyl group preferably has 1 to 6 carbon atoms, more preferably 1 to 3 carbon atoms.
  • the alkyl group is preferably an alkyl group substituted with a fluorine atom.
  • the number of carbon atoms of the alkyl group substituted with a fluorine atom is preferably 1 to 6, and more preferably 1 to 3.
  • the alkyl group may have a substituent. In particular, a perfluoroalkyl group is preferable, and a perfluoromethyl group is more preferable.
  • the aryl group preferably has 6 to 18 carbon atoms, and more preferably 6 to 12 carbon atoms.
  • the aryl group is preferably an aryl group substituted with a fluorine atom.
  • Formula (D) (In General Formula (D), L 2 and L 3 each independently represent a single bond or a divalent linking group. Anion represents an anion moiety.)
  • L 2 and L 3 represent a divalent linking group, an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 30 carbon atoms, a heterocyclic linking group, —CH ⁇ CH— , —O—, —S—, —CO—, —COO—, —NR—, —CONR—, —OCO—, —SO 2 — and a linking group obtained by combining two or more thereof are preferred.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • L 2 is preferably an arylene group having 6 to 12 carbon atoms (particularly a phenylene group).
  • the arylene group having 6 to 30 carbon atoms is preferably substituted with a fluorine atom.
  • L 3 is preferably a group composed of a combination of an arylene group having 6 to 12 carbon atoms (particularly a phenylene group) and —O—, and at least one arylene group having 6 to 12 carbon atoms is substituted with a fluorine atom. It is preferable.
  • the anionic multimer may contain a repeating unit having a polymerizable group.
  • the amount thereof is preferably, for example, 10 to 50 mol, and more preferably 10 to 30 mol with respect to 100 mol of all repeating units.
  • the anionic multimer may contain a repeating unit having an acid group.
  • the amount thereof is, for example, preferably 10 to 50 mol, more preferably 10 to 30 mol, relative to 100 mol of all repeating units.
  • the weight average molecular weight of the anionic multimer is preferably 1,000 to 30,000, more preferably 3,000 to 20,000.
  • a chain transfer agent When forming an anionic multimer, a chain transfer agent may be added.
  • the chain transfer agent is preferably an alkyl mercaptan, preferably an alkyl mercaptan having 4 or more carbon atoms, an alkyl mercaptan substituted with a carboxy group, an ether group or an ester group.
  • the halogen ion content contained in the anionic multimer is preferably 10 to 3000 ppm, more preferably 10 to 2000 ppm, and even more preferably 10 to 1000 ppm. Specific examples of the anion multimer include the structures described in paragraph numbers 0034 to 0035 of JP-A-2015-030742, the contents of which are incorporated herein.
  • the cation is present in a delocalized manner as follows, and the following structure Are synonymous and both are included in the present invention.
  • the triarylmethane structure is preferably represented by the following general formula (TP3).
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 22 each independently represents an aryl group having 6 to 10 carbon atoms
  • Rtp 71 represents an alkyl group. represents a group or an aryl group
  • X is either an anion, X is at least one contains an anion of Rtp 21, Rtp 22 and Rtp 71 to absent; repeated either Rtp 21, Rtp 22 and Rtp 71 is a unit
  • the binding site to A is represented.
  • Rtp 21 is preferably an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, but is preferably linear.
  • the alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms.
  • Examples of the substituent that the alkyl group may have include the substituents mentioned in the section of Substituent Group A described later. By setting it as such a structure, light resistance can be improved more.
  • Rtp 22 represents an aryl group having 6 to 10 carbon atoms.
  • Rtp 22 is preferably an aryl group having a substituent at least in the ortho position.
  • Rtp 71 represents an alkyl group or an aryl group, and an alkyl group is preferable.
  • the alkyl group may be linear, branched or cyclic, and is preferably cyclic.
  • the alkyl group preferably has 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms.
  • the aryl group preferably has 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms.
  • Any of Rtp 21 , Rtp 22 and Rtp 71 represents a binding site with the repeating unit, and Rtp 71 is preferably a binding site with the repeating unit.
  • the triarylmethane structure is preferably represented by the following general formula (TP3A).
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 22 each independently represents an aryl group having 6 to 10 carbon atoms
  • X represents an anion Or X is absent and at least one of Rtp 21 and Rtp 22 contains an anion
  • * represents the binding site with repeat unit A.
  • the general formula (TP3) have the same meanings as rtp 21, rtp 22 of, and preferred ranges are also the same.
  • Substituent group A Substituents include halogen atoms, alkyl groups, alkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxy groups, nitro groups, alkoxy groups, aryloxy groups, silyloxy groups, heterocyclic oxy groups, acyloxy groups.
  • Carbamoyloxy group amino group (including alkylamino group and anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfamoylamino group, alkyl or arylsulfonylamino group, Mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, alkyl or arylsulfinyl group, alkyl or arylsulfonyl group, acyl group, aryloxycarbonyl group, alkoxycarbonyl group A carbamoyl group, an aryl or heterocyclic azo group, an imido group, a phosphino group, phosphinyl group, phosphinyloxy group, phosphinylamino group, and a silyl group.
  • the repeating unit A is preferably represented by the following general formula (TP3-1).
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 22 each independently represents an aryl group having 6 to 10 carbon atoms
  • Rtp 21 71a represents an alkylene group or an arylene group
  • L 1 represents a divalent linking group having 2 to 30 carbon atoms
  • Rtp 31 represents a hydrogen atom or a methyl group
  • X represents an anion, or X does not exist
  • At least one of Rtp 21 and Rtp 22 contains an anion.
  • Rtp 21 and Rtp 22 are synonymous with Rtp 21 and Rtp 22 in the general formula (TP3) described above, and preferred ranges thereof are also the same.
  • Rtp 71a represents an alkylene group or an arylene group, and an alkylene group is preferable.
  • the alkylene group may be linear, branched or cyclic, and is preferably cyclic.
  • the alkylene group preferably has 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms.
  • the arylene group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms.
  • the alkylene group and the arylene group may have a substituent or may be unsubstituted. Unsubstituted is preferred.
  • L 1 represents a single bond or a divalent linking group.
  • L 1 has the same meaning as L 1 in the general formula (A) described above, and the preferred range is also the same.
  • the atom constituting the chain connecting the main chain of the repeating unit A and the nitrogen atom to which Rtp 71a of the triarylmethane structure is bonded in the “—Rtp 71a -L 1 —” portion, the atom constituting the chain connecting the main chain of the repeating unit A and the nitrogen atom to which Rtp 71a of the triarylmethane structure is bonded.
  • the number is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, and particularly preferably 5 or more.
  • the upper limit is preferably 20 or less, for example.
  • the repeating unit A is preferably represented by the following general formula (TP3-2).
  • Rtp 21 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • Rtp 24 each independently represents an alkyl group having 1 to 4 carbon atoms
  • Rtp 25 Each independently represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms
  • Rtp 71a represents an alkylene group or an arylene group
  • Rtp 31 represents a hydrogen atom or a methyl group
  • L 1 represents a single bond or X represents an anion, or X does not exist and at least one of Rtp 21 and Rtp 24 includes an anion.
  • Rtp 21 is preferably each independently an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group may be linear, branched or cyclic, but is preferably linear.
  • the alkyl group preferably has 1 to 4 carbon atoms, and more preferably 1 to 3 carbon atoms.
  • Rtp 24 is preferably independently an alkyl group having 1 or 2 carbon atoms.
  • Rtp 25 represents an alkyl group having 1 to 3 carbon atoms, the alkyl group preferably has 1 or 2 carbon atoms.
  • Rtp 71a has the same meaning as rtp 71a in general formula (TP3-1), and preferred ranges are also the same.
  • L 1 has the same meaning as L 1 in formula (TP3-1) described above, and the preferred range is also the same.
  • repeating unit A examples include the following structures, but the present invention is not limited to these.
  • Specific examples of the repeating unit A include a repeating unit derived from a monomer having a triarylmethane structure, which will be described later.
  • the polymer TP includes a repeating unit B having a crosslinkable group.
  • the repeating unit B is preferably contained in an amount of 1 to 99% by mass in all the repeating units of the polymer TP.
  • the upper limit is more preferably 95% by mass or less, and still more preferably 90% by mass or less.
  • the lower limit is more preferably 2% by mass or more, and further preferably 3% by mass or more.
  • crosslinkable group a known crosslinkable group that can be crosslinked by a radical, acid, or heat can be used.
  • a group containing an ethylenically unsaturated bond a cyclic ether group (epoxy group, oxetanyl group), an oxazoline group , A group represented by —C—O—R (wherein R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), a carbonate group, and the like.
  • R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms
  • carbonate group and the like.
  • examples of the group containing an ethylenically unsaturated bond include a (meth) acryloyl group, a vinyl group, and a dicyclopentenyl group.
  • the crosslinkable group includes an epoxy group, an oxetanyl group, an oxazoline group, a group represented by —C—O—R (where R represents a hydrogen atom or an alkyl group having 1 to 20 carbon atoms), a carbonate group, ) At least one selected from an acryloyl group and a vinyl group is preferable, and an epoxy group or an oxetanyl group is more preferable.
  • the crosslinkable group possessed by the polymer TP reacts with the crosslinkable groups possessed by the polymer TP, or reacts with the crosslinkable groups possessed by an alkali-soluble binder or a crosslinking agent.
  • repeating unit B examples include the following specific examples. However, the present invention is not limited to these.
  • the polymer TP may further have a repeating unit other than the above repeating units A and B.
  • other repeating units include repeating units derived from at least one of (meth) acrylic acid, (meth) acrylic acid ester, and (meth) acrylic acid amide.
  • Specific examples include a repeating unit having an acid group.
  • the acid group include a carboxy group, a sulfonic acid group, and a phosphoric acid group, and a carboxy group is preferable.
  • the ratio of the repeating unit containing the repeating unit having an acid group may be, for example, 10 to 80% by mass in all the repeating units of the polymer TP. Preferably, 10 to 60% by mass is more preferable.
  • repeating units include lactones, acid anhydrides, amides, —COCH 2 CO—, development promoting groups such as cyano groups, long chain and cyclic alkyl groups, aralkyl groups, aryl groups, polyalkylene oxide groups, hydroxy groups, maleimides It may have a functional group such as a hydrophilicity adjusting group such as a group or an amino group.
  • the polymer TP preferably has a structure containing a repeating unit derived from at least one of (meth) acrylic acid, (meth) acrylic acid ester, and (meth) acrylic acid amide.
  • the above-described repeating unit A and / or repeating unit B is a repeating unit derived from at least one of (meth) acrylic acid, (meth) acrylic acid ester and (meth) acrylic amide
  • the aspect whose repeating unit is a repeating unit derived from at least 1 sort (s) of (meth) acrylic acid, (meth) acrylic acid ester, and (meth) acrylic acid amide is mentioned.
  • the weight average molecular weight of the polymer TP is preferably 3000 to 500,000.
  • the lower limit is preferably 4000 or more, more preferably 5000 or more, still more preferably 7000 or more, and particularly preferably 10,000 or more.
  • the upper limit is preferably 200000 or less, more preferably 100000 or less, and particularly preferably 50000 or less. That is, the weight average molecular weight of the polymer TP is particularly preferably 10,000 to 50,000.
  • Heat resistance and solvent resistance are good by adjusting the weight average molecular weight of the polymer TP to the above-described range. Furthermore, the voltage characteristics can be improved.
  • the number average molecular weight of the polymer TP is preferably 2,000 to 500,000.
  • the lower limit is preferably 2500 or more, more preferably 3000 or more, still more preferably 4000 or more, and particularly preferably 5000 or more.
  • the upper limit is preferably 100,000 or less, more preferably 70000 or less, and particularly preferably 50000 or less.
  • the dispersity (weight average molecular weight / number average molecular weight) of the polymer TP is preferably 1.0 to 5.0.
  • the upper limit is preferably 4.0 or less, more preferably 3.5 or less, and particularly preferably 2.0 or less.
  • the weight average molecular weight and number average molecular weight of the polymer TP are polystyrene-converted values in gel permeation chromatograph (GPC) measurement, and specifically are values measured by the method described in the examples described later.
  • the content of the compound A having a triarylmethane structure and a weight average molecular weight of 1500 or less is 20% by mass or less, preferably 10% by mass or less, preferably 5% by mass with respect to the mass of the polymer TP. % Or less is more preferable, 1% by mass or less is particularly preferable, and it can be substantially not contained.
  • substantially not containing means that, for example, the content of compound A is preferably 0.1% by mass or less, more preferably 0.01% by mass or less, and not more than 0.1% by mass with respect to the mass of the polymer TP. preferable.
  • Compound A is a compound having a triarylmethane structure, and specifically means an unreacted material such as a raw material monomer having a triarylmethane structure, or a raw material monomer-containing impurity having no polymerizable group. To do.
  • the content of Compound A in the polymer TP can be measured by detecting with ultraviolet light in the GPC measurement of the polymer TP.
  • the content of Compound A in the polymer TP is 2 for TSKgel ⁇ -M (Tosoh Corp., 7.8 mm (inner diameter) ⁇ 30 cm) using HLC-8020GPC (Tosoh Corp.).
  • the column is connected in series, and the measurement conditions are N-methyl-2-pyrrolidone (NMP) solution with a sample concentration of 0.35% by mass, a flow rate of 0.3 mL / min, and a sample injection amount of 10 ⁇ L. It is a value obtained by setting the temperature to 40 ° C. and using an ultraviolet detector.
  • NMP N-methyl-2-pyrrolidone
  • the polymer TP is preferably a polymer containing a repeating unit represented by the general formula (TP-7).
  • each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • R 4 represents a hydrogen atom or a methyl group
  • R 1a represents an alkylene group or an arylene group.
  • L 11 represents a single bond or a divalent linking group having 1 to 30 carbon atoms
  • L 12 and L 13 represent a single bond or a divalent linking group having 1 to 30 carbon atoms.
  • R 2 represents a hydrocarbon group having 1 to 10 carbon atoms
  • R 3 represents a crosslinkable group
  • X represents a compound containing a bis (sulfonyl) imide anion, a tris (sulfonyl) methide anion or a sulfonate anion
  • a to d are mass ratios of repeating units, a and d each represent a number exceeding 0, and b and c each independently represent a number of 0 or more.
  • each R 1 independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms, preferably an alkyl group having 1 to 6 carbon atoms.
  • the alkyl group preferably has 1 to 3 carbon atoms.
  • the alkyl group is preferably linear.
  • R 2 represents a hydrocarbon group having 1 to 10 carbon atoms.
  • the hydrocarbon group may be linear, branched or cyclic, and is preferably linear or cyclic.
  • the hydrocarbon group is preferably an aliphatic hydrocarbon group, and is preferably an alkyl group.
  • R 2 is preferably a cyclic alkyl group having 5 to 10 carbon atoms, a linear alkyl group having 1 to 8 carbon atoms, or a branched alkyl group having 3 to 8 carbon atoms.
  • the number of carbon atoms in the cyclic alkyl group is preferably 6 to 8, and more preferably 6.
  • the linear alkyl group preferably has 1 or 2 carbon atoms, more preferably 1.
  • the branched alkyl group preferably has 3 to 8 carbon atoms.
  • the hydrocarbon group may have a substituent, and the substituent is preferably a hydroxy group. As an example of the case where the hydrocarbon group has a substituent, a hydroxyethyl group is preferable.
  • R 3 represents a crosslinkable group.
  • the crosslinkable group includes an ethylenically unsaturated bond-containing group, an epoxy group, an oxetanyl group, an oxazoline group, and a group represented by —C—O—R (where R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms). And at least one selected from carbonate groups.
  • R is a hydrogen atom or an alkyl group having 1 to 20 carbon atoms.
  • the group containing an ethylenically unsaturated bond include a (meth) acryloyl group, a vinyl group, and a dicyclopentenyl group.
  • R 4 represents a hydrogen atom or a methyl group, and is preferably a methyl group.
  • R 1a represents an alkylene group or an arylene group, and an alkylene group is preferred.
  • the alkylene group may be linear, branched or cyclic, and is preferably cyclic.
  • the alkylene group preferably has 1 to 8 carbon atoms, more preferably 1 to 6 carbon atoms.
  • the arylene group preferably has 6 to 12 carbon atoms, and more preferably 6 to 10 carbon atoms.
  • the alkylene group and the arylene group may have a substituent or may be unsubstituted. Unsubstituted is preferred. Examples of the substituent include the substituents described in the substituent group A described above.
  • L 11 represents a single bond or a divalent linking group having 1 to 30 carbon atoms.
  • the divalent linking group is selected from an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 12 carbon atoms, and —CO—, —OCO—, —O—, —NH— and —SO 2 —. Group which combines 1 type is mentioned.
  • the divalent linking group is preferably an alkylene group, an alkylene group, or a linking group in which the alkylene groups are linked via one or more selected from —O—, —COO—, and —OCO—.
  • L 12 and L 13 each represent a single bond or a divalent linking group having 1 to 30 carbon atoms.
  • the divalent linking group is selected from an alkylene group having 1 to 30 carbon atoms, an arylene group having 6 to 12 carbon atoms, and —CO—, —OCO—, —O—, —NH— and —SO 2 —.
  • Group which combines 1 type is mentioned.
  • the alkylene group and the arylene group may have a substituent or may be unsubstituted. Examples of the substituent include the substituent group A described above. Of these, a hydroxy group is preferred.
  • the “—L 11 —R 1a —” moiety the atoms constituting the chain connecting the main chain of the repeating unit A and the nitrogen atom to which R 1a of the triarylmethane structure is bonded.
  • the number is preferably 1 or more, more preferably 2 or more, still more preferably 3 or more, and particularly preferably 5 or more.
  • the upper limit is preferably 20 or less, for example.
  • X represents a compound containing a bis (sulfonyl) imide anion, a tris (sulfonyl) methide anion or a sulfonate anion, and a compound containing a bis (sulfonyl) imide anion is preferred.
  • the compound containing a bis (sulfonyl) imide anion may be a monomer or a multimer.
  • the compound containing a bis (sulfonyl) imide anion is preferably a compound represented by the general formula (AN1) described above.
  • the compound containing a tris (sulfonyl) methide anion is preferably a compound represented by the general formula (AN2) described above.
  • the compound containing a sulfonate anion is preferably a compound represented by the general formula (AN3) described above.
  • a to d are mass ratios of repeating units, a and d represent a number exceeding 0, and b and c each independently represent a number of 0 or more.
  • a is preferably 0.01 to 0.99.
  • b represents an integer of 0 or more, and preferably 0 to 90.
  • c represents an integer of 0 or more, preferably 0 to 90.
  • d is preferably from 0.01 to 0.99.
  • polymer TP Although the specific example of polymer TP is shown to this invention below, it is not limited to these.
  • the polymer TP of the present invention comprises a triarylmethane monomer having a triarylmethane structure represented by at least one selected from general formula (TP1a) and general formula (TP2a), and a monomer having a crosslinkable group. It can be produced by polymerizing at least raw material monomers.
  • the raw material monomer may further include a monomer having an acid group and a monomer having a functional group described in the above-described other repeating unit.
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group or an aryl group
  • Rtp 5 , Rtp 6 , Rtp 8 , Rtp 9 and Rtp 11 are each Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group or NRtp 71 Rtp 72
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group or an aryl group
  • Rtp 10 represents a hydrogen atom, an alkyl group or an aryl group
  • a, b, c and d each independently represent an integer of 0 to 4; when a, b, c and d are 2 or more, Rtp 5, Rtp 6, two of Rtp 8 and Rtp 9 are each, linked may form a ring; or
  • X is an anion, Rtp 1 ⁇ Rtp 11 without X is
  • Rtp 1 ⁇ Rtp 11, Rtp 71 , Rtp 72 and X in general formula (TP1a), and, rtp 1 ⁇ rtp 11 of the general formula (TP2a), rtp 71, have the same meanings as rtp 72 and X, the preferred range is also It is the same.
  • at least one of Rtp 1 to Rtp 11 , Rtp 71 and Rtp 72 has a polymerizable group. It is preferable that at least one of Rtp 71 and Rtp 72 has a polymerizable group.
  • the polymerizable group include a vinyl group, a (meth) acryloyl group, and a styryl group, and a (meth) acryloyl group is preferable.
  • the polymerization temperature is preferably 40 to 90 ° C, more preferably 50 to 70 ° C.
  • the polymerization is preferably performed in a solution containing the above-mentioned raw material monomers in a total amount of 30 to 60% by mass.
  • the content of the raw material monomer in the solution is more preferably 35 to 55% by mass, still more preferably 40 to 55% by mass. If content of a raw material monomer is the said range, it can make it easy to advance superposition
  • the solvent used in the preparation of the raw material monomer reaction solution include solvents that may be contained in the coloring composition described below.
  • a chain transfer agent may be added during the polymerization.
  • an alkyl mercaptan is preferable, and an alkyl mercaptan having 4 or more carbon atoms or an alkyl mercaptan substituted with a carboxy group, an ether group or an ester group is preferable.
  • dodecyl mercaptan and dipentaerythritol hexa-3-mercaptopropionate are preferable from the viewpoint of odor, and thiomalic acid and mercaptopropionic acid are preferable from the viewpoint of promoting developability.
  • a purification treatment may be performed. Thereby, content of the compound A can be reduced.
  • the content of the polymer TP is preferably 10 to 60% by mass and more preferably 10 to 40% by mass with respect to the total solid content of the colored composition of the present invention.
  • the coloring composition of the present invention may contain one or more coloring compounds other than the above-described polymer TP.
  • coloring compounds include dye compounds, pigment compounds, and dispersions thereof.
  • the pigment compound When the pigment compound is blended as a dispersion, it can be prepared according to the descriptions in JP-A-9-197118 and JP-A-2000-239544.
  • the dye compound examples include azo compounds (for example, Solvent Yellow 162), anthraquinone compounds (for example, anthraquinone compounds described in JP-A-2001-10881), and phthalocyanine compounds (for example, phthalocyanine described in US 2008 / 0076044A1).
  • Compound xanthene series (for example, C.I. Acid Red Red 289), triarylmethane series (for example, C.I. Acid Blue 7)
  • C.I. Acid Blue 83 CI Acid Blue 83
  • C.I. Acid Blue 90 C.I. Acid Blue 90
  • C.I. Solvent Blue 38 C.I.
  • Solvent Blue 38 Sea I A Violet 17 (CI Acid Violet 17), CI Acid violet 49 (CI Acid violet 49), CI Acid Green 3), methine And dyes, xanthene dyes (for example, JP 2010-32999 A), dipyrromethene metal complex compounds (for example, JP 2012-237985 A), and the like.
  • pigment compounds include perylene, perinone, quinacridone, quinacridonequinone, anthraquinone, anthanthrone, benzimidazolone, disazo condensation, disazo, azo, indanthrone, phthalocyanine, triarylcarbonium, dioxazine, aminoanthraquinone, diketopyrrolopyrrole, Indigo, thioindigo, isoindoline, isoindolinone, pyranthrone, isoviolanthrone and the like.
  • perylene compound pigments such as Pigment Red 190, Pigment Red 224, and Pigment Violet 29, perinone compound pigments such as Pigment Orange 43, and Pigment Red 194, Pigment Violet 19, and Pigment Violet. 42, quinacridone such as Pigment Red 122, Pigment Red 192, Pigment Red 202, Pigment Red 207, or Pigment Red 209, quinacridone compound pigment, Pigment Red 206, Pigment Orange 48, or Pigment Orange 49 Quinone compound pigment, anthraquinone compound pigment such as pigment yellow 147, anthanthrone compound pigment such as pigment red 168, pigment Benzimidazolone compound pigments such as Pigment Brown 25, Pigment Violet 32, Pigment Orange 36, Pigment Yellow 120, Pigment Yellow 180, Pigment Yellow 181, Pigment Orange 62, or Pigment Red 185; Yellow 93, Pigment Yellow 94, Pigment Yellow 95, Pigment Yellow 128, Pigment Yellow 166, Pigment Orange 34, Pigment Orange 13, Pigment Orange 31, Pigment Red 144
  • a color material of green to cyan is preferable, such as Pigment Green 7, Pigment Green 36, Pigment Green 37, Pigment Green 58, Pigment Blue 16, Pigment Blue 75, or Pigment Blue 15.
  • Phthalocyanine compound pigments triarylcarbonium compound pigments such as pigment blue 56 or pigment blue 61, dioxazine compound pigments such as pigment violet 23 or pigment violet 37, aminoanthraquinone compound pigments such as pigment red 177, Pigment Red 254, Pigment Red 255, Pigment Red 264, Pigment Red 272, Pigment Orange 71, Pigment Orange 73, etc.
  • Ketopyrrolopyrrole compound pigments thioindigo compound pigments such as Pigment Red 88, isoindolin compound pigments such as Pigment Yellow 139 and Pigment Orange 66, isoindolinone compound pigments such as Pigment Yellow 109 or Pigment Orange 61, Pyranthrone compound pigments such as CI Pigment Orange 40 or CI Pigment Red 216, or isoviolanthrone compound pigments such as CI Pigment Violet 31 are preferred.
  • the other colored compound preferably includes at least one selected from a xanthene compound, a dipyrromethene metal complex compound, an oxazine compound, and a phthalocyanine compound, and includes at least one selected from a xanthene compound and a dipyrromethene metal complex compound. More preferably.
  • the xanthene compound is a compound having a xanthene skeleton in the molecule.
  • CI Color Index
  • Acid Red 51 hereinafter, description of CI Acid Red is omitted, and only the number is described. Others are also the same
  • CI Color Index
  • the xanthene compound preferably contains a compound represented by the general formula (1a) (hereinafter sometimes referred to as “compound (1a)”).
  • Compound (1a) may be a tautomer thereof.
  • the content of the compound (1a) in the xanthene compound is preferably 50% by mass or more, more preferably 70% by mass or more, and further preferably 90% by mass or more. In particular, it is preferable to use only the compound (1a) as the xanthene compound.
  • R 1 to R 4 each independently have a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms which may have a substituent, or a substituent. Represents a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, and —CH 2 — contained in the saturated hydrocarbon group is substituted with —O—, —CO— or —NR 11 —.
  • R 1 and R 2 may be bonded to each other to form a ring containing a nitrogen atom, and R 3 and R 4 may be bonded to each other to form a ring containing a nitrogen atom;
  • R 5 is, -OH, -SO 3 -, -SO 3 H, -SO 3 - Z +, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -SO 3 R 8 or -SO 2 represents NR 9 R 10 ;
  • R 6 and R 7 each independently represents an alkyl group having 1 to 6 carbon atoms;
  • m1 represents an integer of 0 to 5.
  • the plurality of R 5 may be the same or different; m2 and m3 each independently represents an integer of 0 to 3. when m2 and m3 are each independently 2 or 3, a plurality of R 6 and R 7 may be independently the same or different; a represents 0 or 1; when a represents 0, any group of R 1 to R 7 has an anion; X ⁇ represents an anion; Z + represents N + (R 11 ) 4 , Na + or K + , and four R 11 may be the same or different; R 8 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group may be substituted with a halogen atom; R 9 and R 10 each independently represents a hydrogen atom or a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, and —CH 2 — contained in the saturated aliphatic hydrocarbon group is —O—, It may be substituted with —CO—, —NH— or —
  • Examples of the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R 1 to R 4 include a phenyl group, a toluyl group, a xylyl group, a mesityl group, a propylphenyl group, and a butylphenyl group.
  • a toluyl group, a xylyl group, a mesityl group, and a propylphenyl group are preferable, and a toluyl group and a xylyl group are particularly preferable, and among these, a 2,6-disubstituted xylyl group is preferable.
  • the aromatic hydrocarbon group substituent which may have a halogen atom, -R 8, -OH, -OR 8 , -SO 3 -, - SO 3 H, -SO 3 - Z +, -CO 2 H, —CO 2 R 8 , —SR 8 , —SO 2 R 8 , —SO 3 R 8 or —SO 2 NR 9 R 10 may be mentioned.
  • substituent -SO 3 -, - SO 3 H, -SO 3 - Z + and -SO 2 NR 9 R 10 is preferably, -SO 3 - Z + and -SO 2 NR 9 R 10 Is more preferable.
  • the Z +, -SO 3 - - - SO 3 in this case N + (R 11) 4 are preferred.
  • Examples of the ring formed by combining R 1 and R 2 with each other and the ring formed by combining R 3 and R 4 with each other include the following. Among these, the following structures are preferable from the viewpoint of compound stability.
  • Examples of the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 8 to R 11 include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a nonyl group.
  • Linear alkyl groups such as decyl group, dodecyl group, hexadecyl group, icosyl group; branched alkyl groups such as isopropyl group, isobutyl group, isopentyl group, neopentyl group, 2-ethylhexyl group; cyclopropyl group, cyclopentyl group And alicyclic saturated hydrocarbon groups having 3 to 20 carbon atoms such as cyclohexyl group, cycloheptyl group, cyclooctyl group and tricyclodecyl group.
  • a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, and a 2-ethylhexyl group are preferable, and a propyl group, an isopropyl group, a butyl group, a hexyl group, A 2-ethylhexyl group is preferred.
  • the hydrogen atom contained in the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms may be substituted with, for example, an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom.
  • Examples of —OR 8 include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, and an icosyloxy group.
  • a methoxy group, an ethoxy group, a propoxy group, and a butoxy group are preferable.
  • Examples of —CO 2 R 8 include a methoxycarbonyl group, an ethoxycarbonyl group, a propoxycarbonyl group, a tert-butoxycarbonyl group, a hexyloxycarbonyl group, and an icosyloxycarbonyl group. Of these, a methoxycarbonyl group, an ethoxycarbonyl group, and a propoxycarbonyl group are preferable.
  • Examples of —SR 8 include a methylsulfanyl group, an ethylsulfanyl group, a butylsulfanyl group, a hexylsulfanyl group, a decylsulfanyl group, and an icosylsulfanyl group.
  • Examples of —SO 2 R 8 include a methylsulfonyl group, an ethylsulfonyl group, a butylsulfonyl group, a hexylsulfonyl group, a decylsulfonyl group, and an icosylsulfonyl group.
  • Examples of —SO 3 R 8 include a methoxysulfonyl group, an ethoxysulfonyl group, a propoxysulfonyl group, a tert-butoxysulfonyl group, a hexyloxysulfonyl group, and an icosyloxysulfonyl group.
  • —SO 2 NR 9 R 10 includes, for example, a sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-isobutylsulfamoyl group, N- sec-butylsulfamoyl group, N-tert-butylsulfamoyl group, N-pentylsulfamoyl group, N- (1-ethylpropyl) sulfamoyl group, N- (1,1-dimethylpropyl) sulfamoyl group, N- (1,2-dimethylpropyl) sulfamoyl group, N- (2-ethylhexyl) sulfamoyl group, N- (2
  • N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-isopropylsulfamoyl group, N-butylsulfamoyl group, N-pentylsulfamoyl group, N -(2-ethylhexyl) sulfamoyl group is preferred, N-methylsulfamoyl group, N-ethylsulfamoyl group, N-propylsulfamoyl group, N-butylsulfamoyl group, N- (2-ethylhexyl) A sulfamoyl group is more preferred.
  • the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 9 and R 10 may have a substituent, and examples of the substituent include a hydroxy group and a halogen atom.
  • R 5 is, -CO 2 H, -CO 2 - Z +, -CO 2 R 8, -CO 2 NHR 9, -SO 3 -, -SO 3 - Z +, -SO 3 H, -SO 2 R 8 or -SO 2 NHR 9 is preferably,, -SO 3 -, -SO 3 - Z +, -SO 3 H or -SO 2 NHR 9 is more preferable.
  • m1 is preferably an integer of 1 to 4, and more preferably 1 or 2.
  • R 6 and R 7 each independently represents an alkyl group having 1 to 6 carbon atoms.
  • m2 and m3 each independently represents an integer of 0 to 3, with 0 being preferred.
  • Examples of the aralkyl group having 7 to 10 carbon atoms in R 11 include a benzyl group, a phenylethyl group, and a phenylbutyl group.
  • a represents 0 or 1
  • R 1 to R 7 preferably has an anion
  • R 5 preferably has an anion.
  • X ⁇ is included depending on the valence of the cation contained in the general formula (1a), and is usually monovalent or divalent, and monovalent is preferable.
  • the anion X ⁇ include a fluorine anion, a chlorine anion, a bromine anion, an iodine anion, a cyanide ion, a perchlorate anion, and a low nucleophilic anion.
  • a fluorine anion, a chlorine anion, a bromine anion or an iodine anion is preferable. .
  • the low nucleophilic anion indicates an anion structure in which an organic acid having a pKa lower than that of sulfuric acid is dissociated.
  • anions include low nucleophilic anions described in paragraph No. 0075 of JP2007-310315, anions described in paragraphs 0016 to 0025 of JP2012-173399, and JP2013-037316A.
  • Examples include the anion moiety described in paragraphs 0025 to 0033, the contents of which are incorporated herein.
  • Z + is N + (R 11 ) 4 , Na + or K + , preferably N + (R 11 ) 4 .
  • N + (R 11 ) 4 is preferably a monovalent saturated hydrocarbon group having 5 to 20 carbon atoms, at least two of the four R 11 . Further, the total carbon number of the four R 11 is preferably 20 to 80, and more preferably 20 to 60.
  • the compound (1a) is preferably a compound represented by the general formula (3a) (hereinafter sometimes referred to as “compound (3a)”).
  • Compound (3a) may be a tautomer thereof.
  • R 31 and R 32 each independently represents a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms.
  • the hydrogen atom contained in the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms may be substituted with an aromatic hydrocarbon group having 6 to 10 carbon atoms or a halogen atom.
  • a hydrogen atom contained in an aromatic hydrocarbon group having 6 to 10 carbon atoms may be substituted with an alkoxy group having 1 to 3 carbon atoms, and is contained in a monovalent saturated hydrocarbon group having 1 to 10 carbon atoms.
  • —CH 2 — may be substituted with —O—, —CO— or —NR 11 —.
  • R 33 and R 34 each independently represents an alkyl group having 1 to 4 carbon atoms, an alkylsulfanyl group having 1 to 4 carbon atoms, or an alkylsulfonyl group having 1 to 4 carbon atoms.
  • R 31 and R 33 may be bonded to each other to form a ring containing a nitrogen atom
  • R 32 and R 34 may be bonded to each other to form a ring containing a nitrogen atom.
  • p and q each independently represents an integer of 0 to 5. When p is 2 or more, the plurality of R 33 may be the same or different. When q is 2 or more, the plurality of R 34 may be the same or different.
  • R 11 has the same meaning as R 11 in the general formula (1a).
  • Examples of the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms in R 31 and R 32 include carbon among the monovalent saturated hydrocarbon groups having 1 to 10 carbon atoms described for R 8 in the general formula (1a). Examples thereof include monovalent saturated hydrocarbon groups of several 1 to 10. Of these, methyl, ethyl, propyl, butyl, hexyl and 2-ethylhexyl are preferred. Examples of the aromatic hydrocarbon group having 6 to 10 carbon atoms which may be present as a substituent include the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms described for R 1 in the general formula (1a). Can be mentioned.
  • alkoxy group having 1 to 3 carbon atoms in which the hydrogen atom contained in the aromatic hydrocarbon group having 6 to 10 carbon atoms may be substituted include a methoxy group, an ethoxy group, and a propoxy group.
  • R 31 and R 32 are preferably each independently a monovalent saturated hydrocarbon group having 1 to 3 carbon atoms.
  • Examples of the alkyl group having 1 to 4 carbon atoms in R 33 and R 34 include a methyl group, an ethyl group, a propyl group, a butyl group, an isopropyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group. Of these, a methyl group, an ethyl group, and a propyl group are preferable.
  • Examples of the alkylsulfonyl group having 1 to 4 carbon atoms for R 33 and R 34 include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and an isopropylsulfonyl group.
  • P and q are preferably integers of 0 to 2, preferably 0 or 1.
  • the compound (1a) include compounds represented by the formulas (1-1) to (1-43) described in paragraph numbers 0039 to 0046 of JP-A-2014-005451. Are incorporated herein.
  • xanthene compound a commercially available xanthene dye (for example, “Chugai Aminol Fast Pink RH / C” manufactured by Chugai Kasei Co., Ltd., “Rhodamin 6G” manufactured by Taoka Chemical Industry Co., Ltd.) can be used. .
  • a commercially available xanthene dye can be used as a starting material and synthesized with reference to Japanese Patent Application Laid-Open No. 2010-32999, the contents of which are incorporated herein.
  • dipyrromethene-based metal complex compound examples include compounds in which the compound represented by the general formula (I) is coordinated to a metal atom or a metal compound.
  • R 1 to R 6 each independently represents a hydrogen atom or a substituent
  • R 7 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • substituents examples include the above-described substituent group A.
  • substituent group A When the substituent is a group that can be further substituted, it may be further substituted with any of the above-described substituents. In addition, when it has two or more substituents, those substituents may be the same or different.
  • R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6 are each independently bonded to each other to form 5-membered, 6-membered or 7-membered
  • a ring may be formed.
  • the ring formed include a saturated ring and an unsaturated ring.
  • Examples of the 5-membered, 6-membered or 7-membered saturated ring or unsaturated ring include a pyrrole ring, furan ring, thiophene ring, pyrazole ring, imidazole ring, triazole ring, oxazole ring, thiazole ring, pyrrolidine ring, Examples include a piperidine ring, a cyclopentene ring, a cyclohexene ring, a benzene ring, a pyridine ring, a pyrazine ring and a pyridazine ring, and preferably a benzene ring and a pyridine ring.
  • the formed 5-membered, 6-membered and 7-membered rings are further substitutable groups, they may be substituted with any of the above-mentioned substituent group A, and two or more substituents may be substituted. When substituted with a group, the substituents may be the same or different.
  • R 1 and R 6 are preferably an alkylamino group, an arylamino group, a carbonamido group, a ureido group, an imide group, an alkoxycarbonylamino group, a sulfonamido group, a carbonamido group, a ureido group, An alkoxycarbonylamino group and a sulfonamide group are more preferable, a carbonamide group, a ureido group, an alkoxycarbonylamino group, and a sulfonamide group are more preferable, and a carbonamide group and a ureido group are particularly preferable.
  • R 2 and R 5 are preferably an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, an alkylsulfonyl group, an arylsulfonyl group, a nitrile group, an imide group, a carbamoylsulfonyl group, an alkoxycarbonyl group, Aryloxycarbonyl group, carbamoyl group, alkylsulfonyl group, nitrile group, imide group, carbamoylsulfonyl group are more preferable, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, nitrile group, imide group, carbamoylsulfonyl group are more preferable, An alkoxycarbonyl group, an aryloxycarbonyl group, and a carbamoyl group are particularly preferable.
  • R 3 and R 4 are preferably an alkoxycarbonyl group, an
  • the alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 12 carbon atoms, for example, methyl group, ethyl Group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, i-butyl group, tert-butyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, and benzyl group.
  • a branched or cyclic alkyl group having 1 to 12 carbon atoms is preferred, and examples thereof include isopropyl group, cyclopropyl group, i-butyl group, tert-butyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
  • a secondary or tertiary alkyl group having 1 to 12 carbon atoms is more preferable, and examples thereof include an isopropyl group, a cyclopropyl group, an i-butyl group, a tert-butyl group, a cyclobutyl group, and a cyclohexyl group.
  • the aryl group is preferably a phenyl group or a naphthyl group, and more preferably a phenyl group.
  • the heterocyclic group includes a 2-thienyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-furyl group, 2-pyrimidinyl group, 2 A benzothiazolyl group, a 1-imidazolyl group, a 1-pyrazolyl group or a benzotriazol-1-yl group, more preferably a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, a 2-pyrimidinyl group or a 1-pyridyl group preferable.
  • the metal or metal compound may be any metal atom or metal compound capable of forming a complex, a divalent metal atom, a divalent metal oxide, a divalent metal hydroxide, or 2 Valent metal chlorides are included.
  • a preferred embodiment of the dipyrromethene-based metal complex compound in which the compound represented by the general formula (I) is coordinated to a metal atom or a metal compound is described in paragraphs 0153 to 0176 of JP2012-237985A.
  • the complex compounds represented by 1), (I-2) or (I-3) can be taken into account, the contents of which are incorporated herein.
  • the description in paragraphs 0179 to 0186 of JP2012-237985A can be referred to, the contents of which are incorporated herein.
  • the coloring composition of the present invention contains other coloring compounds, it is preferably 0.5 to 70% by mass with respect to the total solid content of the coloring composition of the present invention. Further, it is preferably added to the coloring composition so that the absorption intensity ratio (absorption at 450 nm / absorption at 650 nm) is in the range of 0.95 to 1.05.
  • the coloring composition of the present invention contains a polymerizable compound.
  • the polymerizable compound include addition polymerizable compounds having at least one ethylenically unsaturated double bond.
  • ⁇ is selected from compounds having at least one terminal ethylenically unsaturated bond, preferably two or more.
  • Such compound groups are widely known in this industrial field, and in the present invention, these compounds can be used without any particular limitation. These may be in any chemical form such as, for example, monomers, prepolymers, i.e. dimers, trimers and oligomers, or mixtures thereof and their (co) polymers. Monomers are preferred.
  • Examples of monomers and their (co) polymers include unsaturated carboxylic acids (for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.), their esters, amides, and these (Co) polymers, preferably esters of unsaturated carboxylic acids and aliphatic polyhydric alcohol compounds, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and these (co) polymers It is a polymer.
  • unsaturated carboxylic acids for example, acrylic acid, methacrylic acid, itaconic acid, crotonic acid, isocrotonic acid, maleic acid, etc.
  • esters amides
  • these (Co) polymers preferably esters of unsaturated carboxylic acids and aliphatic polyhydric alcohol compounds, amides of unsaturated carboxylic acids and aliphatic polyhydric amine compounds, and these (co) polymers It is a polymer
  • reaction products of monofunctional or polyfunctional isocyanates or epoxies with unsaturated carboxylic acid esters or amides having a nucleophilic substituent such as hydroxy group, amino group, mercapto group, monofunctional or polyfunctional are also preferably used.
  • an addition reaction product of an unsaturated carboxylic acid ester or amide having an electrophilic substituent such as an isocyanate group or an epoxy group with a monofunctional or polyfunctional alcohol, amine, or thiol, and a halogen group A substitution reaction product of an unsaturated carboxylic acid ester or amide having a detachable substituent such as a tosyloxy group and a monofunctional or polyfunctional alcohol, amine or thiol is also suitable.
  • paragraph numbers 0156 to 0159 of JP-A-2014-208808 can be referred to, and the contents thereof are incorporated in the present specification.
  • dipentaerythritol triacrylate (KAYARAD D-330 as a commercial product; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol tetraacrylate (as a commercial product, KAYARAD D-320; Nippon Kayaku Co., Ltd.) Company-made) dipentaerythritol penta (meth) acrylate (as a commercial product, KAYARAD D-310; manufactured by Nippon Kayaku Co., Ltd.), dipentaerythritol hexa (meth) acrylate (as a commercial product, KAYARAD DPHA; Nippon Kayaku Co., Ltd.) And a structure in which these (meth) acryloyl groups are bonded via an ethylene glycol or propylene glycol residue.
  • These oligomer types can also be used.
  • the structure, details of usage such as single use or combination, addition amount and the like can be arbitrarily set according to the final performance design of the coloring composition.
  • a structure having a high unsaturated group content per molecule is preferable, and in many cases, a bifunctional or higher functionality is preferable.
  • those having three or more functionalities are preferable, and those having different functional numbers and different polymerizable groups (for example, acrylic acid ester, methacrylic acid ester, styrene compound, vinyl ether compound) are used in combination.
  • a method of adjusting both sensitivity and intensity is also effective.
  • compatibility may be improved by the use of a low-purity compound or a combination of two or more.
  • a specific structure may be selected from the viewpoint of improving adhesion to a hard surface such as a substrate.
  • the content of the polymerizable compound in the total solid content of the coloring composition is preferably 10 to 80% by mass, more preferably 15 to 75% by mass, and more preferably 20 to 60% from the viewpoint of more effectively obtaining the effects of the present invention. Mass% is particularly preferred.
  • the composition of the present invention may contain only one type of polymerizable compound or two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the coloring composition of the present invention preferably contains a photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited as long as it can polymerize a polymerizable compound, and is preferably selected from the viewpoints of characteristics, initiation efficiency, absorption wavelength, availability, cost, and the like.
  • the photopolymerization initiator examples include at least one active halogen compound selected from halomethyloxadiazole compounds and halomethyl-s-triazine compounds, 3-aryl-substituted coumarin compounds, lophine dimers, benzophenone compounds, acetophenone compounds And derivatives thereof, cyclopentadiene-benzene-iron complexes and salts thereof, and oxime compounds.
  • active halogen compound selected from halomethyloxadiazole compounds and halomethyl-s-triazine compounds, 3-aryl-substituted coumarin compounds, lophine dimers, benzophenone compounds, acetophenone compounds And derivatives thereof, cyclopentadiene-benzene-iron complexes and salts thereof, and oxime compounds.
  • Specific examples of the photopolymerization initiator include those described in paragraphs [0070] to [0077] of JP-A No. 2004-295116.
  • the oxime compound (hereinafter also referred to as “oxime photopolymerization initiator”) is not particularly limited, and is described in, for example, JP-A No. 2000-80068, WO 02 / 100903A1, and JP-A No. 2001-233842. These oxime compounds are mentioned. As specific examples of the oxime compound, the description in paragraph 0053 of JP2013-182215A can be referred to, and the contents thereof are incorporated in the present specification.
  • the oxime compound is more preferably a compound represented by the following general formula (1) or general formula (2).
  • R and X each represent a monovalent substituent, A represents a divalent organic group, Ar represents an aryl group, and n represents an integer of 1 to 5. .
  • R is preferably an acyl group from the viewpoint of high sensitivity, and specifically, an acetyl group, a propionyl group, a benzoyl group, and a toluyl group are preferable.
  • A represents an alkylene group substituted with an unsubstituted alkylene group or an alkyl group (for example, a methyl group, an ethyl group, a tert-butyl group, or a dodecyl group) from the viewpoint of increasing sensitivity and suppressing coloration with heating.
  • An alkylene group substituted with an alkenyl group eg, vinyl group, allyl group
  • an aryl group eg, phenyl group, p-tolyl group, xylyl group, cumenyl group, naphthyl group, anthryl group, phenanthryl group, styryl group
  • An alkylene group substituted with is preferred.
  • Ar is preferably a substituted or unsubstituted phenyl group from the viewpoint of increasing sensitivity and suppressing coloration with heating.
  • the substituent is preferably a halogen group such as a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • X is an alkyl group, an aryl group, an alkenyl group, an alkynyl group, an alkoxy group, an aryloxy group, an alkylthioxy group, an arylthioxy group or an amino group from the viewpoint of improving solvent solubility and absorption efficiency in the long wavelength region.
  • n is preferably an integer of 1 to 2.
  • R 101 represents an alkyl group, an alkanoyl group, an alkenoyl group, an aryloyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a heterocyclic oxycarbonyl group, a heterocyclic oxycarbonyl group, an alkylthiocarbonyl group, an arylthiocarbonyl.
  • Rf represents a carbocyclic aromatic group or a heterocyclic aromatic group.
  • R102 represents an alkyl group, an aryl group or a heterocyclic group, which may be substituted.
  • R 103 and R 104 each independently represents an alkyl group, an aryl group or a heterocyclic group, and these groups are further substituted with a halogen atom, an alkyl group, an aryl group, an alkoxy group, an alkylcarbonyl group or the like. Also good.
  • R 105 to R 111 are each independently a hydrogen atom, a halogen atom, an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloyl group, a heteroaryloyl group, an alkylthio group, an aryloylthio group, or a heteroaryloyl group.
  • the compound having a fluorene structure represented by the general formula (2) include compounds described in paragraph numbers 0087 to 0088 of JP 2014-177502 A, the contents of which are described in this specification. It will be incorporated.
  • the compound having a fluorene structure represented by the general formula (2) can be synthesized according to a synthesis method described in, for example, WO2014-050738.
  • oxime photopolymerization initiators include IRGACURE-OXE01 (manufactured by BASF), IRGACURE-OXE02 (manufactured by BASF), TR-PBG-304 (manufactured by Changzhou Strong Electronic New Materials Co., Ltd.), Adeka Arcles NCI-831 (manufactured by ADEKA), Adeka Arcles NCI-930 (manufactured by ADEKA) and the like can be used.
  • biimidazole compound As specific examples of the biimidazole compound, the description in paragraphs 0061 to 0070 of JP2013-182213A can be referred to, and the contents thereof are incorporated in the present specification.
  • an oxime compound having a fluorine atom can also be used as a photopolymerization initiator.
  • Specific examples of the oxime compound having a fluorine atom include compounds described in JP 2010-262028 A, compounds 24 and 36 to 40 described in JP-A-2014-500852, and compounds described in JP-A 2013-164471 ( C-3). This content is incorporated herein.
  • the content of the photopolymerization initiator in the total solid content of the coloring composition is preferably 3 to 20% by mass, more preferably 4 to 19% by mass, from the viewpoint of more effectively obtaining the effects of the present invention. 18% by mass is particularly preferred.
  • the composition of the present invention may contain only one type of photopolymerization initiator, or may contain two or more types. When two or more types are included, the total amount is preferably within the above range.
  • the colored composition of the present invention preferably contains an organic solvent.
  • the organic solvent is basically not particularly limited as long as it can satisfy the solubility of each coexisting component and the coating property when it is a colored composition, and in particular, the solubility, coating property, and safety of the binder. Is preferably selected in consideration of
  • organic solvent examples include esters, ethers, ketones, and aromatic hydrocarbons, and specific examples include those described in paragraph numbers 0161 to 0162 of JP2012-032754A.
  • the content of the organic solvent in the colored composition is preferably such that the total solid concentration in the composition is from 10 to 80% by mass, more preferably from 15 to 60% by mass.
  • the coloring composition of the present invention may contain only one type of organic solvent or two or more types of organic solvents. When two or more types are included, the total amount is preferably within the above range.
  • the coloring composition of this invention contains the alkali-soluble binder.
  • the alkali-soluble binder is not particularly limited except that it has alkali solubility, and can be preferably selected from the viewpoints of heat resistance, developability, availability, and the like.
  • the alkali-soluble binder is preferably a linear organic polymer, soluble in an organic solvent, and developable with a weak alkaline aqueous solution.
  • linear organic high molecular polymers include polymers having a carboxylic acid in the side chain, such as JP-A-59-44615, JP-B-54-34327, JP-B-58-12577, JP-B-54-. No. 25957, JP-A-59-53836, JP-A-59-71048, methacrylic acid copolymer, acrylic acid copolymer, itaconic acid copolymer, crotonic acid copolymer, etc. Examples thereof include polymers, maleic acid copolymers, partially esterified maleic acid copolymers, and acidic cellulose derivatives having a carboxylic acid in the side chain are also useful.
  • the alkali-soluble binder in the present invention includes those obtained by adding an acid anhydride to a polymer having a hydroxyl group, polyhydroxystyrene resins, polysiloxane resins, poly (2-hydroxyethyl (meth)). Acrylate), polyvinylpyrrolidone, polyethylene oxide, polyvinyl alcohol, and the like are also useful. Further, the linear organic high molecular polymer may be a copolymer of hydrophilic monomers.
  • Examples include alkoxyalkyl (meth) acrylate, hydroxyalkyl (meth) acrylate, glycerol (meth) acrylate, (meth) acrylamide, N-methylol acrylamide, secondary or tertiary alkyl acrylamide, dialkylaminoalkyl (meth) Acrylate, morpholine (meth) acrylate, N-vinylpyrrolidone, N-vinylcaprolactam, vinylimidazole, vinyltriazole, methyl (meth) acrylate, ethyl (meth) acrylate, branched or linear propyl (meth) acrylate, branched or straight Examples include chain butyl (meth) acrylate, phenoxyhydroxypropyl (meth) acrylate, and the like.
  • hydrophilic monomers include tetrahydrofurfuryl group, phosphoric acid group, phosphoric ester group, quaternary ammonium base, ethyleneoxy chain, propyleneoxy chain, sulfonic acid group and groups derived from salts thereof, morpholinoethyl group, etc. Monomers comprising it are also useful.
  • alkali-soluble binder a copolymer of maleimide and ethylene oxide as shown in (b1) or formula (b2) can also be preferably used.
  • R 1 represents a hydrogen atom, an aryl group, or an alkyl group.
  • Examples of the alkyl group when R 1 represents an alkyl group include a linear alkyl group having 1 to 10 carbon atoms, an alkyl group having a branched chain having 3 to 10 carbon atoms, and a cyclic alkyl group having 5 to 20 carbon atoms. Can be mentioned.
  • the alkyl group may have a substituent, and examples of the substituent that can be introduced into the alkyl group include a phenyl group, a carbonyl group, an alkoxy group, a hydroxy group, and an amino group.
  • R 1 represents an aryl group
  • examples of the aryl group include a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, a heteroaryl group containing a hetero atom, and the like. More specifically, a phenyl group, a naphthyl group, a biphenyl group, a benzimidazolyl group, a pyridyl group, a furyl group, and the like can be given.
  • the aryl group may have a substituent, and examples of the substituent that can be introduced into the aryl group include an alkyl group such as a methyl group, an ethyl group, a t-butyl group, and a cyclohexyl group, an alkoxy group such as a methoxy group, Examples thereof include a carboxy group, a hydroxy group, an amino group, a nitro group, a chloro group, and a bromo group.
  • R 2 represents a hydrogen atom or a methyl group
  • R 3 represents an alkylene group having 2 or 3 carbon atoms
  • R 4 represents a hydrogen atom, an aryl group, or an alkyl group
  • m represents an integer of 1 to 15.
  • Examples of the alkyl group when R 4 represents an alkyl group include a linear alkyl group having 1 to 20 carbon atoms, an alkyl group having a branched chain having 1 to 20 carbon atoms, and a cyclic alkyl group having 5 to 20 carbon atoms. Can be mentioned.
  • the alkyl group may have a substituent, and examples of the substituent that can be introduced into the alkyl group include a phenyl group, a carbonyl group, and an alkoxy group.
  • Examples of the aryl group when R 4 represents an aryl group include a monocyclic aryl group, a polycyclic aryl group, a condensed ring aryl group, and a heteroaryl group containing a heteroatom.
  • a phenyl group, a naphthyl group, an anthranyl group, a biphenyl group, a benzimidazolyl group, an indolyl group, an imidazolyl group, an oxazolyl group, a carbazolyl group, a pyridyl group, a furyl group, and the like can be given.
  • the aryl group may have a substituent, and examples of the substituent that can be introduced into the aryl group include a nonyl group, a methyl group, an ethyl group, a t-butyl group, a cyclohexyl group and other alkyl groups, and a methoxy group. Examples thereof include an alkoxy group, a carboxy group, a hydroxy group, an amino group, a nitro group, a chloro group, and a bromo group.
  • the alkali-soluble binder may have a polymerizable group in the side chain.
  • a polymer containing an allyl group, a (meth) acryl group, an allyloxyalkyl group or the like in the side chain is also useful.
  • examples of the above-mentioned polymer containing a polymerizable group include commercially available KS resist-106 (manufactured by Osaka Organic Chemical Industry Co., Ltd.), cyclomer P series (manufactured by Daicel Chemical Industries, Ltd.) and the like.
  • alcohol-soluble nylon, polyether of 2,2-bis- (4-hydroxyphenyl) -propane and epichlorohydrin, etc. are also useful.
  • polyhydroxystyrene resins, polysiloxane resins, acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferable, and from the viewpoint of development control.
  • acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins are preferable, and from the viewpoint of development control.
  • a copolymer having a repeating unit represented by the following general formula (2) and an acidic group is preferred, and more preferably a structural unit represented by the general formula (3) in addition to the general formula (2) and the acidic group.
  • R 20 represents a hydrogen atom or a methyl group
  • R 21 to R 25 each independently represents a hydrogen atom, a halogen atom, a cyano group, an alkyl group, or an aryl group.
  • R 11 represents a hydrogen atom or a methyl group.
  • R 12 and R 13 each independently represents a hydrogen atom or an unsaturated double bond having 3 to 20 carbon atoms as a partial structure.
  • R 12 and R 13 are not both hydrogen atoms, and at least one of R 12 and R 13 is a carbonyl group having 3 to 20 carbon atoms containing an unsaturated double bond as a partial structure. When represented, it may further contain a carboxy group as a partial structure.
  • acrylic resins include copolymers composed of monomers selected from benzyl (meth) acrylate, (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like, and commercially available KS resist 106 (Osaka).
  • benzyl (meth) acrylate (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like
  • commercially available KS resist 106 Osaka.
  • Organic Chemical Industry Co., Ltd.), Cyclomer P Series (manufactured by Daicel Chemical Industries, Ltd.) and the like are preferable.
  • the alkali-soluble binder may contain the structural unit derived from a compound with the following general formula (X).
  • R 1 represents a hydrogen atom or a methyl group
  • R 2 represents an alkylene group having 2 to 10 carbon atoms
  • R 3 represents a hydrogen atom or 1 to C carbon atoms that may contain a benzene ring.
  • 20 alkyl groups are represented.
  • n represents an integer of 1 to 15.
  • the alkylene group of R 2 preferably has 2 to 3 carbon atoms.
  • the alkyl group of R 3 has 1 to 20 carbon atoms, more preferably 1 to 10, and the alkyl group of R 3 may contain a benzene ring.
  • Examples of the alkyl group containing a benzene ring represented by R 3 include a benzyl group and a 2-phenyl (iso) propyl group.
  • the alkali-soluble binder preferably has a weight average molecular weight (polystyrene equivalent value measured by GPC method) of 1,000 to 200,00 from the viewpoint of developability, liquid viscosity, etc., and 2,000 to 100,000. Is more preferable, and 5,000 to 50,000 is particularly preferable.
  • the acid value of the alkali-soluble binder is preferably 10 to 1000 mg / KOH, more preferably 50 to 300 mg / KOH, still more preferably 50 to 200 mg / KOH, and particularly preferably 105 to 200 mg / KOH.
  • the content of the alkali-soluble binder is preferably 10 to 80% by mass, more preferably 20 to 60% by mass, based on the total solid content of the coloring composition.
  • the composition of the present invention may contain only one kind of alkali-soluble binder or two or more kinds. When two or more types are included, the total amount is preferably within the above range.
  • the coloring composition of the present invention may further contain a crosslinking agent.
  • the crosslinking agent is not particularly limited as long as the film can be cured by a crosslinking reaction.
  • the crosslinking agent is not particularly limited as long as the film can be cured by a crosslinking reaction.
  • at least selected from (a) an epoxy resin, (b) a methylol group, an alkoxymethyl group, and an acyloxymethyl group.
  • the coloring composition of the present invention contains a crosslinking agent
  • the content of the crosslinking agent is preferably 0.01 to 50% by mass, more preferably 0.5 to 30%, based on the total solid content of the coloring composition. % By mass.
  • the coloring composition of the present invention may contain a surfactant.
  • the surfactant may be nonionic, cationic, or anionic, but a surfactant having an ethylene oxide structure and a fluorosurfactant are preferred.
  • a surfactant having an ethylene oxide structure having an HLB (Hydrophile-Lipophile Balance) value in the range of 9.2 to 15.5 or a fluorosurfactant described in JP-A-2-54202 is preferred.
  • the coloring composition of the present invention contains a surfactant, the content of the surfactant is preferably 0.0001 to 2.0% by mass, more preferably 0, based on the total solid content of the coloring composition. 0.005 to 1.0 mass%.
  • the composition of the present invention may contain only one type of surfactant or two or more types of surfactant. When two or more types are included, the total amount is preferably within the above range.
  • the coloring composition of the present invention may contain a dye stabilizer.
  • a polymer surfactant polymer dispersant
  • the polymer dispersant include (co) polymers of unsaturated carboxylic acid esters such as polyacrylic acid esters; (partial) amine salts of (co) polymers of unsaturated carboxylic acid such as polyacrylic acid; (Partial) ammonium salt and (partial) alkylamine salt; (co) polymer of hydroxyl group-containing unsaturated carboxylic acid ester such as hydroxyl group-containing polyacrylic acid ester or knitted product thereof; sulfonic acid or phosphoric acid having a crosslinkable group And the like.
  • the crosslinkable group a known polymerizable group that can be cross-linked by a radical, an acid, or heat can be used. Specific examples include (meth) acryl groups, styrene groups, vinyl groups, cyclic ether groups, and methylol groups, with (meth) acryl groups, styrene groups, and vinyl groups being preferred, and (meth) acryl groups and styrene groups being preferred. More preferred. It is also effective to add the following anion salts (lithium salt, sodium salt, potassium salt, etc.) as a dye stabilizer. When the coloring composition of the present invention contains a dye stabilizer, the content of the dye stabilizer is preferably 0.01 to 50% by mass, more preferably 0, based on the total solid content of the coloring composition. .5 to 30% by mass.
  • the coloring composition of the present invention may contain an antioxidant.
  • the antioxidant include a radical scavenger, a peroxide decomposer, an ultraviolet absorber, and a singlet oxygen quencher.
  • the radical scavenger include phenolic antioxidants and hindered amine antioxidants.
  • phenolic antioxidants include hydroxyphenylpropionate compounds, hydroxybenzyl compounds, thiobisphenol compounds, thiomethylphenol compounds, alkanediylphenol compounds, and the like. Of these, hydroxyphenylpropionate compounds are preferred from the viewpoint of the stability of color characteristics.
  • a peroxide decomposer is a compound that decomposes peroxides generated by exposure to light into harmless substances and prevents the generation of new radicals.
  • phosphorus antioxidants for example, phosphorus antioxidants, sulfur And system antioxidants.
  • sulfur-based antioxidants are preferable from the viewpoint of the stability of color characteristics.
  • the ultraviolet absorber include salicylate-based antioxidants and benzophenone-based antioxidants.
  • a singlet oxygen quencher is a compound that can deactivate singlet oxygen by energy transfer from oxygen in a singlet state.
  • an ethylenic compound such as tetramethylethylene and cyclopentene, diethylamine, triethylamine, 1,4- Amines such as diazabicyclooctane (DABCO) and N-ethylimidazole, condensed polycyclic aromatic compounds such as optionally substituted naphthalene, dimethylnaphthalene, dimethoxyanthracene, anthracene and diphenylanthracene; 1,3-diphenylisobenzofuran
  • aromatic compounds such as 1,2,3,4-tetraphenyl-1,3-cyclopentadiene and pentaphenylcyclopentadiene, Harry H. et al.
  • transition metal chelate compounds such as nickel complexes, cobalt complexes, copper complexes, manganese complexes, and platinum complexes having bisdithio- ⁇ -diketone, bisphenyldithiol, and thiobisphenol as ligands.
  • sulfur antioxidant include thiopropionate compounds and mercaptobenzimidazole compounds. Of these, thiopropionate compounds are preferred from the viewpoint of the stability of color characteristics.
  • the antioxidants can be used alone or in admixture of two or more.
  • the content of the antioxidant is preferably 0.01 to 20 parts by mass, particularly preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the colorant.
  • the coloring composition of the present invention can contain a compound that functions as a curing accelerator.
  • a compound that functions as a curing accelerator For example, at least one compound selected from the group consisting of aromatic amine compounds, tertiary amine compounds, amine salts, phosphonium salts, amidine salts, amide compounds, thiol compounds, blocked isocyanate compounds, and imidazole ring-containing compounds can be used.
  • the coloring composition contains a curing accelerator, low-temperature curing of the coloring composition can be more effectively realized.
  • the storage stability of the colored composition can be further improved.
  • Examples of commercially available curing accelerators include Karenz MT series such as Karenz MTBD-1 (manufactured by Showa Denko KK).
  • a hardening accelerator can be used individually or in mixture of 2 or more types.
  • the content of the curing accelerator is preferably 0.01 to 20 parts by mass, particularly preferably 0.1 to 10 parts by mass with respect to 100 parts by mass of the polymerizable compound.
  • the coloring composition of the present invention can also contain a reduction inhibitor.
  • the reduction inhibitor is preferably a quinone compound, more preferably a quinone compound having a molecular weight of about 100 to 800 and having the following structure.
  • the coloring composition of the present invention can also contain an acid generator.
  • the acid generator may be a photoacid generator or a thermal acid generator, but a thermal acid generator is preferred. When a thermal acid generator is used, the heat resistance of the cured film tends to be further improved.
  • the thermal acid generator refers to an acid generator that generates an acid when heated at 100 to 250 ° C. at 101.25 hPa.
  • the acid generated is preferably an acid having a pKa of 5 or less. Specific examples of the acid generated include sulfonic acid, carboxylic acid, phosphoric acid and the like, and sulfonic acid is more preferable.
  • Thermal acid generators include ionic compounds (onium salts) and nonionic compounds.
  • ionic compound (onium salt) those containing no heavy metal or halogen ion are preferable, and onium salts of sulfonic acid are preferable.
  • Specific examples of the ionic thermal acid generator include triphenylsulfonium, 1-dimethylthionaphthalene, 1-dimethylthio-4-hydroxynaphthalene, 1-dimethylthio-4,7-dihydroxynaphthalene, 4-hydroxyphenyldimethyl.
  • Sulfonium benzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-hydroxyphenylmethylsulfonium, 2-methylbenzyl-4-acetylphenylmethylsulfonium, 2-methylbenzyl-4-benzoyloxyphenylmethylsulfonium, these Examples include methanesulfonate, trifluoromethanesulfonate, camphorsulfonate, p-toluenesulfonate, hexafluorophosphonate and the like.
  • the coloring composition of the present invention may further contain a bis (trifluoromethanesulfonyl) imide salt.
  • Heat resistance can be improved by including a bis (trifluoromethanesulfonyl) imide salt.
  • the bis (trifluoromethanesulfonyl) imide salt include potassium bis (trifluoromethanesulfonyl) imide, sodium bis (trifluoromethanesulfonyl) imide, lithium bis (trifluoromethanesulfonyl) imide and the like.
  • the content of the bis (trifluoromethanesulfonyl) imide salt is preferably from 0.1 to 2 mol, more preferably from 0.3 to 0.8 mol, based on 1 mol of the triarylmethane repeating unit of the polymer TP.
  • the coloring composition of the present invention may further contain various additives such as a filler, an ultraviolet absorber, an aggregation inhibitor, a sensitizer and a light stabilizer, as necessary.
  • the coloring composition of this invention can be adjusted by mixing each component mentioned above and arbitrary components as needed.
  • the components constituting the colored composition may be blended together, or may be blended sequentially after each component is dissolved and dispersed in a solvent.
  • the composition may be prepared by dissolving and dispersing all components in a solvent at the same time. If necessary, each component may be suitably used as two or more solutions / dispersions at the time of use (at the time of application). ) May be mixed to prepare a composition.
  • the colored composition of the present invention is preferably filtered with a filter for the purpose of removing foreign substances or reducing defects.
  • any filter can be used without particular limitation as long as it has been conventionally used for filtration.
  • fluorine resins such as polytetrafluoroethylene (PTFE), polyamide resins such as nylon-6 and nylon-6,6, polyolefin resins such as polyethylene and polypropylene (PP) (including high density and ultra high molecular weight), etc.
  • PTFE polytetrafluoroethylene
  • polyamide resins such as nylon-6 and nylon-6,6, polyolefin resins such as polyethylene and polypropylene (PP) (including high density and ultra high molecular weight)
  • PP polypropylene
  • the pore size of the filter is suitably about 0.01 to 7.0 ⁇ m, preferably about 0.01 to 3.0 ⁇ m, more preferably about 0.05 to 0.5 ⁇ m. By setting it as this range, it becomes possible to remove reliably the fine foreign material which inhibits preparation of the uniform and smooth coloring composition in a post process.
  • the filtering by the first filter may be performed only once or may be performed twice or more.
  • the pore diameter here can refer to the nominal value of the filter manufacturer.
  • a commercially available filter for example, it can be selected from various filters provided by Nippon Pole Co., Ltd., Advantech Toyo Co., Ltd., Japan Entegris Co., Ltd. (formerly Japan Microlith Co., Ltd.) or KITZ Micro Filter Co., Ltd. .
  • the second filter a filter formed of the same material as the first filter described above can be used.
  • the filtering by the first filter may be performed only with the dispersion, and the second filtering may be performed after mixing other components.
  • the colored composition of the present invention can form a cured film excellent in hue and contrast, for forming a colored layer (for forming colored pixels) such as a color filter used in an image display device or a solid-state imaging device, Moreover, it can use suitably as preparation uses, such as printing ink, inkjet ink, and a coating material.
  • the cured film of the present invention is formed by curing the colored composition of the present invention.
  • Such a cured film is preferably used for a color filter.
  • the color filter of the present invention may be formed by any method as long as it can form a colored region (colored pattern) cured by applying the colored composition of the present invention on a substrate. Preferably, it is produced using the coloring composition of the present invention.
  • the production method described in paragraphs 0359 to 0371 of JP2011-252065A can also be employed. .
  • the method for producing a color filter of the present invention includes a step of forming a colored composition layer using the colored composition of the present invention, a step of exposing the colored composition layer in a pattern-like manner, and an unexposed portion of the colored composition layer. And removing the film to form a colored pattern. Furthermore, you may provide the process (prebaking process) of baking a colored composition layer, and the process (post-baking process) of baking the developed coloring pattern as needed.
  • the colored composition layer is formed by applying the colored composition of the present invention on the substrate.
  • the substrate for example, alkali-free glass, sodium glass, Pyrex (registered trademark) glass, quartz glass used for liquid crystal display elements and the like, and those obtained by attaching a transparent conductive film thereto, solid-state imaging elements, and the like are used.
  • the photoelectric conversion element substrate include a silicon substrate and a plastic substrate. On these substrates, a black matrix for isolating each pixel may be formed, or a transparent resin layer may be provided for promoting adhesion. Further, if necessary, an undercoat layer may be provided on the substrate in order to improve adhesion to the upper layer, prevent diffusion of substances, or flatten the surface.
  • the plastic substrate preferably has a gas barrier layer and / or a solvent resistant layer on its surface.
  • a driving substrate on which a thin film transistor (TFT) of a thin film transistor (TFT) type color liquid crystal display device is disposed (hereinafter referred to as “TFT type liquid crystal driving substrate”) is used as the substrate.
  • TFT type liquid crystal driving substrate a driving substrate on which a thin film transistor (TFT) of a thin film transistor (TFT) type color liquid crystal display device is disposed
  • a color filter using the colored composition of the present invention can also be formed on the top to produce a color filter.
  • the substrate in the TFT type liquid crystal driving substrate include glass, silicone, polycarbonate, polyester, aromatic polyamide, polyamideimide, and polyimide. These substrates may be subjected to appropriate pretreatment such as chemical treatment with a silane coupling agent, plasma treatment, ion plating, sputtering, gas phase reaction method, vacuum deposition, etc., if desired.
  • Application method of the coloring composition is preferably coating, and it is preferable to apply by a method such as spin coating, slit coating, cast coating, roll coating, bar coating, and ink jet.
  • the colored composition layer formed on the substrate is preferably dried (prebaked).
  • Pre-baking is performed in a temperature range of 50 ° C. to 140 ° C., preferably about 70 ° C. to 110 ° C., using a hot plate, an oven, or the like, and can be performed under conditions of 10 seconds to 300 seconds.
  • pre-baking may be performed in combination with high-frequency processing.
  • the high frequency treatment can be used alone.
  • vacuum treatment can be performed before pre-baking.
  • the degree of vacuum is preferably 13 to 133 Pa, and more preferably 26 to 66.5 Pa.
  • the thickness of the colored composition layer formed from the colored composition is appropriately selected according to the purpose.
  • a range of 0.2 to 5.0 ⁇ m is preferable, a range of 1.0 to 4.0 ⁇ m is more preferable, and a range of 1.5 to 3.5 ⁇ m is most preferable.
  • a range of 0.2 to 5.0 ⁇ m is preferable, a range of 0.3 to 2.5 ⁇ m is more preferable, and a range of 0.3 to 1.5 ⁇ m is most preferable.
  • the thickness of a coloring composition layer is a film thickness after prebaking.
  • the film (colored composition layer) made of the colored composition formed on the substrate as described above is exposed through, for example, a photomask.
  • a photomask As light or radiation applicable to exposure, g-line, h-line, i-line, j-line, KrF light and ArF light are preferable, and i-line is particularly preferable.
  • i-line is particularly preferable.
  • the i-line to the irradiation light is preferably irradiated at an exposure dose of 100mJ / cm 2 ⁇ 10000mJ / cm 2.
  • exposure rays include ultra high pressure, high pressure, medium pressure, low pressure mercury lamps, chemical lamps, carbon arc lamps, xenon lamps, metal halide lamps, various visible and ultraviolet laser light sources, fluorescent lamps, tungsten lamps, solar Light or the like can also be used.
  • the irradiation light is preferably an ultraviolet laser having a wavelength in the range of 300 nm to 380 nm, and more preferably an ultraviolet laser having a wavelength in the range of 300 nm to 360 nm.
  • the third harmonic (355 nm) of an Nd: YAG (yttrium, aluminum, garnet) laser which is a relatively inexpensive solid laser with a large output
  • the XeCl (308 nm), XeF (353 nm) of an excimer laser can be suitably used.
  • the exposure amount of the object to be exposed is in the range of 1 mJ / cm 2 to 100 mJ / cm 2 , and more preferably in the range of 1 mJ / cm 2 to 50 mJ / cm 2 . An exposure amount within this range is preferable from the viewpoint of pattern formation productivity.
  • a color filter for a liquid crystal display device exposure using mainly h-line and i-line is preferably used by a proximity exposure machine and a mirror projection exposure machine. Further, when manufacturing a color filter for a solid-state image sensor, it is preferable to mainly use i-line in a stepper exposure machine.
  • the photomask used is for forming a depression such as a through hole in addition to a pattern for forming a pixel (colored pattern). Those provided with a pattern are used.
  • the colored composition layer exposed as described above can be heated.
  • the exposure can be performed while flowing a nitrogen gas in the chamber in order to suppress oxidation fading of the coloring material in the colored composition layer.
  • Step of forming colored pattern Subsequently, development is performed with a developer on the colored composition layer after exposure. Thereby, a negative type or positive type coloring pattern (resist pattern) can be formed.
  • the uncured portion of the coating film after exposure is eluted in the developer, and only the cured portion remains on the substrate.
  • Any developer can be used as long as it dissolves the coating film (colored composition layer) of the colored composition in the uncured part, but does not dissolve the cured part.
  • combinations of various organic solvents and alkaline aqueous solutions can be used. Examples of the organic solvent used for development include the above-described solvents that can be used when preparing the colored composition of the present invention.
  • alkaline aqueous solution examples include tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, trimethylbenzylammonium hydroxide, benzyltrimethylammonium hydroxide, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate Sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0 ]
  • concentration of an alkaline compound such as -7-undecene is 0.001 to 10% by mass, preferably 0.01 to 1% by mass.
  • alkali aqueous solution was dissolved at a.
  • the alkali concentration is preferably adjusted to pH 11 to 13, more preferably pH 11.5 to 12.5.
  • An appropriate amount of a water-soluble organic solvent such as methanol or ethanol, a surfactant, or the like can be added to the alkaline aqueous solution.
  • the development temperature is usually 20 ° C. to 30 ° C., and the development time is 20 seconds to 90 seconds.
  • Development may be any of a dip method, a shower method, a spray method, and the like, and may be combined with a swing method, a spin method, an ultrasonic method, or the like. It is also possible to prevent development unevenness by previously moistening the surface to be developed with water or the like before touching the developer. It is also possible to develop with the substrate tilted. Further, when manufacturing a color filter for a solid-state image sensor, paddle development is also used.
  • a rinsing process for washing and removing excess developer is performed, followed by drying, followed by heat treatment (post-baking) to complete the curing.
  • the rinse treatment is usually performed with pure water, but to save liquid, pure water is used in the final cleaning, and used pure water is used in the initial stage of cleaning, or the substrate is inclined and cleaned. You may use the method of using ultrasonic irradiation together.
  • a heat treatment at about 200 ° C. to 250 ° C. is usually performed.
  • the coating film after development is continuously or batch-treated using a heating means such as a hot plate, a convection oven (hot air circulation dryer) or a high-frequency heater so as to satisfy the above conditions. It can be done with an expression.
  • a colored pattern (pixel) formed using a colored composition can be post-exposed by irradiating with ultraviolet rays.
  • the colored pattern can be further cured by subjecting the formed colored pattern to heat treatment (so-called post-bake treatment).
  • This heat treatment can be performed by, for example, a hot plate, various heaters, an oven, or the like.
  • the temperature during the heat treatment is preferably 100 ° C. to 300 ° C., more preferably 150 ° C. to 250 ° C.
  • the heating time is preferably about 10 minutes to 120 minutes.
  • the colored pattern thus obtained constitutes a pixel in the color filter.
  • the above steps may be repeated according to a desired number of colors.
  • the post-exposure and / or post-bake treatment may be performed each time the formation, exposure, and development of a single-color coloring composition layer is completed (for each color), or all colors having a desired number of colors may be used. After the formation, exposure, and development of the composition layer are completed, the post-exposure and / or post-bake treatment may be performed collectively.
  • the coloring composition of this invention is applicable also to the manufacturing method of the color filter containing a dry etching process.
  • a step of forming a colored layer using the colored composition of the present invention Manufacturing comprising a step of forming a photoresist layer on a colored layer, a step of patterning the photoresist layer by exposure and development to obtain a resist pattern, and a step of dry etching the colored layer using the resist pattern as an etching mask A method is mentioned.
  • the color filter obtained by the method for producing a color filter of the present invention (the color filter of the present invention) is excellent in hue and contrast because the colored composition of the present invention is used.
  • the color filter of the present invention can be used for an image display device or a solid-state image sensor, and is particularly suitable for use in a liquid crystal display device. When used in a liquid crystal display device, it is possible to display an image having excellent spectral characteristics and contrast while achieving a good hue.
  • the description has mainly focused on the use for forming the color pattern of the color filter in the above, but it is also applicable to the formation of a black matrix for isolating the color pattern (pixel) constituting the color filter. can do.
  • a coloring composition containing a black pigment processed pigment such as carbon black or titanium black is used, followed by coating, exposure, and development, and then post-baking as necessary. Can be formed.
  • the image display device of the present invention comprises the color filter of the present invention.
  • the image display device include a liquid crystal display device and an organic electroluminescence (organic EL) display device. It is particularly suitable for liquid crystal display devices.
  • the liquid crystal display device provided with the color filter of the present invention can display a high-quality image with a good display image color and excellent display characteristics.
  • the image display device For the definition of the image display device and details of each display device, refer to, for example, “Electronic Display Device (Akio Sasaki, Kogyo Kenkyukai, 1990)”, “Display Device (Junsho Ibuki, Sangyo Tosho) Issued in 1989).
  • the liquid crystal display device is described, for example, in “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, Industrial Research Co., Ltd., published in 1994)”.
  • the liquid crystal display device to which the present invention can be applied is not particularly limited, and can be applied to, for example, various types of liquid crystal display devices described in the “next generation liquid crystal display technology”.
  • the color filter of the present invention is particularly effective for a color TFT (Thin Film Transistor) type liquid crystal display device.
  • the color TFT liquid crystal display device is described in, for example, “Color TFT liquid crystal display (issued in 1996 by Kyoritsu Publishing Co., Ltd.)”.
  • the present invention relates to a liquid crystal display device with a wide viewing angle, such as a horizontal electric field driving method such as IPS (In Plane Switching), a pixel division method such as MVA (Multi-domain Vertical Alignment), a STN (Super-Twist Nematic).
  • the color filter of the present invention can also be used for a bright and high-definition COA (Color-filter On Array) system.
  • the color filter of the present invention When the color filter of the present invention is used in an image display device, high contrast can be realized when combined with a conventionally known three-wavelength cold-cathode tube, but further, red, green, and blue light-emitting diode light sources (RGB-LED) ) As a backlight, an image display device having high luminance and high color purity and good color reproducibility can be provided.
  • RGB-LED red, green, and blue light-emitting diode light sources
  • the solid-state imaging device of the present invention includes the above-described color filter of the present invention.
  • the configuration of the solid-state imaging device of the present invention is not particularly limited as long as it is a configuration that includes the color filter of the present invention and functions as a solid-state imaging device.
  • transfer electrodes made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD (charge coupled device) image sensor, CMOS (complementary metal oxide semiconductor) image sensor, etc.) are provided.
  • a nitride film formed on the light-shielding film so as to cover the entire surface of the light-shielding film and the photodiode light-receiving part.
  • the device has a device protective film made of silicone or the like, and has the color filter for a solid-state imaging device of the present invention on the device protective film.
  • the measurement conditions were N-methyl-2-pyrrolidone (NMP) with a sample concentration of 0.35 mass%, a flow rate of 0.3 mL / min, a sample injection volume of 10 ⁇ L, a measurement temperature of 40 ° C., and an ultraviolet detector. This is the value obtained.
  • NMP N-methyl-2-pyrrolidone
  • An amount having a weight average molecular weight of 1500 or less was estimated and calculated from data obtained by GPC measurement.
  • TAM1 was synthesized according to the following route.
  • ⁇ TAM2-6> Synthesis was performed in the same manner as in Synthesis Example 1 except that the amount of dodecyl mercaptan in the polymerization step was changed.
  • TAM7-15> It synthesize
  • TAM23> This compound was synthesized in the same manner as TAM3 except that Compound 3 was changed to N, N, N ′, N′-tetraethyl-4,4′-diaminobenzophenone.
  • the coloring composition was prepared by mixing raw materials having the following composition.
  • -composition- Colorant 5.1 parts by weight Polymerizable compound (T-1): 6.0 parts by weight Alkali-soluble binder (U-2): 5.3 parts by weight Photoinitiator (V-4) ... 0.3 parts by mass, curing accelerator (V-5) ... 0.2 parts by mass, solvent (X-1) ... 71 parts by mass, solvent (X-3) ... 13 parts by mass / Surfactant (Z-1) ... 0.01 parts by mass
  • Colorant The following structure. In the following formula, the numerical value written in the repeating unit is the mass ratio of the charged raw materials.
  • Surfactant (Z-1): The following mixture (Mw 14000)
  • the colored curable resin composition obtained above was applied on a 100 mm ⁇ 100 mm glass substrate (1737, manufactured by Corning) by spin coating, and then dried at room temperature for 30 minutes to volatilize volatile components. To obtain a colored layer.
  • This colored layer was irradiated with i-rays (wavelength 365 nm) exposed on the entire surface without using a photomask to form a latent image.
  • An ultra-high pressure mercury lamp was used as the i-line light source, and it was irradiated as parallel light. At this time, the irradiation light quantity was 40 mJ / cm 2 .
  • the colored layer on which the latent image was formed was developed with an aqueous solution of sodium carbonate / sodium bicarbonate (concentration 2.4%) at 26 ° C. for 45 seconds, and then rinsed with running water for 20 seconds. , Dried with spray. The dried film was baked at 230 ° C. for 20 minutes in a clean oven to obtain a cured film. The following evaluation was performed about the cured film obtained above.
  • ⁇ Heat resistance> The color difference ⁇ Eab between the transmission spectrum of the cured film obtained above and the transmission spectrum when the cured film obtained above was additionally baked at 230 ° C. for 80 minutes was calculated. A smaller ⁇ Eab value indicates better heat resistance.
  • ⁇ Eab is less than 2 ... 6 ⁇ Eab is 2 or more and less than 3 ⁇ ⁇ ⁇ 5 ⁇ Eab is 3 or more and less than 4 ⁇ ⁇ ⁇ 4 ⁇ Eab is 4 or more and less than 5 ⁇ ⁇ ⁇ 3 ⁇ Eab is 5 or more and less than 10 2 ⁇ Eab is 10 or more ⁇ ⁇ ⁇ 1
  • ⁇ Solvent resistance (color difference)>
  • the cured film obtained above is heated at 230 ° C. for 30 minutes, and then immersed in propylene glycol monomethyl ether acetate (PGMEA) at 25 ° C. for 10 minutes, and the chromaticity before and after immersion is measured to change the color.
  • the index ⁇ Eab was calculated.
  • the ⁇ Eab value was calculated from the transmission spectrum of the cured film before and after being immersed in PGMEA. In addition, when the value of ⁇ Eab was 3 or less, the hue change was small and the solvent resistance was excellent.
  • ⁇ Eab is 1.5 or more and less than 2, 5 ⁇ Eab is 2 or more and less than 3.5 4 ⁇ Eab is 3.5 or more and less than 4, 3 ⁇ Eab is 4 or more and less than 5, 2 ⁇ Eab is 5 or more ⁇ ⁇ ⁇ 1
  • a colored composition is applied onto a glass substrate with ITO (Indium Tin Oxide) electrode (trade name: 1737 manufactured by Corning) to a thickness of 2.0 ⁇ m after drying, and dried in an oven at 100 ° C. for 60 seconds ( Pre-baked). Thereafter, exposure was performed at 100 mJ / cm 2 without using a mask (illuminance was 20 mW / cm 2 ), and a 1% aqueous solution of an alkali developer (trade name: CDK-1, manufactured by Fuji Film Electronics Materials Co., Ltd.) was used. The film was developed at 25 ° C., washed with water and dried, and then heat-treated (post-baked) in an oven at 230 ° C.
  • ITO Indium Tin Oxide
  • the example was able to form a cured film excellent in heat resistance and solvent resistance. Furthermore, the cured film was excellent in voltage holding ratio. On the other hand, the comparative example could not achieve both heat resistance and solvent resistance.
  • the coloring composition was prepared by mixing raw materials having the following composition.
  • -composition- Colorant 5.1 parts by weight Polymerizable compound (T-1): 6.0 parts by weight Alkali-soluble binder (U-2): 5.3 parts by weight Photoinitiator (V-4) ... 0.3 parts by mass / curing accelerator (V-5) ... 0.2 parts by mass / additive (W-1) ... 0.5 parts by mass / solvent (X -1) ... 71 parts by mass, solvent (X-3) ... 13 parts by mass, surfactant (Z-1) ... 0.01 parts by mass
  • Colorant Colorant described in the following table Polymerizable compound (T-1), alkali-soluble binder (U-2), photopolymerization initiator (V-4), curing accelerator (V-5), solvent (X -1), solvent (X-3), surfactant (Z-1): the above-described polymerizable compound (T-1), alkali-soluble binder (U-2), photopolymerization initiator (V-4), Curing accelerator (V-5), solvent (X-1), solvent (X-3), surfactant (Z-1) Additive (W-1): Potassium bis (trifluoromethanesulfonyl) imide (Mitsubishi Materials Corporation)
  • the heat resistance, solvent resistance and voltage holding ratio were evaluated in the same manner as in Test Example 1. The results are shown in the table below. From the above results, the example was able to form a cured film excellent in heat resistance and solvent resistance. Furthermore, the cured film was excellent in voltage holding ratio.

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Abstract

L'invention concerne une composition colorante qui présente une excellente résistance à la chaleur et une excellente résistance aux solvants, un film durci, un filtre coloré, un procédé de fabrication du filtre coloré, un élément d'imagerie à semi-conducteurs, un dispositif d'affichage d'image, et un polymère. La composition colorante contient un composé polymérisable, ainsi qu'un polymère TP qui comprend une unité structurale A ayant une structure triarylméthane, et une unité structurale B possédant un groupe de réticulation. Le polymère TP a une masse moléculaire moyenne en poids de 3 000 à 500 000. La proportion du composé A, qui a une structure triarylméthane et une masse moléculaire moyenne en poids inférieure ou égale à 1 500, n'excède pas 20 % en masse dans le polymère TP.
PCT/JP2016/055788 2015-02-27 2016-02-26 Composition colorante, film durci, filtre coloré, procédé de fabrication d'un filtre coloré, élément d'imagerie à semi-conducteurs, dispositif d'affichage d'image, et polymère WO2016136936A1 (fr)

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JP2021517921A (ja) * 2018-09-06 2021-07-29 エルジー・ケム・リミテッド 化合物、着色剤組成物、感光材、カラーフィルタおよびディスプレイ装置
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JP2021517601A (ja) * 2018-09-04 2021-07-26 エルジー・ケム・リミテッド 着色剤組成物、感光材、カラーフィルタおよびディスプレイ装置
JP7120526B2 (ja) 2018-09-04 2022-08-17 エルジー・ケム・リミテッド 着色剤組成物、感光材、カラーフィルタおよびディスプレイ装置
JP2021517921A (ja) * 2018-09-06 2021-07-29 エルジー・ケム・リミテッド 化合物、着色剤組成物、感光材、カラーフィルタおよびディスプレイ装置
JP7120527B2 (ja) 2018-09-06 2022-08-17 エルジー・ケム・リミテッド 化合物、着色剤組成物、感光材、カラーフィルタおよびディスプレイ装置
KR20220020902A (ko) 2019-07-25 2022-02-21 후지필름 가부시키가이샤 착색 조성물, 막, 컬러 필터, 고체 촬상 소자 및 화상 표시 장치

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