WO2015152051A1 - 着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 - Google Patents

着色組成物、硬化膜、カラーフィルタ、カラーフィルタの製造方法、固体撮像素子および画像表示装置 Download PDF

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WO2015152051A1
WO2015152051A1 PCT/JP2015/059628 JP2015059628W WO2015152051A1 WO 2015152051 A1 WO2015152051 A1 WO 2015152051A1 JP 2015059628 W JP2015059628 W JP 2015059628W WO 2015152051 A1 WO2015152051 A1 WO 2015152051A1
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group
carbon atoms
general formula
dye
rtp
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PCT/JP2015/059628
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English (en)
French (fr)
Japanese (ja)
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晃男 片山
樋口　聡
孝太郎 岡部
藤田　明徳
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富士フイルム株式会社
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Priority to JP2016511623A priority Critical patent/JP6285539B2/ja
Publication of WO2015152051A1 publication Critical patent/WO2015152051A1/ja

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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
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
    • C09J133/04—Homopolymers or copolymers of esters
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/38—Polymerisation using regulators, e.g. chain terminating agents, e.g. telomerisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/46—Polymerisation initiated by wave energy or particle radiation
    • C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L101/00—Compositions of unspecified 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
    • 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
    • C09B11/24—Phthaleins containing amino groups ; Phthalanes; Fluoranes; Phthalides; Rhodamine dyes; Phthaleins having heterocyclic aryl rings; Lactone or lactame forms of triarylmethane dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B47/00—Porphines; Azaporphines
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • 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
    • 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
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
    • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images

Definitions

  • the present invention relates to a colored composition, a cured film, a color filter, a method for producing a color filter, a solid-state imaging device, and an image display device.
  • a pigment dispersion method is used as one of methods for preparing a colored composition used for producing a color filter used in a liquid crystal display device or a solid-state imaging device (CCD (Charge Coupled Devices), CMOS (Complementary Metal-Oxide Semiconductor), etc.
  • This pigment dispersion method is a method for producing a color filter by a photolithography method using a colored composition in which a pigment is dispersed in various photosensitive compositions. This is a method suitable for producing a color filter with high positional accuracy, a large screen, and high definition because patterning is performed by a photolithography method.
  • a colored composition is applied by a spin coater or a roll coater to form a coating film, and a colored pattern is formed by exposing and developing the coating film.
  • a color filter can be obtained by repeating for each color.
  • color filters tend to be used not only for monitors but also for televisions (TVs) in liquid crystal display (LCD) 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 are also required to further improve color characteristics such as reduction of color unevenness and improvement of color resolution.
  • Patent Documents 1 to 3 In order to satisfy recent chromaticity requirements, techniques using dyes have been developed instead of pigments conventionally used as colorants (for example, Patent Documents 1 to 3). Among these, for a color filter having a blue hue, a technique using a triarylmethane dye as a color material has been proposed (for example, Patent Documents 4 to 6). In addition, a technique for insolubilizing triarylmethane dyes by multimerization has been proposed (Patent Document 7).
  • Japanese Patent No. 3387541 Japanese Patent Laid-Open No. 6-230210 JP 2008-292970 A JP 2009-86375 A International publication WO2011 / 162217 pamphlet JP 2011-70171 A JP 2011-116802 A JP 2013-57053 A
  • a dye When a dye is used as a colorant, it tends to be poor in solvent resistance because it is more soluble in a solvent than a pigment. This is because the dye develops color in a molecular state, so that the dye molecule can move freely in the film to some extent even after the coating film is cured. For this reason, for example, when another color resist or overcoat is applied over the coating film, the dye tends to easily elute into other colored layers or overcoat layers applied later. A colored layer may be formed. In particular, in a liquid crystal display device, in addition to the elution of dyes by overcoating with other color resists and overcoats, when an LCD panel is formed, there is a possibility that the dye components are eluted in the liquid crystal.
  • an object of the present invention is to provide a colored composition capable of forming a colored layer having high luminance and excellent solvent resistance when a colored layer such as a color filter is formed.
  • Another object of the present invention is to provide a cured film, a color filter, a method for producing the same, and a solid-state imaging device and an image display device that are provided with the color filter and are capable of displaying good image quality.
  • a purple colorant is a xanthene dye represented by the following general formula (I-1a), a pyromethene dye represented by the following general formula (II), and a tetraazaporphyrin represented by the following general formula (III)
  • R 1 to R 4 each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • —CH 2 — contained in the saturated hydrocarbon group may be 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.
  • R 3 and R 4 may combine with 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 5A 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 5B and R 5C may be independently the same or different; a represents 0 or 1; when a represents 0, any group in the xanthene dye structure contains 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—,
  • the dye cation includes at least one of a triarylmethane dye structure represented by the following general formula (TP1) and a triarylmethane dye structure represented by the following general formula (TP2).
  • TP1 triarylmethane dye structure
  • TP2 triarylmethane dye structure represented by the following general formula (TP2).
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable group
  • Rtp 5 , Rtp 6 , Rtp 8 , Rtp 9 And Rtp 11 each independently represents a substituent.
  • Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group, a group having a crosslinkable group, or NRtp 71 Rtp 72 .
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable group.
  • Rtp 10 represents a hydrogen atom, an alkyl group, an aryl group or a group having a crosslinkable group.
  • a, b and c each independently represents an integer of 0 to 4; a, when b and c is 2 or more, Rtp 5 together, Rtp 6 together, Rtp 8 and between Rtp 9 each other, respectively, may be bonded to each other to form a ring.
  • ⁇ 5> The colored composition according to any one of ⁇ 1> to ⁇ 4>, wherein the dye cation has a crosslinkable group.
  • a divalent or higher anion is —SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , a group containing a structure represented by the following general formula (B2) or a structure represented by the following general formula (B3)
  • R 11 and R 12 each independently represents —SO 2 — or —CO—
  • General formula (B3) In the general formula (B3), R 13 represents —SO 2 — or —CO—;
  • R 14 and R 15 each independently represents —SO 2 —, —CO— or —CN.
  • ⁇ 7> CI of Pigment Blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66, 79, 80 and Pigment Green 7
  • the coloring composition according to any one of ⁇ 1> to ⁇ 6> further comprising at least one selected from those changed to OH.
  • the colored composition according to any one of ⁇ 1> to ⁇ 7> further containing a binder resin, a polymerizable compound, and a photopolymerization initiator.
  • ⁇ 9> The colored composition according to any one of ⁇ 1> to ⁇ 8>, which is used for forming a colored layer of a color filter.
  • ⁇ 10> A cured film obtained by curing the colored composition according to any one of ⁇ 1> to ⁇ 9>.
  • ⁇ 11> A color filter using the colored composition according to any one of ⁇ 1> to ⁇ 9>.
  • ⁇ 12> a step of applying the colored composition according to any one of ⁇ 1> to ⁇ 9> on a support to form a colored composition layer, a step of exposing the colored composition layer in a pattern, And a step of developing and removing an unexposed portion to form a colored pattern.
  • a solid-state imaging device having a color filter according to ⁇ 11> or a color filter obtained by the method for producing a color filter according to ⁇ 12>.
  • ⁇ 14> An image display device having the color filter according to ⁇ 11> or the color filter obtained by the method for producing a color filter according to ⁇ 12>.
  • the present invention it is possible to provide a coloring composition having high luminance and excellent solvent resistance.
  • a cured film it has become possible to provide a cured film, a color filter, a method for producing a color filter, a solid-state imaging device, and a liquid crystal display device using the colored composition.
  • the total solid content refers to the total mass of components excluding the solvent from the total composition of the colored composition.
  • the notation which does not describe substitution and unsubstituted includes the group which has a substituent with the group 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).
  • radiation in the present specification means, for example, an emission line spectrum of a mercury lamp, far ultraviolet rays represented by excimer laser, extreme ultraviolet rays (EUV light), X-rays, electron beams, and the like.
  • light means actinic rays or radiation.
  • exposure in this specification is not only exposure with far-ultraviolet rays such as mercury lamps and excimer lasers, X-rays, EUV light, but also drawing with particle beams such as electron beams and ion beams. Are also included in the exposure.
  • (meth) acrylate represents both and / or acrylate and methacrylate
  • (meth) acryl represents both and / or acryl and “(meth) acrylic”
  • "Acryloyl” represents both and / or acryloyl and methacryloyl.
  • “monomer” and “monomer” are synonymous.
  • 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 means a compound having a polymerizable functional group, and may be a monomer or a polymer.
  • 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
  • AC represents an acetyl 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 in the present invention refers to that measured by gel permeation chromatography (GPC) unless otherwise specified.
  • the total solid content refers to the total mass of the components excluding the solvent from the total composition of the composition.
  • the solid content in the present invention is a solid content at 25 ° C.
  • the coloring composition of the present invention (hereinafter also referred to as the composition of the present invention) is a solvent comprising a salt compound composed of a dye cation and a divalent or higher anion, and 1.0% by mass or more of the salt compound at 25 ° C. And at least one purple colorant selected from a xanthene dye, a pyromethene dye and a tetraazaporphyrin dye, wherein the dye cation has 1 to 20 triarylmethane dye structures in one molecule, To do. By setting it as such a structure, the coloring composition with high brightness
  • the salt compound by dissolving the salt compound in a solvent, for example, higher brightness can be obtained as compared with the case where the dye is raked. Furthermore, light resistance can be improved by using at least one purple colorant selected from a xanthene dye, a pyromethene dye and a tetraazaporphyrin dye in combination with the salt compound. This is thought to be based on the excitation energy of the excited triarylmethane dye cation being received in the form of fluorescence by the purple colorant to relax the excited triarylmethane dye cation.
  • the salt compound contained in the composition of the present invention comprises a dye cation and a divalent or higher anion.
  • Dye cation has 1 to 20 triarylmethane dye structures in one molecule.
  • the number of triarylmethane dye structures in one molecule of the dye cation is preferably 1 to 4, and more preferably 2 or 3.
  • the solvent solubility of the salt compound used for this invention can be made more favorable. Therefore, the salt compound used in the present invention can be suitably used as a color material for a color resist, for example.
  • the dye cation may have a crosslinkable group. The crosslinkable group will be described later.
  • the dye cation preferably includes at least one of a triarylmethane dye structure represented by the following general formula (TP1) and a triarylmethane dye structure represented by the following general formula (TP2).
  • TP1 and TP2 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable group
  • Rtp 5 , Rtp 6 , Rtp 8 , Rtp 9 And Rtp 11 each independently represents a substituent.
  • Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group, a group having a crosslinkable group, or NRtp 71 Rtp 72 .
  • Rtp 71 and Rtp 72 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable group.
  • Rtp 10 represents a hydrogen atom, an alkyl group, an aryl group or a group having a crosslinkable group.
  • a, b and c each independently represents an integer of 0 to 4; a, when b and c is 2 or more, Rtp 5 together, Rtp 6 together, Rtp 8 and between Rtp 9 each other, respectively, may be bonded to each other to form a ring.
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable 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 may have a substituent, but is preferably unsubstituted. 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.
  • substituent that the aryl group may have include the substituents mentioned in the section of the substituent group A described later.
  • the group having a crosslinkable group may comprise only a crosslinkable group, or may contain a linking group in addition to the crosslinkable group.
  • the group having a crosslinkable group is preferably a group represented by -L 0 -P 0 .
  • L 0 represents a single bond or a divalent linking group
  • P 1 represents a crosslinkable group.
  • crosslinkable group a crosslinkable group that can be crosslinked by a radical, an acid, or heat can be used.
  • Specific examples include a group having an ethylenically unsaturated double bond, a (meth) acryl group, a styrene group, a vinyl group, an allyl group, and a cyclic ether group, and a (meth) acryl group, a styrene group, and a vinyl group.
  • at least one selected from allyl groups is preferred, at least one selected from (meth) acrylic groups, styrene groups and vinyl groups is more preferred, and (meth) acrylic groups and styrene groups are more preferred.
  • the cyclic ether group is preferably an epoxy group or an oxetanyl group, and more preferably an epoxy group.
  • the divalent linking group includes an alkylene group, an arylene group, a heterocyclic linking group, —CH ⁇ CH—, —O—, —S—, —C ( ⁇ O) —, —CO—, —NR—, —CONR. —, —OC—, —SO—, —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 divalent linking group is preferably an alkylene group.
  • the alkylene group may be linear, branched or cyclic.
  • the alkylene group preferably has 1 to 30 carbon atoms, more preferably 1 to 20, more preferably 5 to 20, and particularly preferably 5 to 10.
  • a methylene group, ethylene group, propylene group, butylene group, hexylene group, hepsylene group, cyclopentenylene group, cyclohexylene group and the like are preferable.
  • the number of carbon atoms of the arylene group is preferably 6 to 30, more preferably 6 to 18, and still more preferably 6 to 12.
  • the arylene group is preferably a phenylene group or a naphthalene group.
  • Rtp 7 represents a hydrogen atom, an alkyl group, an aryl group, a group having a crosslinkable group or NRtp 71 Rtp 72 , preferably a hydrogen atom or NRtp 71 Rtp 72, and more preferably NRtp 71 Rtp 72 preferable.
  • 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, but is preferably linear or branched.
  • the alkyl group is preferably unsubstituted. 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.
  • substituents that the aryl group may have include the substituents mentioned in the section of the substituent group A described later.
  • the group having a crosslinkable group has the same meaning as the group having a crosslinkable group in Rtp 1 to Rtp 4 in the general formula (TP1) described above, and the preferred range is also the same.
  • 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 carboxyl group, or a sulfo group is preferable, and a linear chain having 1 to 5 carbon atoms is preferable.
  • a branched alkyl group, an alkenyl group having 1 to 5 carbon atoms, a phenyl group, a group having a crosslinkable group, or a carboxyl 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.
  • the group having a crosslinkable group has the same meaning as the group having a crosslinkable group in Rtp 1 to Rtp 4 in the general formula (TP1) described above, and the preferred range is also the same.
  • 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 to 2, more preferably 0 or 1.
  • Rtp 1 to Rtp 4 each independently represent a hydrogen atom, an alkyl group, an aryl group, or a group having a crosslinkable group, and have the same meaning as Rtp 1 to Rtp 4 in general formula (TP1).
  • the preferred range is also the same.
  • the group having a crosslinkable group has the same meaning as the group having a crosslinkable group in Rtp 1 to Rtp 4 in the general formula (TP1) described above, and the preferred range is also the same.
  • 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 exemplified in the section of Substituent Group A described later can be used.
  • Rtp 9 is preferably an alkyl group, an alkoxy group, or a halogen atom.
  • 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 a group having a substituent or a crosslinkable group 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.
  • the group having a crosslinkable group has the same meaning as the group having a crosslinkable group in Rtp 1 to Rtp 4 in the general formula (TP1) described above, and the preferred range is also the same.
  • a, b and c each independently represent an integer of 0 to 4, and a and b preferably represent 0 or 1, and more preferably represent 0.
  • c preferably represents 0 to 2, more preferably 0.
  • cations are present in a delocalized manner as follows, and the following structures are synonymous, and all of them are included in the present invention.
  • the cation moiety may be at any position in the molecule, but is preferably located on the nitrogen atom. When substituted on a nitrogen atom, the color tends to be further improved.
  • Substituents include halogen atoms, alkyl groups, cycloalkyl groups, alkenyl groups, cycloalkenyl groups, alkynyl groups, aryl groups, heterocyclic groups, cyano groups, hydroxyl groups, nitro groups, carboxyl groups, alkoxy groups, aryloxy groups Silyloxy group, heterocyclic oxy group, acyloxy group, carbamoyloxy group, amino group (including alkylamino group and anilino group), acylamino group, aminocarbonylamino group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfa Moylamino group, alkyl or arylsulfonylamino group, mercapto group, alkylthio group, arylthio group, heterocyclic thio group, sulfamoyl group, sulfo group, alkyl or arylsulfony
  • a halogen atom for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom
  • a linear or branched alkyl group a linear or branched substituted or unsubstituted alkyl group, preferably an alkyl group having 1 to 30 carbon atoms
  • a cycloalkyl group preferably substituted with 3 to 30 carbon atoms or Examples thereof include unsubstituted cycloalkyl groups such as cyclohexyl and cyclopentyl, and polycycloalkyl groups such as bicycloalkyl groups (preferably substituted or unsubstituted bicycloalkyl groups having 5 to 30 carbon atoms
  • Linear or branched alkenyl group (straight or branched substituted or unsubstituted alkenyl group, preferably an alkenyl group having 2 to 30 carbon atoms, such as vinyl, allyl, prenyl, geranyl, oleyl), cycloalkenyl A group (preferably a substituted or unsubstituted cycloalkenyl group having 3 to 30 carbon atoms such as 2-cyclopenten-1-yl and 2-cyclohexen-1-yl, and a polycycloalkenyl group such as bicyclo An alkenyl group (preferably a substituted or unsubstituted bicycloalkenyl group having 5 to 30 carbon atoms such as bicyclo [2,2,1] hept-2-en-1-yl, bicyclo [2,2,2] Octo-2-en-4-yl) and tricycloalkenyl groups, with monocyclic cycloalkenyl groups being particularly preferred.
  • Cycloalkenyl group (preferably a substituted or unsubstituted alkynyl group having 2 to 30 carbon atoms, e.g., ethynyl, propargyl, trimethylsilylethynyl group),
  • An aryl group preferably a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, such as phenyl, p-tolyl, naphthyl, m-chlorophenyl, o-hexadecanoylaminophenyl
  • a heterocyclic group preferably 5 to 7-membered substituted or unsubstituted, saturated or unsaturated, aromatic or non-aromatic, monocyclic or condensed heterocyclic group, more preferably the ring-constituting atom is selected from carbon atom, nitrogen atom and sulfur atom
  • a heterocyclic group having at least one hetero atom of any one of a nitrogen atom, an oxygen atom and a sulfur atom more preferably a 5- or 6-membered aromatic heterocyclic group having 3 to 30 carbon atoms
  • alkoxy group preferably a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms such as methoxy, ethoxy, isopropoxy, tert-butoxy, n-octyloxy, 2-methoxyethoxy
  • aryloxy group preferably Is a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, such as phenoxy, 2-methylphenoxy, 2,4-di-tert-amylphenoxy, 4-tert-butylphenoxy, 3-nitrophenoxy, 2-tetradecanoylaminophenoxy
  • silyloxy group preferably a silyloxy group having 3 to 20 carbon atoms, such as trimethylsilyloxy, tert-butyldimethylsilyloxy
  • a heterocyclic oxy group preferably having a carbon number of 2 to 30 substituted or unsubstituted heterocyclic oxy groups , Heterocyclic portion is preferably described
  • An acyloxy group (preferably a formyloxy group, a substituted or unsubstituted alkylcarbonyloxy group having 2 to 30 carbon atoms, a substituted or unsubstituted arylcarbonyloxy group having 6 to 30 carbon atoms, such as formyloxy, acetyloxy , Pivaloyloxy, stearoyloxy, benzoyloxy, p-methoxyphenylcarbonyloxy), a carbamoyloxy group (preferably a substituted or unsubstituted carbamoyloxy group having 1 to 30 carbon atoms such as N, N-dimethylcarbamoyloxy, N, N-diethylcarbamoyloxy, morpholinocarbonyloxy, N, N-di-n-octylaminocarbonyloxy, Nn-octylcarbamoyloxy), an alkoxycarbonyloxy group (preferably a substituent having 2
  • amino group preferably an amino group, a substituted or unsubstituted alkylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylamino group having 6 to 30 carbon atoms, or a heterocyclic amino group having 0 to 30 carbon atoms
  • amino, methylamino, dimethylamino, anilino, N-methyl-anilino, diphenylamino, N-1,3,5-triazin-2-ylamino acylamino group (preferably formylamino group, carbon number A substituted or unsubstituted alkylcarbonylamino group having 1 to 30 carbon atoms, a substituted or unsubstituted arylcarbonylamino group having 6 to 30 carbon atoms, such as formylamino, acetylamino, pivaloylamino, lauroylamino, benzoylamino, 3, 4,5-tri-n-oc
  • Aryloxycarbonylamino group (preferably a substituted or unsubstituted aryloxycarbonylamino group having 7 to 30 carbon atoms, such as phenoxycarbonylamino, p-chlorophenoxycarbonylamino, mn-octyloxyphenoxycarbonylamino)
  • Sulfamoylamino group (preferably a substituted or unsubstituted sulfamoylamino group having 0 to 30 carbon atoms such as sulfamoylamino, N, N-dimethylaminosulfonylamino, Nn-octylamino Sulfonylamino), alkyl or arylsulfonylamino group (preferably substituted or unsubstituted alkylsulfonylamino group having 1 to 30 carbon atoms, substituted or unsubstituted arylsulfonylamino group having 6 to 30 carbon atom
  • alkylthio group preferably a substituted or unsubstituted alkylthio group having 1 to 30 carbon atoms such as methylthio, ethylthio, n-hexadecylthio
  • arylthio group preferably a substituted or unsubstituted arylthio group having 6 to 30 carbon atoms
  • the heterocyclic portion described in the above is preferably, for example, 2-benzothiazolylthio, 1-phenyltetrazol-5-ylthio), a sulfamoyl group (preferably a substituted or unsubstituted sulfamoyl group having 0 to 30 carbon atoms, N-ethylsulfamoyl, N- (3-dodecyloxypropyl) sulfur Moil, N, N- dimethylsulfamoyl, N- acetyl sulfamoyl, N- benzoylsulfamoyl, N- (
  • alkyl or arylsulfinyl group preferably a substituted or unsubstituted alkylsulfinyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfinyl group having 6 to 30 carbon atoms, such as methylsulfinyl, ethylsulfinyl, phenylsulfinyl, p-methylphenylsulfinyl
  • an alkyl or arylsulfonyl group preferably a substituted or unsubstituted alkylsulfonyl group having 1 to 30 carbon atoms, a substituted or unsubstituted arylsulfonyl group having 6 to 30 carbon atoms, such as methylsulfonyl , Ethylsulfonyl, phenylsulfonyl, p-methylphenylsulfonyl
  • alkoxycarbonyl group preferably a substituted or unsubstituted alkoxycarbonyl group having 2 to 30 carbon atoms such as methoxycarbonyl, ethoxycarbonyl, tert-butoxycarbonyl, n-octadecyloxycarbonyl
  • a carbamoyl group preferably having a carbon number 1-30 substituted or unsubstituted carbamoyl such as carbamoyl, N-methylcarbamoyl, N, N-dimethylcarbamoyl, N, N-di-n-octylcarbamoyl, N- (methylsulfonyl) carbamoyl), aryl or hetero
  • a ring azo group preferably a substituted or unsubstituted arylazo group having 6 to 30 carbon atoms, a substituted or unsubstituted heterocyclic azo group having 3 to 30 carbon atoms (the heterocycle portion is the heterocycle
  • a phosphinyloxy group (preferably a substituted or unsubstituted phosphinyloxy group having 2 to 30 carbon atoms, such as diphenoxyphosphinyloxy, dioctyloxyphosphinyloxy), a phosphinylamino group ( Preferably, it is a substituted or unsubstituted phosphinylamino group having 2 to 30 carbon atoms, for example, dimethoxyphosphinylamino, dimethylaminophosphinylamino), a silyl group (preferably a substitution having 3 to 30 carbon atoms) Or, an unsubstituted silyl group, for example, trimethylsilyl, tert-butyldimethylsilyl, phenyldimethylsilyl).
  • the dye cation is preferably represented by the general formula (A1) or the general formula (A2).
  • General formula (A1) In the general formula (A1), Ar + independently represents a triarylmethane dye structure, L 1 represents a group connecting two or more Ar + , n1 represents an integer of 1 to 20, and m represents 0 Or represents 1; when n1 represents 1, m represents 0.
  • Ar + represents a triarylmethane dye structure, which is synonymous with the above-described triarylmethane dye structure, and the preferred range is also the same.
  • the triarylmethane dye structure is represented by the general formula (TP1)
  • the bonding position between the triarylmethane dye structure and L 1 is any one of Rtp 1 to Rtp 8 , Rtp 71 and Rtp 72 , and Rtp 71 or it is preferably Rtp 72.
  • the bonding position between the triarylmethane dye structure and L 1 is any one of Rtp 1 to Rtp 6 and Rtp 9 to Rtp 11 , (Rtp 9 to Rtp 11 ) is preferable.
  • L 1 represents a group linking two or more Ar + .
  • L 1 is a divalent or higher valent linking group, and is preferably a divalent to hexavalent linking group.
  • L 1 is a hydrocarbon group, a heterocyclic group, —O—, —S—, —CO—, —NR—, —CONR—, —OC—, —SO—, or a group obtained by combining two or more thereof.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • the hydrocarbon group may be an aliphatic hydrocarbon group or an aromatic hydrocarbon group.
  • the hydrocarbon group may be linear, branched or cyclic.
  • the hydrocarbon group preferably has 1 to 30 carbon atoms, more preferably 1 to 18 carbon atoms, and still more preferably 1 to 12 carbon atoms.
  • the hydrogen atom contained in the hydrocarbon group may be substituted with a halogen atom.
  • a fluorine atom is preferable.
  • the hydrocarbon group is an aliphatic hydrocarbon group, the carbon number is preferably 1-20, and more preferably 1-10.
  • the hydrocarbon group is an aromatic hydrocarbon group, the carbon number is preferably 6 to 24 and more preferably 6 to 12.
  • the heterocyclic group preferably contains a nitrogen atom as a hetero atom.
  • the heterocyclic group is preferably a 3- to 8-membered ring, more preferably a 6-membered ring.
  • L 1 is preferably a group consisting of an aliphatic hydrocarbon group having 1 to 30 carbon atoms, an aromatic hydrocarbon group having 1 to 30 carbon atoms, or a combination thereof.
  • L 1 represents a divalent linking group
  • an alkylene group having 1 to 30 carbon atoms methylene group, ethylene group, trimethylene group, propylene group, butylene group, etc.
  • an arylene group having 6 to 30 carbon atoms phenylene) Group, naphthalene group, etc.
  • heterocyclic group —CH ⁇ CH—, —O—, —S—, —CO—, —NR—, —CONR—, —OC—, —SO—, or 2 of these
  • a combined linking group as described above is preferred.
  • R represents a hydrogen atom, an alkyl group, an aryl group, or a heterocyclic group each independently.
  • the alkylene group having 1 to 30 carbon atoms preferably has 1 to 20 carbon atoms, and more preferably 1 to 10 carbon atoms.
  • examples of the substituent include a halogen atom.
  • the heterocyclic group preferably contains a nitrogen atom as a hetero atom.
  • the heterocyclic group is preferably a 3- to 8-membered ring, more preferably a 6-membered ring.
  • the carbon number of the arylene group having 6 to 30 carbon atoms is preferably 6 to 24, and more preferably 6 to 12.
  • L 1 preferably contains a cyclic aliphatic hydrocarbon group or aromatic group.
  • the number of carbon atoms in the cyclic aliphatic hydrocarbon group is preferably 3 to 8, and more preferably 4 to 6.
  • the aromatic group may be an aromatic hydrocarbon group or an aromatic heterocyclic group.
  • the aromatic group preferably has 6 to 12 carbon atoms, more preferably 6 to 10 carbon atoms.
  • the binding site between L 1 and Ar + preferably does not contain a conjugated system.
  • a conjugated system at the binding site between L 1 and Ar + By not including a conjugated system at the binding site between L 1 and Ar + , the formation of a conjugated system between Ar + and L 1 can be suppressed, and the hue of the triarylmethane dye changes. Can be effectively suppressed.
  • the formula weight of the L 1 moiety in one molecule of the dye cation is preferably 14 to 800, more preferably 50 to 200.
  • L 1 include the following structures, but the present invention is not limited to these.
  • * represents a connecting site with Ar + in the general formula (A1), and a represents an integer of 1 or more.
  • n1 represents an integer of 1 to 20, preferably an integer of 1 to 6, more preferably an integer of 2 to 4, and further preferably 2 or 3.
  • Ar + independently represents a triarylmethane dye structure
  • L 2 represents a divalent linking group
  • L 3 represents a divalent linking group
  • q represents an integer of 1 to 18 Represents.
  • Ar + represents a triarylmethane dye structure, and is synonymous with Ar + in General Formula (A1), and the preferred range is also the same.
  • L 2 represents a divalent linking group, which is synonymous with the case where L 1 in General Formula (A1) represents a divalent linking group, and the preferred range is also the same.
  • L 3 represents a divalent linking group, which is synonymous with the case where L 1 in General Formula (A1) represents a divalent linking group, and the preferred range is also the same.
  • q represents an integer of 1 to 18, preferably an integer of 1 to 10, and more preferably an integer of 1 to 3.
  • the molecular weight of the dye cation is preferably 1,000 to 10,000, and more preferably 1,000 to 5,000.
  • the divalent or higher anion may exist as a separate molecule without being bonded to the dye cation via a covalent bond, or may be present in the same molecule as the dye cation.
  • the divalent or higher valent anion constituting the salt compound of the present invention is not particularly defined, but is —SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , a group containing a structure represented by the following general formula (B2) And preferably contains at least one selected from the group containing the structure represented by the following general formula (B3), more preferably a group containing the structure represented by —SO 3 — and / or the general formula (B2). preferable.
  • the divalent or higher anion preferably has a fluorine atom.
  • the salt compound of the present invention may contain only one kind of divalent or more anions, or may contain two or more kinds.
  • R 11 and R 12 are independently - represents or -CO-, at least one of R 11 and R 12 -SO 2 - is preferable to represent, R 11 and R More preferably, both of 12 represent —SO 2 —.
  • 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.
  • R 13 represents —SO 2 — or —CO—
  • R 14 and R 15 each independently represents —SO 2 —, —CO— or —CN.
  • R 13 ⁇ R 15 -SO 2 - - in the general formula (B3) at least one of R 13 ⁇ R 15 -SO 2 more preferably represents.
  • the group containing the structure represented by the general formula (B3) preferably has a fluorine-substituted alkyl group at least at any terminal of R 13 to R 15 in the general formula (B3), and R 13 to R 15 More preferably, at least one of the above is directly bonded to the fluorine-substituted alkyl group.
  • a fluorine-substituted alkyl group at at least two terminals of R 13 to R 15 .
  • a fluorine-substituted alkyl group is synonymous with what was demonstrated with group containing the structure represented by general formula (B2), and its preferable range is also the same.
  • the divalent or higher anion is preferably an anion represented by the following general formula (B1).
  • General formula (B1) In the general formula (B1), k is an integer of 2-20; the A represents a divalent linking group; representing R is 2 ⁇ k-valent organic group; p represents 0 or 1 X - is , —SO 3 ⁇ , —COO ⁇ , —PO 4 ⁇ , a group containing a structure represented by the general formula (B2) or a group containing a structure represented by the general formula (B3).
  • R represents a k-valent organic group, and examples thereof include the following organic groups (a) to (e). Among these, the organic group (a) or (c) is preferable.
  • A a substituted or unsubstituted non-aromatic hydrocarbon group
  • b a group in which a plurality of substituted or unsubstituted non-aromatic hydrocarbon groups are linked by a divalent linking group containing a hetero atom
  • c substituted or unsubstituted
  • An unsubstituted aromatic hydrocarbon group (d) a group in which two substituted or unsubstituted aromatic hydrocarbon groups are linked by a divalent linking group containing a hetero atom or a divalent non-aromatic hydrocarbon group ( e) substituted or unsubstituted heterocyclic group
  • the non-aromatic hydrocarbon group in the organic group (a) is preferably an aliphatic hydrocarbon group, which may be linear, branched or cyclic. In particular, an alkylene group having 1 to 10 carbon atoms is preferable.
  • the substituent is preferably a halogen atom (particularly a fluorine atom). Examples of the case where the non-aromatic hydrocarbon group has a substituent include an alkylene group having 1 to 10 carbon atoms substituted with a fluorine atom.
  • the number of atoms constituting the non-aromatic hydrocarbon group in (a) is preferably 1 to 40, and more preferably 1 to 20. Specific examples of the organic group (a) include the following, but the present invention is not limited thereto.
  • * represents a linking site with A or X ⁇ in the general formula (B1).
  • the non-aromatic hydrocarbon group in the organic group (b) is preferably an aliphatic hydrocarbon group, and may be linear, branched or cyclic.
  • the substituent include a polymerizable group (for example, a (meth) acryloyl group, a vinyl group).
  • the hetero atom include an oxygen atom, a nitrogen atom, and a sulfur atom.
  • the divalent linking group containing a hetero atom is preferably —O—, —N—, —S—, —CO—, or a group comprising a combination of these with an alkylene group.
  • the number of atoms constituting the organic group (b) is preferably 6 to 100, more preferably 8 to 60.
  • Specific examples of the (b) non-aromatic hydrocarbon group include the following, but the present invention is not limited thereto.
  • * represents a linking site with A or X ⁇ in the general formula (B1).
  • the aromatic hydrocarbon group in the organic group (c) is preferably an arylene group.
  • the number of carbon atoms in the arylene group is preferably 6-18, and more preferably 6-12.
  • the aromatic hydrocarbon group may be monocyclic or polycyclic.
  • the number of atoms constituting the organic group (c) is preferably 6 to 60, more preferably 6 to 30.
  • Specific examples of the organic group (c) include the following, but the present invention is not limited thereto.
  • * represents a linking site with A or X ⁇ in the general formula (B1).
  • the aromatic hydrocarbon group in the organic group (d) has the same meaning as the aromatic hydrocarbon group (c).
  • Examples of the hetero atom constituting the divalent linking group containing a hetero atom in the organic group (d) include an oxygen atom, a nitrogen atom, and a sulfur atom.
  • the bivalent coupling group containing a hetero atom is synonymous with the bivalent coupling group containing the hetero atom in the organic group of the said (b).
  • Examples of the divalent non-aromatic hydrocarbon group include the non-aromatic hydrocarbon group in the organic group (a).
  • the number of atoms constituting the organic group (d) is preferably 6 to 60, and more preferably 6 to 50. Specific examples of the organic group (d) include the following, but the present invention is not limited thereto.
  • * represents a linking site with A or X ⁇ in the general formula (B1).
  • the heterocyclic group in the organic group (e) may be an aromatic heterocyclic group or a non-aromatic heterocyclic group.
  • the hetero atom contained in the heterocyclic group is preferably a nitrogen atom.
  • the heterocyclic group is preferably a 3- to 8-membered ring, more preferably a 4- to 6-membered ring.
  • the number of carbon atoms constituting the heterocyclic group is preferably 2-6.
  • the number of atoms constituting the organic group of (e) is preferably 6 to 50, more preferably 6 to 30.
  • Specific examples of the organic group (e) include the following, but the present invention is not limited thereto.
  • * represents a linking site with A or X ⁇ in the general formula (B1).
  • the divalent linking group represented by A is an alkylene group, an arylene group, a heterocyclic group, —CH ⁇ CH—, —O—, —S—, —C ( ⁇ O) —. , —CO—, —NR—, —CONR—, —OC—, —SO—, —SO 2 — and a combination of two or more thereof are preferred.
  • divalent or higher anions are listed below, but are not limited thereto.
  • the weight average molecular weight (Mw) of the salt compound used in the present invention is preferably 1,000 or more and 10,000 or less, more preferably 1,000 or more and 7,500 or less, and particularly preferably 1,000 or more and 6,000 or less. .
  • Mw weight average molecular weight
  • the solvent solubility of the salt compound can be further improved by setting Mw to 10,000 or less.
  • electrical characteristics can be made more favorable by setting Mw to 1,000 or more.
  • the content of the salt compound in the composition of the present invention is preferably 10 to 60% by mass and more preferably 10 to 40% by mass with respect to the total solid content of the composition of the present invention.
  • the salt compound may be used alone or in combination of two or more.
  • the coloring composition of this invention contains the solvent which melt
  • the solubility of the salt compound in the solvent is preferably 3.0% by mass or more at 25 ° C., more preferably 5.0% by mass or more.
  • the upper limit of the solubility of the salt compound in the solvent is usually 50% by mass or less at 25 ° C.
  • the solubility of the salt compound in the solvent satisfies the above range, the storage stability when the colored composition is formed, and the precipitation of the dye during the color filter preparation step can be more effectively suppressed.
  • organic solvents such as esters, ethers, ketones, and aromatic hydrocarbons are preferable from the viewpoint of use in resists for color filters.
  • esters include ethyl acetate, n-butyl acetate, isobutyl acetate, amyl formate, isoamyl acetate, isobutyl acetate, butyl propionate, isopropyl butyrate, ethyl butyrate, butyl butyrate, methyl lactate, ethyl lactate, alkyl oxyacetate (Examples: methyl oxyacetate, ethyl oxyacetate, butyl oxyacetate (specific examples include methyl methoxyacetate, ethyl methoxyacetate, butyl methoxyacetate, methyl ethoxyacetate, ethyl ethoxyacetate)), 3- Oxypropionic acid alkyl esters, 2-oxypropionic acid alkyl esters, methyl 2-oxy-2-methylpropionate, ethyl 2-oxy-2-methylpropionate, methyl pyruvate, ethyl
  • ethers include diethylene glycol dimethyl ether, cyclohexyl acetate, tetrahydrofuran, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, methyl cellosolve acetate, ethyl cellosolve acetate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, diethylene glycol ethyl methyl.
  • examples include ether, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monopropyl ether acetate and the like.
  • ketones examples include methyl ethyl ketone, cyclohexanone, 2-heptanone, and 3-heptanone.
  • aromatic hydrocarbons include toluene and xylene.
  • Solvents satisfying the requirement of dissolving 1.0% by mass or more of the salt compound at 25 ° C. and preferable as a coloring composition for a color filter include methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, and ethyl.
  • a mixed solvent composed of two or more of the above-mentioned solvents is preferable, and diethylene glycol ethyl methyl ether and propylene glycol methyl ether acetate are more preferable.
  • the content of the solvent for dissolving the salt compound in an amount of 1.0% by mass or more at 25 ° C. is preferably such that the total solid concentration in the composition of the present invention is 10 to 30% by mass, and is 10 to 20% by mass. Is more preferred. Only 1 type may be used for the said salt compound which melt
  • the composition of the present invention contains at least one purple colorant selected from a xanthene dye, a pyromethene dye and a tetraazaporphyrin dye together with the salt compound.
  • the purple colorant is preferably dissolved in a solvent capable of dissolving the salt compound at 25 ° C. by 1.0% by mass or more.
  • the total amount of the purple colorant in the composition of the present invention is preferably 1 to 90% by mass and more preferably 5 to 80% by mass with respect to the total amount of the salt compound.
  • the purple colorant may be used alone or in combination of two or more.
  • xanthene dyes, pyromethene dyes, and tetraazaporphyrin dyes will be described.
  • a xanthene pigment is a dye containing a compound having a xanthene skeleton in the molecule.
  • the xanthene dye is preferably dissolved in an organic solvent.
  • the solubility of the xanthene dye in propylene glycol monomethyl ether acetate is preferably 1% by mass or more, and more preferably 3% by mass or more.
  • a dye containing a compound represented by the general formula (I-1a) (hereinafter sometimes referred to as “compound (1a)”) is preferable.
  • Compound (1a) may be a tautomer thereof.
  • the content of the compound (1a) in the xanthene dye 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 dye.
  • R 1 to R 4 each independently represent a hydrogen atom, a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms.
  • —CH 2 — contained in the saturated hydrocarbon group may be 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.
  • R 3 and R 4 may combine with 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. when m1 is 2 or more, the plurality of R 5 may be the same or different;
  • m2 and m3 each independently represents an integer of 0 to 3.
  • R 6 and R 7 may be independently the same or different; a represents 0 or 1; when a represents 0, any group in the xanthene dye structure contains 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 —NR 8 —, and R 9 and R 10 may be bonded to each other to form a 3- to 10-membered heterocyclic ring containing
  • 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-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.
  • N + (R 11) 4 are preferred.
  • R 1 to R 4 are these groups, a color filter with less generation of foreign matter and excellent heat resistance can be formed from the colored composition of the present invention containing the compound (1a).
  • 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.
  • 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, and among the alkyl groups mentioned as the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms described above, 1 to 6 carbon atoms Of the alkyl group.
  • n2 and m3 each independently represents an integer of 0 to 3, with 0 being preferred.
  • 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 5A preferably contains an anion
  • X ⁇ is contained depending on the valence of the cation contained in the xanthene dye represented by the general formula (I-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.
  • Examples of 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. When N + (R 11 ) 4 is present in the compound (1a), R 11 is any of these groups, so that the color composition containing the compound (1a) has less foreign matter from the colored composition of the present invention. A filter can be formed.
  • the xanthene dye represented by the general formula (I-1a) has a cation that is delocalized as follows, and the following structures are synonymous, and both are included in the present invention. To do.
  • the cation moiety may be at any position in the molecule, but is preferably located on the nitrogen atom.
  • R 21 to R 24 are each independently a hydrogen atom, —R 26 or a monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms which may have a substituent. Represents. R 21 and R 22 may be bonded to each other to form a ring containing a nitrogen atom, and R 23 and R 24 may be bonded to each other to form a ring containing a nitrogen atom.
  • R 25 is, -SO 3 - represents a Z 1+ or -SO 2 NHR 26 -, - SO 3 H, -SO 3.
  • m4 represents an integer of 0 to 5. When m4 is 2 or more, the plurality of R 25 may be the same or different.
  • a1 represents an integer of 0 or 1. when a represents 0, any group in the xanthene dye structure contains an anion;
  • X1 ⁇ represents an anion.
  • R 26 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms.
  • Z 1+ represents + N (R 27 ) 4 , Na + or K + , and four R 27 s may be the same or different.
  • R 27 represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms or a benzyl group.
  • the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms in R 21 to R 24 has the same meaning as the aromatic hydrocarbon group represented by R 1 to R 4 in formula (I-1a). is there. Hydrogen atoms contained in the monovalent aromatic hydrocarbon group having 6 to 10 carbon atoms, -SO 3 -, -SO 3 H , -SO 3 - Z 1+, -SO 3 R 26 or -SO 2 NHR 26 May be substituted.
  • R 21 to R 24 As a combination of R 21 to R 24 , R 21 and R 23 are hydrogen atoms, R 22 and R 24 are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and the above aromatic hydrocarbons hydrogen atoms contained in the groups, -SO 3 -, -SO 3 H , -SO 3 - Z 1+, what is preferably substituted by -SO 3 R 26 or -SO 2 NHR 26.
  • R 21 and R 23 are hydrogen atoms
  • R 22 and R 24 are monovalent aromatic hydrocarbon groups having 6 to 10 carbon atoms, and hydrogen contained in the aromatic hydrocarbon group. atom, -SO 3 - in which are substituted with Z 1+ or -SO 2 NHR 26.
  • Examples of the ring containing a nitrogen atom formed by combining R 21 and R 22 with each other and the ring containing a nitrogen atom formed by combining R 23 and R 24 with each other include R in the general formula (I-1a). Examples of the ring formed by combining 1 and R 2 with each other include aliphatic heterocyclic rings. Examples of the aliphatic heterocycle include the following.
  • the monovalent saturated hydrocarbon group having 1 to 20 carbon atoms in R 26 and R 27 has the same meaning as the saturated hydrocarbon group described in R 8 to R 11 .
  • R 21 ⁇ R 24 represents -R 26, -R 26 each independently is preferably a methyl group or an ethyl group.
  • R 26 in -SO 3 R 26 and -SO 2 NHR 26 preferably branched alkyl group having 3 to 20 carbon atoms, more preferably a branched alkyl group having 6-12 carbon atoms, More preferred is a 2-ethylhexyl group.
  • R 26 is such a group, a color filter with less generation of foreign matters can be formed from the colored composition of the present invention containing the compound (2a).
  • a1 represents 0 or 1, and when a1 represents 0, any group in the xanthene dye structure preferably has an anion, and R 25 preferably contains an anion.
  • X1 ⁇ is contained depending on the valence of the cation contained in the xanthene dye represented by the general formula (I-2a), and is usually monovalent or divalent, and preferably monovalent.
  • Anion X - is the general formula of (I-1a) X - in the above formula, the preferable range is also the same.
  • Z 1+ is + N (R 27 ) 4 , Na + or K + , preferably + N (R 27 ) 4 .
  • R 27 is preferably monovalent saturated hydrocarbon groups having 5 to 20 carbon atoms. Further, the total number of carbon atoms of the four R 27 is preferably 20 to 80, and more preferably 20 to 60.
  • + N (R 27 ) 4 is present in the compound (2a)
  • R 27 is any of these groups
  • the color composition of the present invention containing the compound (2a) produces less foreign matter.
  • m4 is preferably 1 to 4, and more preferably 1 or 2.
  • compound (3a) a compound represented by the general formula (I-3a) (hereinafter sometimes referred to as “compound (3a)”) is also preferable.
  • 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 formula (1a). )
  • the monovalent saturated hydrocarbon group having 1 to 10 carbon atoms in R 31 and R 32 is the number of carbon atoms among the monovalent saturated hydrocarbon groups having 1 to 10 carbon atoms described for R 8 in formula (1a). Examples thereof include 1 to 10 monovalent saturated hydrocarbon groups. 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 formula (1a). It is done.
  • 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 alkylsulfanyl group having 1 to 4 carbon atoms in R 33 and R 34 include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, a butylsulfanyl group, and an isopropylsulfanyl group.
  • 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, and preferably 0 or 1.
  • Examples of the compound (1a) include compounds represented by the compounds (1-1) to (1-43).
  • R represents a monovalent saturated hydrocarbon group having 1 to 20 carbon atoms, preferably a branched alkyl group having 6 to 12 carbon atoms, and more preferably a 2-ethylhexyl group.
  • xanthene dyes examples include C.I. I. Acid Red 51 (hereinafter, the description of CI Acid Red is omitted and only the number is described. Others are also the same), 52, 87, 92, 94, 289, 388, C.I. I. Acid Violet 9, 30, 102, C.I. I. Basic Red 1 (Rhodamine 6G), 2, 3, 4, 8, C.I. I. Basic Red 10 (Rhodamine B), 11, C.I. I. Basic violet 10, 11, 25, C.I. I. Solvent Red 218, C.I. I. Modern Tread 27, C.I. I.
  • xanthene dyes described in JP 2010-32999 A xanthene dyes described in Japanese Patent No. 4492760, and the like.
  • the xanthene pigment commercially available xanthene dyes (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.
  • xanthene dye Only one type of xanthene dye may be used, or two or more types may be used in combination. When two or more kinds of xanthene dyes are used in combination, the total amount preferably satisfies the above range.
  • the pyromethene dye is preferably a dipyrromethene metal complex compound in which the compound represented by the general formula (I) is coordinated to a metal atom or a metal compound.
  • R 1 , R 2 , R 3 , R 4 , R 5 and R 6 each independently represent a hydrogen atom or a monovalent substituent.
  • R 7 represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group or a heterocyclic group.
  • R 1 to R 6 represent a monovalent substituent
  • examples of the monovalent substituent include the substituents in the substituent group A described above.
  • the monovalent substituent is a further substitutable group, it may be further substituted with any of the groups described above.
  • 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 a 5-membered, 6-membered or 7-membered member.
  • a ring may be formed. Examples of 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 5-membered, 6-membered and 7-membered rings formed are further substitutable groups, they may be substituted with any of the above-mentioned substituent group A, and two or more substituents In the case where the substituent is substituted, the substituents may be the same or different.
  • the preferred range of R 7 in the general formula (II) is synonymous with the case where R 1 to R 6 are a halogen atom, an alkyl group, an aryl group or a heterocyclic group, and the preferred range is also the same.
  • 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 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.
  • examples of the heterocyclic group include 2-thienyl group, 4-pyridyl group, 3-pyridyl group, 2-pyridyl group, 2-furyl group, 2-pyrimidinyl group, 2 -A benzothiazolyl group, 1-imidazolyl group, 1-pyrazolyl group or benzotriazol-1-yl group is preferred, and a 2-thienyl group, 4-pyridyl group, 2-furyl group, 2-pyrimidinyl group or 1-pyridyl group is more preferred. 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.
  • R 1 and R 6 are each independently a hydrogen atom, alkyl group, alkenyl group, aryl group, heterocyclic group, silyl group, hydroxyl group, cyano group, alkoxy group, aryloxy Group, heterocyclic oxy group, acyl group, alkoxycarbonyl group, carbamoyl group, amino group, anilino group, heterocyclic amino group, carbonamido group, ureido group, imide group, alkoxycarbonylamino group, aryloxycarbonylamino group, sulfone An amide group, an azo group, an alkylthio group, an arylthio group, a heterocyclic thio group, an alkylsulfonyl group, an aryls
  • R 1 and R 6 are each independently a hydrogen atom, alkyl group, alkenyl group, aryl group, heterocyclic group, cyano group, acyl group, alkoxycarbonyl group, carbamoyl group, amino group.
  • R 2 and R 5 are each independently an alkyl group, alkenyl group, aryl group, heterocyclic group, cyano group, nitro group, acyl group, alkoxycarbonyl group, aryloxycarbonyl group, carbamoyl group, imide group , Alkylsulfonyl group, arylsulfonyl group, or sulf Represented by moil group
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, a cyano group, an acyl group,
  • a preferred embodiment of the dipyrromethene metal complex compound in which the compound represented by the general formula (II) is coordinated to a metal atom or a metal compound is represented by the following general formula (II-1), (II-2) or (II-3) It is a complex compound represented by these.
  • 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.
  • Ma represents a metal atom or a metal compound,
  • X 1 represents a group capable of binding to Ma, and
  • X 2 represents a group necessary for neutralizing the charge of Ma.
  • X 1 and X 2 may be bonded to each other to form a 5-membered, 6-membered or 7-membered ring.
  • R 1 ⁇ R 6 in the general formula (II-1), general formula (II) in the same meaning as R 1 ⁇ R 6, and preferable embodiments thereof are also the same.
  • Ma in the general formula (II-1) represents a metal atom or a metal compound, and the metal atom or metal compound in the “complex in which the compound represented by the general formula (II) is coordinated to the metal atom or metal compound” It is synonymous and the preferable range is also the same.
  • R 7 in the general formula (II-1) has the same meaning as R 7 in formula (II), preferable embodiments thereof are also the same.
  • X 1 in the general formula (II-1) may be any group capable of binding to Ma, such as water, alcohols (for example, methanol, ethanol, propanol), and the like, and “metal chelate” [ 1] Groups derived from the compounds described in Takeichi Sakaguchi and Keihei Ueno (1995 Nanedou), [2] (1996), [3] (1997), and the like.
  • water, carboxylic acid compounds, alcohols, amine compounds, and amide compounds are preferable from the viewpoint of production, and water, carboxylic acid compounds, and amide compounds are more preferable.
  • X 2 in the general formula (II-1) represents a group necessary for neutralizing the electric charge of Ma, such as a halogen atom (for example, fluorine atom, chlorine atom, bromine atom), hydroxyl group, aliphatic imide A monovalent group derived from (for example, succinimide, maleimide, glutarimide, diacetamide, etc., preferably succinimide, maleimide), an aromatic imide group or a heterocyclic imide (for example, phthalimide, Naphthalimide, 4-bromophthalimide, 4-methylphthalimide, 4-nitrophthalimide, naphthalenecarboximide, tetrabromophthalimide, etc., preferably phthalimide, 4-bromophthalimide, 4-methylphthalimide) Valent groups, aromatic carboxylic acids (eg benzoic acid, 2-methoxy Benzoic acid, 3-methoxybenzoic acid, 4-methoxybenzoic acid, 4-chlorobenzoic
  • 1-benzyl-5-ethoxyhydantoin, 5,5-dimethyl-2,4-oxazolidinedione, 4,5-dicyanoimidazole, diethyl 1H-imidazole-4,5-dicarboxylate) Represents a valent group.
  • a halogen atom, an aliphatic carboxylic acid group, an aromatic carboxylic acid group, an aliphatic imide group, an aromatic imide group, a sulfonic acid group, and a nitrogen-containing ring compound are preferable, and a hydroxyl group and an aliphatic carboxylic acid group An aromatic imide group and a nitrogen-containing ring compound are more preferable.
  • X 1 and X 2 in formula (II-1) are bonded to each other to form a 5-membered, 6-membered, or 7-membered ring with Ma, 5-membered, 6-membered, and 7-membered are formed.
  • the ring may be a saturated ring or an unsaturated ring.
  • the 5-membered, 6-membered, and 7-membered rings are heterocycles having at least one atom selected from a nitrogen atom, an oxygen atom, and a sulfur atom, which may be composed of only carbon and hydrogen atoms. There may be.
  • R 1 to R 13 each independently represents a hydrogen atom or a substituent.
  • R 7 and R 14 each independently represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group.
  • Ma represents a metal atom or a metal compound.
  • R 1 ⁇ R 6 in Formula (II-2), general formula (II) in the same meaning as R 1 ⁇ R 6, and preferable embodiments thereof are also the same.
  • the substituent represented by R 8 to R 13 in the general formula (II-2) has the same meaning as the substituent represented by R 1 to R 6 of the compound represented by the general formula (II), The preferred embodiment is also the same.
  • the substituents represented by R 8 to R 13 of the compound represented by the general formula (I-2) are further substitutable groups, they are not substituted with any of the above-mentioned substituent group A. In the case where it is substituted with two or more substituents, these substituents may be the same or different.
  • R 7 in the formula (II-2) has the same meaning as R 7 in formula (I), preferable embodiments thereof are also the same.
  • R 14 in the general formula (II-2) represents a hydrogen atom, a halogen atom, an alkyl group, an aryl group, or a heterocyclic group, and is synonymous with R 7 in the general formula (II), and the preferred range is also the same. It is.
  • R 14 is a further substitutable group, it may be substituted with any of the aforementioned substituents R, and when it is substituted with two or more substituents, those substituents are They may be the same or different.
  • Ma in the general formula (II-2) represents a metal or a metal compound, and the metal atom or metal compound in the above-mentioned “complex in which the compound represented by the general formula (II) is coordinated to the metal atom or metal compound”
  • the preferred range is also the same.
  • R 8 and R 9 , R 9 and R 10 , R 11 and R 12 , R 12 and R 13 in the general formula (II-2) are each independently bonded to each other to form a 5-membered, 6-membered, or 7-membered compound.
  • a membered saturated ring or an unsaturated ring may be formed.
  • the saturated or unsaturated ring formed is synonymous with the saturated or unsaturated ring formed by R 1 and R 2 , R 2 and R 3 , R 4 and R 5 , and R 5 and R 6. There are also preferred examples.
  • R 2 to R 5 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.
  • R 8 and R 9 each independently represents an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an alkoxy group, an aryloxy group, an alkylamino group, an arylamino group or a heterocyclic amino group.
  • Ma represents a metal atom or a metal compound.
  • X 3 and X 4 each independently represent NRa (Ra represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkylsulfonyl group, or an arylsulfonyl group), an oxygen atom, or Represents a sulfur atom.
  • Ra represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkylsulfonyl group, or an arylsulfonyl group
  • an oxygen atom or Represents a sulfur atom.
  • Y 1 and Y 2 each independently represent NRb (Rb represents a hydrogen atom, an alkyl group, an alkenyl group, an aryl group, a heterocyclic group, an acyl group, an alkylsulfonyl group, or an arylsulfonyl group), an oxygen atom, Represents a sulfur atom or a carbon atom.
  • X 5 represents a group capable of binding to Ma, and a represents 0, 1 or 2.
  • R 8 and Y 1 may be bonded to each other to form a 5-membered, 6-membered, or 7-membered ring, and R 9 and Y 2 are bonded to each other to form a 5-, 6-, or 7-membered ring.
  • the ring may be formed.
  • Formula (II-3) R 2 ⁇ R 5 and R 7 in the general formula (II) in the same meaning as R 2 ⁇ R 5 and R 7, the preferred embodiment is also the same.
  • Ma in the general formula (II-3) represents a metal or a metal compound, and is synonymous with the metal atom or the metal compound in the complex in which the compound represented by the general formula (II) is coordinated to the metal atom or the metal compound.
  • the preferred range is also the same.
  • R 8 and R 9 are each independently an alkyl group (preferably a linear, branched or cyclic alkyl group having 1 to 36 carbon atoms, more preferably 1 to 12 carbon atoms).
  • alkyl group preferably a linear, branched or cyclic alkyl group having 1 to 36 carbon atoms, more preferably 1 to 12 carbon atoms.
  • an alkenyl group preferably an alkenyl group having 2 to 24 carbon atoms, more preferably 2 to 12 carbon atoms, for example, a vinyl group, an allyl group, a 3-buten-1-y
  • an alkyl group, alkenyl group, aryl group, heterocyclic group, alkoxy group, aryloxy group, alkylamino group, arylamino group, or heterocyclic amino group represented by R 8 and R 9 Is a further substitutable group, it may be substituted with any of the above-mentioned substituent group A, and when it is substituted with two or more substituents, these substituents are They may be the same or different.
  • X 3 and X 4 each independently represent NRa, an oxygen atom, or a sulfur atom.
  • Ra is a hydrogen atom, an alkyl group (preferably a linear, branched or cyclic alkyl group having 1 to 36 carbon atoms, more preferably 1 to 12 carbon atoms, such as a methyl group, an ethyl group, a propyl group, an isopropyl group, Butyl group, isobutyl group, tert-butyl group, hexyl group, 2-ethylhexyl group, dodecyl group, cyclopropyl group, cyclopentyl group, cyclohexyl group, 1-adamantyl group), alkenyl group (preferably having 2 to 24 carbon atoms, more Preferably it is an alkenyl group having 2 to 12, for example, a vinyl group, an allyl group, a 3-buten-1-yl group), an aryl
  • Ra when substituted, it may be further substituted with a substituent, and when it is substituted with a plurality of substituents, these substituents may be the same or different.
  • X 3 and X 4 are each independently preferably an oxygen atom or a sulfur atom, and more preferably an oxygen atom.
  • Y 1 and Y 2 each independently represent NRb, a sulfur atom, or a carbon atom, and Rb has the same meaning as Ra in X 3 .
  • Y 1 and Y 2 are preferably each independently NRb (Rb is a hydrogen atom or an alkyl group having 1 to 8 carbon atoms), and Y 1 and Y 2 are particularly preferably both NH.
  • R 8 and Y 1 are bonded to each other, and together with R 8 , Y 1 and the carbon atom, a 5-membered ring (for example, cyclopentane, pyrrolidine, tetrahydrofuran, dioxolane, tetrahydrothiophene, pyrrole) , Furan, thiophene, indole, benzofuran, benzothiophene), 6-membered ring (eg, cyclohexane, piperidine, piperazine, morpholine, tetrahydropyran, dioxane, pentamethylene sulfide, dithiane, benzene, piperidine, piperazine, pyridazine, quinoline, quinazoline) Or a 7-membered ring (eg, cycloheptane, hexamethyleneimine).
  • a 5-membered ring for example, cyclopentane,
  • R 9 and Y 2 may be bonded to each other to form a 5-membered, 6-membered, or 7-membered ring together with R 9 , Y 2 , and the carbon atom.
  • the 5-membered, 6-membered, and 7-membered rings that are formed include rings in which one bond in the ring formed by R 8 , Y 1, and a carbon atom is changed to a double bond.
  • X 5 represents a group capable of binding to Ma, and examples thereof include the same groups as X 2 in general formula (II-1). a represents 0, 1, or 2.
  • R 2 to R 5 , R 7 , and Ma are each a preferred embodiment of a complex containing a compound represented by the general formula (II) and a metal atom or a metal compound
  • X 3 and X 4 are Each independently NRa (Ra is a hydrogen atom, an alkyl group, a heterocyclic group) or an oxygen atom
  • Y 1 and Y 2 are each independently NRb (Rb is a hydrogen atom or an alkyl group), a nitrogen atom, or A carbon atom
  • X 5 is a group bonded through an oxygen atom or a nitrogen atom
  • R 8 and R 9 are each independently an alkyl group, an aryl group, a heterocyclic group, an alkoxy group, or an alkylamino group.
  • R 8 and Y 1 are bonded to each other to form a 5- or 6-membered ring
  • R 9 and Y 2 are bonded to each other to form a 5- or 6-membered ring
  • a is 0
  • it is an aspect represented by 1.
  • R 2 to R 5 , R 7 and Ma are each a preferred embodiment of a complex containing a compound represented by the general formula (II) and a metal atom or a metal compound, and X 3 and X 4 are oxygen atoms Y 1 is NH, Y 2 is a nitrogen atom, X 5 is an oxygen atom or a group bonded through a nitrogen atom, and R 8 and R 9 are each independently an alkyl group, Represents an aryl group, a heterocyclic group, an alkoxy group, or an alkylamino group, or R 8 and Y 1 are bonded to each other to form a 5-membered or 6-membered ring, and R 9 and Y 2 are bonded to each other A forms a 5-membered or 6-membered ring, and a is an embodiment represented by 0 or 1.
  • the general formula (II-1), (II-2) or (II-3) is a preferred embodiment of the dipyrromethene-based metal complex compound in which the compound represented by the general formula (II) is coordinated to a metal atom or a metal compound.
  • the complex compounds represented by formula (II-3) the complex compound represented by formula (II-3) is particularly preferred.
  • dipyrromethene metal complex compound in which the compound represented by the general formula (II) used in the present invention is coordinated to a metal atom or a metal compound are described in paragraphs 0179 to 0188 of JP2012-237985A. Which is incorporated herein by reference.
  • pyromethene dye Only one type of pyromethene dye may be used, or two or more types may be used in combination. When two or more types of pyromethene dyes are used in combination, the total amount preferably satisfies the above range.
  • the tetraazaporphyrin dye is preferably a compound represented by the general formula (III).
  • Z 1 , Z 2 , Z 3 and Z 4 all represent a nitrogen atom, or any one of Z 1 and Z 3 , Z 2 and Z 4 is both nitrogen Represents an atom, the other set represents CR, and each R independently represents a hydrogen atom, an alkyl group, or an aryl group;
  • a 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8 are each independently an alkyl group, alkenyl group, aryl group, alkoxy group, alkylthio group, aryloxy group, arylthio group, halogen atom, hydroxy group, alkoxycarbonyl group, aryloxycarbonyl group, amino group, A carbamoyl group, a sulfamoyl group, an acy
  • a 1 and A 2 , A 3 and A 4 , A 5 and A 6 , and A 7 and A 8 may be bonded to each other to form a ring structure
  • One set is an embodiment in which no ring structure is formed.
  • an alicyclic structure may be formed, but it is preferable not to form an aromatic ring structure, more preferably A 1 and A 2 , A 3 and A 4 , A 5 and In this embodiment, A 6 and any of A 7 and A 8 do not form a ring structure.
  • the alkyl group is preferably a linear, branched or cyclic alkyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms.
  • alkenyl group is preferably an alkenyl group having 2 to 48 carbon atoms, more preferably 2 to 18 carbon atoms.
  • the aryl group is preferably an aryl group having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, and specific examples thereof include a phenyl group and a naphthyl group.
  • the alkoxy group is preferably an alkoxy group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms. Specific examples thereof include a methoxy group, an ethoxy group, a 1-butoxy group, a 2-butoxy group, and an isopropoxy group.
  • Group, tert-butoxy group, dodecyloxy group and cycloalkyloxy group include, for example, cyclopentyloxy group, cyclohexyloxy group and the like.
  • the alkylthio group is preferably an alkylthio group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, and specific examples include a methylthio group, an ethylthio group, an octylthio group, and a cyclohexylthio group.
  • the aryloxy group is preferably an aryloxy group having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms.
  • the arylthio group is preferably an arylthio group having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, and specific examples include a phenylthio group.
  • a halogen atom Preferably, a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom are mentioned, Preferably a fluorine atom, a chlorine atom, and a bromine atom are mentioned.
  • the alkoxycarbonyl group is preferably an alkoxycarbonyl group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms.
  • Specific examples thereof include a methoxycarbonyl group, an ethoxycarbonyl group, an octadecyloxycarbonyl group, and a cyclohexyloxycarbonyl group. And a 2,6-di-tert-butyl-4-methylcyclohexyloxycarbonyl group.
  • the aryloxycarbonyl group is preferably an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, and specific examples include a phenoxycarbonyl group.
  • the amino group is preferably an amino group having 32 or less carbon atoms, more preferably 24 or less carbon atoms. Specific examples include an amino group, a methylamino group, an N, N-dibutylamino group, and a tetradecylamino group. 2-ethylhexylamino group, cyclohexylamino group and the like.
  • the carbamoyl group is preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms. Specific examples include a carbamoyl group, an N, N-diethylcarbamoyl group, and an N-ethyl-N group. -Octylcarbamoyl group, N, N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methylN-phenylcarbamoyl group, N, N-dicyclohexylcarbamoyl group alkoxycarbonyl group, etc. .
  • the sulfamoyl group is preferably a sulfamoyl group having 32 or less carbon atoms, more preferably 24 or less carbon atoms. Specific examples thereof include a sulfamoyl group, N, N-dipropylsulfamoyl group, N-ethyl-N-dodecyl group. Examples thereof include a sulfamoyl group, an N-ethyl-N-phenylsulfamoyl group, and an N-cyclohexylsulfamoyl group.
  • the acyl group is preferably an acyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms.
  • the silyloxy group is preferably a silyloxy group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms.
  • Specific examples include a trimethylsilyloxy group, a tert-butyldimethylsilyloxy group, and a diphenylmethylsilyloxy group.
  • the heterocyclic group is preferably a heterocyclic group having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms.
  • Examples include a 2-thienyl group, a 4-pyridyl group, a 2-furyl group, Examples include 2-pyrimidinyl group, 1-pyridyl group, 2-benzothiazolyl group, 1-imidazolyl group, 1-pyrazolyl group, benzotriazol-1-yl group and the like.
  • substituents represented by A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 and A 8 may be further substituted.
  • substituents that can be introduced include halogen atoms (for example, , A fluorine atom, a chlorine atom, a bromine atom, etc.), an alkyl group (preferably a linear, branched or cyclic alkyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms).
  • alkenyl groups specifically, for example, vinyl group, allyl group, 3-buten-1-yl group, etc., aryl group (preferably having 6 to 48 carbon atoms, more preferably having 6 to 48 carbon atoms).
  • aryl groups specifically, for example, a phenyl group, a naphthyl group, etc., a heterocyclic group (preferably a C1-C32, more preferably a C1-C18 heterocyclic group).
  • 2-thienyl group 4-pyridyl group, 2-furyl group, 2-pyrimidinyl group, 1-pyridyl group, 2-benzothiazolyl group, 1-imidazolyl group, 1-pyrazolyl group, benzotriazole -1-yl group, etc.
  • silyl groups preferably silyl groups having 3 to 38 carbon atoms, more preferably 3 to 18 carbon atoms. Specific examples include trimethylsilyl group, triethyl group, and the like.
  • Silyl group tributyl silyl group, tert- butyldimethylsilyl group, tert- hexyl dimethyl silyl group), a hydroxyl group, a cyano group, a nitro group,
  • An alkoxy group (preferably an alkoxy group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms), specifically, for example, a methoxy group, an ethoxy group, a 1-butoxy group, a 2-butoxy group, an iso In the case of propoxy group, tert-butoxy group, dodecyloxy group, and cycloalkyloxy group, for example, cyclopentyloxy group, cyclohexyloxy group, etc., aryloxy group (preferably having 6 to 48 carbon atoms, more preferably carbon Examples thereof include aryloxy groups having 6 to 24, specifically, for example, phenoxy group, 1-naphthoxy group and the like, and heterocyclic oxy groups (preferably having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms).
  • silyloxy groups preferably silyloxy groups having 1 to 32 carbon atoms, more preferably 1 to 18 carbon atoms.
  • acyloxy group preferably an acyloxy group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, specifically, for example, an acetoxy group, a pivaloyloxy group, a benzoyloxy group , Dodecanoyloxy group, etc.
  • an alkoxycarbonyloxy group preferably an alkoxycarbonyloxy group having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms, specifically, for example, an ethoxycarbonyloxy group, tert-butoxycarbonyloxy group
  • alkyloxycarbonyloxy group include a cyclohexyloxycarbonyloxy group and the like, and an aryloxycarbonyloxy group (preferably an aryloxycarbonyloxy group having 7 to 32 carbon atoms, more preferably 7 to
  • Specific examples include, for example, phenoxycarbonyloxy group and the like, carbamoyloxy group (preferably carbamoyloxy group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, For example, N, N-dimethylcarbamoyloxy group, N-butylcarbamoyloxy group, N-phenylcarbamoyloxy group, N-ethyl-N-phenylcarbamoyloxy group, etc.), sulfamoyloxy group (preferably having 1 to 32, more preferably sulfa having 1 to 24 carbon atoms
  • Specific examples include N, N-diethylsulfamoyloxy group, N-propylsulfamoyloxy group and the like, alkylsulfonyloxy group (preferably having 1 to 38 carbon atoms, more preferably).
  • alkylsulfonyloxy group having 1 to 24 carbon atoms includes an alkylsulfonyloxy group having 1 to 24 carbon atoms. Specifically, for example, a methylsulfonyloxy group, a hexadecylsulfonyloxy group, a cyclohexylsulfonyloxy group, etc., an arylsulfonyloxy group (preferably having 6 carbon atoms) An arylsulfonyloxy group having 6 to 24 carbon atoms, more preferably 6 to 24 carbon atoms.
  • a phenylsulfonyloxy group, etc. an acyl group (preferably 1 to 48 carbon atoms, more preferably a carbon number) 1 to 24 acyl groups are mentioned, for example, formyl group, ace Group, pivaloyl group, benzoyl group, tetradecanoyl group, cyclohexanoyl group, etc.), alkoxycarbonyl group (preferably C2-C48, more preferably C2-C24 alkoxycarbonyl group).
  • aryloxycarbonyl group preferably Is an aryloxycarbonyl group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, specifically, for example, a phenoxycarbonyl group
  • a carbamoyl group (preferably a carbamoyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, specifically, for example, carbamoyl group, N, N-diethylcarbamoyl group, N-ethyl-N— Octylcarbamoyl group, N, N-dibutylcarbamoyl group, N-propylcarbamoyl group, N-phenylcarbamoyl group, N-methylN-phenylcarbamoyl group, N, N-dicyclohexylcarbamoyl group, etc.), amino group (preferably Examples thereof include amino groups having 32 or less carbon atoms, more preferably 24 or less carbon atoms.
  • Specific examples include amino groups, methylamino groups, N, N-dibutylamino groups, tetradecylamino groups, and 2-ethyl.
  • Xylamino group, cyclohexylamino group, etc.) anilino group (preferably having 6 to 32 carbon atoms, more preferably Examples thereof include 6-24 anilino groups, and specific examples include, for example, anilino group, N-methylanilino group, etc., heterocyclic amino group (preferably having 1 to 32 carbon atoms, more preferably 1 to 18 heterocyclic amino group).
  • Specific examples include, for example, 4-pyridylamino group and the like, and carbonamide groups (preferably having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms).
  • carbonamide groups preferably having 2 to 48 carbon atoms, more preferably 2 to 24 carbon atoms.
  • a ureido group preferably having a carbon number of 1 to 32, more preferably a carbon number of 1 to 24 may be mentioned.
  • Is for example, a ureido group, N, N-dimethylureido group, N-phenylureido group, etc.), an imide group (preferably having 3 carbon atoms)
  • imide groups having 24 or less carbon atoms are more preferable.
  • N-succinimide group, N-phthalimide group and the like alkoxycarbonylamino groups (preferably having 2 to 48 carbon atoms, and more preferable). Includes an alkoxycarbonylamino group having 2 to 24 carbon atoms.
  • Specific examples include a methoxycarbonylamino group, an ethoxycarbonylamino group, a tert-butoxycarbonylamino group, an octadecyloxycarbonylamino group, and a cyclohexyloxycarbonylamino group.
  • An aryloxycarbonylamino group preferably an aryloxycarbonylamino group having 7 to 32 carbon atoms, more preferably 7 to 24 carbon atoms, specifically, for example, a phenoxycarbonylamino group
  • An amide group preferably Examples thereof include a sulfonamide group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms.
  • Specific examples include a methanesulfonamide group, a butanesulfonamide group, a benzenesulfonamide group, a hexadecanesulfonamide group, and cyclohexane.
  • a sulfonamido group a sulfamoylamino group (preferably a sulfamoylamino group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms), specifically, for example, N, N-dipro A pyrsulfamoylamino group, an N-ethyl-N-dodecylsulfamoylamino group, etc.), an azo group (preferably an azo group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms).
  • alkylthio group preferably an alkylthio group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms, specifically, for example, a methylthio group, an ethylthio group, an octylthio group, a cyclohexylthio group, etc.
  • an arylthio group Preferably an arylthio group having 6 to 48 carbon atoms, more preferably 6 to 24 carbon atoms, specifically, for example, a phenylthio group
  • a heterocyclic thio group preferably having 1 to 32 carbon atoms, more Preferred examples include a heterocyclic thio group having 1 to 18 carbon atoms, and specific examples include 2-benzothiazolylthio group, 2-pyridylthio group, 1-phenyltetrazolylthio group and the like, alkylsulfinyl group ( Preferred are alkylsulfinyl groups having 1 to 32 carbon
  • Dodecanesulfinyl group arylsulfinyl group (preferably an arylsulfinyl group having 6 to 32 carbon atoms, more preferably 6 to 24 carbon atoms, specifically, for example, phenylsulfinyl group), alkylsulfonyl group (Preferably includes an alkylsulfonyl group having 1 to 48 carbon atoms, more preferably 1 to 24 carbon atoms. Specific examples include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, a butylsulfonyl group, and an isopropylsulfonyl group.
  • sulfamoyl group preferably sulfamoyl group having 32 or less carbon atoms, more preferably 24 or less carbon atoms, specifically, for example, sulfamoyl group, N N-dipropylsulfamoyl group, N-ethyl-N-dodecylsulfamoyl group, N-ethyl-N-phenylsulfamoyl group, N-cyclohexylsulfamoyl group, etc.), sulfo group, phosphonyl group (preferably Is a phosphonyl group having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms.
  • phosphinoyl Amino group preferably phosphinoyla having 1 to 32 carbon atoms, more preferably 1 to 24 carbon atoms
  • a mino group specifically, a diethoxyphosphinoylamino group, a dioctyloxyphosphinoylamino group, and the like.
  • alkyl group and aryl group represented by R are A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7. and alkyl groups described as the substituent a 8 represents, and is synonymous with an aryl group.
  • the metal atom represented by M is preferably Al, Si, Ca, Ti, V, Mn, Fe, Co, Ni, Cu, Zn, Ge, Mo, Ru, Rh, Pd, In, Represents Sn, Pt, Pb, Mg, more preferably represents Al, V, Mn, Fe, Co, Ni, Cu, Zn, Ru, Rh, Pd, Pt, Mg, and more preferably Al, V, Mn, Fe, Co, Ni, Cu, Zn, and Mg are represented, and V, Co, Ni, Cu, and Zn are particularly preferably represented.
  • substituted metal atom represented by M in the general formula (III), which is a divalent atom or atomic group include metal halide atoms (for example, Al-F, Al-Cl, Al -Br, Al-I, In- F, In-Cl, Fe-Cl, In-Br, In-I, SiF 2, SiCl 2, SiBr 2, SiI 2, TiF 2, TiCl 2, TiBr 2, TiI 2 Etc.), MB (B is a substituent such as an alkyl group, an aryl group, a naphthyl group, an alkoxy group, a hydroxyl group, and the like.
  • metal halide atoms for example, Al-F, Al-Cl, Al -Br, Al-I, In- F, In-Cl, Fe-Cl, In-Br, In-I, SiF 2, SiCl 2, SiBr 2, SiI 2, TiF 2, TiCl 2, TiBr 2, TiI 2 Etc.
  • B is a substitu
  • Si (CH 3 ) 3 Si (C 2 H 5 ) 3 Al—C 6 H 5 , In—C 6 H 5 , Al (OH), Mn (OH), Si (OH) 2 , Zr (OH) 2 , Al—OCH 3 , Al—O (C 6 H 5 Etc.) and metal oxide atoms (for example, TiO, MnO, VO, etc.).
  • the tetraazaporphyrin dye is preferably a tetraazaporphyrin compound in which all of Z 1 , Z 2 , Z 3 and Z 4 represent a nitrogen atom, preferably a compound represented by the general formula (III-2).
  • Formula (III-2) In general formula (III-2), A 1 , A 2 , A 3 , A 4 , A 5 , A 6 , A 7 , A 8 and M are the same as A 1 , A 2 , A 3 in general formula (III). , A 4 , A 5 , A 6 , A 7 , A 8 and M are respectively synonymous.
  • the maximum value of the absorption spectrum of the compound represented by the general formula (III) is preferably from 550 nm to 650 nm, more preferably from 570 nm to 630 nm, and particularly preferably from 570 nm to 610 nm from the viewpoint of the transmittance of the color filter.
  • the description in paragraphs 0124 to 0141 of JP2013-210577A can be referred to, and the contents thereof are incorporated in the present specification.
  • Only one tetraazaporphyrin dye may be used, or two or more tetraazaporphyrin dyes may be used in combination.
  • the total amount preferably satisfies the above range.
  • the coloring composition of the present invention may further contain a pigment.
  • a pigment By including the pigment, not only the hue can be adjusted, but also the heat resistance, light resistance, patterning characteristics and the like can be further improved.
  • the pigment to be combined is preferably a pigment having a purple to blue hue, more preferably a blue pigment, Pigment Blue 1, 2, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 22, 60, 64, 66, 79, 80, and Pigment Green 7 in which Cl is changed to OH At least one selected from is more preferred.
  • Pigment Blue 1, 15: 3, 15: 6, 66 and 79 are preferable, and Pigment Blue 15: 3 and 15: 6 are more preferable.
  • the total amount of the pigment having a purple to blue hue is preferably 0.1 to 20 mass with respect to the total amount of the salt compound. 1 to 15% by mass is more preferable.
  • the content of the pigment in the composition of the present invention is preferably 30% by mass or less, more preferably 15% by mass or less, and still more preferably 10% by mass or less with respect to the total mass of the coloring material in the composition of the present invention.
  • the composition of the present invention preferably contains a curable compound in addition to the components described above.
  • the curable compound include a polymerizable compound and an alkali-soluble binder (including an alkali-soluble binder containing a polymerizable group), and the curable compound is appropriately selected depending on the application and production method.
  • the composition of the present invention preferably contains a photopolymerization initiator. For example, when a colored layer is formed by a photoresist, the composition of the present invention is added to the salt compound, a solvent that dissolves the salt compound at 1.0% by mass or more at 25 ° C., and the purple colorant.
  • the composition of the present invention is added to the salt compound, a solvent that dissolves the salt compound at 1.0% by mass or more at 25 ° C., and the purple colorant. It preferably contains a polymerizable compound as a curable compound, a solvent and a photopolymerization initiator. Furthermore, a surfactant may be included. Details of these will be described below.
  • the colored composition of the present invention preferably contains a curable compound.
  • the curable compound preferably contains at least a polymerizable compound.
  • ⁇ polymerizable compound >> The colored composition of the present invention preferably contains at least one polymerizable compound.
  • the polymerizable compound is, for example, a polymerizable compound having at least one ethylenically unsaturated double bond, and can be selected and used from components constituting a known composition, as disclosed in JP-A-2006-23696. Examples include the components described in paragraph numbers [0010] to [0020] and the components described in paragraph numbers [0027] to [0053] of JP-A-2006-64921.
  • the polymerizable compound is preferably a compound having a terminal ethylenically unsaturated bond, and more preferably selected from compounds having two or more terminal ethylenically unsaturated bonds.
  • a compound group is widely known in the industrial field, and these can be used without particular limitation in the present invention. These may be in any chemical form such as, for example, monomers, prepolymers, ie dimers, trimers and oligomers, or mixtures thereof and multimers thereof.
  • a urethane-added polymerizable compound produced by an addition reaction between an isocyanate and a hydroxyl group is also suitable, such as JP-A-51-37193, JP-B-2-32293, and JP-B-2-16765.
  • Urethane compounds having them are also suitable.
  • Other examples include polyester acrylates, epoxy resins and (meth) described in JP-A-48-64183, JP-B-49-43191 and JP-B-52-30490.
  • pentaerythritol tri (meth) acrylate pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, dipentaerythritol hexa (meth) acrylate, tri ((meth) acryloyloxyethyl) isocyanurate.
  • Pentaerythritol tetra (meth) acrylate EO modified products dipentaerythritol hexa (meth) acrylate EO modified products, etc., and commercially available products include NK ester A-TMMT, NK ester A-TMM-3, and NK oligo UA.
  • NK Oligo UA-7200 manufactured by Shin-Nakamura Chemical Co., Ltd.
  • examples of the polymerizable compound (C) include components described in paragraphs [0031] to [0061] of JP-A-2009-265630 from the viewpoint of low-temperature curability.
  • the polymerizable compound (C) the following (1) to (20) and (M-1) to (M-8) are preferred.
  • a colored film formed using a polymerizable monomer having two ethylenically unsaturated bonds in the molecule is excellent from the viewpoint of low-temperature curability.
  • the content of the polymerizable compound with respect to the total solid content of the composition is preferably 10% by mass to 80% by mass, more preferably 15% by mass to 75% by mass, and more preferably 20% by mass. From 60% to 60% by weight is particularly preferred. Only 1 type may be used for a polymeric compound and it may use 2 or more types together. When two or more polymerizable compounds are used in combination, the total amount preferably satisfies the above range.
  • the colored composition of the present invention preferably contains at least one photopolymerization initiator.
  • the photopolymerization initiator is not particularly limited as long as it can polymerize the polymerizable compound, and is preferably selected from the viewpoints of characteristics, initiation efficiency, absorption wavelength, availability, cost, and the like.
  • the photopolymerization initiator is a compound that is exposed to exposure light and starts and accelerates polymerization of the polymerizable compound.
  • a compound that responds to actinic rays having a wavelength of 300 nm or longer and initiates and accelerates polymerization of the polymerizable compound is preferable.
  • a photopolymerization initiator that does not directly respond to actinic rays having a wavelength of 300 nm or longer can also be preferably used in combination with a sensitizer.
  • oxime ester compounds organic halogenated compounds, oxydiazole compounds, carbonyl compounds, ketal compounds, benzoin compounds, acridine compounds, organic peroxides, azo compounds, coumarin compounds, azide compounds, metallocene compounds
  • examples include hexaarylbiimidazole compounds, organic boric acid compounds, disulfonic acid compounds, onium salt compounds, acylphosphine (oxide) compounds, benzophenone compounds, acetophenone compounds, benzimidazole compounds, and derivatives thereof.
  • oxime ester compounds and hexaarylbiimidazole compounds are preferable from the viewpoint of sensitivity.
  • Examples of the oxime ester compound include JP 2000-80068, JP 2001-233842, JP 2004-534797, WO 2005/080337, WO 2006/018933, JP
  • JP The compounds described in JP 2007-210991 A, JP 2007-231000 A, JP 2007-2699779 A, JP 2009-191061 A, and International Publication No. 2009/131189 can be used.
  • a compound represented by the following general formula (A) is also suitable as an oxime ester compound that is a photopolymerization initiator.
  • X 1 , X 2 , and X 3 each independently represent a hydrogen atom, a halogen atom, or an alkyl group
  • R 1 is —R, —OR, —COR, —SR, —CONRR 'Or -CN
  • R 2 and R 3 are each independently.
  • —R, —OR, —COR, —SR, or —NRR ′ is represented.
  • R and R ′ each independently represents an alkyl group, an aryl group, an aralkyl group, or a heterocyclic group, and these groups are substituted with one or more selected from the group consisting of a halogen atom and a heterocyclic group.
  • One or more of carbon atoms constituting the alkyl chain in the alkyl group and the aralkyl group may be replaced with an unsaturated bond, an ether bond, or an ester bond, and R and R ′ are bonded to each other. May form a ring.
  • halogen atom examples include fluorine, chlorine, bromine, and iodine
  • X 1 , X 2 , and X 3 are alkyl
  • alkyl group in the case of representing a group include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, hexyl, heptyl, octyl, isooctyl, 2- Ethylhexyl, tert-octyl, nonyl, isononyl, decyl, isodecyl, vinyl, allyl, butenyl, ethynyl, propynyl, methoxyethyl, and
  • X ⁇ 1 >, X ⁇ 2 > and X ⁇ 3 > represent a hydrogen atom, or X ⁇ 1 > represents an alkyl group and X ⁇ 2 > and X ⁇ 3 > both represent a hydrogen atom.
  • examples of the alkyl group represented by R and R ′ include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, amyl, isoamyl, tert-amyl, Hexyl, heptyl, octyl, isooctyl, 2-ethylhexyl, tertiary octyl, nonyl, isononyl, decyl, isodecyl, vinyl, allyl, butenyl, ethynyl, propynyl, methoxyethyl, ethoxyethyl, propyloxyethyl, methoxyethoxyethyl, ethoxyethoxy Examples include ethyl, propyloxyethoxyethyl, methoxypropyl, monofluoromethyl, difluoromethyl,
  • Examples of the aryl group represented by R and R ′ include phenyl, tolyl, xylyl, ethylphenyl, chlorophenyl, naphthyl, anthryl, phenanthrenyl and the like.
  • Examples of the aralkyl group represented by R and R ′ include benzyl, chlorobenzyl, ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, phenylethyl, phenylethenyl and the like.
  • Examples of the heterocyclic group represented by R and R ′ include pyridyl, pyrimidyl, furyl, thiophenyl and the like.
  • Examples of the ring formed by bonding R and R ′ to each other include a piperidine ring and a morpholine ring.
  • R 2 and R 3 including R and R ′ are each independently a methyl group, a hexyl group, a cyclohexyl group, —S—Ph, —S—Ph—Cl, and —S—Ph—.
  • Br is a particularly preferred embodiment.
  • X 1 , X 2 , and X 3 are all hydrogen atoms;
  • R 1 is an alkyl group, particularly a methyl group;
  • R 2 is alkyl
  • Particularly preferred as photoinitiators are those which are groups, in particular methyl groups; those in which R 3 is an alkyl group, in particular ethyl group.
  • photopolymerization initiator represented by the general formula (A) include compounds A to G exemplified below.
  • present invention is not limited by the following compounds.
  • the photopolymerization initiator represented by the general formula (A) can be synthesized, for example, by the method described in JP-A-2005-220097.
  • the compound represented by the general formula (A) used in the present invention has an absorption wavelength in a wavelength region of 250 nm to 500 nm. More preferable examples include those having an absorption wavelength in the wavelength region of 300 nm to 380 nm. In particular, those having high absorbance at 308 nm and 355 nm are preferable.
  • a compound represented by the following general formula (B) is also suitable as an oxime ester compound that is a photopolymerization initiator from the viewpoint of sensitivity, stability over time, and coloring during post-heating.
  • R 22 represents a monovalent substituent.
  • a 22 represents a divalent linking group, and Ar represents an aryl group.
  • n is an integer of 0 to 5.
  • X 22 represents a monovalent substituent, and when n is an integer of 2 to 4, a plurality of X 22 may be the same or different.
  • the monovalent substituent represented by R 22 is preferably a monovalent nonmetallic atomic group shown below.
  • Examples of the monovalent nonmetallic atomic group represented by R 22 include an alkyl group which may have a substituent, an aryl group which may have a substituent, an alkylsulfonyl group which may have a substituent, Examples include an arylsulfonyl group which may have a substituent, an acyl group which may have a substituent, a heterocyclic group which may have a substituent, and the like.
  • the alkyl group which may have a substituent is preferably an alkyl group having 1 to 30 carbon atoms, for example, methyl group, ethyl group, propyl group, butyl group, hexyl group cyclopentyl group, cyclohexyl group, trifluoromethyl group. , Etc.
  • the aryl group which may have a substituent is preferably an aryl group having 6 to 30 carbon atoms, and examples thereof include a phenyl group, a biphenyl group, a 1-naphthyl group, and a 2-naphthyl group.
  • the alkylsulfonyl group which may have a substituent is preferably an alkylsulfonyl group having 1 to 20 carbon atoms, and examples thereof include a methylsulfonyl group and an ethylsulfonyl group.
  • the arylsulfonyl group which may have a substituent is preferably an arylsulfonyl group having 6 to 30 carbon atoms, and examples thereof include a phenylsulfonyl group and a 1-naphthylsulfonyl group.
  • the acyl group which may have a substituent is preferably an acyl group having 2 to 20 carbon atoms.
  • acetyl group, propanoyl group, butanoyl group, trifluoromethylcarbonyl group, pentanoyl group benzoyl group, 1-naphthoyl Group, 2-naphthoyl group, 4-methylsulfanylbenzoyl group, 4-phenylsulfanylbenzoyl group, 4-dimethylaminobenzoyl group, 4-diethylaminobenzoyl group, 2-chlorobenzoyl group, 2-methylbenzoyl group, 2-methoxybenzoyl Group, 2-butoxybenzoyl group, 3-chlorobenzoyl group, 3-trifluoromethylbenzoyl group, 3-cyanobenzoyl group, 3-nitrobenzoyl group, 4-fluorobenzoyl group, 4-cyanobenzoyl group, 4-methoxybenzoyl Groups and the like.
  • the heterocyclic group that may have a substituent is preferably an aromatic or aliphatic heterocyclic ring containing a nitrogen atom, an oxygen atom, a sulfur atom, or a phosphorus atom.
  • R 22 is more preferably an unsubstituted or substituted acyl group from the viewpoint of high sensitivity, and specifically, an unsubstituted or substituted acetyl group, propionyl group, benzoyl group, toluyl group Is preferred.
  • the substituent include groups represented by the following structural formulas. Among them, any of (d-1), (d-4) and (d-5) is preferable.
  • Examples of the divalent linking group represented by A 22 include an optionally substituted alkylene having 1 to 12 carbon atoms, an optionally substituted cyclohexylene, and an optionally substituted alkynylene. Is mentioned.
  • Examples of the substituent that can be introduced into these groups include halogen atoms such as fluorine atom, chlorine atom, bromine atom and iodine atom, alkoxy groups such as methoxy group, ethoxy group and tert-butoxy group, phenoxy group, p- Examples include aryloxy groups such as a tolyloxy group, alkoxycarbonyl groups such as a methoxycarbonyl group, a butoxycarbonyl group, and a phenoxycarbonyl group.
  • a 22 is 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 due to heating.
  • the aryl group represented by Ar is preferably an aryl group having 6 to 30 carbon atoms, and may have a substituent.
  • Ar is phenyl group, biphenyl group, 1-naphthyl group, 2-naphthyl group, terphenyl group, quarterphenyl group, o-, m-, and p-tolyl group, xylyl group, o-, m -, And p-cumenyl group, mesityl group and the like.
  • a substituted or unsubstituted phenyl group is preferable from the viewpoint of increasing sensitivity and suppressing coloring due to heating.
  • the substituent include halogen atoms such as a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, an alkoxy such as a methoxy group, an ethoxy group and a tert-butoxy group.
  • aryloxy group such as phenoxy group, p-tolyloxy group, alkoxycarbonyl group such as methoxycarbonyl group, butoxycarbonyl group, phenoxycarbonyl group, acyloxy group such as acetoxy group, propionyloxy group, benzoyloxy group, acetyl group, Benzoyl group, isobutyryl group, acryloyl group, methacryloyl group, methacrylyl group and other acyl groups, methylamino group, cyclohexylamino group and other alkylamino groups, dimethylamino group, diethylamino group, morpholino group, piperidino group and other dialkylamino groups, F Niruamino group, a methyl group, an ethyl group, tert- butyl group, an alkyl group such as a dodecyl group, a hydroxy group, a carboxy group, and the like
  • the structure of “SAr” formed by the Ar and the adjacent S is the following structure.
  • Examples of the monovalent substituent represented by X 22 include an alkyl group that may have a substituent, an aryl group that may have a substituent, an alkenyl group that may have a substituent, and a substituent.
  • Good arylthiooxy groups, halogen atoms and the like can be mentioned.
  • the alkyl group which may have a substituent is preferably an alkyl group having 1 to 30 carbon atoms.
  • the aryl group which may have a substituent is preferably an aryl group having 6 to 30 carbon atoms.
  • a phenyl group for example, a phenyl group, a biphenyl group, a 1-naphthyl group, a 2-naphthyl group, a terphenyl group, a quarterphenyl group, o-, m-, and p-tolyl groups, xylyl groups, and the like.
  • the alkenyl group which may have a substituent is preferably an alkenyl group having 2 to 10 carbon atoms, and examples thereof include a vinyl group, an allyl group, and a styryl group.
  • the alkynyl group which may have a substituent is preferably an alkynyl group having 2 to 10 carbon atoms, and examples thereof include an ethynyl group, a propynyl group, and a propargyl group.
  • the alkoxy group which may have a substituent is preferably an alkoxy group having 1 to 30 carbon atoms, and examples thereof include a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, a butoxy group, and a benzyloxy group. .
  • the aryloxy group which may have a substituent is preferably an aryloxy group having 6 to 30 carbon atoms, such as a phenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a 2-chlorophenyloxy group, Examples include 2-methylphenyloxy group, 2-methoxyphenyloxy group, and the like.
  • the alkylthiooxy group which may have a substituent is preferably a thioalkoxy group having 1 to 30 carbon atoms, such as a methylthiooxy group, an ethylthiooxy group, a propylthiooxy group, an isopropylthiooxy group, a butylthiooxy group.
  • the arylthiooxy group which may have a substituent is preferably an arylthiooxy group having 6 to 30 carbon atoms, such as a phenylthiooxy group, a 1-naphthylthiooxy group, a 2-naphthylthiooxy group, 2 -Chlorophenylthiooxy group, 2-methylphenylthiooxy group, 2-methoxyphenylthiooxy group, 2-butoxyphenylthiooxy group, 3-chlorophenylthiooxy group, 3-trifluoromethylphenylthiooxy group, 3-cyano Phenylthiooxy group, 3-nitrophenylthiooxy group, 4-fluorophenylthiooxy group, 4-cyanophenylthiooxy group, 4-methoxyphenylthiooxy group, 4-dimethylaminophenylthiooxy group, 4-methylsulfanyl Phenylthiooxy group, 4-phenylsulfanylphenyl There is
  • halogen atom examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • halogenated alkyl group which may have a substituent examples include a monofluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a dichloromethyl group, a trichloromethyl group, a monobromomethyl group, a dibromomethyl group, and a tribromomethyl group.
  • Examples of the amide group which may have a substituent on N examples include an N, N-dimethylamide group and an N, N-diethylamide group.
  • X 22 has an alkyl group which may have a substituent, an aryl group which may have a substituent, and a substituent from the viewpoint of solvent solubility and improvement in absorption efficiency in the long wavelength region.
  • a good amide group is preferable, and an alkyl group which may have a substituent is more preferable.
  • n in the general formula (B) represents an integer of 0 to 5, and is preferably an integer of 0 to 3, more preferably an integer of 0 to 2, from the viewpoint of ease of synthesis.
  • X 22 there are a plurality the plurality of X 22 may be the same or may be different.
  • the compound represented by the general formula (B) used in the present invention has an absorption wavelength in a wavelength region of 250 nm to 500 nm. More preferable examples include those having an absorption wavelength in the wavelength region of 300 nm to 380 nm. In particular, those having high absorbance at 308 nm and 355 nm are preferable.
  • organic halogenated compounds include Wakabayashi et al., “Bull Chem. Soc. Japan” 42, 2924 (1969), US Pat. No. 3,905,815, Japanese Patent Publication No. 46-4605. JP, 48-34881, JP 55-3070, JP 60-239736, JP 61-169835, JP 61-169837, JP 62-58241, JP-A 62-212401, JP-A 63-70243, JP-A 63-298339, P. Examples include compounds described in Hutt “Journal of Heterocyclic Chemistry” 1 (No. 3), (1970), and in particular, oxazole compounds substituted with a trihalomethyl group and s-triazine compounds.
  • hexaarylbiimidazole compounds include, for example, JP-B-6-29285, US Pat. Nos. 3,479,185, 4,311,783, and 4,622,286.
  • Various compounds described in the specification specifically 2,2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (o- Bromophenyl)) 4,4 ′, 5,5′-tetraphenylbiimidazole, 2,2′-bis (o, p-dichlorophenyl) -4,4 ′, 5,5′-tetraphenylbiimidazole, 2, 2′-bis (o-chlorophenyl) -4,4 ′, 5,5′-tetra (m-methoxyphenyl) biimidazole, 2,2′-bis (o, o′-dichlorophenyl) -4,4 ′, 5,
  • the photopolymerization initiator can be used alone or in combination of two or more.
  • multiple types of compounds represented by general formula (A) may be used, and multiple types of compounds represented by general formula (B) may be used.
  • the total content of the photopolymerization initiator is preferably 0.1% by mass to 20% by mass, and preferably 0.5% by mass to 10% by mass with respect to the total solid content in the coloring composition. More preferred is 1% by mass to 5% by mass. Within this range, the sensitivity during exposure is high and the color characteristics are also good.
  • the colored composition of the present invention may further contain a binder resin in order to improve the film forming property.
  • a binder resin an alkali-soluble binder is preferably used from the viewpoint of pattern formation.
  • 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 high molecular polymer that is soluble in an organic solvent and can be developed with a weak alkaline aqueous solution.
  • linear organic high molecular polymers examples 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.
  • alkali-soluble binders include those obtained by adding an acid anhydride to a polymer having a hydroxyl group, polyhydroxystyrene resins, polysiloxane resins, poly (2-hydroxyethyl (meth) acrylate), Polyvinyl pyrrolidone, polyethylene oxide, polyvinyl alcohol, etc. are also useful.
  • 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.
  • the alkali-soluble binder may have a polymerizable group in the side chain in order to improve the crosslinking efficiency, and includes, for example, an allyl group, a (meth) acryl group, an allyloxyalkyl group, etc. in the side chain.
  • Polymers and the like are also useful. Examples of the above-described polymer containing a polymerizable group include a dial NR series (manufactured by Mitsubishi Rayon Co., Ltd.), Photomer 6173 (COOH-containing polyurethane acrylic oligomer. Diamond Shamrock Co.
  • 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 preferably acrylic resins, acrylamide resins, and acrylic / acrylamide copolymer resins.
  • An allyl methacrylate / methacrylic acid copolymer is also preferred.
  • acrylic resin examples include a copolymer made of a monomer selected from benzyl (meth) acrylate, (meth) acrylic acid, hydroxyethyl (meth) acrylate, (meth) acrylamide, and the like, the above-mentioned Photomer 6173, and KS resist-106. Cyclomer P series and the like are preferable.
  • the alkali-soluble binder is preferably a polymer having a weight average molecular weight (polystyrene equivalent value measured by GPC method) of 1,000 to 200,000 from the viewpoint of developability, liquid viscosity, etc., and 2,000 to 100,000. More preferred is a polymer of 5,000 to 50,000.
  • the alkali-soluble binder can be used alone or in combination of two or more.
  • a known additive such as a polyfunctional thiol compound, a chain transfer agent, a polymerization inhibitor, an organic solvent, a surface active agent is used as long as the effects of the present invention are not impaired.
  • the coloring composition of the present invention may contain a polyfunctional thiol compound.
  • the coloring composition of the present invention contains a polyfunctional thiol compound to increase sensitivity and suppress ion elution caused by coloring materials such as dyes. When used, deterioration in image quality such as crosstalk can be prevented, and a clear display with high image quality becomes possible.
  • the “polyfunctional thiol compound” means a compound having two or more thiol groups in the molecule.
  • the polyfunctional thiol compound is preferably a low molecular weight compound having a molecular weight of 100 or more, specifically, preferably having a molecular weight of 100 to 1500, and more preferably 150 to 1000.
  • the polyfunctional thiol compound preferably has 2 to 10 thiol groups in the molecule, more preferably 2 to 6, and particularly preferably 2 to 4.
  • these compounds are preferably used as a system that is used auxiliary when the radical polymerizable monomer is polymerized.
  • the addition amount of the polyfunctional thiol compound is 1 to 20% by mass with respect to the total solid content of the composition, or is less than the addition amount of the radical polymerizable monomer contained at the same time. It is preferable to make it an addition amount.
  • Propionate dipentaerythritol hexakis (3-mercaptopropionate), pentaerythritol tetrakis (thioglycolate), pentaerythritol tetrakis (3-mercaptobutyrate), butanediol bis (3-mercaptobutyrate), 1,4-bis (3-mercaptobutyloxy) butane, 1,3,5-tris (3-mercaptobutyloxyethyl) -1,3,5-triazine-2,4,6 (1H, 3H, 5H) -Trifunctional, etc. It mentioned as compound. Particularly preferred are compounds containing secondary SH, and it is preferred to have a triazine skeleton from the viewpoint of liquid stability. Specific examples include Karenz MT series (manufactured by Showa Denko KK).
  • the content of the polyfunctional thiol compound is preferably 0.01% by mass to 20% by mass and more preferably 0.1% by mass to 10% by mass with respect to the total solid content in the colored composition. .
  • the content of the polyfunctional thiol compound is within this range, the sensitivity of the colored composition is good, the storage stability is good, the pixel adhesion in the obtained color filter is good, there is no pattern defect, and the liquid crystal
  • a colored composition having good electrical characteristics can be provided.
  • a sensitizer can also be added to the coloring composition of the present invention.
  • Typical sensitizers used in the present invention include Krivello [J. V. Crivello, Adv. in Polymer Sci, 62, 1 (1984)]. Specific examples include pyrene, perylene, acridine, thioxanthone, 2-chlorothioxanthone, benzoflavin, N-vinylcarbazole, 9,10. -Dibutoxyanthracene, anthraquinone, benzophenone, coumarin, ketocoumarin, phenanthrene, camphorquinone, phenothiazine derivatives and the like.
  • the sensitizer is preferably added in a proportion of 50 to 200% by mass with respect to the photopolymerization initiator.
  • a chain transfer agent can also be added to the coloring composition of the present invention.
  • the chain transfer agent used in the present invention include N, N-dialkylaminobenzoic acid alkyl esters such as N, N-dimethylaminobenzoic acid ethyl ester, 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, and 2-mercapto.
  • Examples include mercapto compounds having a heterocyclic ring such as benzimidazole and N-phenylmercaptobenzimidazole.
  • a chain transfer agent may be used individually by 1 type, and may use 2 or more types together.
  • the addition amount of the chain transfer agent is preferably in the range of 0.01% by mass to 15% by mass with respect to the total solid content of the coloring composition of the present invention, from the viewpoint of reducing the sensitivity variation. 1% by mass to 10% by mass is more preferable, and 0.5% by mass to 5% by mass is particularly preferable.
  • the coloring composition of the present invention may contain a polymerization inhibitor.
  • a polymerization inhibitor means hydrogen donation (or hydrogen donation), energy donation (or energy donation), electron donation (or electron donation) to polymerization initiation species such as radicals generated in the colored composition by light or heat.
  • the polymerization inhibitors described in paragraphs [0154] to [0173] of JP-A-2007-334322 can be used. Among these, p-methoxyphenol is preferably used as the polymerization inhibitor.
  • the content of the polymerization inhibitor in the colored composition of the present invention is preferably 0.0001% by mass to 5% by mass, more preferably 0.001% by mass to 5% by mass, with respect to the total mass of the polymerizable compound. 0.001% by mass to 1% by mass is particularly preferable.
  • the coloring composition of the present invention may contain a surfactant.
  • a surfactant any of anionic, cationic, nonionic, or amphoteric surfactants can be used, but a preferred surfactant is a nonionic surfactant. Specific examples include nonionic surfactants described in paragraph 0058 of JP-A-2009-098616, and among them, fluorine surfactants are preferable.
  • Other surfactants that can be used in the present invention include, for example, commercially available products such as MegaFuck F142D, F172, F173, F176, F177, F183, F479, F482, and F554.
  • F780, F781, F781-F, R30, R08, F-472SF, BL20, R-61, R-90 (manufactured by DIC Corporation), Florard FC-135, FC -170C, FC-430, FC-431, Novec FC-4430 (manufactured by Sumitomo 3M), Asahi Guard AG7105,7000,950,7600, Surflon S-112, S-113, S-131 S-141, S-145, S-382, SC-101, SC-102, SC-103, SC-104, SC-105, SC-106 (manufactured by Asahi Glass Co., Ltd.), Ftop EF351, 352, 801, 802 (manufactured by Mitsubishi Materials Electronic Chemicals Co., Ltd.), Footgent 250 (manufactured by Neos Co., Ltd.), etc.
  • the surfactant includes a structural unit A and a structural unit B represented by the following formula (W), and has a polystyrene-equivalent weight average molecular weight (Mw) measured by gel permeation chromatography using tetrahydrofuran as a solvent.
  • W polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography using tetrahydrofuran as a solvent.
  • Mw polystyrene-equivalent weight average molecular weight measured by gel permeation chromatography using tetrahydrofuran as a solvent.
  • a copolymer having a molecular weight of 000 or more and 10,000 or less can be given as a preferred example.
  • R 1 and R 3 each independently represent a hydrogen atom or a methyl group
  • R 2 represents a linear alkylene group having 1 to 4 carbon atoms
  • R 4 represents a hydrogen atom or carbon number
  • 1 represents an alkyl group having 1 to 4 carbon atoms
  • L represents an alkylene group having 3 to 6 carbon atoms
  • p and q are mass percentages representing a polymerization ratio
  • p is a numerical value of 10 mass% to 80 mass%
  • Q represents a numerical value of 20% to 90% by mass
  • r represents an integer of 1 to 18, and n represents an integer of 1 to 10.
  • L is preferably a branched alkylene group represented by the following formula (W-2).
  • R 5 in formula (W-2) represents an alkyl group having 1 to 4 carbon atoms, and is preferably an alkyl group having 1 to 3 carbon atoms in terms of compatibility and wettability to the coated surface. Two or three alkyl groups are more preferred.
  • the weight average molecular weight (Mw) of the copolymer is more preferably 1,500 or more and 5,000 or less.
  • the addition amount of the surfactant in the colored composition of the present invention is preferably 0.01 to 2.0% by mass, particularly preferably 0.02 to 1.0% by mass, based on the total solid content of the colored composition. Within this range, the coatability and the uniformity of the cured film are good.
  • the coloring composition of the present invention may contain an adhesion improving agent.
  • the adhesion improver is an inorganic substance that serves as a support, for example, a compound that improves adhesion between a silicon compound such as glass, silicon, silicon oxide, and silicon nitride, gold, copper, aluminum, and the cured film of the colored composition layer. is there.
  • Specific examples include silane coupling agents.
  • the silane coupling agent as the adhesion improving agent is for the purpose of modifying the interface, and any known silane coupling agent can be used without any particular limitation.
  • silane coupling agent a silane coupling agent described in paragraph 0048 of JP-A-2009-98616 is preferable, and ⁇ -glycidoxypropyltrialkoxysilane and ⁇ -methacryloxypropyltrialkoxysilane are more preferable. Further, 3-methacryloxypropyltrimethoxysilane can also be used.
  • the adhesion improver can be used alone or in combination of two or more.
  • the content of the adhesion improving agent in the colored composition of the present invention is preferably 0.1% by mass to 20% by mass and more preferably 0.2% by mass to 5% by mass with respect to the total solid content of the colored composition. .
  • a supplementary crosslinking agent may be used in the colored composition of the present invention to further increase the hardness of the colored layer obtained by curing the colored composition.
  • the crosslinking agent is not particularly limited as long as the film can be cured by a crosslinking reaction.
  • a crosslinking agent can be used alone or in combination of two or more.
  • a development accelerator can also be added in order to promote the alkali solubility of the non-exposed area when the colored composition layer is exposed and to further improve the developability of the colored composition.
  • the development accelerator is preferably a low molecular weight organic carboxylic acid compound having a molecular weight of 1000 or less and a low molecular weight phenol compound having a molecular weight of 1000 or less.
  • aliphatic monocarboxylic acids such as formic acid, acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, diethyl acetic acid, enanthic acid, caprylic acid; oxalic acid, malonic acid, succinic acid, Aliphatic dicarboxylic acids such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, brassic acid, methylmalonic acid, ethylmalonic acid, dimethylmalonic acid, methylsuccinic acid, tetramethylsuccinic acid, citraconic acid; Aliphatic tricarboxylic acids such as tricarballylic acid, aconitic acid, camphoric acid; aromatic monocarboxylic acids such as benzoic acid, toluic acid, cumic acid, hemelitic acid, mesitylene acid; phthalic acid, is
  • the colored composition of the present invention may further contain various additives such as fillers, polymer compounds other than those described above, ultraviolet absorbers, antioxidants and the like. Examples of these additives include those described in paragraphs 0155 to 0156 of JP-A No. 2004-295116.
  • the coloring composition of the present invention may contain a light stabilizer described in paragraph 0078 of JP-A No. 2004-295116 and a thermal polymerization inhibitor described in paragraph 0081 of the publication.
  • the coloring composition of the present invention is prepared by mixing the above-described components and optional components as necessary.
  • the components constituting the colored composition may be mixed together, or may be sequentially added 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 colored composition.
  • the colored composition prepared as described above can be used after being preferably filtered using a filter having a pore size of about 0.01 ⁇ m to 3.0 ⁇ m. Since the colored composition of the present invention can form a colored cured film excellent in luminance and contrast, for forming colored pixels such as a color filter used in a liquid crystal display device, printing ink, inkjet ink, and It can be suitably used as a production application for paints and the like.
  • the color filter of the present invention includes a substrate and a colored pixel composed of a colored film formed on the substrate with the colored composition of the present invention.
  • the colored region on the substrate is composed of colored layers such as red (R), green (G), and blue (B) that form each pixel of the color filter.
  • the method for producing a color filter of the present invention includes a colored layer forming step (A) in which a colored layer (colored composition layer) is formed by applying the above-described colored composition on a support, and step (A).
  • An exposure step (B) for pattern-like exposure to the formed colored layer and a development step (C) for developing the exposed colored layer to form a pattern are included.
  • the aspect which further provided the post-baking (post-heating process) (D) which heat-processes with respect to the coloring pattern obtained at the process (C) is preferable. Furthermore, it is also possible to provide a step (post-exposure) for irradiating the colored pattern with ultraviolet rays between the development step and the post-bake step.
  • the method for producing a color filter of the present invention comprises a step of applying the composition of the present invention on a support to form a colored composition layer, a step of exposing the colored composition layer in a pattern, and an unexposed portion. It is also preferable to include a step of developing and removing to form a colored pattern.
  • COA color filter on array
  • ⁇ Conventional Color Filter Manufacturing Method >> -Process (A)-
  • the above-described colored composition of the present invention is applied onto a support by a coating method such as spin coating, slit coating, cast coating, roll coating, bar coating, and inkjet. Then, a colored layer is formed, and then the colored layer is dried by heating (prebaking) or vacuum drying.
  • the support include sodium glass, alkali-free glass, borosilicate glass, quartz glass, silicon substrate, and resin substrate used for liquid crystal display devices.
  • a driving substrate for a thin film transistor (TFT) liquid crystal display device is used for a COA liquid crystal display device.
  • an undercoat layer, an interlayer insulating film, or the like may be provided on these supports, if necessary, in order to improve adhesion to the upper layer, prevent diffusion of substances, or planarize the surface.
  • the pre-baking condition include a condition of heating at 70 to 130 ° C. for about 0.5 to 15 minutes using a hot plate or an oven.
  • the thickness of the colored layer formed with a coloring composition is suitably selected according to the objective. In the color filter for liquid crystal display devices, the range of 0.2 ⁇ m to 5.0 ⁇ m is preferable, and the range of 1.0 ⁇ m to 4.0 ⁇ m is more preferable.
  • the thickness of the pixel film is preferably in the range of 0.3 ⁇ m to 5.0 ⁇ m, and more preferably in the range of 0.5 ⁇ m to 3.5 ⁇ m.
  • the thickness of a colored layer is a film thickness after prebaking.
  • i-line As light or radiation applicable to exposure, g-line, h-line, i-line and various laser beams are preferable, and i-line is particularly preferable.
  • i-line When using the i-line to the irradiation light is preferably irradiated at an exposure dose of 5mJ / cm 2 ⁇ 500mJ / cm 2.
  • exposure light sources ultra-high pressure, high pressure, medium pressure, low pressure mercury lamps, chemical lamps, carbon arc lamps, xenon lamps, metal halide lamps, various laser light sources, and the like can be used.
  • the colored layer after exposure is developed with a developer.
  • a developer dissolves the uncured portion of the colored layer and does not dissolve the cured portion
  • a combination of various organic solvents or an alkaline aqueous solution can be used.
  • the alkali concentration is preferably adjusted to pH 10-13.
  • alkaline aqueous solution examples include sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, sodium oxalate, sodium metasuccinate, aqueous ammonia, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethyl.
  • alkaline aqueous solutions such as ammonium hydroxide, choline, pyrrole, piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene.
  • an organic alkaline developer is particularly desirable as the developer from the viewpoint of not causing damage to the underlying circuit.
  • the development time is preferably from 30 seconds to 300 seconds, and more preferably from 30 seconds to 120 seconds.
  • the development temperature is preferably 20 ° C. to 40 ° C., more preferably 20 ° C. to 30 ° C.
  • Development can be performed by a paddle method, a shower method, a spray method, or the like.
  • -Process (D)- It is preferable to further heat-treat the colored pattern after development or the colored pattern subjected to post-exposure by ultraviolet irradiation as described above.
  • the color pattern By heating the formed color pattern (so-called post-bake process), the color pattern can be further cured.
  • 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-described step (A), step (B), step (C), and step (D) may be repeated according to the desired number of colors.
  • the step (D) may be performed, or formation, exposure, and exposure of all the color layers having a desired number of colors. After the development is completed, the step (D) may be performed collectively.
  • a color filter which is a more preferable aspect as a color filter constituted using the colored composition of the present invention, a method for producing the color filter, and details relating to the production of COA using these will be described.
  • the color filter of the present invention by the COA method, it can be produced as follows. After applying the composition of the present invention containing a colorant on the TFT substrate to form a coating film of the composition, the coating film is subjected to pattern exposure, alkali development, post-baking treatment, etc. to form each pixel. . Next, after sputtering a transparent electrode (ITO) film on each of the pixels, a positive photoresist coating film is formed, pattern exposure and development are performed on the photoresist film, and the necessary ITO is etched to form a pixel electrode pattern. After the formation, the photoresist film remaining on the pixel electrode pattern is removed with a remover to obtain a COA color filter.
  • ITO transparent electrode
  • a coating film In order to form a coating film by applying the composition of the present invention, it is applied to a substrate directly or via another layer by spin coating (spin coating), slit coating, casting coating, roll coating, or the like, What is necessary is just to dry (pre-bake).
  • the composition layer coated on the substrate can be dried (prebaked) at a temperature of 50 ° C. to 140 ° C. for 10 to 300 seconds using a hot plate, oven or the like.
  • slit coating is also effective as a method for forming a coating film, and this coating method is becoming common.
  • the pattern exposure of the coating film is made up of pixels of each color (three colors or four colors) by exposing through a predetermined mask pattern, curing only the coating film portion irradiated with light, and developing with a developer. This can be done by forming a patterned film.
  • radiation that can be used in exposure ultraviolet rays such as g-line and i-line are particularly preferably used.
  • an alkali development treatment in the case of the negative type, the uncured portion that has not been exposed is eluted in the alkaline aqueous solution, and only the photocured portion remains.
  • the developer an organic alkali developer that does not damage the underlying circuit or the like is desirable.
  • the development temperature is usually 20 ° C.
  • the development time is 20 to 90 seconds.
  • the alkali include ammonia water, ethylamine, diethylamine, dimethylethanolamine, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, choline, pyrrole,
  • concentration of an organic alkaline compound such as piperidine, 1,8-diazabicyclo- [5,4,0] -7-undecene is 0.001% by mass to 10% by mass, preferably 0.01% by mass to 1% by mass.
  • an alkaline aqueous solution diluted with pure water can be used.
  • the developer is generally washed (rinsed) with pure water after development. Next, excess developer is washed away and dried, followed by heat treatment (post-bake). In this way, the above process can be repeated sequentially for each color to produce a cured coating. Thereby, a color filter is obtained.
  • the post-baking is a heat treatment after development for complete curing, and usually a heat curing treatment at 200 ° C. to 240 ° C. is performed.
  • This post-bake treatment is performed continuously or batchwise by using a heating means such as a hot plate, a convection oven (hot air circulation dryer), a high-frequency heater, or the like so that the coating film after development is in the above-described condition. be able to.
  • a transparent electrode (ITO) film is formed on the formed pixel by sputtering, a positive photoresist film is further formed thereon, pattern exposure and development are performed, and then unnecessary with chemicals such as hydrofluoric acid. ITO is etched to form pixel electrodes.
  • a positive photoresist having etching resistance is required.
  • a well-known method can be normally used for pattern exposure, image development, and etching without a restriction
  • the positive resist remaining on the formed pixel electrode is quickly stripped and removed with a stripping solution. There is no restriction
  • a typical stripping solution includes a mixed solvent of monoethanolamine (MEA) and dimethyl sulfoxide (DMSO).
  • MEA monoethanolamine
  • DMSO dimethyl sulfoxide
  • the color filter of the present invention is usually used in various display devices such as a TFT liquid crystal display device having the structure disclosed in FIG. 1 of JP-A-9-31347.
  • the color filter obtained as described above is suitable for a COA type image display device because it can be easily aligned and can increase the aperture ratio.
  • the pixel is formed using the composition of the present invention, the resistance to the stripping solution is high, so that the yield rate is high and the production efficiency is also high.
  • heat discoloration, low dielectric constant, film thickness uniformity, resolution, voltage holding ratio, light resistance and the like normally required for color filters are also good.
  • the structure of the color filter is composed of a pixel film formed of a coating film of a pixel composition and the pixel protective film composition formed on the pixel film, in contrast to the form in which the pixel has only one layer as described above.
  • Two layers of a pixel protective film are provided between the substrate and the pixel electrode.
  • the film thickness of the pixel film is preferably 0.3 ⁇ m to 5.0 ⁇ m, and more preferably 0.5 ⁇ m to 3.5 ⁇ m. The higher the coating thickness, the higher the chromaticity can be achieved. However, the thicker the coating thickness, the lower the resolution of the contact hole.
  • the film thickness of the pixel protective film is preferably 0.2 ⁇ m to 5.0 ⁇ m, and more preferably 0.2 ⁇ m to 3.0 ⁇ m. Further, it is desirable that the unevenness of the underlying pixel is flattened so that the surface is smooth.
  • the color filter obtained by the method for producing a color filter of the present invention is excellent in luminance and contrast because it uses the colored composition of the present invention.
  • the display device of the present invention includes the color filter of the present invention.
  • a liquid crystal display liquid crystal display device; LCD
  • organic EL display organic EL display device
  • a liquid crystal projector liquid crystal projector
  • display device for a game machine a display device for a portable terminal such as a mobile phone.
  • Display devices such as digital camera display devices and car navigation display devices, particularly color display devices are suitable.
  • the color filter of the present invention is used in an organic EL display device, a liquid crystal display device or the like, it is possible to display an image with high luminance and excellent spectral characteristics and contrast.
  • Liquid crystal display device A liquid crystal display device using the color filter of the present invention will be described.
  • organic EL display devices and liquid crystal display devices and details of each display device see, for example, “Electronic Display Devices (Akio Sasaki, published by Kogyo Kenkyukai 1990)”, “Display Devices (written by Junaki Ibuki, Sangyo Tosho (issued in 1989) ”.
  • the liquid crystal display device is described in, for example, “Next-generation liquid crystal display technology (edited by Tatsuo Uchida, published by Kogyo Kenkyukai 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 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 is applied to a liquid crystal display device with a wide viewing angle, such as a horizontal electric field driving method such as IPS and a pixel division method such as MVA, STN, TN, VA, OCS, FFS, and R-OCB. it can.
  • the color filter of the present invention can also be used for a COA (Color-filter On Array) system.
  • the color filter of the present invention When the color filter of the present invention is used for a liquid crystal display device, a high contrast can be realized when combined with a conventionally known three-wavelength tube of a cold cathode tube, and further, red, green and blue LED light sources (RGB-LED).
  • RGB-LED red, green and blue LED light sources
  • the composition of the present invention can be preferably used as a solid-state imaging device.
  • the solid-state imaging device of the present invention includes the color filter of the present invention.
  • the configuration of the solid-state imaging device is a configuration provided with a color filter manufactured using the composition of the present invention, and is not particularly limited as long as the configuration functions as a solid-state imaging device. Can be mentioned.
  • a transfer electrode made of a plurality of photodiodes and polysilicon constituting a light receiving area of a solid-state imaging device (CCD image sensor, CMOS image sensor, etc.) is provided on a support, and the photodiode and the transfer electrode are provided on the support.
  • Example 2 to 21 Colored compositions 2 to 21 were prepared in the same manner as in Example 1 except that the dyes (1A) and (1B) used in Example 1 were changed as described in the following table.
  • Example 22> Preparation of blue pigment dispersion- -Pigment adjustment- C.
  • 100 parts of Pigment Blue 15: 6 (product name: Fastogen Blue EP-193), 400 parts of sodium chloride and 140 parts of diethylene glycol were charged into a table kneader (manufactured by Irie Shokai Co., Ltd.) and kneaded for 10 hours.
  • this kneaded product was stirred and mixed with water using a dissolver (manufactured by Nippon Seiki Seisakusho Co., Ltd.), and then filtered and washed repeatedly to remove sodium chloride and the solvent to obtain a water cake of a coloring material.
  • ⁇ Precise dispersion> The dispersion after the coarse dispersion was taken out, and 30 parts of propylene glycol monomethyl ether acetate was added to 100 parts of the dispersion and mixed. Then, it disperse
  • Example 23 ⁇ Examples 23 and 24>
  • coloring compositions 23 and 24 were prepared in the same manner as in Example 22 except that the dye (2A) and the dye (1B) were changed as shown in the following table.
  • Comparative Examples 2 and 3 Colored compositions of Comparative Examples 2 and 3 were prepared in the same manner as Comparative Example 1 except that the dyes (7A) and (1B) used in Comparative Example 1 were changed as described in the following table.
  • 1A to 8A and 1B to 6B described in the dye A and the dye B represent the dyes 1A to 8A and 1B to 6B described above.
  • the performance of the produced colored composition was evaluated as follows. -Formation of colored composition layer (colored layer)- On the glass (# 1737; made by Corning) board
  • the colored layer on which the latent image was formed was shower-developed for 45 seconds using an aqueous solution of sodium carbonate / sodium bicarbonate (concentration: 2.4 mass%, 26 ° C.), and then rinsed with running water for 20 seconds. And then air blow dried. The dried film was baked at 230 ° C. for 20 minutes in a clean oven to obtain a colored layer.
  • Comparative Example 2 in which dye A was not completely dissolved and evaluated in a dispersed state, there was no problem with respect to liquid crystal specific resistance, PGMEA resistance and light resistance, but the dye used was propylene glycol which is generally used for color resists Since it was insoluble in monomethyl ether acetate, it was found that the luminance was greatly reduced.
  • Comparative Example 3 using a coloring composition that does not contain at least one purple colorant selected from a xanthene dye, a pyromethene dye, and a tetraazaporphyrin dye, the light resistance and liquid crystal specific resistance are low, and the hue is sRGB. It turned out that it was difficult to match such a general color.
  • Example 25 -Production of liquid crystal display devices-
  • a color filter was manufactured by the following method, a liquid crystal display device using the color filter was manufactured, and display characteristics were evaluated.
  • -Preparation of red coloring composition R- The following red pigment dispersion composition was mixed, and the rotational speed was 3,000 r.m. using a homogenizer. p. m. For 3 hours.
  • the mixed solution thus obtained was further subjected to dispersion treatment for 12 hours using a bead disperser disperse mat (manufactured by GETZMANN) using 0.3 mm ⁇ zirconia beads, and then further a high-pressure disperser NANO-3000-10 with a decompression mechanism.
  • photopolymerization initiator 2- (o-chlorophenyl) -4,5-diphenylimidazolyl dimer) 3.1 parts sensitizing dye: 4,4′-bis (diethylamino) benzophenone 4.2 Part: Hydrogen donating compound: 2.1 parts of 2-mercaptobenzothiazole, Polymerization inhibitor: 0.001 part of p-methoxyphenol, Fluorosurfactant (trade name: Megafac R08 manufactured by DIC Corporation) 0.5 Parts ⁇ Propylene glycol monomethyl ether acetate 60 parts
  • green coloring composition G In preparation of the red coloring composition R, C.I. I. Pigment Red 254 instead of C.I. I. Pigment Green 58 (103 copies), C.I. I. Pigment Red 177 instead of C.I. I. A green coloring composition G was prepared in the same manner except that 19 parts of Pigment Yellow 150 was used.
  • a black colored composition K was prepared with the following composition.
  • the alkali-free glass substrate was cleaned with a UV cleaning apparatus, then brush-cleaned with a cleaning agent, and further ultrasonically cleaned with ultrapure water.
  • the substrate was heat treated at 120 ° C. for 3 minutes to stabilize the surface state, and then the substrate was cooled and adjusted to 23 ° C.
  • the black colored composition K was applied on a glass substrate coater (trade name: MH-1600, manufactured by FS Asia Co., Ltd.) having a slit nozzle on the substrate.
  • KOH KOH-based developer
  • CDK-1 a nonionic surfactant
  • heat treatment was performed at 220 ° C. for 30 minutes to form a black matrix.
  • -RGB pixel formation The red colored composition R, the green colored composition G, and the blue photosensitive composition prepared in Example 22 were sequentially laminated and patterned on the glass substrate on which the black matrix was formed, in the same process as when the black matrix was formed. Thus, a color filter of RGB three-color pixels was obtained. At this time, the thickness of the colored portion of each color of RGB was 1.6 ⁇ m.
  • -Formation of ITO electrode The glass substrate on which the color filter was formed was placed in a sputtering apparatus, and 1300 mm thick ITO was vacuum-deposited at 100 ° C., and then annealed at 240 ° C. for 90 minutes to crystallize the ITO to form an ITO transparent electrode.
  • protrusions for controlling liquid crystal alignment- Protrusions for controlling the alignment of liquid crystals were formed on the ITO transparent electrode on which the spacers were formed, using the following coating liquid for positive photosensitive resin layer. However, the following methods were used for exposure, development, and baking.
  • a proximity exposure machine (manufactured by Hitachi High-Tech Electronics Engineering Co., Ltd.) is arranged so that the predetermined photomask is at a distance of 100 ⁇ m from the surface of the photosensitive resin layer, and the irradiation energy is 150 mJ / Proximity exposure was performed at cm 2 .
  • a 2.38% tetramethylammonium hydroxide aqueous solution was developed by spraying it on a substrate at 33 ° C. for 30 seconds in a shower type developing device.
  • the liquid crystal alignment control protrusions made of the photosensitive resin layer patterned into a desired shape are formed on the color filter side substrate.
  • a display device substrate was obtained.
  • the liquid crystal display device substrate on which the liquid crystal alignment control protrusion was formed was baked at 230 ° C. for 30 minutes to form a cured liquid crystal alignment control protrusion on the liquid crystal display device substrate.
  • the liquid crystal display device produced as described above has high contrast and brightness, and is found to be suitable as a display device.
  • the evaluation was performed using an MVA mode liquid crystal display device.
  • the colored composition of the present invention for a liquid crystal display device of another mode or a color filter of an organic EL display it is equally good. It seems that image quality can be obtained.

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JP2016124979A (ja) * 2014-12-26 2016-07-11 大日本印刷株式会社 色材分散液、カラーフィルター用着色樹脂組成物、カラーフィルター、液晶表示装置、及び発光表示装置
TWI647283B (zh) * 2016-01-08 2019-01-11 南韓商Ｌｇ化學股份有限公司 化合物、含有其的彩色組成物、含有其的樹脂組成物、彩色濾光片以及顯示裝置
JP2017128709A (ja) * 2016-01-14 2017-07-27 東友ファインケム株式会社Dongwoo Fine−Chem Co., Ltd. 染料溶解液の製造方法
CN107168011A (zh) * 2016-03-07 2017-09-15 东友精细化工有限公司 青色感光性树脂组合物、包含其的青色滤色器和显示装置
CN107168011B (zh) * 2016-03-07 2021-04-13 东友精细化工有限公司 青色感光性树脂组合物、包含其的青色滤色器和显示装置
TWI636979B (zh) * 2016-08-19 2018-10-01 Ｌｇ化學股份有限公司 化合物、包含其的著色劑組成物與包含其的樹脂組成物、彩色濾光片及顯示器裝置
JP2018059098A (ja) * 2016-10-06 2018-04-12 住友化学株式会社 着色硬化性樹脂組成物
CN108732867A (zh) * 2017-04-20 2018-11-02 三星Sdi株式会社 感光性树脂组合物、使用其的感光性树脂层以及滤色器
CN112154167A (zh) * 2018-07-27 2020-12-29 株式会社艾迪科 组合物、固化物、光学滤波器及固化物的制造方法
CN112154167B (zh) * 2018-07-27 2023-08-22 株式会社艾迪科 组合物、固化物、光学滤波器及固化物的制造方法
CN112980213A (zh) * 2019-12-17 2021-06-18 保土谷化学工业株式会社 呫吨色素、含有该色素的着色组合物、滤色器用着色剂及滤色器以及该色素的制造方法

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