Classifications

• • 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
  • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
• • 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
  • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
  • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
• • 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
• • G—PHYSICS
  • G02—OPTICS
  • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
  • G02B5/00—Optical elements other than lenses
  • G02B5/20—Filters
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
• • G—PHYSICS
  • G02—OPTICS
  • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
  • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
  • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
  • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
  • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
  • G02F1/1333—Constructional arrangements; Manufacturing methods
  • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
  • G02F1/133509—Filters, e.g. light shielding masks
  • G02F1/133514—Colour filters
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
  • G03F7/0007—Filters, e.g. additive colour filters; Components for display devices
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
  • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
• • G—PHYSICS
  • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
  • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
  • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
  • G03F7/004—Photosensitive materials
  • G03F7/09—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers
  • G03F7/105—Photosensitive materials characterised by structural details, e.g. supports, auxiliary layers having substances, e.g. indicators, for forming visible images
• • G—PHYSICS
  • G09—EDUCATION; CRYPTOGRAPHY; DISPLAY; ADVERTISING; SEALS
  • G09F—DISPLAYING; ADVERTISING; SIGNS; LABELS OR NAME-PLATES; SEALS
  • G09F9/00—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements
  • G09F9/30—Indicating arrangements for variable information in which the information is built-up on a support by selection or combination of individual elements in which the desired character or characters are formed by combining individual elements

Definitions

• the present invention relates to a colored curable resin composition, a color filter, and a display device.
• the color filter used for display apparatuses such as a liquid crystal display device, an electroluminescent display device, and a plasma display, and solid-state image sensors, such as CCD and CMOS sensors, is manufactured with colored curable resin composition.
• the composition containing the compound represented by a following formula as a coloring agent is known (patent document 1).
• Patent Document 1 Japanese Unexamined Patent Publication No. 2015-60154
• the color filter formed from the said colored curable resin composition conventionally known was not able to satisfy lightness.
• the gist of the present invention is as follows.
• a coloring agent contains the compound represented by Formula (I) and a red pigment (except the compound represented by Formula (I)),
• Colored curable resin composition whose content rate of a red pigment is 10 mass% or more and 95 mass% or less with respect to coloring agent whole quantity.
• R 1 to R 11 each independently represent a hydrogen atom, a halogen atom, a saturated hydrocarbon group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group and the aryl group is halogen It may be substituted by an atom.
• R 12 to R 15 each independently represent a hydroxyl group, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and the hydrogen atom contained in the saturated hydrocarbon group is a halogen atom.
• the hydrogen atom contained in the said phenyl group and said benzyl group may be substituted, and may be substituted by the C1-C4 alkyl group, a halogen atom, a cyano group, or a vinyl group.
• R 1 and R 13 , R 2 and R 12 , R 4 and R 15, and R 5 and R 14 may be linked to each other to form a six-membered ring containing a nitrogen atom, and R 12 and R 13 and R 14 and R 15 may be connected to each other to form a 3 to 6 membered heterocycle containing a nitrogen atom.
• a q- represents a q-valent anion, and q represents 1 or 2.
• p represents the coefficient by which the compound represented by Formula (I) maintains the charge to be neutral.
• a display device comprising the color filter described in [3].
• the color filter excellent in brightness can be formed.
• the colored curable resin composition of this invention is a coloring agent (henceforth a coloring agent (A)), resin (henceforth may be called resin (B)), a polymeric compound (henceforth, a polymeric compound (C ) And a polymerization initiator (hereinafter may be referred to as a polymerization initiator (D)).
• the coloring agent (A) contains the compound represented by Formula (I) and a red pigment (except the compound represented by Formula (I)), and the content rate of a red pigment is 10 mass% or more with respect to the coloring agent whole quantity 95 It is mass% or less.
• the colored curable resin composition of this invention contains a solvent further.
• the colored curable resin composition of this invention may also contain a leveling agent.
• a coloring agent (A) contains the compound represented by Formula (I), and a red pigment (except the compound represented by Formula (I)).
• the compound represented by Formula (I) is as follows.
• R 1 to R 11 each independently represent a hydrogen atom, a halogen atom, a saturated hydrocarbon group having 1 to 8 carbon atoms or an aryl group having 6 to 20 carbon atoms, and the hydrogen atom contained in the saturated hydrocarbon group and the aryl group is halogen It may be substituted by an atom.
• R 12 to R 15 each independently represent a hydroxyl group, a halogen atom, a cyano group, a nitro group, a saturated hydrocarbon group having 1 to 8 carbon atoms, a phenyl group or a benzyl group, and the hydrogen atom contained in the saturated hydrocarbon group is a halogen atom.
• the hydrogen atom contained in the said phenyl group and said benzyl group may be substituted, and may be substituted by the C1-C4 alkyl group, a halogen atom, a cyano group, or a vinyl group.
• R 1 and R 13 , R 2 and R 12 , R 4 and R 15, and R 5 and R 14 may be linked to each other to form a six-membered ring containing a nitrogen atom, and R 12 and R 13 and R 14 and R 15 may be connected to each other to form a 3 to 6 membered heterocycle containing a nitrogen atom.
• a q- represents a q-valent anion, and q represents 1 or 2.
• p represents the coefficient by which the compound represented by Formula (I) maintains the charge to be neutral.
• the saturated hydrocarbon group having 1 to 8 carbon atoms representing R 1 to R 15 may be any of linear, branched and cyclic.
• Examples of the linear or branched saturated hydrocarbon group include linear alkyl groups such as methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group and octyl group; isopropyl group, isobutyl group, isopentyl group and neopentyl group And branched alkyl groups such as 2-ethylhexyl group and the like.
• Carbon number of the said saturated hydrocarbon group becomes like this.
• it is 1-6, Preferably it is 1-4.
• the cyclic saturated hydrocarbon group may be monocyclic or polycyclic.
• Cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group, are mentioned as said cyclic saturated hydrocarbon group.
• Carbon number of the said cyclic saturated hydrocarbon group becomes like this. Preferably it is 3-8, More preferably, it is 6-8.
• a linear saturated hydrocarbon group is preferable and a methyl group, an ethyl group, and a propyl group are especially preferable.
• Examples of the aryl group having 6 to 20 carbon atoms for R 1 to R 11 include a phenyl group, tolyl group, xylyl group, naphthyl group, anthryl group, phenanthryl group, biphenyl group, terphenyl group, and the like, and preferably a phenyl group. , Naphthyl group, tolyl group, xylyl group, and particularly preferably phenyl group.
• the said aryl group is C6-C20, Preferably it is C6-C15, More preferably, it is C6-C12.
• the hydrogen atom contained in the said saturated hydrocarbon group and the said aryl group may be substituted by the halogen atom.
• halogen atom examples include fluorine, chlorine, bromine and iodine.
• the halogen atom is preferably substituted to form perfluoroalkyl units such as trifluoromethyl units, pentafluoroethyl units, and heptafluoropropyl units.
• the compound represented by Formula (I) has 1 or more and 5 or less halogen atoms, It is more preferable to have 1 or more and 3 or less halogen atoms, It is further more preferable to have 1 or 2 halogen atoms.
• the said halogen atom may contain what the hydrogen atom substituted.
• R 1 ⁇ R 11 is preferably a halogen atom, and at least one of R 7 ⁇ R 11 is more preferably a halogen atom, and either one of R 7 ⁇ R 11 is It is more preferable that it is a halogen atom.
• R 7 and R 8 , R 7 and R 9 , R 7 and R 10 , R 7 and R 11 , R 8 and R 9 , R 8 and R 10 , R 8 and R 11 , R 9 and R 10 , R 9 and R 11 , or R 10 and R 11 are more preferably halogen atoms.
• R 7 , R 7 and R 8 , R 7 and R 9 , R 9 and R 11 are more preferably halogen atoms, and R 7 , R 7 and R 8 , R 9 and R 11 are halogen atoms Is particularly preferred.
• halogen atom examples include fluorine, chlorine, bromine and iodine, but most preferably chlorine.
• the hydrogen atom contained in the phenyl group and the benzyl group may be substituted with an alkyl group having 1 to 4 carbon atoms, a halogen atom, a cyano group, or a vinyl group.
• the C1-C4 alkyl group which the hydrogen atom contained in the phenyl group and benzyl group of R ⁇ 12> -R ⁇ 15> may be substituted, The same thing as a C1-C4 thing among the said C1-C8 saturated hydrocarbon groups is mentioned.
• R ⁇ 1> and R ⁇ 13> , R ⁇ 2> and R ⁇ 12> , R ⁇ 4> and R ⁇ 15> , R ⁇ 5> and R ⁇ 14> may respectively connect and may form the six-membered ring containing a nitrogen atom.
• 6-membered ring As said 6-membered ring, a tetrahydropyridine ring, a pyridine ring, a pyrimidine ring, a quinoline ring, an isoquinoline ring, etc. are mentioned.
• R ⁇ 12> and R ⁇ 13> , R ⁇ 14> and R ⁇ 15> may respectively connect and may form the 3-6 membered heterocyclic ring containing a nitrogen atom.
• a pyrrolidine ring As said 3-6 membered hetero ring, a pyrrolidine ring, a morpholine ring, a piperidine ring, a piperazine ring, a thiomorpholine ring, a pyrrole ring, an imidazole ring, an imidazolidine ring, a pyrazolidine ring, an isothiazoline
• Nitrogen-containing heterocycles such as a Dean ring
• the nitrogen-containing aliphatic heterocycle which has only one nitrogen atom as hetero atoms, such as a pyrrolidine ring and a piperizine ring is mentioned.
• R 1 to R 6 are all hydrogen atoms, at least one of R 7 to R 11 is a halogen atom, and R 12 to R 15 are each independently a saturated hydrocarbon group having 1 to 8 carbon atoms,
• R 1 to R 6 are all hydrogen atoms, one or two of R 7 to R 11 are halogen atoms, and R 12 to R 15 are each independently a linear saturated hydrocarbon group having 1 to 8 carbon atoms. Desirable,
• R 1 to R 6 are all hydrogen atoms, any one of R 7 to R 11 is a halogen atom, or R 7 and R 8 , R 7 and R 9 , R 7 and R 10 , R 7 and R 11 , R 8 and R 9 , R 8 and R 10 , R 8 and R 11 , R 9 and R 10 , R 9 and R 11 , or R 10 and R 11 are halogen atoms, and R 12 to R 15 are It is further more preferable that they are each independently a C1-C4 alkyl group.
• R ⁇ 7> -R ⁇ 11> which represent other than a halogen atom are hydrogen atoms.
• a q- represents a q-valent anion, and q represents 1 or 2.
• p represents the coefficient by which the compound represented by Formula (I) keeps electric charge neutral.
• p is preferably 1 to 14, more preferably 1 to 6, still more preferably 1 to 4, still more preferably 1 to 3, and particularly preferably 1 or 2 .
• anion examples include halide anions, other inorganic anions, organic carboxylic acid anions, organic sulfonic acid anions, organic phosphate anions, organic imide acid anions, organic methic acid anions, and organic chromic acid anions.
• inorganic anions examples include perchlorate ions, chlorate ions, thiocyanate ions, hexafluorophosphate ions (hereinafter may be referred to as "anions (VII)”), hexafluoroantimonate ions, tetrafluoroborate ions, and the like. Can be.
• the anion containing at least 1 atom and oxygen atom chosen from the group which consists of tungsten, molybdenum, silicon, and phosphorus is mentioned. From the viewpoint of heat resistance, anions containing tungsten atoms and oxygen atoms are preferred.
• anion (IX) As an anion containing at least one atom and an oxygen atom selected from the group consisting of tungsten, molybdenum, silicon and phosphorus, ⁇ - [PW 12 O 40 ] 3- (hereinafter referred to as "anion (IX)”) Kegin-type tungsten acid ions such as ⁇ - [P 2 W 18 O 62 ] 6- , beta-type tungsten acid ions such as ⁇ - [P 2 W 18 O 62 ] 6- ; ⁇ - [SiW 12 O 40 ] 4-, ⁇ - [SiW 12 O 40] 4-, ⁇ - [SiW 12 O 40] 4- , etc.
• IX anion
• Kane ginhyeong silicon tungstate ions [P 2 W 17 O 61 ] 10-, [P 2 W 15 O 56 ] 12- , [H 2 P 2 W 12 O 48 ] 12- , [NaP 5 W 30 O 110 ] 14- , ⁇ - [SiW 9 O 34 ] 10- , ⁇ - [SiW 10 O 36 ] 8 -, ⁇ - [SiW 11 O 39 ] 8-, ⁇ - [SiW 11 O 39] 8-; [W 6 O 19] 2-, [W 10 O 32] containing tungsten such as 4-, WO 4 2- Isopoly acid ion, a silicate ion, a phosphate ion, etc. are mentioned.
• organic carboxylic acid anion examples include acetate ions, oxalic acid ions, and benzoic acid ions.
• organic sulfonic acid anion examples include methane sulfonic acid ion, dodecyl sulfonic acid ion, benzene sulfonic acid ion, toluene sulfonic acid ion, naphthalene sulfonic acid ion, diphenylamine-4- sulfonic acid ion, 2-amino-4-methyl-5-chlorobenzene sulfonic acid ion, And 2-amino-5-nitrobenzenesulfonic acid ions, phthalocyanine sulfonic acid ions, sulfonic acid ions having a polymerizable substituent, benzenedisulfonic acid anions, naphthalenedisulfonic acid anions and the like.
• organic phosphate anion octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphonic acid ion Etc.
• organic phosphate anion octyl phosphate ion, dodecyl phosphate ion, octadecyl phosphate ion, phenyl phosphate ion, nonylphenyl phosphate ion, 2,2'-methylenebis (4,6-di-t-butylphenyl) phosphonic acid ion Etc.
• organic chromic acid anion bis [2-[(4,5-dihydro-3-methyl-5-oxo-1-phenyl-1H-pyrazol-4-yl) azo] benzoat] chromate ion (hereinafter referred to as "anion” (VIII) ”may be mentioned.
• an inorganic anion, an organic carboxylic acid anion, an organic sulfonic acid anion, an organic imide acid anion, and an organic methionate anion are preferable, and hexafluoro phosphate ions, fluorine-containing organic carboxylic acid anions and fluorine-containing organic
• the sulfonic acid anion, the fluorine-containing organic imide acid anion, and the fluorine-containing organic methionate anion (hereinafter, collectively referred to as fluorine-containing anions) are more preferable.
• CF 3 CO 2 - and an anion represented by Formula (III), (IV), (V) or (VI) are mentioned, for example.
• W 3 and W 4 are, independently of each other, a fluorine atom, or or represent a fluorinated alkyl group having from 1 to 4 carbon atoms, or, W is with the 3 and W 4 fluoride al 1-4C alkanediyl Represents a diary.
• W ⁇ 5> -W ⁇ 7> represents a fluorine atom or a C1-C4 fluorinated alkyl group independently of each other.
• Y ⁇ 1> represents a C1-C4 fluorinated alkanediyl group.
• Y ⁇ 2> represents a C1-C4 fluorinated alkyl group.
• a perfluoroalkyl group is preferable as a C1-C4 fluorinated alkyl group.
• a perfluoroalkyl group is preferable as to the perfluoroalkyl group.
• the perfluoroalkyl group -CF 3, -CF 2 CF 3 , -CF 2 CF 2 CF 3, -CF (CF 3) 2, -CF 2 CF 2 CF 2 CF 3, -CF 2 CF (CF 3 ), and the 2, -C (CF 3) 3.
• perfluoroalkyl roal alkanediyl group are preferable, and -CF 2 -, -CF 2 CF 2 -, -CF 2 CF 2 CF 2 -, -C (CF 3) 2 - , and the like -, -CF 2 CF 2 CF 2 CF 2.
• anion (III) As an anion represented by the formula (III) (hereinafter may be referred to as “anion (III)”), anions represented by the formulas (III-1) to (III-6) (hereinafter referred to as “anion (III-1)) To “anion (III-6)” may be mentioned.
• anion (IV) As an anion represented by Formula (IV) (hereinafter may be called “anion (IV)”), Anion (IV-1) represented by Formula (IV-1) is mentioned.
• anion (V) As an anion represented by the formula (V) (hereinafter may be referred to as “anion (V)”), anion (hereinafter referred to as “anion (V-1)”) represented by formula (V-1) to formula (V-4), respectively. To “anion (V-4)” may be mentioned.
• anion represented by the formula (VI) (hereinafter may be referred to as “anion (VI)")
• anion represented by the formula (VI-1) to the formula (VI-4) (hereinafter referred to as “anion (VI-1)")
• anion (VI-4) To “anion (VI-4)" may be mentioned.
• the fluorine-containing anion may be at least one anion selected from the group consisting of CF 3 CO 2 — , anion (III), anion (IV), anion (V) and anion (VI).
• anion (III), anion (IV), anion (V) and anion (VI) are preferred, CF 3 CO 2 -, an anion (III-2), anions (IV-1), anionic (V-1), anionic (VI-1) anion (VI-2), and anionic (VI-3) are preferred, CF 3 CO 2 -, an anion (III-2), anions (IV-1), anionic (VI-1) it is more preferable.
• the compound represented by Formula (I) is a compound represented by Formula (I-A).
• the compound represented by Formula (I-A) is a compound represented by Formula (I-1)-Formula (I-480).
• the compound represented by Formula (I-1)-Formula (I-240) is preferable, The compound represented by Formula (I-121)-Formula (I-240) is more preferable, Formula (I-136)
• the content rate of the compound represented by Formula (I) is 5 mass% or more and 90 mass% or less with respect to a coloring agent whole quantity, It is more preferable that they are 5 mass% or more and 40 mass% or less, It is 5 mass% or more and 30 mass% or less More preferred.
• the content rate of the compound represented by Formula (I) is 0.5 mass% or more and 20 mass% or less with respect to solid content whole quantity, It is more preferable that they are 1 mass% or more and 15 mass% or less, It is 2 mass% or more and 12 mass% or less More preferred.
• solid content whole quantity in this specification means the quantity remove
• Solid content whole quantity and content of each component with respect to this can be measured by well-known analytical means, such as liquid chromatography or gas chromatography, for example.
• red pigment contained in the colored curable resin composition of this invention a well-known pigment can be used, For example, it is classified in red among the pigment classified by the pigment in the color index (The Society of Dyers and Colorists publication). It can be mentioned. You may combine 2 or more types. However, the compound represented by Formula (I) is excluded.
• red pigments anthraquinone pigments, azo pigments, quinacridone pigments, perylene pigments, and diketopyrrolopyrrole pigments are preferable, and C.I. Pigment Red 177, 179, 202, 208, 242, 254, 269, brominated diketopyrrolopyrrole pigments are preferred, and C.I. Pigment Red 177, 254 and brominated diketopyrrolopyrrole pigments are more preferred.
• it is 10 mass% or more and 95 mass% or less with respect to a coloring agent whole quantity, It is more preferable that it is 30 mass% or more and 90 mass% or less with respect to a coloring agent whole quantity, It is more preferable that it is 50 mass% or more, It is still more preferable that it is 60 mass% or more. .
• the total content rate of the compound represented by Formula (I) and a red pigment is 30 mass% or more with respect to a coloring agent whole quantity, More preferably, 40 mass% or more, More preferably, it is 50 mass% or more, Preferably it is 99 mass% or less, More preferably, it is 95 mass% or less.
• the colored curable resin composition of this invention may contain the coloring agent (Hereinafter, it may be called coloring agent (A1)) other than the compound represented by Formula (I) as a coloring agent (A), and a red pigment. 1 type (s) or 2 or more types of color agents may be contained in the coloring agent (A1).
• a dye or a pigment may be sufficient as a coloring agent (A1).
• the dyes include known dyes described in the color index (Published by The Society of Dyers and Colourists) and the dyeing notes (color dyed yarn).
• an organic solvent soluble dye is preferable. These dyes may use 2 or more types together.
• C.I. Color Index
• a well-known pigment can be used, For example, the pigment classified by the pigment in the color index (The Society of Dyers and Colourists) is mentioned. You may combine 2 or more types. However, the compound represented by Formula (I) is excluded.
• CI Pigment Yellow 1 3, 12, 13, 14, 15, 16, 17, 20, 24, 31, 53, 83, 86, 93, 94, 109, 110, 117, 125, 128, Yellow pigments such as 129, 137, 138, 139, 147, 148, 150, 153, 154, 166, 173, 185, 194, 214;
• Pigment oranges such as pigment orange 13, 31, 36, 38, 40, 42, 43, 51, 55, 59, 61, 64, 65, 71, 73;
• C.I. Violet pigments such as pigment violet 1, 19, 23, 29, 32, 36 and 38;
• a yellow pigment is preferable and C.I. Pigment Yellow 138, 139, 150, 185 is more preferable.
• the content rate becomes like this.
• it is 1 mass% or more and 50 mass% or less with respect to coloring agent whole quantity, More preferably, it is 2 mass% or more and 40 mass% or less, More preferably, it is 5 mass It is more than 35 mass%.
• the content rate of the yellow pigment is preferably 1% by mass or more and 25% by mass or less, more preferably 2% by mass or more and 20% by mass or less, and even more preferably 3% by mass or more and 15% by mass to the total solid content. It is as follows.
• the red pigment, and the pigment (hereinafter may be referred to as a pigment) in the colorant (A1)
• a rosin treatment, a colorant derivative into which an acidic group or a basic group is introduced, or the like may be used.
• Surface treatment used, graft treatment to the surface such as pigments by polymer compounds, etc., atomization treatment by sulfuric acid atomization method, cleaning treatment by organic solvent or water to remove impurities, removal treatment by ion exchange method of ionic impurities, etc. It may be implemented. It is preferable that particle diameters, such as a pigment, are respectively substantially uniform.
• a pigment etc. becomes a state disperse
• Surfactant etc. are mentioned as a dispersing agent, Any surfactant of cationic, anionic, nonionic, and amphoteric may be sufficient. Specifically, surfactant, such as polyester type, polyamine type, and acryl type, etc. are mentioned. As another dispersing agent, you may use resin (B) mentioned later. You may use these dispersing agents individually or in combination of 2 or more types.
• KP made by Shin-Etsu Chemical Co., Ltd.
• Floren made by Kyoeisha Chemical Co., Ltd.
• Solsperth registered trademark
• EFKA registered trademark
• Addisper registered trademark
• Disperbyk registered trademark
• BYK registered trademark
• the usage-amount of a dispersing agent becomes like this.
• it is 100 mass parts or less with respect to 100 mass parts, such as a pigment, More preferably, it is 5 mass parts or more and 70 mass parts or less.
• the usage-amount of a dispersing agent exists in said range, it exists in the tendency for the coloring agent containing liquid of a more uniform dispersion state to be obtained.
• content of a coloring agent (A) is 20 mass% or more and 80 mass% or less normally in solid content whole quantity, Preferably they are 30 mass% or more and 70 mass% or less, More preferably, 40 mass% or more It is 60 mass% or less.
• resin (B) is not specifically limited, It is preferable that it is alkali-soluble resin, At least 1 sort (a) (Hereinafter, "(a)” may be chosen from the group which consists of unsaturated carboxylic acid and unsaturated carboxylic anhydride.
• Resin which has a structural unit derived from the Resin (B) is a structural unit derived from the monomer (b) (Hereinafter, it may be called “(b)”) which has a C2-C4 cyclic ether structure and ethylenically unsaturated bond, (a) Structural unit derived from monomer (c) copolymerizable with (but (a) and (b) is different) (hereinafter may be called “(c)”), and has an ethylenically unsaturated bond in a side chain It is preferable to have at least 1 sort (s) of structural unit chosen from the group which consists of a structural unit.
• (a) examples include acrylic acid, methacrylic acid, maleic anhydride, itaconic anhydride, 3,4,5,6-tetrahydrophthalic anhydride, and succinic acid mono [2- (meth) acrylic acid. Royloxyethyl] etc., Preferably, they are acrylic acid, methacrylic acid, and maleic anhydride.
• (meth) acrylic acid represents at least 1 sort (s) chosen from the group which consists of acrylic acid and methacrylic acid. Notation, such as “(meth) acryloyl” and “(meth) acrylate”, also has the same meaning.
• (b) is a monomer having a C2-C4 cyclic ether structure (for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring) and a (meth) acryloyloxy group Is preferred.
• a C2-C4 cyclic ether structure for example, at least one selected from the group consisting of an oxirane ring, an oxetane ring and a tetrahydrofuran ring
• a (meth) acryloyloxy group Is preferred is preferred.
• glycidyl (meth) acrylate for example, glycidyl (meth) acrylate, vinyl benzyl glycidyl ether, 3, 4- epoxy citric cyclo [5.2.1.0 2,6 ] decyl (meth) acrylate, 3-ethyl -3- (meth) acryloyloxymethyl oxetane, tetrahydrofurfuryl (meth) acrylate, etc. are mentioned,
• glycidyl (meth) acrylate and 3 4- epoxy cyclocyclo [ 5.2.1.0 2,6 ] decyl (meth) acrylate and 3-ethyl-3- (meth) acryloyloxymethyloxetane.
• (c) for example, methyl (meth) acrylate, butyl (meth) acrylate cyclohexyl (meth) acrylate, 2-methylcyclohexyl (meth) acrylate, tricyclo [5.2.1.0 2,6 ]
• styrene vinyl toluene, 2-hydroxyethyl (meth) acrylate, N-phenylmaleimide, N-cyclohexyl maleimide, N-benzyl maleimide, etc. are preferable. .
• Resin which has a structural unit which has ethylenically unsaturated bond in a side chain adds (b) to the copolymer of (a) and (c), or (a) is added to the copolymer of (b) and (c). It can manufacture by making it.
• the said resin may be able to add (a) to the copolymer of (b) and (c), and to make carbonic acid anhydride react further.
• the weight average molecular weight of polystyrene conversion of resin (B) becomes like this.
• it is 3,000-100,000, More preferably, it is 5,000-50,000, More preferably, it is 5,000-30,000.
• Dispersion degree (weight average molecular weight (Mw) / number average molecular weight (Mn)) of resin (B) becomes like this.
• Mw weight average molecular weight
• Mn number average molecular weight
• the acid value of resin (B) is 50-170 mg-KOH / g in solid content conversion, Preferably it is 60-150 mg-KOH / g, More preferably, it is 70-135 mg-KOH / g.
• the acid value is a value measured as the amount (mg) of potassium hydroxide required to neutralize 1 g of the resin (B), and can be obtained by titration using, for example, an aqueous potassium hydroxide solution.
• the content of the resin (B) is preferably 1 to 60% by mass, more preferably 5 to 50% by mass, still more preferably 7 to 40% by mass, based on the total solid content.
• a polymerizable compound (C) is a compound which can superpose
• the compound etc. which have a polymerizable ethylenically unsaturated bond are mentioned, It is preferable.
• a (meth) acrylic acid ester compound is preferable.
• a polymeric compound (C) is a polymeric compound which has 3 or more of ethylenically unsaturated bonds.
• a polymerizable compound trimethylol propane tri (meth) acrylate, pentaerythritol tri (meth) acrylate, pentaerythritol tetra (meth) acrylate, dipentaerythritol penta (meth) acrylate, for example. And dipentaerythritol hexa (meth) acrylate.
• the weight average molecular weight of the polymerizable compound (C) is preferably 150 or more and 2,900 or less, more preferably 250 or more and 1,500 or less.
• the content of the polymerizable compound (C) is preferably 1% by mass or more and less than 30% by mass, more preferably 3% by mass or more and 28% by mass or less, and still more preferably 5% by mass or more, based on the total solid content. It is 20 mass% or less.
• the polymerization initiator (D) may be any compound that can generate an active radical, an acid, or the like by the action of light or heat to initiate polymerization, and any known polymerization initiator can be used without particular limitation.
• produces an active radical it is N-benzoyloxy-1- (4-phenylsulfanylphenyl) butan-1-one-2-imine and N-benzoyloxy-1- (4-phenylsulfur), for example.
• the polymerization initiator is preferably a polymerization initiator containing at least one selected from the group consisting of a triazine compound, an acylphosphine oxide compound, an alkylphenone compound, an O-acyl oxime compound and a biimidazole compound, and an O-acyl oxime
• the polymerization initiator containing a compound is more preferable.
• Content of a polymerization initiator (D) becomes like this. Preferably it is 0.1-30 mass parts with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), More preferably, it is 1-20 mass parts.
• content of a polymerization initiator (D) exists in said range, since it will become high sensitivity and the exposure time tends to be shortened, productivity of a color filter improves.
• the content of the O-acyl oxime compound is preferably 50% by mass or more, more preferably 80% by mass or more, still more preferably 90% by mass or more, and particularly preferably based on the total amount of the polymerization initiator (D). Preferably it is 95 mass% or more.
• the content rate of the O-acyl oxime compound is in the above range, there is a tendency that a high-brightness color filter can be produced even when the sensitivity, developability, and colorant content rate when forming a colored pattern are high.
• the colored curable resin composition of this invention may contain the polymerization start adjuvant.
• a polymerization start adjuvant (D1) is a compound or sensitizer used in order to accelerate superposition
• polymerization start adjuvant (D1) 4,4'-bis (dimethylamino) benzophenone (common name mihiraz ketone), 4,4'-bis (diethylamino) benzophenone, 9,10- dimethoxy anthracene, 2, 4- diethyl thioxanthone N-phenylglycine etc. are mentioned.
• these polymerization start adjuvant (D1) When using these polymerization start adjuvant (D1), its content becomes like this. Preferably it is 0.1-30 mass parts with respect to 100 mass parts of total amounts of resin (B) and a polymeric compound (C), More preferably, it is 1-20 It is a mass part. When the amount of the polymerization start aid (D1) is within this range, the coloring pattern can be formed with higher sensitivity, and the productivity of the color filter tends to improve.
• the colored curable resin composition of this invention contains a solvent.
• Solvent (E) is not specifically limited, The solvent normally used in the said field
• an ester solvent solvent containing -COO- in a molecule and not containing -O-
• an ether solvent solvent containing -O- in a molecule and not containing -COO-
• an ether ester Solvent solvent containing -COO- and -O- in the molecule
• ketone solvent solvent containing -CO- in the molecule and not containing -COO-
• alcohol solvent containing OH in the molecule,- Solvents not containing O-, -CO- and -COO-
• an aromatic hydrocarbon solvent an amide solvent, dimethyl sulfoxide, diacetone alcohol, and the like.
• ester solvents such as ethyl lactate, butyl lactate, methyl 2-hydroxyisobutyrate, n-butyl acetate, ethyl butyrate, butyl butyrate, ethyl pyruvate, methyl acetoacetate, cyclohexanol acetate, and ⁇ -butyrolactone.
• Solvent containing -COO- and not containing -O-) in the molecule ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, 3-methoxy-1-butanol, diethylene glycol Ether solvents such as dimethyl ether and diethylene glycol methyl ethyl ether (solvent containing -O- in the molecule and not containing -COO-);
• Ether ester solvents such as methyl 3-methoxypropionate, ethyl 3-ethoxypropionate, 3-methoxybutyl acetate, propylene glycol monomethyl ether acetate, ethylene glycol monoethyl ether acetate and diethylene glycol monoethyl ether acetate (in the molecule Solvent containing -COO- and -O-);
• Ketone solvents such as 4-hydroxy-4-methyl-2-pentanone, heptanone, 4-methyl-2-pentanone, and cyclohexanone (containing -CO- in the molecule and not containing -COO-) Solvent); alcohol solvents such as butanol, cyclohexanol, and propylene glycol (solvents containing OH in the molecule and not containing -O-, -CO- and -COO-); aromatic hydrocarbon solvents such as toluene and xylene Diacetone alcohol, etc. are mentioned.
• Amide solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, and N-methylpyrrolidone.
• propylene glycol monomethyl ether acetate propylene glycol monomethyl ether
• propylene glycol monomethyl ether ethyl lactate
• cyclohexanone diacetone alcohol
• diacetone alcohol ethyl 3-ethoxypropionate
• the solvent is preferably a mixed solvent containing propylene glycol monomethyl ether acetate.
• examples of the solvent to be combined with propylene glycol monomethyl ether acetate include ethyl lactate, propylene glycol monomethyl ether, 3-ethoxypropionate, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, and dipropylene glycol methyl ether acetate.
• -Methoxybutyl acetate, 3-methoxy-1-butanol, diacetone alcohol, and 4-hydroxy-4-methyl-2-pentanone are preferable, and propylene glycol monomethyl ether, dipropylene glycol methyl ether acetate, Ethyl lactate, 3-methoxybutyl acetate, 3-methoxy-1-butanol, diacetone alcohol and ethyl 3-ethoxypropionate are more preferable, and ethyl lactate and diacetone alcohol are more preferable.
• the total content of the solvent combined with propylene glycol monomethyl ether acetate is preferably 0.1% by mass or more and 50% by mass or less, more preferably 0.3% by mass or more and 40% by mass or less with respect to the total amount of the solvent. Is 0.5 mass% or more.
• the content rate of a solvent (E) becomes like this.
• it is 65-95 mass% with respect to the colored curable resin composition whole quantity of this invention, More preferably, it is 70-92 mass%.
• solid content whole quantity of colored curable resin composition becomes like this.
• it is 5-35 mass%, More preferably, it is 8-30 mass%.
• the colored curable resin composition of this invention may contain additives known in the said technical field, such as a leveling agent, a filler, another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, a chain transfer agent, as needed.
• additives known in the said technical field such as a leveling agent, a filler, another high molecular compound, an adhesion promoter, antioxidant, an optical stabilizer, a chain transfer agent, as needed.
• the colored curable resin composition of this invention can be prepared by mixing a coloring agent (A), resin (B), a polymeric compound (C), a polymerization initiator (D), a solvent (E), and other components as needed. .
• the photolithographic method As a method of manufacturing a coloring pattern with the colored curable resin composition of this invention, the photolithographic method, the inkjet method, the printing method, etc. are mentioned. Especially, the photolithographic method is preferable.
• cured material of the said coloring composition layer can be formed by not using a photomask at the time of exposure, and / or not developing.
• the coloring pattern and colored coating film formed in this way are the color filter of this invention.
• the colored curable resin composition of this invention can produce the color filter excellent in the brightness.
• the said color filter is useful as a color filter used for a display apparatus (for example, a liquid crystal display device, an organic electroluminescent apparatus, an electronic paper, etc.) and a solid-state image sensor.
• Example 1 The compound 1 of Example 1 was changed to the compound 2, and the same operation was performed, and the following compound (I-141) [compound represented by Formula (I-141)] was obtained with a yield of 34.9%.
• Example 1 The compound 1 of Example 1 was changed to the compound 3, and the same operation was performed and the following compound (I-136) [compound represented by Formula (I-136)] was obtained with a yield of 44.0%.
• Example 1 The compound 1 of Example 1 was changed to the compound 3, and the aqueous solution of potassium bis (trifluoromethanesulfonyl) imide was changed to the aqueous solution of potassium hexafluorophosphate, and the same operation was performed to give a yield of 53.0% of the following compound (I-226). [Compound shown by Formula (I-226)] was obtained.
• Example 1 The compound 1 of Example 1 was changed to the compound 4, and the same operation was performed, and the following compound (I-142) [compound represented by Formula (I-142)] was obtained with a yield of 41.8%.
• the following measurement was performed with Japanese spectroscopy agent U-3900. That is, after measuring the base line of chloroform, the measurement sample is placed in a quartz cell having an optical path length of 1 cm, and absorbance is measured at 300 nm / min in the visible light region of 800 to 300 nm at 0.5 nm intervals to obtain a maximum absorbance at 600 to 400 nm. The wavelength was set to lambda max. Moreover, molar extinction coefficient (epsilon) was computed from the absorbance of (lambda) max and its molecular weight using the Beer Lambert's law.
• epsilon molar extinction coefficient
• Sodium tert-amyl alcohol was synthesized by reacting 174 parts of tert-amyl alcohol with 22.2 parts of metallic sodium at 130 ° C. under a nitrogen atmosphere. This was heated to 60 degreeC, 91.0 parts of 4-bromobenzonitrile, 71.05 parts of succinic-acid di-tert- amyl esters, and 108.9 parts of tert- amyl alcohol were added, and it stirred for 2 hours so that liquid temperature might be 85 degrees C or less. The suspension was further stirred for 18 hours or more, and then added to a mixture of 200 parts of methanol, 1000 parts of water, and 49.21 parts of sulfuric acid cooled to ⁇ 10 ° C.
• the mixture was kept at 0 ° C., stirred for 5 hours to complete the reaction, and the solids were filtered out.
• the solid content was alternately washed with methanol and water, and washed repeatedly until the color of the filtrate disappeared and there was no precipitation of the salt. Then, solid content was dried for 18 hours by the 80 degreeC vacuum dryer, and the target red pigment 1 was obtained. The obtained amount was 107 parts.
• Resin (B-1) has the following structural unit.
• the measurement of the weight average molecular weight (Mw) and number average molecular weight (Mn) of resin was performed on condition of the following using GPC method.
• the ratio (Mw / Mn) of the weight average molecular weight and number average molecular weight of polystyrene conversion obtained above was made into dispersion degree.
• Resin (B) Resin (B-1) (solid content conversion)
• the film thickness was measured using the film thickness measuring apparatus (DEKTAK3; the Japan vacuum technology company make). The results are shown in Table 12.
• the color filter excellent in brightness can be formed.

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