WO2015046178A1 - Composition colorante photosensible, matrice à fond noir, espaceur de coloration, dispositif d'affichage d'image, et dispersion de pigment - Google Patents

Composition colorante photosensible, matrice à fond noir, espaceur de coloration, dispositif d'affichage d'image, et dispersion de pigment Download PDF

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WO2015046178A1
WO2015046178A1 PCT/JP2014/075144 JP2014075144W WO2015046178A1 WO 2015046178 A1 WO2015046178 A1 WO 2015046178A1 JP 2014075144 W JP2014075144 W JP 2014075144W WO 2015046178 A1 WO2015046178 A1 WO 2015046178A1
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group
pigment
mass
carbon atoms
coloring composition
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PCT/JP2014/075144
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English (en)
Japanese (ja)
Inventor
大津　猛
良尚 沢井
敦哉 伊藤
善秀 小川
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三菱化学株式会社
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Application filed by 三菱化学株式会社 filed Critical 三菱化学株式会社
Priority to JP2015506015A priority Critical patent/JP6489008B2/ja
Priority to KR1020207007432A priority patent/KR102210576B1/ko
Priority to KR1020227002415A priority patent/KR102485543B1/ko
Priority to KR1020167007364A priority patent/KR102356749B1/ko
Priority to CN201480051237.0A priority patent/CN105556390B/zh
Priority to CN202010078235.8A priority patent/CN111190328B/zh
Priority to KR1020177023321A priority patent/KR101844731B1/ko
Priority to KR1020237018284A priority patent/KR20230085213A/ko
Priority to KR1020227046216A priority patent/KR102540420B1/ko
Publication of WO2015046178A1 publication Critical patent/WO2015046178A1/fr

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C08G59/245—Di-epoxy compounds carbocyclic aromatic
    • 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
    • C09C—TREATMENT OF INORGANIC MATERIALS, OTHER THAN FIBROUS FILLERS, TO ENHANCE THEIR PIGMENTING OR FILLING PROPERTIES ; PREPARATION OF CARBON BLACK  ; PREPARATION OF INORGANIC MATERIALS WHICH ARE NO SINGLE CHEMICAL COMPOUNDS AND WHICH ARE MAINLY USED AS PIGMENTS OR FILLERS
    • C09C1/00—Treatment of specific inorganic materials other than fibrous fillers; Preparation of carbon black
    • C09C1/44—Carbon
    • C09C1/48—Carbon black
    • 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
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133512—Light shielding layers, e.g. black matrix
    • 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
    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031—Organic compounds not covered by group G03F7/029
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/033—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. vinyl polymers
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/038—Macromolecular compounds which are rendered insoluble or differentially wettable
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/09—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
    • 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

Definitions

  • the present invention relates to a photosensitive coloring composition, a black matrix, a coloring spacer, and an image display device.
  • a photosensitive coloring composition excellent in shielding property and plate-making characteristic, and its use.
  • the black matrix for a liquid crystal display element is used to prevent light leakage from the drive electrodes in the liquid crystal display element.
  • a black matrix is a pattern of a light-shielding material in the form of stripes or lattices formed by using a photolithography method on a transparent substrate such as glass or plastic sheet that is paired with a TFT (Thin Film Transistor) element substrate. is there.
  • a color filter on array method COA method
  • a black matrix on array method (BOA method) in which only the black matrix is provided on the TFT element substrate side has been proposed.
  • the black matrix has a volume resistivity above a certain level and a relative dielectric constant below a certain level so as not to cause a short circuit of an electric circuit even if it is directly mounted on a TFT element. Is required.
  • a black matrix using a plurality of types of organic coloring pigments and carbon black as a pigment has been proposed (for example, see Patent Document 1).
  • photosensitive compositions for black matrix using organic black pigments as pigments are also known.
  • aniline black for example, see Patent Document 2
  • perylene black for example, see Patent Document 3
  • organic pigments for example, Patent Document 4
  • This document describes that the pigment is used for forming a red layer, a blue layer and a green layer of a color filter.
  • this pigment is used also as an organic black pigment for electrophoretic displays (for example, refer patent document 5).
  • Japanese Unexamined Patent Publication No. 2009-75446 Japanese Laid-Open Patent Publication No. 8-44049 Japanese Unexamined Patent Publication No. 2006-235153 Japanese National Table 2002-528448 Japan Special Table 2012-515240
  • the photosensitive composition described in Patent Document 1 has a low shielding ratio (optical density) of the organic coloring pigment, and the film thickness is increased in order to obtain a sufficient optical density. I found it necessary to do.
  • the aniline black and perylene black described in Patent Documents 2 and 3 have poor dispersibility, and it is necessary to use a large amount of a dispersant to disperse, which may cause problems in plate-making properties. I found out. In addition, it was found that the shielding rate (optical density) was not sufficient.
  • Patent Documents 4 and 5 have no description or suggestion about using a bis-oxodihydro-indoleylene-benzofuran colorant as a shielding agent used in an image display device, and when used as a shielding agent used in an image display device.
  • the characteristics such as the optical density, dispersibility and plate-making property are also unknown.
  • the present invention has been made in view of the above-described conventional circumstances, and provides a photosensitive coloring composition having excellent light-shielding properties, excellent dispersibility and plate making properties, and exhibiting a sufficiently low relative dielectric constant. With the goal.
  • the organic coloring pigment having a specific structure is used as the coloring material in the photosensitive coloring composition, and a specific dispersant is used.
  • the present invention has the following configurations [1] to [17].
  • a photosensitive coloring composition containing at least (A) a coloring material, (B) a dispersant, (C) an alkali-soluble resin, and (D) a photopolymerization initiator, wherein (A) the coloring material is (A-1) an organic black pigment that is a compound represented by the following general formula (1), a geometric isomer, a salt thereof, or a salt of the geometric isomer, and the dispersant (B) is 4
  • a photosensitive coloring composition comprising a polymer dispersant having a quaternary ammonium base as a functional group.
  • R 1 and R 6 are each independently a hydrogen atom, CH 3 , CF 3 , a fluorine atom or a chlorine atom;
  • R 2 , R 3 , R 4 , R 5 , R 7 , R 8 , R 9, and R 10 are independently of each other hydrogen atoms, halogen atoms, R 11 , COOH, COOR 11 , COO ⁇ , CONH 2 , CONHR 11 , CONR 11 R 12 , CN, OH, OR 11.
  • R 10 may be directly bonded to each other, or may be bonded to each other by an oxygen atom, sulfur atom, NH or NR 11 bridge; R 11 and R 12 are independently of each other; An alkyl group having 1 to 12 carbon atoms,
  • R 2 , R 4 , R 5 , R 7 , R 9 and R 10 are each independently a hydrogen atom, a fluorine atom or a chlorine atom
  • R 3 and R 8 are each independently a hydrogen atom, NO 2 , OCH 3 , OC 2 H 5 , bromine atom, chlorine atom, CH 3 , C 2 H 5 , N (CH 3 ) 2 , N (CH 3 ) (C 2 H 5 ), N (C 2 H 5 ) 2 , ⁇ -naphthyl, ⁇ -naphthyl, SO 3 H or SO 3 —
  • R 1 is the same as R 6
  • R 2 is the same as R 7
  • R 3 is the same as R 8
  • the photosensitive coloring composition according to [1] wherein R 4 is the same as R 9 and R 5 is the same as R 10 .
  • the content ratio of the (A-1) organic black pigment is 30 to 90 mass% and the content ratio of the (A-2) organic color pigment is 10 to 70 mass% with respect to 100 mass% of the color material (A).
  • the photosensitive coloring composition according to any one of [1] to [7], wherein the (A) coloring material further contains (A-3) carbon black.
  • the content ratio of the (A-1) organic black pigment is 50 to 90 mass% and the content ratio of (A-3) carbon black is 10 to 50 mass% with respect to 100 mass% of the color material (A).
  • the photosensitive coloring composition as described in [8].
  • An image display device comprising the black matrix according to [12] or the colored spacer according to [13].
  • R 1 and R 6 are each independently a hydrogen atom, CH 3 , CF 3 , a fluorine atom or a chlorine atom;
  • R 2 , R 4 , R 5 , R 7 , R 9 and R 10 are each independently a hydrogen atom, a fluorine atom or a chlorine atom
  • R 3 and R 8 are independently a hydrogen atom, NO 2, OCH 3, OC 2 H 5, a bromine atom, a chlorine atom, CH 3, C 2 H 5 , N (CH 3) 2, N (CH 3) (C 2 H 5), N (C 2 H 5 ) 2 , ⁇ -naphthyl, ⁇ -naphthyl, SO 3 H or SO 3 —
  • R 1 is the same as R 6
  • R 2 is the same as R 7
  • R 3 is the same as R 8
  • R 4 is the same as R 9 and R 5 is the same as R 10 .
  • the photosensitive coloring composition of the present invention includes an organic black pigment having a specific structure, so that the amount of the dispersing agent can be reduced at the time of preparing the pigment dispersion, thereby exhibiting excellent plate making characteristics and dispersibility. Also excellent. Therefore, the black matrix formed from the photosensitive coloring composition of the present invention exhibits excellent light shielding properties. Further, the black matrix and the colored spacer of the present invention exhibit a sufficiently low relative dielectric constant so as not to cause a short circuit or malfunction even when formed on the TFT element substrate.
  • the image display device having the black matrix of the present invention is free from problems such as TFT failure and liquid crystal drive disturbance, and is excellent in reliability.
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic EL element.
  • (meth) acryl means “acryl and / or methacryl”, and the same applies to “(meth) acrylate” and “(meth) acryloyl”.
  • (co) polymer means to include both a single polymer (homopolymer) and a copolymer (copolymer).
  • acid (anhydride) means to include both acids and anhydrides.
  • acrylic resin means a (co) polymer containing (meth) acrylic acid and a (co) polymer containing a (meth) acrylic ester having a carboxyl group.
  • the term “monomer” is a term corresponding to a so-called high molecular substance (polymer), and includes a dimer, a trimer, an oligomer, etc. in addition to a monomer (monomer) in a narrow sense. It is.
  • the “total solid content” means all components other than the solvent contained in the photosensitive coloring composition or the ink described later.
  • the weight average molecular weight refers to a polystyrene equivalent weight average molecular weight (Mw) by GPC (gel permeation chromatography).
  • the “amine value” means an amine value in terms of effective solid content unless otherwise specified, and is a value represented by the mass of KOH equivalent to the base amount per 1 g of the solid content of the dispersant. It is. The measuring method will be described later.
  • the “acid value” represents an acid value in terms of effective solid content unless otherwise specified, and is calculated by neutralization titration.
  • photosensitive coloring composition The photosensitive coloring composition of the present invention (hereinafter sometimes referred to as “photosensitive coloring composition” or “colored resin composition”)
  • Photopolymerization initiator is contained as an essential component, and if necessary, adhesion improvers such as organic solvents and silane coupling agents, coating It contains other compounding components such as property improvers, development improvers, ultraviolet absorbers, antioxidants, surfactants, pigment derivatives, etc., and each compounding component is usually dissolved or dispersed in an organic solvent. used.
  • the coloring material (A) used in the present invention includes (A-1) a compound represented by the following general formula (1), a geometric isomer thereof, a salt thereof, or an organic black pigment that is a salt of the geometric isomer. .
  • R 1 and R 6 are each independently a hydrogen atom, CH 3 , CF 3 , a fluorine atom or a chlorine atom;
  • the compound represented by general formula (1) When the compound represented by general formula (1) is anionic, its charge can be any known suitable cation, such as a metal, organic, inorganic or metal organic cation, specifically an alkali metal, alkaline earth metal.
  • the geometric isomer of the compound represented by the general formula (1) is anionic, it is preferably a similar salt.
  • R 2 , R 4 , R 5 , R 7 , R 9 and R 10 are independently of each other preferably a hydrogen atom, a fluorine atom or a chlorine atom, more preferably a hydrogen atom.
  • R 3 and R 8 are preferably independently of each other a hydrogen atom, NO 2 , OCH 3 , OC 2 H 5 , bromine atom, chlorine atom, CH 3 , C 2 H 5 , N (CH 3 ) 2 , N (CH 3 ) (C 2 H 5 ), N (C 2 H 5 ) 2 , ⁇ -naphthyl, ⁇ -naphthyl, SO 3 H or SO 3 — , more preferably a hydrogen atom or SO 3 H.
  • R 1 and R 6 are preferably each independently a hydrogen atom, CH 3 or CF 3 , more preferably a hydrogen atom.
  • at least one combination selected from the group consisting of R 1 and R 6 , R 2 and R 7 , R 3 and R 8 , R 4 and R 9 , and R 5 and R 10 is the same, and more preferably R 1 is the same as R 6 , R 2 is the same as R 7 , R 3 is the same as R 8 , R 4 is the same as R 9 , and R 5 is the same as R 10 Are the same.
  • alkyl group having 1 to 12 carbon atoms examples include methyl group, ethyl group, n-propyl group, isopropyl group, n-butyl group, sec-butyl group, isobutyl group, tert-butyl group, 2-methylbutyl group, n- Pentyl group, 2-pentyl group, 3-pentyl group, 2,2-dimethylpropyl group, n-hexyl group, heptyl group, n-octyl group, 1,1,3,3-tetramethylbutyl group, 2-ethylhexyl Group, nonyl group, decyl group, undecyl group or dodecyl group.
  • Examples of the cycloalkyl group having 3 to 12 carbon atoms include cyclopropyl group, cyclopropylmethyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cyclohexylmethyl group, trimethylcyclohexyl group, tuzyl group, norbornyl group, bornyl group, norcaryl group. , Caryl group, menthyl group, norpinyl group, pinyl group, 1-adamantyl group or 2-adamantyl group.
  • alkenyl group having 2 to 12 carbon atoms examples include vinyl group, allyl group, 2-propen-2-yl group, 2-buten-1-yl group, 3-buten-1-yl group, and 1,3-butadiene.
  • Examples of the cycloalkenyl group having 3 to 12 carbon atoms include a 2-cyclobuten-1-yl group, a 2-cyclopenten-1-yl group, a 2-cyclohexen-1-yl group, a 3-cyclohexen-1-yl group, , 4-Cyclohexadien-1-yl group, 1-p-menten-8-yl group, 4 (10) -tgen-10-yl group, 2-norbornen-1-yl group, 2,5-norbornadiene-1 -Yl group, 7,7-dimethyl-2,4-norcaradien-3-yl group or camphenyl group.
  • alkynyl group having 2 to 12 carbon atoms examples include 1-propyn-3-yl group, 1-butyn-4-yl group, 1-pentyn-5-yl group, and 2-methyl-3-butyn-2-yl.
  • the halogen atom is, for example, a fluorine atom, a chlorine atom, a bromine atom or an iodine atom.
  • a preferable organic black pigment (A-1) is a compound represented by the following general formula (2).
  • organic black pigments include Irgaphor (registered trademark) Black S 0100 CF (manufactured by BASF) under the trade name.
  • the organic black pigment (A-1) is preferably used after being dispersed by a dispersant, a solvent and a method described later.
  • dispersibility and storage stability may be improved.
  • the photosensitive coloring composition of the present invention may contain a color material other than (A-1) as the color material (A).
  • a color material other than (A-1) as the color material (A).
  • dyes and pigments can be used, but pigments are preferable from the viewpoint of heat resistance, light resistance and the like.
  • (A-2) organic color pigments and / or (A-3) carbon black are preferably used.
  • an organic coloring pigment is a powder containing an organic compound used for coloring as a component, and means a thing unnecessary for water or oil.
  • A-2) Various colors such as blue pigments, green pigments, red pigments, yellow pigments, purple pigments, orange pigments, brown pigments, black pigments other than (A-1) and (A-3) as organic coloring pigments
  • Organic pigments can be used.
  • organic pigments such as azo, phthalocyanine, quinacridone, benzimidazolone, isoindolinone, dioxazine, and indanthrene
  • various inorganic pigments can be used.
  • the color of the pigment means a color exhibited when a photosensitive coloring composition is formed by using the pigment alone as a coloring material, unless otherwise specified. That is, for example, a black pigment means a pigment that exhibits a black color when a photosensitive coloring composition is formed using the pigment alone as a colorant.
  • pigments that can be used in the present invention are shown by pigment numbers below.
  • terms such as “CI Pigment Red 2” mentioned below mean a color index (CI).
  • red pigments include C.I. I. Pigment Red 1, 2, 3, 4, 5, 6, 7, 8, 9, 12, 14, 15, 16, 17, 21, 22, 23, 31, 32, 37, 38, 41, 47, 48, 48: 1, 48: 2, 48: 3, 48: 4, 49, 49: 1, 49: 2, 50: 1, 52: 1, 52: 2, 53, 53: 1, 53: 2, 53: 3, 57, 57: 1, 57: 2, 58: 4, 60, 63, 63: 1, 63: 2, 64, 64: 1, 68, 69, 81, 81: 1, 81: 2, 81: 3, 81: 4, 83, 88, 90: 1, 101, 101: 1, 104, 108, 108: 1, 109, 112, 113, 114, 122, 123, 144, 146, 147, 149, 151, 166, 168, 169, 170, 172
  • C.I. I. Pigment Red 48 1, 122, 168, 177, 202, 206, 207, 209, 224, 242, 254, more preferably C.I. I. Pigment red 177, 209, 224, 254.
  • C.I. I. Pigment Red 177, 254, and 272 are preferably used.
  • a red pigment having a low ultraviolet absorptivity Is C.I. I. It is more preferable to use CI Pigment Red 254,272.
  • C.I. I. Pigment Blue 1 As blue pigment, C.I. I. Pigment Blue 1, 1: 2, 9, 14, 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, 16, 17, 19, 25, 27, 28, 29, 33, 35, 36, 56, 56: 1, 60, 61, 61: 1, 62, 63, 66, 67, 68, 71, 72, 73, 74, 75, 76, 78, 79. Of these, C.I. I. Pigment Blue 15, 15: 1, 15: 2, 15: 3, 15: 4, 15: 6, more preferably C.I. I. Pigment blue 15: 6. In terms of dispersibility and light shielding properties, C.I. I. Pigment Blue 15: 6, 16, and 60 are preferably used. When the photosensitive coloring composition of the present invention is cured with ultraviolet rays, it is preferable to use a blue pigment having a low ultraviolet absorption rate. From the viewpoint, C.I. I. More preferably, CI Pigment Blue 60 is used.
  • green pigments examples include C.I. I. Pigment green 1, 2, 4, 7, 8, 10, 13, 14, 15, 17, 18, 19, 26, 36, 45, 48, 50, 51, 54, 55. Of these, C.I. I. And CI Pigment Green 7 and 36.
  • yellow pigments examples include C.I. I.
  • C.I. I. Pigment yellow 83, 117, 129, 138, 139, 150, 154, 155, 180, 185 more preferably C.I. I. Pigment yellow 83, 138, 139, 150, 180.
  • Orange (orange) pigments include C.I. I. Pigment Orange 1, 2, 5, 13, 16, 17, 19, 20, 21, 22, 23, 24, 34, 36, 38, 39, 43, 46, 48, 49, 61, 62, 64, 65, 67, 68, 69, 70, 71, 72, 73, 74, 75, 77, 78, 79. Of these, C.I. I. And CI pigment oranges 38 and 71. In terms of dispersibility and light shielding properties, C.I. I. Pigment Orange 43, 64, and 72 are preferably used. When the photosensitive coloring composition of the present invention is cured with ultraviolet rays, it is preferable to use an orange pigment having a low ultraviolet absorption rate. Is C.I. I. More preferably, CI pigment oranges 64 and 72 are used.
  • C.I. I. Pigment Violet 1 As purple pigment, C.I. I. Pigment Violet 1, 1: 1, 2, 2: 2, 3, 3: 1, 3: 3, 5, 5: 1, 14, 15, 16, 19, 23, 25, 27, 29, 31, 32, 37, 39, 42, 44, 47, 49, 50.
  • C.I. I. Pigment Violet 23 and 29 are preferably used, and when the photosensitive coloring composition of the present invention is cured with ultraviolet rays, it is preferable to use a violet pigment having a low ultraviolet absorption rate. . I. More preferably, pigment violet 29 is used.
  • Color index pigment blue 60 or 15 6 Red: Color index pigment red 177, 254, or 272
  • Purple Color index pigment violet 23 or 29
  • Orange Color index pigment orange 43, 64 or 72
  • the color combination is not particularly limited, but from the viewpoint of light shielding properties, for example, a combination of a red pigment and a blue pigment, or a combination of a blue pigment, an orange pigment and a purple pigment Etc.
  • a dye may be used in place of (A-2) the organic color pigment, and a dye may be used in addition to (A-2) the organic color pigment.
  • the dye that can be used as the color material include azo dyes, anthraquinone dyes, phthalocyanine dyes, quinoneimine dyes, quinoline dyes, nitro dyes, carbonyl dyes, and methine dyes.
  • the azo dye include C.I. I. Acid Yellow 11, C.I. I. Acid Orange 7, C.I. I. Acid Red 37, C.I. I. Acid Red 180, C.I. I. Acid Blue 29, C.I. I. Direct Red 28, C.I. I. Direct Red 83, C.I. I.
  • Direct Yellow 12 C.I. I. Direct Orange 26, C.I. I. Direct Green 28, C.I. I. Direct Green 59, C.I. I. Reactive Yellow 2, C.I. I. Reactive Red 17, C.I. I. Reactive Red 120, C.I. I. Reactive Black 5, C.I. I. Disperse Orange 5, C.I. I. Disperse thread 58, C.I. I. Disperse blue 165, C.I. I. Basic Blue 41, C.I. I. Basic Red 18, C.I. I. Molded Red 7, C.I. I. Moldant Yellow 5, C.I. I. Examples thereof include Moldant Black 7.
  • anthraquinone dyes examples include C.I. I. Bat Blue 4, C.I. I. Acid Blue 40, C.I. I. Acid Green 25, C.I. I. Reactive Blue 19, C.I. I. Reactive Blue 49, C.I. I. Disperse thread 60, C.I. I. Disperse Blue 56, C.I. I. Disperse Blue 60 etc. are mentioned.
  • Other examples of the phthalocyanine dye include C.I. I. Pad Blue 5 and the like are quinone imine dyes such as C.I. I. Basic Blue 3, C.I. I. Basic Blue 9 and the like are quinoline dyes such as C.I. I. Solvent Yellow 33, C.I. I. Acid Yellow 3, C.I. I. Disperse Yellow 64 and the like are nitro dyes such as C.I. I. Acid Yellow 1, C.I. I. Acid Orange 3, C.I. I. Disperse Yellow 42 and the like.
  • a black pigment other than (A-1) can also be used in the photosensitive coloring composition of the present invention.
  • Black pigments other than (A-1) may be used singly or as a mixture of red, green, blue and the like.
  • These color materials can be appropriately selected from inorganic or organic pigments and dyes.
  • Color materials that can be mixed for preparing a black color material include Victoria Pure Blue (42595), Auramin O (41000), Catillon Brilliant Flavin (Basic 13), Rhodamine 6GCP (45160), Rhodamine B (45170). Safranin OK 70: 100 (50240), Erioglaucine X (42080), No.
  • C.I. I Yellow pigments 20, 24, 86, 93, 109, 110, 117, 125, 137, 138, 147, 148, 153, 154, 166, C.I. I. Orange pigments 36, 43, 51, 55, 59, 61, C.I. I. Red pigments 9, 97, 122, 123, 149, 168, 177, 180, 192, 215, 216, 217, 220, 223, 224, 226, 227, 228, 240, C.I. I. Violet pigments 19, 23, 29, 30, 37, 40, 50, C.I. I. Blue pigment 15, 15: 1, 15: 4, 22, 60, 64, C.I. I. Green pigment 7, C.I. I. Examples thereof include brown pigments 23, 25, and 26.
  • black color material examples include acetylene black, lamp black, bone black, graphite, iron black, aniline black, cyanine black, titanium black, and perylene black.
  • (A-3) carbon black is preferably used as a color material other than the (A-1) organic black pigment from the viewpoints of light shielding rate and image characteristics.
  • Examples of carbon black include the following carbon black.
  • the total content of Na and Ca is preferably 100 ppm or less.
  • Carbon black is usually raw material oil or combustion oil (or gas) at the time of production, reaction stop water or granulated water, Na mixed from furnace materials of the reactor, Ca, K, Mg, Al, Fe.
  • the ash content of etc. is contained on the order of percent.
  • Na and Ca are generally contained in a few hundred ppm or more, but if many of these are present, they penetrate into the transparent electrode (ITO) and other electrodes, causing electrical shorts. This is because there is a case.
  • the resin-coated carbon black is preferably so-called acidic carbon black having a pH of 6 or less. Since the dispersion diameter (agglomerate diameter) in water is small, it is possible to cover fine units. Furthermore, it is preferable that the particle diameter is 40 nm or less and the dibutyl phthalate (DBP) absorption is 140 ml / 100 g or less. If the particle diameter is larger than 40 nm and the DBP absorption is larger than 140 ml / 100 g, the dispersibility when made into a paste is excellent, but the coating film may not have sufficient density, and if the film thickness is about 1 to 2 ⁇ m, the light is blocked. It is because there is a possibility that it may become scarce.
  • DBP dibutyl phthalate
  • the method for preparing the carbon black coated with the resin is not particularly limited. For example, after appropriately adjusting the blending amount of the carbon black and the resin, After mixing and stirring the resin solution obtained by mixing the resin and a solvent such as cyclohexanone, toluene, xylene, and the like, and the suspension obtained by mixing carbon black and water, the carbon black and water are separated, 1. A method in which water is removed and the composition obtained by heating and kneading is formed into a sheet, pulverized and then dried; A method of mixing and stirring the resin solution and suspension prepared in the same manner as above to granulate carbon black and the resin, separating the obtained granular material, and heating to remove the remaining solvent and water; 3.
  • a solvent such as cyclohexanone, toluene, xylene, and the like
  • Dissolve carboxylic acid such as maleic acid and fumaric acid in the above-mentioned solvent add carbon black, mix and dry, remove the solvent to obtain carboxylic acid-impregnated carbon black, and then add resin to it.
  • a method of adding black and kneading, reacting carbon black with a reactive group (grafting carbon black), cooling and pulverizing, and the like can be employed.
  • the type of resin to be coated is not particularly limited, but synthetic resins are common, and resins with benzene nuclei in the structure have a stronger function as amphoteric surfactants. From the viewpoint of dispersibility and dispersion stability, it is preferable.
  • Specific synthetic resins include phenolic resin, melamine resin, xylene resin, diallyl phthalate resin, glyphtal resin, epoxy resin, alkylbenzene resin and other thermosetting resins, polystyrene, polycarbonate, polyethylene terephthalate, polybutylene terephthalate, and modified polyphenylene.
  • Thermoplastic resins such as oxide, polysulfone, polyparaphenylene terephthalamide, polyamide imide, polyimide, polyamino bismaleimide, polyether sulfopolyphenylene sulfone, polyarylate, polyether ether ketone, can be used.
  • the coating amount of the resin on the carbon black is preferably 1 to 30% by mass with respect to the total amount of the carbon black and the resin, and when the amount is less than 1% by mass, only dispersibility and dispersion stability similar to those of the untreated carbon black can be obtained. There is a risk of not being able to. On the other hand, when it exceeds 30% by mass, the adhesiveness between the resins is strong, and it becomes a dumpling-like mass, and the dispersion may not proceed.
  • the carbon black thus coated with the resin can be used as a black matrix shading material according to a conventional method, and a color filter having this black matrix as a constituent element can be prepared by a conventional method.
  • a black matrix having a high light shielding rate, a low surface reflectance, and a small film thickness can be achieved at a low cost. It is presumed that the dispersibility and dispersion stability of carbon black were significantly improved with respect to the resin and solvent constituting the black matrix liquid. It is also presumed that by coating the carbon black surface with a resin, Ca and Na can be contained in the carbon black.
  • pigments particularly preferably used in terms of light shielding properties include C.I. I. Pigment blue 60, C.I. I. Pigment blue 15: 6, C.I. I. Pigment red 177, C.I. I. Pigment red 242, C.I. I. Pigment blue 254, C.I.
  • an organic coloring pigment when included, it preferably contains at least one of the above pigments, and more preferably contains two or more.
  • (A-3) carbon black resin-coated carbon black is preferably used in terms of volume resistance and dielectric constant.
  • These pigments are preferably used dispersed in such a manner that the average particle size is usually 1 ⁇ m or less, preferably 0.5 ⁇ m or less, more preferably 0.25 ⁇ m or less.
  • the standard of the average particle diameter is the number of pigment particles.
  • the average particle diameter of the pigment is a value obtained from the pigment particle diameter measured by dynamic light scattering (DLS).
  • DLS dynamic light scattering
  • a fully diluted colored resin composition usually diluted to prepare a pigment concentration of about 0.005 to 0.2% by mass. However, if there is a concentration recommended by the measuring instrument, its concentration And measure at 25 ° C.
  • (A) it is important to finely disperse the coloring material and stabilize the dispersion state, so that it is important to ensure the stability of the quality.
  • (A-1) from the viewpoint of dispersibility of the organic black pigment, a polymer dispersant having a quaternary ammonium base as a functional group is included.
  • the polymer dispersant further includes a carboxyl group; a phosphoric acid group; a sulfonic acid group; or a base thereof; a primary, secondary, or tertiary amino group; a nitrogen-containing heterogeneous group such as pyridine, pyrimidine, and pyrazine. It may further have a functional group such as a ring-derived group.
  • a polymer dispersant further having a basic functional group such as a primary, secondary or tertiary amino group; a group derived from a nitrogen-containing heterocycle such as pyridine, pyrimidine, pyrazine, etc.
  • (A-1) from the viewpoint of dispersibility of the organic black pigment
  • (A-2) from the viewpoint of dispersibility of the organic color pigment and / or (A-3) carbon black, a quaternary ammonium base.
  • a polymer dispersant having a tertiary amino group as a functional group is preferred.
  • polymer dispersants include urethane dispersants, acrylic dispersants, polyethyleneimine dispersants, polyallylamine dispersants, dispersants composed of amino group-containing monomers and macromonomers, and polyoxyethylene alkyl ethers.
  • examples thereof include a system dispersant, a polyoxyethylene diester dispersant, a polyether phosphate dispersant, a polyester phosphate dispersant, a sorbitan aliphatic ester dispersant, and an aliphatic modified polyester dispersant.
  • a dispersant examples include trade names of EFKA (registered trademark, manufactured by BASF), DISPERBYK (registered trademark, manufactured by BYK Chemie), Disparon (registered trademark, manufactured by Enomoto Kasei), and SOLPERSE. (Registered trademark, manufactured by Lubrizol Corp.), KP (manufactured by Shin-Etsu Chemical Co., Ltd.), polyflow (manufactured by Kyoeisha Chemical Co., Ltd.), Ajisper (registered trademark, manufactured by Ajinomoto Co., Inc.) and the like. These polymer dispersants may be used alone or in combination of two or more.
  • the weight average molecular weight (Mw) of the polymer dispersant is usually 700 or more, preferably 1000 or more, and usually 100,000 or less, preferably 50,000 or less.
  • the dispersant preferably contains a urethane polymer dispersant and / or an acrylic polymer dispersant having a functional group, and an acrylic polymer dispersant. It is particularly preferable that From the viewpoint of dispersibility and storage stability, a polymer dispersant having a basic functional group and having a polyester bond and / or a polyether bond is preferable.
  • urethane and acrylic polymer dispersants examples include DISPERBYK 160 to 166, 182 series (both are urethane), DISPERBYK2000, 2001, LPN21116, etc. (both are acrylic) (all manufactured by Big Chemie).
  • Specific examples of a preferable chemical structure as a urethane-based polymer dispersant include, for example, the same as a polyisocyanate compound and a compound having one or two hydroxyl groups in the molecule and a number average molecular weight of 300 to 10,000.
  • examples thereof include a dispersion resin having a weight average molecular weight of 1,000 to 200,000 obtained by reacting a compound having an active hydrogen and a tertiary amino group in the molecule. By treating these with a quaternizing agent such as benzyl chloride, all or part of the tertiary amino group can be converted to a quaternary ammonium base.
  • polyisocyanate compounds examples include paraphenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, naphthalene-1,5-diisocyanate, and tolidine diisocyanate.
  • Aromatic diisocyanates hexamethylene diisocyanates, lysine methyl ester diisocyanates, 2,4,4-trimethylhexamethylene diisocyanates, dimer acid diisocyanates and other aliphatic diisocyanates, isophorone diisocyanates, 4,4'-methylenebis (cyclohexyl isocyanate), ⁇ , ⁇ Alicyclic diisocyanates such as '-diisocyanate dimethylcyclohexane, xylylene diisocyanate, ⁇ , ⁇ , ⁇ ', ⁇ '-tetra Aliphatic diisocyanates having an aromatic ring such as tilxylylene diisocyanate, lysine ester triisocyanate, 1,6,11-undecane triisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, 1,3,6-hexamethylene triisocyanate Examples thereof include triiso
  • polyisocyanate are trimers of organic diisocyanate, and most preferred are trimerene of tolylene diisocyanate and trimer of isophorone diisocyanate. These may be used alone or in combination of two or more.
  • the polyisocyanate may be converted into an isocyanate group using an appropriate trimerization catalyst such as tertiary amines, phosphines, alkoxides, metal oxides, carboxylates and the like. And the trimerization is stopped by adding a catalyst poison, and then the unreacted polyisocyanate is removed by solvent extraction and thin-film distillation to obtain the desired isocyanurate group-containing polyisocyanate.
  • an appropriate trimerization catalyst such as tertiary amines, phosphines, alkoxides, metal oxides, carboxylates and the like.
  • Examples of the compound having one or two hydroxyl groups in the same molecule and having a number average molecular weight of 300 to 10,000 include polyether glycol, polyester glycol, polycarbonate glycol, polyolefin glycol and the like, and one terminal hydroxyl group of these compounds has a carbon number. Examples thereof include those alkoxylated with 1 to 25 alkyl groups and mixtures of two or more thereof.
  • Polyether glycols include polyether diols, polyether ester diols, and mixtures of two or more of these.
  • polyether diols are those obtained by homopolymerizing or copolymerizing alkylene oxides such as polyethylene glycol, polypropylene glycol, polyethylene-propylene glycol, polyoxytetramethylene glycol, polyoxyhexamethylene glycol, polyoxyoctamethylene glycol, and the like. A mixture of two or more of the above.
  • Polyether ester diols include those obtained by reacting a mixture of ether group-containing diols or other glycols with dicarboxylic acids or their anhydrides or reacting polyester glycols with alkylene oxides, such as poly (poly And oxytetramethylene) adipate.
  • alkylene oxides such as poly (poly And oxytetramethylene) adipate.
  • the polyether glycol is polyethylene glycol, polypropylene glycol, polyoxytetramethylene glycol or a compound in which one terminal hydroxyl group of these compounds is alkoxylated with an alkyl group having 1 to 25 carbon atoms.
  • Polyester glycol includes dicarboxylic acid (succinic acid, glutaric acid, adipic acid, sebacic acid, fumaric acid, maleic acid, phthalic acid, etc.) or anhydrides thereof and glycol (ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, Dipropylene glycol, tripropylene glycol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, 3-methyl-1,5-pentanediol, neopentyl glycol 2-methyl-1,3-propanediol, 2-methyl-2-propyl-1,3-propanediol, 2-butyl-2-ethyl-1,3-propanediol, 1,5-pentanediol, , 6-hexanediol, 2-methyl-2,4 Pentanediol, 2,2,
  • Polycarbonate glycols include poly (1,6-hexylene) carbonate, poly (3-methyl-1,5-pentylene) carbonate, and polyolefin glycols include polybutadiene glycol, hydrogenated polybutadiene glycol, hydrogenated polyisoprene glycol, etc. Is mentioned. These may be used alone or in combination of two or more.
  • the number average molecular weight of the compound having one or two hydroxyl groups in the same molecule is usually 300 to 10,000, preferably 500 to 6,000, and more preferably 1,000 to 4,000.
  • Active hydrogen that is, a hydrogen atom directly bonded to an oxygen atom, a nitrogen atom or a sulfur atom includes a hydrogen atom in a functional group such as a hydroxyl group, an amino group, and a thiol group. Of these, the hydrogen atom of the amino group is preferred.
  • the tertiary amino group is not particularly limited, and examples thereof include an amino group having an alkyl group having 1 to 4 carbon atoms, or a heterocyclic structure, more specifically, an imidazole ring or a triazole ring.
  • Examples of such compounds having an active hydrogen and a tertiary amino group in the same molecule include N, N-dimethyl-1,3-propanediamine, N, N-diethyl-1,3-propanediamine, N , N-dipropyl-1,3-propanediamine, N, N-dibutyl-1,3-propanediamine, N, N-dimethylethylenediamine, N, N-diethylethylenediamine, N, N-dipropylethylenediamine, N, N -Dibutylethylenediamine, N, N-dimethyl-1,4-butanediamine, N, N-diethyl-1,4-butanediamine, N, N-dipropyl
  • examples of the nitrogen-containing heterocyclic ring include pyrazole ring, imidazole ring, triazole ring, tetrazole ring, indole ring, carbazole ring, indazole ring, benzimidazole ring, benzo Nitrogen-containing hetero 6-membered rings such as triazole ring, benzoxazole ring, benzothiazole ring, benzothiadiazole ring, etc., pyridine ring, pyridazine ring, pyrimidine ring, triazine ring, quinoline ring, acridine ring, isoquinoline ring A ring is mentioned.
  • nitrogen-containing heterocycles preferred are an imidazole ring or a triazole ring.
  • these compounds having an imidazole ring and an amino group include 1- (3-aminopropyl) imidazole, histidine, 2-aminoimidazole, 1- (2-aminoethyl) imidazole and the like.
  • specific examples of the compound having a triazole ring and an amino group include 3-amino-1,2,4-triazole, 5- (2-amino-5-chlorophenyl) -3-phenyl-1H-1 2,4-triazole, 4-amino-4H-1,2,4-triazole-3,5-diol, 3-amino-5-phenyl-1H-1,3,4-triazole, 5-amino-1 , 4-diphenyl-1,2,3-triazole, 3-amino-1-benzyl-1H-2,4-triazole and the like.
  • N, N-dimethyl-1,3-propanediamine, N, N-diethyl-1,3-propanediamine, 1- (3-aminopropyl) imidazole, and 3-amino-1,2,4-triazole preferable. These may be used alone or in combination of two or more.
  • the preferred blending ratio of the raw materials for producing the urethane polymer dispersant is 10 compounds having a number average molecular weight of 300 to 10,000 having one or two hydroxyl groups in the same molecule with respect to 100 parts by mass of the polyisocyanate compound.
  • the production of the urethane-based polymer dispersant is performed according to a known method for producing a polyurethane resin.
  • a solvent for production usually, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, isophorone, esters such as ethyl acetate, butyl acetate, cellosolve acetate, benzene, toluene, xylene, hexane Hydrocarbons such as diacetone alcohol, isopropanol, sec-butanol, tert-butanol, etc., chlorides such as methylene chloride and chloroform, ethers such as tetrahydrofuran and diethyl ether, dimethylformamide, N-methyl Aprotic polar solvents such as pyrrolidone and dimethyl sulfoxide are used. These may be used alone or in combination of
  • a urethanization reaction catalyst is usually used.
  • the catalyst include tin-based compounds such as dibutyltin dilaurate, dioctyltin dilaurate, dibutyltin dioctate, and stannous octoate, iron-based compounds such as iron acetylacetonate and ferric chloride, triethylamine, and triethylenediamine. Secondary amine type and the like can be mentioned. These may be used alone or in combination of two or more.
  • the introduction amount of the compound having active hydrogen and tertiary amino group in the same molecule is preferably controlled in the range of 1 to 100 mgKOH / g in terms of the amine value after the reaction. More preferably, it is in the range of 5 to 95 mgKOH / g.
  • the amine value is a value obtained by neutralizing and titrating a basic amino group with an acid, and representing the acid value in mg of KOH. When the amine value is lower than the above range, the dispersing ability tends to be lowered, and when it exceeds the above range, the developability tends to be lowered.
  • the weight average molecular weight (Mw) of the urethane-based polymer dispersant is usually in the range of 1,000 to 200,000, preferably 2,000 to 100,000, more preferably 3,000 to 50,000. If the molecular weight is less than 1,000, the dispersibility and dispersion stability are poor, and if it exceeds 200,000, the solubility is lowered and the dispersibility is poor, and at the same time, it becomes difficult to control the reaction.
  • an unsaturated group-containing monomer having a functional group (the functional group here is the functional group described above as the functional group contained in the polymer dispersant); It is preferable to use a random copolymer, a graft copolymer, or a block copolymer with an unsaturated group-containing monomer having no functional group. These copolymers can be produced by a known method.
  • Examples of the unsaturated group-containing monomer having a functional group include (meth) acrylic acid, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethylphthalic acid, 2- (meth) acrylic acid.
  • Tertiary amino groups such as unsaturated monomers having a carboxyl group such as leuoxyethyl hexahydrophthalic acid and acrylic acid dimer, dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate and quaternized products thereof; Specific examples include unsaturated monomers having a quaternary ammonium base. These may be used alone or in combination of two or more.
  • Examples of the unsaturated group-containing monomer having no functional group include methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl ( (Meth) acrylate, t-butyl (meth) acrylate, benzyl (meth) acrylate, phenyl (meth) acrylate, cyclohexyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxymethyl (meth) acrylate, 2-ethylhexyl (meth) Acrylate, isobornyl (meth) acrylate, tricyclodecane (meth) acrylate, tetrahydrofurfuryl (meth) acrylate, N-vinylpyrrolidone, styrene and its derivatives
  • the acrylic polymer dispersant is particularly preferably an AB or BAB block copolymer composed of an A block having a functional group and a B block having no functional group.
  • the block may contain a partial structure derived from the unsaturated group-containing monomer not containing the functional group. May be contained in the A block in any form of random copolymerization or block copolymerization.
  • content in the A block of the partial structure which does not contain a functional group is 80 mass% or less normally, Preferably it is 50 mass% or less, More preferably, it is 30 mass% or less.
  • the B block is composed of a partial structure derived from an unsaturated group-containing monomer that does not contain the above functional group, but a partial structure derived from two or more types of monomers is contained in one B block. These may be contained in the B block in any form of random copolymerization or block copolymerization.
  • the AB or BAB block copolymer is prepared, for example, by the living polymerization method shown below.
  • the living polymerization method includes an anion living polymerization method, a cation living polymerization method, and a radical living polymerization method. Among these, the anion living polymerization method has a polymerization active species as an anion, and is represented by the following scheme, for example.
  • Ar 1 is a monovalent organic group
  • Ar 2 is a monovalent organic group different from Ar 1
  • M is a metal atom
  • s and t are each an integer of 1 or more.
  • the polymerization active species is a radical, and is represented by the following scheme, for example.
  • Ar 1 is a monovalent organic group
  • Ar 2 is a monovalent organic group different from Ar 1
  • j and k are each an integer of 1 or more
  • R a is a hydrogen atom or 1
  • R b is a hydrogen atom different from R a or a monovalent organic group.
  • the acrylic polymer dispersant that can be used in the present invention may be an AB block copolymer or a BAB block copolymer, and the A block constituting the copolymer.
  • / B block ratio is preferably 1/99 to 80/20, particularly 5/95 to 60/40 (mass ratio). Outside this range, good heat resistance and dispersibility cannot be achieved. There is.
  • the amount of the quaternary ammonium base in 1 g of the AB block copolymer and BAB block copolymer that can be used in the present invention is preferably 0.1 to 10 mmol. Outside the range, it may not be possible to combine good heat resistance and dispersibility.
  • Such a block copolymer usually contains an amino group generated in the production process, but its amine value is about 1 to 100 mgKOH / g, and from the viewpoint of dispersibility, Preferably it is 10 mgKOH / g or more, More preferably, it is 30 mgKOH / g or more, More preferably, it is 50 mgKOH / g or more, Preferably it is 90 mgKOH / g or less, More preferably, it is 80 mgKOH / g or less, More preferably, it is 75 mgKOH / g or less.
  • the amine value of the dispersant such as these block copolymers is expressed by the mass of KOH equivalent to the amount of base per gram of solid content excluding the solvent in the dispersant sample, and is measured by the following method. Disperse 0.5-1.5 g of the dispersant sample in a 100 mL beaker and dissolve with 50 mL of acetic acid. This solution is neutralized with a 0.1 mol / L HClO 4 acetic acid solution using an automatic titrator equipped with a pH electrode. Using the inflection point of the titration pH curve as the end point of titration, the amine value is determined by the following formula.
  • the acid value of the block copolymer depends on the presence and type of the acid group that is the basis of the acid value, but is generally preferably low, and is usually 10 mg KOH / g or less, and its weight average molecular weight (Mw) ) Is preferably in the range of 1000 to 100,000. When the weight average molecular weight of the block copolymer is less than 1000, the dispersion stability tends to decrease, and when it exceeds 100,000, the developability and resolution tend to decrease.
  • the specific structure of the polymer dispersant having a quaternary ammonium base as a functional group is not particularly limited, but from the viewpoint of dispersibility, a repeating unit represented by the following formula (i) (hereinafter referred to as “repeating unit ( i) ").
  • R 31 to R 33 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • R 34 is a hydrogen atom or a methyl group.
  • X is a divalent linking group
  • Y ⁇ is a counter anion.
  • the number of carbon atoms of the alkyl group which may have a substituent in R 31 to R 33 in the above formula (i) is not particularly limited, but is usually 1 or more and preferably 10 or less. The following is more preferable.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Among these, a methyl group, an ethyl group, a propyl group, and a butyl group are exemplified.
  • It is preferably a group, a pentyl group or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group or a butyl group. Further, it may be linear or branched. Further, it may contain a cyclic structure such as a cyclohexyl group or a cyclohexylmethyl group.
  • the number of carbon atoms of the aryl group which may have a substituent in R 31 to R 33 in the above formula (i) is not particularly limited, but is usually 6 or more and preferably 16 or less. The following is more preferable.
  • Specific examples of the aryl group include a phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, a diethylphenyl group, a naphthyl group, and an anthracenyl group.
  • a phenyl group, a methylphenyl group, and an ethylphenyl group A dimethylphenyl group, or a diethylphenyl group, and more preferably a phenyl group, a methylphenyl group, or an ethylphenyl group.
  • the carbon number of the aralkyl group which may have a substituent in R 31 to R 33 in the above formula (i) is not particularly limited, but is usually 7 or more and preferably 16 or less. The following is more preferable.
  • Specific examples of the aralkyl group include a phenylmethylene group, a phenylethylene group, a phenylpropylene group, a phenylbutylene group, and a phenylisopropylene group.
  • a phenylmethylene group, a phenylethylene group, a phenylpropylene group, or A phenylbutylene group is preferable, and a phenylmethylene group or a phenylethylene group is more preferable.
  • R 31 to R 33 are preferably each independently an alkyl group or an aralkyl group. Specifically, R 31 and R 33 are each independently a methyl group or an ethyl group. It is preferable that R 32 is a phenylmethylene group or a phenylethylene group, R 31 and R 33 are methyl groups, and R 32 is a phenylmethylene group.
  • the polymer dispersant when it has a tertiary amine as a functional group, from the viewpoint of dispersibility, it may be a repeating unit represented by the following formula (ii) (hereinafter referred to as “repeating unit (ii)”) .).
  • R 35 and R 36 each independently have a hydrogen atom, an alkyl group which may have a substituent, an aryl group which may have a substituent, or a substituent.
  • R 35 and R 36 may be bonded to each other to form a cyclic structure.
  • R 37 is a hydrogen atom or a methyl group.
  • Z is a divalent linking group.
  • alkyl group which may have a substituent in R 35 and R 36 of the above formula (ii) those exemplified as R 31 to R 33 of the above formula (i) may be preferably employed. it can.
  • aryl group which may have a substituent in R 35 and R 36 in the above formula (ii) those exemplified as R 31 to R 33 in the above formula (i) should be preferably employed.
  • aralkyl group optionally having a substituent in R 35 and R 36 in the above formula (ii) those exemplified as R 31 to R 33 in the above formula (i) may be preferably employed. it can.
  • R 35 and R 36 are preferably each independently an alkyl group which may have a substituent, and more preferably a methyl group or an ethyl group.
  • alkyl group, aralkyl group or aryl group in R 31 to R 33 of the above formula (i) and R 35 and R 36 of the above formula (ii) may have include a halogen atom, an alkoxy group, A benzoyl group, a hydroxyl group, etc. are mentioned.
  • examples of the divalent linking groups X and Z include, for example, an alkylene group having 1 to 10 carbon atoms, an arylene group having 6 to 12 carbon atoms, a —CONH—R 43 — group, —COOR 44 — group (wherein R 43 and R 44 are a single bond, an alkylene group having 1 to 10 carbon atoms, or an ether group (alkyloxyalkyl group) having 2 to 10 carbon atoms), etc. Is a —COO—R 44 — group.
  • examples of Y ⁇ of the counter anion include Cl ⁇ , Br ⁇ , I ⁇ , ClO 4 ⁇ , BF 4 ⁇ , CH 3 COO ⁇ , PF 6 ⁇ and the like.
  • the content rate of the repeating unit represented by the said formula (i) is not specifically limited, From a dispersible viewpoint, it is represented by the content rate of the repeating unit represented by the said formula (i), and the said formula (ii). Preferably it is 60 mol% or less, more preferably 50 mol% or less, still more preferably 40 mol% or less, particularly preferably 35 mol% or less, based on the total content of repeating units.
  • the amount is preferably 5 mol% or more, more preferably 10 mol% or more, still more preferably 20 mol% or more, and particularly preferably 30 mol% or more.
  • the content ratio of the repeating unit represented by the formula (i) in the total repeating units of the polymer dispersant is not particularly limited, but is preferably 1 mol% or more from the viewpoint of dispersibility, and 5 mol. % Or more, more preferably 10 mol% or more, more preferably 50 mol% or less, more preferably 30 mol% or less, and 20 mol% or less. Is more preferable, and it is especially preferable that it is 15 mol% or less.
  • the content ratio of the repeating unit represented by the formula (ii) in all the repeating units of the polymer dispersant is not particularly limited, but is preferably 5 mol% or more from the viewpoint of dispersibility. % Or more, more preferably 15 mol% or more, particularly preferably 20 mol% or more, more preferably 60 mol% or less, and 40 mol% or less. Is more preferably 30 mol% or less, and particularly preferably 25 mol% or less.
  • the polymer dispersant is a repeating unit represented by the following formula (iii) (hereinafter referred to as “repeating unit (iii)” from the viewpoint of improving compatibility with binder components such as a solvent and improving dispersion stability. It is preferable that it has.
  • R 40 is an ethylene group or a propylene group
  • R 41 is an alkyl group which may have a substituent
  • R 42 is a hydrogen atom or a methyl group.
  • n is an integer of 1 to 20.
  • the number of carbon atoms of the alkyl group which may have a substituent in R 41 of the above formula (iii) is not particularly limited, but is usually 1 or more, preferably 2 or more, and 10 or less. It is preferably 6 or less.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Among these, a methyl group, an ethyl group, a propyl group, and a butyl group are exemplified.
  • It is preferably a group, a pentyl group or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group or a butyl group. Further, it may be linear or branched. Further, it may contain a cyclic structure such as a cyclohexyl group or a cyclohexylmethyl group.
  • n in the above formula (iii) is preferably 1 or more, more preferably 2 or more, and preferably 10 or less from the viewpoints of compatibility with a binder component such as a solvent and dispersibility. More preferably, it is 5 or less.
  • the content ratio of the repeating unit represented by the formula (iii) in all the repeating units of the polymer dispersant is not particularly limited, but is preferably 1 mol% or more, and preferably 2 mol% or more. More preferably, it is 4 mol% or more, more preferably 30 mol% or less, more preferably 20 mol% or less, and even more preferably 10 mol% or less.
  • the amount is within the above range, compatibility with a binder component such as a solvent tends to be compatible with dispersion stability.
  • the polymer dispersant is a repeating unit represented by the following formula (iv) (hereinafter referred to as “repeating unit (iv)” from the viewpoint of improving the compatibility of the dispersing agent with a binder component such as a solvent and improving dispersion stability. ) ").).
  • R 38 represents an alkyl group which may have a substituent, an aryl group which may have a substituent, or an aralkyl group which may have a substituent.
  • R 39 is a hydrogen atom or a methyl group.
  • the number of carbon atoms of the alkyl group that may have a substituent in R 38 in the above formula (iv) is not particularly limited, but is usually 1 or more, preferably 2 or more, and preferably 4 or more. More preferably, it is preferably 10 or less, and more preferably 8 or less.
  • Specific examples of the alkyl group include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group. Among these, a methyl group, an ethyl group, a propyl group, and a butyl group are exemplified.
  • It is preferably a group, a pentyl group or a hexyl group, more preferably a methyl group, an ethyl group, a propyl group or a butyl group. Further, it may be linear or branched. Further, it may contain a cyclic structure such as a cyclohexyl group or a cyclohexylmethyl group.
  • the number of carbon atoms of the aryl group which may have a substituent in R 38 in the above formula (iv) is not particularly limited, but is usually 6 or more, preferably 16 or less, and preferably 12 or less. More preferably, it is more preferably 8 or less.
  • Specific examples of the aryl group include a phenyl group, a methylphenyl group, an ethylphenyl group, a dimethylphenyl group, a diethylphenyl group, a naphthyl group, and an anthracenyl group.
  • a phenyl group, a methylphenyl group, and an ethylphenyl group A dimethylphenyl group, or a diethylphenyl group, and more preferably a phenyl group, a methylphenyl group, or an ethylphenyl group.
  • the carbon number of the aralkyl group which may have a substituent in R 38 in the above formula (iv) is not particularly limited, but is usually 7 or more, preferably 16 or less, and preferably 12 or less. More preferred is 10 or less.
  • Specific examples of the aralkyl group include a phenylmethylene group, a phenylethylene group, a phenylpropylene group, a phenylbutylene group, and a phenylisopropylene group.
  • a phenylmethylene group, a phenylethylene group, a phenylpropylene group, or A phenylbutylene group is preferable, and a phenylmethylene group or a phenylethylene group is more preferable.
  • R 38 is preferably an alkyl group or an aralkyl group, and more preferably a methyl group, an ethyl group, or a phenylmethylene group from the viewpoints of solvent compatibility and dispersion stability.
  • the substituent that the aryl group or aralkyl group may have include a chain alkyl group, a halogen atom, and an alkoxy group.
  • the linear alkyl group represented by R 38 includes both linear and branched chains.
  • the content of the repeating unit represented by the formula (iv) in all the repeating units of the polymer dispersant is preferably 30 mol% or more and 40 mol% or more from the viewpoint of dispersibility. More preferably, it is more preferably 50 mol% or more, more preferably 80 mol% or less, and even more preferably 70 mol% or less.
  • the polymer dispersant may have a repeating unit other than the repeating unit (i), the repeating unit (ii), the repeating unit (iii), and the repeating unit (iv).
  • repeating units include styrene monomers such as styrene and ⁇ -methylstyrene; (meth) acrylate monomers such as (meth) acrylic acid chloride; (meth) acrylamide, N- (Meth) acrylamide monomers such as methylolacrylamide; vinyl acetate; acrylonitrile; allyl glycidyl ether, crotonic acid glycidyl ether; and repeating units derived from monomers such as N-methacryloylmorpholine.
  • the polymer dispersant is composed of an A block having the repeating unit (i) and the repeating unit (ii), and a B block not having the repeating unit (i) and the repeating unit (ii). It is preferable that it is a block copolymer which has these.
  • the block copolymer is preferably an AB block copolymer or a BAB block copolymer. By introducing not only a quaternary ammonium base but also a tertiary amino group into the A block, the dispersing ability of the dispersant tends to be remarkably improved.
  • the B block preferably has a repeating unit (iii), and more preferably has a repeating unit (iv).
  • the repeating unit (i) and the repeating unit (ii) may be contained in any form of random copolymerization and block copolymerization.
  • the repeating unit (i) and the repeating unit (ii) may be contained in two or more kinds in one A block. In that case, each repeating unit is randomly copolymerized in the A block. It may be contained in any form of block copolymerization.
  • a repeating unit other than the repeating unit (i) and the repeating unit (ii) may be contained in the A block.
  • Examples of such a repeating unit include the aforementioned (meth) acrylic acid ester-based unit.
  • Examples include a repeating unit derived from a monomer.
  • the content of the repeating unit other than the repeating unit (i) and the repeating unit (ii) in the A block is preferably 0 to 50 mol%, more preferably 0 to 20 mol%. Most preferably it is not contained in the block.
  • Repeating units other than the repeating units (iii) and (iv) may be contained in the B block, and examples of such repeating units include styrene monomers such as styrene and ⁇ -methylstyrene; (Meth) acrylate monomers such as (meth) acrylic acid chloride; (meth) acrylamide monomers such as (meth) acrylamide and N-methylolacrylamide; vinyl acetate; acrylonitrile; allyl glycidyl ether, glycidyl crotonic acid Ether; repeating units derived from monomers such as N-methacryloylmorpholine.
  • styrene monomers such as styrene and ⁇ -methylstyrene
  • (Meth) acrylate monomers such as (meth) acrylic acid chloride
  • (meth) acrylamide monomers such as (meth) acrylamide and N-methylolacrylamide
  • vinyl acetate acrylon
  • the content of the repeating unit other than the repeating unit (iii) and the repeating unit (iv) in the B block is preferably 0 to 50 mol%, more preferably 0 to 20 mol%. Most preferably it is not contained in the block.
  • the dispersant is preferably used in combination with a pigment derivative described later.
  • the (C) alkali-soluble resin used in the present invention is not particularly limited as long as it contains a carboxyl group or a hydroxyl group.
  • an epoxy (meth) acrylate resin, an acrylic resin, a carboxyl group-containing epoxy resin, a carboxyl group-containing resin is used.
  • a urethane resin, a novolac resin, a polyvinylphenol resin, and the like can be given.
  • an epoxy (meth) acrylate resin and an acrylic resin are preferable. These can be used individually by 1 type or in mixture of multiple types.
  • the alkali-soluble resin used in the present invention is particularly excellent in the following alkali-soluble resin (c1) and / or alkali-soluble resin (c2) (hereinafter sometimes referred to as “carboxyl group-containing epoxy (meth) acrylate resin”). It is preferably used from the viewpoint of plate making.
  • ⁇ Alkali-soluble resin (c1)> It was obtained by adding an ⁇ , ⁇ -unsaturated monocarboxylic acid or an ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group to an epoxy resin, and further reacting a polybasic acid and / or an anhydride thereof. Alkali-soluble resin.
  • epoxy resin used as a raw material for example, bisphenol A type epoxy resin (for example, “Epicoat (registered trademark; the same applies hereinafter) 828”, “Epicoat 1001”, “Epicoat 1002”, “Epicoat 1004” manufactured by Mitsubishi Chemical Corporation, etc. ), Epoxy obtained by reaction of alcoholic hydroxyl group of bisphenol A type epoxy resin and epichlorohydrin (for example, “NER-1302” manufactured by Nippon Kayaku Co., Ltd.
  • bisphenol A type epoxy resin for example, “Epicoat (registered trademark; the same applies hereinafter) 828
  • Epoxy obtained by reaction of alcoholic hydroxyl group of bisphenol A type epoxy resin and epichlorohydrin for example, “NER-1302” manufactured by Nippon Kayaku Co., Ltd.
  • a represents an average value and represents a number from 0 to 10.
  • R 111 represents any of a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a naphthyl group, and a biphenyl group.
  • a plurality of R 111 present in one molecule may be the same or different.
  • R 121 represents any one of a hydrogen atom, a halogen atom, an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 10 carbon atoms, a phenyl group, a naphthyl group, and a biphenyl group.
  • a plurality of R 121 present in one molecule may be the same or different.
  • X represents a linking group represented by the following general formula (C3-1) or (C3-2). However, one or more adamantane structures are included in the molecular structure.
  • c represents an integer of 2 or 3.
  • R 131 to R 134 and R 135 to R 137 are each independently an adamantyl group, a hydrogen atom, or a substituent which may have a substituent. And an alkyl group having 1 to 12 carbon atoms which may have a phenyl group which may have a substituent. * Indicates a bond.
  • p and q each independently represent an integer of 0 to 4
  • R 141 and R 142 each independently represent an alkyl group having 1 to 4 carbon atoms or a halogen atom
  • R 143 and R 144 each independently represents an alkylene group having 1 to 4 carbon atoms
  • x and y each independently represents an integer of 0 or more.
  • an epoxy resin represented by any one of the general formulas (C1) to (C4) it is preferable to use an epoxy resin represented by any one of the general formulas (C1) to (C4).
  • Examples of ⁇ , ⁇ -unsaturated monocarboxylic acid or ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group include (meth) acrylic acid, crotonic acid, o-, m- or p-vinylbenzoic acid, (meta ) Monocarboxylic acid such as ⁇ -position haloalkyl, alkoxyl, halogen, nitro, cyano substituent of acrylic acid, 2- (meth) acryloyloxyethyl succinic acid, 2- (meth) acryloyloxyethyl adipic acid, 2- ( (Meth) acryloyloxyethyl phthalic acid, 2- (meth) acryloyloxyethyl hexahydrophthalic acid, 2- (meth) acryloyloxyethyl maleic acid, 2- (meth) acryloyloxypropyl succinic acid, 2- (Meth) acryl
  • an ⁇ , ⁇ -unsaturated monocarboxylic acid or an ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group can be used as a method for adding an ⁇ , ⁇ -unsaturated monocarboxylic acid or an ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group.
  • a known method can be used as a method for adding an ⁇ , ⁇ -unsaturated monocarboxylic acid or an ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group.
  • an epoxy resin at a temperature of 50 to 150 ° C. in the presence of an esterification catalyst. it can.
  • esterification catalyst used here tertiary amines such as triethylamine, trimethylamine, benzyldimethylamine, and benzyldiethylamine, quaternary ammonium salts such as tetramethylammonium chloride, tetraethylammonium chloride, dodecyltrimethylammonium chloride, and the like can be used. .
  • the epoxy resin, ⁇ , ⁇ -unsaturated monocarboxylic acid or ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group, and esterification catalyst may be used alone or in combination of two types. You may use the above together.
  • the amount of ⁇ , ⁇ -unsaturated monocarboxylic acid or ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group is preferably in the range of 0.5 to 1.2 equivalents relative to 1 equivalent of epoxy group of the epoxy resin. More preferably, it is in the range of 0.7 to 1.1 equivalents.
  • Polybasic acids and / or anhydrides thereof include maleic acid, succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, benzophenone tetracarboxylic acid, methyl hexahydrophthal
  • examples thereof include one or more selected from acids, endomethylenetetrahydrophthalic acid, chlorendic acid, methyltetrahydrophthalic acid, biphenyltetracarboxylic acid, and anhydrides thereof.
  • maleic acid succinic acid, itaconic acid, phthalic acid, tetrahydrophthalic acid, hexahydrophthalic acid, pyromellitic acid, trimellitic acid, biphenyltetracarboxylic acid, or anhydrides thereof.
  • Particularly preferred is tetrahydrophthalic acid, biphenyltetracarboxylic acid, tetrahydrophthalic anhydride, or biphenyltetracarboxylic dianhydride.
  • a known method can be used for addition reaction of polybasic acid and / or anhydride thereof, and ⁇ , ⁇ -unsaturated monocarboxylic acid or ⁇ , ⁇ -unsaturated monocarboxylic acid having a carboxyl group to epoxy resin.
  • the target product can be obtained by continuing the reaction under the same conditions as in the ester addition reaction.
  • the addition amount of the polybasic acid and / or its anhydride component is preferably such that the acid value of the resulting carboxyl group-containing epoxy (meth) acrylate resin is in the range of 10 to 150 mgKOH / g, and further 20 The degree is preferably in the range of ⁇ 140 mgKOH / g.
  • the carboxyl group-containing epoxy (meth) acrylate resin is usually a polybasic acid and a reaction product of an epoxy resin and an ⁇ , ⁇ -unsaturated monocarboxylic acid or an ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group.
  • the mixing order of the polybasic acid and / or its anhydride and the polyfunctional alcohol is not particularly limited. Any hydroxyl group present in the mixture of the reaction product of the epoxy resin with the ⁇ , ⁇ -unsaturated monocarboxylic acid or the ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group and the polyfunctional alcohol by heating.
  • the polybasic acid and / or its anhydride Any hydroxyl group present in the mixture of the reaction product of the epoxy resin with the ⁇ , ⁇ -unsaturated monocarboxylic acid or the ⁇ , ⁇ -unsaturated monocarboxylic acid ester having a carboxyl group and the polyfunctional alcohol by heating.
  • the weight average molecular weight (Mw) in terms of polystyrene measured by gel permeation chromatography (GPC) of the carboxyl group-containing epoxy (meth) acrylate resin is usually 1000 or more, preferably 1500 or more, and usually 10,000 or less, preferably 8000. Below, more preferably 6000 or less. If the weight average molecular weight is small, the solubility in the developer is high, and if it is too large, the solubility in the developer is low.
  • the carboxyl group-containing epoxy (meth) acrylate resin may be used alone or as a mixture of two or more resins.
  • (C) alkali-soluble resin used by this invention may replace a part of above-mentioned carboxyl group-containing epoxy (meth) acrylate resin with another binder resin, unless the performance of this invention is impaired. That is, a carboxyl group-containing epoxy (meth) acrylate resin and another binder resin may be used in combination.
  • the proportion of the carboxyl group-containing epoxy (meth) acrylate resin in the alkali-soluble resin (C) alkali-soluble resin is preferably 50% by mass or more, particularly preferably 80% by mass or more.
  • binder resins that can be used in combination with the carboxyl group-containing epoxy (meth) acrylate resin are not limited, and may be selected from resins that are usually used in photosensitive coloring compositions. Examples thereof include binder resins described in Japanese Patent Application Publication No. 2007-271727, Japanese Patent Application Publication No. 2007-316620, Japanese Patent Application Publication No. 2007-334290, and the like.
  • binder resins may be used alone or in combination of two or more.
  • the photopolymerization initiator is a component having a function of directly absorbing light, causing a decomposition reaction or a hydrogen abstraction reaction, and generating a polymerization active radical. If necessary, an additive such as a polymerization accelerator (chain transfer agent) or a sensitizing dye may be added and used.
  • an additive such as a polymerization accelerator (chain transfer agent) or a sensitizing dye may be added and used. Examples of the photopolymerization initiator include metallocene compounds including titanocene compounds described in JP-A Nos. 59-152396 and 61-151197, and JP-A No. 2000-56118.
  • N-aryl- ⁇ -amino acids such as halomethylated oxadiazole derivatives, halomethyl-s-triazine derivatives and N-phenylglycine described in JP-A-10-39503; Radical activators such as -aryl- ⁇ -amino acid salts and N-aryl- ⁇ -amino acid esters, ⁇ -aminoalkylphenone derivatives; Japanese Patent Laid-Open No. 2000-80068, Japanese Patent Laid-Open No. 2006-36750 And the oxime ester derivatives described in the above.
  • titanocene derivatives include dicyclopentadienyl titanium dichloride, dicyclopentadienyl titanium bisphenyl, dicyclopentadienyl titanium bis (2,3,4,5,6-pentafluoro Phen-1-yl), dicyclopentadienyl titanium bis (2,3,5,6-tetrafluorophen-1-yl), dicyclopentadienyl titanium bis (2,4,6-trifluoropheny) 1-yl), dicyclopentadienyltitanium di (2,6-difluorophen-1-yl), dicyclopentadienyltitanium di (2,4-difluorophen-1-yl), di (methylcyclopenta Dienyl) titanium bis (2,3,4,5,6-pentafluorophen-1-yl), di (methylcyclone) Pentadienyl) titanium bis (2,6-difluorophen-1-yl), dicyclopentadieny
  • Biimidazole derivatives include 2- (2′-chlorophenyl) -4,5-diphenylimidazole dimer, 2- (2′-chlorophenyl) -4,5-bis (3′-methoxyphenyl) imidazole. Dimer, 2- (2′-fluorophenyl) -4,5-diphenylimidazole dimer, 2- (2′-methoxyphenyl) -4,5-diphenylimidazole dimer, (4′-methoxyphenyl) ) -4,5-diphenylimidazole dimer and the like.
  • halomethylated oxadiazole derivatives examples include 2-trichloromethyl-5- (2′-benzofuryl) -1,3,4-oxadiazole, 2-trichloromethyl-5- [ ⁇ - (2′- Benzofuryl) vinyl] -1,3,4-oxadiazole, 2-trichloromethyl-5- [ ⁇ - (2 ′-(6 ′′ -benzofuryl) vinyl)]-1,3,4-oxadiazole, 2 -Trichloromethyl-5-furyl-1,3,4-oxadiazole and the like.
  • halomethyl-s-triazine derivatives examples include 2- (4-methoxyphenyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-methoxynaphthyl) -4,6-bis ( Trichloromethyl) -s-triazine, 2- (4-ethoxynaphthyl) -4,6-bis (trichloromethyl) -s-triazine, 2- (4-ethoxycarbonylnaphthyl) -4,6-bis (trichloromethyl) -S-triazine and the like.
  • ⁇ -aminoalkylphenone derivatives include 2-methyl-1 [4- (methylthio) phenyl] -2-morpholinopropan-1-one, 2-benzyl-2-dimethylamino-1- (4- Morpholinophenyl) -butanone-1,2-benzyl-2-dimethylamino-1- (4-morpholinophenyl) butan-1-one, 4-dimethylaminoethylbenzoate, 4-dimethylaminoisoamylbenzoe -To, 4-diethylaminoacetophenone, 4-dimethylaminopropiophenone, 2-ethylhexyl-1,4-dimethylaminobenzoate, 2,5-bis (4-diethylaminobenzal) cyclohexanone, 7-diethylamino-3- (4 -Diethylaminobenzoyl) coumarin, 4- (diethylamino) chalcone, etc. It is
  • oxime derivatives are particularly effective in terms of sensitivity and plate-making properties, and in the case of using an alkali-soluble resin containing a phenolic hydroxyl group, in terms of sensitivity.
  • oxime derivatives oxime ester and ketoxime ester compounds
  • excellent in sensitivity are useful.
  • the oxime compound include a compound containing a structural moiety represented by the following general formula (3), and preferably include an oxime ester compound represented by the following general formula (3a).
  • R 22 is an optionally substituted alkanoyl group having 2 to 12 carbon atoms, a heteroarylalkanoyl group having 1 to 20 carbon atoms, an alkenoyl group having 3 to 25 carbon atoms, and 3 carbon atoms.
  • R 21a represents a hydrogen atom or an optionally substituted alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, or a heteroarylalkyl group having 1 to 20 carbon atoms.
  • R 21b represents an arbitrary substituent containing an aromatic ring or a heteroaromatic ring.
  • R 21a may form a ring together with R 21b , and the linking group may be a C 1-10 alkylene group which may have a substituent, a polyethylene group (— (CH ⁇ CH) r -), A polyethynylene group (-(C ⁇ C) r- ), or a group formed by a combination thereof (where r is an integer of 0 to 3).
  • R 22a is an optionally substituted alkanoyl group having 2 to 12 carbon atoms, a heteroarylalkanoyl group having 1 to 20 carbon atoms, an alkenoyl group having 3 to 25 carbon atoms, and 3 carbon atoms.
  • R 22 in the general formula (3) and R 22a in the general formula (3a) are preferably an alkanoyl group having 2 to 12 carbon atoms, a heteroarylalkanoyl group having 1 to 20 carbon atoms, or 3 to 8 carbon atoms.
  • R 21a in the general formula (3a) is preferably an unsubstituted methyl group, ethyl group, propyl group, or a propyl group substituted with an N-acetyl-N-acetoxyamino group.
  • R 21b in the general formula (3a) is preferably an optionally substituted carbazoyl group, an optionally substituted thioxanthonyl group, or an optionally substituted phenyl sulfide group.
  • an alkyl group, an aryl group, an alicyclic group, a heterocyclic group, a halogen group, a hydroxyl group, a carboxyl group, an amino group, an amide group etc. are mentioned. It is done.
  • Specific examples of the oxime ester-based compound suitable for the present invention include the compounds exemplified below, but the oxime ester-based compound is not limited to these compounds.
  • An oxime ester initiator having a carbazole group having a nitro group is also effective.
  • the ketoxime compound include a compound containing a structural moiety represented by the following general formula (4), and preferably an oxime ester compound represented by the following general formula (5).
  • R 24 has the same meaning as R 22 in Formula (3).
  • each R 23a may be a phenyl group, an alkyl group having 1 to 20 carbon atoms, an alkenyl group having 2 to 25 carbon atoms, or a heteroarylalkyl having 1 to 20 carbon atoms.
  • alkoxycarbonylalkyl group having 3 to 20 carbon atoms phenoxycarbonylalkyl group having 8 to 20 carbon atoms, alkylthioalkyl group having 2 to 20 carbon atoms, heteroaryloxycarbonylalkyl group having 1 to 20 carbon atoms or heteroarylthio group
  • R 23b represents an arbitrary substituent containing an aromatic ring or a heteroaromatic ring.
  • R 23a may form a ring together with R 23b , and the linking group may be an alkylene group having 1 to 10 carbon atoms which may have a substituent, a polyethylene group (— (CH ⁇ CH) r -), A polyethynylene group (-(C ⁇ C) r- ), or a group formed by a combination thereof (where r is an integer of 0 to 3).
  • R 24a is an optionally substituted alkanoyl group having 2 to 12 carbon atoms, an alkenoyl group having 3 to 25 carbon atoms, a cycloalkanoyl group having 4 to 8 carbon atoms, and 7 carbon atoms.
  • R 24 in the general formula (4) and R 24a in the general formula (5) are preferably an alkanoyl group having 2 to 12 carbon atoms, a heteroarylalkanoyl group having 1 to 20 carbon atoms, or 3 to 8 carbon atoms. And a cycloalkanoyl group and an aryloyl group having 7 to 20 carbon atoms.
  • R 23a in the general formula (5) is preferably an unsubstituted ethyl group, propyl group, butyl group, or an ethyl group or propyl group substituted with a methoxycarbonyl group.
  • R 23b in the general formula (5) is preferably an optionally substituted carbazoyl group or an optionally substituted phenyl sulfide group.
  • ketoxime ester-based compound suitable for the present invention include compounds exemplified below, but the ketoxime ester-based compound is not limited to these compounds.
  • the photopolymerization initiator is preferably an oxime ester initiator and / or a ketoxime ester initiator.
  • the said photoinitiator may be used individually by 1 type, and may use 2 or more types together.
  • the ratio of the photopolymerization initiator in the photosensitive coloring composition of the present invention is usually 0.4 to 15% by mass, preferably 0.5 to 10% by mass, based on the total solid content. If the ratio of the photopolymerization initiator is too much within this range, the developability tends to be reduced, while if it is too small, the preferred colored cured product shape and step may not be formed.
  • benzoin alkyl ethers such as benzoin methyl ether, benzoin phenyl ether, benzoin isobutyl ether and benzoin isopropyl ether; anthraquinone derivatives such as 2-methylanthraquinone, 2-ethylanthraquinone, 2-t-butylanthraquinone and 1-chloroanthraquinone
  • Benzophenone derivatives such as benzophenone, Michler's ketone, 2-methylbenzophenone, 3-methylbenzophenone, 4-methylbenzophenone, 2-chlorobenzophenone, 4-bromobenzophenone, 2-carboxybenzophenone; 2,2-dimethoxy-2-phenyl Acetophenone, 2,2-diethoxyacetophenone, 1-hydroxycyclohexyl phenyl ketone, ⁇ -hydroxy-2-methylphenol Nylpropanone, 1-hydroxy-1-methylethyl- (p-isopropyl
  • oxime ester derivatives are particularly preferable from the viewpoint of sensitivity.
  • oxime ester derivatives a photopolymerization initiator having a diphenyl sulfide skeleton is preferable from the viewpoint of solvent resistance.
  • those represented by the following general formula (5-1) can be used.
  • R 23a and R 24a have the same meaning as in the general formula (5).
  • R 25a and R 25b each independently represent R 25c , OR 25c , CN, OH, or a halogen atom, f represents an integer of 0 to 5, and g represents an integer of 0 to 4.
  • R 25c represents an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms.
  • the hydrogen atom of the substituent represented by R 25c may be further substituted with a halogen atom, and the alkylene moiety of the substituent represented by R 25c is —O—, —S—, —COO—, —OCO.
  • R 25d represents a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 30 carbon atoms, or an arylalkyl group having 7 to 30 carbon atoms.
  • the alkyl part of the substituent represented by R 25c may have a branched side chain, and may be cyclopentyl or cyclohexyl.
  • R 26 represents OH, COOH or a group represented by the following general formula (5-2), and h represents an integer of 0 to 5.
  • R 26a represents —O—, —S—, —OCO— or —COO—.
  • R 26b represents an alkylene group having 1 to 20 carbon atoms, an arylene group having 6 to 30 carbon atoms, or an arylene alkylene group having 7 to 30 carbon atoms.
  • the alkylene part of the substituent represented by R 26b may be interrupted 1 to 5 times by —O—, —S—, —COO— or —OCO—.
  • the alkylene part of the substituent represented by R 26b may have a branched side chain or cyclohexylene.
  • R 26c represents OH or COOH, and i represents an integer of 1 to 3. * Indicates a bond.
  • a photoinitiator may be used individually by 1 type, or may be used in combination of 2 or more type.
  • a sensitizing dye and a polymerization accelerator corresponding to the wavelength of the image exposure light source can be blended with the photopolymerization initiator as necessary for the purpose of increasing the sensitivity.
  • sensitizing dyes xanthene dyes described in Japanese Patent Application Laid-Open No. 4-221958, Japanese Patent Application Laid-Open No. 4-219756, Japanese Patent Application Laid-Open No. 3-239703, and Japanese Patent Application Laid-Open No. 5-289335 are described.
  • amino group-containing sensitizing dyes preferred are amino group-containing sensitizing dyes, and more preferred are compounds having an amino group and a phenyl group in the same molecule. Particularly preferred are, for example, 4,4′-dimethylaminobenzophenone, 4,4′-diethylaminobenzophenone, 2-aminobenzophenone, 4-aminobenzophenone, 4,4′-diaminobenzophenone, 3,3′-diaminobenzophenone.
  • Benzophenone compounds such as 3,4-diaminobenzophenone; 2- (p-dimethylaminophenyl) benzoxazole, 2- (p-diethylaminophenyl) benzoxazole, 2- (p-dimethylaminophenyl) benzo [4,5 ] Benzoxazole, 2- (p-dimethylaminophenyl) benzo [6,7] benzoxazole, 2,5-bis (p-diethylaminophenyl) -1,3,4-oxazole, 2- (p-dimethylaminophenyl) ) Benzothiazole, 2- (p-diethi) Ruaminophenyl) benzothiazole, 2- (p-dimethylaminophenyl) benzimidazole, 2- (p-diethylaminophenyl) benzimidazole, 2,5-bis (p-diethylaminophenyl) -1,3,4-thiadiazol
  • polymerization accelerator examples include aromatic amines such as ethyl p-dimethylaminobenzoate and 2-dimethylaminoethyl benzoate, aliphatic amines such as n-butylamine and N-methyldiethanolamine, and mercapto compounds described later. It is done.
  • a polymerization accelerator may be used individually by 1 type, or may be used in combination of 2 or more type.
  • photopolymerizable monomer In the photosensitive coloring composition of this invention, it is preferable from points, such as a sensitivity, that a photopolymerizable monomer (photopolymerizable compound) is further included.
  • the photopolymerizable monomer used in the present invention include compounds having at least one ethylenically unsaturated group in the molecule (hereinafter sometimes referred to as “ethylenic monomer”). Specifically, for example, (meth) acrylic acid, (meth) acrylic acid alkyl ester, acrylonitrile, styrene, a carboxylic acid having one ethylenically unsaturated bond, a monoester of polyhydric or monohydric alcohol, etc. Can be mentioned.
  • polyfunctional ethylenic monomers having two or more ethylenically unsaturated groups in one molecule.
  • polyfunctional ethylenic monomers include, for example, esters of aliphatic polyhydroxy compounds and unsaturated carboxylic acids; esters of aromatic polyhydroxy compounds and unsaturated carboxylic acids; aliphatic polyhydroxy compounds, aromatics Examples thereof include esters obtained by an esterification reaction of a polyvalent hydroxy compound such as a polyhydroxy compound with an unsaturated carboxylic acid and a polybasic carboxylic acid.
  • ester of the aliphatic polyhydroxy compound and the unsaturated carboxylic acid examples include ethylene glycol diacrylate, triethylene glycol diacrylate, trimethylolpropane triacrylate, trimethylolethane triacrylate, pentaerythritol diacrylate, pentaerythritol triacrylate, Acrylic acid esters of aliphatic polyhydroxy compounds such as pentaerythritol tetraacrylate, dipentaerythritol tetraacrylate, dipentaerythritol pentaacrylate, dipentaerythritol hexaacrylate, glycerol acrylate, etc.
  • itaconic acid ester replaced by itaconate
  • ester of an aromatic polyhydroxy compound and an unsaturated carboxylic acid examples include acrylic acid esters and methacrylic acid esters of aromatic polyhydroxy compounds such as hydroquinone diacrylate, hydroquinone dimethacrylate, resorcin diacrylate, resorcin dimethacrylate, pyrogallol triacrylate and the like. Etc.
  • the ester obtained by the esterification reaction of a polybasic carboxylic acid and an unsaturated carboxylic acid and a polyvalent hydroxy compound is not necessarily a single substance, but representative examples include acrylic acid, phthalic acid, and Examples include condensates of ethylene glycol, condensates of acrylic acid, maleic acid and diethylene glycol, condensates of methacrylic acid, terephthalic acid and pentaerythritol, condensates of acrylic acid, adipic acid, butanediol and glycerin.
  • a polyisocyanate compound and a hydroxyl group-containing (meth) acrylate ester or a polyisocyanate compound and a polyol and a hydroxyl group-containing (meth) acrylate ester are reacted.
  • urethane (meth) acrylates examples include DPHA-40H, UX-5000, UX-5002D-P20, UX-5003, UX-5005 (manufactured by Nippon Kayaku Co., Ltd.), U-2PPA, U-6LPA, U -10PA, U-33H, UA-53H, UA-32P, UA-1100H (manufactured by Shin-Nakamura Chemical Co., Ltd.), UA-306H, UA-510H, UF-8001G (manufactured by Kyoeisha Chemical Co., Ltd.), UV-1700B , UV-7600B, UV-7605B, UV-7630B, UV7640B (manufactured by Nippon Synthetic Chemical). These may be used alone or in combination of two or more.
  • the photosensitive coloring composition of the present invention includes adhesion improvers such as organic solvents and silane coupling agents, coatability improvers, development improvers, ultraviolet absorbers, antioxidants, and surfactants.
  • adhesion improvers such as organic solvents and silane coupling agents, coatability improvers, development improvers, ultraviolet absorbers, antioxidants, and surfactants.
  • pigment derivatives and the like can be appropriately blended.
  • the photosensitive coloring composition of the present invention is usually used as (A) a color material, (B) a dispersant, (C) an alkali-soluble resin, (D) a photopolymerization initiator, and as required.
  • the photopolymerizable monomer and other various materials used are dissolved or dispersed in an organic solvent. It is preferable to select an organic solvent having a boiling point in the range of 100 to 300 ° C. A solvent having a boiling point of 120 to 280 ° C. is more preferable.
  • organic solvents include the following. Ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol mono-n-butyl ether, propylene glycol t-butyl ether, diethylene glycol monomethyl Ether, diethylene glycol monoethyl ether, diethylene glycol mono-n-butyl ether, methoxymethylpentanol, dipropylene glycol monoethyl ether, dipropylene glycol monomethyl ether, 3-methyl-3-methoxybutanol, triethylene glycol monomethyl ether, triethylene glycol Monoe Ether, glycol monoalkyl ethers such as tripropylene glycol methyl ether; Glycol dialkyl ethers such as ethylene glycol dimethyl ether, ethylene glycol diethyl
  • acetone Like acetone, methyl ethyl ketone, methyl amyl ketone, methyl isopropyl ketone, methyl isoamyl ketone, diisopropyl ketone, diisobutyl ketone, methyl isobutyl ketone, cyclohexanone, ethyl amyl ketone, methyl butyl ketone, methyl hexyl ketone, methyl nonyl ketone, methoxymethyl pentanone Ketones; Mono- or polyhydric alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, propylene glycol, butanediol, diethylene glycol, dipropylene glycol, triethylene glycol, methoxymethylpentanol, glycerin, benzyl alcohol; aliphatic hydrocarbons such as n-pentan
  • Aromatic hydrocarbons such as benzene, toluene, xylene, cumene; Amyl formate, ethyl formate, ethyl acetate, butyl acetate, propyl acetate, amyl acetate, methyl isobutyrate, ethylene glycol acetate, ethyl propionate, propyl propionate, butyl butyrate, isobutyl butyrate, methyl isobutyrate, ethyl Caprylate, butyl stearate, ethyl benzoate, methyl 3-ethoxypropionate, ethyl 3-ethoxypropionate, methyl 3-methoxypropionate, ethyl 3-methoxypropionate, propyl 3-methoxypropionate, 3-methoxypropionic acid Linear or cyclic esters such as butyl, ⁇ -butyrolactone; Alkoxycarboxylic acids such as 3-methoxy
  • solvents corresponding to the above include mineral spirit, Barsol # 2, Apco # 18 Solvent, Apco thinner, Soal Solvent No. 1 and no. 2, Solvesso # 150, Shell TS28 Solvent, carbitol, ethyl carbitol, butyl carbitol, methyl cellosolve ("Cerosolve” is a registered trademark, the same shall apply hereinafter), ethyl cellosolve, ethyl cellosolve acetate, methyl cellosolve acetate, diglyme (any Product name). These organic solvents may be used alone or in combination of two or more.
  • the organic solvent has a boiling point in the range of 100 to 200 ° C. (under pressure of 101.25 [hPa]. Hereinafter, all of the boiling points are the same). It is preferable to select one. More preferably, it has a boiling point of 120 to 170 ° C.
  • glycol alkyl ether acetates are preferred from the viewpoints of good balance of coatability, surface tension and the like, and relatively high solubility of the constituent components in the composition.
  • glycol alkyl ether acetates may be used alone or in combination with other organic solvents.
  • glycol monoalkyl ethers are particularly preferable.
  • propylene glycol monomethyl ether is particularly preferred because of the solubility of the constituent components in the composition.
  • Glycol monoalkyl ethers are highly polar, and if the amount added is too large, the pigment tends to aggregate, and the storage stability such as the viscosity of the colored resin composition obtained later tends to decrease.
  • the proportion of glycol monoalkyl ethers in the solvent is preferably 5% by mass to 30% by mass, and more preferably 5% by mass to 20% by mass.
  • an organic solvent having a boiling point of 150 ° C. or higher (hereinafter sometimes referred to as “high boiling point solvent”).
  • high boiling point solvent an organic solvent having a boiling point of 150 ° C. or higher
  • the colored resin composition becomes difficult to dry, but it has an effect of preventing the uniform dispersion state of the pigment in the composition from being destroyed by rapid drying. That is, for example, there is an effect of preventing the occurrence of a foreign matter defect due to precipitation and solidification of a coloring material at the tip of the slit nozzle.
  • diethylene glycol mono-n-butyl ether, diethylene glycol mono-n-butyl ether acetate, and diethylene glycol monoethyl ether acetate are particularly preferred because of their high effects.
  • the content of the high boiling point solvent in the organic solvent is preferably 3% by mass to 50% by mass, more preferably 5% by mass to 40% by mass, and particularly preferably 5% by mass to 30% by mass. If the amount of the high boiling point solvent is too small, for example, a coloring material may precipitate and solidify at the tip of the slit nozzle to cause foreign matter defects, and if it is too large, the drying temperature of the composition will be slowed down. There is a concern that problems such as tact defects in the reduced-pressure drying process and pin marks of prebaking may be caused in the matrix manufacturing process.
  • the high boiling point solvent having a boiling point of 150 ° C. or higher may be glycol alkyl ether acetates or glycol alkyl ethers. In this case, a high boiling point solvent having a boiling point of 150 ° C. or higher is separately contained. It doesn't have to be.
  • Preferred high boiling solvents include, for example, diethylene glycol mono-n-butyl ether acetate, diethylene glycol monoethyl ether acetate, dipropylene glycol methyl ether acetate, 1,3-butylene glycol diacetate, and 1,6-hexanol diester. Examples include acetate and triacetin.
  • the photosensitive coloring composition of the present invention may contain an adhesion improver in order to improve the adhesion to the substrate.
  • an adhesion improver a silane coupling agent, a phosphoric acid group-containing compound and the like are preferable.
  • the kind of the silane coupling agent various kinds such as epoxy, (meth) acrylic and amino can be used alone or in combination of two or more.
  • Preferred silane coupling agents include, for example, (meth) acryloxysilanes such as 3-methacryloxypropylmethyldimethoxysilane and 3-methacryloxypropyltrimethoxysilane, and 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane.
  • Epoxy silanes such as 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, and ureidosilanes such as 3-ureidopropyltriethoxysilane, Isocyanate silanes such as 3-isocyanatopropyltriethoxysilane are mentioned, and epoxy silane silane coupling agents are particularly preferable.
  • the phosphoric acid group-containing compound (meth) acryloyl group-containing phosphates are preferable, and those represented by the following general formula (g1), (g2) or (g3) are preferable.
  • R 51 represents a hydrogen atom or a methyl group
  • l and l ′ are integers of 1 to 10
  • m is 1, 2 or 3.
  • These phosphoric acid group-containing compounds may be used alone or in combination of two or more.
  • the photosensitive coloring composition of the present invention may contain a surfactant in order to improve coatability.
  • surfactant for example, various types such as anionic, cationic, nonionic, and amphoteric surfactants can be used.
  • nonionic surfactants are preferably used because they are less likely to adversely affect various properties, and among them, fluorine-based and silicon-based surfactants are effective in terms of coatability.
  • fluorine-based and silicon-based surfactants include TSF4460 (manufactured by GE Toshiba Silicone), DFX-18 (manufactured by Neos), BYK-300, BYK-325, BYK-330 (manufactured by BYK Chemie), and KP340 (Shin-Etsu Silicone).
  • F-470, F-475, F-478, F-559 DIC
  • SH7PA Toray Silicone
  • DS-401 Daikin
  • L-77 Long Term Evolution
  • FC4430 manufactured by Sumitomo 3M
  • 1 type may be used for surfactant and it may use 2 or more types together by arbitrary combinations and a ratio.
  • the photosensitive coloring composition of the present invention may contain a pigment derivative as a dispersion aid in order to improve dispersibility and storage stability.
  • a pigment derivative as a dispersion aid
  • As pigment derivatives azo, phthalocyanine, quinacridone, benzimidazolone, quinophthalone, isoindolinone, dioxazine, anthraquinone, indanthrene, perylene, perinone, diketopyrrolopyrrole, dioxazine
  • derivatives such as phthalocyanines and quinophthalones are preferable.
  • Substituents of pigment derivatives include sulfonic acid groups, sulfonamide groups and quaternary salts thereof, phthalimidomethyl groups, dialkylaminoalkyl groups, hydroxyl groups, carboxyl groups, amide groups, etc. directly on the pigment skeleton or alkyl groups, aryl groups, and complex groups. Examples thereof include those bonded via a ring group and the like, and a sulfonic acid group is preferable. Further, a plurality of these substituents may be substituted on one pigment skeleton.
  • pigment derivatives include phthalocyanine sulfonic acid derivatives, quinophthalone sulfonic acid derivatives, anthraquinone sulfonic acid derivatives, quinacridone sulfonic acid derivatives, diketopyrrolopyrrole sulfonic acid derivatives, and dioxazine sulfonic acid derivatives. These may be used alone or in combination of two or more.
  • Photoacid generator is a compound capable of generating an acid by ultraviolet rays, and has a crosslinking agent such as a melamine compound due to the action of an acid generated upon exposure. The crosslinking reaction will proceed.
  • a crosslinking agent such as a melamine compound due to the action of an acid generated upon exposure.
  • the crosslinking reaction will proceed.
  • photoacid generators those having a high solubility in a solvent, particularly in a solvent used in a photosensitive coloring composition, are preferable, for example, diphenyliodonium, ditolyliodonium, phenyl (p-anisyl).
  • Iodonium bis (m-nitrophenyl) iodonium, bis (p-tert-butylphenyl) iodonium, bis (p-chlorophenyl) iodonium, bis (n-dodecyl) iodonium, p-isobutylphenyl (p-tolyl) iodonium, p Diaryl iodonium such as isopropylphenyl (p-tolyl) iodonium, or triarylsulfonium chloride such as triphenylsulfonium, bromide, borofluoride, hexafluorophosphate salt, hexafluoroa Senate salts, aromatic sulfonates, tetrakis (pentafluorophenyl) borate salts and the like, sulfonium organoboron complexes such as diphenylphenacylsulfonium (n-butyl) triphen
  • Crosslinking agent can be further added to the photosensitive coloring composition of the present invention.
  • a melamine or guanamine compound can be used.
  • these cross-linking agents include melamine or guanamine compounds represented by the following general formula (6).
  • R 61 represents a —NR 66 R 67 group or an aryl group having 6 to 12 carbon atoms
  • R 61 represents R 62, R 63 , R 64 , R 65 one of R 66 and R 67
  • R 61 represents R 62, R 63, one of R 64 and R 65 are -CH 2 oR 68 group in the case of an aryl group having 6 to 12 carbon atoms
  • R 62 , R 63 , R 64 , R 65 , R 66 and R 67 independently of one another, represent hydrogen or a —CH 2 OR 68 group, wherein R 68 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
  • the aryl group having 6 to 12 carbon atoms is typically a phenyl group, 1-naphthyl group or 2-naphthyl group, and these phenyl group and naphthyl group include an alkyl group, an alkoxy group, a halogen atom, etc. May be bonded to each other.
  • Each of the alkyl group and the alkoxy group may have about 1 to 6 carbon atoms.
  • Alkyl group represented by R 68 is, among the above, methyl group or an ethyl group, especially a methyl group.
  • Melamine compounds corresponding to the general formula (6) that is, compounds of the following general formula (6-1) include hexamethylol melamine, pentamethylol melamine, tetramethylol melamine, hexamethoxymethyl melamine, pentamethoxymethyl melamine, tetramethoxy Methyl melamine, hexaethoxymethyl melamine and the like are included.
  • R 62 , R 63 , R 64 , R 65 , R 66 and R 67 when one of R 62 , R 63 , R 64 , R 65 , R 66 and R 67 is an aryl group, one of R 62 , R 63 , R 64 and R 65 is —CH 2.
  • guanamine compounds corresponding to the general formula (6) that is, compounds in which R 61 in the general formula (6) is aryl include tetramethylol benzoguanamine, tetramethoxymethyl benzoguanamine, trimethoxymethyl benzoguanamine, tetraethoxymethyl benzoguanamine. Etc. are included.
  • a crosslinking agent having a methylol group or a methylol alkyl ether group can also be used. Examples are given below. 2,6-bis (hydroxymethyl) -4-methylphenol, 4-tert-butyl-2,6-bis (hydroxymethyl) phenol, 5-ethyl-1,3-bis (hydroxymethyl) perhydro-1,3 , 5-triazin-2-one (commonly known as N-ethyldimethyloltriazone) or its dimethyl ether, dimethylol trimethylene urea or its dimethyl ether, 3,5-bis (hydroxymethyl) perhydro-1,3,5- Oxadiazin-4-one (commonly called dimethyloluron) or a dimethyl ether thereof, tetramethylol glyoxal diurein or a tetramethyl ether thereof.
  • crosslinking agents may be used individually by 1 type, or may be used in combination of 2 or more type.
  • the amount of the crosslinking agent used is preferably 0.1 to 15% by mass, particularly preferably 0.5 to 10% by mass, based on the total solid content of the photosensitive coloring composition.
  • Mercapto compounds include 2-mercaptobenzothiazole, 2-mercaptobenzoxazole, 2-mercaptobenzimidazole, hexanedithiol, decandithiol, 1,4-dimethylmercaptobenzene, butanediol bisthiopropionate, butanediol bis Thioglycolate, ethylene glycol bisthioglycolate, trimethylolpropane tristhioglycolate, butanediol bisthiopropionate, trimethylolpropane tristhiopropionate, trimethylolpropane tristhioglycolate, pentaerythritol tetrakisthiopropioate , Pentaerythritol tetrakisthioglycolate, trishydroxyethyltristhiopropionate, ethylene glycol (3-mercaptobutyrate), butanediol bis (3-mercapto
  • the content of (A) the coloring material is usually preferably 10% by mass or more and 20% by mass or more with respect to the total solid content in the photosensitive coloring composition. Usually, it is 50 mass% or less.
  • the content ratio of the (A-1) organic black pigment to (A) 100% by mass of the color material is usually 10% by mass or more, preferably 30% by mass or more, and usually 100% by mass or less. If the content of the (A-1) organic black pigment in the color material (A) is too small, a sufficient optical density (OD) may not be obtained.
  • the coloring material may contain (A-1) an organic black pigment and (A-2) an organic coloring pigment.
  • the content ratio of (A-1) organic black pigment to 100% by mass of (A) color material is usually 10% by mass or more, preferably 20% by mass or more, more preferably 30% by mass or more, and usually 90% by mass.
  • it is preferably 80% by mass or less, more preferably 60% by mass or less.
  • the content of the (A-2) organic coloring pigment is usually 10% by mass or more, preferably 20% by mass or more, more preferably 40% by mass or more, and usually 90% by mass or less, preferably 80% by mass.
  • it is 70 mass% or less more preferably.
  • the content ratio of (A-1) organic black pigment to (A-2) 100 parts by weight of organic coloring pigment is usually 15 parts by weight or more, preferably 20 parts by weight or more, and usually 900 parts by weight or less, preferably 800 parts by weight. Part or less, more preferably 500 parts by weight or less, and still more preferably 200 parts by weight or less.
  • the coloring material may contain (A-1) an organic black pigment and (A-3) carbon black.
  • the content ratio of (A-1) organic black pigment to 100% by mass of (A) color material is usually 50% by mass or more, preferably 60% by mass or more, and usually 95% by mass or less, preferably 90% by mass.
  • the content of (A-3) carbon black is usually 5% by mass or more, preferably 10% by mass or more, and usually 50% by mass or less, preferably 40% by mass or less.
  • the content ratio of (A-1) organic black pigment to (A-3) 100 parts by mass of carbon black is usually 100 parts by mass or more, preferably 150 parts by mass or more, usually 2000 parts by mass or less, preferably 1000 parts by mass. It is as follows.
  • the (A) coloring material may contain (A-2) an organic coloring pigment and (A-3) carbon black together with (A-1) an organic black pigment. is there.
  • the content ratio of (A-1) organic black pigment to 100% by mass of (A) color material is usually 10% by mass or more, preferably 20% by mass or more, and usually 80% by mass or less, preferably 70% by mass or less. It is.
  • the content of the (A-2) organic coloring pigment is usually 10% by mass or more, preferably 20% by mass or more, and usually 60% by mass or less, preferably 50% by mass or less.
  • the content of (A-3) carbon black is usually 5% by mass or more, preferably 10% by mass or more, and usually 50% by mass or less, preferably 40% by mass or less.
  • the content ratio of (A-1) organic black pigment to 100 parts by mass of (A-2) organic color pigment is usually 15 parts by mass or more, preferably 20 parts by mass or more, and usually 800 parts by mass or less, preferably 700 parts by mass. It is below mass parts.
  • the content ratio of (A-1) organic black pigment to (A-3) 100 parts by mass of carbon black is usually 40 parts by mass or more, preferably 50 parts by mass or more, and usually 1000 parts by mass or less, preferably 900 parts by mass. It is as follows.
  • (B) Content of a dispersing agent is 1 mass% or more normally in solid content of a photosensitive coloring composition, 3 mass% or more is preferable, 5 mass% or more is more preferable, and usually 30 mass% or less, 20 mass% or less is preferable and 15 mass% or less is especially preferable. Further, the content of the dispersant (B) with respect to 100% by mass of the (A) colorant is usually preferably 5% by mass or more and 10% by mass or more, and usually 50% by mass or less, particularly 30% by mass or less. preferable. (B) If the content of the dispersant is too small, sufficient dispersibility may not be obtained, and if it is too much, the proportion of other components may be relatively decreased, and sensitivity, plate-making property, etc. may be decreased. .
  • (C) Content of alkali-soluble resin is 5 mass% or more normally with respect to the total solid of the photosensitive coloring composition of this invention, Preferably it is 10 mass% or more, Usually 85 mass% or less, Preferably 80% by mass or less.
  • (D) Content of a photoinitiator is 0.1 mass% or more normally with respect to the total solid of the photosensitive coloring composition of this invention, Preferably it is 0.5 mass% or more, More preferably, it is 1 mass. %, Usually 15% by mass or less, preferably 10% by mass or less.
  • the content of the polymerization accelerator is preferably 0.05% by mass or more, and usually 0.05% by mass or more, based on the total solid content of the photosensitive coloring composition of the present invention. 10% by mass or less, preferably 5% by mass or less, and the polymerization accelerator is usually 0.1 to 50 parts by mass, particularly 0.1 to 20 parts by mass with respect to 100 parts by mass of the photopolymerization initiator (D). It is preferable to use in proportion.
  • the blending ratio of the sensitizing dye in the photosensitive coloring composition of the present invention is usually 20% by mass or less, preferably 15% by mass or less, based on the total solid content in the photosensitive coloring composition from the viewpoint of sensitivity. Preferably it is 10 mass% or less.
  • a photopolymerizable monomer When a photopolymerizable monomer is used, its content is usually 30% by mass or less, preferably 20% by mass or less, based on the total solid content of the photosensitive coloring composition. When there is too much content of a photopolymerizable monomer, the permeability
  • the minimum of content of a photopolymerizable monomer is 1 mass% or more normally, Preferably it is 5 mass% or more.
  • an adhesion improver When an adhesion improver is used, its content is usually 0.1 to 5% by mass, preferably 0.2 to 3% by mass, more preferably 0.4%, based on the total solid content in the photosensitive coloring composition. ⁇ 2% by weight. If the content of the adhesion improver is less than the above range, the effect of improving the adhesion may not be sufficiently obtained. If the content is too large, the sensitivity may be lowered, or the residue may remain as a defect after development. .
  • the content is usually 0.001 to 10% by mass, preferably 0.005 to 1% by mass, more preferably 0, based on the total solid content in the photosensitive coloring composition. 0.01 to 0.5% by mass, most preferably 0.03 to 0.3% by mass. If the surfactant content is less than the above range, the smoothness and uniformity of the coating film may not be expressed. If the content is too high, the smoothness and uniformity of the coating film may not be expressed, and other characteristics deteriorate. There is a case.
  • the photosensitive coloring composition of the present invention is prepared using the above-mentioned organic solvent so that the solid content concentration is usually 5 to 50% by mass, preferably 10 to 30% by mass.
  • the photosensitive coloring composition of the present invention can be suitably used for forming a black matrix, and preferably exhibits a black color from such a viewpoint, and has an optical density (OD) per 1 ⁇ m film thickness of the coating film. It is preferable that it is 1.0 or more.
  • the photosensitive coloring composition of the present invention (hereinafter sometimes referred to as “resist”) is produced according to a conventional method. Usually, it is preferable to disperse (A) the color material in advance using a paint conditioner, a sand grinder, a ball mill, a roll mill, a stone mill, a jet mill, a homogenizer, or the like. Since the colorant (A) is finely divided by the dispersion treatment, the resist coating characteristics are improved.
  • the dispersion treatment is usually preferably carried out in a system in which (A) a color material, an organic solvent, (B) a dispersant, and (C) a part or all of an alkali-soluble resin are used in combination (hereinafter referred to as dispersion treatment).
  • the mixture to be provided and the composition obtained by the treatment may be referred to as “ink” or “pigment dispersion”).
  • a polymer dispersant as the dispersant (B) because the resulting ink and resist are prevented from thickening with time (excellent in dispersion stability).
  • a pigment dispersion containing at least (A) a color material, an organic solvent, and (B) a dispersant.
  • A) colorant, organic solvent, and (B) dispersant that can be used in the pigment dispersion those described as those that can be used in the photosensitive coloring composition can be preferably employed.
  • a highly reactive component may be modified due to heat generated during the dispersion treatment. Therefore, it is preferable to perform the dispersion treatment in a system containing a polymer dispersant.
  • the color material (A) is dispersed with a sand grinder, glass beads or zirconia beads having a diameter of about 0.1 to 8 mm are preferably used.
  • the temperature is usually from 0 ° C. to 100 ° C., and preferably from room temperature to 80 ° C.
  • the dispersion time is appropriately adjusted because the appropriate time varies depending on the composition of the liquid and the size of the dispersion treatment apparatus.
  • the standard of dispersion is to control the gloss of the ink so that the 20-degree specular gloss (JIS Z8741) of the resist is in the range of 50 to 300.
  • the dispersion treatment is not sufficient, and rough pigment (coloring material) particles often remain, which may result in insufficient developability, adhesion, resolution, and the like.
  • the dispersion treatment is performed until the gloss value exceeds the above range, the pigment is crushed and a large number of ultrafine particles are generated, so that the dispersion stability tends to be impaired.
  • the dispersed particle diameter of the pigment dispersed in the ink is usually 0.03 to 0.3 ⁇ m, and is measured by a dynamic light scattering method or the like.
  • the ink obtained by the dispersion treatment and the other components contained in the resist are mixed to obtain a uniform solution.
  • fine dust is often mixed in the liquid, and thus the obtained resist is preferably filtered by a filter or the like.
  • a cured product can be obtained by curing the photosensitive coloring composition of the present invention.
  • a cured product obtained by curing the photosensitive coloring composition can be suitably used as a black matrix or a colored spacer.
  • the support for forming the black matrix is not particularly limited as long as it has an appropriate strength.
  • a transparent substrate is mainly used, but the material is, for example, a polyester resin such as polyethylene terephthalate, a polyolefin resin such as polypropylene or polyethylene, a sheet made of a thermoplastic resin such as polycarbonate, polymethyl methacrylate or polysulfone, or an epoxy resin. And thermosetting resin sheets such as unsaturated polyester resins and poly (meth) acrylic resins, and various glasses. Among these, glass and heat resistant resin are preferable from the viewpoint of heat resistance.
  • a transparent electrode such as ITO or IZO is formed on the surface of the substrate. Other than the transparent substrate, it can be formed on the TFT array.
  • the support may be subjected to corona discharge treatment, ozone treatment, silane coupling agent, thin film formation treatment of various resins such as urethane resin, etc., if necessary, in order to improve surface properties such as adhesiveness.
  • the thickness of the transparent substrate is usually 0.05 to 10 mm, preferably 0.1 to 7 mm. When a thin film forming process of various resins is performed, the film thickness is usually 0.01 to 10 ⁇ m, preferably 0.05 to 5 ⁇ m.
  • the photosensitive coloring composition of the present invention is applied on a transparent substrate and dried, and then the photosensitive matrix is coated.
  • a black mask is formed by placing a photomask on the coloring composition and exposing the image through the photomask, developing, and thermosetting or photocuring as necessary.
  • the black matrix of the present invention is effective for forming on the TFT element substrate, but the configuration is not particularly limited in each of the COA and BOA systems, and can be applied to various configurations. .
  • the photosensitive coloring composition for black matrix is applied on a transparent substrate by spinner method, wire bar method, flow coating method, die coating method. , Roll coating method or spray coating method.
  • the die coating method significantly reduces the amount of coating solution used, and has no influence from mist adhering to the spin coating method. To preferred.
  • the thickness of the coating film is usually preferably in the range of 0.2 to 10 ⁇ m, more preferably in the range of 0.5 to 6 ⁇ m, and still more preferably in the range of 1 to 4 ⁇ m, as the film thickness after drying. is there.
  • the coating film after the photosensitive coloring composition is applied to the substrate is preferably dried by a drying method using a hot plate, an IR oven, or a convection oven. Drying conditions can be appropriately selected according to the type of the solvent component, the performance of the dryer used, and the like.
  • the drying time is usually selected within the range of 15 seconds to 5 minutes at a temperature of 40 to 200 ° C., preferably 50 to 130 ° C., depending on the type of solvent component and the performance of the dryer used. It is selected in the range of 30 seconds to 3 minutes. The higher the drying temperature, the better the adhesion of the coating film to the transparent substrate.
  • the drying process of this coating film may be a reduced pressure drying method in which drying is performed in a reduced pressure chamber without increasing the temperature.
  • Exposure Image exposure is performed by overlaying a negative mask pattern on the coating film of the photosensitive coloring composition and irradiating an ultraviolet light source or a visible light source through the mask pattern. At this time, if necessary, exposure may be performed after an oxygen blocking layer such as a polyvinyl alcohol layer is formed on the photopolymerizable coating film in order to prevent a decrease in sensitivity of the photopolymerizable layer due to oxygen.
  • the light source used for said image exposure is not specifically limited.
  • Examples of the light source include a xenon lamp, a halogen lamp, a tungsten lamp, a high-pressure mercury lamp, an ultra-high pressure mercury lamp, a metal halide lamp, a medium-pressure mercury lamp, a low-pressure mercury lamp, a carbon arc, and a fluorescent lamp, an argon ion laser, a YAG laser, Examples include an excimer laser, a nitrogen laser, a helium cadmium laser, and a laser light source such as a semiconductor laser. An optical filter can also be used when used by irradiating light of a specific wavelength.
  • the black matrix according to the present invention comprises an organic solvent or an aqueous solution containing a surfactant and an alkaline compound after the coating film made of the photosensitive coloring composition is subjected to image exposure with the above light source.
  • An image can be formed on a substrate by development using a film.
  • This aqueous solution may further contain an organic solvent, a buffering agent, a complexing agent, a dye or a pigment.
  • Alkaline compounds include sodium hydroxide, potassium hydroxide, lithium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate, sodium silicate, potassium silicate, sodium metasilicate, sodium phosphate, potassium phosphate
  • Inorganic alkaline compounds such as sodium hydrogen phosphate, potassium hydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, ammonium hydroxide, mono-di- or triethanolamine, mono-di- or trimethylamine , Mono-di- or triethylamine, mono- or diisopropylamine, n-butylamine, mono-di- or triisopropanolamine, ethyleneimine, ethylenediimine, tetramethylammonium hydroxide (TMAH), choline, etc.
  • Organic alkaline compounds. These alkaline compounds may be a mixture of two or more.
  • surfactant examples include nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, monoglyceride alkyl esters, and alkylbenzene sulfonic acids.
  • nonionic surfactants such as polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene alkyl esters, sorbitan alkyl esters, monoglyceride alkyl esters, and alkylbenzene sulfonic acids.
  • anionic surfactants such as salts, alkylnaphthalene sulfonates, alkyl sulfates, alkyl sulfonates, and sulfosuccinate esters
  • amphoteric surfactants such as alkylbetaines and amino acids.
  • organic solvent examples include isopropyl alcohol, benzyl alcohol, ethyl cellosolve, butyl cellosolve, phenyl cellosolve, propylene glycol, diacetone alcohol and the like.
  • the organic solvent may be used alone or in combination with an aqueous solution.
  • the development processing conditions are not particularly limited, and the development temperature is usually in the range of 10 to 50 ° C., particularly 15 to 45 ° C., particularly preferably 20 to 40 ° C.
  • the development methods are immersion development, spray development, brush Any of a developing method, an ultrasonic developing method and the like can be used.
  • thermosetting treatment The substrate after development is subjected to thermosetting treatment or photocuring treatment, preferably thermosetting treatment.
  • the thermosetting treatment conditions at this time are selected such that the temperature is in the range of 100 to 280 ° C., preferably in the range of 150 to 250 ° C., and the time is in the range of 5 to 60 minutes.
  • the line width of the black matrix formed as described above is usually 3 to 50 ⁇ m, preferably 4 to 30 ⁇ m, and the height is usually 0.5 to 5 ⁇ m, preferably 1 to 4 ⁇ m.
  • the volume resistivity is 1 ⁇ 10 13 ⁇ ⁇ cm or more, preferably 1 ⁇ 10 14 ⁇ ⁇ cm or more, and the relative dielectric constant is 6 or less, preferably 5 or less, and usually 2 or more.
  • the optical density (OD) per 1 ⁇ m thickness is 1.2 or more, preferably 1.5 or more, more preferably 1.8 or more, and usually 4.0 or less.
  • the optical density (OD) is a value measured by a method described later.
  • the photosensitive coloring composition of this Embodiment can also be used as a resist for coloring spacers other than a black matrix.
  • a spacer is used in a TFT type LCD, the TFT may malfunction as a switching element due to light incident on the TFT, and a colored spacer is used to prevent this, for example, Japanese Patent Application Laid-Open No. 8-234212.
  • the publication discloses that the spacer is light-shielding.
  • the colored spacer can be formed in the same manner as the black matrix described above except that a mask for the colored spacer is used.
  • the image display device of the present invention is not particularly limited as long as it is a device that displays an image or video, and examples thereof include a liquid crystal display device and an organic EL (Electro Luminesence) display described later.
  • the liquid crystal display device of the present invention is manufactured using the above-described black matrix of the present invention, and is not particularly limited in terms of the formation order and formation position of the color pixels and the black matrix.
  • the black matrix of the present invention is provided on a TFT element substrate, red, green and blue pixels are formed, an overcoat layer is formed as necessary, and further, ITO and IZO are formed on the image.
  • ITO and IZO are formed on the image.
  • the transparent electrode may not be formed.
  • a liquid crystal display device usually forms an alignment film on a color filter, and after dispersing spacers on the alignment film or forming a photo spacer, it is bonded to a counter substrate to form a liquid crystal cell. Liquid crystal is injected into the cell and connected to the counter electrode to complete.
  • a resin film such as polyimide is suitable.
  • a gravure printing method and / or a flexographic printing method is usually employed, and the thickness of the alignment film is several tens of nm.
  • the alignment film is cured by thermal baking, it is surface-treated by irradiation with ultraviolet rays or a rubbing cloth to be processed into a surface state in which the tilt of the liquid crystal can be adjusted.
  • the black matrix of the present invention there is no particular limitation on the formation order and formation position of the color pixels and the black matrix.
  • the spacer a spacer having a size corresponding to a gap (gap) with the counter substrate is used, and a spacer of 2 to 8 ⁇ m is usually preferable.
  • a photo spacer (PS) of a transparent resin film can be formed on the color filter substrate by photolithography, and this can be used instead of the spacer.
  • the gap for bonding to the counter substrate varies depending on the use of the liquid crystal display device, but is usually selected in the range of 2 to 8 ⁇ m.
  • portions other than the liquid crystal injection port are sealed with a sealing material such as an epoxy resin.
  • the sealing material is cured by UV irradiation and / or heating, and the periphery of the liquid crystal cell is sealed.
  • the liquid crystal cell whose periphery is sealed is cut into panel units, then decompressed in a vacuum chamber, the liquid crystal injection port is immersed in liquid crystal, and then the liquid crystal is injected into the liquid crystal cell by leaking in the chamber. .
  • the degree of decompression in the liquid crystal cell is usually 1 ⁇ 10 ⁇ 2 to 1 ⁇ 10 ⁇ 7 Pa, preferably 1 ⁇ 10 ⁇ 3 to 1 ⁇ 10 ⁇ 6 Pa. Further, it is preferable to heat the liquid crystal cell during decompression, and the heating temperature is usually 30 to 100 ° C., more preferably 50 to 90 ° C.
  • the warming holding at the time of depressurization is usually in the range of 10 to 60 minutes, and then immersed in the liquid crystal.
  • the liquid crystal cell into which the liquid crystal is injected is sealed with a UV curable resin in which the liquid crystal injection port is cured, thereby completing a liquid crystal display device (panel).
  • liquid crystal there are no particular restrictions on the type of liquid crystal, and it is a conventionally known liquid crystal such as an aromatic, aliphatic, or polycyclic compound, and may be any of lyotropic liquid crystal, thermotropic liquid crystal, and the like.
  • thermotropic liquid crystal nematic liquid crystal, smectic liquid crystal, cholesteric liquid crystal, and the like are known, but any of them may be used.
  • the organic EL display of the present invention can be produced using the black matrix of the present invention.
  • a pattern that is, the pixel 20 and the adjacent one
  • a color filter in which a black matrix (not shown) provided between the pixels 20 is formed is produced, and an organic light-emitting body 500 is laminated on the color filter with the organic protective layer 30 and the inorganic oxide film 40 interposed therebetween.
  • the organic EL element 100 can be produced.
  • at least one of the pixel 20 and the black matrix is manufactured using the photosensitive coloring composition of the present invention.
  • a transparent anode 50, a hole injection layer 51, a hole transport layer 52, a light-emitting layer 53, an electron injection layer 54, and a cathode 55 are sequentially formed on the upper surface of the color filter.
  • a method of adhering the organic light-emitting body 500 formed on another substrate onto the inorganic oxide film 40 can be used.
  • an organic EL display can be produced.
  • the black matrix of the present invention can be applied to both passive drive type organic EL displays and active drive type organic EL displays.
  • Organic black pigment Perylene black> Lumogen (registered trademark) Black FK4281 manufactured by BASF
  • Organic black pigment aniline black> PALIOTOL (registered trademark) Black L0080, manufactured by BASF
  • the inside of the reaction vessel was changed to air substitution, 0.7 parts by mass of trisdimethylaminomethylphenol and 0.12 parts by mass of hydroquinone were added to 43.2 parts by mass of acrylic acid, and the reaction was continued at 100 ° C. for 12 hours. Thereafter, 56.2 parts by mass of tetrahydrophthalic anhydride (THPA) and 0.7 parts by mass of triethylamine were added and reacted at 100 ° C. for 3.5 hours.
  • THPA tetrahydrophthalic anhydride
  • the weight average molecular weight Mw measured by GPC of the alkali-soluble resin-I thus obtained was about 8400, and the acid value was 80 mgKOH / g.
  • ⁇ Dispersant-II> "DISPERBYK-2000" manufactured by Big Chemie (acrylic AB block copolymer consisting of an A block having a quaternary ammonium base in the side chain and a B block having no quaternary ammonium base)
  • compound 1 (0.98 g, 5 mmol) and methylene chloride (17 mL) were added to a 50 mL three-necked flask. After cooling to 3 ° C., o-toluoyl chloride (0.77 g, 5 mmol) was added dropwise. To this, aluminum chloride (0.67 g, 5 mmol) was slowly added over 1 hour. After completion of the addition, the mixture was further stirred at 3 ° C. for 2 hours, and methylene chloride (8 mL) was added. Next, glutaric anhydride (0.68 g, 6 mmol) was added over 30 minutes, and then aluminum chloride (1.90 g, 14 mmol) was added over 30 minutes.
  • compound 3 (1.00 g, 2.26 mmol) and methylene chloride (10 mL) were placed in a 50 mL three-necked flask and cooled to 10 ° C. To this was added 1N hydrogen chloride in diethyl ether (4.68 mL). Next, amyl nitrite (0.36 g, 3.04 mmol) was added and reacted at 10 ° C. for 4 hours. After adding water (10 mL), it wash
  • ⁇ Preparation of pigment dispersions 1 to 7 The pigment, dispersant, dispersion aid, alkali-soluble resin, and solvent described in Table 1 were mixed so that the mass ratio described in Table 1 was obtained. This solution was subjected to a dispersion treatment in the range of 25 to 45 ° C. for 3 hours using a paint shaker. As the beads, 0.5 mm ⁇ zirconia beads were used, and 2.5 times the mass of the dispersion was added. After the completion of dispersion, the beads and dispersion were separated by a filter to prepare pigment dispersions 1 to 7.
  • Carbon black was produced by a normal oil furnace method. However, as the raw material oil, an ethylene bottom oil having a small amount of Na, Ca, and S was used, and a coke oven gas was used for combustion. Furthermore, pure water treated with an ion exchange resin was used as the reaction stop water. 540 g of the obtained carbon black was stirred at 5,000 to 6,000 rpm for 30 minutes together with 14500 g of pure water using a homomixer to obtain a slurry.
  • the slurry was transferred to a container with a screw type stirrer, and 600 g of toluene in which 60 g of epoxy resin “Epicoat 828” (manufactured by Mitsubishi Chemical Corporation) was dissolved was added little by little while mixing at about 1,000 rpm. In about 15 minutes, the entire amount of carbon black dispersed in water was transferred to the toluene side, and became particles of about 1 mm.
  • Examples 1 to 8 and Comparative Examples 1 to 4 Using the pigment dispersion and the coated carbon black dispersion prepared above, each component was added so that the ratio in the solid content was the mixing ratio shown in Table 2, and further PGMEA was added so that the solid content was 17% by mass. The mixture was stirred and dissolved to prepare a photosensitive coloring composition. In Examples 1 to 8 and Comparative Examples 1, 2 and 4, the pigment concentration in the solid content was 40% by mass, and in Comparative Example 3, the pigment concentration in the solid content was 30% by mass.
  • the mass ratio of the alkali-soluble resin (including the resin in the dispersion) to the photopolymerizable monomer is 3, the photopolymerization initiator is 4% by mass in the solid content, and the additive is 0.5% by mass and 0.1% by mass of the surfactant were used.
  • the obtained photosensitive coloring composition it evaluated by the method mentioned later.
  • the prepared photosensitive coloring composition was applied to a glass substrate with a spin coater so that the final film thickness was 2 ⁇ m, dried under reduced pressure for 1 minute, and then dried at 100 ° C. for 90 seconds with a hot plate.
  • a resist-coated substrate (substrate-1) was obtained by heating at 230 ° C. for 30 minutes.
  • the optical density (OD) of the obtained substrate was measured with a transmission densitometer Gretag Macbeth D200-II, and the film thickness was measured with a non-contact surface / layer cross-sectional shape measurement system VertScan (R) 2.0 manufactured by Ryoka System Co., Ltd. It was measured.
  • Table 3 shows the optical density (OD) per 1 ⁇ m of film thickness.
  • a substrate (substrate-2) was prepared in the same manner as in the method for preparing substrate-1, except that a glass substrate having a chromium vapor deposition film was used instead of the glass substrate.
  • a gold counter electrode was formed on the resist coating film by vapor deposition.
  • the relative dielectric constant at 1 kHz ⁇ 1 V was measured using “LCR meter 4284A” manufactured by HP (current Agilent). The results are shown in Table 3.
  • Example 1 From a comparison between Example 1 and Comparative Examples 1, 2, and 4, it was confirmed that the substrate obtained from the photosensitive coloring composition of the present invention had a higher OD and a higher shielding property at the same pigment concentration. .
  • Comparative Examples 1 and 2 a linear pattern was not obtained even after development for 10 minutes. This is because Comparative Examples 1 and 2 contain perylene black as a pigment, but it is necessary to use a large amount of dispersant when dispersing perylene black, which seems to have adversely affected the plate-making characteristics. The larger the line width, the higher the sensitivity. However, by using (A-1) the organic black pigment and (A-2) the organic coloring pigment together, the sensitivity can be improved without greatly reducing the OD. It was confirmed from Examples 4 and 5 that it could be increased.
  • Comparative Example 3 shows that the pigment is only coated carbon black and exhibits a high OD, but the relative dielectric constant increases.
  • Examples 6 and 7 show that the combination of (A-1) organic black pigment and (A-3) carbon black used in the present invention enables high OD and low dielectric constant. confirmed.
  • Example 9 and Comparative Examples 5 to 7 Using the pigment dispersion prepared above, add each component so that the ratio in the solid content is the blending ratio in Table 5, and add PGMEA so that the solid content is 17% by mass, and stir and dissolve. A photosensitive coloring composition was prepared. Moreover, the viscosity was measured about each obtained photosensitive coloring composition by the Toki Sangyo Co., Ltd. RC80L type
  • a basic polymer dispersant having a quaternary ammonium base and a basic polymer dispersant having no quaternary ammonium base are treated equally. It is known to show the same dispersibility.
  • perylene black which is an organic black pigment, has no significant difference in the viscosity of the photosensitive coloring composition when using Dispersant I or Dispersant III. .
  • Table 6 shows the viscosity values measured in the same manner as in Example 9 for the photosensitive coloring compositions of Examples 1 to 8.
  • Example 6 in which (A-1) an organic black pigment and (A-3) carbon black were used in combination, (A-1) an organic black pigment and (A-2) an organic color pigment (A-3)
  • the viscosity was the same as in Examples 1 and 2, and the pigment was uniformly dispersed in any of the photosensitive coloring compositions.

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Abstract

　La présente invention aborde le problème consistant à pourvoir à une composition colorante photosensible présentant d'excellentes performances de blocage de la lumière tout en présentant également d'excellentes propriétés de dispersion et d'exécution de plaque et présentant de manière appropriée une faible permittivité relative. Ladite composition colorante photosensible contient au moins un colorant (A), un dispersant (B), une résine (C) soluble dans les alcalis, et un initiateur de polymérisation (D). Le colorant (A) comprend un pigment noir organique, qui constitue le composé (A-1) représenté par la formule générale (1), un isomère géométrique dudit composé, un sel dudit composé, ou un sel d'un isomère géométrique dudit composé ; et le dispersant (B) comprend un dispersant polymère ayant en tant que groupe fonctionnel un groupe de sel d'ammonium quaternaire.　
PCT/JP2014/075144 2013-09-25 2014-09-22 Composition colorante photosensible, matrice à fond noir, espaceur de coloration, dispositif d'affichage d'image, et dispersion de pigment WO2015046178A1 (fr)

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JP2015506015A JP6489008B2 (ja) 2013-09-25 2014-09-22 感光性着色組成物、着色スペーサー及び画像表示装置
KR1020207007432A KR102210576B1 (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액
KR1020227002415A KR102485543B1 (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액
KR1020167007364A KR102356749B1 (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액
CN201480051237.0A CN105556390B (zh) 2013-09-25 2014-09-22 感光性着色组合物、黑色矩阵、着色间隔物、图像显示装置及颜料分散液
CN202010078235.8A CN111190328B (zh) 2013-09-25 2014-09-22 感光性着色组合物、黑色矩阵、着色间隔物、图像显示装置及颜料分散液
KR1020177023321A KR101844731B1 (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액
KR1020237018284A KR20230085213A (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액
KR1020227046216A KR102540420B1 (ko) 2013-09-25 2014-09-22 감광성 착색 조성물, 블랙 매트릭스, 착색 스페이서, 화상 표시 장치 및 안료 분산액

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Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016133574A (ja) * 2015-01-16 2016-07-25 Jsr株式会社 感放射線性着色組成物、着色パターン、その形成方法及び液晶表示素子
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